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Better than new and built in 2025, this beautifully appointed home sits on a quiet premium lot backing to woods and the community pond. Offering nearly 2,000 square feet of living space, three bedrooms, and two full baths, it pairs modern finishes with a peaceful setting. The kitchen features an expansive island, quartz countertops, subway tile backsplash, stainless steel appliances, and a walk-in pantry, with plenty of room for everyday meals and entertaining. Luxury vinyl plank flooring flows throughout the main living spaces. The primary suite offers a tray ceiling, walk-in closet, and spacious en suite bath with a double vanity and walk-in shower. A dedicated laundry room with a high-efficiency washer and dryer and a spacious garage add everyday convenience. Outside, the fully fenced backyard thoughtfully combines vinyl fencing along the sides for privacy with aluminum fencing across the rear to preserve the wooded and pond views. Located in a community across from the Chesapeake Bay Environmental Center, this move-in-ready home offers a beautiful place to settle in and enjoy life on the Shore.

211 Pathfinder Cir, Grasonville

Listing courtesy of Samson Properties. Contact:

$1,300,000

Wye River Waterfront Living at Its Best! If you love boating, fishing, crabbing, and being on the water, this Cape Cod-style home on the Wye River may be just what you have been waiting for. Situated on 1.46 private acres with more than 250 feet of waterfront, this property offers a peaceful setting surrounded by mature trees, beautiful landscaping, and plenty of privacy. The Wye River is well known for its excellent boating, fishing, and crabbing, along with its deep water that makes it especially appealing to boaters. Whether you are looking for a full-time residence, a second home, or an investment opportunity, this property offers tremendous possibilities. Enjoy the outdoors from the private screened porch, the perfect place to relax, entertain, and take in the peaceful surroundings. Inside, the home offers four bedrooms and two and a half baths, with generously sized rooms throughout. The first-floor primary suite provides the convenience of one-level living and makes the home well suited for those looking to remain in the home long term. Upstairs are three spacious bedrooms and a full bath, providing plenty of room for family and guests. The light-filled family room features a beautiful fireplace and offers a comfortable space for both relaxing and entertaining. A separate game room provides even more flexibility for gatherings, hobbies, or recreation. Recent improvements include new flooring, a new septic system, and a new roof, giving you a great foundation to add your own personal touches. The property also offers excellent versatility. It could potentially be used as a second home or rental property, and the layout lends itself to possibilities such as an in-law suite or caretaker accommodations, depending on your needs and applicable approvals. With its private setting, mature trees, extensive waterfront, deep-water boating potential, and flexible floor plan, this four-bedroom Cape Cod with a two-car-plus garage is a rare opportunity to enjoy the Wye River lifestyle. Bring your boat, fishing gear, crab pots, and your vision—and make this special waterfront property your own!

Wye River Waterfront Living at Its Best! If you love boating, fishing, crabbing, and being on the water, this Cape Cod-style home on the Wye River may be just what you have been waiting for. Situated on 1.46 private acres with more than 250 feet of waterfront, this property offers a peaceful setting surrounded by mature trees, beautiful landscaping, and plenty of privacy. The Wye River is well known for its excellent boating, fishing, and crabbing, along with its deep water that makes it especially appealing to boaters. Whether you are looking for a full-time residence, a second home, or an investment opportunity, this property offers tremendous possibilities. Enjoy the outdoors from the private screened porch, the perfect place to relax, entertain, and take in the peaceful surroundings. Inside, the home offers four bedrooms and two and a half baths, with generously sized rooms throughout. The first-floor primary suite provides the convenience of one-level living and makes the home well suited for those looking to remain in the home long term. Upstairs are three spacious bedrooms and a full bath, providing plenty of room for family and guests. The light-filled family room features a beautiful fireplace and offers a comfortable space for both relaxing and entertaining. A separate game room provides even more flexibility for gatherings, hobbies, or recreation. Recent improvements include new flooring, a new septic system, and a new roof, giving you a great foundation to add your own personal touches. The property also offers excellent versatility. It could potentially be used as a second home or rental property, and the layout lends itself to possibilities such as an in-law suite or caretaker accommodations, depending on your needs and applicable approvals. With its private setting, mature trees, extensive waterfront, deep-water boating potential, and flexible floor plan, this four-bedroom Cape Cod with a two-car-plus garage is a rare opportunity to enjoy the Wye River lifestyle. Bring your boat, fishing gear, crab pots, and your vision—and make this special waterfront property your own!

117 River Run, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

$725,000

Welcome home to this sanctuary that beautifully blends modern comfort with warm Eastern Shore charm. Nestled at the end of a quiet cul-de-sac in the desirable Willow Branch East community, this property offers a sprawling 1.61-acre lot with * 5 BEDROOMS * A welcoming front porch leads into a dramatic two-story open foyer featuring an elegant staircase. The main level boasts a bright, flexible formal dining room or home office and a spacious living room. At the heart of the home is a spacious kitchen fully equipped with Silestone countertops, 42" Maple Toffee cabinetry, and brand-new stainless steel appliances, plus a generous keeping room perfect for large gatherings. Transition effortlessly through the cozy sunroom—complete with a stylish barn door—to the rear stone paver patio for seamless indoor-outdoor entertaining. Upstairs, the private primary suite serves as a true sanctuary, showcasing a spacious sitting room and a spa-like en-suite bath with a jetted soaking tub. Four additional bedrooms and a full hall bath provide ample space for family and guests. Premium Andersen windows flood the home with natural light, while upgrades like a Rinnai tankless water heater, reverse osmosis, a water softener, and recent two-zone heat pumps (2023 & 2025) ensure modern comfort. With the holidays around the corner an added feature...conveniently located inside.... HOLIDAY LIGHT SWITCH FOR THE FRONT ELEVATION! Located just minutes from historic Centreville, enjoy peaceful, private living with convenient commuter access to Route 301, Annapolis, Easton, and the Chesapeake Bay Bridge.

5 Beds ⋅ 3 Baths

Welcome home to this sanctuary that beautifully blends modern comfort with warm Eastern Shore charm. Nestled at the end of a quiet cul-de-sac in the desirable Willow Branch East community, this property offers a sprawling 1.61-acre lot with * 5 BEDROOMS * A welcoming front porch leads into a dramatic two-story open foyer featuring an elegant staircase. The main level boasts a bright, flexible formal dining room or home office and a spacious living room. At the heart of the home is a spacious kitchen fully equipped with Silestone countertops, 42" Maple Toffee cabinetry, and brand-new stainless steel appliances, plus a generous keeping room perfect for large gatherings. Transition effortlessly through the cozy sunroom—complete with a stylish barn door—to the rear stone paver patio for seamless indoor-outdoor entertaining. Upstairs, the private primary suite serves as a true sanctuary, showcasing a spacious sitting room and a spa-like en-suite bath with a jetted soaking tub. Four additional bedrooms and a full hall bath provide ample space for family and guests. Premium Andersen windows flood the home with natural light, while upgrades like a Rinnai tankless water heater, reverse osmosis, a water softener, and recent two-zone heat pumps (2023 & 2025) ensure modern comfort. With the holidays around the corner an added feature...conveniently located inside.... HOLIDAY LIGHT SWITCH FOR THE FRONT ELEVATION! Located just minutes from historic Centreville, enjoy peaceful, private living with convenient commuter access to Route 301, Annapolis, Easton, and the Chesapeake Bay Bridge.

153 White Tail Ct, Centreville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$799,000

Profressional Photos COMING SOON! Welcome to 223 Evelyne Street in Gibson’s Grant! Built by Koch Homes, this expanded Ashford model combines the convenience of a main-level primary bedroom with spacious living areas and an oversized garage with an enlarged family room above. Hardwood floors, plantation shutters throughout the home, and a beautiful stone-surround fireplace add warmth and timeless style. The spacious living room, kitchen, and dining area offer a welcoming setting for everyday living and entertaining, while a separate office provides a dedicated space for work or study. A beautiful Andersen sliding door opens to the deck and hardscaped patio, creating an inviting outdoor space for dining, relaxing, and gathering. Two additional bedrooms and a full bathroom are located upstairs. A standout feature is the expanded family room over the garage, known as the FROG. The oversized garage option provides additional space for parking and storage below and a larger recreation room above—perfect for a media room, game room, or additional living space. Plumbing is already in place within the wall for a potential future full bathroom, offering added flexibility to make the space your own. Gibson’s Grant offers a waterfront community setting with an outdoor pool, clubhouse, fitness center, and fishing and crabbing pier. Enjoy direct access to the Cross Island Trail and easy access to Route 50, the Bay Bridge, waterfront restaurants, shopping, and everyday conveniences. Discover the space, versatility, and coastal lifestyle that make this home a special opportunity on Kent Island.

Profressional Photos COMING SOON! Welcome to 223 Evelyne Street in Gibson’s Grant! Built by Koch Homes, this expanded Ashford model combines the convenience of a main-level primary bedroom with spacious living areas and an oversized garage with an enlarged family room above. Hardwood floors, plantation shutters throughout the home, and a beautiful stone-surround fireplace add warmth and timeless style. The spacious living room, kitchen, and dining area offer a welcoming setting for everyday living and entertaining, while a separate office provides a dedicated space for work or study. A beautiful Andersen sliding door opens to the deck and hardscaped patio, creating an inviting outdoor space for dining, relaxing, and gathering. Two additional bedrooms and a full bathroom are located upstairs. A standout feature is the expanded family room over the garage, known as the FROG. The oversized garage option provides additional space for parking and storage below and a larger recreation room above—perfect for a media room, game room, or additional living space. Plumbing is already in place within the wall for a potential future full bathroom, offering added flexibility to make the space your own. Gibson’s Grant offers a waterfront community setting with an outdoor pool, clubhouse, fitness center, and fishing and crabbing pier. Enjoy direct access to the Cross Island Trail and easy access to Route 50, the Bay Bridge, waterfront restaurants, shopping, and everyday conveniences. Discover the space, versatility, and coastal lifestyle that make this home a special opportunity on Kent Island.

223 Evelyne St, Chester

Listing courtesy of Samson Properties. Contact:

$489,900

Welcome to 2011 Stevens Drive — a completely renovated home offering exceptional one-level living with a spacious, open floor plan and a long list of thoughtful upgrades throughout. From top to bottom, this home has been transformed with modern finishes, new flooring, fresh paint, updated lighting, renovated bathrooms, and a beautifully redesigned kitchen. The oversized kitchen features quartz countertops, updated appliances, abundant cabinetry, and plenty of workspace, with a large laundry room conveniently located just off the kitchen. Just off the kitchen, a beautifully appointed private dining room provides an elegant space for entertaining and hosting gatherings. With its versatility, this room could also serve as a sophisticated home office, library, or additional flex space to suit your lifestyle. The expansive living room is truly a showstopper, featuring dramatic 30-foot ceilings, recessed lighting, a fireplace, and an open, airy feel that makes the space perfect for both everyday living and entertaining. New LVP flooring flows throughout the entire home, complemented by all-new lighting fixtures and fresh paint throughout. The spacious primary suite offers a private retreat with a walk-in closet, a beautifully updated bathroom with a double quartz vanity, and a rare feature — direct access to the rear deck. Step outside from the primary suite and enjoy views overlooking the peaceful, wooded rear yard. Two additional bedrooms provide plenty of flexibility, including an oversized bedroom with its own walk-in closet. Both bathrooms have been completely updated with new vanities and quartz countertops. Additional improvements include a brand-new roof with a 30-year warranty, an oversized two-car attached garage, abundant storage, and thoughtful updates throughout. With its expansive living spaces, impressive ceiling height, renovated kitchen and baths, private wooded setting, and exceptional primary suite, 2011 Stevens Drive delivers refined, turnkey one-level living at its finest.

Welcome to 2011 Stevens Drive — a completely renovated home offering exceptional one-level living with a spacious, open floor plan and a long list of thoughtful upgrades throughout. From top to bottom, this home has been transformed with modern finishes, new flooring, fresh paint, updated lighting, renovated bathrooms, and a beautifully redesigned kitchen. The oversized kitchen features quartz countertops, updated appliances, abundant cabinetry, and plenty of workspace, with a large laundry room conveniently located just off the kitchen. Just off the kitchen, a beautifully appointed private dining room provides an elegant space for entertaining and hosting gatherings. With its versatility, this room could also serve as a sophisticated home office, library, or additional flex space to suit your lifestyle. The expansive living room is truly a showstopper, featuring dramatic 30-foot ceilings, recessed lighting, a fireplace, and an open, airy feel that makes the space perfect for both everyday living and entertaining. New LVP flooring flows throughout the entire home, complemented by all-new lighting fixtures and fresh paint throughout. The spacious primary suite offers a private retreat with a walk-in closet, a beautifully updated bathroom with a double quartz vanity, and a rare feature — direct access to the rear deck. Step outside from the primary suite and enjoy views overlooking the peaceful, wooded rear yard. Two additional bedrooms provide plenty of flexibility, including an oversized bedroom with its own walk-in closet. Both bathrooms have been completely updated with new vanities and quartz countertops. Additional improvements include a brand-new roof with a 30-year warranty, an oversized two-car attached garage, abundant storage, and thoughtful updates throughout. With its expansive living spaces, impressive ceiling height, renovated kitchen and baths, private wooded setting, and exceptional primary suite, 2011 Stevens Drive delivers refined, turnkey one-level living at its finest.

2011 Stevens Dr, Chester

Listing courtesy of Samson Properties. Contact:

$539,000

DON’T WAIT on 109 Autumn Lane! This home checks the boxes buyers are looking for, open floor plan, HUGE backyard, brand-new composite deck, stone fire pit and patio and a beautifully renovated primary bathroom. PLUS: New roof - New garage door - Bonus space above the garage, finish it for additional living space or use it for tons of storage Big-ticket updates are DONE, the backyard is ready to enjoy, and there’s room to make it your own. Come see this one before someone else does!

DON’T WAIT on 109 Autumn Lane! This home checks the boxes buyers are looking for, open floor plan, HUGE backyard, brand-new composite deck, stone fire pit and patio and a beautifully renovated primary bathroom. PLUS: New roof - New garage door - Bonus space above the garage, finish it for additional living space or use it for tons of storage Big-ticket updates are DONE, the backyard is ready to enjoy, and there’s room to make it your own. Come see this one before someone else does!

109 Autumn Ln, Centreville

Listing courtesy of RE/MAX Executive. Contact:

$1,495,000

A home like you’ve never seen before is COMING SOON to Prospect Bay. Stunning water views, an incredible backyard oasis with pool and guest house, and a coveted location in one of the Eastern Shore’s premier golf course communities. This is more than a home, it’s the Prospect Bay lifestyle buyers wait for. Don’t let this one slip through your hands. Stay tuned.

5 Beds ⋅ 4 Baths

A home like you’ve never seen before is COMING SOON to Prospect Bay. Stunning water views, an incredible backyard oasis with pool and guest house, and a coveted location in one of the Eastern Shore’s premier golf course communities. This is more than a home, it’s the Prospect Bay lifestyle buyers wait for. Don’t let this one slip through your hands. Stay tuned.

228 Prospect Bay Dr W, Grasonville

Listing courtesy of RE/MAX Executive. Contact:

$465,000

Welcome home to this 3-bedroom, 2-bath home situated on .75 acres along a peaceful road backing to mature trees and farmland. Inside, you'll find an inviting open kitchen and living area featuring a charming brick wood-burning fireplace, creating a warm and comfortable gathering space. Step outside to the oversized back deck, perfect for entertaining, relaxing, or enjoying the private country setting. The backyard is ready for summer with a fenced 18' x 36' in-ground saltwater pool, offering plenty of space for outdoor fun and gatherings. Adding even more versatility to the property is the 30' x 40' detached garage, approximately five years old, complete with a half bath and 220V electrical service for electric vehicle charging—ideal for vehicles, hobbies, a workshop, or additional storage. Recent updates include a new heat pump in 2026, new furnace in 2025 and roof 5 years old. With plenty of outdoor space, a pool, an impressive detached garage, and peaceful views, this property offers a great combination of comfort, functionality, and country living.

Welcome home to this 3-bedroom, 2-bath home situated on .75 acres along a peaceful road backing to mature trees and farmland. Inside, you'll find an inviting open kitchen and living area featuring a charming brick wood-burning fireplace, creating a warm and comfortable gathering space. Step outside to the oversized back deck, perfect for entertaining, relaxing, or enjoying the private country setting. The backyard is ready for summer with a fenced 18' x 36' in-ground saltwater pool, offering plenty of space for outdoor fun and gatherings. Adding even more versatility to the property is the 30' x 40' detached garage, approximately five years old, complete with a half bath and 220V electrical service for electric vehicle charging—ideal for vehicles, hobbies, a workshop, or additional storage. Recent updates include a new heat pump in 2026, new furnace in 2025 and roof 5 years old. With plenty of outdoor space, a pool, an impressive detached garage, and peaceful views, this property offers a great combination of comfort, functionality, and country living.

515 Baxter Rd, Sudlersville

Listing courtesy of Benson & Mangold, LLC. Contact:

$789,990

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

2 Beds ⋅ 3 Baths

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

830 Warbler Way Unit 2843, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$749,990

Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in March 2027, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in March 2027, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

830 Warbler Way Unit 2824, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$744,900

Every season brings a new perspective from this exceptional top-floor penthouse at Four Seasons at Kent Island. Set within one of the Eastern Shore’s premier 55+ communities, this beautifully appointed residence offers Chester River views from every room, creating a remarkable backdrop from sunrise through sunset. Gently enjoyed as a seasonal retreat, the home reflects a refined coastal aesthetic with custom shiplap accent walls, curated designer lighting, elegant trimmed tray ceilings, and every premium builder upgrade offered. These include GE Monogram appliances, quartz countertops, LVP flooring, gas fireplace, and dry bar cabinets with top shelf glass doors. The sophisticated open-concept design seamlessly connects the spacious living room, gracious dining area, and chef-inspired kitchen, creating an inviting setting for entertaining or simply relaxing. Beyond the residence, Four Seasons at Kent Island offers an exceptional resort-style lifestyle. Enjoy the heated indoor and outdoor pools, scenic Chester River walking trails just steps from the property, and a vibrant Clubhouse featuring fitness and exercise classes, pickleball, tennis and bocce courts. wellness lectures, mahjong and other board games, numerous social gatherings, and an array of activities designed to bring neighbors together. With the ease of low-maintenance condo living, beautiful waterfront surroundings, convenient access to local marinas, and easy connectivity to the Bay Bridge and points beyond, this penthouse captures the very best of the Eastern Shore lifestyle—elevated, effortless, and truly exceptional

2 Beds ⋅ 3 Baths

Every season brings a new perspective from this exceptional top-floor penthouse at Four Seasons at Kent Island. Set within one of the Eastern Shore’s premier 55+ communities, this beautifully appointed residence offers Chester River views from every room, creating a remarkable backdrop from sunrise through sunset. Gently enjoyed as a seasonal retreat, the home reflects a refined coastal aesthetic with custom shiplap accent walls, curated designer lighting, elegant trimmed tray ceilings, and every premium builder upgrade offered. These include GE Monogram appliances, quartz countertops, LVP flooring, gas fireplace, and dry bar cabinets with top shelf glass doors. The sophisticated open-concept design seamlessly connects the spacious living room, gracious dining area, and chef-inspired kitchen, creating an inviting setting for entertaining or simply relaxing. Beyond the residence, Four Seasons at Kent Island offers an exceptional resort-style lifestyle. Enjoy the heated indoor and outdoor pools, scenic Chester River walking trails just steps from the property, and a vibrant Clubhouse featuring fitness and exercise classes, pickleball, tennis and bocce courts. wellness lectures, mahjong and other board games, numerous social gatherings, and an array of activities designed to bring neighbors together. With the ease of low-maintenance condo living, beautiful waterfront surroundings, convenient access to local marinas, and easy connectivity to the Bay Bridge and points beyond, this penthouse captures the very best of the Eastern Shore lifestyle—elevated, effortless, and truly exceptional

111 Marshgrass Way Unit 43, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$330,000

107 Lee Rd is a one-story Chester home with a streamlined layout and a fully fenced backyard. The kitchen provides ample counter space, white cabinetry, a refrigerator, a range, and a nearby utility nook. The main living area has windows and an open connection to the kitchen, creating flexible space for dining and everyday use. The primary bedroom includes two windows and closet storage, while the bathroom has a vanity and a tub-shower combination. A dedicated laundry area includes a washer and dryer. The broad backyard contains a storage shed, completing this residence with practical interior organization and useful outdoor storage.

3 Beds ⋅ 1 Baths

107 Lee Rd is a one-story Chester home with a streamlined layout and a fully fenced backyard. The kitchen provides ample counter space, white cabinetry, a refrigerator, a range, and a nearby utility nook. The main living area has windows and an open connection to the kitchen, creating flexible space for dining and everyday use. The primary bedroom includes two windows and closet storage, while the bathroom has a vanity and a tub-shower combination. A dedicated laundry area includes a washer and dryer. The broad backyard contains a storage shed, completing this residence with practical interior organization and useful outdoor storage.

107 Lee Rd, Chester

Listing courtesy of Open Door Brokerage, LLC. Contact:

$599,900

New Listing! Bayside Condos * End Unit with Garage * Direct Water Views * Direct View of Castle Harbor Marina * Best Location in the Community* Potential to See Your Boat From Your Window * Many Upgrades * Renovated Kitchen * Renovated Primary Bath * Balcony Off Primary w Water Views * Large Walk-In Closet * Dramatic Ship Lap Accent Wall * Waterside Double Width Deck * Dual Zoned HVAC * Community Pool, Hot Tub, Tennis, Volleyball, Exercise Room and On-Site Property Manager * Condo Dues Cover Roof, Siding, Gutters, Lawn Care, Grass Cutting, Pest Control * Public Water, Public Sewer * Gas Fireplace * Convenient Chester Location Close To Shopping and Grocery

3 Beds ⋅ 4 Baths

New Listing! Bayside Condos * End Unit with Garage * Direct Water Views * Direct View of Castle Harbor Marina * Best Location in the Community* Potential to See Your Boat From Your Window * Many Upgrades * Renovated Kitchen * Renovated Primary Bath * Balcony Off Primary w Water Views * Large Walk-In Closet * Dramatic Ship Lap Accent Wall * Waterside Double Width Deck * Dual Zoned HVAC * Community Pool, Hot Tub, Tennis, Volleyball, Exercise Room and On-Site Property Manager * Condo Dues Cover Roof, Siding, Gutters, Lawn Care, Grass Cutting, Pest Control * Public Water, Public Sewer * Gas Fireplace * Convenient Chester Location Close To Shopping and Grocery

208 Widgeon Way, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

$3,495,000

Set on nearly **3 private acres with more than 300 feet of Chesapeake Bay waterfront**, 419 Craney Creek is a custom-built home designed to embrace its remarkable setting. Over 6,000 square feet of living space offers 4 bedrooms, 4.5 baths, a first-floor primary suite, private office, bonus room and a 3-car side-loading garage. Inside, hardwood floors and abundant natural light carry throughout the home, while the dramatic two-story living room—with its fireplace and expansive windows—captures sweeping Bay views. The spacious kitchen is equally suited for entertaining and everyday living with custom cabinetry, granite countertops, a generous island, abundant workspace and a butler’s pantry. The first-floor primary suite is a retreat of its own, complete with a fireplace and direct access to the waterfront patio. Outdoor spaces unfold across the back of the home, from the covered porch and deck to the paver patio with 10 person hot tub and second-level porch—each offering a front-row seat to the **Chesapeake Bay and unforgettable sunsets**. A private pier with boat lifts and riprapped shoreline complete the waterfront experience, while the expansive grounds offer plenty of room for a future pool. An unfinished basement with rough-in and spacious unfinished attic provide even more opportunity to create additional living, entertaining or recreation space. **Beautifully established yet filled with possibility, 419 Craney Creek offers the space, privacy and waterfront lifestyle that make a Chesapeake Bay property truly special.**

4 Beds ⋅ 6 Baths

Set on nearly **3 private acres with more than 300 feet of Chesapeake Bay waterfront**, 419 Craney Creek is a custom-built home designed to embrace its remarkable setting. Over 6,000 square feet of living space offers 4 bedrooms, 4.5 baths, a first-floor primary suite, private office, bonus room and a 3-car side-loading garage. Inside, hardwood floors and abundant natural light carry throughout the home, while the dramatic two-story living room—with its fireplace and expansive windows—captures sweeping Bay views. The spacious kitchen is equally suited for entertaining and everyday living with custom cabinetry, granite countertops, a generous island, abundant workspace and a butler’s pantry. The first-floor primary suite is a retreat of its own, complete with a fireplace and direct access to the waterfront patio. Outdoor spaces unfold across the back of the home, from the covered porch and deck to the paver patio with 10 person hot tub and second-level porch—each offering a front-row seat to the **Chesapeake Bay and unforgettable sunsets**. A private pier with boat lifts and riprapped shoreline complete the waterfront experience, while the expansive grounds offer plenty of room for a future pool. An unfinished basement with rough-in and spacious unfinished attic provide even more opportunity to create additional living, entertaining or recreation space. **Beautifully established yet filled with possibility, 419 Craney Creek offers the space, privacy and waterfront lifestyle that make a Chesapeake Bay property truly special.**

419 Craney Creek Rd, Stevensville

Listing courtesy of Samson Properties. Contact:

$265,000

This two-bedroom, one-and-a-half-bath townhome in Centreville offers a convenient in-town location, close to shopping and restaurants. Well-maintained and freshly painted, this unit is ready for you to move in and enjoy!

2 Beds ⋅ 1 Baths

This two-bedroom, one-and-a-half-bath townhome in Centreville offers a convenient in-town location, close to shopping and restaurants. Well-maintained and freshly painted, this unit is ready for you to move in and enjoy!

118 Ridgeview Ct, Centreville

Listing courtesy of TTR Sotheby's International Realty. Contact:

$700,000

Discover an exceptional investment opportunity with this stunning Colonial-style residence operating as a guest favorite on Airbnb. Perfectly positioned just 16 feet from the serene Chester River. Step inside to find an inviting open floor plan that seamlessly connects the family room to the kitchen, creating a warm and welcoming atmosphere. The home is adorned with built-ins and window treatments that enhance its charm, while the cozy carpet and wood floors add a touch of elegance throughout. The property features two fireplaces, providing a cozy ambiance during cooler months, and an attic for additional storage or potential expansion. The upper-floor laundry adds convenience, making this home not only beautiful but functional as well. Outside, the allure continues with a personal in-ground pool, perfect for relaxation and recreation. The expansive 1.43-acre lot offers ample space for outdoor activities, while the breathtaking water views create a tranquil backdrop for your daily life. With water access just steps away, you can enjoy kayaking, fishing, or simply soaking in the natural beauty of the Chester River. From an investment perspective, this property stands out with its excellent condition and desirable features. The combination of spacious living areas, modern amenities, and proximity to water activities makes it highly attractive for potential renters or future buyers. The growing demand for waterfront properties ensures that your investment will appreciate over time, providing both immediate enjoyment and long-term financial benefits. This residence is not just a home; it's a lifestyle choice that offers the perfect blend of comfort, luxury, and investment potential. Don't miss your chance to own a piece of paradise that promises both personal enjoyment and financial growth. Seize this opportunity today!

129 Anna Carol Dr, Stevensville

Listing courtesy of Northrop Realty. Contact:

$589,000

5 Beds ⋅ 3 Baths

Discover an exceptional investment opportunity with this stunning Colonial-style residence operating as a guest favorite on Airbnb. Perfectly positioned just 16 feet from the serene Chester River. Step inside to find an inviting open floor plan that seamlessly connects the family room to the kitchen, creating a warm and welcoming atmosphere. The home is adorned with built-ins and window treatments that enhance its charm, while the cozy carpet and wood floors add a touch of elegance throughout. The property features two fireplaces, providing a cozy ambiance during cooler months, and an attic for additional storage or potential expansion. The upper-floor laundry adds convenience, making this home not only beautiful but functional as well. Outside, the allure continues with a personal in-ground pool, perfect for relaxation and recreation. The expansive 1.43-acre lot offers ample space for outdoor activities, while the breathtaking water views create a tranquil backdrop for your daily life. With water access just steps away, you can enjoy kayaking, fishing, or simply soaking in the natural beauty of the Chester River. From an investment perspective, this property stands out with its excellent condition and desirable features. The combination of spacious living areas, modern amenities, and proximity to water activities makes it highly attractive for potential renters or future buyers. The growing demand for waterfront properties ensures that your investment will appreciate over time, providing both immediate enjoyment and long-term financial benefits. This residence is not just a home; it's a lifestyle choice that offers the perfect blend of comfort, luxury, and investment potential. Don't miss your chance to own a piece of paradise that promises both personal enjoyment and financial growth. Seize this opportunity today!

325 Rings End Rd, Millington

Listing courtesy of Hostetter Realty. Contact:

$599,900

Nestled in the serene enclave of Kent Island Estates, this exquisite new construction home, soon to be completed in 2026, embodies the perfect blend of luxury and comfort. With a stunning Craftsman architectural style, this detached residence offers a warm and inviting atmosphere, ideal for those seeking an exclusive lifestyle. Step inside to discover a thoughtfully designed open floor plan that seamlessly connects the living, dining, and kitchen areas. The large gourmet kitchen is a chef's dream, featuring upgraded quartz countertops, a spacious island, and stainless-steel appliances, including a sleek oven/range with hood and French door refrigerator with water and ice dispenser. There is abundant cabinet and counter space here, this kitchen is sure to meet your every need. Upstairs this home boasts three generously sized bedrooms, including a primary suite complete with a luxurious bathroom featuring a large double vanity and tiled stall shower ensuring a spa-like experience at home. The primary suite features a huge walk in closet complete with wire shelving. The Primary suite looks out over Eastern Bay and Shipping Creek, a vista that is sure to instill relaxation and peace. Each bedroom is designed with comfort in mind, offering ample closet spaces that provide both functionality and style. Bedroom floors are carpeted for comfort, and ceiling fans ensure temperature control. The upper-level hall bath is also equipped with a large double vanity for convenience and a generous tub shower combination. The main interior is adorned with luxury vinyl plank flooring and wainscoted walls, enhancing the home's aesthetic while ensuring durability. The upper floor laundry adds convenience to your daily routine, making chores a breeze. Outside, the property is graced with a level water oriented front yard and a level lot that backs to trees, providing a tranquil backdrop for outdoor gatherings. Enjoy the fresh air on the expansive deck, perfect for entertaining or simply unwinding after a long day. The paved driveway leads to an attached garage, offering both convenience and security. Located just one block from the picturesque Shipping Creek, this home offers a unique opportunity to embrace a water-oriented lifestyle. The views of the bay and creek create a serene environment, perfect for nature lovers and those seeking a peaceful retreat. Kent Island Estates is a suburban haven, providing easy access to local amenities while maintaining a sense of privacy and tranquility. This property is not just a home; it's a lifestyle choice that promises comfort, elegance, and a connection to nature. Experience the luxury of new construction and the joy of creating lasting memories in this exceptional residence.

Nestled in the serene enclave of Kent Island Estates, this exquisite new construction home, soon to be completed in 2026, embodies the perfect blend of luxury and comfort. With a stunning Craftsman architectural style, this detached residence offers a warm and inviting atmosphere, ideal for those seeking an exclusive lifestyle. Step inside to discover a thoughtfully designed open floor plan that seamlessly connects the living, dining, and kitchen areas. The large gourmet kitchen is a chef's dream, featuring upgraded quartz countertops, a spacious island, and stainless-steel appliances, including a sleek oven/range with hood and French door refrigerator with water and ice dispenser. There is abundant cabinet and counter space here, this kitchen is sure to meet your every need. Upstairs this home boasts three generously sized bedrooms, including a primary suite complete with a luxurious bathroom featuring a large double vanity and tiled stall shower ensuring a spa-like experience at home. The primary suite features a huge walk in closet complete with wire shelving. The Primary suite looks out over Eastern Bay and Shipping Creek, a vista that is sure to instill relaxation and peace. Each bedroom is designed with comfort in mind, offering ample closet spaces that provide both functionality and style. Bedroom floors are carpeted for comfort, and ceiling fans ensure temperature control. The upper-level hall bath is also equipped with a large double vanity for convenience and a generous tub shower combination. The main interior is adorned with luxury vinyl plank flooring and wainscoted walls, enhancing the home's aesthetic while ensuring durability. The upper floor laundry adds convenience to your daily routine, making chores a breeze. Outside, the property is graced with a level water oriented front yard and a level lot that backs to trees, providing a tranquil backdrop for outdoor gatherings. Enjoy the fresh air on the expansive deck, perfect for entertaining or simply unwinding after a long day. The paved driveway leads to an attached garage, offering both convenience and security. Located just one block from the picturesque Shipping Creek, this home offers a unique opportunity to embrace a water-oriented lifestyle. The views of the bay and creek create a serene environment, perfect for nature lovers and those seeking a peaceful retreat. Kent Island Estates is a suburban haven, providing easy access to local amenities while maintaining a sense of privacy and tranquility. This property is not just a home; it's a lifestyle choice that promises comfort, elegance, and a connection to nature. Experience the luxury of new construction and the joy of creating lasting memories in this exceptional residence.

510 Talbot Rd, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

$455,000

Welcome to this beautifully maintained and thoughtfully designed home, ideally situated on a desirable corner lot with a fully fenced backyard. Offering an excellent combination of comfort, functionality, and style, this property is an ideal opportunity for a first-time buyer, growing family, or anyone looking for a move-in-ready home. Step inside and you’ll immediately appreciate the inviting traditional floor plan, enhanced by beautiful new wood flooring, recessed lighting, upgraded countertops, and an abundance of natural light. The spacious family room flows seamlessly from the kitchen, creating a comfortable and welcoming space for everyday living and entertaining. The well-appointed kitchen offers an abundance of workspace and storage, featuring a center island, pantry, eat-in area, table space, upgraded countertops, built-in microwave, built-in range, self-cleaning oven, dishwasher, and exhaust fan. Whether you’re preparing a quick breakfast or hosting family and friends, this kitchen provides the convenience and functionality today’s homeowners desire. The home offers two full bathrooms, including one with a convenient walk-in shower. Generously sized bedrooms provide comfortable living spaces, while walk-in closets offer excellent storage. Ceiling fans and window treatments throughout the home add comfort and convenience. The main-level laundry area makes everyday living simple and efficient, with a washer and electric dryer included. Additional features include storm doors, double-hung windows, an electric alarm system, an owned water-conditioning system, a water-treatment system, and a water heater. The crawl space has also received important improvements. All cavities and walls have been fully insulated and sealed, and a dedicated dehumidifier system has been installed to help maintain a cleaner, drier, and more controlled environment beneath the home. Outside, the spacious corner-lot setting and fully fenced backyard provide plenty of room for outdoor enjoyment, entertaining, gardening, play, or simply relaxing. The backyard offers the privacy, flexibility, and functionality many buyers are looking for, making it an ideal space for families and outdoor activities. With its comfortable living spaces, practical upgrades, excellent storage, and inviting outdoor setting, this home offers an exceptional opportunity to establish roots and enjoy years of comfortable living. Whether you’re purchasing your first home, looking for additional space for your family, or simply searching for a well-maintained property in a desirable setting, this home is one you won’t want to miss.

Welcome to this beautifully maintained and thoughtfully designed home, ideally situated on a desirable corner lot with a fully fenced backyard. Offering an excellent combination of comfort, functionality, and style, this property is an ideal opportunity for a first-time buyer, growing family, or anyone looking for a move-in-ready home. Step inside and you’ll immediately appreciate the inviting traditional floor plan, enhanced by beautiful new wood flooring, recessed lighting, upgraded countertops, and an abundance of natural light. The spacious family room flows seamlessly from the kitchen, creating a comfortable and welcoming space for everyday living and entertaining. The well-appointed kitchen offers an abundance of workspace and storage, featuring a center island, pantry, eat-in area, table space, upgraded countertops, built-in microwave, built-in range, self-cleaning oven, dishwasher, and exhaust fan. Whether you’re preparing a quick breakfast or hosting family and friends, this kitchen provides the convenience and functionality today’s homeowners desire. The home offers two full bathrooms, including one with a convenient walk-in shower. Generously sized bedrooms provide comfortable living spaces, while walk-in closets offer excellent storage. Ceiling fans and window treatments throughout the home add comfort and convenience. The main-level laundry area makes everyday living simple and efficient, with a washer and electric dryer included. Additional features include storm doors, double-hung windows, an electric alarm system, an owned water-conditioning system, a water-treatment system, and a water heater. The crawl space has also received important improvements. All cavities and walls have been fully insulated and sealed, and a dedicated dehumidifier system has been installed to help maintain a cleaner, drier, and more controlled environment beneath the home. Outside, the spacious corner-lot setting and fully fenced backyard provide plenty of room for outdoor enjoyment, entertaining, gardening, play, or simply relaxing. The backyard offers the privacy, flexibility, and functionality many buyers are looking for, making it an ideal space for families and outdoor activities. With its comfortable living spaces, practical upgrades, excellent storage, and inviting outdoor setting, this home offers an exceptional opportunity to establish roots and enjoy years of comfortable living. Whether you’re purchasing your first home, looking for additional space for your family, or simply searching for a well-maintained property in a desirable setting, this home is one you won’t want to miss.

101 Chestnut Rd, Stevensville

Listing courtesy of EXP Realty, LLC. Contact:

$635,000

Let your home business dreams become a reality! Zoned mixed use residential/commercial! This charming traditional home, offers a perfect blend of comfort and functionality. With 2,818 square feet of thoughtfully designed living space, this residence features five spacious bedrooms and two and a half bathrooms, ensuring ample room for relaxation and privacy. Step inside to discover a cozy family room with wood burning fireplace that seamlessly connects to the kitchen, creating an inviting space for gatherings and everyday living. The kitchen boasts a gorgeous quartz island, perfect for casual meals or entertaining guests as well as a tastefully designed formal dining room. As you move upstairs, you'll find four spacious bedrooms and 2 full bathrooms including a primary suite. Enjoy the luxury of a soaking tub in the primary bathroom, providing a serene escape after a long day. The 3rd floor features an oversized bedroom or recreation room. The possibilities are endless, create a home gym, theatre or gaming room or office space. Outside, the property features a side-entry garage with additional storage space, ensuring convenience and organization. The 0.27-acre lot provides a lovely fenced in outdoor area for gardening or simply enjoying the fresh air. This home is not just a place to live; it's a place to create lasting memories. Experience the perfect blend of style, comfort, and functionality in this delightful residence. Multi-use zoning allows your home business dreams to come true. Zoned residential and commercial.

1616 Postal Rd, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

$300,000

COMING SOON on Kent Island! Opportunity awaits at 205 Dominion Ln in Chester. Currently used as a rental, this detached home offers the chance to bring your vision and make it your own. The property could use some TLC, but for the right buyer, that’s exactly where the potential begins. Whether you’re looking for a home you can update over time and turn into your own Eastern Shore retreat, or you’re an investor searching for your next project or rental opportunity, this property offers plenty of possibilities. Located on sought-after Kent Island with convenient access to everything the area has to offer. Bring your ideas and imagine what this home could become. More details and photos coming soon!

COMING SOON on Kent Island! Opportunity awaits at 205 Dominion Ln in Chester. Currently used as a rental, this detached home offers the chance to bring your vision and make it your own. The property could use some TLC, but for the right buyer, that’s exactly where the potential begins. Whether you’re looking for a home you can update over time and turn into your own Eastern Shore retreat, or you’re an investor searching for your next project or rental opportunity, this property offers plenty of possibilities. Located on sought-after Kent Island with convenient access to everything the area has to offer. Bring your ideas and imagine what this home could become. More details and photos coming soon!

205 Dominion Ln, Chester

Listing courtesy of EXP Realty, LLC. Contact:

$1,350,000

Coastal elegance meets effortless waterfront living on the sunrise side of Prospect Bay. From the moment you arrive, this exceptional home feels special. Ideally positioned on a picturesque jut of land, the setting offers a bit of additional protection while showcasing beautiful, ever-changing water views and spectacular sunrises. A circular driveway leads to a charming courtyard entrance framed by lush perennial gardens. Inside, the views immediately take center stage. An open, coastal elegant floor plan bring the beauty of Prospect Bay into every living space. Coffered ceilings elevate the spacious family and dining rooms, while substantial crown molding and elegant finishes add timeless character throughout. The expansive kitchen is as beautiful as it is functional, featuring a 9-foot island with seating, stainless steel appliances, wine cooler, accent lighting, soft-close cabinetry and drawers, and a pantry. And the views? Simply fabulous. Large sliders open to the heated and cooled sunroom, where walls of windows create a spectacular connection to the water. Designed for both entertaining and relaxing, this may quickly become your favorite room in the house. The custom bar is an exceptional conversation piece, crafted with mahogany and other wood from a 1963 Chris-Craft. The primary suite offers a private retreat with water views and direct access to the waterside patio. A generous, customized walk-in closet leads to the beautifully appointed primary bath, featuring double sinks, a private water closet, and an extraordinary L-shaped tiled walk-in shower with showerheads on two walls. Two bedrooms are thoughtfully positioned on the opposite wing of the home with 1 additional bed and full bath on primary wing. Outside, waterfront living truly comes alive. Enjoy morning coffee and evening gatherings on the Trex deck, or head down to the private pier where two boat lifts await, including an impressive 12,000-pound lift. A spacious shed provides convenient additional storage. And the community setting adds even more to the lifestyle, with a boat ramp, waterfront children's playground, picnic area, and kayak launch—all offering easy ways to get outside and enjoy. This home is designed for waterfront living.

Coastal elegance meets effortless waterfront living on the sunrise side of Prospect Bay. From the moment you arrive, this exceptional home feels special. Ideally positioned on a picturesque jut of land, the setting offers a bit of additional protection while showcasing beautiful, ever-changing water views and spectacular sunrises. A circular driveway leads to a charming courtyard entrance framed by lush perennial gardens. Inside, the views immediately take center stage. An open, coastal elegant floor plan bring the beauty of Prospect Bay into every living space. Coffered ceilings elevate the spacious family and dining rooms, while substantial crown molding and elegant finishes add timeless character throughout. The expansive kitchen is as beautiful as it is functional, featuring a 9-foot island with seating, stainless steel appliances, wine cooler, accent lighting, soft-close cabinetry and drawers, and a pantry. And the views? Simply fabulous. Large sliders open to the heated and cooled sunroom, where walls of windows create a spectacular connection to the water. Designed for both entertaining and relaxing, this may quickly become your favorite room in the house. The custom bar is an exceptional conversation piece, crafted with mahogany and other wood from a 1963 Chris-Craft. The primary suite offers a private retreat with water views and direct access to the waterside patio. A generous, customized walk-in closet leads to the beautifully appointed primary bath, featuring double sinks, a private water closet, and an extraordinary L-shaped tiled walk-in shower with showerheads on two walls. Two bedrooms are thoughtfully positioned on the opposite wing of the home with 1 additional bed and full bath on primary wing. Outside, waterfront living truly comes alive. Enjoy morning coffee and evening gatherings on the Trex deck, or head down to the private pier where two boat lifts await, including an impressive 12,000-pound lift. A spacious shed provides convenient additional storage. And the community setting adds even more to the lifestyle, with a boat ramp, waterfront children's playground, picnic area, and kayak launch—all offering easy ways to get outside and enjoy. This home is designed for waterfront living.

1509 Calvert Rd, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,199,000

SPECTACULAR WATERFRONT VIEWS OF A LIFETIME! Luxury and the Coveted "BIG SIX" Rare to Come on the Market * Full Water Access * Deeded 40' Deep Water Boat Slip * Attached Garage * 3 Waterside Decks * Experience the epitome of Luxury Living in this exquisite waterfront townhouse nestled in the prestigious Oyster Cove community. This stunning 3-bedroom, 3.5-bath plus a spacious bonus room with it's own private walk out deck gives you that flexible space for a bedroom suite, a home office, or a game room! An open floor plan on the main level is adorned with rich hickory wood floors, recessed lighting, the ambiance of a wood burning fireplace, and a gourmet kitchen featuring upgraded countertops and new stainless steel appliances. Panoramic Bay Views from your open family room, dining room and waterside deck!! Indulge in the primary suite with Breathtaking Bay Views, a walk-in closet, and a spa-like bathroom complete with a whirlpool tub and walk-in shower. Step outside to your private oasis, where a walk out deck off your bonus room invites you to unwind while overlooking the serene Eastern Bay. Enjoy exclusive access to community amenities, including a saltwater pool, tennis/ pickleball courts, a dog park and a 1 1/2 mile trail that connects to the 38+ mile Cross Island Trail! With a gated entrance and meticulously maintained grounds, this home offers a feeling of both tranquility and security. Located just steps from many local restaurants, coffee shops, tiki bars, and dessert spots! You are just minutes to premier golf courses and designer outlet shopping! Move right in and start enjoying an elevated Waterfront Lifestyle!

3 Beds ⋅ 4 Baths

SPECTACULAR WATERFRONT VIEWS OF A LIFETIME! Luxury and the Coveted "BIG SIX" Rare to Come on the Market * Full Water Access * Deeded 40' Deep Water Boat Slip * Attached Garage * 3 Waterside Decks * Experience the epitome of Luxury Living in this exquisite waterfront townhouse nestled in the prestigious Oyster Cove community. This stunning 3-bedroom, 3.5-bath plus a spacious bonus room with it's own private walk out deck gives you that flexible space for a bedroom suite, a home office, or a game room! An open floor plan on the main level is adorned with rich hickory wood floors, recessed lighting, the ambiance of a wood burning fireplace, and a gourmet kitchen featuring upgraded countertops and new stainless steel appliances. Panoramic Bay Views from your open family room, dining room and waterside deck!! Indulge in the primary suite with Breathtaking Bay Views, a walk-in closet, and a spa-like bathroom complete with a whirlpool tub and walk-in shower. Step outside to your private oasis, where a walk out deck off your bonus room invites you to unwind while overlooking the serene Eastern Bay. Enjoy exclusive access to community amenities, including a saltwater pool, tennis/ pickleball courts, a dog park and a 1 1/2 mile trail that connects to the 38+ mile Cross Island Trail! With a gated entrance and meticulously maintained grounds, this home offers a feeling of both tranquility and security. Located just steps from many local restaurants, coffee shops, tiki bars, and dessert spots! You are just minutes to premier golf courses and designer outlet shopping! Move right in and start enjoying an elevated Waterfront Lifestyle!

1007 Oyster Cove Dr, Grasonville

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

$40,000

Looking to own your boat slip instead of paying a hefty lease that could increase year after year? Slip 8-E at Piney Narrows Yacht Haven offers an ownership opportunity in a convenient, community-oriented marina condominium. Measuring 50' x 18' with power, the slip is set beyond a large turnaround area that makes maneuvering easier for larger vessels, including sailboats and sportfish. Located in the heart of Kent Narrows, Piney Narrows Yacht Haven offers a community pool, picnic area with BBQ grill, Yachtsman’s Club lounge, fuel dock with gas and diesel, and complimentary pump-out with fuel purchase. Water, electricity, and Wi-Fi are included. Marina amenities also include winter bubbling at all dock facilities, climate-controlled heads and showers, two laundromats, parking for slip holders and guests, and an on-site canvas shop for new work and repairs. Enjoy convenient access to Kent Narrows restaurants, nearby trails, and popular cruising destinations. Whether you’re seeking a weekend getaway or a home port for the boating season, Slip 8-E offers a comfortable place to enjoy all that Kent Island and the Chesapeake Bay have to offer.

8-E Piney Narrows Rd, Chester

Listing courtesy of Benson & Mangold, LLC. Contact:

$570,000

The view is the main event. Homes throughout Queens Landing sit at varying distances from the waterfront, and it is hard to get closer than this. Positioned directly along the Chester River, this end unit delivers huge, panoramic water views that immediately set it apart. The windows are perfectly positioned to take full advantage of the setting, giving you a front-row seat to passing boats, changing skies, and some of the most beautiful views on Kent Island. Inside, the home offers a bright, open floor plan with **dual primary suites**, including one conveniently located on the main level—no steps needed for everyday living. The layout ideal for guests, multigenerational living, or simply having a private retreat on each floor. The main level features luxury vinyl plank flooring, an updated kitchen with stainless steel appliances and granite countertops, and a separate bar area with a wine refrigerator. Shiplap accents bring in just the right amount of coastal character while keeping the space comfortable and inviting. Upstairs, the expanded loft has been thoughtfully enclosed, adding approximately 120 square feet of additional living space. There is plenty of room for a family room or media space along with a separate office, reading nook, or flex area. And even from the upper level, those incredible Chester River views remain front and center. Queens Landing offers a true waterfront lifestyle with a clubhouse, heated outdoor pool overlooking the marina and Chester River, fitness center, tennis and pickleball courts, and easy access to the Cross Island Trail. Restaurants, marinas, shopping, and everyday conveniences are nearby, with Route 50 providing easy access to Annapolis, Baltimore, Washington, D.C., and the beaches.

2 Beds ⋅ 2 Baths

The view is the main event. Homes throughout Queens Landing sit at varying distances from the waterfront, and it is hard to get closer than this. Positioned directly along the Chester River, this end unit delivers huge, panoramic water views that immediately set it apart. The windows are perfectly positioned to take full advantage of the setting, giving you a front-row seat to passing boats, changing skies, and some of the most beautiful views on Kent Island. Inside, the home offers a bright, open floor plan with **dual primary suites**, including one conveniently located on the main level—no steps needed for everyday living. The layout ideal for guests, multigenerational living, or simply having a private retreat on each floor. The main level features luxury vinyl plank flooring, an updated kitchen with stainless steel appliances and granite countertops, and a separate bar area with a wine refrigerator. Shiplap accents bring in just the right amount of coastal character while keeping the space comfortable and inviting. Upstairs, the expanded loft has been thoughtfully enclosed, adding approximately 120 square feet of additional living space. There is plenty of room for a family room or media space along with a separate office, reading nook, or flex area. And even from the upper level, those incredible Chester River views remain front and center. Queens Landing offers a true waterfront lifestyle with a clubhouse, heated outdoor pool overlooking the marina and Chester River, fitness center, tennis and pickleball courts, and easy access to the Cross Island Trail. Restaurants, marinas, shopping, and everyday conveniences are nearby, with Route 50 providing easy access to Annapolis, Baltimore, Washington, D.C., and the beaches.

34 Queen Anne Way Unit A, Chester

Listing courtesy of RE/MAX Executive. Contact:

$1,195,000

A Private Wye River Sanctuary! Some properties offer a home. Others offer a lifestyle. This exceptional Wye River retreat offers both.Set along one of the Eastern Shore’s most beautiful waterways, this beautifully updated ranch home is an invitation to slow down, entertain effortlessly, and enjoy waterfront living at its finest. From morning coffee on the screened porch to sunset swims in the Gunite pool, every day here feels like a getaway.The light-filled, open interior provides an inviting backdrop for relaxed gatherings and everyday living, while a versatile additional living area offers the flexibility for an in-law suite, private home office, game room, or guest retreat. The serene primary bedroom enjoys direct access to the screened porch, creating a private connection to the tranquil waterfront setting.The extensive improvements provide peace of mind while enhancing the home's appeal, including an architectural roof, vinyl siding, gutters, sophisticated hybrid heat pump/propane HVAC system, select updated flooring, and an updated BAT septic system.Outside is where this property truly shines. The Gunite pool features strategically placed bench seating, creating the perfect vantage point for unforgettable Wye River sunsets. The screened porch captures the river breezes and provides an ideal setting for morning coffee, afternoon cocktails, or long evenings with friends and family.For the boating enthusiast, the private dock features two electric boat lifts—8,000 and 12,000 pounds—and 2+ feet of mean low water, providing excellent access for boating and watersports. Spend the day on the river, catch crabs from the dock, or simply let the water set the pace.This is more than a waterfront home—it is a place to create traditions, host unforgettable gatherings, escape the ordinary, and experience the Wye River in a deeply personal way.Private waterfront. Private dock. Gunite pool. Sunset views. Exceptional outdoor living. A rare opportunity to make the Wye River your everyday retreat.

A Private Wye River Sanctuary! Some properties offer a home. Others offer a lifestyle. This exceptional Wye River retreat offers both.Set along one of the Eastern Shore’s most beautiful waterways, this beautifully updated ranch home is an invitation to slow down, entertain effortlessly, and enjoy waterfront living at its finest. From morning coffee on the screened porch to sunset swims in the Gunite pool, every day here feels like a getaway.The light-filled, open interior provides an inviting backdrop for relaxed gatherings and everyday living, while a versatile additional living area offers the flexibility for an in-law suite, private home office, game room, or guest retreat. The serene primary bedroom enjoys direct access to the screened porch, creating a private connection to the tranquil waterfront setting.The extensive improvements provide peace of mind while enhancing the home's appeal, including an architectural roof, vinyl siding, gutters, sophisticated hybrid heat pump/propane HVAC system, select updated flooring, and an updated BAT septic system.Outside is where this property truly shines. The Gunite pool features strategically placed bench seating, creating the perfect vantage point for unforgettable Wye River sunsets. The screened porch captures the river breezes and provides an ideal setting for morning coffee, afternoon cocktails, or long evenings with friends and family.For the boating enthusiast, the private dock features two electric boat lifts—8,000 and 12,000 pounds—and 2+ feet of mean low water, providing excellent access for boating and watersports. Spend the day on the river, catch crabs from the dock, or simply let the water set the pace.This is more than a waterfront home—it is a place to create traditions, host unforgettable gatherings, escape the ordinary, and experience the Wye River in a deeply personal way.Private waterfront. Private dock. Gunite pool. Sunset views. Exceptional outdoor living. A rare opportunity to make the Wye River your everyday retreat.

225 Hickory Ridge Dr, Queenstown

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$1,650,000

Enjoy broad water views and spectacular sunsets from this beautifully situated 1.02-acre waterfront property, with water views enjoyed throughout much of the home. Designed for comfortable one-level living, this spacious residence offers 4 bedrooms, 3.5 baths providing 3,137 square feet of living space. The bright kitchen features a skylight, center island with seating, and an open layout connecting seamlessly to the family room with fireplace. The waterfront primary suite takes full advantage of the views and includes a large walk-in closet, private bath with soaking tub, walk-in shower and dual vanities, plus primary has direct access to a semi-private deck. An additional guest bedroom features its own ensuite bath. Oversized 2 Car Garage. Outdoor living is a highlight, with a swimming pool, deck with awning, patio, generous backyard, riprapped shoreline, and a new pier completed in 2026, Roof New in 2021. This property offers an ideal setting for relaxing, entertaining, and enjoying life on the water. The community offers resort-style amenities, including an 18-hole championship golf course, clubhouse with restaurant/bar/grill, swimming pool, tennis and pickleball courts plus. With expansive water views, beautiful sunsets, one-level living, a private pool and pier, this exceptional property offers the Eastern Shore waterfront lifestyle at its best.

4 Beds ⋅ 4 Baths

Enjoy broad water views and spectacular sunsets from this beautifully situated 1.02-acre waterfront property, with water views enjoyed throughout much of the home. Designed for comfortable one-level living, this spacious residence offers 4 bedrooms, 3.5 baths providing 3,137 square feet of living space. The bright kitchen features a skylight, center island with seating, and an open layout connecting seamlessly to the family room with fireplace. The waterfront primary suite takes full advantage of the views and includes a large walk-in closet, private bath with soaking tub, walk-in shower and dual vanities, plus primary has direct access to a semi-private deck. An additional guest bedroom features its own ensuite bath. Oversized 2 Car Garage. Outdoor living is a highlight, with a swimming pool, deck with awning, patio, generous backyard, riprapped shoreline, and a new pier completed in 2026, Roof New in 2021. This property offers an ideal setting for relaxing, entertaining, and enjoying life on the water. The community offers resort-style amenities, including an 18-hole championship golf course, clubhouse with restaurant/bar/grill, swimming pool, tennis and pickleball courts plus. With expansive water views, beautiful sunsets, one-level living, a private pool and pier, this exceptional property offers the Eastern Shore waterfront lifestyle at its best.

251 Prospect Bay Dr W, Grasonville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$549,900

Welcome to 347 Claiborne Fields Drive, situated on an impressive 1.26 acre lot in the sought-after Claiborne Fields community of Centreville! With over 2,000 square feet of living space, this 3 bedroom, 2.5 bath home has been well maintained and cared for by the original owner for many years. Fresh paint and new carpet throughout give the home a clean, refreshed feel, making it ready for its next chapter. An attached two car garage provides added convenience and plenty of space for parking and storage. Enjoy plenty of room to spread out both inside and out, with a spacious lot backing to woods for added privacy and a peaceful setting. Located in an established community with convenient access to Centreville and Route 301, this home offers a wonderful combination of space, privacy, and location. Come see all that 347 Claiborne Fields Drive has to offer!