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$489,000
4 Beds ⋅ 3 Baths
Enjoy BIG SKY SUNSETS every evening over picturesque farm fields and the Chesapeake Bay! This beautifully maintained Cape Cod offers a spacious primary bedroom suite with a private bath and large closet, plus a brand-new screened-in rear porch and deck—perfect for entertaining and relaxing. Inside, you’ll find hardwood floors on both levels, vaulted ceilings upstairs, granite kitchen countertops, abundant attic/eave storage, an encapsulated crawl space, and much more. Located in the sought-after Cloverfields community on Kent Island, enjoy access to a private sandy beach, community pool, marina, and boat ramp with quick access to the Chester River and Chesapeake Bay. Eastern Shore living at its best—beautiful sunsets, great amenities, and the Island lifestyle! Come see and Enjoy! (Interior pictures coming 8/15)

1010 Love Point Rd, Stevensville

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$899,000
3 Beds ⋅ 2 Baths
Bring your water toys and move right in! Located on the Chester River, this beautifully remodeled water front home is ready for a quick sale so you can enjoy the rest of the prime season! Private pier with 10k lb boat lift and 2 jet ski lifts, built in 2021. Open deck with spectacular views of the sunsets! Inside the home has been upgraded with all new hard surface flooring and neutral decor. A modern kitchen with SS appliances including gas stove, painted wood cabinetry, quartz countertop with bar and pantry. Open concept floor plan with water views from all rooms in the rear. Large dining area opens to the living area with gas fireplace. Sliders are on the entire back of the home offering so much light and breathtaking water views. The one level living is so convenient with 3 bedrooms and 2 full baths. Down the hall from the main living areas are 2 generous bedrooms and a full bath. A separate laundry room featuring a full size washer and dryer, tankless gas water heater and well equipment is tucked away. New well dug 2022 with new pump installed same time. To complete the one level living is an primary en suite offering a walk in closet with built ins and a full bath with double vanities, shower with glass enclosure and linen closet. An added bonus of a detached carriage house with a 20x13 club room with it's own heat and air system. The crawlspace under the main house was encapsulated in 2021 and has a dehumidifier for air quality control. Plenty of parking on the concrete driveway. Vinyl mini shed. Mature landscaping with flowering bushes. This community is so convenient, just minutes to Rt 50, downtown Grasonville, halfway between Stevensville and Queenstown. If you are looking for water front home with a great place for your boat, look no further.

942 Chester River Dr, Grasonville

Listing courtesy of Maryland Real Estate Network. Contact: (240) 456-0016
$924,000
3 Beds ⋅ 3 Baths
Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors in a den setting. The Gourmet Kitchen is special, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and a large island ideal for entertaining. Your primary suite includes a spa style bathroom complete with walk-in shower. The upper level of the home offers an and additional bedroom, and a second family room. Don't miss the full walk in storage area above the garage that is partially finished. More storage is available in the oversized fully finished two car garage with room for a third car or golf cart. Off the dining area is a screened-in porch and paver patio with a fire pit and out door built in grilling area. Backing to the pond, no houses behind you and views of the fountain is what makes this truly an exceptional lot and setting. The community run irrigation system Is an added bonus to this community. You will certainly enjoy the 24,000 square foot Clubhouse located directly on the Chester River. Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, pickle ball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. This development is an unrivaled, amenity-filled, resort-style experience.

214 Bayberry Dr, Chester

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$1,395,000
4 Beds ⋅ 5 Baths
Experience elevated waterfront living in one of Kent Narrows' most desirable marina communities. Perfectly positioned as an end-unit in prestigious Wells Cove Townhomes & Marina, this extensively renovated four-level residence captures sweeping Chesapeake Bay and marina views while offering the rare combination of refined finishes, deep-water boating, and a true lock-and-leave lifestyle. Ready for immediate occupancy, this is the turnkey waterfront home you've been waiting for. Spanning approximately 3,500 square feet, the thoughtfully designed floor plan features four bedrooms, four full baths, one half bath, and a private elevator servicing all four levels. Crafted to satisfy even the most discerning buyer, the home reflects an uncompromising commitment to quality, comfort, and timeless design. Rich hardwood flooring, custom millwork, designer lighting, soaring 9-foot ceilings, abundant natural light, and beautifully renovated interiors create an atmosphere that is both sophisticated and inviting. At the heart of the home is a stunning chef's kitchen, completely redesigned in 2019 with custom cabinetry, premium appliances, stone countertops, an oversized center island, and exceptional workspace. Multiple living and entertaining areas, two spacious owner suites, a loft, and a generous recreation room with a wet bar provide remarkable flexibility for family and guests alike. Four private covered waterfront decks seamlessly extend the living space outdoors, creating the perfect setting to enjoy morning coffee, watch boats glide through the marina, or unwind with spectacular Chesapeake Bay sunsets. From nearly every level, the ever-changing waterfront views become part of everyday life. For boating enthusiasts, the deeded deep-water boat slip is one of the marina's most desirable, offering approximately 4 feet of mean low water and the ability to accommodate a substantial vessel. Ideally positioned for convenient access to the Chesapeake Bay, it provides an exceptional home port for everything from an afternoon cruise to a weekend on the water. An oversized two-car garage offers generous storage for vehicles, bicycles, paddleboards, fishing gear, and all the essentials for an active waterfront lifestyle. Located in the heart of Kent Narrows, you're just moments from waterfront restaurants, marinas, boutique shopping, the Cross Island Trail, golf, and Route 50, providing convenient access to Annapolis, Baltimore, Washington, D.C., and the Delaware and Maryland beaches. Beautifully renovated, impeccably maintained, and completely turnkey, this extraordinary residence presents a rare opportunity to own one of Wells Cove's premier waterfront homes. Simply arrive, settle in, and begin enjoying the Chesapeake Bay lifestyle from day one.

314 Channel Marker Way, Grasonville

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$399,000
2 Beds ⋅ 2 Baths
Waterfront with assigned pier on Thompson Creek – Rare End-Unit Townhome Fantastic opportunity to own an end-unit waterfront townhome with direct views of Thompson Creek, complete with an assigned pier featuring power and water. Inside, gleaming hardwood floors flow through the kitchen and living room. The main level offers a convenient bedroom, while upstairs you'll find a huge loft-style primary suite complete with a spacious primary bathroom featuring an oversized walk-in shower and an equally impressive walk-in closet. A versatile bonus room offers flexibility as a 3rd bedroom or home office. The kitchen offers ample counter space and storage alongside a large dining area, perfect for entertaining. Step outside to a spacious deck to soak in the water views, plus a second private balcony off the primary bedroom. With western exposure, enjoy breathtaking sunsets over the creek every evening. The HOA maintains the pier as well as all exterior upkeep of the home, including the roof and siding, offering true low-maintenance waterfront living. Ideally located on Kent Island, just a half mile to Route 50 and minutes to two shopping centers featuring Food Lion, Target, and a variety of restaurants. Incredible value at $399,000 for waterfront living with a private pier. Furnishings are available for purchase separately, excluding personal items.

101 Marion Quimby Dr, Stevensville

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$998,000
3 Beds ⋅ 3 Baths
Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabulous community center /pool / pier is a short 1 mile walk from your backyard.! This unit also has the largest garage space in the the building, plenty of room for one car and storage, a refrigerator etc. There is also an additional inside storage room. This 2600 Sq Ft home is flooded with natural light and has numerous quality upgrades including custom shiplap in most of the rooms, custom ceiling fans and dining room light fixture, custom built his and hers walk in closets. The primary bath has upgraded tile, shelving for more storage, mulitple shower heads and back and front lit vanity mirrors. The gourmet kitchen is designed to impress, featuring elegant quartz countertops,premium appliances and a Wolfe induction cooktop. The island has been upgraded with shiplap as well. Thoughtful upgrades continue throughout the entire home with custom blinds with remote control, a gas fireplace,9 FT ceilings with tray ceilings in the living room and primary suite. A wet bar has also been added to the dining area.The large primary bedroom comes complete with a sitting area/office with exceptional waterviews. It also offers custom designed his -and -her closets that provide both style and storage. This unique residence offers a peaceful setting where you can relax and enjoy the ever-changing waterfront vistas. Whether you are enjoying your morning coffee or entertaining guests, this home offers the perfect blend of sophistication, comfort, and low maintenance waterfront living.

111 Marshgrass Way Unit #41, Chester

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

$2,840,000
3 Beds ⋅ 2 Baths
Privacy without isolation - Rare Find - 2 comfy houses on one waterfront property! Each with unobstructed views of the picturesque Cox Creek before it enters the Bay. Discover a captivating traditional charm in this vintage cape cod ( 3-bedrooms, 2-bathrooms) recently updated in spring 2026. The former detached garage converted into the guest cottage (2BR, 1.5 BA) has a fabulous screened porch you'll spend endless hours on. A separate building provides versatile storage for equipment or hobbies. Nestled in a serene rural setting, this home boasts picturesque views along the banks of Cox Creek, offering panoramic western vistas that will take your breath away, especially as the sun sets on the horizon. Step inside to find a thoughtfully designed interior featuring rich wood floors in most rooms. Upgraded countertops and new appliances elevate the kitchen, convenient to the screened porch perfect for gatherings. The living room, complete with a brick fireplace, invites warmth and relaxation. Enjoy the convenience of an entry-level bedroom, or home office, in this traditional floor plan that flows seamlessly throughout. The exterior amenities are equally impressive, featuring a private shoreline and a circular gravel driveway that accommodates ample parking. With 548 feet of waterfrontage, indulge in fishing, boating, or simply soaking in the tranquil surroundings. The property includes a private dock with electric hoist and ramp, making water access effortless. . The secluded parcel offers year-round access, ensuring your retreat is always within reach. This home is not just a residence; it's a lifestyle waiting to be embraced. Don't miss the opportunity to make this serene haven your own! Less than 30 minutes to Annapolis, 50 minutes to Baltimore or DC.. Convenient to area restaurants and points of interest. Not under subdivision restrictions. Perfect for multi-generational living, private guest quarters, or possible rental income. Room for expansion of living spaces, outdoor sports court, horseshoes, bocci, or gardens.. Former waterside pool could be revitalized, subject to county approval.

300 Woods Point Rd, Chester

Listing courtesy of Tidewater Properties. Contact:

$1,275,000
4 Beds ⋅ 3 Baths
WATERFRONT LIVING on Winchester Creek! This wonderful 4 bedroom, 2.5 bath Grasonville estate offers the ultimate Eastern Shore lifestyle, fully refreshed with a newly painted neutral interior, gleaming refinished hardwoods, and carpet. A grand 2-story foyer with a palladium window, transom accents, and elegant French doors welcomes you inside. The main level features 11' ceilings, a great room with fireplace and a bank of windows with water views, a separate dining room, bright breakfast room, and a fabulous kitchen with an island, pantry, and reverse osmosis water filtration. The main floor primary suite boasts a walk-in closet and a no-threshold shower, complemented by a full, hall bath and convenient half bath. Upstairs, a versatile bonus space features custom built-ins— perfect for an office and media space. Your outdoor resort awaits: a Trex deck with built-in benches and retractable awning leads to a custom paver patio and a sparkling 18’ x 37’ saltwater pool with a tranquil waterfall feature. Boaters will love the deeded boat slip (#10), mooring pile, and private boat lift. Rounding out this incredible home is an oversized 2-car garage with storage space, HVAC (2018), buried 500-gallon propane tank, and full water conditioning system and lush landscaping.

104 Port Ct, Grasonville

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

$1,990,000
6 Beds ⋅ 5 Baths
The location of this property is fabulous! One of the most beautiful spots on the bay, it features a panoramic view across the bay to Annapolis! Watch the ships going in and out of Baltimore, magnificent sunsets, and the Blue Angels, when they perform! In a small neighborhood, just minutes from the Bay Bridge, the property has all you need for a year-round home or for a week-end or vacation retreat! The cement, heated in-ground pool adjoins the deck and porch areas . A small kitchen and full bath are poolside for coming in from the pool, cleaning your "catch of the day" or steaming crabs! The private pier accommodates a boat lift and two jet-ski lifts. There is rip-rap and bulk heading, and depending on the tide, there is a beach! This uniquely-designed home offers multiple living and dining areas, as well as main and second level bedrooms and a separate office. With its many three-season and screened-in porch areas and outside decks, you can entertain rain or shine! And, by the way, the golfers in the family, need not leave the neighborhood as it abuts the Blue Heron Golf Course! Instead of commuting from your primary home to a vacation home, save yourself the trip...this house has it all! There is a video security system at the property.

206 Queen Anne Club Dr, Stevensville

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

$4,995,000
5 Beds ⋅ 5 Baths
Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

2800 Bennett Point Rd, Queenstown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$1,470,000
5 Beds ⋅ 5 Baths
Waterfront living with lifestyle, location and luxury! Located at the mouth of the Chester River, this home is in the perfect spot for days on the Bay, boat rides to Kent Narrows restaurants, golf at Queenstown and shopping the outlets, all just minutes from the Bay Bridge. This beautifully updated home delivers the best of Eastern Shore living with 259' of waterfront, a community pier, top rated schools and easy access to Annapolis and beyond. The deeded slip (with boat and PWC lifts) makes life on the water effortless. The water views and natural wetlands of Winchester Creek offer sunsets, privacy and abundant birdlife. A mowed path leads to water's edge for kayak and paddleboard launches. This home features more than 4,400 square feet on three finished levels, west-facing water views from expansive windows that fill the home with natural light. The two-story family room features a rebuilt luxury fireplace with custom trim work creating an everyday space that's upscale & comfortable. The renovated gourmet kitchen offers quartz countertops, heated floors, stainless steel appliances, abundant cabinetry, a breakfast nook and a redesigned island perfect for gathering. The first floor also includes a two-story foyer, formal dining room and a comfortable living room/study with large windows and a second fireplace. Hardwood floors, custom millwork, fresh paint and designer finishes create a timeless coastal feel throughout. Single-floor living is easy with two first-level bedroom ensuites. The primary suite offers beautiful water views, California Closets, a remodeled spa-inspired bath and a cozy bay window sitting area. The second ensuite has great water views and is ideal for guests, extended family or a 2nd primary. The second level features three additional bedrooms and a large bonus room perfect for home-office, homework, crafting or playroom. The entire third level is built for entertaining with a wet bar, beverage cooler, full bath and surround sound. Set on 1.37 acres, the property offers privacy, an expansive front and back lawn, updated landscaping and sweeping water views bordered by natural wetlands and habitat. Enjoy morning coffee as the sun rises on the water & glowing sunsets from the new TimberTech deck and covered porch. The slip is steps away from the house and Homeport's private pier (4' MLW) is directly adjacent to the Chester River & Chespeake for daytrips or sunset cruises. Recent improvements include dual Bosch high-efficiency HVAC systems (2023 and 2024), a Rinnai tankless water heater and a whole-house smart water treatment and management system, all housed in a dedicated utility room. Plus, smart thermostats on each floor, Vector security system, invisible pet fence, ceiling fans throughout, professional landscaping, nearly all-new lighting, and updated bathrooms. Enjoy Chesapeake living with great views, great schools and easy access to Annapolis and beyond.

109 Starboard Ct, Grasonville

Listing courtesy of Northrop Realty. Contact: 4105310321
$700,000
2 Beds ⋅ 3 Baths
Priced to sell at just $700,000, this is an exceptional opportunity. With a $160,000 lot premium and over $60,000 in builder upgrades, this home is offered below its replacement value. Experience everything Four Seasons has to offer without the wait. This meticulously maintained home shows like new and is located just steps from the community amenities and vibrant social spaces that make Four Seasons so desirable. 132 Wheelhouse Way offers one of the most desirable locations in the community, with exceptional water views, ground-level access, and an easy walk to the resort-style amenities. Inside, you'll find a gourmet kitchen with quartz countertops, GE Café double wall ovens, upgraded stainless steel appliances, luxury vinyl plank flooring, and an open-concept living space with an electric fireplace and beautiful water views. The primary suite features patio access, a walk-in closet, and a luxurious bath, while the second bedroom suite and private office provide comfort and flexibility. Residents enjoy the Chester House Clubhouse, indoor and outdoor pools, a fitness center, pickleball and tennis courts, walking trails, a kayak launch, fishing pier, dog park, tiki bar, and more. Perfectly located on Kent Island, this home offers an exceptional blend of luxury, convenience, and the Chesapeake Bay lifestyle.

132 Wheelhouse Way Unit #11, Chester

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$670,000
4 Beds ⋅ 3 Baths
If you missed this one the first time, here’s your second chance. The previous contract fell through after the buyer’s review of the HOA covenants and restrictions revealed they did not align with the buyer’s plans and goals. The home is now available again and ready for its next buyer! Welcome home to this Colonial-style home located in the highly sought-after Claiborne Fields in Centreville, MD! Featuring 4 bedrooms and 3 bathrooms, 2 car garage, this exceptional property offers timeless charm, quality construction, and space to grow. From the moment you arrive, the outstanding landscaping and curb appeal make a lasting impression. Inside, you’ll find original hardwood floors throughout, a spacious layout, and attention to detail that truly sets this home apart. The sunroom and patio with a permanent umbrella overlook breathtaking views of fields, mature trees and the peaceful pond, creating the perfect setting for relaxing mornings, entertaining guests, or enjoying nature year-round. Additional highlights include an encapsulated crawl space, new roof, newer heat pumps and furnace all in the past 4 years, granite countertops, Anderson 400 series windows, hot water Rinnai tankless, water treatment system, numerous upgrades throughout, and craftsmanship that must be seen to be appreciated. No detail was missed in the construction quality of this home — you’ll need to read the extensive upgrade list to believe it! Located in a friendly, established neighborhood with convenient access to local amenities, schools, parks, and everything Centreville has to offer. This one is truly special — see the video!

306 Old Line Dr, Centreville

Listing courtesy of Taylor Properties. Contact:

$5,400,000
7 Beds ⋅ 9 Baths
Designed to rival a private resort, this waterfront estate was built for celebrating with family and friends. Sweeping Chesapeake views set the stage for every gathering. The waterfront pool features a cascading rock waterfall, a tucked in bench, and a generous sun shelf, all overlooked by a pool house with a covered summer kitchen, bar, seating area, and full bath with AC. A curated firepit lounge, expansive patios and balconies, and a screened waterside porch bring indoor and outdoor living together for every occasion. At the shoreline, life on the Bay begins, with an expansive private beach perfect for wading, sandcastles, and quiet evenings by the water. The newly expanded L shaped pier stretches 260 feet and is engineered for serious boating, with dockage for a large yacht, 24,000 lb. and 10,000 lb. lifts, electric, R/O water, dual pedestals, and decorative lighting. Protected waters offer calm conditions for docking, fishing, crabbing, and watersports, with direct Bay access and easy cruising to Annapolis, St. Michaels, and beyond. A circular driveway centered by a gorgeous fountain leads to the entry, where a stunning two story foyer and grand staircase greet you, framed by spectacular water views. The great room features a soaring wall of glass and a fireplace, opening to a chef's kitchen appointed with Wolf and Sub Zero appliances, custom cabinetry, a conversation bar, pantry, and breakfast nook. The dining room seats twelve or more, ready for every holiday feast. The primary suite is a private waterfront retreat, with a sitting area beneath a domed ceiling, a fireplace, custom built ins, and a spa bath with heated floors, a jetted soaking tub, and a multi head shower. The waterfront game room offers a fireplace, wet bar, and large TV, while the private theater seats eight in front of a 100 inch screen, making this home the destination for family and friends year round. Upstairs, five architecturally unique bedrooms, three ensuite, include private waterfront balconies and a large activity room opening to a deck overlooking the pool, dock, creek, and bay. A fully equipped in law suite offers its own kitchen, living area, bedroom, fireplace, and attached two car garage, while a separate heated and cooled four car garage with porcelain tile and custom cabinetry serves as studio, workshop, or gym. Six fireplaces, Anderson and Palladian windows, tankless water heaters, a whole house water softener and reverse osmosis system, a 60KW whole house generator, and fiberoptic 2.5GB internet with seventeen access points bring comfort and connectivity throughout. Fully app based control manages lighting, HVAC, security, pool, spa, generator, music, locks, and network, inside and out. Tucked along a quiet private road with easy access to the Bay Bridge, Annapolis, and Washington D.C., this is waterfront vacation living designed to be experienced every day. Serenity Lane describes how you feel, not just where you are. Welcome home.

330 Serenity Ln, Chester

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$2,375,000
4 Beds ⋅ 4 Baths
Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophistication. This fully completed residence is one of just a select offering within the initial collection of three buildings, each thoughtfully designed with only two residences each, creating an intimate and private setting along the water’s edge. Inside, the home unfolds across three levels with a thoughtfully designed four bedroom, four bath layout that offers both flexibility and comfort. A private bedroom and full bath on the entry level provide the perfect space for guests or a quiet home office. The main living level is designed for seamless everyday living and entertaining, highlighted by a warm and inviting living room with a gas fireplace that adds both comfort and ambiance. The upper level features two additional bedroom suites, including a serene primary retreat complete with its own gas fireplace. An elegant touch that enhances the sense of relaxation and retreat. Expansive windows frame captivating views over the marina and out to the Chesapeake Bay, filling the home with natural light and creating an ever-changing backdrop of boating activity and open water. As the day winds down, the setting truly comes to life with breathtaking sunsets that paint the sky and reflect across the water. An experience to be enjoyed from both the interior living spaces and outdoor areas. High-end finishes and a modern, open-concept design elevate the interiors, while the beautifully appointed gourmet kitchen and well designed baths enhance both form and function. Every detail has been curated to deliver a low-maintenance, lock-and-go lifestyle without compromising on luxury. Ideally positioned within walking distance to waterfront dining, including Libbey’s Coastal Kitchen & Cocktails and Knoxie’s Table, residents also enjoy immediate access to marina amenities, scenic walking paths, and the relaxed rhythm of life on the Bay. Sunset Wharf offers a rare opportunity to own a newly completed residence in a thoughtfully designed waterfront community where every day feels like a getaway. Welcome Home!

115 Petrie Way, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$2,375,000
4 Beds ⋅ 4 Baths
Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophistication. This fully completed residence is one of just a select offering within the initial collection of three buildings, each thoughtfully designed with only two residences each, creating an intimate and private setting along the water’s edge. Inside, the home unfolds across three levels with a thoughtfully designed four bedroom, four bath layout that offers both flexibility and comfort. A private bedroom and full bath on the entry level provide the perfect space for guests or a quiet home office. The main living level is designed for seamless everyday living and entertaining, highlighted by a warm and inviting living room with a gas fireplace that adds both comfort and ambiance. The upper level features two additional bedroom suites, including a serene primary retreat complete with its own gas fireplace. An elegant touch that enhances the sense of relaxation and retreat. Expansive windows frame captivating views over the marina and out to the Chesapeake Bay, filling the home with natural light and creating an ever-changing backdrop of boating activity and open water. As the day winds down, the setting truly comes to life with breathtaking sunsets that paint the sky and reflect across the water. An experience to be enjoyed from both the interior living spaces and outdoor areas. High-end finishes and a modern, open-concept design elevate the interiors, while the beautifully appointed gourmet kitchen and well designed baths enhance both form and function. Every detail has been curated to deliver a low-maintenance, lock-and-go lifestyle without compromising on luxury. Ideally positioned within walking distance to waterfront dining, including Libbey’s Coastal Kitchen & Cocktails and Knoxie’s Table, residents also enjoy immediate access to marina amenities, scenic walking paths, and the relaxed rhythm of life on the Bay. Sunset Wharf offers a rare opportunity to own a newly completed residence in a thoughtfully designed waterfront community where every day feels like a getaway. Welcome Home!

119 Petrie Way, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$2,375,000
4 Beds ⋅ 4 Baths
Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophistication. This fully completed residence is one of just a select offering within the initial collection of three buildings, each thoughtfully designed with only two residences each, creating an intimate and private setting along the water’s edge. Inside, the home unfolds across three levels with a thoughtfully designed four bedroom, four bath layout that offers both flexibility and comfort. A private bedroom and full bath on the entry level provide the perfect space for guests or a quiet home office. The main living level is designed for seamless everyday living and entertaining, highlighted by a warm and inviting living room with a gas fireplace that adds both comfort and ambiance. The upper level features two additional bedroom suites, including a serene primary retreat complete with its own gas fireplace. An elegant touch that enhances the sense of relaxation and retreat. Expansive windows frame captivating views over the marina and out to the Chesapeake Bay, filling the home with natural light and creating an ever-changing backdrop of boating activity and open water. As the day winds down, the setting truly comes to life with breathtaking sunsets that paint the sky and reflect across the water. An experience to be enjoyed from both the interior living spaces and outdoor areas. High-end finishes and a modern, open-concept design elevate the interiors, while the beautifully appointed gourmet kitchen and well designed baths enhance both form and function. Every detail has been curated to deliver a low-maintenance, lock-and-go lifestyle without compromising on luxury. Ideally positioned within walking distance to waterfront dining, including Libbey’s Coastal Kitchen & Cocktails and Knoxie’s Table, residents also enjoy immediate access to marina amenities, scenic walking paths, and the relaxed rhythm of life on the Bay. Sunset Wharf offers a rare opportunity to own a newly completed residence in a thoughtfully designed waterfront community where every day feels like a getaway. Welcome Home!

123 Petrie Way, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$2,375,000
4 Beds ⋅ 4 Baths
Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophistication. This fully completed residence is one of just a select offering within the initial collection of three buildings, each thoughtfully designed with only two residences each, creating an intimate and private setting along the water’s edge. Inside, the home unfolds across three levels with a thoughtfully designed four bedroom, four bath layout that offers both flexibility and comfort. A private bedroom and full bath on the entry level provide the perfect space for guests or a quiet home office. The main living level is designed for seamless everyday living and entertaining, highlighted by a warm and inviting living room with a gas fireplace that adds both comfort and ambiance. The upper level features two additional bedroom suites, including a serene primary retreat complete with its own gas fireplace. An elegant touch that enhances the sense of relaxation and retreat. Expansive windows frame captivating views over the marina and out to the Chesapeake Bay, filling the home with natural light and creating an ever-changing backdrop of boating activity and open water. As the day winds down, the setting truly comes to life with breathtaking sunsets that paint the sky and reflect across the water. An experience to be enjoyed from both the interior living spaces and outdoor areas. High-end finishes and a modern, open-concept design elevate the interiors, while the beautifully appointed gourmet kitchen and well designed baths enhance both form and function. Every detail has been curated to deliver a low-maintenance, lock-and-go lifestyle without compromising on luxury. Ideally positioned within walking distance to waterfront dining, including Libbey’s Coastal Kitchen & Cocktails and Knoxie’s Table, residents also enjoy immediate access to marina amenities, scenic walking paths, and the relaxed rhythm of life on the Bay. Sunset Wharf offers a rare opportunity to own a newly completed residence in a thoughtfully designed waterfront community where every day feels like a getaway. Welcome Home!

107 Petrie Way, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$4,700,000
6 Beds ⋅ 6 Baths
Welcome to 200 Wye Road, an exceptional waterfront estate set on over two private acres along the Wye River, directly across from the protected natural beauty of Wye Island. Here, scale, setting, and thoughtful design converge to create a truly elevated Eastern Shore lifestyle. Spanning more than 8,100 square feet across three finished levels, the residence offers a refined yet highly livable floor plan designed to capture water views from nearly every room. Expansive living spaces, a formal dining room with handpainted custom wallpaper from the U.K., and a reimagined gourmet kitchen create an environment equally suited for everyday living and large-scale entertaining. The kitchen has been thoughtfully redesigned with updated cabinetry, statement lighting, and a full suite of premium appliances, including Wolf, Sub-Zero, and Bosch. The home offers exceptional flexibility, including an optional first-floor primary suite, a dedicated home gym, two laundry rooms, and an oversized mudroom designed for seamless day-to-day living. Two wood-burning fireplaces add warmth and character, enhancing the home’s sense of comfort and timeless appeal. The primary suite serves as a private retreat, complete with two walk-in closets and a fully renovated, spa-inspired bath featuring heated flooring, a soaking tub, a glass-enclosed shower, and its own gas fireplace, delivering a level of comfort and detail rarely found. Since 2024, the property has undergone extensive upgrades that enhance both performance and long-term value, including a new Owens Corning roof with a transferable warranty, three fully replaced Trane HVAC systems, a whole-home water filtration system, and comprehensive renovations throughout the bathrooms and interior spaces. Outdoor living is where the property truly distinguishes itself. A newly renovated 20x40 waterfront pool with a pebble finish and automatic cover anchors the setting, complemented by expansive hardscaping, manicured grounds, and multiple areas designed for entertaining or quiet relaxation. The shoreline has been improved with 250 feet of stone rip rap, and the deep-water dock is outfitted with new electrical service and lighting, featuring a new 25,000 lb boat lift and a 12,000 lb one along with two additional slips, providing effortless access to the Wye River and beyond. Whether enjoying sunrise coffee on the screened porch, hosting summer gatherings by the pool, or heading out by boat to St. Michaels or the Kent Narrows, this property offers a lifestyle defined by ease, privacy, and connection to the water. Conveniently located in Queenstown, just minutes from shopping, dining, and Route 50, with easy access to Annapolis and Easton, 200 Wye Road represents a rare opportunity to own a turnkey waterfront estate in one of the Eastern Shore’s most sought-after settings.

200 Wye Rd, Queenstown

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$485,000
2 Beds ⋅ 3 Baths
BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. Easy walk to Kayak launch and creek. With nearly 2000 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area and kitchen, provide an open area for gatherings. The gourmet kitchen is equipped with upgrades from the stunning kitchen island with quartz counter tops, beautiful upgraded cabinetry to the GE Profile appliances. This kitchen is designed for everyday living as well as hosting the occasional dinner party. The primary bedroom, is a separate self-contained suite complete with two closets and a luxury owners' bath that includes double sinks, and quartz countertops. The bright and airy 2nd bedroom is also a separate suite with a full bath and an oversized walk-in closet. In addition to the two bedrooms, there is a home office with stylish French Doors and a powder room for guests. The separate laundry room is equipped with a GE washer and dryer. This home also has a garage with adjoining driveway/parking space and large personal storage room which is a few short steps from the elevator. This home is just a short walk to resident kayak racks with launch access to the Chester River. KEEP IN MIND THIS CHESTER MODEL, WITH PLENTY OF FEATURES AND UPGRADES INCLUDED, IS MOVE-IN READY AND PRICED TO SELL***** Award-winning 24,000 Square Foot Clubhouse with Stunning Chester River Views! Fantastic amenities include 4.3 miles of walking trails throughout the community, outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, lighted pickle ball courts, tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga, a variety of exercise classes and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. In addition to the weekly and monthly activities, residents can enjoy crab feasts, oyster roasts, and holiday gatherings throughout the year. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis, DC, Baltimore, and BWI. Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by views of the Chester River.

1000 Herons Nest Way Unit #22, Chester

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$850,000
1 Beds ⋅ 2 Baths
This Tidewater Cape sits on the point of 13.78 acres and is surrounded by the tidal waters of the Chester River. Built to be a summer home by a father and son in 1950, this home is filled with character and charm. Drive through the woods and catch glimpses of the river to your left. Moments later, the trees open to the homesite, and then notice there is water to your right as well, showcasing the point setting. Cute and cozy from the moment you see it, but this home’s full presence is best appreciated from the rear, where the three-story Tidewater elevation stands proud and timeless. Loved and enjoyed by several generations, the home offers hardwood floors throughout the main and second levels, beautiful built-ins and gorgeous hardwood details throughout. Outdoor living includes a main-level porch and lower-level patio, perfect for taking in the peaceful surroundings. Two outbuildings are located along the shoreline: a one-car garage and a workshop with electric, they offer flexible storage and workspace. There could be potential for subdividing a lot, but buyers to verify all possibilities with the county. Pier/dock conveys As-Is — do not walk on dock. Do Not Enter Property without an appointment.

200 Powers Ln, Millington

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

$515,000
2 Beds ⋅ 3 Baths
WATERFRONT Condo! Open House dates scheduled. Beautifully renovated 2BR/2.5BA waterfront condominium located in the sought-after Queen’s Landing resort-style community on the scenic Chester River, just off the Chesapeake Bay. This move-in-ready home showcases a stunning top-to-bottom remodel, including new luxury vinyl plank flooring, new carpet, fresh paint throughout (ceilings, walls, trim, and doors), new white cabinetry, beautiful quartz countertops with beveled white backsplash, updated bathroom vanities, flooring and modern lighting fixtures. The light-filled open floor plan is designed to highlight the panoramic Chester River views. The spacious family room off the kitchen features an oversized sliding glass door leading to a private balcony with beautiful eastern water views—perfect for morning coffee or relaxing evenings overlooking the river. Upstairs, the primary bedroom suite offers elevated water views and a private full bath. A second large bedroom and additional full bath complete the upper level, with washer and dryer conveniently located between the bedrooms. Residents of Queen’s Landing enjoy exceptional waterfront amenities including a private marina, swimming pool overlooking the Chester River, clubhouse, fitness center, tennis and pickleball courts, and scenic waterfront walking paths. Ideally located just minutes from shopping, dining, entertainment, the Cross Island Trail, and the Chesapeake Bay Bridge, this home is perfect as a full-time residence or weekend waterfront retreat on Maryland’s Eastern Shore. Schedule your private tour today!

34 Queen Anne Way, Chester

Listing courtesy of Taylor Properties. Contact:

$1,215,000
3 Beds ⋅ 4 Baths
Perfectly positioned along the living shoreline of the Chester River, this waterfront residence in the gated community of Narrows Pointe offers breathtaking, million-dollar water views and a lifestyle centered around the beauty of the Eastern Shore. One of the few wide units in the community, the home is thoughtfully designed to maximize its remarkable setting. Three-panel sliding glass doors invite in abundant natural light while framing sweeping water views, and decks on two levels with retractable electric screens create inviting spaces to relax while overlooking the shoreline. A spectacular arrangement of windows throughout the home continually draws your eye to the tranquil river setting. Another plus- Seller has paid the current $10,000 assessment, so the buyer will not be obligated to that. Inside, hardwood flooring, recessed lighting, and a neutral color palette welcome you upon entry. The gourmet kitchen serves as the heart of the home and features granite countertops, a center island with breakfast bar, tile backsplash, wine refrigerator, and 42-inch cabinetry with under-mount lighting and convenient roll-out drawers for easy organization. High-end stainless steel appliances complete the space, and the adjacent dining room provides a bright setting for everyday meals or entertaining. Just off the kitchen, a walk-in pantry and laundry room add everyday convenience and extra storage. Also on the kitchen level is a bedroom suite currently used as an office, enhanced with built-ins that create a comfortable workspace while still offering flexible guest accommodations. The living room showcases a dramatic angled ceiling, a striking stone fireplace, and custom built-ins, creating a warm gathering space while keeping the focus on the surrounding water views. Upstairs, generously sized bedrooms each include en-suite baths with granite-topped vanities. The primary suite offers a peaceful retreat with a walk-in closet featuring built-in organization, a private deck overlooking the river, and a luxurious bath with remote blinds, double vanity, jetted self-cleaning tub, and Toto toilet. Both of the upper-level bedrooms were enhanced with updated hardwood flooring in 2020. The lower-level recreation room adds another versatile living area with a custom bar and cabinetry, making it an ideal space for entertaining. The finished garage features a granite flake floor and storage cabinetry, and the home also includes a whole-house speaker system. Architectural plans are available for the future addition of an elevator. Recent improvements include whole-house interior painting completed in 2020, replacement of the living room sliding glass door, updated electric screens, a 75-gallon water heater, built-ins throughout, professional installation of a TV mount above the fireplace, finished garage upgrades, carpeting and stair runner, water softener, and more. Located near the heart of Kent Narrows, the home offers easy access to a casual waterfront lifestyle with marinas, boating activities, community piers, a kayak launch, and a variety of waterfront restaurants and tiki bars. The Cross Island Trail begins just outside the Narrows Pointe entrance, while shops, hotels, and multiple fitness centers, some with pools, are all within a convenient 10-minute drive. Nearby outdoor destinations such as the local dog park and Terrapin Nature Park add even more ways to enjoy the natural beauty of Maryland’s Eastern Shore.

350 Narrows Pointe Dr, Grasonville

Listing courtesy of Northrop Realty. Contact: 4102956579
$320,000
3 Beds ⋅ 2 Baths
Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

222 Dutchess Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$2,428,725
161.85 acres with NO EASTMENT! Limited by only zoning and your imagination. About 97 tillable, on east and west sides of MD Route 213 between Centreville and Church Hill; 4 platted perk sites, and more potential. Communications Tower lease $837.32/month; In the Queen Anne's County "Opportunity Zone" tax breaks for permitted uses. No Easements! Chesapeake Bay Scenic Byway(Potential sale of easement); Hunting: Goose, Deer, Turkey, wood ducks; 1000+/- feet along both sides of Granny Findley Branch - surrounded by woodland filled with deer. Invest in the future, rent the farmland and hunting rights, farm it yourself, build your dream home no builder tie in.

Sparks Mill Corner - E&W Sparks Mill At Route 213 Rd, Centreville

Listing courtesy of Tidewater Properties. Contact:

$2,428,725
161.85 acres with NO EASTMENT! Limited by only zoning and your imagination. About 97 tillable, on east and west sides of MD Route 213 between Centreville and Church Hill; 4 platted perk sites, and more potential. Communications Tower lease $836.32/month; In the Queen Anne's County "Opportunity Zone" tax breaks for permitted uses. No Easements! Chesapeake Bay Scenic Byway(Potential sale of easement); Hunting: Goose, Deer, Turkey, wood ducks; 1000+/- feet along both sides of Granny Findley Branch - surrounded by woodland filled with deer. Invest in the future, rent the farmland and hunting rights, farm it yourself, build your dream home no builder tie in.

Sparks Corner Sparks Mill At Route 213 Rd, Centreville

Listing courtesy of Tidewater Properties. Contact: