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Parcel 38 Parcel 38 Goldsboro Road, Barclay
$80,000
5-Acre Residential Lot for Sale in Barclay Enjoy the peace and privacy of country living with the convenience of small-town amenities nearby. This approximately 5-acre residential lot is located just outside the town limits of Barclay, offering the benefit of no town property taxes. The property does not have access to public water or sewer. A private well and an approved perc test or other suitable private septic solution will be required prior to development. No perc test has been applied for. Buyer is responsible for conducting their own due diligence regarding zoning, building requirements, well and septic feasibility, and all other matters related to the property’s potential use and development. With a quiet setting and convenient access to major commuting routes, this property offers an excellent opportunity to create your own private homesite while enjoying the charm of small-town living.

Parcel 38 Parcel 38 Goldsboro Road, Barclay

Listing courtesy of Benson & Mangold, LLC. Contact:

Parcel 73 Parcel 73 Barclay Road, Barclay
$85,000
7.5-Acre Residential Lot for Sale in Barclay Enjoy the peace and privacy of country living with the convenience of small-town amenities nearby. This approximately 7.5-acre residential lot is located just outside the town limits of Barclay, offering the benefit of no town property taxes. The property does not have access to public water or sewer. A private well and an approved perc test or other suitable private septic solution will be required prior to development. No perc test has been applied for. Buyer is responsible for conducting their own due diligence regarding zoning, building requirements, well and septic feasibility, and all other matters related to the property’s potential use and development. With a quiet setting and convenient access to major commuting routes, this property offers an excellent opportunity to create your own private homesite while enjoying the charm of small-town living.

Parcel 73 Parcel 73 Barclay Road, Barclay

Listing courtesy of Benson & Mangold, LLC. Contact:

2006 Bennett Point Rd, Queenstown
$1,500,000
4 Beds ⋅ 3 Baths
Spectacular Waterfront Retreat on almost 7 Acres in Exclusive Bennett Point! Welcome to your private paradise on the shores of serene Greenwood Creek! This extraordinary waterfront estate offers almost 7 acres of pure tranquility and luxury, surrounded by water on two sides for a true feeling of seclusion and peace. Your deep-water private pier is a boater’s dream — complete with 3 boat lifts and 2 jet-ski lifts ($150k value just in lifts alone)— perfect for crabbing, fishing, or setting out for a sunset cruise. The home’s Royal Blue Terracotta roof and accents make a bold architectural statement, while the full wrap-around deck ensures you’ll never miss a moment of the breathtaking waterfront views. Step inside and be transported to a stunning waterfront chalet (2x6 construction), where soaring ceilings, skylights, and warm wood accents create a cozy yet grand, open atmosphere. The nearly 3,000 sq. ft. of living space includes a magnificent 35’ x 17’ great room anchored by a floor-to-ceiling stacked-stone fireplace with a wood stove—powerful enough to heat the entire home! The open-concept of the great room, dining and kitchen areas make entertaining a joy. Kitchen features custom cabinetry, granite countertops, a beverage fridge, island, and ample dining space—flowing seamlessly to the screened porch and wrap-around decking. This home also enjoys over 2 thousand ft of heating tubes under the floor for warm-radiant heating you won't find anywhere else! The main level offers 3 spacious bedrooms, 2 full baths, and convenient laundry and storage areas. Upstairs, the cozy loft-style family room with skylights overlooks the great room and leads to a luxurious 25’ x 23’ primary suite, complete with a spa-inspired bath featuring dual sinks, a whirlpool tub, separate shower, and skylights that fill the space with natural light. Every inch of this home was designed to celebrate waterfront living at its finest—a place where comfort meets adventure, and every day feels like a getaway. 🌅 Don’t wait—this rare Bennett Point gem won’t last long!

2006 Bennett Point Rd, Queenstown

Listing courtesy of RE/MAX Executive. Contact:

136 Olive Branch Rd, Stevensville
$649,500
4 Beds ⋅ 3 Baths
LIKE NEW HOME located in the Romancoke on the Bay community featuring 4 bedrooms, 2.5 baths & 2-car side-entry garage situated on a 0.67 acre lot backing to TREES. Walking up to the home the Walk is Stamped Concrete which leads to the Stamped Concrete COVERED Front Porch & Upgraded Front Door. Upon Entering the Home the MAIN Level Features: Primary Bedroom w/ large walk in closet & En-suite Bath w/ Tiled Stall Shower & oversized White Vanity * Luxury vinyl plank flooring throughout the Foyer, Kitchen, Dining & Family Rooms * Gourmet Kitchen w/ White soft-close cabinets, Stainless Appliances, MARBLE countertops & step up counter overlooking Spacious Family Room complete w/ Propane Fireplace * Laundry Room w/ Washer/Dryer included + additional cabinetry w/ Marble countertops * Separate Dining Room w/ pass- thru to Kitchen * Upgraded baseboards & Handrails * Slider off Family Room to 16x20 Stamped Concrete Patio. Upstairs you'll find 3 Spacious bedrooms, all w/ AMPLE Closet space, Additional linen closets in the Hallway & Full Bath w/ Luxury Vinyl Floors, White Vanity & Tub/Shower. Boasting just over 2100sq ft, this home has Elegant features & is Waiting for YOU to Call it HOME! Recent Improvements include: Paved Asphalt Driveway, Kohler Whole House Generator, OWNED 250 gallon Propane Tank, Direct Propane Connection for 2 Grills on the Patio, Gutter Guard system, Custom Hunter Douglas Blinds Throughout the Home, Whole House Water Filtration System + RO system at Kitchen Sink & Exterior Landscaping! Lot has been expanded in size since the original sale providing potential for Pole Barn or other uses! County has approved Olive Branch Rd for paving to be completed approx. Q4 2026/Q1 2027. Home can possibly become active sooner with suitable rent back option for sellers.

136 Olive Branch Rd, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

1520 John Brown Rd, Queenstown
$749,000
3 Beds ⋅ 2 Baths
Welcome to your own private Eastern Shore retreat! Nestled on approximately 17.6 picturesque acres, this charming property offers the perfect blend of peaceful country living and everyday convenience. The home features comfortable one-level living with spacious gathering areas, a cozy wood stove, and beautiful views of the surrounding countryside. Whether you’re looking for room to garden, hunt, farm, enjoy outdoor recreation, or simply relax and take in the tranquility, this property provides endless possibilities. The expansive acreage offers privacy, open space, and the opportunity to create the lifestyle you’ve been dreaming of while still being just a short drive to shopping, dining, and major commuter routes.

1520 John Brown Rd, Queenstown

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

214 Bayberry Dr, Chester
$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:

259 Topside Dr Unit 166, Stevensville
$650,000
3 Beds ⋅ 3 Baths
Professional staging & photos coming soon! Welcome to 259 Topside Drive in Bay Bridge Cove, one of Kent Island’s most sought-after 55+ communities! This beautifully upgraded Oxford model offers the spacious, flexible floor plan buyers love, paired with a premium setting overlooking the community pond and fountain. Step inside to an open and inviting main level designed for both everyday living and entertaining. The gourmet kitchen is a standout, featuring beautiful light gray cabinetry, a custom backsplash that complements it perfectly, an upgraded appliance package, generous workspace and an easy flow into the main living areas. A cozy fireplace anchors the living room, while the expanded double sunroom fills the rear of the home with natural light and creates even more space to relax, entertain or simply enjoy the view. Step outside onto the deck and take in peaceful pond and fountain views—the perfect backdrop for morning coffee, an evening glass of wine or unwinding at the end of the day. The Oxford’s flexible design continues upstairs, where you'll find an additional bedroom and full bath along with a spacious loft and separate den featuring built-in shelving. Whether you need private guest accommodations, a home office, hobby space, reading room or an additional living area, this second level gives you options without sacrificing the convenience of main-level living. Located in the heart of Stevensville on Kent Island, Bay Bridge Cove offers an active, low-maintenance lifestyle with a clubhouse, fitness center, outdoor pool, recreational courts, walking and biking trails, and plenty of opportunities to connect with neighbors—all just minutes from shopping, dining, waterfront recreation and the Chesapeake Bay Bridge. This isn’t just an Oxford—it’s an Oxford with the upgrades, expanded living space and pond setting buyers wait for.

259 Topside Dr Unit 166, Stevensville

Listing courtesy of Samson Properties. Contact:

118 Broadwater Dr, Chester
$656,000
2 Beds ⋅ 2 Baths
Welcome to Resort-Style Living at Four Seasons at Kent Island! Why wait for new construction when you can move right into this beautifully upgraded Donegal model with the sought-after Great Room extension? Offering exceptional value, this is currently the lowest-priced single-family home in the community, making it an outstanding opportunity to enjoy one of Maryland’s premier 55+ active adult neighborhoods. Designed with both elegance and everyday comfort in mind, this home features a stunning Gourmet Kitchen highlighted by a large Quartz Island, premium Gourmet Appliance Package with Double Oven, and abundant workspace—perfect for everything from casual breakfasts to holiday entertaining. The open-concept Great Room creates an inviting gathering place, centered around a warm Gas Fireplace, while upgraded lighting throughout the home adds a sophisticated touch. The Luxury Spa Bath offers a private retreat after a busy day, and Quartz vanities in every bathroom provide both beauty and durability. The thoughtfully designed floor plan includes first-floor bedrooms, allowing comfortable one-level living. A dedicated home office on the main level provides an ideal workspace, hobby room, or can easily function as a third bedroom for visiting family and friends. Additional premium features include elegant Plantation Shutters, an oversized two-car garage with generous storage space, and an underground irrigation system that helps keep your lawn lush while minimizing maintenance. With approximately $89,000 in builder upgrades and options, this home offers exceptional quality and value that would be costly to duplicate today. Come experience the carefree lifestyle of Four Seasons at Kent Island, where resort-style amenities, beautiful surroundings, and a vibrant social atmosphere make every day feel like a vacation. Life in Four Seasons at Kent Island is about more than the home itself. Residents enjoy resort-style amenities including a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball courts, walking trails, kayak launch, fishing pier, and an active social calendar designed for a vibrant lifestyle.

118 Broadwater Dr, Chester

Listing courtesy of RE/MAX Executive. Contact:

1107 Oyster Cove Dr, Grasonville
$759,000
3 Beds ⋅ 4 Baths
NEW PRICE! One of the BEST VIEWS in Oyster Cove! WATERFRONT VIEWS from almost every room! This beautiful, gated community at the Kent Narrows Bridge greets you with scenic entrance ponds and fountains. You feel like you are on vacation while you are working from your home office in this tranquil setting. Grill on your spacious deck while entertaining friends and watching boats heading to St. Michaels/Annapolis, etc. Freshly painted throughout with 3 bedrooms/3.5 baths. Hardwood floors are featured on the 1st/2nd floors plus a TV, FP w/electric insert and built-ins. The updated, eat-in country kitchen features granite counters, beadboard bar and white cabinetry. Waterfront primary suite has a balcony, barn doors, W-I shower, W-I closet and jacuzzi. Utility room is equipped with newer, front-loading washer/dryer. Enjoy the large deck with remote-controlled awning and gate. HWH and W/D 2022. Roof/siding 2019. HVAC 2018. Boat slips available for rent/sale, along with 5 visitor slips for your boating friends. Enjoy the 1.5 mi. WATERFRONT walking path and the beautiful clubhouse w/state-of-the-art gym, full kitchen, holiday parties and monthly socials, game nights, etc. Saltwater pool opens at 6AM so you can enjoy a swim before the heat of the day. Dock your boat in 1 of the 2 marinas where slips range from 35' - 60'. Use the convenient launch pad for your kayak where there is space for > 100 kayaks or take advantage of the 10 jet ski ports. Enjoy a bike ride on the nearby, paved Cross Island Trail from Oyster Cove to the Chesapeake Bay, Romancoke and Long Point Rd. Convenient for dog walking, biking, jogging, etc. Walk to 5 restaurants. Only 20 minutes to Annapolis by car or a 30-minute boat ride to St. Michael's for lunch and shopping. Enjoy a round of golf at Blue Heron executive course or Queenstown championship course. Your dream house awaits you!

1107 Oyster Cove Dr, Grasonville

Listing courtesy of Star Realty. Contact:

201 Switchgrass Way Unit 34, Chester
$835,000
3 Beds ⋅ 3 Baths
Enjoy breathtaking Chester River views from this move-in-ready waterfront condo at Four Seasons at Kent Island. Meticulously maintained by its original owners as a 2nd home, this beautifully customized three-bedroom, two-and-a-half-bath condo combines elegant, low-maintenance living with the exceptional amenities of a premier 55+ community. Enjoy added convenience with Wi-Fi-enabled appliances in both the kitchen and laundry room, all easily controlled through a connected app. The home also features a Wi-Fi-enabled thermostat for convenient remote control of the heating and cooling system. Five-year extended warranties are included on most major appliances. The light-filled, open-concept floor plan features luxury vinyl plank flooring, recessed lighting, and expansive windows that bring the river views into nearly every room. A cozy electric fireplace anchors the spacious living room, which flows seamlessly into the dining area and gourmet kitchen—an inviting setting for everyday living and entertaining alike. Custom electric blinds in the living area and kitchen add comfort and convenience. The kitchen offers stainless steel appliances, a gas cooktop, white cabinetry, and generous counter space. Step outside to the expansive waterside balcony for morning coffee, spectacular sunsets, and views of boats gliding along the river. The waterfront primary suite is a private retreat, with direct balcony access, a spacious sitting area, two walk-in closets, and custom electric blackout and day shades. Its elegant en-suite bath features dual vanities and a large walk-in shower. Two additional bedrooms offer flexible space for guests, a home office, or hobbies, with pull-down blackout shades for privacy. Thoughtful extras include a beautifully crafted built-in bar, a large laundry room, a dedicated storage room, and an attached one-car garage with a new speckled epoxy floor. Residents enjoy a resort-style array of amenities, including indoor and outdoor swimming pools, a fitness center, clubhouse, library, billiards room, hot tub, bocce ball, pickleball and tennis courts, picnic areas, tot lots, and a community pier overlooking the Chester River. Just minutes from shopping, dining, golf, marinas, and the Chesapeake Bay Bridge, this exceptional home offers a wonderful opportunity to enjoy waterfront living and the best of the Eastern Shore.

201 Switchgrass Way Unit 34, Chester

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

620 Baxter Rd, Sudlersville
$579,900
3 Beds ⋅ 3 Baths
PRICE IMPROVEMENT! Welcome to the Country — and Get Ready to Enjoy Your New Home This Fall! This beautifully maintained custom-built 3-bedroom, 2.5-bath home is perfectly situated on 3.34 picturesque acres with mature landscaping, privacy, and an incredible amount of space to live, work, entertain, and enjoy the outdoors. With a price improvement, this is the perfect opportunity to settle in this fall, enjoy backyard fires under the stars, and be home in time to celebrate the holidays in your new country retreat! Start your mornings on the inviting front porch or unwind on the cozy screened rear porch while taking in the peaceful surroundings. The beautifully updated interior features a completely renovated kitchen with white cabinetry, quartz countertops, top-of-the-line stainless-steel appliances, and stunning luxury vinyl plank flooring throughout. Fresh interior paint in Sherwin-Williams Agreeable Gray creates a warm, modern, timeless feel. The spacious primary suite offers an oversized walk-in closet and a luxurious private bath with a spa tub and separate shower. The partially finished basement provides additional heated and air-conditioned living space that can easily be used as a recreation room, home gym, office, hobby area, or additional sleeping space. Recent updates and improvements include: Newer 3.5-ton HVAC system, New luxury vinyl plank flooring throughout, New well pump with continuous pressure system, Tankless water heater professionally serviced, Chimney professionally cleaned and serviced, Additional attic insulation for improved energy efficiency. Outside is where this property truly shines! A detached two-car garage is conveniently connected to the home by a breezeway. But the real showstopper is the impressive 30' x 60' detached building, offering an incredible amount of space and flexibility. With 220-volt electric service, a workshop, storage loft, office, and expansive gathering/party room, this building opens the door to endless possibilities. Create the ultimate workshop, operate a home-based business, set up a hobby or creative studio, store vehicles and equipment, host family and friends, or create the perfect space for celebrations and gatherings. Whether you're a car enthusiast, craftsman, entrepreneur, hobbyist, or simply need room to spread out, this exceptional building provides the versatility that's hard to find. Imagine spending fall evenings around a backyard fire, hosting friends and family in the spacious gathering room, enjoying the privacy of your own acreage, and then welcoming everyone back for the holidays. There is room here to make memories — and room for your passions, hobbies, work, and future plans. Conveniently located just 18 miles from Chestertown, Centreville, Dover, and Middletown, this one-of-a-kind property offers the perfect blend of peaceful country living, privacy, space, and accessibility. If you've been waiting for the opportunity to own a property where you can truly live, work, entertain, and enjoy the country lifestyle — now is the time to take a look. With the price improvement and so much to offer, this exceptional property is one you won't want to miss!

620 Baxter Rd, Sudlersville

Listing courtesy of Taylor Properties. Contact:

117 Flycatcher Way, Chester
$995,990
3 Beds ⋅ 4 Baths
The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio that extends your living space outdoors. Thoughtful design details—such as barn doors, crown molding, and a custom feature wall—add character and craftsmanship throughout. As an added bonus, all model home furniture is included, offering a seamless move-in-ready experience. The beautifully appointed kitchen features a range, single oven, microwave, range hood, dishwasher, French door refrigerator, stylish pendant lighting, and a coordinating tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a fresh, integrated design. LVP flooring extends across the main level for durability and style, with tile in all full baths and carpet in Bedrooms 2 and 3 for added comfort. The owner’s bath offers a spa-inspired shower with a built-in seat, handheld shower wand, and double sinks—creating a relaxing and functional daily retreat. For a full list of included features, please contact our sales representatives. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

117 Flycatcher Way, Chester

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

209 Harrier Way, Chester
$737,900
4 Beds ⋅ 3 Baths
LESS MONEY OUT OF YOUR POCKET!!! With an accepted contract by 9/30/26 - the sellers are offering up to $7500 toward your closing costs or to use toward a rate buydown if you're financing your purchase! If you're looking for the ease of primarily one-level living with flexible space for guests and hobbies, 209 Harrier Way offers the best of both worlds.*** Barely lived in and offering over $75,000 in builder upgrades, this home still feels like new, allowing you to move right in without the wait or additional costs of new construction (i.e. transfer tax split, etc). Designed for easy everyday living, the Simone model offers the convenience of having the majority of the home's daily living spaces on the main level. The gourmet kitchen, dining and living areas, screened porch, primary suite, second bedroom, office, full bath, and laundry are all thoughtfully located on the main floor. The stunning gourmet kitchen features crisp white cabinetry, a large center island, stainless steel appliances, wall oven/microwave combination, and propane gas range, flowing seamlessly into the light-filled dining and living areas. The living room is anchored by a cozy stone fireplace, while the screened porch provides a relaxing place to enjoy your morning coffee or unwind. The main-level primary suite features tray ceilings and a spa-inspired bath with dual vanities, a large walk-in shower, and an expansive walk-in closet. Upstairs, you'll find flexible bonus space including a spacious loft, two additional bedrooms, and a full bath, perfect for visiting family, hobbies, entertaining, or simply having extra space when you want it. **It's additional space when you need it, without requiring stairs for your everyday living.** The attached garage adds convenience and storage. Beyond the home, enjoy a resort-style lifestyle with incredible amenities including a 23,000-square-foot clubhouse, fitness center, indoor and outdoor pools, billiards, tennis and pickleball courts, community pier, outdoor bar, fire pit, and a full calendar of social activities. The nearby Cross Island Trail is perfect for walking, running, or biking, and you're just minutes from shopping, dining, and everything Kent Island has to offer.

209 Harrier Way, Chester

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

113 Bentons Pleasure Rd, Chester
$829,000
4 Beds ⋅ 3 Baths
OPEN SUNDAY OCT 4 11am-1:00 pm--A must see home! NEW LIST PRICE Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and eat in breakfast area. Formal Dining room, main level fourth bedroom or office with half bath and exterior entrance, perfect for occasional client or guest. Large 17x13 1st level Living Rm with hardwoods & display center. Inside entrance to the four car garage with additional built-in storage & shelving! Upper level primary bedroom suite featuring 2 walk in closets, gorgeous primary bath with double vanity, huge walk in shower, quartz counters and trim, jetted soaking tub and wainscoting & chair rail finishes. Bedroom #2 w/walk in closet & double entry full bath. Bedroom #3 w/walk in closet, ceiling fan and upper deck access. Upper level laundry area with washer, dryer, shelving and deep sink. Exterior features include 1 Acre lot, beautiful pool with adjoining deck, screen porch, patio w/hot tub and garden shed. Front porch with covered sitting area. Oversized driveway w/side parking area perfect for boat or RV storage. Exterior audio & video system currently in use but not included in the sale. Your super opportunity for a wonderful home!

113 Bentons Pleasure Rd, Chester

Listing courtesy of Cummings & Co. Realtors. Contact:

106 Pixie Ct, Grasonville
$599,900
5 Beds ⋅ 3 Baths
Please remove shoes or use shoe covers provided! Welcome to the rarely-available upgraded Hudson model at Perry's Retreat located at 106 Pixie Court. This beautiful unit offers the perfect blend of space, comfort, and modern design on a PREMIUM LOT. This home presents a rare opportunity to own one of the community's most desirable models in a cud-de-sac. The main level features an open concept design that seamlessly connects the kitchen, dining, and living areas, creating an ideal layout for both everyday living and entertaining. A private office with French doors provides the perfect work from home space, while an additional ensuite bedroom on this level offers endless possibilities as a guest room, or hobby space. The upgraded kitchen serves as the heart of the home, showcasing quartz countertops, stainless steel appliances, upgraded backsplash, additional wall oven, and a large island overlooking the spacious living room. Luxury vinyl plank flooring in most of the main level adds both style and durability. Upstairs, the spacious primary suite offers a relaxing retreat with a tray ceiling, two oversized walk-in closets, and a beautifully appointed en-suite bathroom featuring dual vanities, private water closet, and linen closet. Three additional bedrooms, a full bathroom with double sinks, and a convenient upper-level laundry room complete the second floor. Outside, enjoy a backyard that creates a setting for relaxation and entertaining. Community amenities include a playground, open green space for neighborhood events. Conveniently located just minutes from Route 50, residents enjoy easy access to Kent Island, Annapolis, Easton, St. Michaels, Oxford, Tilghman Island, Baltimore, and Washington, D.C. Directly across from the community, the Chesapeake Bay Environmental Center offers hiking trails, kayaking, wildlife viewing, educational programs, and summer camps, allowing you to fully embrace the Eastern Shore lifestyle. Professional photos coming soon!

106 Pixie Ct, Grasonville

Listing courtesy of HomeSmart. Contact:

116 Reeand Ln, Church Hill
$399,000
3 Beds ⋅ 3 Baths
Sellers willing to contribute seller help to fund a buyer’s 2-1 interest rate buydown! Buyers get the benefit of a lower mortgage payment the first 2 years! Dependant upon offer amount and or an "as-is" offer. Welcome home to this beautifully maintained Colonial nestled in the desirable Meadows community of Church Hill. Ideally located between historic Chestertown and Centreville and within the sought-after Queen Anne's County School District, this home offers the perfect blend of comfort, convenience, and timeless style. Step inside through the impressive two-story foyer that welcomes you into a bright and inviting floor plan. The spacious primary suite serves as a private retreat, complete with a, separate shower, and relaxing soaking tub. The home has been exceptionally well cared for and features numerous updates, including a newer roof and HVAC system, providing peace of mind for years to come. New HVAC system installed and serviced by Dixieland energy January 2025, operated by Nest technology. New Roof in July 2025 installed by Economy Roofing with GAF Timberline HDX Lifetime Shingles. New 16x12 Trex Deck with a large poured concrete patio installed in 2024-2025. The partially finished full basement offers endless possibilities with plenty of room for a recreation area, home gym, office, or additional storage. Outside, you'll fall in love with the beautifully landscaped backyard oasis—perfect for entertaining, summer barbecues, or simply relaxing after a long day. Square footage including basement is roughly 2700 sq feet. With its outstanding condition, thoughtful updates, attached garage, and prime location just minutes from shopping, restaurants, and easy access to Route 301, this is a home that truly checks all the boxes. Schedule your private showing today and experience everything 116 Reeand Lane has to offer! Some photos have had personal items removed and have been staged with AI.

116 Reeand Ln, Church Hill

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

200 Ackerman Dr, Stevensville
$589,999
4 Beds ⋅ 3 Baths
Experience coastal living at its finest in this stunning 2024-built home located in the sought-after Romancoke community, just steps from the Chesapeake Bay. This beautifully appointed 4-bedroom, 2.5-bath home offers the perfect combination of modern design, comfort, and convenience. The spacious open-concept floor plan is ideal for entertaining, featuring seamless flow between the living, dining, and kitchen areas. High-end custom window blinds add a touch of elegance throughout, while the fully fenced backyard creates the perfect private retreat for relaxing, hosting gatherings, or enjoying time with family and pets. Perfectly situated on a quiet private road, this home offers a peaceful setting with easy access to the bay, making it ideal for boating, fishing, kayaking, or simply enjoying breathtaking waterfront sunsets. Connected to public sewer and built in 2024, you'll enjoy the benefits of newer construction with the peace of mind that comes with modern systems and finishes. Don't miss this opportunity to own a like-new coastal retreat in one of Kent Island's most desirable waterfront communities!

200 Ackerman Dr, Stevensville

Listing courtesy of Rise Real Estate, LLC. Contact:

1130 Old Love Point Rd, Stevensville
$1,900,000
3 Beds ⋅ 2 Baths
Steeped in history and surrounded by the timeless beauty of Maryland’s Eastern Shore, 1130 Old Love Point Road presents a once-in-a-generation opportunity to own an extraordinary family farm in the heart of Kent Island. Spanning approximately 36.73 acres, this remarkable property blends agricultural heritage, historic character, and exceptional future potential in one of the Shore’s most storied locations. At the center of the property sits an historic Victorian farmhouse dating to circa 1896, recognized by the Maryland Historical Trust as a historically contributing structure representative of the classic 19th-century Delmarva farmhouse. The home and grounds reflect generations of stewardship and offers tremendous opportunity for its next generation renovation, rehabilitation and future development prior to occupancy. Old Love Point Road itself carries a rich and fascinating history. Before the Chesapeake Bay Bridge connected Maryland to the Eastern Shore, Love Point served as one of the principal gateways to the Shore. Ferries, steamships, and rail lines once brought travelers from Baltimore and Annapolis to Kent Island, where they continued eastward across Maryland and Delaware. Love Point became known as a romantic waterfront destination and transportation hub, welcoming visitors arriving by ferry and the historic Queen Anne’s Railroad. The property’s location captures the spirit of that history while offering exceptional convenience to today’s modern traveler. Situated just minutes from Route 50 and the Chesapeake Bay Bridge, the farm offers easy access to Annapolis, Washington D.C., Baltimore, and the Delaware beaches while maintaining the peaceful charm of Eastern Shore living. Currently farmed and designated as prime farmland, the property is ideally suited for a gentleman’s farm, equestrian estate, vineyard, winery, agritourism venue, or luxury country retreat. The Development Analysis Report identifies a winery as one of the site’s most favorable and viable uses, noting that agritourism operations such as vineyards and wineries are specifically encouraged within Queen Anne’s County’s future agricultural economy plans. In addition to its agricultural and lifestyle appeal, the property, perhaps most importantly, offers substantial long-term development potential. Located within the County’s Suburban Estate zoning district and designated growth area, the site may support future residential subdivision opportunities, including large-lot estate development, clustered single-family communities, multifamily concepts, or additional residential lots under current moratorium guidelines. Whether envisioned as a private family compound, vineyard and winery destination, legacy investment, or future development opportunity, 1130 Old Love Point Road represents a rare chance to own a meaningful piece of Maryland’s Eastern Shore history — where the past, present, and future converge along one of Kent Island’s most iconic roads.

1130 Old Love Point Rd, Stevensville

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

2200 Bennett Point Rd, Queenstown
$675,000
4 Beds ⋅ 2 Baths
Welcome to this beautifully maintained one-level rancher, perfectly situated on a private 1-acre lot. Offering 2,441 square feet of comfortable living space, this home provides 4 bedrooms, 2 full baths, and has an inviting open floor plan designed for everyday living and entertaining. Thoughtful architectural details, including coffered ceilings and heavy crown molding, add character and elegance throughout the main living areas. The spacious living room is anchored by a fireplace with a wood-burning insert, creating a warm and welcoming atmosphere. The well-appointed kitchen offers abundant cabinet and counter space and opens seamlessly to the main living areas. The dining area is spacious, ideal for hosting family and friends. A large four-season room, complete with heating and cooling, provides additional year-round living space and overlooks the lovely backyard. Step outside to enjoy the expansive deck and pergola-covered seating area, perfect for relaxing or entertaining. The fully fenced backyard offers plenty of room for outdoor activities while maintaining a sense of privacy. A detached two-car garage features a heated and cooled bonus room above, ideal for a home office, gym, hobby room, or additional flex space. Major improvements completed within the past five years include a newer HVAC system, roof, gutters, and kitchen updates, providing added value and peace of mind. This exceptional property combines the convenience of one-level living with modern updates, versatile spaces, and a peaceful setting—ready for you to call it home.

2200 Bennett Point Rd, Queenstown

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

4 Prospect Bay Dr W, Grasonville
$1,199,000
5 Beds ⋅ 3 Baths
Classic Colonial Overlooking the Golf Course in Prospect Bay. BRAND NEW ROOF! Welcome to this beautifully maintained brick-front Colonial, perfectly positioned with picturesque golf course views in the sought-after Prospect Bay community. Filled with natural light from oversized windows, the open floor plan offers the perfect balance of comfortable everyday living and elegant spaces for entertaining. The home features four spacious bedrooms upstairs, plus a first-floor office or optional fifth bedroom, making it ideal for guests, multi-generational living, or working from home. Hardwood floors, two fireplaces, a formal dining room, and generously sized living spaces create timeless appeal throughout. The spacious primary suite offers a peaceful retreat with a walk-in closet and private bath. A three-car garage provides ample storage and convenience. Step outside to your private backyard oasis, where a heated swimming pool, expansive deck with a covered awning, and sweeping golf course views create the perfect setting for relaxing or entertaining. Enjoy watching golfers from your backyard while soaking in the peaceful surroundings. Extra large driveway, fresh paint, all upgraded bathrooms are just some of the upgrades besides the brand new roof. Living in Prospect Bay means enjoying resort-style amenities, including an 18-hole championship golf course, clubhouse with members-only restaurant and bar, marina with boat launch, swimming pool, tennis and pickleball courts, playground, and a full calendar of year-round social events. This exceptional home offers the perfect blend of classic elegance, modern comfort, and an unbeatable lifestyle.

4 Prospect Bay Dr W, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

111 Marshgrass Way Unit 41, Chester
$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. Residents enjoy an exceptional resort-style lifestyle with amenities that include indoor and outdoor swimming pools, a fitness center, clubhouse, library, billiards room, hot tub, Bocce Ball, pickleball and tennis courts, picnic areas, tot lots, and a community pier overlooking the Chester River. Ideally located just minutes from shopping, dining, golf, marinas, and the Chesapeake Bay Bridge, this exceptional waterfront residence offers the perfect blend of luxury, convenience, and carefree Eastern Shore living.

111 Marshgrass Way Unit 41, Chester

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

102 Boatswain Way Unit 2943, Chester
$909,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, 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.

102 Boatswain Way Unit 2943, Chester

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

102 Boatswain Way Unit 2932, Chester
$809,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, 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.

102 Boatswain Way Unit 2932, Chester

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

134 Richard Ingle Way, Chester
$749,000
4 Beds ⋅ 4 Baths
Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Built in 2017, this exceptional residence enjoys unobstructed pond views from the welcoming covered front porch, where you can relax while watching blue herons and other native wildlife. Perfectly positioned just one block from the community's exceptional waterfront amenities, including the Chester River, clubhouse, pool, fitness center, kayak launch, fishing pier, and waterfront pavilion, this home offers the perfect blend of luxury, convenience, and the relaxed lifestyle of Maryland's Eastern Shore. Step inside to discover a bright, thoughtfully designed floor plan where beautiful flooring flows throughout the main level and abundant natural light fills every room. Designed for both everyday living and effortless entertaining, the main level offers exceptional versatility with a spacious flex room that is ideal as a home office, den, sitting room, or additional living space, along with a convenient powder room for guests. The heart of the home is the expansive open-concept living area, where the spacious family room, dining area, and beautifully appointed kitchen come together seamlessly. The kitchen features a large center island with abundant seating and workspace, while the family room is highlighted by a beautiful gas fireplace. Just beyond, the brand-new screened porch opens to your own private backyard oasis featuring a beautifully landscaped paver patio, a tranquil ornamental pond with a cascading waterfall, full privacy fencing perfect for pets, and an irrigation system to keep the grounds looking their best. Designed for the ease of first-floor living, the main level features a spacious primary suite privately situated at the rear of the home. The luxurious ensuite bath includes a relaxing Jacuzzi soaking tub, while a second main-level bedroom offers its own private full bath, making it ideal for guests or multigenerational living. The staircase to the upper level is thoughtfully tucked toward the rear of the home, enhancing the home's functional layout. Upstairs, you'll find two generously sized bedrooms and a beautifully appointed full bath, providing comfortable accommodations for family and guests. Completing the home is a spacious rear-entry two-car garage with plenty of room for parking and storage, plus a custom-built workspace perfect for DIY enthusiasts, hobbyists, or woodworking projects. An approximately four-foot-high conditioned crawl space with interior access provides exceptional additional storage. Recent improvements include a brand-new HVAC system, brand-new screened porch, one-year-old oven, and new washer and dryer, allowing you to move in with confidence. Residents of Gibson's Grant enjoy resort-style amenities, including a clubhouse, outdoor pool, fitness center, waterfront pavilion, kayak launch, fishing pier, water access, and direct access to the Cross Island Trail. Tucked behind a peaceful nature preserve just off Route 50, this sought-after waterfront community offers the perfect balance of tranquility and convenience. Located just moments from the Chesapeake Bay Bridge, the home provides an easy commute while placing you minutes from waterfront dining, marinas, shopping, parks, and local entertainment. Beautifully maintained, thoughtfully updated, and ideally located in one of Kent Island's most desirable neighborhoods, this exceptional home offers the perfect opportunity to embrace luxury coastal living on Maryland's Eastern Shore. Schedule your private showing today! Mortgage savings may be available for buyers of this listing.

134 Richard Ingle Way, Chester

Listing courtesy of Redfin Corp. Contact: