Refine Search
Map
Sort by
204 Long Point Rd, Stevensville
$390,000
3 Beds ⋅ 2 Baths
Nestled within the Water Privileged Romancoke on the Bay Community, this ranch-style home offers a unique blend of affordability and comfort. With its proximity to the community waterfront on the Chesapeake Bay, residents can enjoy stunning views, boating, and fishing. The community's amenities includes a boat ramp, clubhouse, playground, picnic area, and more. The property's convenient location near the Romancoke Pier and the South Island Trail provides lots of opportunities for outdoor recreation. The expansive front porch is ideal fo relaxation, while the interior includes over 1,400 square feet of living space, including three bedrooms. The primary bedroom features a full bathroom and walk-in closet. Additional highlights include a large shop with electric, recently encapsulated crawl space, and fenced backyard. Square Footage based on Public Records, Buyer to Confirm,

204 Long Point Rd, Stevensville

Listing courtesy of Rosendale Realty. Contact:

Selling Office: Coldwell Banker Realty.

116 Talbot Rd, Stevensville
$390,000
3 Beds ⋅ 2 Baths
Come visit this beautifully maintained rancher tucked away in the sought-after Kent Island Estates community. This charming home sits on nearly half an acre of flat functional land. With plenty of room to relax and entertain, the property offers space for a garden, pool, patios, you name it! Just a few blocks away, enjoy easy access to community beaches, scenic parks, playgrounds, the South Island Trail, and the Romancoke Fishing Pier, putting the very best of the Kent Island lifestyle right at your fingertips. Car/Boating enthusiasts will appreciate the convenience of two driveways, and a newly built custom garage perfect for storing all your toys. Spend the day out on the bay after launching from nearby Matapeake Landing, then return home to grill your fresh catch and unwind in the backyard. As the sun sets, sit back, stargaze, and take in the calm—this is what Island Life is all about. Don’t miss this rare opportunity to own a slice of paradise. Schedule your private showing today!

116 Talbot Rd, Stevensville

Listing courtesy of Real Broker, LLC - Annapolis. Contact:

Selling Office: Unrepresented Buyer Office.

317 Melvin Ave, Grasonville
$390,000
4 Beds ⋅ 2 Baths
Price Improved ! Welcome to 317 Melvin Avenue in the peaceful community of Grasonville, MD. This charming 4-bedroom, 2-bath home offers over 2,100 sq. ft. of living space on nearly a half-acre lot—a wonderful blend of comfort, style, and value! Step inside to an open, inviting layout that flows effortlessly from room to room. The updated kitchen features stainless steel appliances, granite countertops, and a spacious center island that opens to the expansive family room. A sliding barn door adds character and leads to a versatile bonus room or home office. The primary suite includes a large walk-in closet and updated ensuite bath, while three additional bedrooms and another renovated full bath provide ample space for family and guests. A large mudroom adds everyday convenience. Outside, enjoy your 12' x 24' Kayak pool with an 8' deck—perfect for summer fun and entertaining. The fully fenced backyard offers plenty of room to play, relax, or garden. With no HOA, covenants, or restrictions, you have the freedom to make this property truly your own. Discover the laid-back Eastern Shore lifestyle and make 317 Melvin Avenue your next home!

317 Melvin Ave, Grasonville

Listing courtesy of Compass. Contact:

Selling Office: Clark & Co Realty, LLC.

106 Turpins Ln, Centreville
$389,900
3 Beds ⋅ 2 Baths
Back on the market at no fault of the seller, the buyer's home sale contingency fell through, creating an excellent opportunity for you to make it yours! Welcome to 106 Turpins Ln, a charming 3-bedroom, 2-bath home in the heart of historic Centreville, Maryland. This property offers the perfect blend of comfort, style, and location. Completely renovated in 2025, everything is brand new! Step inside to find an open layout with beautiful hardwood flooring throughout. The kitchen features granite countertops, stainless steel appliances, and a breakfast bar. The spacious primary suite features a private ensuite bathroom and double closets. All the bedrooms include generous closet space, and the layout is designed for modern living. Enjoy a low-maintenance yard and patio and an oversized 1–2 car garage—ideal for storage or workshop space. Located steps from restaurants, shopping, the library, parks, playgrounds, and a public landing for boating and water access. This affordable, move-in-ready home is in a prime walkable location, perfect for homeowners and small business owners. The property is zoned for residential and/or commercial use, offering a unique opportunity or investment potential. Don't wait—schedule a private showing today!

106 Turpins Ln, Centreville

Listing courtesy of Clark & Co Realty, LLC. Contact:

Selling Office: Compass.

300 Talbot Rd, Stevensville
$387,499
3 Beds ⋅ 1 Baths
Bright and modern home with an open layout and plenty of natural light. Features a fully updated kitchen with stainless steel appliances, white cabinetry, and subway tile backsplash. Highlights include new flooring, contemporary lighting, and a beautifully renovated bathroom. The exterior offers a large, level backyard with a private driveway and a spacious storage shed. Move-in ready and perfect for modern living.

300 Talbot Rd, Stevensville

Listing courtesy of Real Estate Professionals, Inc.. Contact:

Selling Office: EXP Realty, LLC.

7009 Bridgepointe Dr, Chester
$385,500
3 Beds ⋅ 2 Baths
Bridgepoint - This is a great end unit that is private and overlooking the pond with the fountain. The unit offers a first floor primary bedroom and bath. Open floor plan for entertaining and sunroom you will enjoy. Upstairs is two large bedrooms and a bath. Storage space in the attic. The one garage offers room for your car and some storage. Call today for your showing appointment.

7009 Bridgepointe Dr, Chester

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

Selling Office: RE/MAX Leading Edge.

251 Rings End Rd, Millington
$385,000
3 Beds ⋅ 1 Baths
Nestled along the banks of the Chester River in the historic waterfront town of Millington, this enchanting 1955 cottage offers a rare opportunity to embrace the beauty of Eastern Shore living. Steeped in tradition and situated on the original Rings End Farm property, this special home is rich with local history and timeless character. Surrounded by lush landscaping, mature trees, abundant wildlife, and sweeping river views, the property invites a lifestyle defined by nature, tranquility, and endless days on the water. Eagles soar overhead, herons wade along the shoreline, and the peaceful rhythm of the river creates an extraordinary natural setting in every season. Inside, timeless charm meets comfortable living with thoughtfully designed spaces that celebrate the surrounding landscape. The spacious kitchen features a sunlit breakfast room with large windows framing peaceful backyard and river views, while a separate dining room creates the perfect setting for intimate gatherings. An RO system under the kitchen sink provides added convenience and water quality. The inviting living room is filled with warmth and character, complete with a skylight and cozy wood-burning stove. A generous family room opens directly to an expansive brick patio, seamlessly blending indoor and outdoor living. Three comfortable bedrooms, a large laundry/mud room with side entrance and additional storage, and two substantial outbuildings provide both functionality and flexibility for everyday life and waterfront adventures. Recent improvements include a new well pump installed in 2025 and a new thermostat also installed in 2025, offering additional peace of mind. The true magic of the property unfolds at the water’s edge. Stroll down to your private pier and floating dock (5 foot MWL) where days are spent embracing the very best of waterfront living. Cruise the river by boat, launch a kayak or paddleboard, spend quiet mornings crabbing, or cast a fishing line into the Chester River, known for catfish, spot, sunfish, yellow perch, and other local catches. Whether enjoying an afternoon on the water or simply taking in the breathtaking sunsets from the pier, the river becomes an extension of everyday life and a constant source of recreation. The town of Millington adds to the charm, offering two public parks and a public community swim club complete with pool and tennis courts. Conveniently located to shopping and dining in both Millington and nearby, Chestertown, Middletown DE, the property also offers easy access to Route 301, connecting you effortlessly to Eastern Shore destinations, Wilmington in just about an hour, and Philadelphia in approximately 90 minutes. Whether you're seeking a peaceful weekend retreat or a year-round waterfront sanctuary, this remarkable property captures the essence of refined Eastern Shore living while honoring the history and heritage of the original Rings End Farm.

251 Rings End Rd, Millington

Listing courtesy of Northrop Realty. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

321 Front St, Crumpton
$385,000
3 Beds ⋅ 3 Baths
This one of a kind home in peaceful quiet Crumpton is waiting for you. The property is set on nearly one acre and the lush mature landscaping and large trees create a 3-season privacy screen that changes colors with the seasons. The property is partially fenced for kids and pets. Perennial gardens are a delight and there are garden areas for your veggies and and flowers. The home features a first floor open concept plan with a gas fireplace perfect for those chilly nights, a chef’s kitchen with stainless steel appliances, gas cooking, a half bath for guests and a generously sized separate laundry room with space for a pantry or other storage needs. The first floor primary suite is perfect for aging in place with a large bedroom, walk-in closet, and en suite bath featuring a double vanity, walk in shower and separate soaking tub. The second floor is home to two additional generously sized bedrooms, two walk-in closets and a shared bath with walk-in shower and separate soaking tub. Natural light abounds through the many windows with wide sills and the screened porch awaits your morning coffee and reading pleasure. The front porch is shaded by a mature planting. This home has been meticulously maintained and had a new roof installed in 2024 and a new well in 2025. The heating and AC are generated by an efficient 2-zone Bryant heat pump. This home is across the street from the Chester River on a low traffic lane and the newly refurbished public Crumpton boat landing and dock are a minute away. Shopping in Millington, Chestertown and Delaware are minutes away as is easy access to major highways. If you are searching for the Eastern Shore lifestyle in a quiet community that is close to all the amenities, look no further. This is the home for you.

321 Front St, Crumpton

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

1803 Chester Dr, Chester
$385,000
4 Beds ⋅ 2 Baths
Adorable rancher on Kent Island in the community of Harbor View! Featuring 4 beds, 2 baths, and private driveway. Enjoy the large fenced yard with deck, shed, and firepit. The living room has a cozy fireplace with wood stove insert. The primary bedroom has a private bath with tile and stand up shower. Updates include both bathrooms, updated windows, roof 2020. Close to Route 50 for easy access to the beaches or the Bay Bridge, trails, medical, restaurants, and shopping.

1803 Chester Dr, Chester

Listing courtesy of Keller Williams Legacy. Contact:

Selling Office: EXP Realty, LLC.

111 Dell Foxx Rd, Barclay
$385,000
3 Beds ⋅ 3 Baths
Escape to the tranquility of rural living with this delightful 3 bedroom, 2 bath property nestled on a sprawling 1-acre parcel. Located in the heart of the countryside, this inviting home is ideal for a permanent home or as a second home to enjoy everything the Eastern Shore of Maryland has to offer, such as hunting, fishing, boating, or just a peaceful getaway. The vaulted living area is spacious and accented by a wood stove that provides both a cozy ambiance and efficient heating during colder months. The living room opens to a new 2-level outdoor deck, as well as the kitchen, perfect for entertaining family and friends. The large kitchen has an overabundance of new granite countertops, plenty of cabinets, and an island. The perfect kitchen for multiple cooks, and maybe an even larger island! The laundry room is located directly off the kitchen with access to the back yard, and to the garage. Perfect for extra storage or as a mudroom. The home features three nice sized bedrooms, including a primary suite with a full bathroom and dual closets. The property has plenty of room for a garden, boat or RV storage, or just sit back and enjoy the serenity of country living. Located just 1.5 miles from Route 301, the location is perfect for commuting north to Wilmington or Philadelphia, or head south to Annapolis and Washington DC.

111 Dell Foxx Rd, Barclay

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

Selling Office: Doug Ashley Realtors, LLC.

2644 Cecil Dr, Chester
$382,000
3 Beds ⋅ 2 Baths
Welcome to this Harbor View home offering approximately 1,108 square feet of comfortable, updated, one-level living on a spacious 1/3 ac lot. The backyard is fully fenced and ready for pets, play, and entertaining, with a long driveway and double gates for easy access. Enjoy outdoor living with a deck and an inflatable hot tub in the backyard that is available to convey. Inside, the layout is both functional and private, featuring three bedrooms and two full baths. The primary bedroom is generously sized and includes an en-suite bath, thoughtfully positioned on the opposite side of the home from the two additional bedrooms and the second full bath. Well-maintained laminate flooring runs through the main living areas, while the two additional bedrooms offer wall to wall carpet for extra comfort. The eat-in kitchen is bright and welcoming with updated appliances in 2023 and plenty of space for everyday meals. Major improvements provide peace of mind, including a new roof with a transferable lifetime warranty, new siding, gutters, and downspouts, plus added attic insulation and new windows with screens throughout, all completed in 2024. Additional updates include a newer dryer, ceiling fans installed in 2022, a water conditioner, and an HVAC system replaced in 2020. Conveniently located with quick access to Route 50 for an easy commute to Baltimore and Washington, DC, and just minutes to the Bay Bridge. The Harbor View community pavilion and playground, plus nearby everyday conveniences like dining, fitness options, and a local bakery, add even more value to this sought after neighborhood. Move-in ready and packed with upgrades.

2644 Cecil Dr, Chester

Listing courtesy of Realty Navigator. Contact:

Selling Office: Coldwell Banker Realty.

8 Queen Victoria Way, Chester
$382,000
2 Beds ⋅ 3 Baths
Beautifully upgraded 2.5 story townhouse ideally located directly across from the community marina and close to the clubhouse, offering exceptional convenience for boat owners and resort style living. The main level features a bright open living area with ceramic flooring that complements the home’s coastal style and blends seamlessly with the wood-burning fireplace. Sliding doors open to a private patio backing to common areas, creating a peaceful outdoor retreat. The kitchen has been updated with granite countertops, new stainless steel appliances, and a functional layout designed for both everyday living and entertaining. The second level offers two bedrooms and two full baths with vaulted ceilings and skylights throughout. The primary bedroom features an updated en suite bath, private balcony access, and direct access to a spacious loft, ideal for a home office, guest area, or additional living space. The second bedroom also offers vaulted ceilings, skylights, a private balcony with limited marina views, and convenient access to the full hall bath. A laundry area with a new combination washer and dryer is located on this level for added convenience. Sellers have replaced both balconies, and the roof was replaced in recent years with 30 year architectural shingles. Select furniture may be available upon request. Queens Landing is a waterfront condominium community on Kent Island offering a clubhouse, swimming pool, fitness center, pickleball, tennis and racquetball courts, and a community marina. Shopping, dining, and major routes are minutes away, with easy access to Annapolis, Baltimore, and Washington DC. This property is well suited as a primary residence, weekend escape, or low maintenance coastal retreat.

8 Queen Victoria Way, Chester

Listing courtesy of Realty Navigator. Contact:

Selling Office: RE/MAX Executive.

106 Utah Rd, Stevensville
$381,400
3 Beds ⋅ 2 Baths
This is an Estate sale and selling all "as is." Seller in process of removing some items but some household contents will remain. Priced well for a quick sell! Property overall has been well taken care of. Andersen windows and thermal doors, hardwood floors in kitchen area, separate laundry room. The fenced rear yard has a detached screened gazebo and a shed. There is an outside entrance to a deck from the kitchen area. Three car garage and off street parking. Three blocks to the Chesapeake Bay and a Community members only small beach area. Close to several county boat ramps and park areas. A road maintenance fee is $40.00 per year and the sewer fee is $300.00 per quarter.

106 Utah Rd, Stevensville

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

Selling Office: Coldwell Banker Realty.

115 Watson Rd, Centreville
$380,000
4 Beds ⋅ 3 Baths
Charming 3-story Farmhouse offers the convenience of downtown living & public amenities while enjoying a peaceful rural setting just one block from the Corsica River Wharf. This home is full of warmth & timeless character. Beautiful Heart of Pine hardwoods on the main level with visible square head nails! The Foyer leads into the spacious Living Room, featuring one wall of built-in bookcases, a gas FP accented with custom hand-pressed clay tiles and beautiful mantle handcrafted years ago by the owner’s Father. The LR opens into the Family Room or formal Dining Room, with a wood burning FP (with smoke guard), chimney cabinet on the left side, wall sconces, a beamed ceiling with 3 light prisms from the BR above that add unique character. This room also provides access to the Kitchen, Breakfast Room, and a rear staircase leading to a second-floor bedroom. Adjacent to the FR & Kit is a Breakfast Room with built-in hutch and outside entrance to the side yard. The main-level full bath, accessible from both the Breakfast Room and Foyer, features a large shower and tiled flooring. The Kitchen blends charm & functionality with a large porcelain sink, a convection gas Samsung range, recessed lighting, a wood ceiling, included island and 2 apartment-sized refrigerators, elevated on a wood platform with additional storage underneath. There are open shelves to the right of the Kitchen window and a cabinet below which is perfect for your sheet pans. Just a few steps down—where the top step lifts for hidden storage—you’ll find the mud/laundry room with exterior access to the driveway side of the home. The backyard includes a shed (as-is) and a patio for your enjoyment. The main staircase leads to the owner’s bedroom on the 2nd floor, is quite spacious and connects to the 2nd bedroom which was actually being used as a dressing room. The full bath is located off this room (shower has concrete floor), as well as three closets (top of the closets are cedar), the 2nd floor Sunroom/Office, a staircase to the FR/DR below and a staircase to the 4th BR on the 3rd level. The main staircase leads to the 3rd floor and 3rd bedroom. On this level is a half-bath. Three of the four bedrooms do not have closets. From the front of the home there are limited views of the Corsica River. The lot is .33 acre and has an extended driveway for ample off street parking. This home offers historic charm, handcrafted details and an ideal location!

115 Watson Rd, Centreville

Listing courtesy of RE/MAX Associates - Newark. Contact:

Selling Office: Benson & Mangold, LLC.

12 Queen Anne Way Unit J, Chester
$379,900
1 Beds ⋅ 2 Baths
Enjoy waterfront living in the sought-after Queens Landing community! This Mediterranean style 1-bedroom, 1.5-bath end unit condo offers a unique layout with beautiful water views and multiple outdoor spaces designed to make the most of the setting. The first-level primary bedroom and full bath allow for convenient main-level living. The upper-level loft adds valuable flex space with a wood-burning fireplace, skylights, and an abundance of natural light making it the perfect space for a home office, sitting area, guest space, or cozy retreat. Step outside and choose your view, from the garden-style front patio to the waterside patio out back or the upper-level balcony overlooking the water. With inviting indoor spaces, plenty of natural light, and multiple places to relax outdoors, this condo offers an easy, low maintenance, Eastern Shore lifestyle in a beautiful waterfront community.

12 Queen Anne Way Unit J, Chester

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Selling Office: RE/MAX Leading Edge.

2645 Cox Neck Rd, Chester
$379,900
3 Beds ⋅ 2 Baths
Welcome to 2645 Cox Neck Road, a move-in ready home in the desirable Harbor View Community of Chester. Offering 3 bedrooms, 1.5 baths, and situated on a spacious .34-acre lot, this well-maintained property combines comfort, convenience, and is priced to sell. Inside, you'll find a bright and inviting floor plan featuring a kitchen with a stylish tile backsplash, ample cabinetry, and luxury vinyl plank flooring. Thoughtfully maintained and updated over the years, this home offers peace of mind with a roof replaced within the last five years, replacement windows, siding, storm doors, and sliding glass door, as well as a recently replaced well pressure tank. Fresh interior paint and included appliances, including the washer and dryer, make moving in easy. Outdoor living is equally appealing with a charming front patio perfect for morning coffee and a large rear patio ideal for entertaining, grilling, or relaxing with family and friends. The beautifully maintained yard offers plenty of space for gardening, outdoor activities, or simply enjoying the outdoors. Two storage sheds provide ample room for tools, lawn equipment, and recreational gear. Located just minutes from Kent Island's popular restaurants, shopping, marinas, parks, and the Cross Island Trail, this home offers convenient access to everything the Eastern Shore lifestyle has to offer. Commuters will appreciate being less than 10 minutes from the Chesapeake Bay Bridge, while Harbor View residents enjoy a strong sense of community with neighborhood gatherings, holiday celebrations, yard sales, and other neighborhood events throughout the year. Whether you're searching for your first home, looking to downsize, or seeking a move-in ready property in a convenient Kent Island location, 2645 Cox Neck Road is an opportunity you won't want to miss.

2645 Cox Neck Rd, Chester

Listing courtesy of Compass. Contact:

Selling Office: Berkshire Hathaway HomeServices Homesale Realty.

1838 Sherman Dr, Chester
$379,000
3 Beds ⋅ 2 Baths
Nestled in the heart of Chester, Maryland on the beautiful Eastern Shore, this charming rancher offers comfort and convenience. Inside, a bright and inviting interior features neutral tones, modern finishes, and a functional layout ideal for everyday living. The light-filled dining area overlooks the backyard and flows into the galley kitchen, complete with stainless steel appliances, ample cabinetry, and an efficient workspace for meal preparation. The living room features durable LVP flooring and large windows that bring in abundant natural light. The primary bedroom includes direct access to a private en-suite bath, while two additional bedrooms offer flexibility for guests, a home office, or hobbies and share a conveniently located full hall bath. Sliding glass doors lead to a private deck overlooking the fully fenced backyard—perfect for relaxing, entertaining, or creating your own outdoor retreat with space for a garden, play area, or future pool. A one-car attached garage and private driveway provide off-street parking and additional storage space for tools, hobbies, or outdoor equipment. Located in a quiet, friendly neighborhood just minutes from Route 50, this home offers easy access to Annapolis, Kent Island, shopping, dining, and Chesapeake Bay waterfronts.

1838 Sherman Dr, Chester

Listing courtesy of Keller Williams Realty Centre. Contact:

Selling Office: Realty Navigator.

104 Iris Rd, Chestertown
$379,000
3 Beds ⋅ 2 Baths
Fully remodeled by reputable licensed contractor and subcontractors, 104 Iris has had a glow-up and is ready for showing! The clean lines of the new quartz countertops, the weight of soft golden Amerock hardware, Moen fixtures, Wolf two-tone shaker style cabinetry and well-appointed subway tile set the stage in the beautiful new Kitchen and bathrooms. Where a modern feel is met with the softness and simplicity of Neutrals as you move throughout the rooms that offer a timeless yet 2026 vibe! High-quality, low-maintenance LVP flooring has been installed in all high-traffic areas, along with carpet to quiet the bedroom spaces. Many new energy-saving features include architectural shingles, R38 insulation in the attic, crawl encapsulation, new HVAC unit & dehumidifier. Entry from the rear deck and hall to the large laundry area, is conveniently located adjacent to the hub of the home; the kitchen, where it balances aesthetics with functionality. Ample storage, Stainless steel appliances, an "L" shaped counter with seating area, giving all the practical space for your family's needs on one level. Electric has been modernized with new fixtures, premium touch mirrors, multiple remote-operated ceiling fans, USB outlets & recessed lighting. New doors, hardware and keypad entry locks, round out another set of upgrades. Solar lighting, fresh landscaping, and new treated decking enhance the exterior. It's large lot with mature trees, sits back off the road, in a quiet cul-de-sac, offering privacy, safety, and comfort. Backing up to acres of farmland, an extended outdoor living space great for entertaining also provides opportunity for viewing wildlife and sunsets alike. 104 Iris brings rural community living with the convenience of being close to town. Located in the Chester Harbor community in Queen Anne's county, where a 5-minute drive will have you centered in the town of Chestertown, known for its historic charm, river access, and boating opportunities, offering convenient commutes and amenities. Within walking distance of a private community water access and playground, this home has every detail ironed out and waiting for you! Easy to show! Join the Community Association, which is very reasonable and provides water access.

104 Iris Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: RE/MAX Executive.

101 Queen Anne Rd, Stevensville
$377,000
3 Beds ⋅ 2 Baths
Experience effortless one-level living in this charming home, perfectly situated on a desirable corner lot with a private driveway. Freshly painted throughout, the home features beautiful hardwood floors that add warmth and character to every room. Enjoy additional living space in the huge sunroom addition—perfect for relaxing, entertaining, or soaking in natural light year-round. A shed provides extra storage, offering both convenience and functionality. The flexible third bedroom can easily serve as a home office, guest space, or bonus room (note: no closet). Step outside and take in the lifestyle this location offers—just a short walk to the water with peaceful views. You’ll love being within walking distance to Romancoke Fishing Pier and Kayak Launch, ideal for fishing, kayaking, or enjoying a picnic by the water. This home combines comfort, convenience, and a scenic setting—don’t miss your chance to make it yours!

101 Queen Anne Rd, Stevensville

Listing courtesy of Maryland Residential Management Co. Contact:

Selling Office: Long & Foster Real Estate, Inc..

136 Hilltop Dr, Chestertown
$376,000
3 Beds ⋅ 2 Baths
Immaculate 3-bedroom, 2-bath home set on a breathtaking, oversized lot with exquisite mature landscaping and a truly picturesque setting. Surrounded by lush greenery and stunning trees, including a graceful willow, this property offers a serene, park-like atmosphere, with views from nearly every window resembling beautiful landscape artwork. Inside, the home features a bright, open floor plan designed for modern living. A spacious family room flows seamlessly into the generous kitchen, while a separate dining room remains open to the main living areas—perfect for everyday living and entertaining. The kitchen is highlighted by beautiful French doors leading to the back patio, offering easy access for cooking, grilling, and hosting—perfect for summer barbecues and outdoor entertaining. Palladium windows throughout enhance the home with natural light and showcase the spectacular views. The thoughtfully designed layout offers a private primary suite on one side of the home with its own attached bath. Just off the kitchen and near the primary bedroom is a separate laundry room for added convenience. Two additional bedrooms are situated on the opposite side and share a well-appointed full hall bath. Additional features include fresh paint throughout, a side-entry one-car garage, and an extra-large driveway providing ample off-street parking. Tucked away on a quiet cul-de-sac with no through traffic, this home offers a rare combination of privacy, beauty, and tranquility.

136 Hilltop Dr, Chestertown

Listing courtesy of Northrop Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

1150 Little Creek Rd, Chester
$375,000
3 Beds ⋅ 2 Baths
Start living the watermen dream! This charming home offers a thoughtfully designed layout with an open, airy flow and spacious rooms throughout. Situated on nearly one acre, you’ll enjoy both comfort and room to roam. The oversized living area is filled with natural sunlight streaming through the windows, creating a warm and inviting atmosphere. The first floor recently fresh coat of paint. Step outside to the private side deck — perfect for entertaining, hosting summer barbecues, or simply relaxing with friends and family. Featuring three bedrooms and 1.5 baths, this home includes a generously sized primary bedroom with vaulted ceilings and a walk-in closet. A storage shed provides extra space for tools and equipment, while the expansive yard offers endless possibilities for outdoor fun, gardening, or future enhancements. Bring your personal touches and make this home truly your own!

1150 Little Creek Rd, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Keller Williams Flagship.

217 Ackerman Dr, Stevensville
$375,000
3 Beds ⋅ 1 Baths
Welcome to this beautifully updated rancher in the sought-after Romancoke on the Bay community on Kent Island. This is where coastal charm meets modern comfort. Nestled on a rare double lot, this home offers space, privacy, and access to one of the area’s most loved water-oriented communities, complete with a waterfront clubhouse and community amenities. Inside, you’ll find fresh paint, LVP flooring, and a bright, inviting layout anchored by a white kitchen with updated cabinetry. The home features three comfortable bedrooms and a large, updated bathroom, perfect for easy one-level living. A screened-in porch extends your living space outdoors—ideal for relaxing evenings and coastal breezes. Recent upgrades provide peace of mind and efficiency, including a fully encapsulated crawlspace (2025), new HVAC (2025), additional attic insulation (2025), and a roof and siding approximately 5 years young. The detached building adds excellent storage or workshop potential. Enjoy an unbeatable location near the Kent Island Cross Trail, Romancoke Pier, and waterfront lifestyle amenities, all while being minutes from shopping, dining, and commuter routes. This move-in-ready home offers the perfect blend of updates, space, and coastal living—a true Romancoke gem you won’t want to miss.

217 Ackerman Dr, Stevensville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Chaney Homes, LLC.

2005 Stulltown Rd, Sudlersville
$375,000
4 Beds ⋅ 3 Baths
Beautifully updated Counrty Home on 1 Acre Near Sudlersville. This fully renovated 4 bedroom ,2.5 Bath Home offers the perfect blend of modern updates and peacful country living. The property offer a large yard and deattached garage. The home has a basement for added storage and living space. Home offer many recent upgrades and improvements , New roof, Hvac, ,Flooring ,Kitchen cabients and granite countertop and Spetic System. This home is move-in ready.

2005 Stulltown Rd, Sudlersville

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

Selling Office: Samson Properties of DE, LLC.

208 Blenny Ln, Chester
$374,900
4 Beds ⋅ 4 Baths
SO MUCH NEW! Welcome Home to this beautifully upgraded 4BR END UNIT Townhome with 2 full and 2 half baths, thoughtfully renovated this year from top to bottom! Step inside to find the main level that boasts NEW carpet and NEW LVP flooring, a NEW half bath, NEW paint, a spacious laundry room and a large bedroom that could be used as another family room, toy/game room, den space, home office and more! Get ready to be wowed by the rich walnut NEWLY stained hardwood flooring throughout the 2nd level where the living room, gas fireplace, NEW half bath and kitchen are located. The BRAND-NEW Kitchen finishes are sure to please with NEW white quartz counter tops, NEW SS Appliances, fresh neutral paint and white cabinetry! Upstairs hosts the huge Primary En-Suite, 2 more bedrooms all with NEW Carpet and another full bathroom with NEWLY Tiled shower, NEW toilet and NEW quartz sink! With three generous levels, a deck overlooking the pond, a cozy patio and a charming front porch, there’s space for everyone to relax and have their own space! Pull right into your own garage and your own driveway which makes life easy not to have to look for parking! The community offers fantastic amenities to enjoy like the inground and life-guarded pool, volleyball & tennis courts, fitness gym and direct access to the Cross Island Trail! Very close to the Castle Harbor Marina, many Beaches, Parks & Playgrounds and just a short stroll to local restaurants along the water's edge of the CHESTER RIVER! Sunsets are amazing! Condo living made easy with the Bayside HOA fee covering major exterior maintenance including the roof, deck rails, siding, exterior structural upkeep, landscaping, snow removal, road maintenance, trash, master insurance policy, professional property management, long term reserve funding and the list goes on!! Truly turn‑key living in an unbeatable location on the desired Eastern Shore of Maryland! Come see what Kent Island living is all about!

208 Blenny Ln, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Realty Navigator.

119 Watkins Rd, Grasonville
$374,600
3 Beds ⋅ 2 Baths
Welcome to this charming 3-bedroom, 1.5-bath Cape Cod, thoughtfully remodeled from top to bottom. Priced under appraised value, this home offers instant equity. With its traditional exterior, the interior has been beautifully updated and offers approximately 1,600 sq. ft. of comfortable living space. Major updates include a new roof and siding, luxury vinyl plank flooring, stainless steel appliances, and newly added central air conditioning. The newly updated kitchen opens to a welcoming main living area, centered around a beautiful fireplace that draws you in. Every detail has been carefully refreshed, creating a warm, move-in-ready home. The first-floor primary bedroom features a versatile sitting area, perfect for a nursery, office space, or just a cozy spot to curl up with a good book. Enjoy your morning coffee on the screened-in porch, entertain guests on the large deck, and relax in the fenced-in yard for privacy. For those who like to tinker or need extra space, there is a workshop in the backyard. Conveniently located just minutes from the Kent Narrows, this home provides easy access to shopping, hospitals, beaches, fishing, hunting, top restaurants, parks, boat landings, and marinas. Easy access to Route 50 and 301.

119 Watkins Rd, Grasonville

Listing courtesy of RE/MAX Advantage Realty. Contact:

Selling Office: Crown Homes Real Estate.

914 Petinot Pl, Stevensville
$374,000
2 Beds ⋅ 2 Baths
Cloverfields, A water privileged community with beach access, pool, clubhouse, and a dock. Only a few minutes from the Bay Bridge for the commuters. This 2 bed room 2 bath home is original and is in need of updating. This allows you to make this property updates that fit your tastes. Short distance to the water and marina.

914 Petinot Pl, Stevensville

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: RE/MAX Executive.

13513 1st St, Queen Anne
$374,000
This triplex backs to Roosevelt Park in the town of Queen Anne MD. Centrally located on the mid-shore 2 minutes from route 404, provides tenants the ability to reach, Easton in 15 min, Centreville in 15 min, Denton in 10 min and Annapolis in 30. As with most rental properties in the region occupancy has been near 100%. The building consists of a 1 bed 1 bath apartment in the rear of the building, a larger 1 bed 1 bath located on the second floor, and in the main portion of the house is a 2 bed 1 bath. The neighboring property is a duplex and is also for sale (13511 1st St). Call today for more details

13513 1st St, Queen Anne

Listing courtesy of Eastern Shore Real Estate, LLC. Contact:

Selling Office: Samson Properties.

719 Old Love Point Rd, Stevensville
$370,000
3 Beds ⋅ 1 Baths
Charming 3-Bedroom Rancher on a Spacious Double Lot Welcome home to this charming 3-bedroom, 1-bath rancher offering comfortable one-level living with plenty of space to make your own. Situated on a desirable double lot, this property features a spacious backyard with lots of room to play, relax, garden, or entertain family and friends. Inside, you’ll find beautiful hardwood floors throughout, a separate dining room, and a nice-sized kitchen with plenty of potential. A bonus space provides an opportunity to create whatever suits your needs—whether it’s a home office, hobby room, playroom, or additional living space. Seller has replaced the roof gutters and down spouts in addition the seller encapsulated the crawl space. Located in a wonderful community with an array of amenities, including a community pool, beach, boat launch, and more. A community marina is also available for a separate fee, making this an ideal location for those who enjoy spending time on the water. Conveniently located with an easy commute to the Bay Bridge, shopping, dining, and other everyday conveniences. This is a wonderful opportunity to own a home with a great yard, desirable community amenities, and plenty of potential—all at a reasonable price. Don’t miss your chance to make this home your own!

719 Old Love Point Rd, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Engel & Volkers Annapolis.

122 E Main St, Stevensville
$370,000
3 Beds ⋅ 2 Baths
122 E Main Street brings timeless colonial architecture to the heart of Historic Stevensville. Thoughtful updates, natural light, and generous room sizes create a home that feels both polished and comfortable. The kitchen is bright and efficient, offering extensive cabinet and counter space. A wide living and dining area anchors the main level, providing one cohesive space for gathering and entertaining. Upstairs, three full-sized bedrooms and two well-appointed baths ensure convenience and privacy, with storage in all the places you hope for. Sitting on a level corner lot with access from both Main Street and East Main Street, the property offers an easy, walkable lifestyle in one of Stevensville’s most beloved locations. With nearly 1,700 finished square feet, this home delivers a surprising amount of space in a setting that feels calm, welcoming, and distinctly “Stevensville.”

122 E Main St, Stevensville

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: Coldwell Banker Realty.

136 Allegany Rd, Stevensville
$370,000
3 Beds ⋅ 2 Baths
Adorable Coastal A-Frame in Romancoke on the Bay. Fall in love with this charming coastal-inspired A-frame nestled in the heart of Romancoke on the Bay on beautiful Kent Island! Bursting with character and natural light, this delightful home offers the perfect blend of comfort, style, and laid-back island living. Step inside to a bright and airy main level featuring a cozy living area, an inviting all-season room ideal for morning coffee or sunset unwinding, a convenient main-level bedroom, and a half bath. Upstairs, two additional bedrooms and a full bath provide a peaceful retreat with peekaboo water views. Enjoy the coastal breeze from your front deck, entertain in the spacious yard, and take advantage of the shed and ample driveway parking. With serene water views and community access to the Bay, this is your opportunity to embrace the Kent Island lifestyle in an adorable A-frame escape that feels like a vacation every day. Whether you're looking for a weekend getaway or a full-time residence, this one has it all. Come see what makes this gem so special!

136 Allegany Rd, Stevensville

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

Selling Office: Keller Williams Realty.

How much is your home worth?

Get instant property value now!