Refine Search
Sort by
1025 Dundee Ct, Chester
$280,000
3 Beds ⋅ 3 Baths
Estate Sale! Incredible opportunity to own one of the best values on Kent Island. Priced well below its potential, this 3-bedroom, 2.5-bath Dundee Harbor townhome offers approximately 1,400 square feet with an excellent upside. An updated home in the community sold for $365,000 in 2025, and this property offers outstanding potential for investors, flippers, or buyers looking to build equity. Enjoy relaxing or entertaining on the rear deck, then take advantage of Dundee Harbor's water privileges on Piney Creek, including a private community pier for fishing, kayaking, paddleboarding, crabbing, or simply enjoying the waterfront. Just minutes from Kent Narrows, you'll love the waterfront restaurants, marinas, boat ramps, tiki bars, live entertainment, and Chesapeake Bay lifestyle. Conveniently located near shopping, everyday conveniences, and Route 50, this home offers an easy commute while delivering the relaxed Eastern Shore lifestyle buyers are looking for. Whether you're searching for an investment property, primary residence, or weekend retreat, this Estate Sale is an opportunity you won't want to miss. Schedule your showing today!

1025 Dundee Ct, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Douglas Realty LLC.

4003 Main St, Grasonville
$280,000
2 Beds ⋅ 1 Baths
Eastern Shore charm in the heart of Grasonville! This adorable cottage offers easy one-level living and features a thoughtfully designed addition that creates an expansive gathering space perfect for entertaining family and friends. Accessibility is enhanced with a convenient ramp, making everyday living comfortable and practical. Numerous improvements have been completed over the years, including an energy-efficient mini-split heating and cooling system. Move-in ready and full of character, this home presents an excellent opportunity for buyers seeking affordability, convenience, and Eastern Shore living. Being sold as-is, with plenty of potential for a handy homeowner to add their own finishing touches and build additional equity.

4003 Main St, Grasonville

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

Selling Office: Keller Williams Realty.

114 Merganser Ct, Chester
$280,000
2 Beds ⋅ 2 Baths
"Why rent when you can own?" or are you looking for a weekend home? This condo is has so many options at an affordable price. Experience the ease of resort-style, maintenance-free living in this beautifully updated upper-level condominium featuring open views, abundant natural light, and the privacy of having no neighbors above. Also, owning the upper level gives you the security if you are a lock and leave weekender. 2nd floor condos feature vaulted ceilings that are unavailable on the main level. Soaring vaulted ceilings, open floor, beautiful hardwood floors, gourmet Kitchen offers all brand new appliances including refrigerator, dishwasher, stove with glass top, microwave and garbage disposal. The beautiful living area features a gas fireplace for those chilly days coming soon and the dining area is perfect for entertaining and flows from the kitchen, dining to the balcony. This condo also includes a new efficient hot water heater and stackable full size washer and dryer. Owner has meticulously maintained this home. The spacious primary suite offers a peaceful retreat with a generous bedroom, walk-in closet and a private ensuite bath. A second bedroom provides exceptional flexibility as a guest room, home office, or space for family and grandchildren. Another full bath is located near the second bedroom. Beyond the home, enjoy an exceptional lifestyle with access to community amenities including a clubhouse, swimming pool, pickleball courts, and fitness center. A marina is within walking distance, making it easy to enjoy boating and waterfront activities. Bayside is a friendly pet community with many paths for dog walking. The cross trail is just steps from your condo. The condominium association handles exterior maintenance and community upkeep, allowing you more time to enjoy the things you love. Ideally situated near fine dining, shopping, and cultural attractions, this location also offers outstanding accessibility—within easy reach of three international airports—making travel convenient whether for business, family visits, or leisure. This is the perfect opportunity to enjoy a low-maintenance lifestyle without sacrificing comfort, convenience, or amenities. "Elevated living, exceptional amenities, and a carefree lifestyle—all in one remarkable home."

114 Merganser Ct, Chester

Listing courtesy of Benson & Mangold, LLC. Contact:

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

111 Cemetery Ln, Church Hill
$280,000
3 Beds ⋅ 1 Baths
Charming farmhouse located in the quaint town of Church Hill. This home offers over 1,400 square feet of living space, featuring three bedrooms, one bathroom, a kitchen, a living room, and a designated dining area. The property also includes a welcoming front porch and sits on a spacious .80-acre lot. A highlight of this property is the expansive detached garage/workshop, equipped with a utility sink, wood stove for the cold winter months and a full second floor, offering endless possibilities for a studio, home office, or extensive storage. The home is conveniently situated between Centreville and Chestertown with easy access to Route 213 and Route 301. Just minutes away from water sports at Rolphs Wharf and other local boat launches, and only 25 minutes from Middletown, Delaware, for tax-free shopping.

111 Cemetery Ln, Church Hill

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

Selling Office: Rosendale Realty.

6 Queen Victoria Way, Chester
$275,000
1 Beds ⋅ 1 Baths
Price Improvement!! Marina-front and perfectly sized for easy living or a weekend escape. This one-bedroom one-bath condo offers approximately 724 square feet with an open floor plan and a geourgous view. Walk into a bright living area that flows seemlessly into the adjacent kitchen, creating an inviting and functional space for everyday living or entertaining. The kitchen has been updated with granite countertops, stainless steel appliances, upgraded cabinetry with self-closing drawers, and a clean, modern layout that maximizes both storage and workspace. Luxury vinyl plank flooring was added throughout, giving the home a cohesive and low-maintenance finish. The living room also features handmade, unique Venetian Stucco wall art straight from Italy that adds character and warmth to the space. The bedroom is located on the marina side and opens directly to a private, partially covered patio with full marina views, making it the ideal spot to enjoy morning coffee or unwind at sunset. The sunsets here are among the best in the community. Two outdoor storage closets are located off the patio, a rare and valuable feature for a one-bedroom unit. Lower condo fees help keep monthly expenses manageable, making this an excellent option for a primary residence, second home, or weekend getaway. For added peace of mind, the seller is offering a one-year home warranty to the buyer.The building roof was replaced in 2020 with 30-year architectural shingles. Queens Landing is known for its Spanish-style architecture and resort-style amenities, including a waterfront heated pool, fitness center, tennis and pickleball courts, clubhouse, and walking paths along the Chester River and marina. Boat slips are available for rent or purchase, and residents enjoy the convenience of being able to walk to nearby restaurants. A rarely available marina front one bedroom offering water views, outdoor space, and affordability in one of Kent Island’s most established waterfront communities.

6 Queen Victoria Way, Chester

Listing courtesy of Realty Navigator. Contact:

Selling Office: Redfin Corp.

116 The Pond Way Unit 3C, Church Hill
$261,000
2 Beds ⋅ 2 Baths
Sellers offering to pay capital contribution fee with acceptable offer. 55 and over community, this newly updated home features an inviting open floor plan, highlighted by luxurious vinyl plank and ceramic tile flooring, along with cozy carpeting in the primary bedroom. The galley kitchen, complete with upgraded countertops and built-ins, flows seamlessly into the dining and living areas, making it ideal for entertaining or quiet evenings at home. Enjoy the warmth of the gas fireplace, or step outside to your porch overlooking the beautifully maintained common areas. The property includes an attached garage with a paved driveway, ensuring easy access and ample parking. Residents benefit from a well-managed association that covers custodial services, exterior maintenance, and snow removal, allowing you to focus on enjoying life. The community offers lovely common grounds and a party room for gatherings. Located near local parks and excellent public services, this neighborhood fosters a vibrant lifestyle. With nearby towns like Chestertown and Centreville for shopping and restaurants and recreational facilities, you'll find everything you need just a short distance away. Experience the comfort of home in a community that values connection and convenience. Recent updates include; Finished 2nd floor with drywall, electric, lights & ceiling fans, paint and carpet. Installed new LVP flooring through most of 1st floor, installed foam insulation, new sump pump and dehumidifier in crawl space. Installed brand new REEM HVAC system. New washer/dryer. New water softener and reverse osmosis water filter. Completely new kitchen with cabinets, sink, quartz counter tops, disposal, gas stove/oven and under cabinet lighting. New insulated garage door with new opener and key pad entry. New ceiling fan in guest bedroom. New carpet in primary bedroom, new LVP flooring in primary bathroom, new light fixtures in primary bedroom and closets. Come see the 55+ community; The Pond at Church Hill. The community encircles a large, grassy, common area with a shaded pond at one end. This is an interior unit with 2 bedrooms/2 baths and newly finished 2nd floor that could be bedrooms, craft, or recreation room. Lots of possibilities.. The area also features 2 established community theatres!

116 The Pond Way Unit 3C, Church Hill

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Douglas Realty LLC.

1 Compass Cir Unit 2, Stevensville
$258,000
2 Beds ⋅ 2 Baths
Updated 2-Bedroom Condo with Garage in Water-Privileged Community – Immediate Occupancy! Don’t miss this beautifully renovated two-level condo featuring 2 bedrooms, 1.5 baths, and a one-car garage. Priced to sell! Thoughtfully updated over the past five years, this home offers newer carpet and luxury vinyl plank flooring, a remodeled kitchen and bathrooms, and a high-efficiency Bosch HVAC system. All major appliances—including kitchen appliances, oversized washer and dryer, and hot water heater—have been recently replaced. The main level features an open living room, galley-style kitchen, convenient half bath, and a versatile bonus room ideal for a dining area or home office. Sliding glass doors lead to a private rear deck with direct access to the parking area and spacious 21x10 garage. Upstairs, you’ll find two generously sized bedrooms and a full bath. Enjoy the benefits of a water-privileged community with access to a pool, pier, and boat docks. HOA fees cover fresh and wastewater, trash pickup, lawn care, shrub maintenance, roof and shingles, crawl space upkeep, exterior hose bib, pool, boat dock, fishing pier, and maintenance of common areas and entrance decking—providing low-maintenance living. Conveniently located for an easy commute to Rt. 50, Annapolis, and Easton, and within walking distance to restaurants and shopping.

1 Compass Cir Unit 2, Stevensville

Listing courtesy of Berkshire Hathaway Homeservice Homesale Realty. Contact:

Selling Office: Maverick Realty, LLC.

7 Mariners Way Unit #2, Stevensville
$255,000
2 Beds ⋅ 2 Baths
This charming 2 bedroom 1.5 bathroom condo located in a waterfront community which provides direct access to Thompson Creek which flows into Cox Creek offering fishing, crabbing and boating just steps away. This unit has new carpet upstairs,brand new stainless steel appliances in kitchen with tile floors. Beautiful hard wood floors in living area. Unit offers a one car garage.,additional off street parking and overflow area for guest parking.The community boasts a inground pool overlooking the creek, clubhouse and picnic area perfect for social gatherings. HOA fees also cover water,sewer and trash costs. Close to shopping, food, schools, parks, Kent Island Trail and Bay bridge. Home warranty provided. Slips are assigned by unit number and available for use only after purchase by unit owner. The current assigned slip located on Dock A is transferable for a one time fee of $3000.00

7 Mariners Way Unit #2, Stevensville

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

Selling Office: EXP Realty, LLC.

3 Queen Victoria Ct, Chester
$230,000
1 Beds ⋅ 1 Baths
Price improvement and ready to move in! Welcome home to Queens Landing. One bedroom condo with open concept kitchen and living room. The spacious bedroom has plenty of closet space and access to a gated private courtyard with locked storage area. Laundry closet is conveniently situated off the bedroom. Move in ready with fresh paint throughout, new LVP floors in the living areas, and new carpet in the bedroom. Queens Landing is a waterfront condominium community on Kent Island located minutes from Rt. 50 and a short walk to local dining and the Cross Island Trail. The community offers a club house, marina, pool, fitness center, pickleball, tennis, and racquetball courts, and social activities throughout the year. Schedule your tour today!

3 Queen Victoria Ct, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Unrepresented.

1603 Marion Quimby Dr, Stevensville
$222,500
3 Beds ⋅ 2 Baths
Rarely available first floor condominium centrally located on Kent Island and in the Thompson Creek Community. Enjoy all the amenities of this water access community including the pool, tennis courts, clubhouse, and within a short walking distance to the water where you sit in a quiet community of proud homeowners. As you arrive, you will notice the peace and tranquility this community offers. Open the door and you will be greeted by the ample living room which features a cozy corner fireplace, plenty of sunlight that fills the home and sliders leading to the private covered balcony where you can enjoy views of the sunsets. Take advantage of the small outside storage closet. The kitchen provides everything a passionate cook needs to prepare even the most elaborate of meals. The primary bedroom features large windows, an ample closet and its private full bath. The other two bedrooms are equal in size and also offers sufficient space for a growing family. Another full bath can be found in the hallway. This condo offers PLENTY of parking and SUPER convenient location - less than 5 minutes to the Bay Bridge, Restaurants, Shopping, and ALL that the Island life has to offer.

1603 Marion Quimby Dr, Stevensville

Listing courtesy of Northrop Realty. Contact:

Selling Office: Corner House Realty.

26 Queen Anne Way, Chester
$214,400
1 Beds ⋅ 1 Baths
Bring your vision to one of the most affordable condos currently available in Queen’s Landing. This one-bedroom, one-bath unit offers approximately 640 square feet and is priced well below its tax-assessed value to reflect its original interior condition, giving buyers the flexibility to update and personalize the space to suit their own style. The condo overlooks Lake Amletto, offering a pleasant water view and the relaxing sound of the nearby fountain, while the Chester River is just a short walk away across the street. One-bedroom units benefit from a lower monthly condominium fee while still enjoying access to the community’s many amenities, including the waterfront pool, clubhouse, fitness center, pickleball and tennis courts, walking paths, marina setting, and beautifully maintained grounds. For a water-oriented lifestyle, boat slips may also be available for purchase or rental within the community, subject to availability. Whether you are looking for an affordable entry into Queen’s Landing, a renovation project, an investment opportunity, or a weekend retreat near the water, this property offers plenty of potential.

26 Queen Anne Way, Chester

Listing courtesy of Realty Navigator. Contact:

Selling Office: Unrepresented.

1826 Sudlersville Rd, Sudlersville
$180,000
3 Beds ⋅ 1 Baths
Opportunity Knocks in Sudlersville! Situated on 1.41 acres, this 3-bedroom, 1-bath home presents a rare chance to create value in an area where renovated homes are selling for significantly more. This property is in need of extensive renovation, but the upside potential makes it an excellent opportunity for investors, renovators, or buyers looking to design a home on a spacious lot. The former garage has been converted to storage space, offering flexibility for future use or redesign. With the right vision, this property can be transformed into something truly special. Sold strictly AS-IS, WHERE-IS. Seller has never occupied the property. Buyer responsible for verifying all utilities, systems, and property condition. Bring your vision and make it your own!

1826 Sudlersville Rd, Sudlersville

Listing courtesy of 212 Degrees Realty, LLC. Contact:

Selling Office: Rosendale Realty.

108 Price Rd, Chester
$170,000
3 Beds ⋅ 2 Baths
You wouldn't think it but the property offers 3 bedroom and 2 full baths. Patio right off kitchen for the summer cookouts! Easy yard maintenance here, not much grass to manage, leaves plenty of time for those cookouts. Close to Route 8 for easy east/west access. Property sold as is, no repairs will be made by seller. HUD CASE 244-032645, reach out for more information on this unique buying opportunity. Property is owned by the US Dept. of HUD. All HUD Homes are sold “AS-IS”. This property is HUD Case # 244-032645. Information and Disclosures available at hudhomestore website. property Insurability code is: IE. Bids may only be submitted by HUD Registered Agents/Agencies. Buyers are responsible for Dewints/Rewints coordination/expenses. LBP (Lead-Based Paint) may be present. Seller makes no representations or warranties as to property condition.

108 Price Rd, Chester

Listing courtesy of Thurston Wyatt Real Estate, LLC. Contact:

Selling Office: Engel & Volkers Annapolis.

13704 Main St, Queen Anne
$140,000
4 Beds ⋅ 1 Baths
Opportunity awaits in the quaint town of Queen Anne. This 4-bedroom, 1-bath farmhouse offers plenty of potential. The home features double side porches, off-street parking and classic farmhouse character, but is in need of updates and repairs. Previously used as a rental property for many years, this property could present an opportunity for an investor, contractor or buyer looking to restore and build equity. Property is served by a shared well with the adjoining property (13706 Main Street), which is also being offered for sale. Conveniently located less than 3/4 mile from Hillsboro Landing, providing access to Tuckahoe Creek for boating and fishing, and less than 5 miles from Tuckahoe State Park. Known for its 60-acre lake, the park offers boating, fishing, playgrounds, and over 20 miles of scenic hiking, biking, and equestrian trails.

13704 Main St, Queen Anne

Listing courtesy of Benson & Mangold, LLC. Contact:

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

How much is your home worth?

Get instant property value now!