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$1,195,000
4 Beds ⋅ 3 Baths
A Private Wye River Sanctuary! Some properties offer a home. Others offer a lifestyle. This exceptional Wye River retreat offers both.Set along one of the Eastern Shore’s most beautiful waterways, this beautifully updated ranch home is an invitation to slow down, entertain effortlessly, and enjoy waterfront living at its finest. From morning coffee on the screened porch to sunset swims in the Gunite pool, every day here feels like a getaway.The light-filled, open interior provides an inviting backdrop for relaxed gatherings and everyday living, while a versatile additional living area offers the flexibility for an in-law suite, private home office, game room, or guest retreat. The serene primary bedroom enjoys direct access to the screened porch, creating a private connection to the tranquil waterfront setting.The extensive improvements provide peace of mind while enhancing the home's appeal, including an architectural roof, vinyl siding, gutters, sophisticated hybrid heat pump/propane HVAC system, select updated flooring, and an updated BAT septic system.Outside is where this property truly shines. The Gunite pool features strategically placed bench seating, creating the perfect vantage point for unforgettable Wye River sunsets. The screened porch captures the river breezes and provides an ideal setting for morning coffee, afternoon cocktails, or long evenings with friends and family.For the boating enthusiast, the private dock features two electric boat lifts—8,000 and 12,000 pounds—and 2+ feet of mean low water, providing excellent access for boating and watersports. Spend the day on the river, catch crabs from the dock, or simply let the water set the pace.This is more than a waterfront home—it is a place to create traditions, host unforgettable gatherings, escape the ordinary, and experience the Wye River in a deeply personal way.Private waterfront. Private dock. Gunite pool. Sunset views. Exceptional outdoor living. A rare opportunity to make the Wye River your everyday retreat.

225 Hickory Ridge Dr, Queenstown

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$599,900
2 Beds ⋅ 3 Baths
Enjoy the Chesapeake Bay lifestyle from this charming 2-bedroom, 3-bath cottage offering beautiful Bay views and direct access to the water just across the street. Situated on more than .6 acres, the property combines a relaxed coastal setting with a spacious, private backyard that is flat and ideal for outdoor living and entertaining. After a day on the water, unwind in the hot tub, rinse off in the outdoor shower, or simply enjoy the privacy of the backyard. A storage shed provides convenient space for kayaks, paddleboards, bikes, and other outdoor gear. Just across the street, direct access to the Chesapeake Bay and a sandy beach makes it easy to launch a kayak or paddleboard, spend the day along the shoreline, or simply take in the Bay. While the property is non-waterfront, the combination of water views and convenient Bay access offers an exceptional opportunity to enjoy the Eastern Shore lifestyle. Whether you're looking for a weekend getaway or a full-time Shore home, 101 Chesapeake Bay Drive offers an inviting retreat with space, privacy, water views, and the Chesapeake Bay just steps away.

101 Chesapeake Bay Dr, Stevensville

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

$829,966
4 Beds ⋅ 3 Baths
THIS HOUSE HAS NOT BEEN BUILT YET! Timberlake Homes Design|Build provided the description of the home and features. Renderings/elevations are not community-specific and may show features/elements/materials that are not offered in your community of choice. Please see your sales manager to confirm the specific house type elevations available. BEECH - Discover this new design which offers farmhouse-Craftsman charm and a flexible, open layout. This design features a main-level owner’s suite, three upstairs bedrooms, and a convenient first-floor laundry off the two-car garage. The spacious great room flows into a large kitchen island and dining space perfect for entertaining, with stainless steel appliances and a walk-in pantry. Customize with an optional fifth bedroom, sunroom, or screened porch, and a versatile flex space perfect for a home office or playroom. The Beech is designed for comfort, versatility, and easy living. FEATURES include: Main level owner’s suite, Sunroom or screened porch, 4 – 5 bedrooms; 2.5-3.5 bathrooms. Starting from 2,827 base square feet, Island kitchen with stainless appliances, walk-in pantry, and breakfast area Four standard bedrooms, Second-level loft (customizable to a fifth bedroom), two buddy-bath options, owner’s-choice flex space on the main level. Please refer to builders website for more details. This prime residential land parcel, located in the desirable ROMANCOKE ON THE BAY subdivision in Stevensville, MD, offers a unique investment or building opportunity with significant potential for appreciation. Spanning 0.56 acres, this corner lot features wooded areas that provide both privacy and a natural aesthetic, enhancing the property's overall appeal. Strategically positioned just about four blocks from the picturesque Eastern Bay, this lot benefits from proximity to water-oriented activities without the premium of direct waterfront ownership. Investors can capitalize on the growing demand for properties near water bodies, making this an attractive option for future development. The community amenities are a standout feature, including a boat ramp, clubhouse, picnic area, and jogging/walking paths. These facilities not only enhance the quality of life for residents but also increase the property's desirability to potential buyers or renters. With super low association fees, investors can enjoy the benefits of community amenities without the burden of high costs. The lot's corner location along the South Kent Island walking path provides ample privacy and accessibility, which can be advantageous for future residential development. The surrounding area is poised for growth, making this property an excellent long-term investment. As demand for residential properties near water continues to rise, this lot presents a compelling opportunity for those looking to enter the real estate market or expand their portfolio. In summary, this 0.56-acre corner lot in ROMANCOKE ON THE BAY is not just a piece of land; it's a strategic investment in a thriving community with abundant amenities and proximity to Eastern Bay. With the potential for appreciation and the appeal of a water-oriented lifestyle, this property is a must-consider for savvy investors looking to maximize their returns or those seeking to build their dream home.

Touhey Drive, Stevensville

Listing courtesy of Realty Navigator. Contact:

$425,000
4 Beds ⋅ 2 Baths
Photos coming soon! Nestled in the charming community of Romancoke on the Bay, this delightful Cape Cod home offers a perfect blend of comfort and functionality. With 1,440 sq. ft. of well-designed living space, this residence features four inviting bedrooms and two full bathrooms, ideal for both relaxation and entertaining. Step inside to discover a warm atmosphere enhanced by a cozy wood stove, perfect for those chilly evenings. Natural light pours in through thoughtfully placed window treatments, creating a bright and welcoming ambiance throughout. The exterior of the home is equally appealing, featuring low-maintenance vinyl siding and a spacious three seasons room that invites outdoor enjoyment. The 0.45-acre lot is adorned with mature trees, providing a serene backdrop and a sense of privacy. Enjoy the convenience of off-street parking and easy access to community amenities, including walking path, beach, boat ramp and playground. For water enthusiasts, the Chesapeake Bay is just a short stroll away, offering endless opportunities for recreation. Experience the perfect blend of comfort, community, and coastal living.

105 Touhey Dr, Stevensville

Listing courtesy of Kelly and Co Realty, LLC. Contact:

$750,000
1 Beds ⋅ 2 Baths
A truly special Eastern Shore property! This charming Tidewater Cape is beautifully positioned on the point of 13.78 acres, surrounded by the tidal waters of the Chester River. Built in 1950 by a father and son as a summer retreat, the home has been loved and enjoyed by generations and is filled with character and timeless charm. The setting begins to reveal itself as you travel the wooded drive and catch glimpses of the river through the trees. As you approach the homesite, the trees open and water appears on both sides, showcasing the property's unique point setting, privacy, and natural beauty. Charming and inviting from the front, the home's true presence is best appreciated from the waterside, where its distinctive three-story Tidewater elevation creates an impressive view. Inside, hardwood floors extend throughout the main and second levels, complemented by beautiful built-ins and original hardwood details. A main-level porch and lower-level patio provide wonderful spaces to relax and enjoy the peaceful surroundings. Two outbuildings along the shoreline include a one-car garage and a workshop with electric, offering additional storage and workspace. With 13.78 acres, there may be potential for subdividing. *Buyers to verify all possibilities, requirements, and approvals with the appropriate county authorities. A rare opportunity to own substantial acreage with privacy and character in a beautiful Chester River setting. Pier/dock conveys As-Is. DO NOT WALK ON DOCK. Property shown by appointment only. DO NOT ENTER PROPERTY WITHOUT AN APPOINTMENT.

200 Powers Ln, Millington

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

$400,000
3 Beds ⋅ 2 Baths
Secluded Riverfront Get-away. Rare opportunity to own 7.19± wooded acres along the Chester River in Queen Anne’s County. Tucked away at the end of a quiet cul-de-sac, the property features an approximately 1,100-square-foot manufactured home (1987) with a newer roof and windows, rear deck, private well, and BAT septic system approved for up to four bedrooms. NOTE: Manufactured home with skirting-- without a foundation- so it may impact financing approvals. Excellent lot opportunity to add a garage or pole barn. A natural beach area with 770' of riverfront (provides direct river access for fishing, kayaking, boating. Mature woods offer privacy, wildlife habitat, and hunting opportunities rarely found on a traditional waterfront homesite. Whether you're looking for a weekend retreat, full-time residence, recreational getaway, or potential future waterfront homesite, this property offers plenty of possibilities. Convenient access to US Route 301 provides easy travel to Delaware and surrounding Eastern Shore communities. Enjoy 7.19± acres of Chester River waterfront with hunting, fishing, and boating opportunities on Maryland’s Eastern Shore.

405 Rings End Rd, Millington

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

$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:

$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:

$190,000
Vacant lot in upcoming community.

Baltimore Drive Drive, Stevensville

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

$169,000
3 Beds ⋅ 2 Baths
This property consists of two parcels totaling approximately 1 acre (Map 0001, Parcel 10 and Map 0001, Parcel 19). Nestled along the water’s edge, this unique waterfront opportunity offers the perfect canvas to create your own Eastern Shore retreat. Renovate the existing 3-bedroom cottage or explore the potential to rebuild using the existing foundation. With a beautiful waterfront setting and plenty of possibilities, this property is ready for your vision. Buyer to verify all building and renovation restrictions with the county. This property features a new deep well, new well pump, and new septic holding tanks in 2026. The existing interior of the home has been taken down to the framing and includes 100-amp electrical service, providing a solid starting point for your vision. Outdoor enthusiasts will enjoy everything this property has to offer. Fish for perch, bass, catfish, and snakeheads, or spend the day crabbing from your shoreline. Waterfowl hunters will enjoy the existing duck blind, while everyone will appreciate the stunning sunsets overlooking the water. Whether you're looking for a peaceful weekend escape, a hunting and fishing camp, or the site of your future waterfront cottage, this property offers an opportunity that's becoming increasingly difficult to find.

220 Kirbys Landing Rd, Millington

Listing courtesy of Select Land & Homes, LLC. Contact:

$97,500
6.11 wooded acres in the country! Loaded with wildlife! Large secluded pond. Surrounded by large track of woods. Hunters Dream!

1031 Peters Corner Rd, Sudlersville

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

$4,695,000
5 Beds ⋅ 5 Baths
Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

2800 Bennett Point Rd, Queenstown

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

$135,000
**STARTING 9/5 & ENDING 9/12: For one week only, list price is reduced to $125,000 with all closing costs covered by seller!** Nestled in one of the most beautiful and peaceful areas of Queen Anne’s County, this serene wooded lot has already been perc approved and offers the perfect blend of privacy and convenience. The lot is surrounded by mature trees and feels secluded and tranquil while still being just 9 minutes from Historic Chestertown. Convenient access to Routes 213 and 544 makes travel to Centreville, Easton, and Middletown easy. Quotes are already available for septic installation, well installation, and clearing of the existing structure and brush.

109 2nd St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

$429,900
3 Beds ⋅ 2 Baths
*MAJOR PRICE IMPROVEMENT! Welcome to this beautifully renovated and remodeled 3-bedroom, 2-bath home offering the perfect blend of modern style, comfort, and location. Designed with today’s lifestyle in mind, this home features a bright open floor plan with spacious living and dining areas that flow seamlessly into the stunning gourmet kitchen. The kitchen is a true showstopper with elegant quartz countertops, a large center island, and ample space for cooking, gathering, and entertaining. Both full bathrooms have been tastefully updated with ceramic tile finishes and brand-new high-end vanities. The spacious primary suite offers a private retreat with its own en-suite bathroom for added comfort and convenience. Step outside to enjoy the level front and backyard spaces, ideal for outdoor entertaining, gardening, play, or simply relaxing. Located just one block from the Chesapeake Bay, you’ll love the nearby neighborhood waterfront park featuring picnic areas and fishing access. Conveniently situated for commuters, this home offers easy access to the Eastern Shore beaches, Washington, DC, and Baltimore—making it the perfect place to enjoy coastal living with city convenience. Don’t miss this exceptional opportunity! Seller will consider leasing the property to qualified tenants for $3000 per month plus $3000 security deposit.

109 Birch Rd, Stevensville

Listing courtesy of Five Star Real Estate. Contact:

$300,000
22.49 wooded acres on Romancoke Rd in Queen Anne’s County, MD, located 8 miles south of Stevensville. Features include mature pines, trail system, strong deer and turkey presence, and extensive road frontage thru two separate entrance pts. Close to Chesapeake Bay boat access and less than 8 miles to the Bay Bridge. Property has not been perc tested; all uses subject to buyer due diligence. Schedule an appointment for a private tour.

Romancoke Road, Stevensville

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

$174,000
This prime residential land parcel, located in the desirable ROMANCOKE ON THE BAY subdivision in Stevensville, MD, offers a unique investment or building opportunity with significant potential for appreciation. Spanning 0.56 acres, this corner lot features wooded areas, providing both privacy and a natural aesthetic that enhances the property's overall appeal. Strategically positioned just about four blocks from the picturesque Eastern Bay, this lot benefits from proximity to water-oriented activities without the premium of direct waterfront ownership. Investors can capitalize on the growing demand for properties near water bodies, making this an attractive option for future development. The community amenities are a standout feature, including a boat ramp, clubhouse, picnic area, and jogging/walking paths. These facilities not only enhance the quality of life for residents but also increase the property's desirability to potential buyers or renters. With super low association fees, investors can enjoy the benefits of community amenities without the burden of high costs. The lot's corner location alongside the South Kent Island walking path provides ample privacy and accessibility, which can be advantageous for future residential building projects. The surrounding area is poised for growth, making this property an excellent long-term investment. As demand for residential properties near water continues to rise, this lot presents a compelling opportunity for those looking to enter the real estate market or expand their portfolio. In summary, this 0.56-acre corner lot in ROMANCOKE ON THE BAY is not just a piece of land; it's a strategic investment in a thriving community with abundant amenities and proximity to Eastern Bay. With the potential for appreciation and the appeal of a water-oriented lifestyle, this property is a must-consider for savvy investors looking to maximize their returns or those seeking to build their dream home.

Touhey Drive, Stevensville

Listing courtesy of Realty Navigator. Contact:

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

222 Dutchess Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$287,000
HERE IS THE CHANCE YOU HAVE BEEN WAITING FOR. WATERFRONT LOT FOR SALE WITH NO BUILDER TIE IN. NOT MANY LOTS REMAINING FOR SALE. TOWER GARDENS HAS SO MUCH TO OFFER. BOAT RAMP, PLAYGROUND ANDA RARE CHANCE TO BEING ABLE TO BUILD THAT DREAM HOUSE YOU HAVE BEEN WAITING FOR. PUBLIC SEWER ASSESSMENT IS TO BE TRANSFERRED TO BUYER.

114 N Lake Dr, Stevensville

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

$237,000
4 LOTS IN KENTMORR. THIS IS NOT A MISTAKE. LOTS 17,18,20 AND 22. FOR A TOTAL OF 20,000 SQUARE FEET. CORNER OF ALLEN AVE AND ORCHID AVE. WALKING DISTANCE TO MARINA AND RESTAURANT. HERE IS YOUR CHANCE TO HAVE IT ALL. SELL THE CAR AND GET A BIGGER BOAT. BUYER TO VERIFY WITH THE COUNTY ANY BUILDING QUESTIONS. SEWER ASSESSMENT IS TO TRANSFER TO BUYER.

Allen Avenue, Stevensville

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

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

Sparks Corner Sparks Corner Sparks Mill At Route 213 Road, Centreville

Listing courtesy of Tidewater Properties. Contact:

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

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

Listing courtesy of Tidewater Properties. Contact: