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$289,000
2 Beds ⋅ 2 Baths
This charming cottage on the outskirts of town is full of character, thoughtful updates, and endless potential to make it your own. Step inside to find beautiful wide-plank flooring in the living room, creating a warm and welcoming atmosphere. The laundry room and convenient half bath feature brand-new luxury vinyl plank flooring, with the half bath offering enough space to easily add a full-size shower or tub if desired. The kitchen has been updated with stainless steel appliances, making it both stylish and functional. Enjoy relaxing on the enclosed back porch or the inviting front porch, where you'll have a front-row seat to the town's Fourth of July parade. Upstairs, you'll find two cozy bedrooms and a full bathroom with a new vanity and brand-new luxury vinyl plank flooring. The current owners combined two bedrooms to create a spacious primary bedroom, but the layout could easily be converted back to three bedrooms if needed. The outdoor space is just as impressive, featuring a large, fully fenced backyard with a 6-foot privacy/security fence and an oversized garage/barn complete with a brand-new barn door—perfect for storage, hobbies, or a workshop.

6022 N Main St, Rock Hall

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$450,000
3 Beds ⋅ 2 Baths
This well-maintained ranch-style home reflects true pride of ownership and is located in Clarke County—a rare opportunity! Enjoy convenient access to Route 7, Winchester, and Northern Virginia while savoring the peace and privacy of country living. The spacious primary suite features a private en-suite bath, while the generously sized secondary bedrooms provide plenty of additional space. The updated kitchen offers a breakfast bar and newer stainless steel appliances, making it both functional and inviting. An enormous sunroom provides year-round living space and is perfect for relaxing, entertaining. The remodeled bathrooms add modern style and comfort throughout the home. The partially finished basement offers exceptional flexibility, featuring a family room, great room, hobby room, game room, workshop with endless possibilities for customization. Outside, you'll find a paved driveway, a large one-acre lot backing to farmland and mature trees for added privacy, and a spacious outbuilding ideal for storage, hobbies, or equipment. This property combines comfort, convenience, and versatility in a beautiful country setting.

311 Moose Rd, Berryville

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$339,900
3 Beds ⋅ 2 Baths
Welcome to this charming 3-bedroom, 2-bath rancher in the heart of Rock Hall! Freshly painted and move-in ready, this well-maintained home offers comfortable one-level living with a spacious and functional layout. The attached 2-car garage provides plenty of room for parking, storage, or a workshop. Whether you're looking for a year-round residence, a weekend retreat, or a place to enjoy Maryland's Eastern Shore lifestyle, this home is an excellent opportunity. Conveniently located near Rock Hall's marinas, restaurants, shops, and waterfront attractions, you'll love the small-town charm and easy access to boating, fishing, and everything this vibrant coastal community has to offer. Don't miss your chance to make this move-in-ready home your own—schedule your showing today!

5925 Williams St, Rock Hall

Listing courtesy of Century 21 Downtown. Contact:

$480,000
5 Beds ⋅ 2 Baths
Beautifully updated while preserving its character, this charming home is ideally located just a short distance from the Rock Hall Harbor and Chesapeake Bay, offering easy access to waterfront dining, boating, and all the coastal charm Rock Hall has to offer. Relax on the spacious front porch, or entertain on the screened porch, complete with electricity and plenty of space for outdoor dining. Inside, the home seamlessly blends original character with thoughtful modern updates. The large country kitchen retains its classic charm while featuring updated stainless steel appliances. Off of the kitchen you’ll find the formal living and dining rooms, highlighted by beautiful built-in cabinetry and warm original hardwood floors that extend throughout the home. This home offers a first-floor bedroom and an updated full bathroom, offering hard-to-find single-level living. Upstairs there are four additional bedrooms and a second full bathroom, providing plenty of room for family, visitors, or a home office. The large backyard is adjacent to the civic center, providing lots of open space, yet lined with trees for privacy. Filled with warmth, charm, and modern comforts, this beautifully maintained home offers the perfect opportunity to enjoy life in one of Maryland's most beloved waterfront communities. Short distance to Main Street shops, many restaurants, marinas, and the Rock Hall beach.

21251 Chesapeake Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$325,000
3 Beds ⋅ 3 Baths
Welcome to 21128 Striper Run, a charming 3-bedroom, 2.5-bath home nestled in the heart of Rock Hall. Offering an exceptional opportunity to own in one of Maryland's most sought-after waterfront communities, this home combines classic charm, quality features, and outstanding value. Step inside to find beautiful real hardwood flooring throughout the main level, creating warmth and character from the moment you enter. The inviting living room features a cozy gas fireplace, making it the perfect place to gather with family and friends during cooler evenings. The spacious floor plan offers comfortable living with generously sized bedrooms, including a private primary suite with its own full bath. Just off the rear of the home, you'll discover a screened porch overlooking the backyard—a peaceful space to enjoy your morning coffee, entertain guests, or simply relax while taking in the tranquil surroundings. Outside, mature landscaping and a welcoming covered front porch add to the home's curb appeal, while the quiet setting offers the small-town charm that makes Rock Hall such a desirable place to call home. Conveniently located just minutes from marinas, restaurants, shops, parks, and the Chesapeake Bay, this home offers the perfect blend of comfort, character, and Eastern Shore living. Don't miss your opportunity to make 21128 Striper Run your next home!

21128 Striper Run, Rock Hall

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$375,000
3 Beds ⋅ 2 Baths
Sweet corner property in downtown Rock Hall, right on the 4th of July parade route! Just two blocks from the Rock Hall Harbor/ Chesapeake Bay. A welcoming home with a spacious kitchen and formal dining room, or enjoy meals outside in the fenced-in back yard! The large living room has hardwood floors and a wood stove for cozy winter nights. This home features a hard to find first-floor primary bedroom! Upstairs offers two additional bedrooms, a full bath, and an additional office or activity room. The home is situated on a large corner lot, set back from Main St., offering privacy and nice yard space. The charming garage with a loft is a great space for storage or a workshop. Close to all Rock Hall has to offer: marinas, shops, restaurants, and the Chesapeake Bay! This popular vacation rental could continue as an income producer but would also make a fantastic full-time residence. Being sold turn-key, just unpack your bags and enjoy. The homes hot water heat has been updated, zoned to both floors. Tankless hot water heater.

5686 S Main St, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$370,000
3 Beds ⋅ 2 Baths
Quintessential Rock Hall home with an abundance of charm! Located in the heart of Rock Hall, a short distance to Main Street shops, many fantastic restaurants, and seven marinas. Enjoy evenings and mornings on the screened porch, which runs the expanse of the home. Entering from the porch, you'll find a cosy living room and a galley kitchen with open dining space. This home offers a first-floor bedroom and full bathroom, plus two additional bedrooms and a full bath on the second floor. There's a walk-up attic for additional storage, shed in the yard, laundry and utility room off the kitchen. Many updates have been made throughout the years, such as the addition of a copper roof on the front porch, updated bathrooms, flooring, and updated lighting. Recent updates include the home's heating system. Don't miss this downtown gem!

21384 E Sharp St, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$449,000
3 Beds ⋅ 2 Baths
Your Chesapeake Bay getaway just steps from Haven Harbour South Marina. Launch your boat, dine on the waterfront, stroll to the beach, and enjoy resort-style living from this beautifully updated home. This updated 3-bedroom, 2-bath rancher situated on an expansive lot with glimpses of the water and room to relax, entertain, and enjoy the Eastern Shore lifestyle. The spacious detached garage provides ample storage for vehicles, boats, and recreational equipment. Unwind in the cooled three-season room overlooking the fenced backyard, offering the perfect setting for gatherings with family and friends after a day on the water. Ideally located just a short walk or golf cart ride from Haven Harbour South Marina, you'll enjoy convenient access to boat slips, waterfront dining, a sandy beach, marina amenities, and breathtaking Chesapeake Bay sunsets. Whether you're seeking a year-round residence, weekend escape, or boating retreat, this property offers comfort, convenience, and the best of Rock Hall living. Resort-style living just steps from Haven Harbour South Marina.

21120 Green Ln, Rock Hall

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

$649,900
4 Beds ⋅ 4 Baths
This home has been meticulously maintained and is located in the heart of everything Rock Hall has to offer! The 2 story entrance foyer with tile floors is just the beginning of the surprise you will find in this special, 2,900+/- square foot, home. There are 4 bedrooms, 3.5 baths, a large living room with cathedral ceiling, 2 bedrooms upstairs and 2 bedrooms down, heat pump and mini-split systems for heating and cooling and is move in ready!! A free standing propane stove will help take the chill off during the cooler months. The dining area is just off the kitchen with great views from the large picture window. The kitchen offers all of the major appliances. The laundry room is also a very nice size. There is a side deck for outdoor entertaining. Need storage?.....There is an interior storage/shop room and a large shed to keep some of your summer toys. The crawl space has been recently encapsulated. Need more room or maybe a guest house? The adjoining lot already has sewer and water and is included with the sale. Or just enjoy the open space between you and the next door neighbors. This could make a great full or part time residence! Only a short distance to the harbor and restaurants! Watch the Rock Hall July 4th fireworks right from your deck next year!!

21173 and 21163 Chesapeake Ave, Rock Hall

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$399,000
4 Beds ⋅ 2 Baths
Welcoming to 21424 Catholic Ave, located in the heart of Rock Hall! Walking distance to many shops, restaurants, and marinas. Nicely situated on a large in-town parcel, the largest residential lot on Catholic Avenue. This 4-bedroom home was redone from the inside out in 2024. The welcoming living space contains original wood accents, adding much charm to this newly updated home. Spacious open living space with a beautifully renovated kitchen, custom wood cabinets, new LVT, and engineered hardwood flooring throughout. Three bedrooms, with great closet space, share a full bath. At the end of the home, you'll find the primary bedroom, with a spacious primary bath and walk-in closet. The oversized two-car garage has plenty of room for extra storage. One-floor living and a two-car garage are hard features to find in downtown Rock Hall. Outside, the possibilities are endless; there's ample room for outdoor activities or projects. Updates include: -Crawlspace encapsulation and whole house dehumidifier -10 new windows -New 25 year roof -Siding, shutters & new gutters -New flooring, engineered hardwood, LVT and carpet -Completely updated kitchen with custom cabinetry -HVAC heat pump & AC -200 amp breaker panel And more!

21424 Catholic Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$425,000
This unique mixed-use property offers exceptional flexibility and opportunity just outside the town of Rock Hall. The first floor features a versatile storefront currently operating as a bookstore, with a history of successful uses including a fabric studio, pottery studio, marine engine shop, and appliance store—showcasing its adaptability for a wide range of business ventures. The second-floor residential space provides comfortable living with an eat-in kitchen, formal living room, family room, one full bath, and two bedrooms. A spacious rear deck extends the living area outdoors, perfect for relaxing or entertaining. Additional improvements include a 35’ x 28’ pole barn and a 28’ x 14’ shed currently utilized as a bookstore event space, adding even more functional possibilities. The property also features a beautiful garden area ideal for outdoor gatherings and enjoyment. With its prime location just outside Rock Hall, this property blends commercial opportunity with residential comfort in a highly desirable setting.

6202 Rock Hall Rd, Rock Hall

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

$50,000
Build your Eastern Shore getaway on this desirable in‑town lot in the heart of Rock Hall, just moments from marinas, waterfront dining, and all the charms of this beloved harbor town.. Rare opportunity to own a cleared, town‑served building lot on East Sharp Street, offering approximately 0.31 acres (about 13,500+ square feet) in Rock Hall’s R‑1 low‑density residential district. With public water and public sewer available at the street and no existing structures to remove, this property is truly build‑ready for your custom home, weekend retreat, or full‑time residence. Enjoy the convenience of being within Rock Hall town limits—close to shops, restaurants, public beach, and multiple marinas—while still having a deep, private lot that lends itself to a long drive, landscaped backyard, and room for decks or a future garden. Whether you’re dreaming of a low‑maintenance coastal cottage or a year‑round home base for boating and fishing on the Bay, this lot is a prime canvas in one of Kent County’s most sought‑after waterfront communities.

21451 E Sharp St, Rock Hall

Listing courtesy of Bayside Realty. Contact: (443) 829-5828
$425,000
2 Beds ⋅ 2 Baths
This unique mixed-use property offers exceptional flexibility and opportunity just outside the town of Rock Hall. The first floor features a versatile storefront currently operating as a bookstore, with a history of successful uses including a fabric studio, pottery studio, marine engine shop, and appliance store—showcasing its adaptability for a wide range of business ventures. The second-floor residential space provides comfortable living with an eat-in kitchen, formal living room, family room, one full bath, and two bedrooms. A spacious rear deck extends the living area outdoors, perfect for relaxing or entertaining. Additional improvements include a 35’ x 28’ pole barn and a 28’ x 14’ shed currently utilized as a bookstore event space, adding even more functional possibilities. The property also features a beautiful garden area ideal for outdoor gatherings and enjoyment. With its prime location just outside Rock Hall, this property blends commercial opportunity with residential comfort in a highly desirable setting.

6202 Rock Hall Rd, Rock Hall

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

$329,000
4 Beds ⋅ 2 Baths
Welcome to this beautifully renovated 4-bedroom, 2-bath Cape Cod located in the heart of Rock Hall, MD! Completely updated from top to bottom, this home features a brand-new roof, HVAC system, water heater, flooring, paint, upgraded bathrooms, interior doors, and stylish recessed lighting as well as ceiling fans throughout. Enjoy mornings and evenings on the charming screened-in front porch, perfect for relaxing or entertaining. Inside, the home offers a bright and open layout with modern finishes while still retaining that classic Cape Cod charm. Sitting on a large lot, there’s plenty of space for outdoor activities, gardening, boat storage or future expansion. The is ample parking in the driveway as well as two-way access. Ideally situated in the sought-after waterfront town of Rock Hall, you’ll be just minutes from multiple boat ramps, marinas, and a short walk to restaurants, local shops, and the center of town. Whether you're looking for a full-time residence or a weekend getaway, this turn-key home delivers the best of Eastern Shore living. Move-in ready and loaded with upgrades—don’t miss this opportunity!

21305 Haven Rd, Rock Hall

Listing courtesy of RE/MAX Point Realty. Contact: (302) 426-2211
$3,150,000
7 Beds ⋅ 7 Baths
All showings require pre screening and financial capability prior to scheduling any showing. Rarely does a property of this sort come available in Kent County Maryland! This incredible 139+/- acre Chesapeake Bay property is available in it's entirety, however the seller may consider selling the primary residence with a reduced amount of acreage under the right conditions, providing the purchaser bares the cost to do so and is willing to wait the extended period of time to accomplish. The entire property features 72+/- tillable acres, 3900+/- footage of Chesapeake Bay beach frontage, extensive County road frontage, a 3.5 acre waterfowl pond, 2 other smaller ponds, a ten stall horse barn, and caretakers home. A large 33+/- acre flooded area, teeming with waterfowl and deer surrounded by woods runs through the heart of the property. The main residence, designed by architect Paul Rudolf, is perched upon the rip rapped shores of the Chesapeake Bay with endless broad water views. Although the main residence is in need of complete restoration, the site is extraordinary and the salvage reward is potentially significant in dollar value. There is a possibility for construction of a new home on the existing building pad. The hunting and recreational value for this property is enormous! Just imagine family picnics on the sandy beach or spending countless hours searching for sea glass and Indian artifacts while soaking up the sun and listening to the gentle waves roll up on the beach. This property is extremely private, however, convenient to Historic Chestertown, summer fun in Rock Hall, and a short drive to regional airports in Philadelphia, Baltimore and Washington DC. The property is being sold AS-IS, Where-IS and requires 24 hour notice to show with listing agent on site for any and all showings.

6520 Swan Creek Rd, Rock Hall

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$3,150,000
7 Beds ⋅ 7 Baths
All showings require pre screening and financial capability prior to scheduling any showing. Rarely does a property of this sort come available in Kent County Maryland! This incredible 139+/- acre Chesapeake Bay property is available in it's entirety, however the seller may consider selling the primary residence with a reduced amount of acreage under the right conditions, providing the purchaser bares the cost to do so and is willing to wait the extended period of time to accomplish. The entire property features 72+/- tillable acres, 3900+/- footage of Chesapeake Bay beach frontage, extensive County road frontage, a 3.5 acre waterfowl pond, 2 other smaller ponds, a ten stall horse barn, and caretakers home. A large 33+/- acre flooded area, teeming with waterfowl and deer surrounded by woods runs through the heart of the property. The main residence, designed by architect Paul Rudolf, is perched upon the rip rapped shores of the Chesapeake Bay with endless broad water views. Although the main residence is in need of complete restoration, the site is extraordinary and the salvage reward is potentially significant in dollar value. There is a possibility for construction of a new home on the existing building pad. The hunting and recreational value for this property is enormous! Just imagine family picnics on the sandy beach or spending countless hours searching for sea glass and Indian artifacts while soaking up the sun and listening to the gentle waves roll up on the beach. This property is extremely private, however, convenient to Historic Chestertown, summer fun in Rock Hall, and a short drive to regional airports in Philadelphia, Baltimore and Washington DC. The property is being sold AS-IS, Where-IS and requires 24 hour notice to show with listing agent on site for any and all showings.

6520 Swan Creek Rd, Rock Hall

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$375,000
3 Beds ⋅ 2 Baths
UPDATE - New carpet just installed! Convenient one-level living in this 3BR, 2.5 bath rancher. The house has a desirable split bedroom layout with the primary bedroom, bath & closet off the kitchen and two bedrooms and another full bath off the other side of the house. The sun room has a propane stove and exits to a 12' x 15' deck. There's a 10' x 16' shed. Nice quiet, in-town location.

21336 Haven Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$300,000
Great location - attractive commercial building in popular boating town of Rock Hall. Perfect for professional office, art gallery, yoga studio, retail space. Last used as a florist shop. Beautiful display windows, two bathrooms, a kitchenette area. Gleaming, eye-catching metal roof. Parking for at least 12. A versatile property which provides a dynamic presence in a prime location.

21435 Rock Hall Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact: