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Offers due Wednesday 4/22 by 6PM! Welcome to this beautifully upgraded 3-bedroom, 2-bath Cape Cod, just six years young and perfectly situated in the sought-after Chesapeake Landing community! Ideally located directly across from the Turtle Trail and Millbrook Pond, you’ll love the peaceful, water-oriented setting with nearby access to a community boat ramp, fishing pier, Worton Creek marina, and new restaurant opening soon. This is far from your typical builder-grade home—the current owners have thoughtfully enhanced every inch. The kitchen truly shines with custom upgrades including a built-in pantry, stunning butcher block countertops, island addition, and bar-top seating—plus a full suite of high-end appliances (yes, even a refrigerator with a large touchscreen!). The flexible floor plan offers the best of both worlds with a dedicated dining room and a first-floor bedroom, ideal for guests or one-level living. Outside, enjoy an extended patio, freshly graded yard, and a new storage shed, creating the perfect outdoor space for relaxing or entertaining. With motivated sellers who have already found their next home, this is an incredible opportunity to move right in and start enjoying all that Chesapeake Landing has to offer. Don’t miss your chance to make it yours!

10594 Millbrook Dr, Chestertown

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

Selling Office: Unrepresented.

$329,000

Nestled on a spacious corner lot in the heart of Galena, this historic American Four Square blends timeless character with modern updates. Known for its barn-style outbuildings—perfect for storage, workshop space, or future restoration—this property offers both charm and functionality. Outdoor living is at its best with a beautifully restored in-ground swimming pool, ideal for entertaining or enjoying a private staycation. Sip, dip, and float your cares away in your own backyard retreat. Inside, the home features 4 bedrooms and 1.5 baths. A large family room addition provides the perfect gathering space, while the formal dining room is ready to host holiday dinners and special occasions. The kitchen offers a generous eat-in area along with updated appliances and essentials for everyday cooking. This home has been thoughtfully maintained with significant upgrades, including: 2025: New roof, New pool plumbing, liner, filter, chlorinator, light, and New water heater 2024: New sewer line, paved driveway, kitchen stove, and hood From its historic details to its modern conveniences, 228 Phelps Ave captures the perfect balance of old and new—a true piece of Galena’s history ready to welcome its next chapter.

4 Beds ⋅ 2 Baths

Nestled on a spacious corner lot in the heart of Galena, this historic American Four Square blends timeless character with modern updates. Known for its barn-style outbuildings—perfect for storage, workshop space, or future restoration—this property offers both charm and functionality. Outdoor living is at its best with a beautifully restored in-ground swimming pool, ideal for entertaining or enjoying a private staycation. Sip, dip, and float your cares away in your own backyard retreat. Inside, the home features 4 bedrooms and 1.5 baths. A large family room addition provides the perfect gathering space, while the formal dining room is ready to host holiday dinners and special occasions. The kitchen offers a generous eat-in area along with updated appliances and essentials for everyday cooking. This home has been thoughtfully maintained with significant upgrades, including: 2025: New roof, New pool plumbing, liner, filter, chlorinator, light, and New water heater 2024: New sewer line, paved driveway, kitchen stove, and hood From its historic details to its modern conveniences, 228 Phelps Ave captures the perfect balance of old and new—a true piece of Galena’s history ready to welcome its next chapter.

228 Phelps Ave, Galena

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

Selling Office: Northrop Realty.

Nestled in the charming Rock Hall community, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 2006, this well-maintained residence features spacious living space, thoughtfully designed for modern living. The corner lot provides ample outdoor space for gardening, play, or simply enjoying the serene surroundings. Step inside to discover three inviting bedrooms and two full bathrooms, ideal for relaxation and privacy. The open layout encourages a warm flow between living areas, making it perfect for gatherings or quiet evenings at home. The attached front-entry garage and driveway provide convenient parking options, ensuring you and your guests feel right at home. Rock Hall is known for its friendly atmosphere and community spirit with local shops, restaurants, marinas, Ferry Park Beach and the Chesapeake Bay and many more area attractions. This property is not just a house; it's a place where memories are made. With its inviting design and prime location, it offers a wonderful opportunity to embrace a lifestyle of comfort and community. Don't miss your chance to make this charming home your own!

Nestled in the charming Rock Hall community, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 2006, this well-maintained residence features spacious living space, thoughtfully designed for modern living. The corner lot provides ample outdoor space for gardening, play, or simply enjoying the serene surroundings. Step inside to discover three inviting bedrooms and two full bathrooms, ideal for relaxation and privacy. The open layout encourages a warm flow between living areas, making it perfect for gatherings or quiet evenings at home. The attached front-entry garage and driveway provide convenient parking options, ensuring you and your guests feel right at home. Rock Hall is known for its friendly atmosphere and community spirit with local shops, restaurants, marinas, Ferry Park Beach and the Chesapeake Bay and many more area attractions. This property is not just a house; it's a place where memories are made. With its inviting design and prime location, it offers a wonderful opportunity to embrace a lifestyle of comfort and community. Don't miss your chance to make this charming home your own!

5925 Williams St, Rock Hall

Listing courtesy of Century 21 Downtown. Contact:

Selling Office: LPT Realty, LLC.

Welcome home to 10572 Watonga Road, a charming Cape Cod nestled on a beautifully wooded corner lot in the desirable Chesapeake Landing community. Built in 2007 and meticulously maintained, this 3-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and Eastern Shore charm. The spacious .35-acre property is surrounded by mature trees, creating peaceful wooded views from both the front and back of the home. Inside, you'll find luxury vinyl plank flooring throughout the main living areas in near-new condition, along with well-maintained carpeting in the bedrooms. Thoughtful updates include a water softener installed in 2024, a fenced yard added just two years ago, French drains, and two sump pumps designed to keep the property draining efficiently. An oversized shed provides excellent storage, while the deck offers the perfect place to enjoy your private outdoor setting. Life in Chesapeake Landing is all about enjoying nature and the water. Residents frequently spot deer, wild turkeys, turtles, and other local wildlife throughout this quiet, established neighborhood. There is no HOA, but the voluntary community association provides access to sought-after water amenities, including a community boat ramp, kayak launch, and fishing pier. The neighborhood also features Mill Brook Pond and the popular Turtle Walking Trail, giving residents even more opportunities to enjoy the outdoors. Located just minutes from historic Chestertown, you'll have easy access to everything that makes Kent County so special. Downtown Chestertown is only about seven minutes away and offers a vibrant year-round farmers market every Saturday from 9 a.m. to noon, locally owned shops, a beloved independent bookstore, and favorite dining destinations like Bad Alfred's Distilling. Also check out the sand bars at the marinas, perfect for waterfront happy hours. Whether you're drawn to the area's marinas, boating opportunities, charming small-town atmosphere, or the spacious homesites that provide room to breathe, this property delivers the true Eastern Shore lifestyle where water access is around every corner and community charm is abundant. If you've been searching for a home that combines modern convenience, natural beauty, and small-town waterfront living, 10572 Watonga Road is ready to welcome you home.

Welcome home to 10572 Watonga Road, a charming Cape Cod nestled on a beautifully wooded corner lot in the desirable Chesapeake Landing community. Built in 2007 and meticulously maintained, this 3-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and Eastern Shore charm. The spacious .35-acre property is surrounded by mature trees, creating peaceful wooded views from both the front and back of the home. Inside, you'll find luxury vinyl plank flooring throughout the main living areas in near-new condition, along with well-maintained carpeting in the bedrooms. Thoughtful updates include a water softener installed in 2024, a fenced yard added just two years ago, French drains, and two sump pumps designed to keep the property draining efficiently. An oversized shed provides excellent storage, while the deck offers the perfect place to enjoy your private outdoor setting. Life in Chesapeake Landing is all about enjoying nature and the water. Residents frequently spot deer, wild turkeys, turtles, and other local wildlife throughout this quiet, established neighborhood. There is no HOA, but the voluntary community association provides access to sought-after water amenities, including a community boat ramp, kayak launch, and fishing pier. The neighborhood also features Mill Brook Pond and the popular Turtle Walking Trail, giving residents even more opportunities to enjoy the outdoors. Located just minutes from historic Chestertown, you'll have easy access to everything that makes Kent County so special. Downtown Chestertown is only about seven minutes away and offers a vibrant year-round farmers market every Saturday from 9 a.m. to noon, locally owned shops, a beloved independent bookstore, and favorite dining destinations like Bad Alfred's Distilling. Also check out the sand bars at the marinas, perfect for waterfront happy hours. Whether you're drawn to the area's marinas, boating opportunities, charming small-town atmosphere, or the spacious homesites that provide room to breathe, this property delivers the true Eastern Shore lifestyle where water access is around every corner and community charm is abundant. If you've been searching for a home that combines modern convenience, natural beauty, and small-town waterfront living, 10572 Watonga Road is ready to welcome you home.

10572 Watonga Rd, Chestertown

Listing courtesy of Serhant. Contact:

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

Selling Office: Chesapeake Real Estate Associates, LLC.

3 Beds ⋅ 1 Baths

202 Valley Rd, Chestertown

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

Price improvement: Colonial in Kennedyville overlooking the pond. Situated on a corner lot with a private driveway behind the house. 2 car attached garage, 4 bedrooms and 2.5 baths. Gas fireplace. Large mudroom with laundry. Partially finished basement with new carpeting. Lovely front porch for relaxing and enjoying the view.

4 Beds ⋅ 3 Baths

Price improvement: Colonial in Kennedyville overlooking the pond. Situated on a corner lot with a private driveway behind the house. 2 car attached garage, 4 bedrooms and 2.5 baths. Gas fireplace. Large mudroom with laundry. Partially finished basement with new carpeting. Lovely front porch for relaxing and enjoying the view.

11942 Flour Mill St, Kennedyville

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

Selling Office: Douglas Realty LLC.

Great Chestertown location in College Heights. Large corner lot consisting of .51 acres. This home needs to be remodeled but has great potential and a lot of floor area. The old carpet has been removed down to sub flooring. Lovely sunporch, garage, off street driveway, and entrance courtyard are just a few features! Spacious rooms too! Close to Washington College, Downtown Chestertown, and Shopping Centers.

Great Chestertown location in College Heights. Large corner lot consisting of .51 acres. This home needs to be remodeled but has great potential and a lot of floor area. The old carpet has been removed down to sub flooring. Lovely sunporch, garage, off street driveway, and entrance courtyard are just a few features! Spacious rooms too! Close to Washington College, Downtown Chestertown, and Shopping Centers.

303 Cedar St, Chestertown

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

Selling Office: Cross Street Realtors LLC.

$324,000

Welcome to 102 Flying Cloud a new community known as The Village of Chestertown. This is a rare opportunity to own a home at this price and condition. Designed to with an open 1st floor features a bright white kitchen and dining area open to a large living room for entertaining and a 1/2 bathroom. The 2nd floor features 3 bedrooms 2 full bathrooms. The primary feature private bath and large closet. The exterior has large backyard for friends and family concrete driveway and freshly manicured yard. Call today for private showing today.

Welcome to 102 Flying Cloud a new community known as The Village of Chestertown. This is a rare opportunity to own a home at this price and condition. Designed to with an open 1st floor features a bright white kitchen and dining area open to a large living room for entertaining and a 1/2 bathroom. The 2nd floor features 3 bedrooms 2 full bathrooms. The primary feature private bath and large closet. The exterior has large backyard for friends and family concrete driveway and freshly manicured yard. Call today for private showing today.

102 Flying Cloud Dr, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$320,000

Welcome to Chesapeake Landing — where new construction meets timeless Cape Cod charm in the heart of Chestertown, MD. This brand-new 3 BR / 2.5 BA home at 10584 Klamath Rd by Roger Reed Builders (MD Lic. #2464) is move-in ready with quality finishes throughout. The open main level features luxury vinyl plank flooring, white shaker cabinets, granite countertops, a full stainless steel appliance package (side-by-side refrigerator with ice maker, over-range microwave, built-in dishwasher, smooth-surface electric range), and a convenient half bath. The primary suite offers a walk-in closet, ceiling fan, and en suite bath with granite vanity. Two additional bedrooms and a full bath with granite counters round out the upper level. Enjoy the ease of a private well and septic, 2½-ton heat pump, and no HOA. Gravel driveway, vinyl siding, 25-year shingles, and three black exterior lights give great curb appeal. Don't miss your chance to own a brand-new home in one of Kent County's sought-after communities!

Welcome to Chesapeake Landing — where new construction meets timeless Cape Cod charm in the heart of Chestertown, MD. This brand-new 3 BR / 2.5 BA home at 10584 Klamath Rd by Roger Reed Builders (MD Lic. #2464) is move-in ready with quality finishes throughout. The open main level features luxury vinyl plank flooring, white shaker cabinets, granite countertops, a full stainless steel appliance package (side-by-side refrigerator with ice maker, over-range microwave, built-in dishwasher, smooth-surface electric range), and a convenient half bath. The primary suite offers a walk-in closet, ceiling fan, and en suite bath with granite vanity. Two additional bedrooms and a full bath with granite counters round out the upper level. Enjoy the ease of a private well and septic, 2½-ton heat pump, and no HOA. Gravel driveway, vinyl siding, 25-year shingles, and three black exterior lights give great curb appeal. Don't miss your chance to own a brand-new home in one of Kent County's sought-after communities!

10584 Klamath Rd, Chestertown

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

Selling Office: Chesapeake Real Estate Associates, LLC.

$320,000

Welcome to Rigbie Bluff where coastal charm meets modern comfort. This two-bedroom, two-bath end-unit condominium is situated on the second floor - perfectly positioned to capture southern sunlight and breathtaking views of the Chesapeake Bay and Sassafras River. Delight in views of sailboats, yachts and ships crossing the Bay from the floor to ceiling sliding windows that line the living room and primary bedroom entrances to the spacious waterfront balcony that spans the entire rear wall of the unit. Inside you'll find a bright, open-concept living space featuring an updated kitchen, brand-new contemporary furnishings — most of which convey with the unit, a compact laundry and a primary bedroom suite with walk-in closet and attached bath. Every detail is designed for comfort and casual living; from the easy care engineered hardwood floors to the smart thermostat you can control from your phone, to the HVAC system and water heater which were both replaced within the last three years. Outside, enjoy your morning coffee on the balcony overlooking the Bay or take a short stroll to the community saltwater pool and private pier. The unit includes a deeded boat slip on the community pier and comes with a boat lift for easy access to open waters. On the lower level, you’ll find a spacious private storage area with its own separate entrance — ideal for bikes, kayaks and boating gear or use as a workshop area. Parking is effortless, with one reserved space directly in front of the unit and ample guest parking just steps away. This home is a short walk to Betterton Beach and one of the area’s finest waterfront gourmet restaurants. It's also close to Betterton's public tennis courts and playground. Together, condominium amenities and recreational facilities in the surrounding area offer something for everyone. Explore and enjoy local historic towns, nature parks and countless rivers, creeks, and coves the Eastern Shore waterfront has to offer — all from your own slice of paradise at Rigbie Bluff. Whether you are looking for a vacation getaway or a year-round residence, this lovely, move-in ready home delivers the best in year-round living comfort, convenience and coastal charm.

2 Beds ⋅ 2 Baths

Welcome to Rigbie Bluff where coastal charm meets modern comfort. This two-bedroom, two-bath end-unit condominium is situated on the second floor - perfectly positioned to capture southern sunlight and breathtaking views of the Chesapeake Bay and Sassafras River. Delight in views of sailboats, yachts and ships crossing the Bay from the floor to ceiling sliding windows that line the living room and primary bedroom entrances to the spacious waterfront balcony that spans the entire rear wall of the unit. Inside you'll find a bright, open-concept living space featuring an updated kitchen, brand-new contemporary furnishings — most of which convey with the unit, a compact laundry and a primary bedroom suite with walk-in closet and attached bath. Every detail is designed for comfort and casual living; from the easy care engineered hardwood floors to the smart thermostat you can control from your phone, to the HVAC system and water heater which were both replaced within the last three years. Outside, enjoy your morning coffee on the balcony overlooking the Bay or take a short stroll to the community saltwater pool and private pier. The unit includes a deeded boat slip on the community pier and comes with a boat lift for easy access to open waters. On the lower level, you’ll find a spacious private storage area with its own separate entrance — ideal for bikes, kayaks and boating gear or use as a workshop area. Parking is effortless, with one reserved space directly in front of the unit and ample guest parking just steps away. This home is a short walk to Betterton Beach and one of the area’s finest waterfront gourmet restaurants. It's also close to Betterton's public tennis courts and playground. Together, condominium amenities and recreational facilities in the surrounding area offer something for everyone. Explore and enjoy local historic towns, nature parks and countless rivers, creeks, and coves the Eastern Shore waterfront has to offer — all from your own slice of paradise at Rigbie Bluff. Whether you are looking for a vacation getaway or a year-round residence, this lovely, move-in ready home delivers the best in year-round living comfort, convenience and coastal charm.

10 Ericsson Ave Unit 31, Betterton

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

Selling Office: Berkshire Hathaway Homeservice Homesale Realty.

$320,000

Nestled in the serene countryside of Worton, Maryland, this charming 3 bed, 1 bath home offers the perfect balance of seclusion and convenience. Sitting on nearly half an acre, the property provides ample outdoor space, ideal for entertaining guests or simply relaxing in peace. Inside, you’ll find three cozy bedrooms and a full bathroom, while a large garage adds significant storage (or workshop) potential. Just a short drive away are the scenic shores of Rock Hall, public docks, and Lands’ End Vineyard & Winery, making this location a true gem for waterfront lovers and wine enthusiasts alike. Whether you're looking to host summer gatherings, enjoy weekend winery visits, or simply savor a peaceful lifestyle close to nature, this home delivers. Come see why this home is a rare find!

3 Beds ⋅ 1 Baths

Nestled in the serene countryside of Worton, Maryland, this charming 3 bed, 1 bath home offers the perfect balance of seclusion and convenience. Sitting on nearly half an acre, the property provides ample outdoor space, ideal for entertaining guests or simply relaxing in peace. Inside, you’ll find three cozy bedrooms and a full bathroom, while a large garage adds significant storage (or workshop) potential. Just a short drive away are the scenic shores of Rock Hall, public docks, and Lands’ End Vineyard & Winery, making this location a true gem for waterfront lovers and wine enthusiasts alike. Whether you're looking to host summer gatherings, enjoy weekend winery visits, or simply savor a peaceful lifestyle close to nature, this home delivers. Come see why this home is a rare find!

10444 Worton Rd, Worton

Listing courtesy of AB & Co Realtors, Inc.. Contact:

Selling Office: Doug Ashley Realtors, LLC.

$319,500

This farmhouse-style home is nestled in the heart of Kennedyville’s rural farmland and combines original character with tasteful upgrades. The property offers 3 bedrooms and 2.5 baths, including a first-floor bedroom with French doors leading to the rear yard. Inside, you’ll find wide-plank hardwood floors throughout, detailed woodwork, built-ins, and naturally bright rooms. The main level includes a full bath, office, and a foyer with new cabinetry and additional access to the side and rear yards. Upstairs, the second floor provides a bedroom with a large walk-in closet and full bath, while the third floor offers a flexible space that could be used as a bedroom, home gym, library, or craft room. The outdoor areas are well-suited for both relaxation and activity, with space for gardening, gatherings around a bonfire, or simply enjoying panoramic views of the surrounding farmland. A covered front porch adds to the home’s welcoming appeal. Recent upgrades by the current owners include all new windows with a transferable warranty, a new water system, new cabinetry in the hall, and a new Thor stove. Conveniently located, the property is within close proximity to Middletown, Chestertown, and multiple public landings throughout Kent County.

This farmhouse-style home is nestled in the heart of Kennedyville’s rural farmland and combines original character with tasteful upgrades. The property offers 3 bedrooms and 2.5 baths, including a first-floor bedroom with French doors leading to the rear yard. Inside, you’ll find wide-plank hardwood floors throughout, detailed woodwork, built-ins, and naturally bright rooms. The main level includes a full bath, office, and a foyer with new cabinetry and additional access to the side and rear yards. Upstairs, the second floor provides a bedroom with a large walk-in closet and full bath, while the third floor offers a flexible space that could be used as a bedroom, home gym, library, or craft room. The outdoor areas are well-suited for both relaxation and activity, with space for gardening, gatherings around a bonfire, or simply enjoying panoramic views of the surrounding farmland. A covered front porch adds to the home’s welcoming appeal. Recent upgrades by the current owners include all new windows with a transferable warranty, a new water system, new cabinetry in the hall, and a new Thor stove. Conveniently located, the property is within close proximity to Middletown, Chestertown, and multiple public landings throughout Kent County.

29380 Old Locust Grove Rd, Kennedyville

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

11969 Augustine Herman Hwy, Kennedyville

$319,000

Vintage home with lots of original details retained. 3 Staircases, 3 original fireplaces and a very grand front foyer and staircase give this home so much character! Current owners have updated it lovingly throughout. Enter through the spacious back yard, into a welcoming mudroom with a full bath on the main floor to your left and then into the updated and cozy kitchen with new dishwasher, LVP flooring, complete with the cutest back stair case! The staircase leads up to a separate home office, craft room, den, or 4th bedroom. Also downstairs is a main floor bedroom, a nice size dining room with decorative fireplace and parquet flooring, and a Living room with new carpet, and a new pellet stove to keep you warm on those chilly nights. On the 2nd level are 2 bedrooms plus the office, and a full bathroom. Full stairs to the 3rd floor leads to 2 additional rooms that could easily be finished into more living space. Since 2018 the current owners have updated the home to include: New Roof on 2 sections of house and roof repairs to existing roof (only 10 years old), all New windows (5) on third floor, encapsulated crawl space, new Oil Furnace, 2 new water heaters (one serves upstairs bathroom only). New dishwasher, blown in insulation in all internal ceilings and attic, new flooring downstairs, kitchen and bathroom updates, and so much more! Outside is a very private oasis. Completely fenced in yard with large covered side porch and open back deck looking out to a manicured lawn with large shed and nice plantings. Back gate leads to gravel driveway, parking for 2-4 cars The home is very versitile. Village zoning allows for commercial use as well. In the past it has been an antique/retail store, but please verify any possible uses with the county first.

4 Beds ⋅ 2 Baths

Vintage home with lots of original details retained. 3 Staircases, 3 original fireplaces and a very grand front foyer and staircase give this home so much character! Current owners have updated it lovingly throughout. Enter through the spacious back yard, into a welcoming mudroom with a full bath on the main floor to your left and then into the updated and cozy kitchen with new dishwasher, LVP flooring, complete with the cutest back stair case! The staircase leads up to a separate home office, craft room, den, or 4th bedroom. Also downstairs is a main floor bedroom, a nice size dining room with decorative fireplace and parquet flooring, and a Living room with new carpet, and a new pellet stove to keep you warm on those chilly nights. On the 2nd level are 2 bedrooms plus the office, and a full bathroom. Full stairs to the 3rd floor leads to 2 additional rooms that could easily be finished into more living space. Since 2018 the current owners have updated the home to include: New Roof on 2 sections of house and roof repairs to existing roof (only 10 years old), all New windows (5) on third floor, encapsulated crawl space, new Oil Furnace, 2 new water heaters (one serves upstairs bathroom only). New dishwasher, blown in insulation in all internal ceilings and attic, new flooring downstairs, kitchen and bathroom updates, and so much more! Outside is a very private oasis. Completely fenced in yard with large covered side porch and open back deck looking out to a manicured lawn with large shed and nice plantings. Back gate leads to gravel driveway, parking for 2-4 cars The home is very versitile. Village zoning allows for commercial use as well. In the past it has been an antique/retail store, but please verify any possible uses with the county first.

11969 Augustine Herman Hwy, Kennedyville

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

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

$318,000

Charming Single-Level Home in the Heart of Walkable Chestertown. Welcome to one of Chestertown's most convenient addresses — a quaint, single-level, three-bedroom home set on a large, shaded yard just a few flat blocks from Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, locally loved restaurants, and everyday groceries. The location is the kind that sells itself: leave the car in the driveway and run the day on foot, from morning coffee downtown to an evening stroll after the festivals. Inside, the sun-filled sunroom anchors the home with year-round natural light and a flexible layout that adapts to how you actually live. Use it as a quiet reading nook, a bright home office, an art studio, or simply a place to begin and end each day. The three-bedroom, single-level floor plan delivers true main-level living with no stairs and no wasted square footage, an increasingly rare find in historic Chestertown. The HVAC has been recently updated, providing year-round comfort, modern efficiency, and predictable utility costs for new owners. Step outside to a generous, tree-shaded yard offering a level of privacy and outdoor space uncommon to a home this close to downtown. There's room to garden, host family dinners, let pets roam, or simply enjoy a quiet afternoon in the shade. The setting feels tucked away while the rest of the town is just a short walk from your front door. For weekend owners, the home offers true lock-and-leave simplicity. For full-time residents, it offers the daily rhythm of a small college town with a real cultural calendar, a thriving farmers market, and a walkable downtown filled with independent shops and restaurants. Fiber optic internet is available at the property, supporting fast, reliable connectivity for remote work, streaming, and study without compromise. Single-level, move-in ready, and walkable to it all — a rare combination in this small, storybook college town. The home suits a wide range of buyers, from first-time homeowners and downsizers to weekend retreat owners and anyone seeking a quieter life with genuine connection to community. Schedule your private tour today!

Charming Single-Level Home in the Heart of Walkable Chestertown. Welcome to one of Chestertown's most convenient addresses — a quaint, single-level, three-bedroom home set on a large, shaded yard just a few flat blocks from Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, locally loved restaurants, and everyday groceries. The location is the kind that sells itself: leave the car in the driveway and run the day on foot, from morning coffee downtown to an evening stroll after the festivals. Inside, the sun-filled sunroom anchors the home with year-round natural light and a flexible layout that adapts to how you actually live. Use it as a quiet reading nook, a bright home office, an art studio, or simply a place to begin and end each day. The three-bedroom, single-level floor plan delivers true main-level living with no stairs and no wasted square footage, an increasingly rare find in historic Chestertown. The HVAC has been recently updated, providing year-round comfort, modern efficiency, and predictable utility costs for new owners. Step outside to a generous, tree-shaded yard offering a level of privacy and outdoor space uncommon to a home this close to downtown. There's room to garden, host family dinners, let pets roam, or simply enjoy a quiet afternoon in the shade. The setting feels tucked away while the rest of the town is just a short walk from your front door. For weekend owners, the home offers true lock-and-leave simplicity. For full-time residents, it offers the daily rhythm of a small college town with a real cultural calendar, a thriving farmers market, and a walkable downtown filled with independent shops and restaurants. Fiber optic internet is available at the property, supporting fast, reliable connectivity for remote work, streaming, and study without compromise. Single-level, move-in ready, and walkable to it all — a rare combination in this small, storybook college town. The home suits a wide range of buyers, from first-time homeowners and downsizers to weekend retreat owners and anyone seeking a quieter life with genuine connection to community. Schedule your private tour today!

109 Cedar St, Chestertown

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

Selling Office: Chesapeake Real Estate Associates, LLC.

$317,000

Welcome to your new home in the historic harbor town of Rock Hall! Quality new construction built with meticulous attention to detail. This 3 bedroom/2 bath home is clean and sleek with modern, tasteful upgrades and color palette. Every appliance and ammenity is brand new, from the HVAC to the bathroom vanities and recessed lighting. Any chef would be thrilled with this substantial kitchen offering granite counters, build-in cabinetry, stainless steel appliances and generous-sized center island. Stylishly appointed baths feature plumbing, fixtures and lighting. The large master bedroom has its own bathroom and a walk-in closet. 2 additonal bedrooms complete the layout. Enjoy a beverage on the 20 X 10 deck on the rear exterior. Rock Hall is a small, eastern shore community with miles of Chesapeake Bay shoreline and unspoiled wildlife. Renowned for its boating opportunities, Rock Hall also offers quaint restaurants, museums and local shops.

Welcome to your new home in the historic harbor town of Rock Hall! Quality new construction built with meticulous attention to detail. This 3 bedroom/2 bath home is clean and sleek with modern, tasteful upgrades and color palette. Every appliance and ammenity is brand new, from the HVAC to the bathroom vanities and recessed lighting. Any chef would be thrilled with this substantial kitchen offering granite counters, build-in cabinetry, stainless steel appliances and generous-sized center island. Stylishly appointed baths feature plumbing, fixtures and lighting. The large master bedroom has its own bathroom and a walk-in closet. 2 additonal bedrooms complete the layout. Enjoy a beverage on the 20 X 10 deck on the rear exterior. Rock Hall is a small, eastern shore community with miles of Chesapeake Bay shoreline and unspoiled wildlife. Renowned for its boating opportunities, Rock Hall also offers quaint restaurants, museums and local shops.

4921 Piney Neck Rd, Rock Hall

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact:

Selling Office: Rock Hall Properties Real Estate.

$316,000

Welcome to 10720 Foreston Rd, a charming and inviting home situated in the peaceful surroundings of Chesapeake Landing in Chestertown, MD. 3 bedrooms and 2 full bathrooms with a spacious eat-in kitchen and generous living room provides ample room for comfortable living. Move-in ready condition. Inside, you'll immediately notice the warmth and character of the stunning hardwood floors that flow throughout the home. The open and airy layout ensures a seamless flow between the living spaces, making it perfect for entertaining or just relaxing at home. The well-equipped laundry area comes complete with both a washer and dryer for added convenience. Take full advantage of the outdoor amenities this property has to offer. Start your mornings with coffee on the cozy screened porch or wind down your evenings on the expansive deck overlooking the fenced yard. There's plenty of space to garden, play, or simply enjoy the outdoors in privacy. The property also includes a garage, providing extra storage space and parking. This home is ideal for those seeking both charm and functionality in a serene setting. Don't miss the opportunity to call 10720 Foreston Rd your new home. Schedule your showing today to experience all that this property has to offer!

Welcome to 10720 Foreston Rd, a charming and inviting home situated in the peaceful surroundings of Chesapeake Landing in Chestertown, MD. 3 bedrooms and 2 full bathrooms with a spacious eat-in kitchen and generous living room provides ample room for comfortable living. Move-in ready condition. Inside, you'll immediately notice the warmth and character of the stunning hardwood floors that flow throughout the home. The open and airy layout ensures a seamless flow between the living spaces, making it perfect for entertaining or just relaxing at home. The well-equipped laundry area comes complete with both a washer and dryer for added convenience. Take full advantage of the outdoor amenities this property has to offer. Start your mornings with coffee on the cozy screened porch or wind down your evenings on the expansive deck overlooking the fenced yard. There's plenty of space to garden, play, or simply enjoy the outdoors in privacy. The property also includes a garage, providing extra storage space and parking. This home is ideal for those seeking both charm and functionality in a serene setting. Don't miss the opportunity to call 10720 Foreston Rd your new home. Schedule your showing today to experience all that this property has to offer!

10720 Foreston Rd, Chestertown

Listing courtesy of Compass. Contact:

Selling Office: Taylor Properties.

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!

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:

Selling Office: Rock Hall Properties Real Estate.

136 N Main St is Coming Soon in Galena! Your next home may be closer than you think. This inviting Colonial combines classic character with thoughtful updates across nearly 1,900 square feet of living space. Inside, you'll find three comfortable bedrooms, one full bath upstairs, a convenient main-level half bath, a bright kitchen with an easy flow into the main living areas, and a dedicated laundry/mudroom that adds everyday convenience. Outside, the fully fenced backyard offers exceptional space to enjoy, complete with mature shade trees, a fire pit, a storage shed, and plenty of room for outdoor gatherings, gardening, pets, or play. A large paved driveway provides abundant off-street parking. Conveniently located near Rt. 301, Chestertown, Middletown, local marinas, shopping, and dining, this home offers the charm of small-town living with easy access to everyday essentials. Stay tuned, you'll want to be among the first to see it when it hits the market.

136 N Main St is Coming Soon in Galena! Your next home may be closer than you think. This inviting Colonial combines classic character with thoughtful updates across nearly 1,900 square feet of living space. Inside, you'll find three comfortable bedrooms, one full bath upstairs, a convenient main-level half bath, a bright kitchen with an easy flow into the main living areas, and a dedicated laundry/mudroom that adds everyday convenience. Outside, the fully fenced backyard offers exceptional space to enjoy, complete with mature shade trees, a fire pit, a storage shed, and plenty of room for outdoor gatherings, gardening, pets, or play. A large paved driveway provides abundant off-street parking. Conveniently located near Rt. 301, Chestertown, Middletown, local marinas, shopping, and dining, this home offers the charm of small-town living with easy access to everyday essentials. Stay tuned, you'll want to be among the first to see it when it hits the market.

136 N Main St, Galena

Listing courtesy of Keller Williams Legacy. Contact:

Selling Office: EXP Realty, LLC.

Welcome to 11976 Flour Mill Street in the charming Village at Kennedyville! Nestled in the heart of this small-town community, this well-maintained 3-bedroom, 2-bath rancher offers comfortable one-level living with an inviting open floor plan perfect for everyday living and entertaining alike. Enjoy relaxing mornings on the welcoming front porch or unwind on the spacious back deck overlooking the backyard. Conveniently located just a short drive to Route 301 for easy northbound or southbound travel, while also being close to the historic waterfront town of Chestertown with its local shops, restaurants, and community events. If you are looking for small-town charm with convenience, this home is a must-see!

Welcome to 11976 Flour Mill Street in the charming Village at Kennedyville! Nestled in the heart of this small-town community, this well-maintained 3-bedroom, 2-bath rancher offers comfortable one-level living with an inviting open floor plan perfect for everyday living and entertaining alike. Enjoy relaxing mornings on the welcoming front porch or unwind on the spacious back deck overlooking the backyard. Conveniently located just a short drive to Route 301 for easy northbound or southbound travel, while also being close to the historic waterfront town of Chestertown with its local shops, restaurants, and community events. If you are looking for small-town charm with convenience, this home is a must-see!

11976 Flour Mill St, Kennedyville

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

Selling Office: Unrepresented.

Welcome to 10 Ericsson Ave #33 in the waterfront community of Betterton, where everyday living feels like a permanent getaway. Nestled within the peaceful enclave of Rigbie Bluff, this inviting, updated, and move-in ready condo offers a rare blend of tranquility, charm, and scenic beauty. This well-appointed two-bedroom, two-bath residence is conveniently located on the ground level, making move-in effortless and everyday living easily accessible. Inside, you’ll find a comfortable layout designed for relaxation after a day spent enjoying the water and surrounding nature. Wake up each morning to sweeping views of the Chesapeake Bay, where sailboats drift by and maritime traffic creates an ever-changing coastal backdrop. Whether you're enjoying your morning coffee or unwinding at sunset, the water views and natural surroundings provide a constant sense of calm. For boating enthusiasts, the deeded private boat slip with hoist makes it simple to hop on your boat and cruise the bay at a moment’s notice. Spend your days exploring the shoreline, fishing, or enjoying endless waterfront adventures just steps from your door. Rigbie Bluff is known for its relaxed, small-town atmosphere—perfect for those seeking a slower pace without sacrificing connection. Enjoy time by the community pool, where you can unwind, soak up the sun, and let your worries drift away. This remarkable condo is ready for you to experience all that Betterton and the Chesapeake Bay have to offer—whether as a full-time residence or the perfect weekend escape. Come discover a place where serenity, community, and coastal living come together effortlessly.

2 Beds ⋅ 2 Baths

Welcome to 10 Ericsson Ave #33 in the waterfront community of Betterton, where everyday living feels like a permanent getaway. Nestled within the peaceful enclave of Rigbie Bluff, this inviting, updated, and move-in ready condo offers a rare blend of tranquility, charm, and scenic beauty. This well-appointed two-bedroom, two-bath residence is conveniently located on the ground level, making move-in effortless and everyday living easily accessible. Inside, you’ll find a comfortable layout designed for relaxation after a day spent enjoying the water and surrounding nature. Wake up each morning to sweeping views of the Chesapeake Bay, where sailboats drift by and maritime traffic creates an ever-changing coastal backdrop. Whether you're enjoying your morning coffee or unwinding at sunset, the water views and natural surroundings provide a constant sense of calm. For boating enthusiasts, the deeded private boat slip with hoist makes it simple to hop on your boat and cruise the bay at a moment’s notice. Spend your days exploring the shoreline, fishing, or enjoying endless waterfront adventures just steps from your door. Rigbie Bluff is known for its relaxed, small-town atmosphere—perfect for those seeking a slower pace without sacrificing connection. Enjoy time by the community pool, where you can unwind, soak up the sun, and let your worries drift away. This remarkable condo is ready for you to experience all that Betterton and the Chesapeake Bay have to offer—whether as a full-time residence or the perfect weekend escape. Come discover a place where serenity, community, and coastal living come together effortlessly.

10 Ericsson Ave Unit 33, Betterton

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

Selling Office: ExecuHome Realty.

Beach day… or boat day.......maybe pool day? 🌊🚤 Welcome to the “Jewel of the Chesapeake” in charming Betterton—where the Eastern Shore of Maryland living meets effortless waterfront luxury. This condo is perfectly positioned with breathtaking views of Betterton Beach and the expansive Chesapeake Bay, right at the mouth of the Sassafras River. Step inside this inviting 2-bedroom, 2 full bath end-unit condo, where additional windows invite in natural light and frame the surrounding water views. The open-concept living, dining, and kitchen areas create an effortless flow—ideal for both everyday living and entertaining. Slide open the doors and step onto your expansive private balcony, where panoramic water views and vibrant sunsets set the tone. Let the rhythm of the waves and the distant call of bald eagles become the soundtrack to your mornings and evenings—an experience that simply can’t be replicated. 🌅🦅 For the boating enthusiast, this is truly exceptional—a private HOA pier, your own boat slip, AND a boat lift all convey with the sale. From kayaking and paddleboarding to waterskiing and cruising the Bay, everything you love about waterfront living is just steps away—from your balcony to the beach in under 60 seconds. 🚤 The community also offers access to a private saltwater pool, creating a rare combination of beach, boating, and poolside living all in one location. 🏊‍♀️ Thoughtfully updated, this home features new flooring throughout, updated kitchen appliances with a stylish backsplash, and a NEW HVAC system (Fall 2025)—offering comfort and peace of mind for the next owner. Ohhh and did I mention a huge storage room right below your unit for all your water toys & more? Betterton is known for its welcoming charm, scenic shoreline, and seasonal events. Enjoy summer days filled with beachside relaxation, waterfront activities, holiday fireworks, and beloved traditions like Betterton Appreciation Days—all just moments from your door. 💫 Priced at $315,000, this is a standout opportunity to secure a waterfront lifestyle just in time to enjoy the full summer season. 📅 Open House: Sunday, April 12th | 11:00 AM – 1:00 PM A rare offering combining location, lifestyle, and value—schedule your showing before it’s gone.

2 Beds ⋅ 2 Baths

Beach day… or boat day.......maybe pool day? 🌊🚤 Welcome to the “Jewel of the Chesapeake” in charming Betterton—where the Eastern Shore of Maryland living meets effortless waterfront luxury. This condo is perfectly positioned with breathtaking views of Betterton Beach and the expansive Chesapeake Bay, right at the mouth of the Sassafras River. Step inside this inviting 2-bedroom, 2 full bath end-unit condo, where additional windows invite in natural light and frame the surrounding water views. The open-concept living, dining, and kitchen areas create an effortless flow—ideal for both everyday living and entertaining. Slide open the doors and step onto your expansive private balcony, where panoramic water views and vibrant sunsets set the tone. Let the rhythm of the waves and the distant call of bald eagles become the soundtrack to your mornings and evenings—an experience that simply can’t be replicated. 🌅🦅 For the boating enthusiast, this is truly exceptional—a private HOA pier, your own boat slip, AND a boat lift all convey with the sale. From kayaking and paddleboarding to waterskiing and cruising the Bay, everything you love about waterfront living is just steps away—from your balcony to the beach in under 60 seconds. 🚤 The community also offers access to a private saltwater pool, creating a rare combination of beach, boating, and poolside living all in one location. 🏊‍♀️ Thoughtfully updated, this home features new flooring throughout, updated kitchen appliances with a stylish backsplash, and a NEW HVAC system (Fall 2025)—offering comfort and peace of mind for the next owner. Ohhh and did I mention a huge storage room right below your unit for all your water toys & more? Betterton is known for its welcoming charm, scenic shoreline, and seasonal events. Enjoy summer days filled with beachside relaxation, waterfront activities, holiday fireworks, and beloved traditions like Betterton Appreciation Days—all just moments from your door. 💫 Priced at $315,000, this is a standout opportunity to secure a waterfront lifestyle just in time to enjoy the full summer season. 📅 Open House: Sunday, April 12th | 11:00 AM – 1:00 PM A rare offering combining location, lifestyle, and value—schedule your showing before it’s gone.

10 Ericsson Ave Unit 37, Betterton

Listing courtesy of Remax Vision. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

Check out this Like New , MOVE IN READY Rancher with an Amazing view ! This beautiful 3-bedroom, 2-bathroom residence offers quality craftsmanship and tasteful upgrades throughout. From the granite countertops to the designer bathroom vanities and recessed lighting, every detail has been carefully selected for both style and function. The kitchen is a standout feature—complete with stainless steel appliances, custom cabinetry, and a center island topped with gleaming granite—perfect for entertaining or everyday living. The spacious primary suite includes a private bath and walk-in closet, offering comfort and convenience. Enjoy peaceful pastoral views of farmland, a pond, and mature trees from your property—ideal for those who appreciate a tranquil setting. The Back Deck was built to higher standards with additional supports & permitted to allow for a HotTub to be placed on the left side. New Large Shed has room for all your toys and lawn equipment. This thoughtfully built home combines modern features with timeless appeal—don’t miss the opportunity to make it yours! Please note: a front foot fee will be assessed for public water and sewer as noted in the disclosures

Check out this Like New , MOVE IN READY Rancher with an Amazing view ! This beautiful 3-bedroom, 2-bathroom residence offers quality craftsmanship and tasteful upgrades throughout. From the granite countertops to the designer bathroom vanities and recessed lighting, every detail has been carefully selected for both style and function. The kitchen is a standout feature—complete with stainless steel appliances, custom cabinetry, and a center island topped with gleaming granite—perfect for entertaining or everyday living. The spacious primary suite includes a private bath and walk-in closet, offering comfort and convenience. Enjoy peaceful pastoral views of farmland, a pond, and mature trees from your property—ideal for those who appreciate a tranquil setting. The Back Deck was built to higher standards with additional supports & permitted to allow for a HotTub to be placed on the left side. New Large Shed has room for all your toys and lawn equipment. This thoughtfully built home combines modern features with timeless appeal—don’t miss the opportunity to make it yours! Please note: a front foot fee will be assessed for public water and sewer as noted in the disclosures

11047 Bottom Rd, Worton

Listing courtesy of Taylor Properties. Contact:

Selling Office: Berkshire Hathaway HomeServices Homesale Realty.

Welcome to the charming town of Betterton. Located along the Chesapeake Bay with a nice sandy Beach. Staycation! You will feel like your on vacation while you live here at 200 Ericcson Ave. This 3 Bedroom, 2 Bath has all you need to Relax and Enjoy. Located on a nice corner lot, This Turn Key Home is in Great condition with low maintenance allowing you to enjoy the percs of the area. Large living room, Primary Bedroom has a large En Suite Bath. Out side is a Great Screen Gazebo with an ajoining patio for your next crab feast, Large Quonset hut style building for garage, shop or studio, Multiple sheds for storage and back up generator shed. All this for a Great Price. Schedule your showing soon before this fish gets away.

Welcome to the charming town of Betterton. Located along the Chesapeake Bay with a nice sandy Beach. Staycation! You will feel like your on vacation while you live here at 200 Ericcson Ave. This 3 Bedroom, 2 Bath has all you need to Relax and Enjoy. Located on a nice corner lot, This Turn Key Home is in Great condition with low maintenance allowing you to enjoy the percs of the area. Large living room, Primary Bedroom has a large En Suite Bath. Out side is a Great Screen Gazebo with an ajoining patio for your next crab feast, Large Quonset hut style building for garage, shop or studio, Multiple sheds for storage and back up generator shed. All this for a Great Price. Schedule your showing soon before this fish gets away.

200 Ericsson Ave, Betterton

Listing courtesy of Key Realty, Incorporated. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$310,000

Fantastic townhouse nestled in the heart of the water-oriented community of Rock Hall. This duplex has three bedroom suites and is being sold with contents, fully furnished. Currently used as a vacation rental, this townhouse is ready to go! There is an entry level bedroom with attached half bath and access to a scenic screened porch. The first level has a one car garage, perfect for extra storage. The main living level is an open floor plan, perfect for entertaining and gatherings. There is a half bath and an open-air spacious deck off of the kitchen, peacefully nestled facing the trees. Hence it's name, Tree House! Great natural views. The third floor boasts two bedrooms, each with their own full baths. This property is located in the Watermans Estates community, which is just around the block from Main Street shops, great restaurants and marinas. Most importantly, this home is only a short distance away from the Rock Hall Harbor and Chesapeake Bay. Great fireworks displays, festivities and all Rock Hall has to offer just around the corner!

3 Beds ⋅ 4 Baths

Fantastic townhouse nestled in the heart of the water-oriented community of Rock Hall. This duplex has three bedroom suites and is being sold with contents, fully furnished. Currently used as a vacation rental, this townhouse is ready to go! There is an entry level bedroom with attached half bath and access to a scenic screened porch. The first level has a one car garage, perfect for extra storage. The main living level is an open floor plan, perfect for entertaining and gatherings. There is a half bath and an open-air spacious deck off of the kitchen, peacefully nestled facing the trees. Hence it's name, Tree House! Great natural views. The third floor boasts two bedrooms, each with their own full baths. This property is located in the Watermans Estates community, which is just around the block from Main Street shops, great restaurants and marinas. Most importantly, this home is only a short distance away from the Rock Hall Harbor and Chesapeake Bay. Great fireworks displays, festivities and all Rock Hall has to offer just around the corner!

21119 Striper Run, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Gunther-McClary Real Estate.

$309,000

Welcome to 12776 Still Pond Road: an endearing early 20th Century Victorian in the quiet town of Still Pond. This could be the perfect Eastern Shore retreat or full time residence. Historic Charm abounds with pocket doors, bay windows, 9 foot ceilings, hardwood floors, bullseye corner moldings, mahogany front porch, oak mantels, custom built-ins, and so much more. Enjoy rolling farmland views and picturesque sunsets from the front porch swinging bench. The sun-filled formal parlor flows seamlessly through the large pocket door into the dining room and kitchen. Follow the solid-wood staircase and railing upstairs to find 3 generously sized bedrooms and a 4th bedroom or office space. Massive 3rd floor could be finished for a 4th bedroom or den / game room. Recent upgrades include: architectural shingle roof, 6 mini-split systems for central heating and air, water conditioner, water heater, fireplace mantel with propane insert, and a brand new Fuji septic system. Almost 3/4 of an acre allows plenty of space for the dogs and kids to play. Open farmland surrounds for great views from any direction. Less than 90 minutes to Philadelphia and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Close to Turners Creek State Park, Betterton Beach and the restaurants/marinas in Galena on the Sassafras River. Quick drive to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market, and a brand new YMCA with full gym, racquet sports, lap pool, sauna, etc. Enjoy country living on the Eastern Shore.

Welcome to 12776 Still Pond Road: an endearing early 20th Century Victorian in the quiet town of Still Pond. This could be the perfect Eastern Shore retreat or full time residence. Historic Charm abounds with pocket doors, bay windows, 9 foot ceilings, hardwood floors, bullseye corner moldings, mahogany front porch, oak mantels, custom built-ins, and so much more. Enjoy rolling farmland views and picturesque sunsets from the front porch swinging bench. The sun-filled formal parlor flows seamlessly through the large pocket door into the dining room and kitchen. Follow the solid-wood staircase and railing upstairs to find 3 generously sized bedrooms and a 4th bedroom or office space. Massive 3rd floor could be finished for a 4th bedroom or den / game room. Recent upgrades include: architectural shingle roof, 6 mini-split systems for central heating and air, water conditioner, water heater, fireplace mantel with propane insert, and a brand new Fuji septic system. Almost 3/4 of an acre allows plenty of space for the dogs and kids to play. Open farmland surrounds for great views from any direction. Less than 90 minutes to Philadelphia and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Close to Turners Creek State Park, Betterton Beach and the restaurants/marinas in Galena on the Sassafras River. Quick drive to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market, and a brand new YMCA with full gym, racquet sports, lap pool, sauna, etc. Enjoy country living on the Eastern Shore.

12776 Still Pond Rd, Still Pond

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

Selling Office: Chesapeake Real Estate Associates, LLC.

$307,000

Welcome to this beautifully renovated 3-bedroom, 1.5-bath rancher set on a half-acre lot just 1.5 miles from downtown Rock Hall. Fully updated in 2020, this home features an open floor plan that flows seamlessly from the kitchen through the living room to a charming deck overlooking the backyard. With two fireplaces—one in the family room and one in the living room—you’ll enjoy cozy focal points throughout the home. The attached one-car carport adds convenience, while the large lot offers the perfect balance of indoor comfort and outdoor living.

Welcome to this beautifully renovated 3-bedroom, 1.5-bath rancher set on a half-acre lot just 1.5 miles from downtown Rock Hall. Fully updated in 2020, this home features an open floor plan that flows seamlessly from the kitchen through the living room to a charming deck overlooking the backyard. With two fireplaces—one in the family room and one in the living room—you’ll enjoy cozy focal points throughout the home. The attached one-car carport adds convenience, while the large lot offers the perfect balance of indoor comfort and outdoor living.

6345 Rock Hall Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Unrepresented Buyer Office.

$306,000

Updated in 2024 by a loving family member & their licensed professional! This charming 3-bedroom, 2-bath home offers a perfect blend of modern updates and country serenity. The main level features a convenient first-floor bedroom and full bath, ideal for aging in place. Enjoy stylish & durable vinyl plank flooring throughout and soaring cathedral ceilings upstairs that create an airy, open feel. Situated on a spacious corner lot on almost a half of an acre & a newly installed well. Whether it’s a morning coffee or an evening cocktail for watching sunsets, enjoy the cozy front porch where you can relax and take in the sweeping views of the surrounding farmland. A peaceful retreat with thoughtful upgrades—move-in ready and waiting for you! - Buyer got cold feet, walked and never scheduled inspections , terminated in default and forfeited their EMD -