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$1,195,000

Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring upgraded countertops and a spacious island, flows seamlessly into the family room, perfect for entertaining. Relax in the primary suite with a lavish bath or unwind in the inviting family room by the fireplace with views out to Crab Alley. Three additional bedrooms (or two bedrooms and an office) and two baths round out the main level that offers sweeping scenic views from every vantage point. Step outside to discover a private oasis on 1.25 acres, complete with extensive hardscaping, a heated in-ground pool, and a soothing hot tub. Enjoy picturesque water views out the front and back, with access for kayaking and boating. The community amenities, including a beach, clubhouse, and tennis courts, elevate your living experience. This home is not just a residence; it's a lifestyle waiting to be embraced and enjoyed. Start living your best 'Shore Life' at 2855 Cox Neck Rd.

4 Beds ⋅ 5 Baths ⋅ MDQA2016942 MLS

Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring upgraded countertops and a spacious island, flows seamlessly into the family room, perfect for entertaining. Relax in the primary suite with a lavish bath or unwind in the inviting family room by the fireplace with views out to Crab Alley. Three additional bedrooms (or two bedrooms and an office) and two baths round out the main level that offers sweeping scenic views from every vantage point. Step outside to discover a private oasis on 1.25 acres, complete with extensive hardscaping, a heated in-ground pool, and a soothing hot tub. Enjoy picturesque water views out the front and back, with access for kayaking and boating. The community amenities, including a beach, clubhouse, and tennis courts, elevate your living experience. This home is not just a residence; it's a lifestyle waiting to be embraced and enjoyed. Start living your best 'Shore Life' at 2855 Cox Neck Rd.

2855 Cox Neck Rd, Chester

$875,000

The Conklin House: A Masterpiece of History & Modern Luxury. Experience the perfect blend of early 20th-century charm and 21st-century comfort. The Conklin House, a classic 1908 Queen Anne Victorian, stands as a commanding presence at the edge of the historic Village of Sugar Loaf. The home has always been used residentially but zoning permits commercial usage as well. Originally ordered from the Sears & Roebuck catalogue and delivered by rail, this "pre-fab" pioneer was famously the first electrified home in the area. The current owner has meticulously performed a full-scale reconstruction, ensuring the home is entirely turn-key while honoring its heritage. The home features modern infrastructure with all-new mechanical systems, walls, and energy-efficient windows. Its preserved character is astounding. Every period molding, the original grand staircase, panel doors and authentic flooring have been salvaged and restored. The architectural heritage is monumental as it features its signature steeply pitched hipped roof and a dominant front-facing gable that defines its Victorian silhouette. Built for Howard Conklin—the local postmaster/general store owner—and later by his son, Dr. Roger Howard Conklin, this residence has been a cornerstone of the community for over a century. It represents a rare opportunity to own a piece of Hudson Valley history without the burden of historic maintenance. The lifestyle in Sugar Loaf and Chester, NY is refreshing, especially to New Yorkers getting away from the city. Nestled in a tight-knit arts and crafts hamlet, one is steps away from 18th-century buildings housing artisan studios, galleries, and boutique eateries. And there is rich Outdoor Adventure to take advantage of too! The area has direct access to the 18-mile Heritage Trail for biking and walking, plus proximity to Goosepond Mountain State Park and the Birnberg Nature Preserve. Its rural serenity offers a quiet, creative lifestyle surrounded by majestic mountains and rolling meadows, all while being part of a bustling weekend destination. Driving to and from the Conklin House to NYC is about 1 hour and 15 minutes and using mass transit a little longer. This is more than a house; it is a storied landmark reimagined for the modern connoisseur. Nothing compares to the character, lifestyle and wilderness that the Conklin House has to offer.

3 Beds ⋅ 3 Baths ⋅ 974429 MLS

The Conklin House: A Masterpiece of History & Modern Luxury. Experience the perfect blend of early 20th-century charm and 21st-century comfort. The Conklin House, a classic 1908 Queen Anne Victorian, stands as a commanding presence at the edge of the historic Village of Sugar Loaf. The home has always been used residentially but zoning permits commercial usage as well. Originally ordered from the Sears & Roebuck catalogue and delivered by rail, this "pre-fab" pioneer was famously the first electrified home in the area. The current owner has meticulously performed a full-scale reconstruction, ensuring the home is entirely turn-key while honoring its heritage. The home features modern infrastructure with all-new mechanical systems, walls, and energy-efficient windows. Its preserved character is astounding. Every period molding, the original grand staircase, panel doors and authentic flooring have been salvaged and restored. The architectural heritage is monumental as it features its signature steeply pitched hipped roof and a dominant front-facing gable that defines its Victorian silhouette. Built for Howard Conklin—the local postmaster/general store owner—and later by his son, Dr. Roger Howard Conklin, this residence has been a cornerstone of the community for over a century. It represents a rare opportunity to own a piece of Hudson Valley history without the burden of historic maintenance. The lifestyle in Sugar Loaf and Chester, NY is refreshing, especially to New Yorkers getting away from the city. Nestled in a tight-knit arts and crafts hamlet, one is steps away from 18th-century buildings housing artisan studios, galleries, and boutique eateries. And there is rich Outdoor Adventure to take advantage of too! The area has direct access to the 18-mile Heritage Trail for biking and walking, plus proximity to Goosepond Mountain State Park and the Birnberg Nature Preserve. Its rural serenity offers a quiet, creative lifestyle surrounded by majestic mountains and rolling meadows, all while being part of a bustling weekend destination. Driving to and from the Conklin House to NYC is about 1 hour and 15 minutes and using mass transit a little longer. This is more than a house; it is a storied landmark reimagined for the modern connoisseur. Nothing compares to the character, lifestyle and wilderness that the Conklin House has to offer.

2 Pine Hill Road, Chester

$759,900

This beautiful custom home is planned to be built in the highly sought-after Sugar Loaf area, offering the convenience of municipal water and sewer. The main level welcomes you with warm hardwood floors and a kitchen featuring a choice of elegant granite or quartz countertops, a stainless steel appliance package, a center island perfect for meal preparation, and a spacious dining area with a slider that opens to a spacious deck. The cozy family room, complete with a fireplace, creates an ideal spot for gatherings. Also on this level are three comfortable bedrooms, including a primary suite with a bathroom showcasing a double vanity, a relaxing soaking tub, and a tiled shower, along with a stylish main hall bath. The finished lower level offers additional space with an extra bedroom or home office, along with a large recreation or living room—perfect for relaxing or entertaining. Enjoy extra features and the chance to choose custom finishes that make your home uniquely yours. Located conveniently near shopping, charming boutique stores, restaurants, wineries, breweries, apple orchards, lakes, Appalachian trails, and major commuter routes, with just about an hour to reach NYC.

4 Beds ⋅ 3 Baths ⋅ 981270 MLS

This beautiful custom home is planned to be built in the highly sought-after Sugar Loaf area, offering the convenience of municipal water and sewer. The main level welcomes you with warm hardwood floors and a kitchen featuring a choice of elegant granite or quartz countertops, a stainless steel appliance package, a center island perfect for meal preparation, and a spacious dining area with a slider that opens to a spacious deck. The cozy family room, complete with a fireplace, creates an ideal spot for gatherings. Also on this level are three comfortable bedrooms, including a primary suite with a bathroom showcasing a double vanity, a relaxing soaking tub, and a tiled shower, along with a stylish main hall bath. The finished lower level offers additional space with an extra bedroom or home office, along with a large recreation or living room—perfect for relaxing or entertaining. Enjoy extra features and the chance to choose custom finishes that make your home uniquely yours. Located conveniently near shopping, charming boutique stores, restaurants, wineries, breweries, apple orchards, lakes, Appalachian trails, and major commuter routes, with just about an hour to reach NYC.

90 Pewter Circle, Chester

$995,000

Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent Island Why wait to build? This less-than-one-year-old Tuscaloosa model on sought-after Kingfisher Lane delivers the upgrades, location, and efficiency buyers are chasing—without the timeline or added expense. Positioned just across from the Chester River, enjoy peekaboo water views from the covered front porch and even a sightline to the clubhouse. Inside, the home is bright, open, and thoughtfully designed with 5 bedrooms and 4.5 baths, offering flexibility for guests, work-from-home space, or multigenerational living. It shows like new—but lives better—because everything has already been elevated beyond builder grade. Over $70,000 in post-builder upgrades, including: • Owned solar system (10kW+) providing substantial energy savings • Custom closet systems throughout the home • Custom window treatments already installed • Premium Café Series appliances • Tankless water heater • Upgraded lighting and fixtures • Additional high-end finishes and improvements throughout The spacious floor plan offers room for everyone, while the oversized garage provides ample storage for vehicles, golf carts, and all the gear that comes with Eastern Shore living. Life in Four Seasons at Kent Island is about more than the home itself. Residents enjoy resort-style amenities including a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball courts, walking trails, kayak launch, fishing pier, and an active social calendar designed for a vibrant lifestyle. With immediate availability, extensive upgrades already completed, and one of the community's most desirable locations, this home represents an opportunity that's becoming increasingly difficult to find. Add in the recent $50,000 price reduction, and this is one of the best values currently available in Four Seasons at Kent Island. Don't miss your chance to enjoy nearly new construction, energy-efficient living, and the Chesapeake Bay lifestyle you've been waiting for.

5 Beds ⋅ 5 Baths ⋅ MDQA2016702 MLS

Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent Island Why wait to build? This less-than-one-year-old Tuscaloosa model on sought-after Kingfisher Lane delivers the upgrades, location, and efficiency buyers are chasing—without the timeline or added expense. Positioned just across from the Chester River, enjoy peekaboo water views from the covered front porch and even a sightline to the clubhouse. Inside, the home is bright, open, and thoughtfully designed with 5 bedrooms and 4.5 baths, offering flexibility for guests, work-from-home space, or multigenerational living. It shows like new—but lives better—because everything has already been elevated beyond builder grade. Over $70,000 in post-builder upgrades, including: • Owned solar system (10kW+) providing substantial energy savings • Custom closet systems throughout the home • Custom window treatments already installed • Premium Café Series appliances • Tankless water heater • Upgraded lighting and fixtures • Additional high-end finishes and improvements throughout The spacious floor plan offers room for everyone, while the oversized garage provides ample storage for vehicles, golf carts, and all the gear that comes with Eastern Shore living. Life in Four Seasons at Kent Island is about more than the home itself. Residents enjoy resort-style amenities including a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball courts, walking trails, kayak launch, fishing pier, and an active social calendar designed for a vibrant lifestyle. With immediate availability, extensive upgrades already completed, and one of the community's most desirable locations, this home represents an opportunity that's becoming increasingly difficult to find. Add in the recent $50,000 price reduction, and this is one of the best values currently available in Four Seasons at Kent Island. Don't miss your chance to enjoy nearly new construction, energy-efficient living, and the Chesapeake Bay lifestyle you've been waiting for.

215 Kingfisher Ln, Chester

$500,000

3 bedroom 2 bath contemporary home tucked away on a quiet street. Modern renovation already started, put your finishing touches on it. Home sold as is. Open concept living, spacious kitchen, private primary suite on 2nd floor with 2 additional bedrooms on 1st floor. Peaceful setting and still close to all amenities. 1,000 sq ft 2 car detached garage.

3 Beds ⋅ 2 Baths ⋅ 976521 MLS

3 bedroom 2 bath contemporary home tucked away on a quiet street. Modern renovation already started, put your finishing touches on it. Home sold as is. Open concept living, spacious kitchen, private primary suite on 2nd floor with 2 additional bedrooms on 1st floor. Peaceful setting and still close to all amenities. 1,000 sq ft 2 car detached garage.

5 N Hudson Street, Chester

$195,000

🏡 This home qualifies for special financing opportunities, including access to in-house lender programs and available grant assistance for eligible buyers! 💰 Whether you’re a first-time buyer, a homeowner who is relocating, or looking to reduce out-of-pocket costs, you may qualify for down payment and closing cost assistance. Don’t miss the chance to make homeownership more affordable — contact today for details and qualification information! Completely remodeled and truly move-in ready! This home features brand new flooring throughout, including beautiful new floors that add warmth and modern appeal to every room. The property has been fully renovated with all new framing and insulation, new plumbing (PVC & PEX), a brand new electrical system with 200 AMP service, new doors and windows, and a 2025 roof. The home is filled with beautiful lighting that enhances the bright and inviting layout. With all major systems brand new, you will not have any issues for years to come. Architectural plans and full renovation details are available upon request. No HOA. Conveniently located near Widener University, Subaru Park, Interstate 95, and the Commodore Barry Bridge for easy commuting. Close to Eddystone Crossings, perfect for convenient shopping and everyday needs.

3 Beds ⋅ 2 Baths ⋅ PADE2110566 MLS

🏡 This home qualifies for special financing opportunities, including access to in-house lender programs and available grant assistance for eligible buyers! 💰 Whether you’re a first-time buyer, a homeowner who is relocating, or looking to reduce out-of-pocket costs, you may qualify for down payment and closing cost assistance. Don’t miss the chance to make homeownership more affordable — contact today for details and qualification information! Completely remodeled and truly move-in ready! This home features brand new flooring throughout, including beautiful new floors that add warmth and modern appeal to every room. The property has been fully renovated with all new framing and insulation, new plumbing (PVC & PEX), a brand new electrical system with 200 AMP service, new doors and windows, and a 2025 roof. The home is filled with beautiful lighting that enhances the bright and inviting layout. With all major systems brand new, you will not have any issues for years to come. Architectural plans and full renovation details are available upon request. No HOA. Conveniently located near Widener University, Subaru Park, Interstate 95, and the Commodore Barry Bridge for easy commuting. Close to Eddystone Crossings, perfect for convenient shopping and everyday needs.

1119 Thomas St, Chester

$879,900

Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with open-concept living spaces ideal for modern living. Lot 3 will showcase an approximately 3200 sq. ft. colonial offered at $879,900, and Lot 4 will feature a beautiful traditional colonial approx. 3000 sq ft., priced at $869,900. Buyers also have the opportunity to bring their own custom plans and collaborate with the builder to create a home tailored to their vision. Each residence will be crafted with quality finishes and attention to detail throughout. The heart of the home will be a beautifully designed custom kitchen featuring a selection of cabinetry styles, granite or quartz countertops, farmhouse sinks, and a generous $27,000 allowance toward kitchen and bathroom cabinetry and surfaces. These thoughtfully curated options allow buyers to personalize their space while maintaining a high standard of design. Hardwood floors will be installed throughout the home, creating warmth and continuity from room to room, while the bathrooms will feature beautifully selected tile finishes for both style and durability. The spacious family room will serve as a welcoming gathering space, complete with a stunning 36-inch fireplace. The open layout flows seamlessly into a large dining area perfect for hosting holidays and special occasions, along with a comfortable living room designed for everyday relaxation and entertaining. Upstairs, each home will offer four generously sized bedrooms. The primary suite is designed as a private retreat, complete with a spa-inspired bathroom featuring a soaking tub, double vanity, and separate shower—creating a serene space to unwind at the end of the day. Golden Meadows offers exceptional convenience, located just minutes from major highways, shopping centers, apple orchards, wineries, and a wide selection of restaurants. Residents will also enjoy close proximity to the charming boutiques and the Sugar Loaf Performing Arts Center, the scenic Heritage Trail for biking and walking, and the vibrant community atmosphere that makes this area so desirable. This is a rare opportunity to build a new custom home in a prime location while enjoying modern amenities, refined finishes, and the ability to personalize your dream home from the ground up.

4 Beds ⋅ 3 Baths ⋅ 965992 MLS

Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with open-concept living spaces ideal for modern living. Lot 3 will showcase an approximately 3200 sq. ft. colonial offered at $879,900, and Lot 4 will feature a beautiful traditional colonial approx. 3000 sq ft., priced at $869,900. Buyers also have the opportunity to bring their own custom plans and collaborate with the builder to create a home tailored to their vision. Each residence will be crafted with quality finishes and attention to detail throughout. The heart of the home will be a beautifully designed custom kitchen featuring a selection of cabinetry styles, granite or quartz countertops, farmhouse sinks, and a generous $27,000 allowance toward kitchen and bathroom cabinetry and surfaces. These thoughtfully curated options allow buyers to personalize their space while maintaining a high standard of design. Hardwood floors will be installed throughout the home, creating warmth and continuity from room to room, while the bathrooms will feature beautifully selected tile finishes for both style and durability. The spacious family room will serve as a welcoming gathering space, complete with a stunning 36-inch fireplace. The open layout flows seamlessly into a large dining area perfect for hosting holidays and special occasions, along with a comfortable living room designed for everyday relaxation and entertaining. Upstairs, each home will offer four generously sized bedrooms. The primary suite is designed as a private retreat, complete with a spa-inspired bathroom featuring a soaking tub, double vanity, and separate shower—creating a serene space to unwind at the end of the day. Golden Meadows offers exceptional convenience, located just minutes from major highways, shopping centers, apple orchards, wineries, and a wide selection of restaurants. Residents will also enjoy close proximity to the charming boutiques and the Sugar Loaf Performing Arts Center, the scenic Heritage Trail for biking and walking, and the vibrant community atmosphere that makes this area so desirable. This is a rare opportunity to build a new custom home in a prime location while enjoying modern amenities, refined finishes, and the ability to personalize your dream home from the ground up.

1414 Kings Highway, Chester

$162,000

An opportunity for investors seeking their next potential income-producing property in Chester. This property offers the chance to renovate and position it for future rental use, allowing the next owner to shape it to meet their investment goals. Surrounded by an area with established rental presence and continued neighborhood improvements, the setting supports those looking to expand a portfolio and explore long-term income possibilities. Property is being sold strictly as-is.

3 Beds ⋅ 1 Baths ⋅ PADE2108326 MLS

An opportunity for investors seeking their next potential income-producing property in Chester. This property offers the chance to renovate and position it for future rental use, allowing the next owner to shape it to meet their investment goals. Surrounded by an area with established rental presence and continued neighborhood improvements, the setting supports those looking to expand a portfolio and explore long-term income possibilities. Property is being sold strictly as-is.

530 Penn St, Chester

$379,900

Great new price! Come take a look at this 2 bedroom charmer with additional room offers potential 3+ bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay window create a bright, welcoming atmosphere. Wall sconces add a soft glow, and a wall A/C unit ensures comfort throughout the warmer months. The eat in kitchen blends practicality with charm, offering tile floors, a newer refrigerator, a handy island, abundant cabinetry, and a pantry for extra storage. Another bay window brings in natural light and enhances the home’s cozy appeal. A full bathroom with a classic pedestal sink and tub completes the main living space. The primary bedroom features hardwood floors, newer windows, two closets, and its own wall A/C unit. A second bedroom—equally charming—also offers hardwood floors and plenty of natural light. Throughout the home, you’ll find generous storage options, including ample closets and a pull down attic. The property is thoughtfully equipped with a natural gas generator, a paved driveway, and multiple outbuildings that expand its functionality. The main house includes an attached two car garage, while a separate two car detached garage showcases original carriage house doors that add a touch of historic character. A small shed provides additional storage, and an oversized outbuilding—with an 8' garage door, separate electric and gas meter, and gas boiler heat—offers exceptional versatility. Above it sits a caretaker’s apartment, ideal for guests, extended family, or workspace needs. All structures are being sold as is. This property blends charm, practicality, and potential in a way that’s increasingly rare—inviting you to imagine the many ways it can fit your lifestyle.

2 Beds ⋅ 1 Baths ⋅ 964090 MLS

Great new price! Come take a look at this 2 bedroom charmer with additional room offers potential 3+ bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay window create a bright, welcoming atmosphere. Wall sconces add a soft glow, and a wall A/C unit ensures comfort throughout the warmer months. The eat in kitchen blends practicality with charm, offering tile floors, a newer refrigerator, a handy island, abundant cabinetry, and a pantry for extra storage. Another bay window brings in natural light and enhances the home’s cozy appeal. A full bathroom with a classic pedestal sink and tub completes the main living space. The primary bedroom features hardwood floors, newer windows, two closets, and its own wall A/C unit. A second bedroom—equally charming—also offers hardwood floors and plenty of natural light. Throughout the home, you’ll find generous storage options, including ample closets and a pull down attic. The property is thoughtfully equipped with a natural gas generator, a paved driveway, and multiple outbuildings that expand its functionality. The main house includes an attached two car garage, while a separate two car detached garage showcases original carriage house doors that add a touch of historic character. A small shed provides additional storage, and an oversized outbuilding—with an 8' garage door, separate electric and gas meter, and gas boiler heat—offers exceptional versatility. Above it sits a caretaker’s apartment, ideal for guests, extended family, or workspace needs. All structures are being sold as is. This property blends charm, practicality, and potential in a way that’s increasingly rare—inviting you to imagine the many ways it can fit your lifestyle.

7 Hambletonian Avenue, Chester

$699,995

A Landmark Farmhouse with a Story to Tell. Standing proudly since 1872, this historic Colonial farmhouse is one of the very first homes built on Black Meadow Road and remains a meaningful piece of Chester’s agricultural past. Once surrounded by hundreds of acres of open farmland and dairy cows, the home still carries the soul of a working farm while offering the comforts of modern living. With over 4,000 square feet of living space, the home blends authenticity with thoughtful updates. Original architectural elements—including wide-plank floors, carefully refinished—add warmth and character throughout. Two staircases provide access to the second floor, reflecting the home’s natural evolution over time. The kitchen is rich in historic detail, highlighted by authentic hand-hewn wood support beams, original to the house and a true testament to 19th-century craftsmanship. Modern enhancements integrate seamlessly, including granite countertops, custom cabinetry, stainless steel appliances, and new high-performance HPL flooring designed for durability. The layout includes six bedrooms and four bathrooms, with twin primary suites located on opposite wings of the home, each offering walk-in closets and a sense of privacy. The welcoming foyer features new hardwood floors, while the spacious mudroom has been updated with new tile flooring and a full bathroom, ideal for everyday country living. A sunken family room with a fireplace creates a cozy gathering space, and the large formal dining room, featuring newly refinished hardwood floors, is perfectly suited for holidays and special occasions. At the rear of the home, a sun-filled sunroom offers a peaceful retreat—ideal for indoor plants, a reading nook, or a creative space that enjoys natural light throughout the day and connects the home to its surrounding landscape. The basement reflects the home’s practical history. While rustic, it once served as a working space where wine was produced beginning in the 1950s, complete with original shelving used for canning and seasonal storage. Outside, raised garden boxes invite you to plant vegetables, herbs, or flowers—continuing the tradition of working the land and enjoying the rewards of homegrown living. Additional features include a two-car garage with upper-level storage and a location that offers the peace of country life with convenience—just one hour from NYC. This is more than a residence—it is a historic home, lovingly maintained, ready to welcome its next chapter.

6 Beds ⋅ 4 Baths ⋅ 960665 MLS

A Landmark Farmhouse with a Story to Tell. Standing proudly since 1872, this historic Colonial farmhouse is one of the very first homes built on Black Meadow Road and remains a meaningful piece of Chester’s agricultural past. Once surrounded by hundreds of acres of open farmland and dairy cows, the home still carries the soul of a working farm while offering the comforts of modern living. With over 4,000 square feet of living space, the home blends authenticity with thoughtful updates. Original architectural elements—including wide-plank floors, carefully refinished—add warmth and character throughout. Two staircases provide access to the second floor, reflecting the home’s natural evolution over time. The kitchen is rich in historic detail, highlighted by authentic hand-hewn wood support beams, original to the house and a true testament to 19th-century craftsmanship. Modern enhancements integrate seamlessly, including granite countertops, custom cabinetry, stainless steel appliances, and new high-performance HPL flooring designed for durability. The layout includes six bedrooms and four bathrooms, with twin primary suites located on opposite wings of the home, each offering walk-in closets and a sense of privacy. The welcoming foyer features new hardwood floors, while the spacious mudroom has been updated with new tile flooring and a full bathroom, ideal for everyday country living. A sunken family room with a fireplace creates a cozy gathering space, and the large formal dining room, featuring newly refinished hardwood floors, is perfectly suited for holidays and special occasions. At the rear of the home, a sun-filled sunroom offers a peaceful retreat—ideal for indoor plants, a reading nook, or a creative space that enjoys natural light throughout the day and connects the home to its surrounding landscape. The basement reflects the home’s practical history. While rustic, it once served as a working space where wine was produced beginning in the 1950s, complete with original shelving used for canning and seasonal storage. Outside, raised garden boxes invite you to plant vegetables, herbs, or flowers—continuing the tradition of working the land and enjoying the rewards of homegrown living. Additional features include a two-car garage with upper-level storage and a location that offers the peace of country life with convenience—just one hour from NYC. This is more than a residence—it is a historic home, lovingly maintained, ready to welcome its next chapter.

487 Black Meadow Road, Chester

$949,000

Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second kitchen and additional living space, ideal for an extended family or guests. Enjoy outdoor living with an inground pool and a large, private yard. Complete with a 3-car garage and located in the Monroe-Woodbury School District, this home offers space, comfort, and versatility.

5 Beds ⋅ 4 Baths ⋅ 950640 MLS

Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second kitchen and additional living space, ideal for an extended family or guests. Enjoy outdoor living with an inground pool and a large, private yard. Complete with a 3-car garage and located in the Monroe-Woodbury School District, this home offers space, comfort, and versatility.

12 Damian Court, Chester

$120,000

Investment opportunity in Chester. 1337 Townsend Street offers rental potential. This property features 2 bedrooms on the main floor. There is also an extra storage room accessed through the living room. Conveniently located near Widener University and public transit.

2 Beds ⋅ 1 Baths ⋅ PADE2102976 MLS

Investment opportunity in Chester. 1337 Townsend Street offers rental potential. This property features 2 bedrooms on the main floor. There is also an extra storage room accessed through the living room. Conveniently located near Widener University and public transit.

1337 Townsend St, Chester

$1,294,800

*****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! New Home, New Pier, New Pool!!!!!The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland lifestyle in this home built for entertaining and an enhanced lifestyle! There is room for everyone in this home, starting with a main level 2-car garage, rec room area, full bath & exercise/office -- this is your fun zone or whatever zone! The second level is light-filled and open with island kitchen featuring upgraded finishes, dining area, powder bath and great room with deck. You can ADD another deck on the rear of the home off the dining area if you're looking for more outdoor space. The third level features a laundry, three bedrooms including the spacious primary bedroom with updated bath and another stunning deck. The Blue Heron is a beautiful home and will serve a multitude of lifestyles. Explore your options today!

4 Beds ⋅ 4 Baths ⋅ MDQA2014542 MLS

*****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! New Home, New Pier, New Pool!!!!!The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland lifestyle in this home built for entertaining and an enhanced lifestyle! There is room for everyone in this home, starting with a main level 2-car garage, rec room area, full bath & exercise/office -- this is your fun zone or whatever zone! The second level is light-filled and open with island kitchen featuring upgraded finishes, dining area, powder bath and great room with deck. You can ADD another deck on the rear of the home off the dining area if you're looking for more outdoor space. The third level features a laundry, three bedrooms including the spacious primary bedroom with updated bath and another stunning deck. The Blue Heron is a beautiful home and will serve a multitude of lifestyles. Explore your options today!

1757 Harbor Dr, Chester

$19,500

This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details. Please note that access to 1405 Little Creek Rd is via 104 Little Creek Ct, followed by a left turn. Do not use or enter any neighboring driveways or properties as they are privately owned and clearly marked with “No Trespassing” signs. For safety reasons, please respect these boundaries.

2 Beds ⋅ 1 Baths ⋅ MDQA2014252 MLS

This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details. Please note that access to 1405 Little Creek Rd is via 104 Little Creek Ct, followed by a left turn. Do not use or enter any neighboring driveways or properties as they are privately owned and clearly marked with “No Trespassing” signs. For safety reasons, please respect these boundaries.

1405 Little Creek Rd, Chester

$439,900

PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is accented with stylish shiplap walls. There's Nothing Like NEW! Step onto the new flooring that leads you to three roomy bedrooms and two beautifully renovated full baths. Every detail has been attended to, with all-new windows, siding, plumbing, fixtures, electrical panel, light switches, septic work, water heater, doors, drywall, and a new HVAC system. With a recent roof and a dehumidified crawl space featuring a vapor barrier, this home is move-in ready—no worries, just settle in! The community enhances your lifestyle with access to four beaches, three boat ramps, a playground, ball fields, a basketball court, a picnic pavilion, a fishing pier, and plenty of opportunities for gatherings. This is the perfect place to create lasting memories!

3 Beds ⋅ 2 Baths ⋅ MDQA2011168 MLS

PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is accented with stylish shiplap walls. There's Nothing Like NEW! Step onto the new flooring that leads you to three roomy bedrooms and two beautifully renovated full baths. Every detail has been attended to, with all-new windows, siding, plumbing, fixtures, electrical panel, light switches, septic work, water heater, doors, drywall, and a new HVAC system. With a recent roof and a dehumidified crawl space featuring a vapor barrier, this home is move-in ready—no worries, just settle in! The community enhances your lifestyle with access to four beaches, three boat ramps, a playground, ball fields, a basketball court, a picnic pavilion, a fishing pier, and plenty of opportunities for gatherings. This is the perfect place to create lasting memories!

1340 Queen Anne Dr, Chester