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$799,000

Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in a peaceful, park-like setting. Designed for both comfort and elegance, this home features expansive, light-filled interiors and timeless architectural details throughout. The heart of the home is a large, luxurious living room showcasing vaulted, beamed ceilings, a fireplace, and sweeping views of the expansive rear yard. Rich hickory hardwood flooring runs throughout the kitchen, breakfast area, living room, office, and formal dining room, creating a warm and cohesive flow across the main living spaces. The formal dining room is enhanced with elegant crown molding, offering a refined setting ideal for both everyday living and entertaining. The updated gourmet kitchen features granite countertops, abundant cabinetry, and a seamless connection to the breakfast area and main living spaces, making it both functional and inviting. The private primary suite is generously sized and offers two walk-in closets along with a beautifully appointed en-suite bath featuring a luxury soaking tub, double vanity, travertine tile flooring, and a tiled walk-in shower. Two additional bedrooms provide ample closet space and share a well-appointed full bath, also finished with travertine tile flooring and a tiled shower. Outdoor living is equally impressive with extensive mature landscaping that enhances privacy and natural beauty. A stone patio and a combination of brick and Trex decks provide multiple spaces for relaxing or entertaining while enjoying the serene surroundings. Additional features include an attached two-car garage as well as a detached one-car garage, offering exceptional storage and flexibility. Ideally located just minutes from historic Chestertown and only a golf cart ride to the Chester River Yacht and Country Club and the Chester River, this exceptional home blends privacy, convenience, and luxury Eastern Shore living at its finest.

3 Beds ⋅ 3 Baths

Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in a peaceful, park-like setting. Designed for both comfort and elegance, this home features expansive, light-filled interiors and timeless architectural details throughout. The heart of the home is a large, luxurious living room showcasing vaulted, beamed ceilings, a fireplace, and sweeping views of the expansive rear yard. Rich hickory hardwood flooring runs throughout the kitchen, breakfast area, living room, office, and formal dining room, creating a warm and cohesive flow across the main living spaces. The formal dining room is enhanced with elegant crown molding, offering a refined setting ideal for both everyday living and entertaining. The updated gourmet kitchen features granite countertops, abundant cabinetry, and a seamless connection to the breakfast area and main living spaces, making it both functional and inviting. The private primary suite is generously sized and offers two walk-in closets along with a beautifully appointed en-suite bath featuring a luxury soaking tub, double vanity, travertine tile flooring, and a tiled walk-in shower. Two additional bedrooms provide ample closet space and share a well-appointed full bath, also finished with travertine tile flooring and a tiled shower. Outdoor living is equally impressive with extensive mature landscaping that enhances privacy and natural beauty. A stone patio and a combination of brick and Trex decks provide multiple spaces for relaxing or entertaining while enjoying the serene surroundings. Additional features include an attached two-car garage as well as a detached one-car garage, offering exceptional storage and flexibility. Ideally located just minutes from historic Chestertown and only a golf cart ride to the Chester River Yacht and Country Club and the Chester River, this exceptional home blends privacy, convenience, and luxury Eastern Shore living at its finest.

7828 Country Club Ln, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$885,000

Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an entry-level bedroom and full bathroom. The partially finished basement offers a large bedroom or bonus room, a full bathroom, and an oversized workshop space. Upstairs you'll find two bedrooms that share a full bathroom, as well as the primary bedroom, which is nicely situated with a view of the creek/pond. Enjoy peaceful views of the creek from the slate patio, and launch a kayak to explore the water from your backyard. This property leaves little to be desired! Two-car garage, peaceful water view, cozy fireplace, large living space, nicely landscaped, and a hot tub! Under 2 miles from downtown Chestertown and a short stroll to the Chester River Yacht & Country Club.

5 Beds ⋅ 4 Baths

Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an entry-level bedroom and full bathroom. The partially finished basement offers a large bedroom or bonus room, a full bathroom, and an oversized workshop space. Upstairs you'll find two bedrooms that share a full bathroom, as well as the primary bedroom, which is nicely situated with a view of the creek/pond. Enjoy peaceful views of the creek from the slate patio, and launch a kayak to explore the water from your backyard. This property leaves little to be desired! Two-car garage, peaceful water view, cozy fireplace, large living space, nicely landscaped, and a hot tub! Under 2 miles from downtown Chestertown and a short stroll to the Chester River Yacht & Country Club.

7680 Country Club Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$468,000

Charming Brick Rancher Near the Chester River This custom-built brick rancher sits in a nice Chestertown neighborhood with excellent curb appeal, a classic hipped roof, and a convenient circular driveway. The drive runs under a gable-roofed breezeway that connects to an oversized 26x40 two-car garage, which will soon have brand-new garage doors. Coming into the Home... Living Room: Walk along the cobblestone slate path and pass through the new, classic front door into a spacious living room featuring hardwood floors that run throughout the entire house. Dining & Kitchen: A curved archway leads from the living room directly into the dining room. The dining room has an entryway to the kitchen, which could easily be opened up for an even more open feel. Porch: The dining room leads right out to a comfortable porch—the perfect spot to relax and enjoy this nice, quiet neighborhood. Mudroom & Back Entry: An oversized back entry from the breezeway leads into a large mudroom and utility space. Featuring multiple closets and laundry hookups, this functional area offers plenty of space to be creative and fit your family's needs. Bedrooms: The main floor includes three bedrooms with hardwood floors and two full bathrooms Basement: The full basement features an open space with brand-new windows that allow plenty of natural light inside. It is equipped with a new sump pump, offering a perfect blank canvas for storage, a gym, or a rec room. Utilities, Key Updates & Location The house sits on a generous lot with mature landscaping and is connected to well water and public septic. Recent mechanical and structural updates include: Brand-new roof, oil furnace paired with a new HVAC system for efficient heating and cooling. Fresh paint inside and out. You can enjoy beautiful views of the Chester River coming and going from your new home, as well as scenic river views while taking your neighborhood walks. Enjoy the convenience of being just minutes from downtown shopping and dining. Bring your design ideas to update the interior and make it your own!

3 Beds ⋅ 2 Baths

Charming Brick Rancher Near the Chester River This custom-built brick rancher sits in a nice Chestertown neighborhood with excellent curb appeal, a classic hipped roof, and a convenient circular driveway. The drive runs under a gable-roofed breezeway that connects to an oversized 26x40 two-car garage, which will soon have brand-new garage doors. Coming into the Home... Living Room: Walk along the cobblestone slate path and pass through the new, classic front door into a spacious living room featuring hardwood floors that run throughout the entire house. Dining & Kitchen: A curved archway leads from the living room directly into the dining room. The dining room has an entryway to the kitchen, which could easily be opened up for an even more open feel. Porch: The dining room leads right out to a comfortable porch—the perfect spot to relax and enjoy this nice, quiet neighborhood. Mudroom & Back Entry: An oversized back entry from the breezeway leads into a large mudroom and utility space. Featuring multiple closets and laundry hookups, this functional area offers plenty of space to be creative and fit your family's needs. Bedrooms: The main floor includes three bedrooms with hardwood floors and two full bathrooms Basement: The full basement features an open space with brand-new windows that allow plenty of natural light inside. It is equipped with a new sump pump, offering a perfect blank canvas for storage, a gym, or a rec room. Utilities, Key Updates & Location The house sits on a generous lot with mature landscaping and is connected to well water and public septic. Recent mechanical and structural updates include: Brand-new roof, oil furnace paired with a new HVAC system for efficient heating and cooling. Fresh paint inside and out. You can enjoy beautiful views of the Chester River coming and going from your new home, as well as scenic river views while taking your neighborhood walks. Enjoy the convenience of being just minutes from downtown shopping and dining. Bring your design ideas to update the interior and make it your own!

25750 Collins Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$4,200,000

A ONCE-IN-A-LIFETIME ESTATE OFFERING where privacy, refinement, and resort-style living come together in extraordinary fashion. Privately set on 3+ meticulously landscaped acres, this exceptional residence was designed for the most discerning buyer—one who values scale, craftsmanship, wellness, recreation, and a true sense of retreat. Meticulously cared for and maintained, the home makes a striking impression with its double pre-cast concrete balustrade staircase, elegant front approach, and distinctive barrel tile roof. Inside, soaring ceilings, expansive windows, red oak hardwood, Grecian marble tile flooring, custom plaster walls, intricate millwork, and refined architectural details create a home that feels both grand and deeply livable. Designer appointments include Phylrich faucets, Baldwin brass hardware, Hunter Douglas shades, and carefully selected finishes throughout. The floor plan is exceptional, featuring 4 spacious ensuite bedrooms, 5 full baths /1 half bath, a coveted FIRST-FLOOR PRIMARY SUITE, and two private home offices—ideal for today’s luxury lifestyle. The custom chef’s kitchen is beautifully appointed with top-tier appliances, generous workspace, and elegant finishes, offering both performance and style. The walk-out lower level is truly remarkable and expands the home into a complete lifestyle experience. Designed for entertaining, wellness, and relaxation, it features a state-of-the-art gym/fitness room equipped for serious training, a dedicated massage room, a full second kitchen, and expansive recreation and lounge areas that open effortlessly to the outdoor living spaces. Outside, the property becomes a private resort. A stunning salt-water pool with integrated spa, an additional hot tub, two tranquil koi ponds with waterfalls and advanced filtration systems, Mugnaini Italian wood-fired commercial Pizza oven, and a full-sized, Har-tru tennis court create an unmatched setting for VACATION LIVING EVERY DAY. The grounds feel serene, private, and beautifully curated—offering the rare combination of elegance, recreation, and total escape. Ideally located near Northampton Country Club and Moravian Academy, with easy access to Routes 33, 22, and 78, and just minutes to the New Jersey border, this location offers convenience for those traveling throughout the Lehigh Valley, into New Jersey, or toward New York City. This is more than a home—it is a private estate, a wellness retreat, an entertainer’s dream, and a rare opportunity to own one of the area’s most distinctive luxury properties.

4 Beds ⋅ 6 Baths

A ONCE-IN-A-LIFETIME ESTATE OFFERING where privacy, refinement, and resort-style living come together in extraordinary fashion. Privately set on 3+ meticulously landscaped acres, this exceptional residence was designed for the most discerning buyer—one who values scale, craftsmanship, wellness, recreation, and a true sense of retreat. Meticulously cared for and maintained, the home makes a striking impression with its double pre-cast concrete balustrade staircase, elegant front approach, and distinctive barrel tile roof. Inside, soaring ceilings, expansive windows, red oak hardwood, Grecian marble tile flooring, custom plaster walls, intricate millwork, and refined architectural details create a home that feels both grand and deeply livable. Designer appointments include Phylrich faucets, Baldwin brass hardware, Hunter Douglas shades, and carefully selected finishes throughout. The floor plan is exceptional, featuring 4 spacious ensuite bedrooms, 5 full baths /1 half bath, a coveted FIRST-FLOOR PRIMARY SUITE, and two private home offices—ideal for today’s luxury lifestyle. The custom chef’s kitchen is beautifully appointed with top-tier appliances, generous workspace, and elegant finishes, offering both performance and style. The walk-out lower level is truly remarkable and expands the home into a complete lifestyle experience. Designed for entertaining, wellness, and relaxation, it features a state-of-the-art gym/fitness room equipped for serious training, a dedicated massage room, a full second kitchen, and expansive recreation and lounge areas that open effortlessly to the outdoor living spaces. Outside, the property becomes a private resort. A stunning salt-water pool with integrated spa, an additional hot tub, two tranquil koi ponds with waterfalls and advanced filtration systems, Mugnaini Italian wood-fired commercial Pizza oven, and a full-sized, Har-tru tennis court create an unmatched setting for VACATION LIVING EVERY DAY. The grounds feel serene, private, and beautifully curated—offering the rare combination of elegance, recreation, and total escape. Ideally located near Northampton Country Club and Moravian Academy, with easy access to Routes 33, 22, and 78, and just minutes to the New Jersey border, this location offers convenience for those traveling throughout the Lehigh Valley, into New Jersey, or toward New York City. This is more than a home—it is a private estate, a wellness retreat, an entertainer’s dream, and a rare opportunity to own one of the area’s most distinctive luxury properties.

4250 Raynessa Ct, Easton

Listing courtesy of BHHS Fox & Roach - Center Valley. Contact: (610) 282-4444