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$1,850,000

Step back into the timeless charm of Rehoboth Beach in the coveted, quiet Country Club Estates neighborhood, where treasured beach memories are made and downtown is just a leisurely stroll away. This charming 4-bedroom home offers the quintessential Rehoboth lifestyle—walk to the beach, wander down to the boardwalk, grab your morning coffee, browse the shops, and enjoy dinner downtown, all without getting in the car. Lovingly maintained and thoughtfully updated, this home beautifully blends the nostalgia and character of a classic Rehoboth Beach retreat with the comforts of today. The kitchen flows seamlessly into the open and inviting living room, creating a welcoming space for gathering with family and friends. The front screened porch, enhanced with EZ Breeze windows installed in 2024, is the perfect spot for morning coffee, an afternoon read, or unwinding after a day at the beach while enjoying the coastal breeze. Recent updates and features include new upstairs flooring in 2026, a tankless water heater, irrigation system, and two-zone heating and cooling for year-round comfort. Whether you're looking for a beloved family beach house, a full-time residence, a second home, or a proven income-producing property, this home delivers. It boasts an impressive rental history, averaging approximately $60,000 annually, and is being offered mostly furnished—making it easy to settle in and start enjoying the Rehoboth lifestyle from day one. There is something special about a home where you can leave the car in the driveway and walk to the places that make Rehoboth Beach so memorable. From beach days and boardwalk strolls to ice cream after dinner and evenings spent exploring downtown, this is the kind of location that evokes the best of Rehoboth's timeless appeal. Homes in Country Club Estates rarely come on the market—don't miss this opportunity to own your own piece of classic Rehoboth Beach.

4 Beds ⋅ 2 Baths

Step back into the timeless charm of Rehoboth Beach in the coveted, quiet Country Club Estates neighborhood, where treasured beach memories are made and downtown is just a leisurely stroll away. This charming 4-bedroom home offers the quintessential Rehoboth lifestyle—walk to the beach, wander down to the boardwalk, grab your morning coffee, browse the shops, and enjoy dinner downtown, all without getting in the car. Lovingly maintained and thoughtfully updated, this home beautifully blends the nostalgia and character of a classic Rehoboth Beach retreat with the comforts of today. The kitchen flows seamlessly into the open and inviting living room, creating a welcoming space for gathering with family and friends. The front screened porch, enhanced with EZ Breeze windows installed in 2024, is the perfect spot for morning coffee, an afternoon read, or unwinding after a day at the beach while enjoying the coastal breeze. Recent updates and features include new upstairs flooring in 2026, a tankless water heater, irrigation system, and two-zone heating and cooling for year-round comfort. Whether you're looking for a beloved family beach house, a full-time residence, a second home, or a proven income-producing property, this home delivers. It boasts an impressive rental history, averaging approximately $60,000 annually, and is being offered mostly furnished—making it easy to settle in and start enjoying the Rehoboth lifestyle from day one. There is something special about a home where you can leave the car in the driveway and walk to the places that make Rehoboth Beach so memorable. From beach days and boardwalk strolls to ice cream after dinner and evenings spent exploring downtown, this is the kind of location that evokes the best of Rehoboth's timeless appeal. Homes in Country Club Estates rarely come on the market—don't miss this opportunity to own your own piece of classic Rehoboth Beach.

345 Hickman St, Rehoboth Beach

Listing courtesy of Jack Lingo - Rehoboth. Contact: (302) 227-3883

$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

$659,999

Live where you play at 7712 Waterview Lane in sought-after Country Club Estates. Situated on just under an acre, this beautifully renovated, well-maintained Cape Cod is a quick bike ride to downtown Chestertown or an easy walk to the Chester River Yacht and Country Club. Timeless interior features, a main-floor primary suite, and practical indoor/outdoor living spaces make this the perfect home for everyday living or a weekend retreat. The well-designed first floor - featuring hardwoods, baseboards, and crown moldings throughout - is anchored by the open-concept kitchen and living room spaces, which flow naturally to the back sunroom and exterior deck. The renovated kitchen now features solid wood cabinets, quartz countertops, stainless steel appliances, recessed lighting, and overhanging bar seating. Cozy up with a book by the living room brick fireplace with a propane insert, surrounded by classic built-in bookshelves. Passing through the back sliding doors, you will be greeted by the sunroom and oversized back deck: each perfect for crab feasts and summer bbq's. Enjoy summer evenings while overlooking the private backyard, which is fully fenced-in and has plenty of space for dogs and children. The main floor also features a primary bedroom with an ensuite bath, a large walk-in closet, and a separate office. The renovated primary bath now features ceramic tile, a standing stall shower, wainscoting, double vanity, and new recessed lights. A dining room off the kitchen with a lovely bay window flows through a pocket door into the formal living room with built-in bookcases. The main floor is finished by a renovated powder room and laundry room just off the kitchen. Upstairs, you will find two more generously sized bedrooms, a full shared bath, and a potential 4th bedroom or office space for those who work from home. An attached two-car garage includes another half bath, additional storage, and a separate workroom for those who like to tinker. Mature trees provide lots of shade and privacy around the meticulously maintained front and back yards. A generously sized storage shed is perfect for garden tools and the lawnmower. Located on a quiet, dead-end street, the neighborhood is great for dog walkers and evening strolls. Improvements made by current owner: whole kitchen remodel including cabinets, countertops, appliances, hardwood floors (2019); primary bathroom and powder room remodel including ceramic tile, standing shower stall, toilets, wainscoting, double vanity, fixtures (2017), 14 windows replaced with double-pane insulated (2017); Carrier HVAC (2017); whole-house water filter and well pressure tank (2022); crawl space improvement (2016); and professional landscaping. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market, and a laid-back lifestyle with an endless number of social or volunteer activities. Less than 90 minutes to Washington D.C. or Philadelphia. Enjoy country living on the Eastern Shore. Professional photos to come!

3 Beds ⋅ 4 Baths

Live where you play at 7712 Waterview Lane in sought-after Country Club Estates. Situated on just under an acre, this beautifully renovated, well-maintained Cape Cod is a quick bike ride to downtown Chestertown or an easy walk to the Chester River Yacht and Country Club. Timeless interior features, a main-floor primary suite, and practical indoor/outdoor living spaces make this the perfect home for everyday living or a weekend retreat. The well-designed first floor - featuring hardwoods, baseboards, and crown moldings throughout - is anchored by the open-concept kitchen and living room spaces, which flow naturally to the back sunroom and exterior deck. The renovated kitchen now features solid wood cabinets, quartz countertops, stainless steel appliances, recessed lighting, and overhanging bar seating. Cozy up with a book by the living room brick fireplace with a propane insert, surrounded by classic built-in bookshelves. Passing through the back sliding doors, you will be greeted by the sunroom and oversized back deck: each perfect for crab feasts and summer bbq's. Enjoy summer evenings while overlooking the private backyard, which is fully fenced-in and has plenty of space for dogs and children. The main floor also features a primary bedroom with an ensuite bath, a large walk-in closet, and a separate office. The renovated primary bath now features ceramic tile, a standing stall shower, wainscoting, double vanity, and new recessed lights. A dining room off the kitchen with a lovely bay window flows through a pocket door into the formal living room with built-in bookcases. The main floor is finished by a renovated powder room and laundry room just off the kitchen. Upstairs, you will find two more generously sized bedrooms, a full shared bath, and a potential 4th bedroom or office space for those who work from home. An attached two-car garage includes another half bath, additional storage, and a separate workroom for those who like to tinker. Mature trees provide lots of shade and privacy around the meticulously maintained front and back yards. A generously sized storage shed is perfect for garden tools and the lawnmower. Located on a quiet, dead-end street, the neighborhood is great for dog walkers and evening strolls. Improvements made by current owner: whole kitchen remodel including cabinets, countertops, appliances, hardwood floors (2019); primary bathroom and powder room remodel including ceramic tile, standing shower stall, toilets, wainscoting, double vanity, fixtures (2017), 14 windows replaced with double-pane insulated (2017); Carrier HVAC (2017); whole-house water filter and well pressure tank (2022); crawl space improvement (2016); and professional landscaping. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market, and a laid-back lifestyle with an endless number of social or volunteer activities. Less than 90 minutes to Washington D.C. or Philadelphia. Enjoy country living on the Eastern Shore. Professional photos to come!

7712 Waterview Ln, Chestertown

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

$448,000

Rambling rancher on an established 3/4 acre garden in Country Club Estates with No HOA fees has extensive recent renovations: New architectural shingle Roof, New Heat pump, Stainless Kitchen appliances, New Bathroom fixtures, New Porch screening, New doors, New Ring video doorbell, ceiling lights and switches, Fresh paint and 6 New windows brighten a Basement Family room with 18” porcelain tile. A 40’ x 26’ block 2-car Garage with New insulated doors & openers, built-in shelving, jalousie windows, storage loft and 50% garage extension for Workshop as potential hobby space, home-based business or sporting gear cave. The Garage faces a private parking pad behind the home and a U-shaped driveway to a drive-through carport has the rear door entering a large Foyer convenient for bring in the groceries to the custom built Kitchen with a work-triangle layout. Finishing touches to the renovations are nearly complete, just choose the bedroom Carpeting and move into your New Home! Living Room: Walk along the slate flagstone path and pass through the New, classic Front Door into a spacious Living room featuring an elegant Fireplace and Hardwood floors that extend through a wide open Archway into the Dining room which opens to a comfortable screened Porch—the perfect spot to relax and enjoy the Garden view in this Prestigious neighborhood. Bedrooms: The main floor has a secluded Bedroom Wing with Hardwood floors and full Bathroom with 2 linen closets. A second Bathroom is conveniently close to Foyer and stairwell to Basement: The full Basement features an open Family room with brand-new windows that allow plenty of natural light inside. A side room equipped with a new sump pump well is a perfect blank canvas offering for an Office, Storage or a Rec room. Mechanical & Utillity Room: Separate Electric water heater from Oil boiler to provide comfortable hot water baseboard heat which is supplemented by a new HVAC system for Efficient heating and cooling. Enjoy Resort-like living in this Brick Ranch house only a chip shot away from the Chester River Yacht and Country Club with scenic river views while taking your neighborhood walks, And 5 minute drives along the Chester River, coming and going from your New Home to Historic Chestertown shopping and dining district, also well known for Live Arts, Festivals and home to Washington College.

3 Beds ⋅ 2 Baths

Rambling rancher on an established 3/4 acre garden in Country Club Estates with No HOA fees has extensive recent renovations: New architectural shingle Roof, New Heat pump, Stainless Kitchen appliances, New Bathroom fixtures, New Porch screening, New doors, New Ring video doorbell, ceiling lights and switches, Fresh paint and 6 New windows brighten a Basement Family room with 18” porcelain tile. A 40’ x 26’ block 2-car Garage with New insulated doors & openers, built-in shelving, jalousie windows, storage loft and 50% garage extension for Workshop as potential hobby space, home-based business or sporting gear cave. The Garage faces a private parking pad behind the home and a U-shaped driveway to a drive-through carport has the rear door entering a large Foyer convenient for bring in the groceries to the custom built Kitchen with a work-triangle layout. Finishing touches to the renovations are nearly complete, just choose the bedroom Carpeting and move into your New Home! Living Room: Walk along the slate flagstone path and pass through the New, classic Front Door into a spacious Living room featuring an elegant Fireplace and Hardwood floors that extend through a wide open Archway into the Dining room which opens to a comfortable screened Porch—the perfect spot to relax and enjoy the Garden view in this Prestigious neighborhood. Bedrooms: The main floor has a secluded Bedroom Wing with Hardwood floors and full Bathroom with 2 linen closets. A second Bathroom is conveniently close to Foyer and stairwell to Basement: The full Basement features an open Family room with brand-new windows that allow plenty of natural light inside. A side room equipped with a new sump pump well is a perfect blank canvas offering for an Office, Storage or a Rec room. Mechanical & Utillity Room: Separate Electric water heater from Oil boiler to provide comfortable hot water baseboard heat which is supplemented by a new HVAC system for Efficient heating and cooling. Enjoy Resort-like living in this Brick Ranch house only a chip shot away from the Chester River Yacht and Country Club with scenic river views while taking your neighborhood walks, And 5 minute drives along the Chester River, coming and going from your New Home to Historic Chestertown shopping and dining district, also well known for Live Arts, Festivals and home to Washington College.

25750 Collins Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Coastal Homestead Group

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