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Gorgeous Waterfront property on Cox Creek with stunning sunset views. Open house Friday June 19, 7:00-8:30 PM for sunset viewing This cottage-style retreat on Cox Creek offers the perfect blend of cozy charm and luxury living. Featuring a refreshing pool (grandfathered in the 100 foot buffer) with 180 degree views, fully equipped gym, 4 garage spaces, dock with 2 boat lifts and jet-ski lift, a versatile guesthouse with full kitchen that sleeps 8, and an outdoor kitchen with Italian pizza oven and Evo grill! The property provides panoramic breathtaking sunset views over the water which makes it the perfect Home for those looking for the ultimate Eastern shore lifestyle! The charming main house, renovated in 2022, with its huge wrap around porch and cozy screened in porch, boasts 3 bedrooms and 3 full baths, expansive windows, high end finishes, custom moldings, and unobstructed water views. The guesthouse, built in 2021 with Full kitchen, living room, and 2 bedrooms and bath, blends character and luxury offering an inviting space with beautiful water views. It comfortably sleeps 8 with king bedroom, and bunk-bedroom with built in bunks. Reclaimed wood floors provide character, blending with the crisp white board-and-batten walls, wood ceilings, and elegant wainscoting molding. Included is a fitness gym featuring top-tier equipment built for rigorous training, and the water views inspire every workout. Guest house was used as a short term rental, generating extra income. The oversized in-ground pool has been extensively renovated to create a true resort-style outdoor experience. Major improvements completed in 2021 included new pool equipment, new plumbing and electric, new tile, a premium pool deck, and sun shelf. Newly resurfaced in 2026 provides years of beauty and enjoyment. Designed for both relaxation and recreation, the pool features an in-water sun shelf with integrated mounts for umbrellas, tables, and seating. Perfectly positioned to capture panoramic Cox Creek views and spectacular sunsets, this exceptional pool setting serves as the focal point of the property’s outdoor living and entertaining spaces, delivering a waterfront resort experience. The guest house is enhanced by a three-car garage configuration consisting of an attached two-car garage and single-car garage, providing exceptional space for vehicles, recreational equipment, and storage. Built-in shelving and storage racks accommodate kayaks, bicycles, and other outdoor gear, making the space ideally suited for an active waterfront lifestyle. In addition, the property includes a separate detached single-car garage offering outstanding flexibility for vehicle storage, a workshop, hobby area, or storage of landscaping and maintenance equipment. The detached garage is equipped with dual 30-amp, 240-volt camper receptacles with weather-protected in-use covers, providing convenient power access for recreational vehicles, trailers, or specialty equipment. Together, these garage facilities provide four enclosed garage bays and abundant storage capacity for vehicles, boats, water toys, outdoor equipment, and workshop needs. The Outdoor kitchen is positioned to capture unobstructed panoramic sunset views of the water, featuring a gas fired Alfa Pizza Oven and a flat top circular EVO cooktop. Its teppanyaki style flattop allows you to sear scallops, stir fry vegetables, or smash burgers facing the water. The private dock with a large over-water entertainment platform, electric, water, decorative lighting, two Magnum boat lifts with remote control, personal watercraft lift, and spectacular western-facing sunset views over Cox Creek. This *must see* home is more than just a house, it's a lifestyle. This property is custom built for family gatherings, entertaining, and endless outdoor recreation: Swimming, Boating, Jet-skiing, Kayaking, Paddle boarding, Yard games, Crabbing and Fishing off the dock, Biking and Pickle ball!

5 Beds ⋅ 4 Baths

Gorgeous Waterfront property on Cox Creek with stunning sunset views. Open house Friday June 19, 7:00-8:30 PM for sunset viewing This cottage-style retreat on Cox Creek offers the perfect blend of cozy charm and luxury living. Featuring a refreshing pool (grandfathered in the 100 foot buffer) with 180 degree views, fully equipped gym, 4 garage spaces, dock with 2 boat lifts and jet-ski lift, a versatile guesthouse with full kitchen that sleeps 8, and an outdoor kitchen with Italian pizza oven and Evo grill! The property provides panoramic breathtaking sunset views over the water which makes it the perfect Home for those looking for the ultimate Eastern shore lifestyle! The charming main house, renovated in 2022, with its huge wrap around porch and cozy screened in porch, boasts 3 bedrooms and 3 full baths, expansive windows, high end finishes, custom moldings, and unobstructed water views. The guesthouse, built in 2021 with Full kitchen, living room, and 2 bedrooms and bath, blends character and luxury offering an inviting space with beautiful water views. It comfortably sleeps 8 with king bedroom, and bunk-bedroom with built in bunks. Reclaimed wood floors provide character, blending with the crisp white board-and-batten walls, wood ceilings, and elegant wainscoting molding. Included is a fitness gym featuring top-tier equipment built for rigorous training, and the water views inspire every workout. Guest house was used as a short term rental, generating extra income. The oversized in-ground pool has been extensively renovated to create a true resort-style outdoor experience. Major improvements completed in 2021 included new pool equipment, new plumbing and electric, new tile, a premium pool deck, and sun shelf. Newly resurfaced in 2026 provides years of beauty and enjoyment. Designed for both relaxation and recreation, the pool features an in-water sun shelf with integrated mounts for umbrellas, tables, and seating. Perfectly positioned to capture panoramic Cox Creek views and spectacular sunsets, this exceptional pool setting serves as the focal point of the property’s outdoor living and entertaining spaces, delivering a waterfront resort experience. The guest house is enhanced by a three-car garage configuration consisting of an attached two-car garage and single-car garage, providing exceptional space for vehicles, recreational equipment, and storage. Built-in shelving and storage racks accommodate kayaks, bicycles, and other outdoor gear, making the space ideally suited for an active waterfront lifestyle. In addition, the property includes a separate detached single-car garage offering outstanding flexibility for vehicle storage, a workshop, hobby area, or storage of landscaping and maintenance equipment. The detached garage is equipped with dual 30-amp, 240-volt camper receptacles with weather-protected in-use covers, providing convenient power access for recreational vehicles, trailers, or specialty equipment. Together, these garage facilities provide four enclosed garage bays and abundant storage capacity for vehicles, boats, water toys, outdoor equipment, and workshop needs. The Outdoor kitchen is positioned to capture unobstructed panoramic sunset views of the water, featuring a gas fired Alfa Pizza Oven and a flat top circular EVO cooktop. Its teppanyaki style flattop allows you to sear scallops, stir fry vegetables, or smash burgers facing the water. The private dock with a large over-water entertainment platform, electric, water, decorative lighting, two Magnum boat lifts with remote control, personal watercraft lift, and spectacular western-facing sunset views over Cox Creek. This *must see* home is more than just a house, it's a lifestyle. This property is custom built for family gatherings, entertaining, and endless outdoor recreation: Swimming, Boating, Jet-skiing, Kayaking, Paddle boarding, Yard games, Crabbing and Fishing off the dock, Biking and Pickle ball!

328 Bentons Pleasure Rd, Chester

Listing courtesy of HomeZu by Simple Choice. Contact:

Selling Office: Coldwell Banker Realty.

$895,000

Sunday's Open House is Canceled Due to Weather! Please schedule a private showing. Welcome to 115 Cedar Rd in Chester, a spacious and truly turnkey Kent Island retreat offering over 4,000 square feet of living space, 5+ bedrooms, 4 full baths, a private in-ground pool, and room for everyone — and everything. This home delivers flexibility and function at every turn. The main level features new luxury vinyl plank flooring, with ceramic tile in the kitchen, full bath, and sunroom. The sunroom is a showstopper with vaulted ceilings, skylights, and a slider that opens directly to the pool deck — perfect for entertaining or everyday enjoyment. Your new pool equipped with a diving board will be the destination spot for summer gatherings. The kitchen is generously sized, offering abundant cabinetry and counter space, newer Frigidaire stainless steel appliances, and a butler’s bar with sink and wine fridge conveniently located between the kitchen and dining area. Upstairs, you’ll find well-sized bedrooms each with walk in closets plus a bonus space ideal for a game room, movie room, home gym, office, or additional bedroom — your lifestyle, your choice. You can put a check next to 2nd floor laundry, because this home has it! Car lovers, hobbyists, or anyone needing storage will appreciate the attached 3-car garage PLUS a detached oversized 2-car garage with electric and a walk-up attic ready for future finishing or continued storage. Set on nearly an acre, the outdoor space offers privacy, room to roam, and a backyard designed for summer fun around the pool — all with no HOA restrictions. Conveniently located near shopping, dining, marinas, and easy access to Route 50 for commuting — this home checks the boxes for space, condition, and lifestyle. Kent Island Elementary & Matapeake Middle School Districts Homes with this level of space, versatility, and amenities rarely come available — schedule your private showing today.

5 Beds ⋅ 4 Baths

Sunday's Open House is Canceled Due to Weather! Please schedule a private showing. Welcome to 115 Cedar Rd in Chester, a spacious and truly turnkey Kent Island retreat offering over 4,000 square feet of living space, 5+ bedrooms, 4 full baths, a private in-ground pool, and room for everyone — and everything. This home delivers flexibility and function at every turn. The main level features new luxury vinyl plank flooring, with ceramic tile in the kitchen, full bath, and sunroom. The sunroom is a showstopper with vaulted ceilings, skylights, and a slider that opens directly to the pool deck — perfect for entertaining or everyday enjoyment. Your new pool equipped with a diving board will be the destination spot for summer gatherings. The kitchen is generously sized, offering abundant cabinetry and counter space, newer Frigidaire stainless steel appliances, and a butler’s bar with sink and wine fridge conveniently located between the kitchen and dining area. Upstairs, you’ll find well-sized bedrooms each with walk in closets plus a bonus space ideal for a game room, movie room, home gym, office, or additional bedroom — your lifestyle, your choice. You can put a check next to 2nd floor laundry, because this home has it! Car lovers, hobbyists, or anyone needing storage will appreciate the attached 3-car garage PLUS a detached oversized 2-car garage with electric and a walk-up attic ready for future finishing or continued storage. Set on nearly an acre, the outdoor space offers privacy, room to roam, and a backyard designed for summer fun around the pool — all with no HOA restrictions. Conveniently located near shopping, dining, marinas, and easy access to Route 50 for commuting — this home checks the boxes for space, condition, and lifestyle. Kent Island Elementary & Matapeake Middle School Districts Homes with this level of space, versatility, and amenities rarely come available — schedule your private showing today.

115 Cedar Rd, Chester

Listing courtesy of Samson Properties. Contact:

Selling Office: TTR Sotheby's International Realty.

$795,000

PERFECT MULTI GENERATIONAL HOME!!!! 5 BEDROOMS! LIST PRICE ADJUSTED !!FANTASTIC HOME! THE COMPLETE PACKAGE AND THEN MORE! INGROUND GUNITE SALT WATER(LOW MAINTENANCE) POOL! TWO PRIMARY BEDROOM/BATH SUITES! BOTH WITH GIANT WALK IN CLOSETS! EACH PRIMARY BATH HAS A STEP IN SHOWER, DOUBLE STONE VANITY PLUS SOAKING TUB! THIS HOME HAS A TOTAL OF 5 BEDROOMS PLUS 3 AND ONE HALF BATHS! PLENTY OF SPACE FOR THE HOME OFFICE! THE OPEN KITCHEN IS FULLY UPDATED WITH ISLAND, STAINLESS STEEL DOUBLE OVENS, COOKTOP, DRAWER MICROWAVE, DISHWASHER,3 DOOR REFRIGERATOR, STATEMENT GRANITE, CUSTOM LIGHTING WITH DIMMERS. HEAT MONITORING DIRECTIONAL FAUCET. THE ADJACENT FAMILY ROOM FEATURES A GRANITE TRIMMED GAS FIREPLACE, TOWERING 19 FOOT CEILINGS, A UNIQUE WINDMILL STYLE CEILING FAN, AND DOUBLE TIERED WINDOWS FOR EXTRA LIGHT! THE HUGE 17X18 COVERED SCREENED PORCH IS RIGHT OFF THE KITCHEN AND FAMILY ROOM CREATING SUPER FLOW! A FEW STEPS DOWN FROM THE SCREENED PORCH THE NEW BUYER WILL FIND AN ATTRACTIVE CUSTOM PAVER PATIO AND THE INVITING IN GROUND POOL! THE REAR YARD IS SURROUNDED BY A LOW MAINTENANCE VINYL PRIVACY FENCE! OTHER FEATURES INCLUDE THE 2 CAR GARAGE WITH TONS OF SHELVING, AND A RINSE OFF SINK. THE REAR GARDEN SHED IS THE BEST EVER! ON THE INTERIOR CUSTOM WINDOW TREATMENTS, 2 INCH WHITE SHADES, LACE AND SHEER CURTAINS, WINE BAR, HUGE WALK IN CLOSETS(3), CUSTOM LIGHTING, CEILING FANS, CUSTOM CERAMIC TILE, RECENT LVP FLOORING & CARPET, MULTIPLE CONVENIENCE ITEMS, AND INCAPSULATED CRAWL SPACE HELP COMPLETE THE PACKAGE! OVER $150,000 OF RECENT IMPROVEMENTS & UPGRADES- LIST AVAILABLE. POOL EQUIPMENT INCLUDED! ONE YEAR HOME WARANTY AVAILABLE WITH ACCEPTABLE OFFER. A MUST SEE HOME !!! IMPROVEMENT LIST AND VALUES IN BRIGHT DOCS!

5 Beds ⋅ 4 Baths

PERFECT MULTI GENERATIONAL HOME!!!! 5 BEDROOMS! LIST PRICE ADJUSTED !!FANTASTIC HOME! THE COMPLETE PACKAGE AND THEN MORE! INGROUND GUNITE SALT WATER(LOW MAINTENANCE) POOL! TWO PRIMARY BEDROOM/BATH SUITES! BOTH WITH GIANT WALK IN CLOSETS! EACH PRIMARY BATH HAS A STEP IN SHOWER, DOUBLE STONE VANITY PLUS SOAKING TUB! THIS HOME HAS A TOTAL OF 5 BEDROOMS PLUS 3 AND ONE HALF BATHS! PLENTY OF SPACE FOR THE HOME OFFICE! THE OPEN KITCHEN IS FULLY UPDATED WITH ISLAND, STAINLESS STEEL DOUBLE OVENS, COOKTOP, DRAWER MICROWAVE, DISHWASHER,3 DOOR REFRIGERATOR, STATEMENT GRANITE, CUSTOM LIGHTING WITH DIMMERS. HEAT MONITORING DIRECTIONAL FAUCET. THE ADJACENT FAMILY ROOM FEATURES A GRANITE TRIMMED GAS FIREPLACE, TOWERING 19 FOOT CEILINGS, A UNIQUE WINDMILL STYLE CEILING FAN, AND DOUBLE TIERED WINDOWS FOR EXTRA LIGHT! THE HUGE 17X18 COVERED SCREENED PORCH IS RIGHT OFF THE KITCHEN AND FAMILY ROOM CREATING SUPER FLOW! A FEW STEPS DOWN FROM THE SCREENED PORCH THE NEW BUYER WILL FIND AN ATTRACTIVE CUSTOM PAVER PATIO AND THE INVITING IN GROUND POOL! THE REAR YARD IS SURROUNDED BY A LOW MAINTENANCE VINYL PRIVACY FENCE! OTHER FEATURES INCLUDE THE 2 CAR GARAGE WITH TONS OF SHELVING, AND A RINSE OFF SINK. THE REAR GARDEN SHED IS THE BEST EVER! ON THE INTERIOR CUSTOM WINDOW TREATMENTS, 2 INCH WHITE SHADES, LACE AND SHEER CURTAINS, WINE BAR, HUGE WALK IN CLOSETS(3), CUSTOM LIGHTING, CEILING FANS, CUSTOM CERAMIC TILE, RECENT LVP FLOORING & CARPET, MULTIPLE CONVENIENCE ITEMS, AND INCAPSULATED CRAWL SPACE HELP COMPLETE THE PACKAGE! OVER $150,000 OF RECENT IMPROVEMENTS & UPGRADES- LIST AVAILABLE. POOL EQUIPMENT INCLUDED! ONE YEAR HOME WARANTY AVAILABLE WITH ACCEPTABLE OFFER. A MUST SEE HOME !!! IMPROVEMENT LIST AND VALUES IN BRIGHT DOCS!

104 Woods Rd, Chester

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: The KW Collective.

$740,000

ATTENTION BUYERS: VA ASSUMABLE RATE of 2.49% AVAILABLE!! Discover the charm of this stunning Colonial home nestled in the desirable Bentons Pleasure neighborhood. With 2,791 sq. ft. of thoughtfully designed living space, this residence boasts four spacious bedrooms and 2.5 baths, perfect for both relaxation and entertaining. The well equipped kitchen invites culinary creativity, while the semi open floor plan seamlessly connects the dining and living areas, highlighted by a cozy fireplace. Enjoy the luxury of a soaking tub in the master bath and the convenience of walk-in closets. The home features beautiful wood floors and ceiling fans throughout, ensuring comfort year-round. Step outside to your private oasis, complete with a personal pool, ideal for summer gatherings or tranquil evenings. Located just minutes from commuter lots and an airport, this home offers easy access to local amenities, parks, and shopping. With a generous 1-acre lot and a side-entry garage, this property combines space, style, and convenience. Solar panels, too! Don't miss your chance to make this dream home yours!

4 Beds ⋅ 3 Baths

ATTENTION BUYERS: VA ASSUMABLE RATE of 2.49% AVAILABLE!! Discover the charm of this stunning Colonial home nestled in the desirable Bentons Pleasure neighborhood. With 2,791 sq. ft. of thoughtfully designed living space, this residence boasts four spacious bedrooms and 2.5 baths, perfect for both relaxation and entertaining. The well equipped kitchen invites culinary creativity, while the semi open floor plan seamlessly connects the dining and living areas, highlighted by a cozy fireplace. Enjoy the luxury of a soaking tub in the master bath and the convenience of walk-in closets. The home features beautiful wood floors and ceiling fans throughout, ensuring comfort year-round. Step outside to your private oasis, complete with a personal pool, ideal for summer gatherings or tranquil evenings. Located just minutes from commuter lots and an airport, this home offers easy access to local amenities, parks, and shopping. With a generous 1-acre lot and a side-entry garage, this property combines space, style, and convenience. Solar panels, too! Don't miss your chance to make this dream home yours!

123 Bentons Pleasure Rd, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact:

Selling Office: RE/MAX Executive.

$491,023

AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. Discover your private sanctuary on this sprawling 1-acre lot. This meticulously maintained residence with over 3,000 SF of total living space blends modern comfort with rare functional space. Inside, you’ll find fresh updates and an expanded, bespoke master suite designed for total relaxation. The true highlight is the property’s versatility: beyond the sun-drenched, enclosed sunroom and expansive backyard, you’ll find a massive 25x40 detached outbuilding with a 10x16 garage door—a perfect home for an RV, boat, high-end gym, or professional workshop. With the rare benefit of public sewer and an oversized 3-door garage, this property offers an exclusive lifestyle opportunity that is as practical as it is impressive. blocks to the water and marinas between Cox and Crab Alley Creek! Offers may be entered ONLINE through Friday, July 17, 2026 at 5:00 pm. AT SELLER'S DISCRETION, AN OFFER MAY BE ACCEPTED AT ANY TIME.

3 Beds ⋅ 2 Baths

AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. Discover your private sanctuary on this sprawling 1-acre lot. This meticulously maintained residence with over 3,000 SF of total living space blends modern comfort with rare functional space. Inside, you’ll find fresh updates and an expanded, bespoke master suite designed for total relaxation. The true highlight is the property’s versatility: beyond the sun-drenched, enclosed sunroom and expansive backyard, you’ll find a massive 25x40 detached outbuilding with a 10x16 garage door—a perfect home for an RV, boat, high-end gym, or professional workshop. With the rare benefit of public sewer and an oversized 3-door garage, this property offers an exclusive lifestyle opportunity that is as practical as it is impressive. blocks to the water and marinas between Cox and Crab Alley Creek! Offers may be entered ONLINE through Friday, July 17, 2026 at 5:00 pm. AT SELLER'S DISCRETION, AN OFFER MAY BE ACCEPTED AT ANY TIME.

114 Cedar Rd, Chester

Listing courtesy of Keller Williams Legacy. Contact:

Selling Office: Samson Properties.

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