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801 Keeling Drive Drive, South Chesapeake
$695,000
4 Beds ⋅ 3.1 Baths ⋅ 10656163 MLS
Your own private retreat in the heart of Cheshire Forest! This beautifully maintained 4 bedroom, 3.5 bath home offers over 3,100 sq ft with a floor plan made for everyday living and entertaining. Inside, enjoy gorgeous oak floors, an updated open concept kitchen, formal living and dining rooms, a sun-filled family room with fireplace, and a spacious primary suite with its own fireplace. Outside is where this home truly shines; take a dip in the heated in-ground pool, relax on the deck, or unwind in your private, fully fenced backyard. An impressive list of improvements includes a new pool liner (2025), upstairs A/C (2024), refinished hardwood floors, updated roof, gutters, garage door, HVAC, water heater and more. Two-car garage plus Cheshire Forest amenities including a clubhouse, community pool, playground and tennis courts. A rare combination of space, updates and resort-style living in Great Bridge!

801 Keeling Drive Drive, South Chesapeake

317 George Washington Highway S, South Chesapeake
$524,900
3 Beds ⋅ 2 Baths ⋅ 10655769 MLS
Five acres. A powered detached workshop. Room to breathe, space to make your own. This updated Cape Cod offers the flexibility of acreage living in Chesapeake’s Grassfield area. The home features 3 bedrooms, 2 full baths and a first-floor bedroom and full bath. MLS square footage reflects 1,869 sq. ft. per tax records; a recent appraisal measured approximately 2,067 sq. ft.Updates include a renovated kitchen and baths, replacement windows, updated electrical and plumbing, a 2023 heat pump, 2024 whole-house paint and newer flooring. Beautiful hardwood floors, a fireplace, and generous mud/laundry space add function and character. The approx. 736 sq. ft. powered detached garage/workshop offers room for tools, projects, and storage. Gorgeous outdoors boast a fenced yard area, wooded acreage, mature fruit and fig trees, enclosed porch, deck and patio. City water/sewer add convenience. Recent appraisal at $600,000! Existing VA loan may be assumable, reach out to listing agent for more details.

317 George Washington Highway S, South Chesapeake

1005 Winged Foot Court Unit B, South Chesapeake
$335,000
3 Beds ⋅ 2.1 Baths ⋅ 10656159 MLS
Welcome Home to this charming twin Home style Condo in Greenbrier's Fairways Villas. Tucked away in the cul-de-sac with garage, driveway, and communal parking, low maintenance living meets style and convenience. Enter into your inviting foyer greeted with LVP floors and neutral paint. Layout features large open concept great room and dining area. Eat-in kitchen is spacious with granite tops and stainless appliances. Access to one car garage and laundry off kitchen and half bath for the ultimate first floor layout. Second level features large primary bedroom with ensuite bath and walk in closet. Bedroom features natural light and vaulted ceilings. Two large spare bedrooms and hall bathroom complete this ideal layout. Large slider leads to rear deck which is large and tranquil backing up to golf course views. Newer HVAC & water heater 2021 and replacement windows. Call this Home Today!

1005 Winged Foot Court Unit B, South Chesapeake

1407 Hawick Terrace, South Chesapeake
$499,999
3 Beds ⋅ 3 Baths ⋅ 10656063 MLS
Welcome home to Chesapeake’s premier 55+ community! This move-in-ready home offers a fantastic and flexible floor plan featuring TWO spacious primary suites—one on each level—providing plenty of room for guests. The beautiful family room features soaring vaulted ceilings, luxury vinyl plank flooring, and a cozy gas fireplace. Just off the main living area is an additional first-floor flex space, perfect for a home office, reading room, or a relaxing spot to enjoy your morning coffee. The spacious eat-in kitchen features new stainless steel appliances and recessed lighting, while the formal dining room provides the perfect space for entertaining. The large first-floor primary suite offers a private bath with double vanity, separate shower, and oversized jetted tub. At the heart of the community is the Bay Club, featuring indoor and outdoor pools, hot tub, fitness center, billiards, library, game rooms, and so much more. Come experience resort-style living at Eagle Pointe!

1407 Hawick Terrace, South Chesapeake

2220 Edwin Drive, South Chesapeake
$585,740
3 Beds ⋅ 3 Baths ⋅ 10656034 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2220 Edwin Drive, South Chesapeake

241 Sign Pine Road, South Chesapeake
$950,000
4 Beds ⋅ 3.1 Baths ⋅ 10655919 MLS
Your dream home awaits!! Craftsman bones, a custom remodel, and a horse barn out back: acreage living with refined character. Every inch of this home was designed by the sellers who were contractors with love over the years. Inside, coffered ceilings meet warm cedar and wood-plank ceilings, giving every room a crafted, finished feel, and Brazilian cherry hardwoods run underfoot toward a stone gas-log fireplace that anchors the living space. Floor-to-ceiling windows and skylights flood the home with light, while custom barn doors and Restoration Hardware fixtures make even the transitions between rooms feel intentional. The kitchen is built to gather around. An oversized honed granite island with a built-in microwave takes center stage, backed by custom cabinetry, an etched tile backsplash, a built-in pantry, newer appliances, and purified water at the sink. Next door, color-changing upper lighting lets the dining room shift from weeknight dinner to late-night celebration at the flip of a switch. The first-floor and second story primary suite comes with its own bath, the bathrooms have been updated throughout, and a sun room, bar and mudroom with drop zone give the layout room to breathe. Then step outside, where the property really shows off. A 40,000-gallon saltwater pool, 8 feet deep with a diving board and fountain, sits beside a koi pond and gazebo linked by brick walkways. Made for a party or a wedding. Beyond it, a fenced acre of pasture leads to a barn with two stalls, a wash stall, a brick-paved breezeway, tack room, and horses are allowed. Wrapped in Hardie plank and stone, heated and cooled by geothermal, and tucked into a wooded setting of nearly five acres neighboring Greenbrier Farms in the Hickory school zone. Morning coffee in the sun room, afternoons at the barn, evenings by the pool: this home makes every part of the day worth staying for. And let's talk privacy.

241 Sign Pine Road, South Chesapeake

1103 Madison Lynn Way, South Chesapeake
$640,000
5 Beds ⋅ 2.1 Baths ⋅ 10655665 MLS
Welcome home to 1103 Madison Lynn Way in Chesapeake! Located in the sought-after Hanbury Manor community and Great Bridge School District, this spacious 5-bedroom, 2.5-bath home offers approximately 2,557 square feet with a bright, open layout designed for everyday living and entertaining. The main level features an inviting living area, dedicated dining space, and a first-floor bedroom ideal for guests, a home office, or flex space. The updated kitchen features quartz countertops, stainless steel appliances, ample cabinetry, and LVP flooring. Upstairs, you’ll find four additional bedrooms, including a spacious primary suite with cathedral ceilings, a walk-in closet, and ensuite bath with a soaking tub and separate walk-in shower, along with a dedicated laundry room with a utility sink. Outside, enjoy a fully fenced backyard with a patio and storage shed, plus an attached two-car garage. With no HOA and a convenient location near Great Bridge schools, shopping, dining, and interstate access, this home offers the space, updates, and location you’ve been looking for!

1103 Madison Lynn Way, South Chesapeake

200 Traditions Way, South Chesapeake
$655,000
3 Beds ⋅ 3.1 Baths ⋅ 10655918 MLS
This SHOWCASE home can be yours - MOVE IN READY! Award-winning builder blends elegance and easy living w/all grounds maintained! Exceptional details - Custom lighting throughout, Designer wallpaper, Culinary bar, White oak beams and more, and Matte White GE Cafe appliances w/Brushed Brass. French doors open to custom 12x30 paver w/fenced yard. HW throughout first floor, first floor BR with full bath, tiled shower, first-floor laundry (and full laundry up). Upstairs HW flooring in Up Hall, Loft and Primary BR. Loft with custom bar for relaxing evenings. Stunning primary BR with 10'x13' custom walk-in closet and 2 finished closets 10'x5' finished storage closets. Spa-inspired bath with 9' vanity, WOW shower, free-standing tub, champagne ready. Professionally managed community.

200 Traditions Way, South Chesapeake

1153 Edinburgh Parkway, South Chesapeake
$725,000
5 Beds ⋅ 3 Baths ⋅ 10655913 MLS
Cottage charm on the outside, showstopper on the inside, and Stephen Alexander craftsmanship in every detail! This Caramel Cottage in Great Bridge delivers the builder's signature molding and trim, soaring 10-foot ceilings, and rich hardwood floors from the moment you step into the foyer. The highly flexible floor plan features a sought-after first-floor bedroom and full bath, or a dedicated office/study and a formal dining area ready for holiday dinners and special occasions. The living room is anchored by a gas fireplace framed in custom built-ins, creating a warm and inviting gathering space that flows easily into the heart of the home. The kitchen is the true showpiece, with 42" white cabinetry that rises to meet those tall ceilings, an oversized island with plenty of room to gather, a gas range, stainless appliances, and a walk-in pantry for effortless organization. The breakfast area adds a relaxed spot for everyday meals, making cooking and entertaining easy. Upstairs, the primary suite is a private retreat with a tiled shower, jetted soaking tub, dual vanities, and a spacious walk-in closet. A finished room over the garage offers even more flexibility as a media room, hobby space, or bonus room, and brand-new carpet is already in place! And then there's the porch! The three-season Eze-Breeze enclosure is one of the home's best features, with sliding vinyl panels that open wide to let the breeze in and close up to keep rain, wind, and bugs out, so porch season doesn't end when summer does. From there, step down to the large paver patio in a privacy-fenced backyard, a relaxing setting for morning coffee, evening gatherings, or simply unwinding outdoors. Thoughtful details continue throughout, including zoned heating and cooling, fiber cement siding, a walk-in attic for extra storage, a utility room, and an attached two-car garage with additional driveway parking. From the curb to the craftsmanship, every inch of this home was built with intention. This is Great Living in Great Bridge!

1153 Edinburgh Parkway, South Chesapeake

1011 Cedar Tree Court, South Chesapeake
$684,824
4 Beds ⋅ 2.1 Baths ⋅ 10655903 MLS
Welcome to the popular Campbell model by Kirbor Homes, where thoughtfully designed spaces meet modern luxury. This home features a magnificent primary suite complete with a spacious walk-in closet, a spa-like ensuite featuring a freestanding tub, and a large bedroom designed for ultimate relaxation. The main level offers a dedicated home office, a cozy fireplace, and beautiful LVP flooring flowing throughout all main living areas. At the heart of the home, the extended kitchen provides ample counter space and storage, making entertaining effortless. Practical details like built-in mudroom cubbies keep daily life organized, while the rear covered porch offers the perfect outdoor retreat to unwind. Contact us today to learn more and explore options for your new home!

1011 Cedar Tree Court, South Chesapeake

1415 Rollesby Way, South Chesapeake
$330,000
2 Beds ⋅ 2.1 Baths ⋅ 10655885 MLS
Space, versatility & well-cared for condo in the heart of Greenbrier area of Chesapeake! At nearly 1900 sqft, the design of this floorplan outshines others by offering flexibility, function & storage. Upon entry, you're welcomed in by the warm native koa inspired LVP flooring. The living space naturally flows into the dining & kitchen areas for good times & making memories. The huge 1st floor flex room can be used as a 3rd bedroom, office, game room, etc. Sliding doors open to a cozy back patio with a storage shed. Upstairs find the spacious primary en suite with its large walk-in closet. The primary bathroom feels luxurious with a separate deep soak tub. The second en suite is spacious with its own walk-in closet & full bath. Neutral colors, well maintained systems, new garbage disposal & smart thermostat. Community pool, clubhouse & ample guest parking. Fees include water, sewer, trash, grounds & pool maintenance. Near shopping, highways & routes into Virginia Beach. Closing cost assistance available with full price offer!

1415 Rollesby Way, South Chesapeake

1885 Paw Paw Place, West Chesapeake
$611,214
4 Beds ⋅ 2.1 Baths ⋅ 10655732 MLS
The Persimmon is a stunning two story floor plan featuring a first floor bedroom and optional full bath, great for guests or multi-generational living. A welcoming foyer opens into an open-concept design showcasing a well-appointed kitchen with eat-in are and a large center island for gatherings and everyday living. The kitchen flows seamlessly into the family room creating an inviting space for connection & comfort just steps away from your patio expanding your outdoor living & entertaining space. Upstairs you will find a spacious loft providing a setting for family entertaining or relaxation. This level also features a luxurious owner's suite with spa-like bath with dual sinks. A conveniently located laundry room and two additional bedrooms offer comfort and functionality for the entire household. Call to schedule your personal your.

1885 Paw Paw Place, West Chesapeake

1108 Kathleen Lane, South Chesapeake
$1,195,000
5 Beds ⋅ 4.1 Baths ⋅ 10655222 MLS
This home truly has it all! Meticulously maintained & beautifully updated, this custom home sits on 3 acres offering space, privacy & versatility. Hardwood floors span the 1st & 2nd floors, complemented by plantation shutters. With 5 bedrooms, PLUS a finished room over the garage, there is room for everyone, including 3 bedrooms with ensuites .The 1st floor primary features a clawfoot tub & separate shower. A gorgeous kitchen with updated appliances & pot filler opens to the family room & bright sunroom with wood stove overlooking the saltwater pool. Outside, enjoy a low maintenance deck, attached 2-car garage, detached 2-car garage with unfinished 2nd floor & extra parking for a boat or RV. Brand new roof, updated HVAC ,remodeled bath & numerous additional improvements make this home truly move-in ready. Assumable 2.25% VA loan. This one is a must see!

1108 Kathleen Lane, South Chesapeake

539 Schaefer Avenue, West Chesapeake
$489,000
4 Beds ⋅ 2.1 Baths ⋅ 10655779 MLS
This beautifully maintained home that offers the look and feel of new construction. . . without the wait! Thoughtfully upgraded with custom finishes throughout, this home perfectly blends modern style with everyday comfort. Step inside to discover an open, light-filled floor plan featuring a stunning custom accent wall that adds warmth and character to the main living space. The spacious kitchen flows seamlessly into the dining and living areas for entertaining or spending time with family. Retreat to the generously sized bedrooms, each offering plenty of space for relaxation, a home office, or growing families. The primary suite provides a peaceful escape with exceptional closet space and a well-appointed ensuite bath. Conveniently located near shopping, dining, schools, and major highways. Schedule your private showing today!

539 Schaefer Avenue, West Chesapeake

1741 Fortune Terrace, South Chesapeake
$425,000
3 Beds ⋅ 2.1 Baths ⋅ 10655498 MLS
Welcome to your next home, where every day feels a little more special. Nestled in the highly sought-after Bryan's Cove community, this beautiful home offers more than just a place to live; it offers a lifestyle defined by comfort, convenience, and connection. Enjoy added privacy with a peaceful wooded backdrop and no rear neighbors. With a low condo fee, no flood insurance requirement, and zoning for the highly desirable Grassfield school district, this home truly checks all the boxes. Bryan's Cove is known for its scenic surroundings and exceptional amenities, offering the perfect blend of tranquility and everyday convenience. Residents enjoy access to a community dock, dog park, fitness center, clubhouse, and swimming pool. Nearby, you will find Publix, lots of other shopping and several restaurants, Tidewater Community College, and quick access to Interstates 64 and 264 makes commuting and daily errands effortless, while parks, recreation, and local attractions are all close by. Inside, you'll find a warm and inviting floor plan designed for both comfortable living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring a large center island with seating, abundant prep space, and a gas range that will delight home chefs. Every room has been thoughtfully designed to create a welcoming atmosphere where family and friends can gather and lasting memories can be made. Opportunities like this don't come along often. If you've been searching for a home in an exceptional community with outstanding amenities, top-rated schools, and a private, natural setting, this is one you won't want to miss. Schedule your private showing today and experience everything this remarkable home has to offer.

1741 Fortune Terrace, South Chesapeake

3145 Codorus Street, South Chesapeake
$500,000
4 Beds ⋅ 2.1 Baths ⋅ 10655704 MLS
Seller is offering $3,000 to be used at buyers discretion!!! Beautifully updated and move-in ready, this home offers the perfect blend of comfort, style, and community. Recent improvements include luxury vinyl plank flooring throughout, a beautifully renovated primary bath with a spacious walk-in shower, and the addition of a fourth bedroom for added flexibility. Outside, the large backyard is framed by mature weeping willow trees, creating a peaceful retreat on a quiet side street. Beyond your front door, enjoy a lifestyle that’s hard to find—golf cart rides to the clubhouse, afternoons at the resort-style pool, workouts in the fitness center, visits to the dog parks and playgrounds, and a calendar full of neighborhood events including community picnics, book club, cigar & bourbon nights, festive holiday celebrations, and the beloved Christmas golf cart parade. Experience everything this vibrant, close-knit community has to offer in sought-after Culpepper Landing.

3145 Codorus Street, South Chesapeake

804 Brookside Arch, South Chesapeake
$737,000
4 Beds ⋅ 3 Baths ⋅ 10655495 MLS
Welcome to this beautifully updated all-brick ranch home in sought-after Emerald Lakes in southern Chesapeake, Virginia. This 2,777-square-foot home offers 4 bedrooms, 3 full baths, one-level living & a 2-car side-load garage on a 1/2-acre cul-de-sac lot. The gourmet kitchen features quartz countertops, a 5-burner gas cooktop, GE Profile stainless appliances, double oven & butler’s pantry, with both an eat-in kitchen & formal dining room. Primary suite w/private bath plus separate en-suite bedroom—ideal for multigenerational living—and two additional bedrooms. Cathedral ceilings, hardwood floors, a gas fireplace & flexible office/library space. The saltwater inground pool, stone patio, gazebo & large outdoor fireplace create an exceptional private entertaining space. New pool salt cell with Wi-Fi controls, encapsulated crawl space with dehumidifier, approximately 3-year-old roof and 2-year-old water heater. Convenient to the NC line, Moyock & the NC Outer Banks.

804 Brookside Arch, South Chesapeake

518 Whisper Walk, South Chesapeake
$465,900
4 Beds ⋅ 2.1 Baths ⋅ 10655312 MLS
Welcome home to this beautifully maintained condominium in the highly sought-after Cedar Crossing community. This spacious open concept residence offers over 2,000 square feet of comfortable living space. Four bedrooms featuring a large primary bedroom suite on first level, with double vanity and large walk-in closet. Beautiful hardwood floors, and crown molding throughout. Tile in kitchen, bathrooms and mudroom. Enjoy the privacy of a fenced backyard with storage shed for additional equipment. Two car garage and driveway space. Neighborhood has a well-equipped playground, swimming pool, tennis court and clubhouse. Enjoy low-maintenance living in a vibrant community conveniently located near shopping, dining, schools, and major commuter routes.

518 Whisper Walk, South Chesapeake

2207 Edwin Drive, South Chesapeake
$597,740
3 Beds ⋅ 3 Baths ⋅ 10655508 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2207 Edwin Drive, South Chesapeake

MM James 2, South Chesapeake
$720,000
5 Beds ⋅ 3 Baths ⋅ 10655465 MLS
Model Home to Be Built - James II Model at Riverview Landing by Wetherington Homes. This thoughtfully designed floor plan offers an Owner's Suite, two additional bedrooms, and a utility room conveniently located on the first floor. Buyers may select their lot and personalize available design options. The home includes a variety of well-appointed features designed to support modern living. The community offers eight floor plan options along with multiple exterior elevations that highlight architectural detail and curb appeal. Contact us today for additional information, to join the VIP interest list, and to schedule an appointment. Discover the opportunity to build in this thriving new community in Chesapeake!

MM James 2, South Chesapeake

204 Henry Jefferson Way, South Chesapeake
$709,990
4 Beds ⋅ 3 Baths ⋅ 10655470 MLS
The Savannah offers a well-designed floor plan with a spacious great room centrally located, creating a natural flow into the kitchen and dining area—great for everyday living and gatherings. The home features four generously sized bedrooms, including an owner’s suite positioned at the rear of the home for added privacy. The owner’s suite includes direct access to the covered porch and two large closets. A flexible space just off the foyer provides versatility for use as a home office, additional living area, or formal dining space, depending on your needs. The second floor includes an additional bedroom, a full bath, and a loft area, offering extra living options for guests or multi-functional use. Thoughtful layout and functional spaces make the Savannah a comfortable and adaptable home.

204 Henry Jefferson Way, South Chesapeake

3240 Morningside Drive, West Chesapeake
$550,000
3 Beds ⋅ 2.1 Baths ⋅ 10655418 MLS
Welcome to this charming 2-story Colonial nestled in the heart of Western Branch! This 3 bedroom, 2.5 bath home offers comfortable living with a finished room over the garage that provides versatile space for an office, hobby room, or additional living area. The temperature-controlled all-season sunroom is a wonderful spot to relax and enjoy the changing seasons. Over the past 10 years, the owners have made numerous updates throughout the home, including improvements to the kitchen, bathrooms and more. Outside, enjoy the convenience of an in-ground sprinkler system and a full -yard electric fence. Ideally located near interstate access, shopping, dining, and everyday conveniences, this home offers both comfort and functionality in Western Branch location.

3240 Morningside Drive, West Chesapeake

716 Tallahassee Drive, South Chesapeake
$545,000
4 Beds ⋅ 2.1 Baths ⋅ 10655350 MLS
Exceptional opportunity in the sought-after Etheridge Lakes community located in the highly desirable Hickory High School district! This well-maintained 4 Bedroom, 2.5 Bath home offers comfort, space, and peace of mind with a NEW ROOF installed in 2026. The home features a functional layout perfect for everyday living and entertaining, with spacious bedrooms and plenty of natural light throughout. Versatile room downstairs for office needs or additional living area. All appliances convey, making this home truly move-in ready. Fenced yard offering privacy, yard space for pets or entertaining. 3 TVS convey! Enjoy the benefits of a well-established neighborhood with NO HOA fees or restrictions. Conveniently located near shopping, dining, parks, and major commuting routes, this home combines value, location, and pride of ownership in one outstanding package

716 Tallahassee Drive, South Chesapeake

Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.