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237 Castleberry Drive, South Chesapeake
$758,900
6 Beds ⋅ 3 Baths ⋅ 10653849 MLS
Set on more than half an acre in a quiet Great Bridge cul-de-sac, this all-brick 6-bedroom, 3-bath home offers space, flexibility, and thoughtful upgrades throughout. The spacious layout features a two-story foyer, formal dining room, private office/study, and an open living area leading to a well-appointed kitchen with granite countertops, center island, gas cooking, double ovens, stainless appliances, beverage fridge, and wine storage. A first-floor bedroom and full bath are ideal for guests or multigenerational living. Upstairs, the primary suite offers three walk-in closets, plus additional bedrooms, laundry, and a media room. Enjoy the expansive fenced backyard with a 10x16 shed, sprinkler system, and plenty of room to entertain. Additional features include a built-in generator, tankless gas water heater, surround sound, and two-car garage.

237 Castleberry Drive, South Chesapeake

900 Golden Cypress Court, South Chesapeake
$425,000
5 Beds ⋅ 2 Baths ⋅ 10653879 MLS
Tucked at the end of a quiet cul-de-sac in the heart of Greenbrier, one of Chesapeake’s most desirable areas, with easy interstate access to everything! Situated on a large 11,327 sq ft lot, this home features a fenced backyard, large shed, firepit, front & rear decks, mature cypress tree & Japanese maple. Inside offers an open-concept layout, luxury vinyl tile, built-in entertainment cabinet & spacious primary bedroom (15’3”x19’) with large walk-in closet. Kitchen features double oven, new 36” SS gas cooktop, glass electric cooktop, new SS refrigerator & dishwasher. Updates include new roof, siding, carpet, blinds & 3/4-glass front door. Additional features include 2 hotel-style shower valves, 2 commercial thermostats, hot water recirculating pump & laundry room with deep sink. Heated & cooled 2-car garage includes workbench & extensive cabinetry, plus 4 off-street parking spaces and a beautifully landscaped yard.

900 Golden Cypress Court, South Chesapeake

302 Honey Locust Way Way, South Chesapeake
$650,000
4 Beds ⋅ 2.2 Baths ⋅ 10653782 MLS
Former Home-A-Rama award-winning home with character you simply don't find every day. Tucked away on a .43-acre cul-de-sac lot, this 3-story Victorian-style home offers approximately 3,100 sq. ft. of living space and a wrap-around porch. Inside you'll find hardwood floors, generous living and dining spaces, custom details, two fireplaces and two staircases. The gourmet kitchen features quartz countertops, black stainless appliances, custom cabinetry, island and pantry. Spacious bedrooms lead to an impressive primary suite with walk-in closet, ensuite bath and fireplace. A third-level bonus space offers flexibility for an office, study or workout room. Outside, an in-ground saltwater pool, multi-level deck, gazebo, fire pit and expansive backyard create a setting for entertaining or relaxing. A truly unique home ready for its next chapter!

302 Honey Locust Way Way, South Chesapeake

808 Bay Laurel Court, South Chesapeake
$634,000
4 Beds ⋅ 3.1 Baths ⋅ 10653860 MLS
Welcome home to this beautiful brick home, ideally situated on a large corner lot in a cul-de-sac in Chesapeake’s desirable Cedarwood community. Offering more than 3,000 square feet, this move-in-ready home features an open, light-filled floor plan with tall ceilings and gorgeous wood flooring. The spacious kitchen flows seamlessly into the living area, creating the perfect setting for entertaining. Relax beside the wood-burning fireplace surrounded by charming built-in shelving, or enjoy the backyard with its generous deck, gazebo and delightful garden house. Two primary bedrooms with private full baths provide wonderful flexibility for guests or multigenerational living. Other highlights include updated bathrooms, upgraded windows and architectural shingles. New refrigerator installed in 2026. All appliances convey. A two-car attached garage and additional street parking, conveniently located near shopping, dining and sought-after Chesapeake schools. Schedule your private tour today!

808 Bay Laurel Court, South Chesapeake

832 Woodrow Court, South Chesapeake
$510,000
4 Beds ⋅ 2 Baths ⋅ 10653661 MLS
Welcome to this exceptionally clean and well-maintained home tucked away at the end of a quiet cul-de-sac. The inviting floor plan offers 3 bedrooms plus a spacious room over the garage, providing flexible space for a home office, recreation room, or additional living area. The kitchen features a comfortable breakfast area, while the wood-burning fireplace adds warmth and character to the main living space. Enjoy relaxing in the cozy sunroom overlooking a very private, fully fenced backyard with privacy fencing—perfect for outdoor enjoyment and entertaining. Additional features include a separate utility room, efficient geothermal heating and cooling system, and low-maintenance exterior trim. The seller is installing a new roof and will provide a clear termite and moisture letter, offering added peace of mind. Conveniently located within the Great Bridge school attendance area. This home has been carefully maintained, is move-in ready, and is priced to sell. Put this one at the top of your showing list before the opportunity is gone!

832 Woodrow Court, South Chesapeake

1232 New Born Court, South Chesapeake
$450,000
5 Beds ⋅ 2.1 Baths ⋅ 10653581 MLS
Welcome home! This beautiful home in Chesapeake is ready for its new owners! With 5 bedrooms, 2.5 bathrooms, and a layout designed to offer the perfect balance of togetherness and privacy, there is room for everyone. The kitchen offers plenty of cabinets and counter space and flows right into the open dining/living area. Two separate living spaces provide flexibility for entertaining, relaxing, or everyday living. Outside, enjoy a spacious backyard with a great deck, storage shed, and even a chicken coop! Located in a highly sought-after school district and a close proximity to shopping, dining and interstate access, this house checks all the boxes! Shed and chicken coop convey as-is. Don't let this one get away - call today to schedule your tour!

1232 New Born Court, South Chesapeake

1914 Keeter Run, South Chesapeake
$440,000
4 Beds ⋅ 2.1 Baths ⋅ 10653149 MLS
Welcome home to Greenbrier! This beautifully maintained, move in ready home is tucked away on a desirable cul-de-sac in the heart of Chesapeake. Featuring numerous recent updates, you can move in with confidence and enjoy! The kitchen was updated in 2023 with new cabinets, countertops, and appliances. All bathrooms were refreshed in 2024 with new vanities, sinks, tubs, toilets, flooring, and paint. Major updates include a roof (2017), fence (2021), HVAC furnace (2025), condenser(2026), and water heater (2026). The first floor offers a spacious foyer, open living and dining areas, plus flexible bonus space great for a home office or playroom. Upstairs features a large primary suite with private bath and walk-in closet, three additional bedrooms, and a spacious shared bath. Conveniently located near Greenbrier shopping, dining, interstates, and local attractions. Don't miss your opportunity to make this home yours!

1914 Keeter Run, South Chesapeake

804 Wakedale Arch, South Chesapeake
$719,900
5 Beds ⋅ 4 Baths ⋅ 10653264 MLS
Nestled on a cul-de-sac in Saddle Ridge Estates with NO HOA, 804 Wakedale Arch offers 3,720 square feet of spacious living with five bedrooms and four full baths. New hardwood floors, new carpet, and fresh paint throughout make this home move-in ready. An expansive sunroom just off the eat-in kitchen provides additional space for entertaining or relaxing. The generously sized primary suite features a sitting area, walk-in closet, and private bath with dual vanities, a separate shower, and soaking tub. A first-floor bedroom and full bath offer flexibility for guests or multigenerational living. Enjoy practical extras, including ample built-in garage shelving and a backyard shed with electricity. Space, comfort, and convenience come together in this beautifully refreshed home!

804 Wakedale Arch, South Chesapeake

412 Harper Court, South Chesapeake
$575,000
5 Beds ⋅ 3.1 Baths ⋅ 10653159 MLS
A rare financing opportunity and an exceptional floor plan set this completely renovated 5-bedroom, 3.5-bath home apart. Qualified buyers may be eligible to assume the seller’s existing VA loan at an incredible 2.625% interest rate, subject to servicer approval and existing loan terms. The versatile layout provides flexibility for extended family, guests, private workspaces and everyday living. Imagine cooling your home and enjoying the pool all summer with an electric bill that is virtually nonexistent. The seller reports exceptional energy savings from the solar-panel system, which will convey free and clear at closing. Other major improvements include new vinyl siding, garage door, HVAC, tankless water heater, fresh paint and so much more. The backyard paradise features a heated saltwater above-ground pool, new privacy fence and dedicated pool room that can also serve as a workout or recreation space. A well and sprinkler system help maintain the grounds.

412 Harper Court, South Chesapeake

952 Checkerspot Way, South Chesapeake
$685,000
5 Beds ⋅ 2.1 Baths ⋅ 10652920 MLS
Welcome to a home where thoughtful design meets effortless comfort. Beautifully updated with brand-new LVP flooring, this inviting residence is enhanced by an impressive collection of custom upgrades. The primary suite features a California Closets custom system, while the office offers tailored shelving and storage. In the kitchen’s eat-in area, a dedicated dog station and additional pantry provide both style and everyday functionality. Step outside and discover a private backyard backing to peaceful woods, complete with a fire pit—for relaxing or entertaining under the stars. The screened-in porch offers another inviting space to unwind and enjoy your favorite show. With the neighborhood playground just across the street, this home blends privacy, convenience, and thoughtful details in all the right ways. A home this special deserves to be seen!

952 Checkerspot Way, South Chesapeake

508 Schaefer Avenue, West Chesapeake
$509,900
4 Beds ⋅ 2.1 Baths ⋅ 10653139 MLS
Welcome to 508 Schaefer Avenue, a beautifully maintained 2018-built home in Chesapeake’s Deep Creek area! With 4 bedrooms, 2.5 baths, and 2,398 square feet, this home offers the space today’s buyers are looking for. The main level features an open flow between the kitchen, dining, and living areas, along with a separate front flex room ideal for a home office, playroom, or sitting room. The bright kitchen includes white cabinetry, granite countertops, a large island with seating, and stainless steel appliances. Upstairs, the spacious primary suite includes a separate sitting area and an ensuite bath with dual vanities, a soaking tub, and a separate glass shower. Three additional bedrooms and an upstairs laundry room add everyday convenience. Outside, enjoy a level backyard, concrete patio, wooded backdrop, and attached two-car garage. Potential 5.75% assumable loan opportunity for qualified buyers, subject to lender/servicer approval, underwriting, applicable terms, and buyer qualification. Schedule your private showing today!! THIS ONE IS A STEAL!!!

508 Schaefer Avenue, West Chesapeake

418 Supplejack Court, South Chesapeake
$485,000
4 Beds ⋅ 2.1 Baths ⋅ 10652092 MLS
Gorgeous renovated 4-bedroom, 2.5-bath home in sought after Riverwalk perfectly situated on a cul-de-sac. Open floor plan filled with natural light and stylish upgrades throughout. Stunning kitchen with custom cabinets, butcher block countertops, stainless-steel appliances and amazing center island. The formal dining room and cozy living room with fireplace offer ideal spaces for entertaining or relaxing. The primary ensuite has vaulted ceiling, double sink vanity, stunning shower and walk in closet. Enjoy relaxing on the oversized back deck for a peaceful backyard retreat. Additional highlights include a generous walk-in attic, oversized 2-car garage, and excellent storage throughout. Residents enjoy access to amenities including a clubhouse, swimming pool, playground, tennis courts, scenic trails, and a boat ramp and dock on the Elizabeth River. Close to beaches, military bases, amazing restaurants, shopping and more. Fantastic home and vibrant community!

418 Supplejack Court, South Chesapeake

2916 Mintwood Drive, West Chesapeake
$275,000
3 Beds ⋅ 2 Baths ⋅ 10652244 MLS
REAL ESTATE AUCTION – PRICE SHOWN IS THE ADVERTISED STARTING BID, NOT THE SELLER’S RESERVE OR GUARANTEED SALE PRICE. This single-story brick ranch offers approximately 1,564 square feet with 3 bedrooms, 2 full bathrooms, an attached garage and a 0.332-acre lot. Live on-site auction Saturday, October 24, 2026, at 11:00 a.m. Reserve auction subject to seller confirmation. A 10% buyer’s premium will be added to the accepted high bid to determine the contract purchase price. Successful bidder must provide the required $10,000 deposit and close within 30 to 45 days. Property is offered as-is, where-is, with all faults and without financing, appraisal, inspection or other contingencies. Pre-auction traditional real estate offers may be considered until 48 hours before the live auction. Sealed absentee bidding is available under the published auction terms. Public previews are scheduled for Saturday, September 19, and Saturday, October 10, at 11:00 a.m. Buyers should complete all inspections, financing arrangements and due diligence before bidding. Auction documents are available through the listing agent.

2916 Mintwood Drive, West Chesapeake

2809 Cistern Circle, South Chesapeake
$539,900
4 Beds ⋅ 2.1 Baths ⋅ 10651217 MLS
Welcome to 2809 Cistern Circle! This beautifully maintained home offers spacious living areas, abundant natural light, and a flexible floor plan with space for a home office or study. Smart Home Ready with Samsung SmartThings potential and compatible lighting, locks, cameras, thermostats, sensors, and more. The living room features built-in surround sound, and the garage offers two additional 240V outlets. Enjoy a large fenced backyard, deck, patio, and fire pit area. Community amenities include a pool, clubhouse, playground, picnic areas, and green space. A VA loan at a 3% interest rate may be assumable by a qualified buyer, subject to loan servicer approval and applicable terms. Ask for details about this potential financing opportunity!

2809 Cistern Circle, South Chesapeake

2001 Athens Court, South Chesapeake
$354,900
3 Beds ⋅ 1.1 Baths ⋅ 10651099 MLS
Water access, generous outdoor space, and exceptional garage possibilities make this ranch in the sought after Geneva Shores one to see! Situated on a cul-de-sac, this well maintained 3-bedroom, 1.5-bath home features beautiful hardwood floors, an updated kitchen with granite countertops, stainless-steel appliances, and beautiful soft close cabinetry and updated bathrooms. The fenced backyard features a deck and backs to the water with kayak access at high tide, plus homeowners have access to the neighborhood boat ramp. Car enthusiasts and hobbyists will appreciate the detached 2-car garage with 220V electrical service that is heated and cooled by a window unit, while an attached garage provides even more storage and parking options. Situated on approximately .45 acre, this property offers a unique combination of updates, water access, outdoor space, and hard-to-find garage space—all at the end of a cul-de-sac. Come see all this home has to offer!

2001 Athens Court, South Chesapeake

1629 Waterside Drive, South Chesapeake
$534,900
4 Beds ⋅ 2.1 Baths ⋅ 10651368 MLS
This stunning home combines waterfront living, a cul-de-sac location and the convenience of being just minutes from the heart of Greenbrier! Meticulously maintained and extensively refreshed, this 2,400 SF home offers 4 bedrooms, 2.5 baths, a spacious FROG & an expansive backyard overlooking the water. Watch the seasons change from your windows and enjoy the serene setting that water views provide. Major 2025 updates include dual HVAC systems, gas water heater, appliances, engineered hardwood floors, fresh interior paint, blinds, lighting, faucets, switches, receptacles, door hardware & more. The kitchen features new tile, backsplash & lighting, plus a large pantry. Enjoy a primary suite with walk-in closet, spa tub, tiled shower & double vanity. A large deck & pergola overlook the lawn and lake, complemented by mature landscaping, new fencing & a shed. Approx. 5 minutes to Greenbrier shopping, dining & the future Chesapeake Costco!

1629 Waterside Drive, South Chesapeake

700 Sarasota Arch, South Chesapeake
$595,000
4 Beds ⋅ 2.1 Baths ⋅ 10651170 MLS
Welcome to 700 Sarasota Arch, offering nearly 2,900 sq. ft. of versatile living space on a .36-acre cul-de-sac lot in Chesapeake's Etheridge Lakes community. This 4-bedroom, 2.5-bath home features a spacious floor plan designed for everyday living and entertaining. The family room is anchored by a gas fireplace with custom built-in bookcases, while the bright breakfast nook provides views of the backyard. A formal dining room adds additional space for gatherings and special occasions. The generous FROG serves as the fourth bedroom and offers flexibility for an office, media room, hobby space, or guest accommodations. Located within the Hickory School zone, this home combines space and flexibility. Bring your vision and make this home your own!

700 Sarasota Arch, South Chesapeake

3201 Letcher Court Court, South Chesapeake
$585,000
5 Beds ⋅ 2.1 Baths ⋅ 10651123 MLS
JUST THE HOME YOU'VE BEEN LOOKING FOR! WELCOME HOME TO THIS BEAUTIFUL 5BR 2.5 BTH 2 CAR GAR HOME OFFERING THE PERFECT BLEND OF SPACE, COMFORT, AND STYLE. DESIGNED WITH BOTH EVERYDAY LIVING AND ENTERTAINING IN MIND. FEATURES GENEROUSLY SIZED BEDROOMS/CLOSET SPACE, INVITING GATHERING SPACES TO INCLUDE A SUNROOM/FLEXROOM, PLUS A ROOM OVER GAR, 4 LINEN CLOSETS, EXTRA STORAGE SPACE AND A WELL-PLANNED LAYOUT SUITED FOR A VARIETY OF LIFESTYLES. TASTEFULLY DESIGNED 2 STORY FOYER WITH ARCHS/COLUMNS AND AN OPEN STAIRCASE AS YOU ENTER HAS A WOW EFFECT. THE KITCHEN HAS A CENTER ISLAND PENDANT LIGHTS, GLASS MOSAIC BACKSPLASH, NEW LIGHT FIXTURES, SAMSUNG MICROWAVE, NEW FAUCET AND MORE. LIKE NEW SS GAS RANGE AND DISHWASHER ARE HIGH END APPLIANCES BY LG. KITCHEN TRANSITIONS INTO THE MAIN LIVING AREA CREATING A WARM AND WELCOMING ENVIRONMENT FOR HOSTING FAMILY AND FRIENDS. PRIMARY SUITE IS A PRIVATE RETREAT WITH A JETTED TUB, SEPARATE SHOWER, HIS/HERS VANITIES, WATER CLOSET, AND A LARGE WALK IN CLOSET. NEW FENCE JUST INSTALLED. SHOWS PRIDE OF OWNERSHIP! MUST SEE TODAY BEFORE IT'S GONE!

3201 Letcher Court Court, South Chesapeake

1010 Cuervo Court, South Chesapeake
$599,900
5 Beds ⋅ 3 Baths ⋅ 10650705 MLS
PRICED TO SELL! Welcome to 1010 Cuervo Court, a spacious 5-bedroom, 3-bath home offering approximately 3,000 sq ft in sought-after Las Gaviotas! Flexible floor plan includes a first-floor bedroom and full bath, formal living room and a separate dining room. The large family room features cathedral ceilings, a stunning floor-to-ceiling brick fireplace, abundant natural light, and golf course views. Spacious primary suite offers a private balcony, large walk-in closet, and spa-like bath with dual vanities, jetted tub, and separate shower. Generously sized bedrooms, excellent closet space throughout, and a finished room over the garage provide plenty of space and flexibility. Additional features include a second level laundry room, side-loading 2-car garage, brand new dehumidifier recently installed in the crawlspace, newer carpet, and fresh paint in select rooms. Enjoy the charm of this established Chesapeake community with beautiful streets, golf course surroundings, cul dec sac living, walking trails, and highly regarded schools.

1010 Cuervo Court, South Chesapeake

MM Raccoon (Reba On 16-3) Trail, South Chesapeake
$755,166
3 Beds ⋅ 2.1 Baths ⋅ 10650490 MLS
Welcome home to the Reba floor plan by Kirbor Homes, situated on a picturesque 1+ acre cul-de-sac lot in Sanderson Estates! This 3-bedroom home offers a tranquil backdrop featuring scenic views of a neighboring pond and mature trees. Inside, enjoy a functional design complete with a spacious main-level layout with a spacious kitchen, breakfast area, and great room, along with an oversized 2-car garage with plenty of extra storage space. Low-maintenance living is made simple with a low HOA dedicated solely to community amenity maintenance. Great location just minutes from shopping, restaurants, and easy access to roadways to all areas of Coastal VA and NC. Serene views and room to spread out—schedule your consultation today to personalize your home details!

MM Raccoon (Reba On 16-3) Trail, South Chesapeake

801 Aston Place, South Chesapeake
$699,900
4 Beds ⋅ 2.1 Baths ⋅ 10650037 MLS
Resort-style living at the pinnacle of a premier Great Bridge cul-de-sac! This striking 3,600 sqft waterfront estate reveals a rare staycation lifestyle on a sprawling 0.68-acre lot. Step inside to an interior flooded with light, soaring ceilings, skylights, and a jaw-dropping stone fireplace. Over $60K was invested in seamless wood floors sweeping continuously across both levels. The main layout leads to a gourmet kitchen with white cabinets, quartz countertops, and a massive smart touchscreen refrigerator. Upstairs, a humongous primary suite awaits with a deep jacuzzi soaking tub. The backyard is a show-stopping private oasis on a tranquil pond: float in your 32K-gal saltwater pool with a brand-new liner, or entertain under the monumental 19x26 covered pavilion with dual refreshment fridges. End your nights stargazing in the brand-new 4-person hot tub. Absolute peace of mind with a brand-new architectural roof on the home and both storage workshops. Assumable 1.75% VA loan ($268K).

801 Aston Place, 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.