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1441 Whittamore Road, South Chesapeake
$455,000
5 Beds ⋅ 2 Baths ⋅ 10659859 MLS
Welcome to a rare opportunity in Chesapeake's sought-after Hickory school district! Set on a full acre, this beautifully transformed 5-bedroom, 2-bath home offers the space and setting to enjoy a touch of country living while staying near the conveniences of the city. The renovation goes far beyond cosmetics, with a new roof, siding, windows, HVAC, flooring, carpet, plumbing, septic tank, appliances and more. Inside, fresh modern finishes create a bright, move-in-ready home with room for everyone. Outside, the expansive acre lot opens the door to gardens, outdoor entertaining, hobbies, animals or simply having more room to enjoy the outdoors. With golf courses nearby and easy access to everything Chesapeake has to offer, this property delivers a unique blend of space, location and modern living. Nearly everything has been refreshed or replaced- just bring your furniture and start enjoying the Hickory lifestyle!

1441 Whittamore Road, South Chesapeake

1072 Mesa Loop, South Chesapeake
$500,000
4 Beds ⋅ 3.1 Baths ⋅ 10659945 MLS
Ready Now:LuxuryTownhome w/2-car garage, covered entry,fenced front yard w/gate to multi trail,covered entry. 19x12 rear deck,LVP floors select areas.2nd floor:Kitchen center island w/shiplap, GE Cafe Matte Black appliances w/refrigerator,pantry,living area w/linear fireplace w/ shiplap surround w/built ins,dining area access to covered front deck.3rd flr: Primary:tile shower 2-shower heads, dual sinks, 2 closets, 2 bedrooms, full hall bath, linen closet, laundry. 1st floor flex room/bedroom dual entry bath, mudroom. Quartz tops in kitchen and baths-designer mirrors, wood shelving in all closets. Pet Friendly. Quiet easy lifestyle with the comfort of quality construction & name brand building materials including James Hardie Fire Retardant Fiber Cement Board. 2-10 home warranty, master insurance, trash pick up, private streets, city water/sewer, guest parking, multipurpose trails with lake and fountain. Only 56 homes. Central location in the Greenbrier area. .

1072 Mesa Loop, South Chesapeake

632 Willow Oak Drive, South Chesapeake
$470,000
4 Beds ⋅ 2 Baths ⋅ 10659611 MLS
Welcome to 632 Willow Oak Drive, where timeless character, inviting spaces, and room to make it your own come together! This charming 4-bedroom, 2-bath brick home offers a versatile layout with two separate living areas, perfect for relaxing, entertaining, or creating spaces that suit your lifestyle. Step inside to discover warm wood accents, beautiful architectural details, and a formal dining room featuring elegant crown molding, chair rail detailing, and a chandelier. The spacious kitchen offers abundant wood cabinetry, stainless steel appliances, generous counter space, and a nearby breakfast area. The second living area is full of character, showcasing exposed wood ceiling beams, rich wood paneling, built-in shelving, and a striking brick wood-burning fireplace, fully functional and ready for cozy evenings. Three main-level bedrooms and a fourth upstairs provide flexibility for guests, hobbies, or a home office. Outside, a covered front porch welcomes you home, while the spacious, fully fenced backyard offers mature shade trees, an outdoor patio, and a storage shed. An attached garage provides additional parking and storage. With its distinctive charm, multiple gathering spaces, and opportunities to add your personal touches, this home offers a wonderful canvas for its next chapter!

632 Willow Oak Drive, South Chesapeake

817 Wickford Drive, South Chesapeake
$260,000
3 Beds ⋅ 2 Baths ⋅ 10658699 MLS
OPEN HOUSE SATURDAY 31 OCT FROM 2 PM TO 5 PM. 3 BEDROOM 2.0 BATH SINGLE STORY END UNIT TOWNHOME. LIVING ROOM LAMINATE WOOD FLOOR, BOOKSHELVING, LIGHTED CEILING FAN AND BRICK FIREPLACE. OPEN DINING AREA TO THE UPDATED KITCHEN, BREAKFAST BAR AREA, STAINLESS APPLIANCE PACKAGE, REFRIGERATOR, SMOOTH TOP STOVE, BUILT IN MICROWAVE/DISHWASHER, DOUBLE STAINLESS SINK. PRIMARY SUITE LIGHTED CEILING FAN AND WALK-IN CLOSET. PRIMARY BATH RAISED VANITY TUB/SHOWER. LAUNDRY AREA CABINET AND SHELVES. TWO ADDITIONAL BEDROOMS, FULL HALL BATH, TUB/SHOWER, MARBLE TOP VANITY, LVP PLANK FLOOR, MEDICINE CABINET AND OVAL MIRROR. FEATURES: NEW ROOF, NEWER PAINT AND FLOORING, DIGITAL AC THERMOSTAT, UPGRADED BLINDS, CEILING FANS, STORMDOOR, PRIVACY FENCED BACKYARD, PATIO, TREES, STORAGE SHED, SIDE BY SIDE DRIVEWAY PARKING. AVAILABLE FOR QUICK CLOSING.

817 Wickford Drive, South Chesapeake

405 Bridle Court, South Chesapeake
$485,000
4 Beds ⋅ 3 Baths ⋅ 10659847 MLS
Move-in ready and packed with so many thoughtful upgrades and extras that set it apart, this beautifully maintained 4 bed/3 FULL bath brick ranch offers so much more than meets the eye! Tucked away on a quiet cul-de-sac and sitting on a half-acre lot, the home welcomes you with a generous front porch and features a fully fenced backyard offering plenty of room for outdoor entertaining, gardening, recreation, or simply enjoying the privacy and space. The fully renovated kitchen stuns with quartz countertops, KitchenAid professional appliances, tile backsplash, convection gas range, recessed dimmable lighting, soft-close white cabinetry, and a double pantry offering exceptional storage. A comfortable and versatile floor plan features spacious living and dining areas, A cozy den with a wood-burning fireplace provides a welcoming place to gather, while the expansive sunroom with sliding glass doors offers a bright and relaxing retreat overlooking the backyard. The finished room over the garage serves as the fourth bedroom providing flexibility and privacy for guests, a home office, or additional living space. The impressive list of extras continues with a new HVAC system, extra large fire-pit, an oversized garage, a large detached storage shed, large walk-in attic for additional storage and wiring for a backup generator. Don't miss out on your chance for this truly a one-of-kind gem!

405 Bridle Court, South Chesapeake

605 Tuskegee Avenue, South Chesapeake
$370,000
3 Beds ⋅ 2.1 Baths ⋅ 10659814 MLS
Nestled in the heart of Crestwood, this 3 bed 2.5 bath home is waiting for its new owners! Major improvements provide peace of mind, including; HVAC (2026), all new Deck (2026), Restored Crawlspace (2026), and Roof (2023). The layout provides functionality in your every day living. Downstairs you'll find large dining area and breakfast nook, living room with cozy fireplace, and a large deck to enjoy your backyard, as well as a guest bath and laundry room off the garage entry. Upstairs, is a large Primary bedroom that features 2 walk in closets and the ensuite bathroom with beautifully tiled shower. 2 spacious bedrooms and another full bathroom finish out the upstairs area. Conveniently located minutes from shopping, restaurants and schools, and direct access to interstates makes for easy daily commute. Call for your private showing today! Some photos have been virtually staged.

605 Tuskegee Avenue, South Chesapeake

3260 Hancock Drive, South Chesapeake
$399,900
4 Beds ⋅ 2 Baths ⋅ 10659862 MLS
Charming ranch in the desirable Strawberry Acres neighborhood. The cozy family room opens to an additional den and eat-in kitchen. The kitchen offers plenty of cabinet and counter space and stainless steel appliances, including a newer refrigerator (2023) and dishwasher (2025). All three bedrooms are nicely sized, with the primary bedroom offering an en-suite bathroom. Outside, enjoy a large, fully fenced backyard with a patio, covered deck, and expansive grassy area. The oversized detached two-car garage offers room for parking, extra storage, a workshop, or a home gym. Recent updates include a roof replaced in 2022 and new gutters installed in 2026. 4th Bedroom is the converted garage which does not have a closet. Schedule your private tour today!

3260 Hancock Drive, South Chesapeake

1674 Benefit Road, South Chesapeake
$425,000
3 Beds ⋅ 1.1 Baths ⋅ 10659765 MLS
Two homes, one opportunity at 1672 & 1674 Benefit Road! These two neighboring properties are being sold together, giving you three separate living spaces on adjoining lots. The main home at 1674 is a charming 3-bedroom, 1.5-bath home with a welcoming covered front porch, a spacious yard, and a long driveway. Inside, you’ll find luxury vinyl plank flooring, bright bedrooms with ceiling fans, and an updated kitchen with white cabinetry, granite-look counter tops, and modern appliances. Out back, the garage has been fully converted into a code-compliant 2-bedroom, 2-bath apartment with its own entrance. It features a stylish galley kitchen with stainless appliances, in-unit laundry, durable LVP flooring, and a subway-tile walk-in shower with a built-in bench and pebble floor. Next door, 1672 is a 3-bedroom, 2-bath brick ranch that’s ready for your personal touch and adds even more space and income potential. This property can work for you in several ways. For multi generational living, keep loved ones close while everyone has their own kitchen, entrance, and privacy. Aging parents, adult children, and long-term guests can each have a place of their own, just steps away. To house hack, live in one home and let the other two help cover your mortgage, building equity and wealth while you live there. As an investor, hold all three as long-term rentals for three income streams in one purchase and one location. Best of all, the property can change with you: start as a family property today and convert it to rental income later, or the other way around. Opportunities like this rarely come to market. So bring your vision and schedule your showing today!

1674 Benefit Road, South Chesapeake

1672 Benefit Road, South Chesapeake
$225,000
3 Beds ⋅ 2 Baths ⋅ 10659764 MLS
Two homes, one opportunity at 1672 & 1674 Benefit Road! These two neighboring properties are being sold together, giving you three separate living spaces on adjoining lots. The main home at 1674 is a charming 3-bedroom, 1.5-bath home with a welcoming covered front porch, a spacious yard, and a long driveway. Inside, you’ll find luxury vinyl plank flooring, bright bedrooms with ceiling fans, and an updated kitchen with white cabinetry, granite-look counter tops, and modern appliances. Out back, the garage has been fully converted into a code-compliant 2-bedroom, 2-bath apartment with its own entrance. It features a stylish galley kitchen with stainless appliances, in-unit laundry, durable LVP flooring, and a subway-tile walk-in shower with a built-in bench and pebble floor. Next door, 1672 is a 3-bedroom, 2-bath brick ranch that’s ready for your personal touch and adds even more space and income potential. This property can work for you in several ways. For multi generational living, keep loved ones close while everyone has their own kitchen, entrance, and privacy. Aging parents, adult children, and long-term guests can each have a place of their own, just steps away. To house hack, live in one home and let the other two help cover your mortgage, building equity and wealth while you live there. As an investor, hold all three as long-term rentals for three income streams in one purchase and one location. Best of all, the property can change with you: start as a family property today and convert it to rental income later, or the other way around. Opportunities like this rarely come to market. Properties must be purchased together, so bring your vision and schedule your showing today!

1672 Benefit Road, South Chesapeake

no property photo
$499,900
4 Beds ⋅ 2 Baths ⋅ 10659700 MLS
Nestled in the heart of Greenbrier, this move-in-ready 4-bedroom home offers a bright and welcoming atmosphere from the moment you step inside. Soaring cathedral ceilings and skylights fill the main living space with natural light, creating a balance of open-concept entertaining areas and comfortable, cozy corners. Adapt the versatile room off the kitchen to suit your lifestyle, whether as a formal dining room, quiet home office, or vibrant playroom. Thoughtfully updated with modern kitchens, bathrooms, and flooring, plus peace-of-mind upgrades from 2023 including a new HVAC, air ducts, insulation, and water heater. Retreat to the primary suite featuring a walk-in closet and a spacious updated bathroom. All of this is located just minutes away from Greenbrier shopping and Greenbrier Country Club.

744 Norcova Drive, South Chesapeake

314 Sussex Court, South Chesapeake
$310,000
2 Beds ⋅ 2.1 Baths ⋅ 10659701 MLS
Rare opportunity to own a well-maintained brick end unit townhome nestled on a quiet cul-de-sac with nearly an acre of land, no HOA fees, private dock and water access rights. This home features new roof, fresh paint, new gas logs, and countertops. New AC unit with 10 year warranty and updated furnace. This newly fenced back yard has a small shed and larger detached workshop with power! This private yard and large deck are great for relaxing and entertaining. Inside, you'll find 2 spacious bedrooms with ensuite bathrooms making it great for comfort and privacy. Large walk-in attic and utility closet with storage. With no HOA fees and a rare setting that allows for waterfront enjoyment and lots of outdoor space, you won't want to miss this one-of-a-kind opportunity! Inground sprinkler, shed, dock, Primary decorative fireplace, and well-As is! Schedule your showing today! Can close quickly.

314 Sussex Court, South Chesapeake

820 Stacey Place, South Chesapeake
$459,520
3 Beds ⋅ 2.1 Baths ⋅ 10659594 MLS
Tucked away at the end of a quiet cul-de-sac on over a 1/2 acre, this home offers a serene, park-like setting with exceptional privacy and space to enjoy. Inside, you’ll find attractive LVP and Ceramic flooring throughout the main level and a bright, open-concept layout designed for modern living. The spacious living area flows seamlessly into a stylish kitchen featuring quartz countertops—perfect for both everyday living and entertaining.A large two-car attached garage provides ample storage, while the expansive backyard offers endless possibilities, including plenty of room to add a pool or create your own outdoor retreat. Upstairs, the generous primary suite boasts two walk-in closets, complemented by two additional bedrooms for a total of three. A conveniently located upstairs utility room includes a washer and dryer that convey with the home.Ideally situated near shopping, dining, and major interstates, this property combines peaceful living with everyday convenience.

820 Stacey Place, South Chesapeake

1108 Sword Drive, South Chesapeake
$369,900
4 Beds ⋅ 2 Baths ⋅ 10659368 MLS
Welcome to 1108 Sword Dr, a beautifully updated 4-bedroom, 2-bath ranch-style home offering approximately 1,800 sqft of comfortable single-level living in Chesapeake, VA. Freshly painted throughout, this move-in-ready home features a bright, open-concept floor plan with LVP flooring throughout the main living areas, carpeted bedrooms, and updated light fixtures. The kitchen features granite countertops, stainless steel appliances, and an open layout that flows seamlessly into the living and dining areas. Both bathrooms have been updated, adding to the home’s fresh, modern feel. Additional improvements include a new roof. Step outside to a large, fully fenced backyard with plenty of space for entertaining, pets, play, gardening, or simply relaxing outdoors. If you’re searching for a move-in-ready 4-bedroom ranch home for sale in Chesapeake, Virginia with approx. 1,800 sqft an open floor plan, modern updates, and a spacious fenced backyard, 1108 Sword Dr is one you’ll want to see!

1108 Sword Drive, South Chesapeake

720 Hunters Quay, South Chesapeake
$299,000
3 Beds ⋅ 2.1 Baths ⋅ 10659243 MLS
Fresh, bright and move-in ready! Welcome home to 720 Hunters Quay, a charming 3 bedroom, 2.5 bath brick-front townhome for sale in Chesapeake, VA with no HOA and nothing left to do but unpack. Out front, a classic brick facade, a welcoming front stoop and tidy landscaping deliver instant curb appeal. Inside, fresh neutral paint and durable luxury vinyl plank (LVP) flooring flow through the main level, giving this home a clean, modern feel you will love from the very first step. The updated kitchen is ready for anything, with crisp white shaker-style cabinets, sparkling granite countertops, a handy pantry and a full appliance package including the refrigerator, range, microwave and dishwasher. Host dinner in the separate dining room with chair-rail trim and a stylish chandelier, then gather around the wood-burning fireplace in the living room on cool Virginia evenings. Sliding glass doors open to a private, fully fenced backyard with a patio, made for grilling, gardening, morning coffee and room for pets to play. Upstairs, the spacious primary suite shines with a vaulted ceiling, ceiling fan, walk-in closet and its own private full bath with a granite vanity. Two more generous bedrooms with ceiling fans offer flexible space for guests, a home office, a gym or hobbies, and the hall bath features a fresh granite vanity too. A convenient main-level half bath, central air, natural gas heat and two off-street parking spaces plus street parking make everyday living easy. Tucked into the Hunters Glen community, you are just minutes from Oak Grove Lake Park, Greenbrier and Great Bridge shopping and dining, and quick commuter routes to I-64 and I-464. Updated townhomes at this price go fast in Chesapeake, so come see it today!

720 Hunters Quay, South Chesapeake

1540 Eldwick Drive #307, South Chesapeake
$325,130
2 Beds ⋅ 2 Baths ⋅ 10659135 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Rowen model is a corner location that features an open-concept floorplan, high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms and 2 baths. Owner’s suite includes a private bath and walk-in closet with custom wood shelving. Enjoy a patio or balcony space off living room. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #307, South Chesapeake

1540 Eldwick Drive #206, South Chesapeake
$295,130
2 Beds ⋅ 2 Baths ⋅ 10659134 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Addison model features an open-concept floorplan & high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with center island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms & 2 baths. Owner’s suite includes a private bath & walk-in closet with custom wood shelving. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #206, South Chesapeake

1540 Eldwick Drive #104, South Chesapeake
$320,130
2 Beds ⋅ 2 Baths ⋅ 10659133 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Addison model features an open-concept floorplan & high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with center island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms & 2 baths. Owner’s suite includes a private bath & walk-in closet with custom wood shelving. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #104, 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.

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