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1733 Head Of River Road, South Chesapeake
$839,900
4 Beds ⋅ 3 Baths ⋅ 10654135 MLS
Interior pics coming!! Welcome to the Hickory lifestyle, where space, privacy, & possibilities come together on 3 acres! This 4-bedroom, 3-bath home offers 2,912 square feet of comfortable living space & plenty of room to enjoy the outdoors. The kitchen features granite countertops & opens to the family room, creating an easy gathering space for everyday life. A formal living room & additional space provide room for an office, playroom, library, or whatever fits your needs. Upstairs, all four bedrooms are generously sized, including a spacious primary suite with a large bathroom featuring a separate walk-in shower & soaking tub & 2 walk-in closets! Outside, the in-ground pool sets the stage for relaxing afternoons at home. And with 3 acres to call your own, there’s room to dream—whether that means a vegetable garden, chickens, outdoor hobbies, or simply enjoying the extra elbow room that makes Hickory living so desirable. Come see all this home & its expansive setting has to offer!

1733 Head Of River Road, South Chesapeake

212 Kwanzan Court, South Chesapeake
$793,267
5 Beds ⋅ 3 Baths ⋅ 10654133 MLS
Discover the Bellhaven by Wetherington Homes at Riverview Landing, with an estimated October 2026 delivery! This beautifully designed 4-5 bedroom home blends thoughtful functionality with elevated finishes and an inviting open-concept layout. The chef-inspired kitchen features dual ovens, gas range, hood, oversized island, and a butler's pantry connecting seamlessly to the dining area., while the great room opens to a covered rear porch for effortless indoor-outdoor living. A versatile upstairs loft and main level full bath add valuable flexibility. Enjoy a curated selection of luxury upgrades designed to elevate everyday living, all situated on a desirable cul-de-sac lot. Riverview Landing offers trails, a fire pit, and convenient access to schools, beaches, parks, dining, and more, creating a peaceful setting with everyday convenience. Contact the sales counselor to schedule your private appointment and learn about current incentives.

212 Kwanzan Court, South Chesapeake

415 Prince Phillip Court, South Chesapeake
$409,000
3 Beds ⋅ 2.1 Baths ⋅ 10654072 MLS
Welcome to this spacious 3-bedroom, 2.5-bath split-level condo in a great Chesapeake location near Oak Grove Park, the hospital, shopping, and interstate access. The mid-level foyer leads to the lower level, featuring a comfortable sitting room with a fireplace, access to the back deck and fenced backyard, a utility closet, two bedrooms with large closets, full hall bathroom, and access to the attached 2-car garage with a convenient garage door opener. Upstairs, the updated kitchen offers stainless steel appliances, a pantry, bar, and breakfast area with bench seating, along with a fireplace and built-in storage. The upper-level living room provides additional space for relaxing or entertaining. The spacious primary suite features a walk-in closet and ensuite bathroom with a granite vanity, built-in makeup table, jetted tub, separate shower, and water closet.

415 Prince Phillip Court, South Chesapeake

913 Brenner Road, South Chesapeake
$625,000
4 Beds ⋅ 2.1 Baths ⋅ 10653790 MLS
Gorgeous and nearly new, this 4 BR 2.5 Bath bath Single-Family Home~(the Becker model) offers the community’s most spacious floor plan and is situated on an exceptionally large corner lot—the largest in the development. An inviting covered front porch welcomes you into a well-designed layout that flows beautifully from room to room, with tasteful color choices and meticulous upkeep creating a polished, move-in-ready feel throughout.The impressive Chef’s kitchen is highlighted by an oversized center island, beautiful countertops, stainless steel appliances, and soft-close cabinetry. The kitchen opens naturally to the main living area, creating a comfortable and inviting space for everyday living and entertaining.Upstairs, the spacious Primary Suite features a Huge Walk-in Closet, an additional closet, Private bath with dual sinks. 3 additional Bedrooms offer plenty of flexibility for family, guests, or a home office.Fully fenced yard & 2-car garage provides plenty of parking & storage!

913 Brenner Road, South Chesapeake

1741 Taft Road, South Chesapeake
$999,999
4 Beds ⋅ 2.1 Baths ⋅ 10653479 MLS
Three wooded acres. A saltwater pool. Five garage bays. Room for the boat, RV and workshop. And no HOA. 1741 Taft Road offers a combination that’s increasingly hard to find in Southern Chesapeake. The approx. 3,700-sq.-ft. home features 4 bedrooms, 2.5 baths and a welcoming wraparound porch. Inside, the kitchen is equipped with matte white Café appliances including a gas range, while the spacious living room centers around a wood-burning fireplace. Upstairs are 4 generously sized bedrooms, including a primary suite with 2 walk-in closets. A finished third floor adds 2 large bonus rooms, creating flexible space for a nursery, home office, gym, studio or private retreat. Outside, an approx. 32,000-gallon saltwater pool and composite deck anchor the backyard, with major pool components updated in 2025–26. A heated 2-car attached garage is joined by a 3-bay detached garage/workshop with propane heat plus mini-split heating and cooling. Covered paved storage accommodates a boat, camper or RV, with a pole barn and additional storage shed adding even more versatility. The acreage continues beyond the rear gate into the woods, where walking trails extend the ways to enjoy the property. Extensive paved parking and a private setting complete a property that offers breathing room without giving up convenient access to Chesapeake.

1741 Taft Road, South Chesapeake

613 Mcrowland Way, South Chesapeake
$675,000
3 Beds ⋅ 3.1 Baths ⋅ 10653795 MLS
Welcome to this exceptional all brick home offering luxury, comfort, and an incredibly versatile floor plan. Featuring a 3-car garage and 3 spacious primary bedrooms, each with its own en-suite bathroom. This home is great for multigenerational living or guests who desire private retreats. Inside you will find all new LVP flooring and fresh paint throughout, creating a modern feel. The impressive living room showcases soaring ceilings, abundant natural light, and a gas fireplace, creating a warm & inviting space for relaxing and entertaining. The gourmet kitchen is truly a chef's dream with custom cabinets, granite counters, a commercial grade Cafe' gas range & Cafe' Refrigerator, a microwave drawer, dishwasher and a mini refrigerator. Step outside through brand-new sliding glass doors to a raised patio and gas firepit. Great place to enjoy your morning coffee. Additional upgrades include new dual zone AC systems and a new tankless HWH. Come check out this remarkable home.

613 Mcrowland Way, South Chesapeake

1115 Killington Arch, South Chesapeake
$335,000
3 Beds ⋅ 2.1 Baths ⋅ 10653708 MLS
End-unit townhouse in Greenbrier with a peaceful pond view right in your backyard-no neighbors behind you! This home has 3 bedrooms, 2.5 baths, plus a versatile loft that works as an office, 4th bedroom, or hangout space. The kitchen features butcher block countertops & stainless steel appliances. The primary bedroom is generously sized with plenty of room to spread out. Being an end unit means extra privacy, more natural light, and fewer shared walls than a typical interior unit. Outside, it's quiet and low-key with lakes and a playground to enjoy. Located in the heart of Greenbrier East with quick access to major highways, you are just minutes away from everything Hampton Roads has to offer, including military bases, shopping, dining, beaches, and parks.

1115 Killington Arch, South Chesapeake

316 Janes Way, South Chesapeake
$624,900
4 Beds ⋅ 2.1 Baths ⋅ 10653639 MLS
Welcome home to this spacious, beautiful 4-bedroom, 2.5-bath home in sought-after Peyton Estates, offering nearly 2,800 square feet of comfortable living space on a generously sized lot. Inside, you’ll find plenty of room to spread out, including inviting living spaces and a cozy fireplace. A whole-house water filtration system adds an extra level of everyday comfort and convenience. The attached garage provides practical storage and parking, while the rear deck is a great place to relax, entertain, or enjoy the backyard. Tucked into an established Chesapeake neighborhood with convenient access to Greenbrier shopping, dining, interstates, and more, this home offers the space, location, and flexibility today’s buyers are looking for. Come see all it has to offer!

316 Janes Way, South Chesapeake

1052 Stockleybridge Drive, South Chesapeake
$725,000
5 Beds ⋅ 3 Baths ⋅ 10651967 MLS
Gorgeous 2 story Home situated on a private and lushly landscaped lot in the Etheridge Lakes neighborhood in Southern Chesapeake. Step into the elegant 2 story foyer and be amazed by the beautiful details throughout this spacious home that has been well maintained and lovingly cared for by the original owners. The vaulted Family Room opens to the large and updated Eat in Kitchen and both offer perfect views of the privacy fenced backyard oasis boasting a stunning and resort style saltwater pool with waterfall and stamped concrete surround, deck, storage shed, and outdoor shower. Additional Details: 1st floor Bedroom and full bath, Primary Suite with walk in closet and updated full bath, Formal Dining Room, new LVP flooring on 1st floor, nice sized bedrooms with ceiling fans, dual staircases, FROG is 5th bedroom, 2nd floor Laundry Room, freshly painted interior, newer carpeting, zoned HVAC, well/sprinkler system, 2 car sideload garage, gutter system, and more! Attends Hickory schools.

1052 Stockleybridge Drive, South Chesapeake

1104 Copper Stone Circle Circle, South Chesapeake
$599,000
4 Beds ⋅ 3 Baths ⋅ 10652961 MLS
WATERFRONT LIVING IN SOUGHT-AFTER HUNNINGDON LAKES! THIS BEAUTIFULLY MAINTAINED RANCH OFFERS 4 BEDROOMS, 3 FULL BATHS, FORMAL LIVING AND DINING ROOMS, A SPACIOUS FAMILY ROOM, 2 FIREPLACES, CATHEDRAL CEILINGS, AND 3 SKYLIGHTS THAT FILL THE HOME WITH NATURAL LIGHT. THE UPDATED INTERIOR FEATURES NEW FLOORING, REPLACEMENT WINDOWS, CUSTOM MOSAIC-STYLE KITCHEN CABINET DOORS, AND AN ENCAPSULATED CRAWL SPACE. THE FIRST FLOOR PRIMARY SUITE PROVIDE COMFORT AND CONVENIENCE. ENJOY YEAR-ROUND COMFORT, WITH 4 SEPARATE HVAC ZONES. STEP OUTSIDE TO YOUR PRIVATE LAKESIDE RETREAT WITH A LARGE DECK, PATIO, TRANQUIL 2-TIER WATERFALL KOI POND WITH KOI FISH, AND PEACEFUL WATER VIEWS. YOU CAN EVEN FISH FROM YOUR OWN YARD! A BRAND-NEW EMBANKMENT OFFERS LASTING SHORELINE PROTECTION. ADDITIONAL FEATURES INCLUDE 2 STORAGE SHEDS AND A TRANSFERABLE TERMINIX WARRANTY. PERFECT HOME TO LIVE, ENTERTAIN, UNWIND, AND ENJOY THE WATERFRONT LIFESTYLE RIGHT FROM YOUR BACKYARD!

1104 Copper Stone Circle Circle, South Chesapeake

311 Lancing Way, South Chesapeake
$619,000
4 Beds ⋅ 2.1 Baths ⋅ 10652797 MLS
Welcome to 311 Lancing Way! This beautiful 4-bedroom, 2.5 bath home in Chesapeake's desirable Grassfield area features a backyard oasis with a large, 33,000-gallon lagoon-style saltwater pool, 8-ft deep end, variable-speed pump, water feature, plumbing for a future waterslide/waterfall, and a buried pool drain line with pump-controlled discharge to the street. The pool is surrounded by a beautiful stamped concrete, complemented by a spacious screened porch with dual variable-speed fans, a poolside bar shed, and a garden shed with front and rear access. Inside, enjoy programmable dual-zone A/C with independently controlled thermostats and an automatic generator transfer switch. Parking for 4 cars, including an oversized 2-car garage, PLUS additional concrete parking for a boat or 2 more vehicles! No HOA fees! Conveniently located near Grassfield schools, shopping, dining, parks, major interstates, and military installations throughout Hampton Roads. Schedule your private showing today!

311 Lancing Way, South Chesapeake

1808 Ashlar Lane, South Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10652753 MLS
This is the kind of home that makes you want to unpack and stay awhile! Conveniently located for access to major Hampton Roads military installations, commuter routes, shopping, and dining, this beautifully maintained property in the highly sought Fieldstone neighborhood of Chesapeake offers 2,559 sq ft of living space, 4 bedrooms, and 2.5 baths. Brand new LVP flooring on the main level and fresh carpet upstairs create an inviting, move-in-ready feel. The open kitchen features granite countertops, abundant cabinetry, and pantry storage, flowing seamlessly into the living and dining areas with a cozy gas fireplace. A dedicated first-floor office adds exceptional flexibility for remote work, study, or hobbies. Upstairs, spacious bedrooms include a generous primary suite with a private bath and walk-in closet. Outside, enjoy a fully fenced backyard and patio, wonderful for outdoor relaxation and summer gatherings. Some photos were virtually staged using AI.

1808 Ashlar Lane, South Chesapeake

2052 Charwood Drive, South Chesapeake
$720,760
4 Beds ⋅ 3.1 Baths ⋅ 10652698 MLS
Beautiful lot backing to mature tree line. Experience the perfect blend of comfort and functionality in this versatile ranch home. The heart of the residence features an expansive open-concept living area, overlooking the kitchen with oversized island. Retreat to the spacious owner’s suite, a private sanctuary complete with a generous walk-in closet & a spa-like ensuite featuring a soaking tub & separate walk-in shower. Two additional bedrooms offer flexibility for guests or a home office. A large finished room over garage adds a 4th bedroom & full bath, included in list price, plus attic storage. Seller to pay up to $10,000 in closing cost assistance when using preferred lender, see agent for details. Buyer must register agent on or before first visit or first communication w/ listing agent & Agent must accompany Buyer on 1st visit, see Listing agent for details. Photos & Video are of previously built homes, finishes vary.

2052 Charwood Drive, South Chesapeake

1836 Bancroft Road, South Chesapeake
$730,000
3 Beds ⋅ 2 Baths ⋅ 10652410 MLS
Welcome to 1836 Bancroft! Immaculate, barely lived-in, and loaded with upgrades, this home truly feels brand new. Thoughtful improvements throughout make it as functional as it is beautiful. The open and inviting interior features ceiling fans in every room, including remote-controlled fans in the primary bedroom and living room, plus a spacious flex room offering endless possibilities as a home office, playroom, media room, or potential 4th bedroom. The home is exceptionally well-equipped for modern living, with Ethernet connections in every room and a central Ethernet relay in the coat closet, upgraded HDMI and cable connections in the living room, and prewiring for an electric vehicle. Smart-home conveniences continue with a Kwikset electronic lock, Wi-Fi connected refrigerator and dishwasher, and a Wi-Fi capable all-in-one washer/dryer. The kitchen features exterior-vented cooking ventilation, while both bathrooms have grab bars and walk-in showers—including the second full bath. A tankless water heater adds efficiency and convenience. Endless natural light, no short in thanks to the LARGE oversized sliding door installed off of the living room. Outside, enjoy a very spacious screened-in back porch perfect for relaxing or entertaining, a rear gas connection ready for your outdoor cooking setup, and an installed sprinkler system to help keep the yard looking its best. Meticulously maintained and thoughtfully upgraded from top to bottom, 1836 Bancroft offers the rare opportunity to enjoy the feel of a brand-new home without waiting for new construction. Simply move in and enjoy!

1836 Bancroft Road, South Chesapeake

905 Washington Drive, South Chesapeake
$725,000
5 Beds ⋅ 2.1 Baths ⋅ 10652400 MLS
Welcome to this spacious 5-bedroom home set on nearly half an acre in the Grassfield school district! Designed for comfortable everyday living and effortless entertaining, the light-filled layout features soaring ceilings and generous living spaces. Kitchen showcases granite countertops, abundant cabinetry, and stainless steel appliances, opening naturally to the main living areas. A first-floor bedroom offers flexibility for guests, a home office, or playroom. Upstairs, the expansive primary suite features a sitting area with fireplace, oversized walk-in closet, dual vanities, soaking tub, and tiled walk-in shower. Outside, enjoy a large deck, hot tub, and fully fenced backyard with plenty of room to gather, play, and unwind. An above-ground pool is currently in place for buyers who would like it, with removal also an option. Oversized two-car garage, ample driveway parking, and convenient access to shopping, dining, and major roadways complete this exceptional Chesapeake home.

905 Washington Drive, South 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

1441 Whittamore Road, South Chesapeake
$464,900
5 Beds ⋅ 2 Baths ⋅ 10650780 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

1509 Waitsel Drive Unit 206, South Chesapeake
$345,000
2 Beds ⋅ 2 Baths ⋅ 10650907 MLS
Welcome home to this beautiful, like-new condo in the heart of Chesapeake! Built just 2 years ago, this home offers modern finishes, an open layout, and low-maintenance living.The open-concept floor plan connects the kitchen, dining, and living areas, creating a great space for everyday living or entertaining. The kitchen features quartz countertops, stainless steel appliances, upgraded cabinetry, and a large island with plenty of room for seating. LVP flooring, updated lighting, and plenty of natural light give the home a bright, welcoming feel throughout.The spacious primary suite offers a private retreat with a beautifully finished ensuite bath and generous closet space. Conveniently located near shopping, dining, and major interstates, you’ll have easy access to everything Chesapeake and Hampton Roads have to offer.Move-in ready, only 2 years old, and beautifully maintained—this is one you’ll want to see!

1509 Waitsel Drive Unit 206, South Chesapeake

2037 Charwood Drive, South Chesapeake
$703,705
4 Beds ⋅ 3.1 Baths ⋅ 10652119 MLS
Experience the perfect blend of comfort and functionality in this versatile ranch home. The heart of the residence features an expansive open-concept living area, overlooking the kitchen with oversized island. Retreat to the spacious owner’s suite, a private sanctuary complete with a generous walk-in closet & a spa-like ensuite featuring a soaking tub & separate walk-in shower. Two additional bedrooms offer flexibility for guests or a home office. A large finished room over garage adds a 4th bedroom & full bath, included in list price, plus attic storage. Seller to pay up to $10,000 in closing cost assistance when using preferred lender, see agent for details. Estimated March 2027 closing. Buyer must register agent on or before first visit or first communication w/ listing agent & Agent must accompany Buyer on 1st visit, see Listing agent for details. Photos & Video are of previously built homes, finishes vary.

2037 Charwood Drive, South Chesapeake

505 Sandy Hill Way, South Chesapeake
$575,000
4 Beds ⋅ 2.1 Baths ⋅ 10652101 MLS
Perfectly situated in the heart of Great Bridge, this spacious 4-bedroom, 2.5-bath home offers nearly 2500 square feet in the established Sandy Hill neighborhood with no HOA. Enjoy the convenience of being just minutes from shopping, dining, parks, and everyday essentials while benefiting from sought-after Great Bridge schools. Inside, you'll find generous living spaces, brand-new carpet, and a room over the garage that can be a bedroom or a hang out space. Outside, the fully fenced backyard is ready for entertaining with an in-ground pool featuring a brand-new liner, an expansive paver patio, outdoor bar area, and storage shed. Offering space, flexibility, and recent updates in one of Great Bridge's most desirable neighborhoods, this home is ready for its next owners.

505 Sandy Hill Way, South Chesapeake

568 Waters Road, South Chesapeake
$619,000
6 Beds ⋅ 2.1 Baths ⋅ 10652034 MLS
Motivated seller! This home offers an assumable FHA loan at 2.75% for a qualified buyer, and the seller is willing to contribute toward closing costs with an acceptable offer. Located in Chesapeake’s sought-after Grassfield school district, this freshly painted, move-in ready home offers space, flexibility, and room to grow. The open floor plan centers around a spacious kitchen with generous cabinet and counter space, pantry storage, and an easy connection to the main living areas. With multiple finished areas across three levels, the layout works well for multigenerational living, long-term guests, remote work, hobbies, a media room, playroom, or additional bedrooms. The third floor was expanded in 2021 to include two finished rooms, giving buyers even more space. Outside, the large fully fenced backyard and spacious deck are ready for cookouts, pets, play, relaxing evenings, and weekend gatherings. An expanded extra-wide driveway and EV charger add everyday convenience.

568 Waters Road, South Chesapeake

1412 Sherbrooke Road, South Chesapeake
$499,900
4 Beds ⋅ 2.1 Baths ⋅ 10652040 MLS
Welcome to your dream Craftsman-style 4 bdrm 2 1/2 bath home w/a 2 car side loading garage nestled in Chesapeake. This meticulously crafted residence offers a perfect blend of modern convenience & classic charm promising a lifestyle of comfort & sophistication. The heart of the home lies in the gourmet kitchen adorned w/luxurious granite countertops & equipped with stainless steel appliances. Whether you're whipping up a culinary masterpiece or enjoying a casual meal at the breakfast bar, this culinary haven is sure to inspire your inner chef. As you venture outdoors, discover & enjoy your own oasis in the backyard waiting for your personal touch. You will enjoy easy access to local amenities, schools & major thoroughfares, ensuring that every convenience is w/in reach. Projected completion is December 2026. LVP flooring will be installed throughout the 1st floor. Photos from previous build. Make your appt today to see a previously built home.

1412 Sherbrooke Road, 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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