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$1,300,000
4 Beds ⋅ 2.1 Baths ⋅ 10654856 MLS
Elegant custom details and room to live the life you’ve imagined! Sweeping down a long, paved driveway, this beautiful 4-bedroom home pairs comfortable country living with a thoughtfully arranged estate. Set on over 12 pristine acres in Chesapeake, zoned for Hickory schools, this property is a rare rural sanctuary. A wraparound porch welcomes you inside to 9' ceilings, 8' doors, and reclaimed knotty pine floors. The living room features a stone fireplace, opening to a bright kitchen with soft-close cabinets, Samsung Bespoke appliances, and butler’s pantry. Outside, enjoy a saltwater pool, fire pit, and private porches within a completely fenced in yard. The farm boasts a 6-stall barn with wash station, hot water, and mini-split, plus 5 watered pastures, 3 run-ins, and a 50x42 Morton building. An additional 1.5 acres offers potential for a riding arena or agriculture gardening, while a chicken coop, fruit trees, and berries complete the setting. Enjoy southern Chesapeake's rural character, with conveniences and Route 168 nearby.

1713 Sanderson Road, South Chesapeake

$585,000
3 Beds ⋅ 2 Baths ⋅ 10654878 MLS
Welcome home to this well-maintained brick ranch situated on approximately 1.5 acres in North Landing Farms. Recently appraised, this 3-bedroom, 2-bath home offers 1,773 sq. ft. of single-level living with a fireplace, covered front porch and large rear deck. A climate-controlled detached 2-car garage/workshop with upstairs workspace/storage provides excellent space for vehicles, hobbies and projects. Additional outdoor features include a barn, storage shed, raised garden beds, chicken run and grape arbor. HVAC, water heater and appliances are approximately 7 years old. No HOA! Zoned for Hickory Middle and Hickory High School. Enjoy plenty of space, privacy and versatility in this unique Chesapeake property. Schedule your private showing today!

552 Saddlehorn Drive, South Chesapeake

$300,000
3 Beds ⋅ 2.1 Baths ⋅ 10654893 MLS
Largest floor plan in the neighborhood! Lovingly maintained and thoughtfully updated, this spacious brick townhome is tucked away on a quiet cul-de-sac in the heart of Chesapeake. Enjoy a private, fully fenced backyard with no homes directly behind you and no HOA. Inside, you’ll find fresh paint, new carpet and flooring, updated bathrooms, new fixtures and hardware, and gleaming hardwood floors. The brand-new kitchen features granite countertops, stainless-steel appliances, a gas range, and full-size refrigerator. A wood-burning fireplace adds warmth and character, while abundant natural light fills the home. Plenty of indoor and outdoor storage provides added convenience. With a low-maintenance brick exterior, spacious floor plan, thoughtful updates, and a private backyard, this home is truly move-in ready. Pride of ownership is evident throughout—come see it today!

302 Fairfax Terrace, South Chesapeake

$465,000
4 Beds ⋅ 2 Baths ⋅ 10654846 MLS
Welcome home to 708 Colony Drive in Chesapeake! This beautifully updated 4-bedroom, 2-bath ranch offers the ease of primarily one-story living with an additional level above the garage featuring a true fourth bedroom with a closet. Inside, the open and inviting layout flows from the spacious living area into the dining room and beautifully updated kitchen, featuring quartz countertops, brass fixtures, a large sink, all-new stainless steel appliances, and modern finishes. Thoughtful updates continue throughout the home, including two beautifully remodeled bathrooms with tile finishes that give the space a fresh, elevated feel. The home is move-in ready while still offering the perfect opportunity to add your own personal touches. Outside, enjoy a fully fenced backyard with a deck, ideal for relaxing, entertaining, or pets. An attached one-car garage, two-car driveway, and additional parking space complete this beautiful Chesapeake home.

708 Colony Drive, South Chesapeake

$410,000
3 Beds ⋅ 2.1 Baths ⋅ 10654442 MLS
GREAT BRIDGE + HUGE BACKYARD + NO HOA! This beautifully maintained 3 bedroom, 2.5 bath home offers the space, features and location you've been looking for! Step inside to a bright, inviting interior filled with natural light and featuring updated flooring, granite countertops and a wood-burning fireplace, just right for cozy evenings. Upstairs, you'll find a spacious primary suite, along with two additional bedrooms. Step outside and discover one of this homes' standout features - a HUGE, fully fenced backyard with plenty of room to entertain, play, garden or simply relax on the patio. The 2-car garage provides additional parking and storage. Conveniently located near shopping, dining, parks and major roadways. Well maintained, move-in ready and NO HOA! Solar panels are paid for! Schedule your showing and come see what makes this Great Bridge home a must-see!

828 Helmsdale Way, South Chesapeake

$399,900
4 Beds ⋅ 2.1 Baths ⋅ 10654385 MLS
Welcome to your next great opportunity! This spacious 1,917 sq ft ranch home offers 4 bedrooms and 2.5 bathrooms with a flexible floor plan designed for effortless daily living. The functional layout includes a large Finished Room Over Garage (FROG) as the 4th bedroom— could also be used as an office, media room, or flex space. Inside flows seamlessly to the back deck, overlooking an expansive 0.389-acre lot with abundant outdoor space and a large storage shed. Complete with a 1-car attached garage, this property offers incredible potential! Bring your vision—with a touch of sweat equity and minor cosmetics, this solid home will truly shine and build instant equity. Excellent location with convenient access to major interstates, regional bases, dining, shopping, and entertainment. Call today to schedule your private showing!

620 Emerald Court, South Chesapeake

$425,000
4 Beds ⋅ 2.1 Baths ⋅ 10654335 MLS
Discover timeless charm in this beautiful, traditional home located in the heart of Chesapeake. Featuring 4 bedrooms, 2.5 bathrooms, and a spacious two-story layout, this home includes a bedroom with its own en suite bath, making it great for guests or added privacy. Gather around the cozy fireplace on cool evenings, or enjoy casual meals in the bright breakfast area. Step outside to a fully fenced backyard, great for entertaining, pets, or relaxing outdoors. Recent upgrades, including new siding and roof (2021) and a remodeled primary bathroom (2025), enhance both the home's beauty and value. An attached garage and attic complete this exceptional property. Don't miss your opportunity to make this Chesapeake gem your own!

744 Helmsdale Way, South Chesapeake

$879,900
4 Beds ⋅ 2.1 Baths ⋅ 10654253 MLS
The perfect farmhouse that’s a mix of privacy and closeness to local amenities. Sitting on approx 3 acres in Albemarle Farms, this home offers the updates you've been looking for. Step inside to a bright, welcoming interior with engineered hardwood floors, fresh paint throughout, new trim, and a beautifully updated kitchen. Completed in 2025, the kitchen features all-new cabinetry, quartz countertops, a large island, white stone backsplash, new appliances, and a new sink and faucet. Just beyond, the great room is centered around a new stone fireplace and mantle, while the 4-season room offers a flexible space to relax, work, or enjoy views of the property. Upstairs, the primary suite features a soaking tub and walk-in shower, with two additional bedrooms and bonus space offering plenty of flexibility. Major improvements include new heating and cooling units, new ductwork upstairs and downstairs, a new tankless water heater, and new downstairs subfloor. Outside is where this property really shines, with a saltwater in-ground pool, expansive deck, covered rear porch, circular driveway, and plenty of room to enjoy the wooded setting. An oversized garage with a finished room above adds even more usable space. Located in the Hickory school district with no HOA, this is a home with room to settle in, spread out, and enjoy both indoors and out. Incentives may be available through preferred partners. Contact listing agent for details and eligibility.

609 Fairfield Drive, South Chesapeake

$474,900
4 Beds ⋅ 2 Baths ⋅ 10654137 MLS
Charming ranch with large backyard and pool! Enjoy the welcoming front porch before heading inside to the thoughtfully updated interior, where fresh paint and beautiful new LVP flooring create a bright, inviting atmosphere. New carpet in the room above the garage adds comfort and versatility to the home's flexible living space. Designed for both everyday living and effortless entertaining, the home features a living room, dining room, and a cozy family room accented by wood beams and a fireplace. At the heart of the home, the eat-in kitchen offers all new sleek cabinetry, granite countertops, and stainless steel appliances. Four spacious bedrooms provide comfortable accommodations, while both full bathrooms have been refreshed with stylish new vanities. Outside, you're sure to enjoy the fully fenced backyard featuring a spacious deck overlooking the swimming pool creating an inviting setting for relaxing, entertaining, or enjoying warm summer days. Two storage sheds provide additional room for lawn equipment, tools, or hobbies, while the attached garage adds everyday convenience and extra storage.

403 Caravelle Court N, 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

$635,000
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

$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

$1,100,000
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

$485,000
3 Beds ⋅ 2.1 Baths ⋅ 10653649 MLS
Welcome to 224 Northview Drive in Chesapeake, VA where pride of ownership is evident from the moment you arrive. Thoughtful updates, beautifully maintained spaces, and inviting indoor and outdoor areas make this home truly stand out. Inside, enjoy hardwood floors throughout the main living areas and bedrooms, along with a renovated kitchen featuring LVP flooring, Corian countertops, and stainless steel appliances. Both the main bathroom and en suite bathroom have been fully renovated with natural stone flooring, custom tile details, updated vanities, and premium finishes. Bedroom closets feature IKEA BOAXEL organization systems, and updated ceiling fans throughout add to the refreshed feel of the home. Outside, the upgrades continue with a custom two-level composite deck with low-voltage lighting, a large pea gravel patio and walkways, Wellis London spa, gazebo with swing, powered 10' x 14' shed with loft and workbench, privacy fencing, and a separate gated dog or play area. Mature trees, Japanese maples, azaleas, rhododendrons, and other established landscaping create a peaceful, wooded setting with plenty of character. The front exterior features a custom brick mailbox, brick hardscaping, fresh mulch, accent landscaping, and a double-width driveway with parking for up to five vehicles. Located in the Great Bridge school district and just minutes from shopping, restaurants, and everyday conveniences, this home offers a great blend of privacy and accessibility. If you’ve been searching for a well maintained home in Chesapeake, VA with upgrades throughout, hardwood floors, renovated kitchen and bathrooms, natural stone bathroom flooring, a large composite deck, hot tub, powered shed, privacy fenced backyard, mature landscaping, and generous parking, 224 Northview Drive is one to see.

224 Northview Drive, South Chesapeake

$450,000
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

$775,000
5 Beds ⋅ 2.1 Baths ⋅ 10653033 MLS
Welcome to 3708 Riverwood Crescent! Situated on approx. 3 acres in sought after Chesapeake 23322, this nearly 3,000 sq. ft. home offers space, privacy & extensive updates! Enjoy a private backyard retreat with pool, screened porch & updated deck. Inside features a remodeled kitchen with quartz countertops, mostly stainless steel appliances, soft-close cabinetry, recessed lighting, hardwood & luxury vinyl plank flooring, plus new carpet upstairs, and solar hallway lighting. Updated baths include new countertops, toilets, fixtures, ceramic tile, tub/shower & an enlarged porcelain-tiled primary shower. Major improvements include dual-zone HVAC (2019/2021), 2024 water heater, water softener, encapsulated crawl space with pump & dehumidifier, replaced exterior/garage doors, vinyl windows & 2011 roof with 50-yr warranty. Shed and lawn tractor conveys! A rare combination of acreage, updates, pool & location; come see it!

3708 Riverwood Crescent, South Chesapeake

$265,000
2 Beds ⋅ 2 Baths ⋅ 10653023 MLS
Welcome to this spacious and comfortable condo located in the desirable Riverwalk neighborhood. This home offers plenty of room to spread out and entertain. With both bedrooms connected to their own en suites you can enjoy both privacy and convenience. Upstairs includes a versatile loft area leading into the primary bedroom; providing additional space for a home office, reading area, or flex space. With new upgrades like the Heat Pump (2021) and the Roof (2025, by the association) you can have the peace of mind that you're in a good space. Outside, a cute private patio provides a pleasant spot to relax and enjoy some fresh air. The condo association gives low-maintenance living by covering the siding and roof, water and sewage, trash pickup, while maintaining the pool, clubhouse, and public spaces! With large living areas, a functional multi-level floor plan, and important updates, this condo is ready for its next owner! Setup a tour and make it you!

700 Nottoway River Court Unit D, South Chesapeake

$998,895
5 Beds ⋅ 3.1 Baths ⋅ 10652907 MLS
Experience luxury living in this one-of-a-kind Chesapeake retreat, nestled on a 3-acre lot in the Grassfield School District. This custom-built home blends modern comfort with timeless charm, offering an open-concept first floor design for today's lifestyle. The spacious family room flows seamlessly into the remodeled 2024 kitchen, with direct access to the back deck for everyday relaxation or entertaining guests. Choose between two generous primary suites. First floor primary suite features a gas fireplace, dual closets, and a sitting/office area. Second floor primary suite privately located above 3-car garage, offering separation from the additional upstairs bedrooms. Enjoy abundant space for hobbies and storage with two powered sheds, plus peace of mind from the new encapsulated crawl space with vapor barrier. Major upgrades, including the roof, HVAC, and kitchen in 2024, ensures comfort and efficiency for years to come. This exceptional property delivers a rare combination of privacy, space, and freedom with no HOA restrictions, making it a true Chesapeake gem. **Bookshelves do not Convey**

1910 Hallmark 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

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.