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744 Helmsdale Way, 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

609 Fairfield Drive, South Chesapeake
$849,900
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

1733 Head Of River Road, South Chesapeake
$829,900
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

1816 Sunsprite Loop, South Chesapeake
$600,000
6 Beds ⋅ 3 Baths ⋅ 10654192 MLS
It’s got space!! Use all 6 bedrooms or create the office, guest room, fitness space or playroom you've been looking for. The first floor offers a bedroom, adjacent flex room and modified curb less shower—great for guests or anyone who prefers fewer stairs. Neutral décor, 9' ceilings, hardwood floors, crown molding and a huge FROG. Spacious primary suite with hardwood floors and two walk-in closets, plus second-floor laundry. Outside, enjoy a lg, fenced backyard , detached shed, private well for lawn irrigation and attached 2-car garage. Meticulously maintained with annual HVAC, tankless water heater and crawl-space service contracts. Seller to provide termite/moisture letter. Convenient to Millville Rd. and Veterans Bridge. Annual Termite/Moisture contracts/ NO FLOOD INS. Grassfield High School has earned national recognition in US News and World Reports for VA’s Board of Education Highest Achievement Award / 2024. $5,000 Closing Cost Assistance. Original Owner.

1816 Sunsprite Loop, South Chesapeake

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

622 Ambrose Street, South Chesapeake
$625,000
5 Beds ⋅ 3 Baths ⋅ 10654148 MLS
Proposed new construction by an award-winning builder featured in past Homearama! Custom open design with a desirable 1st-floor bedroom, spacious living areas and upgraded features included. Enjoy a great yard with room to spread out and the feel of country living while still convenient to major shopping, dining, schools and everyday amenities. NO HOA fees! Anticipated delivery late 2026/early 2027. Get involved early for the opportunity to make certain selections, subject to builder schedule and allowances. One inventory home is currently available for more immediate delivery, and smaller plans may also be available. Great opportunity and value for new construction! Room to install a pool. Call listing agent for plans, pricing, specifications, allowances, construction status and available options.

622 Ambrose Street, South Chesapeake

704 Woodcott Drive, South Chesapeake
$560,000
3 Beds ⋅ 2.1 Baths ⋅ 10654136 MLS
Welcome home to 704 Woodcott Drive. This beautifully refreshed 4 bedroom 2 1/2 bath home is full natural light and lovingly updates. The bright, inviting interior features new LVP flooring, new carpet, and fresh paint throughout, giving the home a beautiful, fresh feel. The updated kitchen is great for gatherings, with quartz countertops, stainless steel appliances, and a gorgeous double sided fireplace shared with the living room. The loft can be used as a flex room, office or media room. Enjoy the barbecues on the back deck overlooking the huge backyard. Make this the perfect spot to enjoy cozy evenings or entertaining family and friends. Seller to offer buyer 2/1 rate buy down as well as a new driveway with full price offer.

704 Woodcott Drive, South Chesapeake

212 Kwanzan Court, South Chesapeake
$793,267
5 Beds ⋅ 3 Baths ⋅ 10654133 MLS
Move-In Ready Cul-de-sac Location! Discover the Bellhaven floorplan by Wetherington Homes at Riverview Landing! This beautifully designed 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. Reach out to schedule your private tour and learn about current incentives.

212 Kwanzan 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

1118 Commerce Avenue, Central Chesapeake
$379,800
4 Beds ⋅ 3 Baths ⋅ 10653792 MLS
*****Seller offering up to 6% in closing cost assistance, subject to buyer's loan program, lender approval, and allowable closing costs.***** Located in the heart of Chesapeake’s South Norfolk community, this well-maintained residence offers 4 bedrooms and 3 full bathrooms, giving you plenty of space whether you need room for guests, hobbies, or simply a place to hide from laundry you meant to fold. The home features a spacious layout with thoughtfully designed rooms throughout. The downstairs bedroom includes newly installed LVP flooring (2026) and a walk-in closet — storage, organization, or pretending you’re in a dramatic movie scene while picking out an outfit. Upstairs, you’ll find carpeted bedrooms, including a primary suite with its own walk-in closet (because one walk-in is never enough). Enjoy easy access to downtown Norfolk, major shipyards, and nearby interstates, making commutes simple and efficient. This inviting property is ready to welcome its next owner.Come see this gem and explore all it has to offer ---your future self might thank you for it!

1118 Commerce Avenue, Central Chesapeake

2949 Prince Of Wales Drive, West Chesapeake
$539,000
5 Beds ⋅ 2.1 Baths ⋅ 10653953 MLS
Welcome to this charming 5-bedroom home, perfectly situated in a wonderful, established neighborhood in Chesapeake. If you appreciate a home with character and room to grow, this is the perfect canvas for your vision. The heart of the home features a kitchen designed for those who love to cook, offering an abundance of counter and cabinet space, plus the convenience of a double oven. You’ll love spending quiet evenings by one of the two cozy fireplaces or unwinding on the beautiful, screened-in porch that overlooks a private, tree-lined backyard. With spacious bedrooms throughout, this home offers plenty of room for everyone to enjoy. Bring your personal touch and make this well-loved house your own!

2949 Prince Of Wales Drive, West Chesapeake

302 Honey Locust Way, South Chesapeake
$635,000
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, South Chesapeake

3421 Anita Circle, West Chesapeake
$547,150
4 Beds ⋅ 3.1 Baths ⋅ 10653856 MLS
Timeless qualities with some modern flare in this Solid Custom Built home by CHARLES D JOHNSON. This home offers Just over 2500 sq ft. with the perfect layout, 4 bedrooms, 3.5 baths on a .25 acre lot in the quiet, sought-after Miars Farm neighborhood. Huge, open & bright kitchen with granite countertops, built in storage bench along bay window. Island with Bar. Separate pantry. Separate formal dining room and Great room with beautiful wood floors. Laundry room on 1st level & a 2nd. Access to 2nd floor Finished Room over Garage with full bath from kitchen. Primary bedroom & bath, walk in closets with built ins. 2 additional bedrooms & another full bath offers plenty of living space options. Peaceful enjoyment on the deck with pool. Cute Shed and fully fenced back yard. 2 car garage with plenty of driveway space. No HOA.

3421 Anita Circle, West 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. Seller is offering $10K towards closing cost assistance or a rate buy down with a reasonable offer.

613 Mcrowland Way, South Chesapeake

3106 Lantern Place, West Chesapeake
$424,900
4 Beds ⋅ 2.1 Baths ⋅ 10653646 MLS
Enjoy low-maintenance living in this beautifully maintained end-unit townhome in a sought-after 55+ community. This home features a first-floor primary suite, an open-concept living area with a gas fireplace, a spacious kitchen with upgraded cabinetry, a dining room, private office, and a convenient first-floor laundry room. Step outside to the screened-in porch, where you can enjoy views of the community pool from your fenced backyard and take advantage of easy access to the clubhouse. Upstairs offers additional bedrooms, a versatile loft, abundant storage, and an unfinished fourth bedroom currently used for storage that can easily be finished to suit your needs. Community amenities include a fitness center, resort-style pool, full kitchen, fire pits, fire tables, and a dog park. Complete with an attached two-car garage, this home combines comfort, convenience, and an active lifestyle.

3106 Lantern Place, West 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

3303 Arboretum Trl, West Chesapeake
$585,000
4 Beds ⋅ 3 Baths ⋅ 10653614 MLS
Welcome to this spacious 4-bedroom, 3-bath home featuring a bright and open floor plan designed for comfortable living and entertaining. The beautiful kitchen offers abundant cabinet space, stainless steel appliances, granite countertops, and a large center island perfect for gatherings. The first floor includes a generous family room, office area, and additional living space, providing flexibility for work and relaxation. Upstairs you’ll find 4 generously sized bedrooms with ample closet space. The primary suite features both a walk-in closet and an additional closet, along with a private bath with dual vanities, tub and nice size shower. Freshly painted, new carpet and new refrigerator. Step outside to enjoy the patio and nice size yard for your entertainment and outdoor activities. Located in the desirable Western Branch area, this home provides comfort, space, and a peaceful community setting.

3303 Arboretum Trl, West Chesapeake

1530 Jolliff Road, West Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10653544 MLS
Ready Soon! Your New Home in Western Branch! Exceptional new construction on a spacious half-acre lot, thoughtfully designed for modern living and outdoor enjoyment. This open-concept floor plan features a desirable first-floor guest suite with a private bath and walk-in closet. The chef-inspired kitchen showcases granite countertops, custom cabinetry, stainless steel appliances, and designer lighting. Luxury vinyl plank flooring flows throughout the first floor and all bathrooms. Enjoy a covered front porch, two-car garage, and rear patio overlooking your private backyard, with plenty of space to add a pool and create your own outdoor oasis. Quality craftsmanship and thoughtful design come together in this highly desirable Western Branch location. Completion in Fall 2026. Don't miss the opportunity to make this exceptional new home yours!

1530 Jolliff Road, West Chesapeake

905 Bernard Lane, South Chesapeake
$525,900
4 Beds ⋅ 3.1 Baths ⋅ 10653474 MLS
$12,500 closing costs*, Low Loan Rate, No PMI! - Choose your look! - UPGRADES GALORE! Built by award-winning builder. Stunning home w/curated features uniquely designed in this home. Extensive Mohawk flooring through mid-level with Gourmet Kitchen w/Custom hood, 10' island with Quartz counters, GE Cafe 6 Burner Gas range, GE Cafe Dishwasher, and GE Cafe Microwave Drawer. 10' ceilings MAIN, 9' First & Third Floors, 2-zone HVAC w/thermostat on each floor. Primary bedroom with Walk-in CLOSET and spa ensuite Bath. Custom stair rail with 42" treads. Two bedrooms, hall bath, and laundry room complete the third flr. First floor bedroom with ENSUITE bath! Oversized 10'x19' covered porch with Trex decking, 2-car garage, Tankless Water Heater - and more! LOW $95 condo fee w/Cabana, Fire pits, Bocce ball and Professional landscape and lawn maintenance.. Ready for easy living! Legacy is waiting for you!

905 Bernard Lane, South Chesapeake

4704 Mahogany Run, West Chesapeake
$453,181
4 Beds ⋅ 3 Baths ⋅ 10653533 MLS
The final building under construction at The Retreat at Western Branch! The Lafayette floorplan delivers spacious, stylish living with an estimated March/April 2027 completion. The thoughtfully designed first-floor features a primary suite, guest bedroom or office with full bath, and an impressive island kitchen flowing seamlessly into the great room and dining area. 2-car garage and covered porch, too! Upstairs, discover an expansive loft, two additional bedrooms, a full bath, and extra storage. All in a low-maintenance 55+ condo community with resort-style amenities, including a clubhouse with fitness center and billiards, swimming pool, outdoor grilling area, dog park, community garden, and beautifully landscaped grounds. Don't miss this exciting opportunity to make the Lafayette your next home!

4704 Mahogany Run, West Chesapeake

916 Redstart Avenue, Central Chesapeake
$340,000
3 Beds ⋅ 2 Baths ⋅ 10653529 MLS
Discover the charm of this mid-century Craftsman style home. This property showcases the allure of cottage living. The front room picture window allows natural light to fill the home enhancing the natural grain of the rustic hardwood floors and the dining room's elegant French doors with glass panels. All this connects seamlessly to the spacious kitchen adorned with granite countertops and the sunken den with its magnificent stairway leading to the primary suite. This home has seen numerous upgrades providing Peace of Mind and convenience. Water Heater 2016, Garage door 2018, HVAC Gaspack 2020, Laundry Room upgrade to PVC 2021, Roof 2024 with 15 sheets of new plywood in carport ceiling. Mini split in primary 2026. The Darling backyard has a covered picnic area and works perfectly with the carport for entertaining. Detach Garage has its own electrical system and is a blank palette to be designed as the new owner desires. It is strictly as is.

916 Redstart Avenue, Central 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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