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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

604 Colonel Byrd Street, South Chesapeake
$540,000
4 Beds ⋅ 3.1 Baths ⋅ 10653623 MLS
Gorgeous planned community with neighborhood clubhouse, swimming pool, fitness center and recreation spaces. At the center of the home, the chef-inspired kitchen features an oversized prep island, stone countertops, stainless steel appliances, premium soft-close cabinetry, and a walk-in pantry. The primary suite is conveniently situated on the main level, complete with a generous walk-in closet and en-suite bath. Upstairs, you will find two sizable secondary bedrooms, a full bath, and an open loft enhanced with custom built-ins. A private fourth bedroom or versatile bonus suite sits above the garage, featuring its own dedicated full bath and integrated shelving—ideal for guests, a home office, or a media room. Outdoor living is a standout feature, highlighted by a screened porch, an open patio, and a wood-burning firepit overlooking peaceful water views within a fully fenced backyard.

604 Colonel Byrd Street, South Chesapeake

1513 Wingfield Avenue, Central Chesapeake
$324,900
3 Beds ⋅ 2 Baths ⋅ 10653971 MLS
Welcome to 1513 Wingfield Avenue! This spacious ranch-style home in Indian River offers three bedrooms, two full bathrooms, and an additional room off the primary bedroom—great for a home office, sitting room, dressing room, or private retreat. Laminate floors flow throughout the home, while the updated kitchen provides a fresh and inviting space for everyday living. Outside, enjoy a large fenced-in yard with a storage shed, an oversized driveway, and a full garage offering plenty of parking and storage. Conveniently located near the interstate, shopping, dining, and schools, this home brings together space, flexibility, and a convenient location. Schedule your showing today! Avg electric bill for the past 6 months - $9.33 p/mo!

1513 Wingfield Avenue, Central 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

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

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

5235 Lombard Street, West Chesapeake
$390,000
3 Beds ⋅ 2.1 Baths ⋅ 10653106 MLS
Stunning modern, low-maintenance living in Western Branch's sought-after Jolliff Landing! Built in 2018, this beautifully maintained ~1,894 sq ft townhome offers the perfect blend of style and convenience. Highlights: Open-Concept Living: Bright, airy main level seamlessly connecting living and dining spaces. Chefs Kitchen: Features granite countertops, a center island, stainless steel appliances, and ample cabinet storage. Primary Suite: Spacious retreat complete with a large walk-in closet and private ensuite bath. Upstairs Layout: Two additional versatile bedrooms, a full guest bath, and convenient 2nd-floor laundry. Exterior & Parking: Attached 1-car garage, private driveway, and rear patio backing to green space. Prime Location: Minutes to I-664, Chesapeake Square, dining, top schools, and military bases. Move-in ready and easy to showschedule your private tour today!

5235 Lombard Street, West 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

4207 Coffman Boulevard, West Chesapeake
$399,000
4 Beds ⋅ 2 Baths ⋅ 10653672 MLS
Well-maintained home, on over half an acre lot in desirable Chadswyck Terrace. Inviting layout is ideal for everyday living & entertaining, with a spacious living room flowing into the dining area & kitchen. Wood-burning fireplace adds warmth & character. The kitchen boasts stainless steel appliances, abundant counter space, & an adjoining utility room that can also serve as a convenient mudroom. Private primary suite features an ensuite bath, creating a comfortable retreat. Above the garage, a versatile bonus room can serve as a bedroom, office, playroom, or guest space. Enjoy the expansive backyard & generously sized deck, perfect for relaxing, grilling, or entertaining. Property extends beyond the fenced area, offering room to expand the enclosure. Updates include a new roof in 2020 & HVAC system in 2018. Close to shopping, dining, the mall, & interstate access. Solar panels will be paid off at closing; the electric bill is $9/mo & VA Assumable loan option with a 2.5% interest rate!

4207 Coffman Boulevard, West Chesapeake

1221 Rosebud Lane, South Chesapeake
$524,900
4 Beds ⋅ 2.1 Baths ⋅ 10653645 MLS
Well-maintained 4-bedroom home featuring an open floor plan and beautiful hardwood flooring throughout the main living areas. The spacious kitchen offers 42-inch cabinetry, granite countertops, a center island, stainless steel appliances, and plenty of workspace for everyday living and entertaining. Generously sized bedrooms include a spacious primary suite with a private bath and jetted tub. The open layout provides a comfortable flow between the kitchen and living spaces. Outside, enjoy a large fenced backyard with plenty of room for outdoor entertaining, recreation, or relaxing. Located in the Hickory school district and built in 2011, this home offers a great combination of space, style, and functionality.

1221 Rosebud Lane, 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

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

916 Redstart Avenue, Central Chesapeake
$360,000
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

2213 Wilmington Avenue, West Chesapeake
$544,900
4 Beds ⋅ 3 Baths ⋅ 10653325 MLS
A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch style living with 4 bedrooms including a large finished room over the garage. From the front porch to the Family Room also open to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your door step in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

2213 Wilmington Avenue, West Chesapeake

3705 Davis Avenue, Central Chesapeake
$499,900
5 Beds ⋅ 3 Baths ⋅ 10653261 MLS
BRAND-NEW CONSTRUCTION IN AN ESTABLISHED CHESAPEAKE NEIGHBORHOOD! Welcome to 3705 Davis Avenue, where modern design and the ease of new construction come together in an established community. Offering approximately 2,550 square feet, this spacious home features 5 bedrooms, 3 full baths, and a thoughtfully designed open floor plan with flexibility for today's lifestyle. A standout feature is the oversized first-floor bedroom with direct access to a full bath, also conveniently accessible from the hallway. This versatile space is ideal for multigenerational living, an in-law suite, overnight guests, a private home office, or anyone seeking comfortable first-floor accommodations. Davis offers the opportunity to enjoy a fresh, modern home without giving up the character and convenience of an established neighborhood.

3705 Davis Avenue, Central Chesapeake

4009 1st Street, Central Chesapeake
$375,000
4 Beds ⋅ 3 Baths ⋅ 10653176 MLS
Welcome home to this beautifully updated two-story home offering the perfect blend of comfort, style, and functionality. As you enter, you'll find a convenient first-floor bedroom and full bathroom, ideal for guests, multi-generational living, or a private home office. The heart of the home features an open-concept layout where the living room, dining area, and kitchen flow seamlessly together beneath soaring 9-foot ceilings with recessed lighting throughout, creating a bright and inviting space for everyday living and entertaining. The kitchen provides easy access to the fully fenced backyard, making outdoor gatherings a breeze. You'll also love the oversized shed/workshop, offering endless possibilities for storage, hobbies, or a dedicated workspace. Upstairs, you'll find two additional secondary bedrooms along with a spacious primary ensuite designed for comfort and privacy. Fresh paint and NEW flooring completed in 2026 give the home a modern, move-in-ready feel, while the NEWER HVAC system (2022) and NEW maintenance-free metal-wrapped roofing trim (2026) provide added peace of mind. Conveniently located near shopping, dining, schools, and major interstates, this home is ready for its next owner. Virtually staged. Schedule your private tour today!

4009 1st Street, Central Chesapeake

313 Holyoke Lane, South Chesapeake
$283,999
2 Beds ⋅ 2.1 Baths ⋅ 10653079 MLS
Turnkey Luxury in Oakbrooke Crossing – Fully Updated & Pre-Inspected!Welcome to this beautifully updated 2-bedroom, 2.5-bathroom townhome-style condo in desirable Oakbrooke Crossing! This move-in-ready home features brand-new LVP flooring, fresh neutral paint, and an updated kitchen with laminate countertops, breakfast bar, and stainless steel appliances. Upstairs, you’ll find two spacious primary suites, each with its own private en-suite bathroom great for guests, roommates, or a home office. Enjoy added peace of mind with a brand-new water heater (2024), recently serviced HVAC, and a professional pre-inspection with the report available upon request.Conveniently located in the heart of Chesapeake, just minutes from Greenbrier shopping, dining, business centers, and interstate access. The low-maintenance condo lifestyle includes ground maintenance, trash service, and community upkeep. Ready for you! Schedule your showing today!

313 Holyoke Lane, 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

700 Nottoway River Court Unit D, 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

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.