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$234,900
2 Beds ⋅ 1 Baths ⋅ 10643302 MLS

844 Wickford Drive, South Chesapeake
$239,900
2 Beds ⋅ 2 Baths ⋅ 10643303 MLS
Located in the Western Branch North area of Chesapeake, Virginia, 4332 Hillingdon Bend, Unit 206, is a second-floor condominium built in 2014. The residence offers approximately 1,367 square feet of single-level living space with an open floor plan and nine-foot ceilings. It features two bedrooms and two full bathrooms, including a primary suite equipped with dual closets. The kitchen includes stainless steel appliances and ample cabinetry, opening directly into the main living and dining areas. Additional interior features include central air conditioning, forced air heating, and dedicated washer and dryer hookups. As part of a common-interest community, the property provides one assigned parking space and access to shared amenities, such as a swimming pool, ground maintenance, and trash removal. Positioned near major highways, military bases, local shipyards, and retail options surrounding Chesapeake Square.

4332 Hillingdon Bend Unit 206, West Chesapeake
$284,000
2 Beds ⋅ 2.1 Baths ⋅ 10643295 MLS
Located in one of the most private settings in The Woodlands, this condo offers a spacious, modern layout with wooded views and no buildings directly behind. The open first floor features a bright living area, dining space, and a well-equipped kitchen with abundant counter space, breakfast bar, stainless steel appliances, and a large pantry. Sliding doors open to a fenced patio with a storage shed, creating a private outdoor retreat. Upstairs, the flexible bonus room is ideal for a home office, media room, workout space, or guest area. Both primary suites include large closets. Condo fees cover the community pool, exterior maintenance, sewer, and trash pickup. Conveniently located just 0.3 miles from Russell Memorial Library.

2806 Baldwin Drive, West Chesapeake
$524,900
3 Beds ⋅ 2.1 Baths ⋅ 10643243 MLS
Beautifully maintained 55+ condominium in the desirable Greenbrier area. Built by Stephen Alexander Homes, this elegant residence blends historically inspired architecture with timeless craftsmanship, featuring 10-foot ceilings, transom windows, custom crown moulding and trim work, and hardwood floors. Offering 3 bedrooms plus a spacious room over the garage, this home provides exceptional flexibility for guests, hobbies, or a home office. The gourmet kitchen with double ovens is designed for everyday living and entertaining. An interior private elevator provides effortless access to both levels. Additional features include an attached two car garage with overhead storage and utility sink, brand-new dual-zone HVAC, a Rinnai tankless water heater, and a freshly painted exterior. Relax on the spacious front porch or entertain on the private tiled patio with a SunSetter retractable awning. Whole-house audio and family room surround sound add comfort and ambiance throughout. Move in ready!

1016 Briars Landing Landing, South Chesapeake
$50,000
10643091 MLS
This buildable lot with existing driveway is next door to 1314 20th street in Chesapeake, and can be negotiated together, or sold separately. Seller is a licensed Virginia Realtor.

1316 20th Street, Central Chesapeake
$699,000
5 Beds ⋅ 2.1 Baths ⋅ 10642890 MLS
This property is a gardener's dream. It has a variety of flowering plants that provide blossoms throughout the growing season. Blooms are sequenced for near year round color. There are 10 field-stone edged garden beds add stunning features to the landscape. One garden bed in the back has a goldfish pond. One in the front features an unique natural stone bench. Back yard includes vegetable garden plot that faces the sun for garden fresh produce. Back yard oasis includes a hot tub and six foot privacy fence. Two patios are connected by a master-crafted pave walk-way. Oversized garden shed helps keep garage clutter free. Two lockable gates one on each side of the property. In ground sprinkler system fed by well water to keep watering cost low. Two outdoor water taps fed by the well and two additional taps fed by city water. Tank-less water heater provides endless hot water. The oversized primary bedroom includes two walk in closets. One large walk-in closet features two side cubby units for storage. The other walk in closet is medium sized with plenty of storage space. Washer and dryer are on the second floor for convenience to bedrooms.

707 River Gate Court, South Chesapeake
$499,500
4 Beds ⋅ 2 Baths ⋅ 10643133 MLS
This beautifully renovated 4-bedroom, 2-bath home featuring 2,117 sq. ft. of bright and open living space is ready for you! The updated kitchen features custom cabinetry, quartz countertops, custom tile backsplash, large island, and stainless steel appliances. Perfect for cooking and entertaining. Tastefully finished bathrooms include custom tile, updated vanities, newer toilets, flooring and fixtures. Major recent updates include newer roof, ductwork, vapor barrier. Interior updates include recently replaced LVP, carpets, electrical fixtures, plumbing fixtures and paint. Centrally located near by to shopping, schools, beaches and bases. Schedule your showing today!

257 Coachman Drive, Central Chesapeake
$615,000
3 Beds ⋅ 3 Baths ⋅ 10643157 MLS
This beautifully updated brick home combines comfort, functionality, and style with flexible spaces designed for modern living. At the heart of the home, the stunning kitchen features a custom island perfect for gathering, entertaining, and everyday life. Spacious bedrooms, versatile living areas, and an expansive sunroom provide plenty of room to spread out, with ideal spaces for a home office, virtual learning, hobbies, or creative pursuits. A true standout feature is the oversized two-car garage/workshop, complete with a full bath and approximately 780 square feet of unfinished space above—offering endless possibilities for guest accommodations, a studio, home gym, office, or additional storage. Step outside to enjoy beautifully landscaped grounds, custom decking, and an inviting patio designed for entertaining. A charming custom she-shed adds even more versatility, along with an additional flex space inside the home. Thoughtful updates throughout and adaptable spaces are a win!

103 Ashley Road, South Chesapeake
$345,000
3 Beds ⋅ 2 Baths ⋅ 10643168 MLS
Updated ranch in Western Branch with open floor plan. Kitchen has beautiful granite countertops and stainless steel appliances. Large bonus room that could be used as an extra bedroom, playroom, office, entertainment room, or family room. Fully fenced back yard with detached garage. Close to interstates, shopping, restaurants, and Military bases.

3036 Bomar Drive, West Chesapeake
$285,000
3 Beds ⋅ 1 Baths ⋅ 10643176 MLS
Welcome home to 3115 Hornsea Road, a lovingly maintained 3-bedroom, 1-bath ranch that radiates warmth, comfort, and true pride of ownership. Thoughtfully cared for and filled with timeless charm, this inviting home offers a bright, welcoming layout with abundant natural light that creates a sense of ease the moment you step inside. Recent major updates provide peace of mind, including new windows, an HVAC system less than 5 years old, and a roof less than 5 years old. The three bedrooms offer flexibility for family, guests, or a cozy home office. Step outside to a spacious backyard with mature landscaping and a peaceful patio, perfect for relaxing evenings. Additional highlights include an attached garage and a workshop with electricity, ready for hobbies or projects. Conveniently located near shopping, dining, parks, and more, this exceptionally cared-for home offers the kind of comfort and security that makes it easy to settle in and stay awhile.

3115 Hornsea Road, Central Chesapeake
$239,900
3 Beds ⋅ 1.1 Baths ⋅ 10643144 MLS

824 Huntly Drive, South Chesapeake
$435,000
4 Beds ⋅ 2 Baths ⋅ 10643102 MLS
This lovely Rancher style home has lots of room for you! Upon entrance you will see some of the wood laminated floors. The family room (18 X 16) with vaulted ceiling, has an open feeling plus gas fireplace. Roomy kitchen with lots of cabinet & counter space. Recently renovated Florida room (18 X 15). Lots of fresh painting, some new carpet and more! All bedrooms in this 4 bedroom rancher are goods sizes. Enjoy full front porch & deck off sunroom. Enjoy 2car garage with extra shelving for storage. Exterior trim recently painted.

2113 Quaker Place, Central Chesapeake
$289,500
3 Beds ⋅ 2 Baths ⋅ 10643125 MLS
This charming 3 bedroom, 2 bathroom home is ready for you! Featuring first floor primary bedroom and full bathroom for easy one-level living. Including fresh paint throughout the home with new carpets and recently updated LVP flooring. Centrally located nearby to beaches, bases, school, and shopping. Schedule your showing today!

1232 Stewart Street, Central Chesapeake
$949,608
4 Beds ⋅ 3.1 Baths ⋅ 10643106 MLS
Welcome to the Kentland by Kirbor Homes; where your Pinterest board finally gets to come to life! Designed for the way you really live, this home offers the perfect blend of style, comfort, and flexibility. With a luxurious first-floor primary suite, spacious open-concept living, and room to spread out upstairs, there's a place for everyone (and everything). The chef-inspired kitchen is ready for everything from holiday feasts to takeout nights, featuring our upgraded Chef's Appliance Package, a large center island, and plenty of space to gather. The great room is designed for game nights, movie marathons, or simply relaxing after a long day. Located in the sought-after Sanderson Estates, you'll enjoy spacious homesites, beautiful surroundings, and the quality craftsmanship Kirbor Homes is known for. Whether you're entertaining friends, hosting family, or just enjoying a quiet morning coffee on the porch, the Kentland is ready to fit your lifestyle. Come see why your next chapter deserves a home this fun to live in! Contact Listing Agent to schedule a tour or appointmnet at our design center today! Builder contract. Ask about Lender incentives!

1516 Cedarville Court, South Chesapeake
$900,000
7 Beds ⋅ 4 Baths ⋅ 10643086 MLS
Welcome home! This beautifully updated 7 bedroom and 4 full bath property offers over 3 acres of land and ample parking. First floor primary suite features a fireplace and upgraded bathroom with sleek tile. The kitchen boasts a large island, all new countertops, stainless steel appliances, and tile backsplash. Two upstairs bedrooms include full baths and walk-in closets. Open layout with recessed ceiling lighting, two fireplaces, and two sets of sliding glass doors lead to a spacious backyard. Schedule your showing today!

537 Margaret Drive, South Chesapeake
$350,000
4 Beds ⋅ 2.1 Baths ⋅ 10643022 MLS
Opportunity awaits in Western Branch! Nestled in a quiet cul-de-sac, this home offers solid potential for the right buyer willing to add their personal touch. With great bones and a desirable location, it’s priced accordingly and ready for updates and TLC. This property presents an excellent opportunity for investors or buyers looking to build equity. Don’t miss your chance to make it your own!

4209 Quailshire Court, West Chesapeake
$999,985
6 Beds ⋅ 4 Baths ⋅ 10642034 MLS
This gorgeous home can be your "White-House"!! Step into this ALL-White brick 2-story contemporary home with front porch, arches and large foyer, and be ready to fall in love! The backyard is a private oasis with trees, pond and flowing fountain. Enjoy the serenity of nature, including the blue herons, egrets, ducks and more, as you sip your morning coffee or have dinner on the patio. As you enter the first-floor foyer, notice the large formal dining room on the left that is perfect for entertainment, an archway to the 2 first-floor bedrooms (one currently being used as an office), full bath with shower and another archway to the large familyroom with gas fireplace. You will be excited by the huge open kitchen with granite counters, an oversized island, eat-in area and pantry. Also, on the first level is an archway inset that holds the Stiltz-Lift (elevator). Either take the wooden stairs with wrought-iron railings or the Stiltz to the 2nd level. Upstairs are the Primary bedroom with extra-large walk-in closet and an incredible ensuite bath, complete with 2 sinks, large, deep soaking tub, 5 x 4 ft shower with rainfall head and sit-down area. The primary bedroom has a gas fireplace and a wall of glass windows and french doors that lead to the Juliet balcony. A separate laundry room, three other bedrooms and 2 full bathrooms provide the space for family and friends to come and visit. BUT, there's more to complete the 2nd floor. Check-out the theater/game room (great for entertainment) and additional wrought-iron railings that overlook the stairs, foyer area and lead to the Stiltz lift doorway. The extra-large 3-car garage has enough room for your cars or anything else. BUT there's more!! YES, then there's the backyard oasis! Well, you'll just have to see it for yourself. This home is convenient to shops, restaurants, malls, stores, Greenbrier Country club, banks, parks, interstate, university and so much more!

1324 Simon Drive, South Chesapeake
$320,000
3 Beds ⋅ 1.1 Baths ⋅ 10642961 MLS
Single family two-story detached home located in the Norfolk Highlands section of Chesapeake. 3 bedrooms, 1.5 bathrooms. Spacious layout with a bedroom and half bathroom on the second floor. Many updates throughout completed in 2021. First floor laundry. Large lot with huge fenced in backyard with an oversized shed. Many updates completed in 2021.

1605 Laurel Avenue, Central Chesapeake
$580,000
4 Beds ⋅ 3 Baths ⋅ 10642916 MLS
Retreat to the expansive second-level primary suite, featuring a private sunroom, spacious loft, luxurious garden tub, separate tiled shower, and beautiful cherry hardwood flooring. The main level offers three additional bedrooms, two full bathrooms, and a generous sunroom complete with a built-in bar—perfect for entertaining or relaxing. Enjoy 3.16 acres of peaceful outdoor living, featuring a barn, chicken coop, and storage shed, offering endless possibilities for hobbies, animals, or gardening. Major updates provide peace of mind, including a new roof (2017), two-zone HVAC system (2020), and water heater (2023). Fresh interior paint throughout and brand-new downstairs carpet make this home truly move-in ready. Welcome Home!

2600 Saint Brides Road W, South Chesapeake
$499,900
4 Beds ⋅ 2.1 Baths ⋅ 10642834 MLS
This home is a Wellspring gem with valuable upgrades. The front lawn and spacious 2 car garage create a warm and inviting first impression. Inside, the thoughtfully designed first floor offers multiple living spaces including a formal living room, dining room, eat in kitchen and cozy den featuring a gas fireplace. A convenient half bath makes everyday living and entertaining a breeze. Upstairs has four generously sized bedrooms including a primary suite with vaulted ceilings. Throughout the home, you'll appreciate having no carpet and LVP in every bedroom. The deck right outside the patio door is superb for hosting, overlooking an expansive newly fenced backyard with endless possibilities for play, gardening, pets or outdoor gatherings. A storage shed provides additional space for tools and equipment. TESLA EV charger conveys. Loan is assumable.

405 S Monterey Drive, South Chesapeake
$309,000
3 Beds ⋅ 2.1 Baths ⋅ 10642451 MLS
Welcome home to this charming and spacious interior townhome, perfectly located in the heart of everything! Offering nearly 1,600 sq ft of well-maintained living space, this home has 3 spacious sized bedrooms & 2.5 baths, providing the perfect blend of comfort and functionality. Filled with character and warmth, the thoughtfully designed floor plan offers plenty of room to relax and entertain. Step outside to enjoy the private backyard an ideal space for morning coffee or weekend entertaining! Conveniently located just minutes from the interstate, shopping, restaurants, and everyday amenities, you'll love the ease of living this central location provides. With ample parking and a welcoming neighborhood feel, this home truly has it all.

1404 River Birch Run, South Chesapeake
$755,000
5 Beds ⋅ 3.2 Baths ⋅ 10642808 MLS
A Full Acre. Two Primary Suites. Room for Everyone — 1833 Benefit Rd, Chesapeake VA. Over 3,600 sf. Motivated sellers! Renovated 5-bedroom home on a full acre in Chesapeake — brand new carpet, all freshly painted. The space, privacy, and flexibility that rarely come together at this price point. Two primary suites, one up and one down, give you real options: multigenerational living, long-term guests, or a main-level owner's retreat. The downstairs in-law suite has its own private entrance — space for older parents, adult kids, or a home business with client access that never touches your living space. The renovated kitchen features stainless steel appliances and opens to living areas built for gathering. The upstairs primary offers double sinks and a large walk-in closet. A mudroom with half bath handles the daily traffic so the rest of the house stays put together. Outside is where this property separates itself. A wrap-around deck surrounds the above-ground pool — your built-in venue for summer weekends. The roundabout driveway and attached 2-car garage mean parking is never a problem, whether it's a cookout for twenty or just everyday life. And the full acre gives you room to add, expand, or simply breathe — no neighbors ten feet from your window. Homes with this much land, this much flexibility, don't sit long in Chesapeake. Schedule your showing today.

1833 Benefit Road, South Chesapeake
$469,000
4 Beds ⋅ 3.1 Baths ⋅ 10642809 MLS
Enjoy receiving the $41,000 equity Right Away as the recent appraisal value being $510,000.Very clean and well-maintained home just waiting for the right buyer. THIS IS PRE-APPROVED SHORT SALE SO THE BANK GUARENTEES TO ACCEPT THIS PRICE so it can be a quick and easy short sale.Selling As Is, this being short sale.Seller has the Clear Termite Letter.

1803 Honey Milk Road, South Chesapeake
$550,000
4 Beds ⋅ 2 Baths ⋅ 10642398 MLS
Welcome to 529 Royal Grant Drive in the desirable Cheshire Meadows area of Chesapeake. This well-maintained 4-bedroom, 2-bath ranch offers approximately 2,064 square feet of living space with a comfortable layout, office/study, finished room over the garage, and attached 2-car garage. The updated kitchen features granite countertops and stainless appliances, along with cathedral ceilings, skylights, a wood-burning fireplace, updated bath tile and fixtures, new interior paint, updated exterior vinyl trim, new exterior doors, and a new garage door and opener. The backyard is perfect for relaxing or entertaining with a deck, patio, privacy fence, storage shed, and salt system in-ground pool with new liner. Conveniently located near Great Bridge schools, shopping, restaurants, and commuter routes. A wonderful opportunity in a sought-after Chesapeake location. Listed at $550,000.

529 Royal Grant Drive, South Chesapeake
$365,000
3 Beds ⋅ 2.1 Baths ⋅ 10642611 MLS
Beautiful and meticulously cared for open concept, end unit condo located on a quiet cul-de-sac. Rare private wooded view from both the backyard and primary ensuite. Custom upgrades include a shiplap fireplace accent wall with elegant wood mantle, luxury vinyl plank floors, modern light fixtures, and an entryway accent wall with mounted hooks. Looks like a model home, recently painted and features tons of natural light. The kitchen has gorgeous 42" wood cabinets, granite counters, an island, SS appliances, 2 pantries, and bar seating, perfect for entertaining. Primary ensuite retreat features a beautiful wooded outside view, tray ceiling, 2 walk-in closets, dual sinks, and custom wood shelving with shiplap accent wall. Ceiling fans throughout. Convenient upstairs laundry. 2 car garage, vinyl fence, and private side entrance. This home has it all! Conveniently located for easy access to interstates, shopping, and entertainment. Fees include front yard landscaping and insurance policies.

706 Albertine Court, South Chesapeake
$1,750,000
4 Beds ⋅ 4 Baths ⋅ 10642797 MLS
Set at the end of a quiet Hunters Ridge cul-de-sac, this custom brick estate rests on three private, gated acres, held by a single owner since its 2006 build. Beyond its 5,707 square feet of main finished living space, the home offers approximately 1,800 additional square feet of year-round conditioned space. A two-story foyer with a curved staircase opens to formal rooms and a two-story great room with a see-through gas fireplace. The island kitchen features granite, stainless, and a wet bar. The primary suite is a private retreat with a tray ceiling and a spa bath with a soaking tub. A temperature-controlled pool room, a rarity in Hunters Ridge, holds a heated pool beneath vaulted, skylit ceilings for year-round swimming and entertaining. A detached guest suite of about 715 finished square feet adds a kitchenette and full bath, ideal for extended family or long-term guests. A three-car garage, brick-pillar drive, pergola with hot tub, and patios complete the grounds.

2505 Sylvia Court, South Chesapeake
$775,000
5 Beds ⋅ 2.1 Baths ⋅ 10642786 MLS
One of a kind property in Hickory area of Chesapeake with 2 (YES TWO) SFH that are legally deeded, WATERFRONT (ocean access) ~3.5 ac lot, with no neighbors in sight! Main house is over 3,000 sqft 5/2.5. Smaller house about 1200 sqft, 2/. Both have newer systems and New Roofs. Each home has its own Septic/Well system & pumped in 2024-large house/2025-small house. Property backs to 60 ft of riverfront that leads through the sounds and into the ocean. The main farmhouse has modern amenities but the old charm and character with original hardwoods, curved arches and entry ways, Juliet Balcony overlooking estate, 3rd floor finished attic bonus room and solid walk down basement foundation that can be turned into a finished room or used for storage. This home is solid and well maintained, being sold as is, seller to make no repairs. Call today for your private showing!

112 Station Road, South Chesapeake
$260,000
3 Beds ⋅ 2 Baths ⋅ 10642754 MLS
Layout & Design: This highly desirable corner unit boasts extra windows that fill the space with abundant natural light. The single-story, zero-stair design ensures easy accessibility throughout.Kitchen & Appliances: The bright kitchen features ample counter space and includes a complete suite of appliances in great condition (refrigerator, stove, dishwasher, and microwave).Outdoor Living: Step out onto your private, low-maintenance patio—the perfect spot to enjoy your morning coffee or relax in the fresh air.Storage Solutions: No need to compromise on space; the unit includes a dedicated outdoor storage shed for safely stowing bikes, gardening tools, and beach gear.Comfort & Convenience: Includes full size washer and dryer and year-round climate control.

4605 Woodmark Trail, West Chesapeake
$315,000
3 Beds ⋅ 1.1 Baths ⋅ 10642736 MLS
no showings until 07/08.

1360 Mill Lake Quarter, South Chesapeake
$950,000
5 Beds ⋅ 4 Baths ⋅ 10642562 MLS
Welcome to your own private backyard retreat! This beautifully updated home offers the perfect blend of stylish interior living and incredible outdoor entertaining. Step outside to a true backyard oasis featuring a stunning 6-foot in-ground pool with a new liner and pump, a covered lounge area, outdoor fire pit, built-in bar, outdoor kitchen with grill, and plenty of space to host family and friends all season long. A screened porch conveniently connects the outdoor living space to the home, creating seamless indoor-outdoor living. Inside, the nearly renovated kitchen is the heart of the home, showcasing gorgeous marble countertops, a spacious center island, all LG appliances, bar-height seating, and a built-in desk area great for working from home or everyday organization. The open-concept design flows effortlessly into the inviting living room, making entertaining easy. Upstairs, you'll find generously sized bedrooms with abundant closet space, including a spacious room over the garage that offers endless possibilities for a media room, playroom, guest suite, or home office. The luxurious primary suite is a true retreat, featuring a cozy sitting area with its own fireplace, an oversized walk-in closet, and a beautifully appointed en-suite bath complete with dual-height vanities, a private water closet, soaking tub, and separate walk-in shower. Light wood-look luxury vinyl plank flooring adds warmth and elegance throughout the main living areas, while plush carpeting creates comfort upstairs. Thoughtfully updated and impeccably maintained, this home offers the perfect combination of comfort, style, and resort-style outdoor living. Don't miss the opportunity to make this exceptional property your next home!

129 Greengable 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.