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$585,000
4 Beds ⋅ 2.1 Baths ⋅ 10643196 MLS
Welcome to this one of a kind custom all brick home designed for buyers who appreciate true craftmanship, architectural character, and timeless traditional design. Offering nearly 3000 sqft, 4 bedrooms and 2.5 baths, this home showcases features rarely found in newer construction, including a stunning wood spiral staircase, custom millwork, rich hardwood flooring, and 3 fireplaces that bring warmth and character throughout. This is not a builder grade flip or cookie cutter renovation, but a home built with quality, detail, and lasting charm. Outside, enjoy a private backyard retreat with a saltwater inground pool. Ideally located near local bases, shopping, dining, and major interstates, this is a rare opportunity to own a home with true character and lasting value.

913 Montebello Circle, South Chesapeake
$605,000
4 Beds ⋅ 2.1 Baths ⋅ 10642996 MLS
Welcome to luxury, low-maintenance living in the highly sought-after Westfield at Hickory Manor! This beautifully upgraded Galloway Model, built in 2018, offers 2,059 sq ft of stylish, thoughtfully designed living space with quality finishes throughout. The open-concept layout is superb for everyday living and entertaining, featuring spacious, light-filled rooms, an upgraded kitchen, a private primary suite, and flexible additional bedrooms. Enjoy resort-style amenities including a pool, 24-hr fitness center, clubhouse/community center, and playgrounds. Located in the sought-after Hickory School District with easy access to shopping, dining, military bases, major interstates, and more, this move-in ready home offers comfort, convenience, and lifestyle. Schedule your private showing today!

508 Cavendish Way, South Chesapeake
$295,000
2 Beds ⋅ 1.1 Baths ⋅ 10642955 MLS
Welcome home to this beautifully updated 2-bedroom, 1.5-bath townhome tucked away on a quiet cul-de-sac in desirable Las Gaviotas. Head inside to a spacious living area featuring a cozy brick fireplace, fresh finishes, and an inviting layout perfect for everyday living or entertaining. Recent improvements include fresh paint, new flooring, new carpet, an updated full bath, new rear deck, front porch railing, sliding glass doors, gutters, and water heater. Energy-efficient windows and kitchen appliances were replaced in 2020. Upstairs offers two generously sized bedrooms, a dual-entry bath, and a large hall closet for extra storage. Enjoy a private fenced backyard with a new deck, ideal for relaxing or entertaining. Conveniently located near shopping, restaurants, parks, major interstates, Chesapeake City Hall, and award-winning Grassfield schools, this move-in ready home is ready for its new owner.

300 San Roman Drive, South Chesapeake
$285,000
2 Beds ⋅ 2.1 Baths ⋅ 10643199 MLS
Back on market as of 7/22 at no fault to the seller. Move-in ready in the Villas at Culpepper Landing! This 1,454 sq ft condo packs 2 bedrooms, 2.5 baths, and a dedicated office into a bright, open floor plan with high ceilings and natural light throughout — great for entertaining or just everyday living. The kitchen is the heart of the home: granite countertops, stainless steel appliances, and plenty of cabinet space, flowing right into the open living and dining area. The office/flex space downstairs works as a home office, guest room, or hobby room — whatever you need it to be. Upstairs, both bedrooms come with their own private en-suite bath, so nobody's fighting over the mirror. Low-maintenance living comes standard here, with community amenities including a clubhouse, pool, fitness center, dog park, playgrounds, and walking trails. Easy access to I64 makes commuting anywhere in Cheasepeake, Norfolk or Virginia Beach possible Style, function, and location — this one's ready for its next owner.

503 Nesbit Drive, South Chesapeake
$285,000
2 Beds ⋅ 2.1 Baths ⋅ 10643393 MLS
Welcome to this beautifully maintained condo built in 2021, offering modern finishes and low-maintenance living in a prime location. This home features two spacious primary suites, each with its own private bathroom—perfect for flexibility, guests, or shared living. The open-concept layout creates a bright and inviting space, while the immaculate condition makes it truly move-in ready. Conveniently located near shopping, dining, and everyday amenities, this is an ideal opportunity for comfortable and convenient living.

2314 Alcott Way, West Chesapeake
$410,000
3 Beds ⋅ 2.1 Baths ⋅ 10643082 MLS
Welcome to this spacious 3-bedroom, 2.5-bath home offering over 1,900 square feet of comfortable living in the heart of Chesapeake's desirable Greenbrier area. The thoughtfully designed floor plan features generous living spaces, a welcoming great room with a fireplace, and an updated kitchen with beautiful quartz countertops that continue into the bathrooms for a cohesive, modern look. Step outside to enjoy the stamped concrete patio, added in 2021, providing the perfect space for relaxing or entertaining. Additional updates include a new HVAC system (2018), refrigerator (2024), and dryer (2026), offering peace of mind for years to come. Conveniently located within driving distance of shopping, dining, parks, Greenbrier's business district, major interstates, and military bases, this well-maintained home is ready for its next owner.

640 Sweet Leaf Place, South Chesapeake
$330,000
3 Beds ⋅ 2.1 Baths ⋅ 10643331 MLS
Seller is offering $5,000 toward the buyer’s closing costs with an acceptable offer! Welcome to this beautifully maintained 3-bed, 2.5-bath townhome built in 2020, offering the perfect blend of style, comfort, and low-maintenance living. The open-concept floor plan features a spacious kitchen with granite countertops, a walk-in pantry, and plenty of cabinet space, flowing seamlessly into the living and dining areas—can be used for everyday living and entertaining. Upstairs, you’ll find a generous primary suite with a private bath, along with two additional bedrooms and a full bath. Come outside to enjoy the private rear deck, designed for relaxing after a long day. Condo fees include water, sewer, trash, grounds maintenance, and playground access, making homeownership even more convenient. Ideally located near military bases, shopping, dining, and major highways, this move-in ready home offers exceptional value in the heart of Chesapeake. Take advantage of the $5,000 seller concession and schedule your private showing today!

2833 Estella Way, Central Chesapeake
$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
$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
$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

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.