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$599,999
3 Beds ⋅ 2.1 Baths ⋅ 10643390 MLS
Move right into this beautifully upgraded, detached single-family home that perfectly pairs charm with an inviting, modern design. Built in 2014, this roughly 2,389 sq ft masterpiece is fully optimized for comfortable daily living and effortless entertaining. Main Level Highlights: Step through the welcoming entry foyer into a bright, open-concept floor plan radiating with natural light, custom blinds, and beautiful wood and laminate flooring. The expansive living space features a cozy electric fireplace. The updated kitchen boasts stainless steel appliances, a modern tile backsplash, crisp cabinetry, a large pantry, and a sunlit breakfast and dining area. Upper Level Retreats: Find ultimate comfort upstairs with a versatile second-floor loft that could be a home office, play area or convert into 4th Bedroom. The spacious primary bedroom suite serves as your personal oasis, offering a private retreat complete with an en suite bath and a large walk-in closet. Outdoor Living & Efficiency: Relax on the rear deck overlooking a sprawling, fully fenced backyard that directly overlooks a peaceful local farm. Large Modern Play-set conveying to buyer is negotiable. High-value capital updates include a new HVAC system in 2025, a tankless water heater, smart house features, and energy-efficient window tinting. Features an attached 2-car garage used for parking, storage, or a home gym. Centrally located near shopping, interstates, and area military bases. Bonus: Seller's preferred lender is offering closing cost assistance if utilized by buyer ask LA for more information!

712 Appalachian Court, South Chesapeake
$510,000
4 Beds ⋅ 2.1 Baths ⋅ 10643453 MLS
This beautifully maintained and tastefully designed 4 bedroom home in the highly sought after community of Culpepper Landing is waiting for you to call it home! At only 11 years old, it offers the peace of mind of low maintenance on your high ticket items such as HVAC, roof and windows. Not to mention, fresh paint floor to ceiling throughout, year old flooring on stairs and upstairs, the spacious front porch, dual walk-in closets in the primary bedroom and the perfect open concept downstairs living space with ample natural light and 9' ceilings. The 4th Bedroom on the main level is the perfect flex space, ideal for a home office, playroom or guest room! The golf-cart friendly community offers low maintenance living with exceptional neighborhood amenities, including a community pool, clubhouse, fitness center, playground and even a dog park! An additional benefit, a brand new elementary school is scheduled to open in 2027, tucked right inside of the neighborhood! Truly move in ready, this home offers comfort, style and convenience!

513 Simpson Lane, South Chesapeake
$320,000
3 Beds ⋅ 2.1 Baths ⋅ 10643459 MLS
Welcome to 709 Montrose Ct., Chesapeake, VA! This well- maintained two-story townhome offers 1,610 +/- sq. ft. of comfortable living space in a convenient location. Built in 1991, the home features 3 bedrooms, 2.5 baths, and a functional floor plan designed for everyday living. The spacious layout provides ample room for relaxing, entertaining, and working from home. Conveniently located near shopping, dining, schools, medical facilities, and major highways, this property offers easy access to everything Chesapeake has to offer. Whether you're a first-time homebuyer, downsizing, or seeking an investment opportunity, this townhome presents n excellent opportunity. Quarterly HOA fees help mINTin the community, providing added convenience nd peace of mind. Don't miss your chance to make this Chesapeake property your next home!

709 Montrose Court, South Chesapeake
$1,104,938
4 Beds ⋅ 3.1 Baths ⋅ 10643126 MLS
Warning: You may never want to leave home! Welcome to the Buena Vista by Kirbor Homes, where every room is designed to make everyday life feel a little more extraordinary. Whether you're hosting the holidays, cheering on your favorite team, or simply enjoying a quiet evening in, this home is ready for it all. The show-stopping kitchen is sure to become everyone's favorite gathering spot, featuring our upgraded Chef's Appliance Package, an oversized island, and plenty of room for everything from charcuterie boards to cookie decorating marathons. The open-concept layout keeps the conversation flowing from the kitchen to the dining area and great room, so no one ever misses out on the fun. When it's time to recharge, the luxurious first-floor primary suite offers the perfect escape, while the additional bedrooms and flexible living spaces provide endless possibilities for guests, hobbies, a home office, or that home gym you've been promising yourself. Step outside to the covered rear porch and imagine slow mornings with coffee, backyard cookouts, or winding down with a glass of wine as the sun sets. Located in the desirable Sanderson Estates, the Buena Vista pairs spacious homesites with the quality craftsmanship and thoughtful details Kirbor Homes is known for. This isn't just another new construction home—it's the kind of place where memories are made, traditions begin, and you'll happily volunteer to host every family gathering. Schedule your tour or Design Center appointment today and see why the Buena Vista might just ruin every other floor plan for you. Builder contract. Ask about available lender incentives!

2801 Raccoon Trail, South Chesapeake
$630,000
5 Beds ⋅ 3 Baths ⋅ 10643153 MLS
Home is being sold AS-IS.Come home to the beautiful 5bdrm, 3 bth with 3000 sqft of living space to enjoy. Freshly painted. Centrally located in the heart Great Bridge near shopping, dining, and the interstate.

1202 Copper Knoll Lane, South Chesapeake
$570,000
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 ⋅ 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
$329,900
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
$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, 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
$684,900
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
$489,500
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
$343,000
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
$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
$279,500
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
$890,000
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
$315,000
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 completed in 2021. First floor laundry. Large lot with huge fenced in backyard with an oversized shed.

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
$490,000
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
$755,000
5 Beds ⋅ 3.2 Baths ⋅ 10642808 MLS
A Full Acre of Land in the Heart of Southern Chesapeake.... Two Primary Suites. Room for Everyone! Over 3,600 sf. Renovated 5-bedroom home on a beautiful piece of land 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/owners 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. Sellers are motivated. Some images are digitally staged.

1833 Benefit Road, 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
$400,000
4 Beds ⋅ 2 Baths ⋅ 10642623 MLS
Welcome to 700 Cardover Avenue, where timeless character meets modern luxury in this beautifully fully renovated Chesapeake home. Offering 4 spacious bedrooms, 2 full baths, and approximately 1,900 square feet of thoughtfully reimagined living space, this stunning property blends classic charm with today’s most desirable finishes and functionality. Originally built in 1958, this home has been completely transformed to deliver a move-in-ready experience while preserving the quality craftsmanship and character buyers appreciate. From the moment you step inside, you’ll be welcomed by bright, airy living spaces filled with natural light and a warm, inviting atmosphere. The thoughtfully designed floor plan offers exceptional versatility with generous living areas and spacious bedrooms, creating the perfect balance of comfort and function. Whether hosting gatherings, enjoying quiet evenings at home, or creating flexible work-from-home space, this home adapts beautifully to your lifestyle. At the heart of the home, the seamless flow between living spaces creates an effortless environment for everyday living and entertaining. Every detail has been carefully curated to offer elevated style with modern convenience. Step outside to your private outdoor retreat featuring a brand-new backyard deck, suitable for morning coffee, weekend barbecues, evening gatherings, or simply unwinding outdoors. The deck creates an ideal extension of the home, inviting you to enjoy indoor-outdoor living year-round. Adding even more value and versatility, the detached garage offers excellent storage, workshop potential, hobby space, or additional parking—an increasingly desirable feature for today’s buyers. Conveniently located near shopping, dining, parks, schools, major commuter routes, and all that Chesapeake has to offer, this beautifully renovated home combines modern updates, functional living, and timeless appeal. This is more than just a renovation—it’s a fresh new chapter waiting to be written. Don’t miss your opportunity to make it yours.

700 Cardover Avenue, Central Chesapeake
$368,000
3 Beds ⋅ 2.1 Baths ⋅ 10641971 MLS
Embrace a life of vibrant neighborhood and comfort within this meticulously updated Chesapeake real estate standout. This pristine condition attached home features 3 spacious beds, 2.5 baths, a private one-car garage, and a spectacular master suite complete with a massive walk-in closet. Relax out back on your peaceful privacy-fenced patio. Schedule a showing today! Seller to provide closing costs assistance, and seller to pay HOA for the rest of the year!

2415 Fieldsway Dr, Central Chesapeake
$638,000
4 Beds ⋅ 2.1 Baths ⋅ 10642673 MLS
Welcome to your private country retreat! Nestled on 3 beautiful acres in the desirable Grassfield School District, this custom-built 2014 home offers the perfect blend of space, comfort, and privacy. Featuring 4 spacious bedrooms, 2.5 baths, and an open-concept layout for entertaining, this property is designed for both everyday living and peaceful relaxation. Enjoy the charm of country living with modern conveniences, surrounded by serene views and plenty of room to roam.

2828 Seven Eleven Road, South Chesapeake
$455,000
3 Beds ⋅ 2.1 Baths ⋅ 10642666 MLS
Beautiful 3 bedroom 2.5 bath home in the desirable Grassfield area of Chesapeake. This home offers a spacious layout with plenty of room for everyday living and entertaining. The kitchen has lots of cabinet and counter space and opens to the dining and living areas. The primary bedroom features a private bath and a walk-in closet. Roof replaced in 2017, windows replaced in 2021 and HVAC in 2025 for added peace of mind. Step outside to a fenced backyard that's great for kids, pets, or weekend cookouts. Conveniently located near Grassfield schools, shopping, restaurants, and interstate access. Move in ready and waiting for its new owners!

440 Fleming Circle, 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.