Refine Search
Sort by
$689,000
5 Beds 2.1 Baths 10644518 MLS
Beautifully maintained 5-bedroom, 3,383-square-foot home offering peaceful golf course views in sought-after Wedgewood Estates. The thoughtfully designed floor plan features spacious living areas, an updated kitchen with a large center island, abundant cabinetry, and an open flow into the family room, creating a welcoming space for everyday living and entertaining. Large rear windows fill the home with natural light while overlooking the golf course and a beautiful wooded backdrop. Step outside to enjoy the screened porch and expansive patio, creating a private outdoor retreat. Thoughtfully maintained and exceptionally cared for, this home combines timeless character, quality updates, and outstanding curb appeal. Conveniently located in the heart of Greenbrier, just minutes from shopping, dining, parks, major highways, military installations, and healthcare, while offering the privacy and charm of one of Chesapeake's most desirable established neighborhoods.

1118 Fairway Drive, South Chesapeake

$277,000
3 Beds 2.1 Baths 10644053 MLS
Well maintained, tenant occupied 1,275 sf, 3-bedroom, 2.5 bath Townhouse in Chesapeake's Woodgate Commons community. Ideally located near restaurants, shopping, interstate access, military bases, and a nearby golf course, this home offers both convenience and value. Recent updates include new first-floor flooring, remodeled bathrooms, fresh interior and exterior paint, updated kitchen appliances and floor coverings, an upgraded HVAC system, a smart thermostat & deck. The attached storage provides extra space for tools, seasonal items, or outdoor gear. The total community features 78 acres of common grounds w/ sidewalks throughout connecting neighborhoods, 7 playgrounds, a fishing pier, and a kayak ramp, offering plenty of outdoor recreation. Full of potential! Present tenant pays $2,200 per month on a 60-day notice lease.

1806 Beckwood Common, South Chesapeake

$470,000
4 Beds 2.1 Baths 10643910 MLS
Welcome to your dream Craftsman-style 4 bdrm 2 1/2 bath home w/a 2 car garage nestled in the heart of Chesapeake. This meticulously crafted residence offers a perfect blend of modern convenience & classic charm promising a lifestyle of comfort & sophistication. The heart of the home lies in the gourmet kitchen adorned w/luxurious granite countertops & equipped with stainless steel appliances. Whether you're whipping up a culinary masterpiece or enjoying a casual meal at the breakfast bar, this culinary haven Is sure to inspire your inner chef. As you venture outdoors, discover & enjoy your own oasis in the backyard waiting for your personal touch. With its prime location in Chesapeake, you'll enjoy easy access to local amenities, schools & major thoroughfares, ensuring that every convenience is w/in reach! Schedule your appt today to see this well built home! Photos are from previous build. Projected completion is August 2026.

1724 A English Avenue, Central Chesapeake

$320,000
3 Beds 2 Baths 10643699 MLS
Welcome home to this beautifully maintained 3-bedroom, 2-full-bath ranch in the heart of Chesapeake! Freshly painted throughout, this move-in-ready home offers comfortable one-level living with thoughtful updates and plenty of space to enjoy. Much of the home still has the original hard wood floors. The bright kitchen features a newly installed floor and brand new quartz countertops and sink. The spacious layout provides comfortable bedrooms and two full bathrooms. Step outside to a large rear deck, great for entertaining, grilling, or simply relaxing while overlooking the backyard. A standout feature is the 320-square-foot detached garage, offering excellent space for parking, storage, hobbies, or a workshop, not to mention an additional storage shed. Conveniently located in Chesapeake with easy access to shopping, dining, schools, and major commuting routes. Schedule your showing today!

1323 Ormer Road, Central Chesapeake

$379,900
3 Beds 2 Baths 10643565 MLS
Welcome to one of Chesapeake's best opportunities! This well-maintained brick ranch offers 1,976 square feet of comfortable living space with 3 bedrooms, 2 full bathrooms, and an oversized 520-square-foot attached two-car garage. The updated kitchen features quartz countertops and beautifully refreshed cabinetry, while numerous major improvements have already been completed, including a newer roof, inverter heat pump, refurbished concrete driveway and walkway, updated awning, LeafGuard gutters, and professional foundation repair. Situated on a generous 0.30-acre lot with no HOA and no flood insurance required, this home offers exceptional value, thoughtful updates, and pride of ownership throughout. Schedule your private showing today!

420 Oaklette Drive, Central Chesapeake

$389,000
3 Beds 2.1 Baths 10643380 MLS
Move right into this immaculate 3-BR, 2.5-bath condo offering 1,835 sqft of beautifully updated living space! Thoughtfully remodeled and upgraded with quartz kitchen countertops, stainless steel appliances, updated bathrooms, newer paint throughout, new HVAC units and new water heater. When first entering the unit, you will notice the attention to detail starts at the front door and doesn't stop with newly added crown molding that adds a refined touch to the main living areas. The primary suite is located on the first floor and includes a fully remodeled bathroom. Enjoy beautiful lake views from any rear window in the unit or while relaxing on your private back patio. The perfect spot for morning coffee or unwinding at sunset. Residents also enjoy access to a community pool and clubhouse, adding to the low-maintenance lifestyle. Fees also include water, sewer and trash pickup, as well as, the exterior insurance. Conveniently located near shopping, restaurants, major highways, and military bases.

1425 Otterbourne Circle, South Chesapeake

$444,000
3 Beds 2.1 Baths 10643564 MLS
Welcome to your golfer’s paradise on the 14th hole of Greenbrier Country Club! Meticulously updated, this stunning home blends modern elegance with everyday comfort. Come into a breathtaking living area showcasing soaring cathedral ceilings, high-end LVP flooring, and massive, picturesque windows that bathe the space in natural light while framing panoramic fairway views. Retreat to the first-floor primary suite—a true sanctuary beautifully reimagined with contemporary, spa-like finishes. Enjoy the lifestyle in the heart of Chesapeake, conveniently located just minutes from premier dining and shopping. Don't miss this rare opportunity to live on the green! Seller offering a $2,500 appliance credit.

927 Thatcher Way, South Chesapeake

$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

$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

$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

$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

$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

$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

$499,000
4 Beds 2.1 Baths 10642093 MLS
This beautiful home features a spacious floor plan designed for comfortable everyday living and effortless entertaining. The main level showcases an updated kitchen, beautiful hardwood floors in the main living areas, a tiled hallway, powder room, kitchen, and an oversized laundry room for added convenience. Upstairs, you'll find four generously sized bedrooms. The finished room over the garage offers exceptional flexibility and can easily serve as a fourth bedroom, game room, media room, home office, or playroom to suit your needs. Step outside to a large, fully fenced backyard featuring an expansive deck that's perfect for cookouts, outdoor dining, and entertaining. With plenty of room for kids and pets to play, this backyard is the ideal setting for relaxing, gathering with friends, and creating lasting memories.Centrally located, this home is just minutes from Greenbrier Mall, major interstates, Chesapeake Regional Medical Center, shopping, dining, and everyday conveniences. Combining space, versatility, and an unbeatable location, this move-in ready home is ready to welcome its next owners. Schedule your private tour today!

1028 Austin Drive, South Chesapeake

$370,000
4 Beds 2.1 Baths 10642424 MLS
Welcome to this exceptional end-unit luxury townhome, original owner bought as the community's model home. Built in 2014 and thoughtfully upgraded throughout, Thomason Trail offers nearly 1,900 square feet of living space, combining timeless finishes with everyday comfort. You'll appreciate the warmth of rich hardwood flooring, abundant natural light, and the attention to detail that sets this home apart. The kitchen is designed to impress, featuring granite countertops, ample cabinetry, a pantry and an open layout that flows seamlessly into the main living and dining areas. All of the mechanicals have been recently updated to include hot water heater 2026. Ceiling fans in every room plus custom wood blinds provide both style, privacy and comfort. One of the home's most distinctive features is the versatile loft, complete with custom built in shelves. Minutes from Greenbrier for shopping and restaurants you won't want to miss this opportunity.

1601 Thomason Trail, South Chesapeake

$379,800
5 Beds 2 Baths 10642460 MLS
Discover one of the best values in Chesapeake! This spacious 5-bedroom, 2-bath home offers over 2,100 square feet of versatile living space with room for everyone. Recent updates include a newer roof, updated HVAC, replacement windows, luxury vinyl plank flooring, fresh paint, and updated lighting, providing peace of mind and modern appeal. The bright kitchen features ample cabinet and counter space, while the open living and dining areas are perfect for everyday living or entertaining. The flexible floor plan includes generously sized bedrooms, making it ideal for a growing family, multi-generational living, or those needing dedicated home office space. Outside, enjoy a large fenced backyard with plenty of room for pets, gardening, play, or future outdoor entertaining. Conveniently located near shopping, dining, military bases, major interstates, parks, and schools, this home offers an easy commute throughout Hampton Roads. With five true bedrooms, substantial square footage, and numerous updates, this home delivers exceptional value compared to other homes in its price range. Whether you're a first-time buyer looking for extra space or an investor seeking a strong opportunity, this property is ready for its next owner. Don't miss your chance to own one of Chesapeake's best buys—schedule your private showing today!

4205 Nautilus Avenue, Central Chesapeake

$399,000
4 Beds 3 Baths 10641763 MLS
Welcome to this fantastic opportunity in the desirable Norfolk Highlands neighborhood! This versatile property features a spacious 3-bedroom, 2-bath main home plus a detached studio-style in-law suite complete with its own kitchen, full bath, and a new mini split system (2024)for heating and cooling great for multigenerational living, guests, or a private office. Enjoy a fully fenced backyard great for entertaining, pets, or relaxing outdoors. Two powered storage sheds provide ample space for storage, hobbies, or a workshop. Updates include a new HVAC system (2016) and new roofs on both the main home and detached suite (2016), offering added peace of mind. Conveniently located near shopping, dining, schools, and major commuter routes, this unique property offers flexibility, comfort, and value. Schedule your private showing today!

1415 Willow Avenue, Central Chesapeake

$432,400
3 Beds 3.1 Baths 10641733 MLS
Now accepting presale reservations, pending state condo document approval. Estimated early 2027delivery. The Caldwell plan offers a first-floor bedroom suite with flex space and one-car garage. 2 spacious owner suites are on the 3rd floor with convenient 3rd floor laundry. The main living area on 2nd floor features a large kitchen with abundant cabinets and countertop space, and 2nd floor balcony off the living room. Community will feature pool, playground, dog park and grilling stations, all surrounded by a protected forested area and conveniently located just 2 miles from Virginia Beach. Seller to pay up to $7,500 in closing cost assistance when using preferred lender, see agent for details. Special presale incentive: Receive a $12,500 anyway allowance to use at buyer's discretion when using seller's preferred lender, listed price reflects allowance taken off base price, see agent for details. Photos & video are of previous model, for illustrative purposes, finishes and upgrades vary in actual home to be built.

657 Allery Road, South Chesapeake

$437,400
2 Beds 2.1 Baths 10641732 MLS
Now accepting presale reservations, pending state condo document approval. Estimated Fall delivery. The Bristol plan offers 2 spacious owner suites on 3rd floor with convenient 3rd floor laundry. The main living area on 2nd floor features a large kitchen with abundant cabinets and countertop space, and 2nd floor balcony off the living room. First floor flex space with 2-car rear-loading garage. Community will feature pool, playground, dog park and grilling stations, all surrounded by a protected forested area and conveniently located just 2 miles from Virginia Beach. Seller to pay up to $7,500 in closing cost assistance when using preferred lender, see agent for details. Special presale incentive: Receive a $12,500 anyway allowance to use at buyer's discretion when using seller's preferred lender, listed price reflects allowance taken off base price, see agent for details. Photos & video are of previous model, for illustrative purposes, finishes and upgrades vary in actual home to be built.

670 Allery Road, South Chesapeake

$427,400
2 Beds 2.1 Baths 10641729 MLS
Now accepting presale reservations, pending state condo document approval. Estimated Fall delivery. The Bristol plan offers 2 spacious owner suites on 3rd floor with convenient 3rd floor laundry. The main living area on 2nd floor features a large kitchen with abundant cabinets and countertop space, and 2nd floor balcony off the living room. First floor flex space with 2-car rear-loading garage. Community will feature pool, playground, dog park and grilling stations, all surrounded by a protected forested area and conveniently located just 2 miles from Virginia Beach. Seller to pay up to $7,500 in closing cost assistance when using preferred lender, see agent for details. Special presale incentive: Receive a $12,500 anyway allowance to use at buyer's discretion when using seller's preferred lender, listed price reflects allowance taken off base price, see agent for details. Photos & video are of previous model, for illustrative purposes, finishes and upgrades vary in actual home to be built.

674 Allery Road, 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.