Refine Search
Sort by
529 Wittington Drive, South Chesapeake
$559,000
5 Beds ⋅ 3 Baths ⋅ 10646652 MLS
This is classic Great Bridge living at it's best! Nestled on a quiet cul-de-sac in the desirable Southern Pines neighborhood, this beautifully maintained 5-bedroom, 3-bath home offers 2,491 square feet of versatile living space on a private, half-acre wooded lot. A standout feature is the in-law suite, complete with its own bedroom, attached sitting/living area, and full bath ideal for multigenerational living or long-term guests. Two bathrooms have been tastefully renovated, while the newer roof and replacement windows provide added peace of mind. The cozy living room features a gas log/wood-burning fireplace, and the finished room over the garage offers endless flexibility as a bedroom, playroom, media room, or home office. Relax on the welcoming front porch or entertain on the spacious rear deck overlooking the peaceful backyard. Complete with a 2-car attached garage, detached storage shed, and no HOA.

529 Wittington Drive, South Chesapeake

1324 22nd Street, Central Chesapeake
$299,900
3 Beds ⋅ 3 Baths ⋅ 10646337 MLS
Welcome to this beautifully renovated 3 bedroom, 3 bath home in Historic South Norfolk! Taken down to the studs and rebuilt with quality craftsmanship, this home offers the feel of new construction without the new construction price tag. This fully permitted renovation includes a new roof, windows, HVAC, plumbing, electrical, insulation, drywall, flooring, kitchen, bathrooms, siding, decks, and more. Enjoy the inviting covered front porch and open-concept living room and kitchen featuring granite countertops, soft-close cabinetry, and stainless-steel appliances. The first floor offers a bedroom, full bathroom, and laundry room. Upstairs, you'll find two private suites, including a spacious primary suite with a walk-in closet and private bath featuring a dual-sink vanity. A versatile bonus room is perfect for a home office or nursery. Conveniently located near the new municipal center, public library, Lakeside Park, the Jordan Bridge, Elizabeth River, shopping, dining, military bases, and interstate access. This home is a must-see!

1324 22nd Street, Central Chesapeake

1701 Weber Avenue, Central Chesapeake
$365,000
3 Beds ⋅ 2 Baths ⋅ 10645766 MLS
Welcome home to 1701 Weber Avenue! This beautifully maintained 3 bedroom, 2 bath home in Chesapeake offers an open floor plan with soaring cathedral ceilings, creating a bright and airy feel throughout. Brand new LVP flooring spans the entire first floor, complemented by new carpet upstairs, and the whole home has been freshened up with new paint from top to bottom. Enjoy peace of mind with a roof that's approximately 4 years old. The fully fenced backyard is nice for pets, play, or entertaining, and the two-car garage offers plenty of storage and parking. Updated landscaping rounds out the curb appeal. Don't miss this move-in ready gem — schedule your showing today! Seller to provide Clear Moisture & Termite papers. All appliances to convey "as-is."

1701 Weber Avenue, Central Chesapeake

1724 A English Avenue, Central 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

2851 Crossings Drive, West Chesapeake
$570,000
5 Beds ⋅ 3.1 Baths ⋅ 10642155 MLS
This beautiful home is perfect for multi-generational living, featuring 2 spacious primary suites—one located on the main level and another upstairs. The entertainer's kitchen is a standout, offering abundant granite countertop space, gas cooking, large pantry, and ample cabinetry for all your storage needs. Overlooks the family room and the expansive backyard. An additional flex room on the first floor provides endless possibilities such as a home office, fitness room, playroom, or hobby space. One of the largest lots in the neighborhood - more than one-third of an acre with a fully fenced backyard. The outdoor space is designed for everyday enjoyment, with patio pavers and room for a pool, garden, or play area. Other conveniences: Second floor laundry room. Two-car garage. Need to move before the new school year begins? We can make that happen!

2851 Crossings Drive, West Chesapeake

904 Jennings Ln, South Chesapeake
$522,900
3 Beds ⋅ 3.1 Baths ⋅ 10643531 MLS
QUICK CLOSE - First Time Buyer 5.5 rate, low down, NO PMI! Mid Century Coastal look! UPGRADES GALORE! Built by award-winning builder. Extensive Mohawk flooring through mid-level - Gourmet Kitchen w/Custom hood, 10' island with Quartz counters, GE Cafe 6 Burner Gas range, GE Cafe Dishwasher, and GE Cafe Microwave Drawer. 10' ceilings MAIN, 9' First & Third Floors, 2-zone HVAC w/thermostat on each floor. Primary bedroom with Walk-in CLOSET and spa ensuite Bath. Custom stair rail with 42" treads. Second Petite Suite with ensuite and large walk in and HUGE laundry room w/Linen closet. First floor bedroom with ENSUITE bath! Oversized 10'x19' screened Trex porch, 2-car garage, Tankless Water Heater - and more! LOW $95 condo fee w/Cabana, Fire pits, Bocce ball and Professional landscape and lawn maintenance..ready for easy living! Legacy is waiting for you!

904 Jennings Ln, South Chesapeake

432 Autumn Green Lane, South Chesapeake
$369,000
3 Beds ⋅ 2.1 Baths ⋅ 10643081 MLS
Welcome to your beautifully maintained turn-key dream home in the heart of Chesapeake. This wonderful condo features a high-efficiency HVAC system less than one year old, brand new carpets, freshly painted, 9' ceilings, crown molding, beautiful hardwood floors, custom blinds, upgraded lighting, alongside a convenient second-floor laundry room. The kitchen is a chef's delight, featuring granite countertops, tiled backsplash, custom cabinets with under-cabinet lighting and stainless steel appliances. Retreat to the primary suite, vaulted ceilings, an oversized walk-in closet, and a spa-like en suite bath complete with dual vanity sinks. Outside, the 1.5-car garage offers ample storage or workshop space, while the concrete patio is perfect for relaxing in your low-maintenance yard. Conveniently located near shopping, malls, restaurants, parks and easy interstate access. Don't miss out on this perfect Greenbrier location.

432 Autumn Green Lane, South Chesapeake

4633 Indiana Avenue, West Chesapeake
$290,000
3 Beds ⋅ 1.1 Baths ⋅ 10642760 MLS
Come view this home on 1.04 acres. It's a perfect starter home with a blank canvas for your buyers to make their own. It will require a little updating, but it is move in ready. Under the carpets are beautiful wood floors. The kitchen area has 2 gas stoves for anyone who loves to cook. All new gas lines were installed in entirety including the 2 gas stoves in the kitchen, May 2026, and were inspected by the City of Chesapeake. Leaf guards have been installed so there's no gutter cleaning. Purchasing this property will be like owning your own oasis in the middle of the established neighborhood. There's an RV hookup on the shed behind the home and a large RV carport and 2 other storage buildings/workshops. There's plenty of parking area for your guests, a designated fenced in gardening area, privacy, acreage and a peaceful rural setting. The potential for this homestead is endless. This home is near interstates, shopping, and schools. Bring your imagination and qualified buyers.

4633 Indiana Avenue, West Chesapeake

604 Glasgow Street, South Chesapeake
$710,700
5 Beds ⋅ 4 Baths ⋅ 10647806 MLS
OFFER ACCEPTED/ OPEN HOUSE 8/9 CANCELLED! Pool days, cozy nights by the fire, and room for everyone! Buyers will finally find the space they've been searching for at 604 Glasgow Street, offering over 3,400 square feet with 5 bedrooms and 4 full baths in beloved Cheshire Forest. Formal living and dining rooms lead to the heart of the home, where a timeless kitchen with cabinets for days opens to a spacious family room — great for hosting or simply gathering with family & friends. The first-floor bedroom and full bath is the answer for guests, multi-generational living, or a dreamy home office. Upstairs, the large primary suite is a true retreat, while the oversized FROG offers endless possibilities: fifth bedroom, media room, playroom — flex space galore! Out back, your own backyard oasis awaits: a large saltwater, in-ground pool, expansive (updated) tiered composite decking, and privacy for summer gatherings and quiet evenings alike. Cheshire Forest living is the cherry on top! A community pool with active swim team, tennis and pickleball courts, playgrounds, scenic ponds to fish in, walking paths, and year-round neighborhood events! All of this and still convenient to top-rated Great Bridge schools, local shopping, dining & the interstate.Thoughtfully designed with generous room sizes throughout, THIS is the one you’ve been waiting for!

604 Glasgow Street, South Chesapeake

1712 Ohio Street, Central Chesapeake
$323,000
3 Beds ⋅ 2 Baths ⋅ 10646831 MLS
Fully renovated and move-in ready! This beautifully updated two-story home offers 3 spacious bedrooms, 2 full bathrooms, plus a versatile bonus room great for a home office, nursery, playroom, or hobby space. The open-concept layout features a stunning kitchen with countertops, new cabinetry, and stainless steel appliances flowing into the living and dining areas. Enjoy peace of minds with major updates including the roof, windows, HVAC, plumbing, electrical, flooring, siding, front porch, rear deck, and concrete driveway. Both bathrooms have been tastefully remodeled with modern finishes, while the fenced backyard provides plenty of room to relax, entertain, or play. Conveniently located near shopping, restaurants, schools, major highways, military bases, and shipyards, this home combines quality, style, and functionality. Schedule your private showing today!

1712 Ohio Street, Central Chesapeake

920 Bellingham Drive, South Chesapeake
$475,000
4 Beds ⋅ 2 Baths ⋅ 10646475 MLS
Fantastic opportunity to own this beautifully maintained ranch in the desirable Etheridge Manor neighborhood. Situated on a spacious, deep lot, this single-family home has been meticulously cared for over the years. Inside, you'll find stunning hardwood floors, a welcoming fireplace, and a thoughtfully designed floor plan that's great for everyday living and entertaining. Recent updates include the HVAC system and water heater. The inviting front porch is the perfect place to relax, and the expansive backyard provides plenty of room for gardening, play, or entertaining. Conveniently located near shopping, dining, parks, and schools, this is a wonderful opportunity to own a fantastic home in an established neighborhood.

920 Bellingham Drive, South Chesapeake

1024 Weeping Willow Drive, South Chesapeake
$449,900
5 Beds ⋅ 2 Baths ⋅ 10646209 MLS
Spacious all-brick ranch offering 5 bedrooms in a highly desirable school district! Nice home features new flooring and a flexible floor plan designed for comfortable living. Enjoy a formal living room, formal dining room, and a cozy den with a wood fireplace. The eat-in kitchen offers plenty of cabinet space and includes a pantry for additional storage. The converted garage provides a versatile bonus space perfect for a home office, playroom, or hobby area. The first-floor primary bedroom adds convenience, while the room over the garage offers even more living space. Step outside to a privacy-fenced, spacious backyard complete with a deck, ideal for entertaining, relaxing, or enjoying outdoor activities. A rare opportunity to own a home with space, functionality, and an excellent location!

1024 Weeping Willow Drive, South Chesapeake

809 Obsidian Court, South Chesapeake
$751,000
5 Beds ⋅ 3 Baths ⋅ 10645845 MLS
Welcome to 809 Obsidian Court in the highly desirable Great Bridge area of Chesapeake—a beautifully maintained home tucked away on a quiet cul-de-sac in a welcoming, family-friendly neighborhood with NO HOA. From the moment you arrive, you’ll appreciate the pride of ownership and thoughtful upgrades throughout. Inside, the home features updated flooring, fresh paint, modern light fixtures, and stylish finishes that create a warm, move-in-ready space for everyday living and entertaining. Step outside to one of the property’s standout features: an expansive, fully fenced backyard offering endless possibilities for kids, pets, gardening, or hosting family and friends. The dedicated fenced dog run provides a safe and convenient space for your furry family members, while the storage shed with electricity for a workshop, hobby space, or additional storage. Located at the end of a peaceful cul-de-sac, this home offers minimal traffic and a quiet setting, making it available for outdoor play, evening walks, and enjoying the neighborhood atmosphere. With its spacious yard, thoughtful upgrades, and prime location near top-rated schools, shopping, dining, and major commuter routes, this home truly offers the best of comfort, convenience, and community. Don’t miss your opportunity to own this exceptional Chesapeake home—schedule your private tour today!

809 Obsidian Court, South Chesapeake

216 Marion Drive, South Chesapeake
$391,000
3 Beds ⋅ 2 Baths ⋅ 10641722 MLS
Welcome to this charming 3-bedroom, 2-bath bungalow ranch style home nestled on a spacious .46 of an acre lot in the heart of Great Bridge! Offering approximately 1,288 square feet of comfortable living space, this well-maintained home combines timeless appeal with modern updates. The inviting kitchen features granite countertops, a convenient pantry, and a cozy breakfast area, creating an inviting space for everyday living. Enjoy your morning coffee on the welcoming front porch or entertain family and friends on the back deck overlooking the large, fully fenced backyard. A standout feature of this property is the large two-story detached workshop with electricity, great for hobbies, a home workshop, or additional storage needs. Supplemental concrete has also been poured to allow for more convenient SUV, boats or recreational vehicle parking. Conveniently located just minutes from shopping, dining, parks, Intra Coastal Waterway and everyday conveniences, this home offers the a balance of peaceful living and accessibility. Don't miss the opportunity to make this Great Bridge gem your next home! Call now before it is gone!

216 Marion Drive, South Chesapeake

2307 Tybee Loop, West Chesapeake
$600,000
4 Beds ⋅ 3 Baths ⋅ 10636441 MLS
Home back on the market no fault of the seller's. Welcome to this beautifully upgraded Dogwood, built by Wirth, at 2307 Tybee Loop, built in 2021. The exterior impresses with premium stacked stone skirt and pillars. Inside, designed for seamless first-floor living, the main level features an open-concept eat-in kitchen with durable LVP flooring, a mosaic tile backsplash, and a sliding glass door to the screened in porch and deck. The kitchen boasts premium pull-out cabinets and a bump-out for extra storage. Convenient electric blinds service this kitchen area, the living room, and the primary. Extended by 5 feet allowing direct access to the outside, the primary suite features his-and-hers closets, an en-suite with dual vanities, and a custom tiled shower. An additional feature in the hall bathroom is the specialty walk-in jet tub. Upstairs has a spacious loft, a private en-suite, and walk-in attic space for storage. Relax on the screened porch overlooking a fully landscaped yard, backed by a whole-house 22kw Generac generator.

2307 Tybee Loop, West Chesapeake

2136 Edwin Drive, South Chesapeake
$508,000
3 Beds ⋅ 3 Baths ⋅ 10630716 MLS
Welcome to The Retreat at Edinburgh, a sought-after 55+ community offering low-maintenance living with exceptional amenities. This beautifully upgraded home features soaring ceilings, abundant natural light, and a spacious open-concept layout. The kitchen is a showstopper with quartz countertops, soft-close shaker cabinetry, stainless steel appliances, and a gas range, flowing seamlessly into a sun-filled dining area and inviting living room with a cozy fireplace and vaulted ceilings. The first-floor primary suite boasts a tray ceiling, oversized walk-in closet, and spa-inspired bath with dual vanities, quartz counters, and a tiled shower with frameless glass. Two additional bedrooms with access to a dual vanity hall bath and a versatile loft with a full bathroom provide flexible living space. Enjoy resort-style amenities including a clubhouse, pool, fitness center, and beautifully maintained grounds. A two car garage adds storage and convenience. Don't miss out on this gorgeous home!

2136 Edwin Drive, South Chesapeake

1916 Mccoy Road, South Chesapeake
$799,740
4 Beds ⋅ 4 Baths ⋅ 10617197 MLS
Home under construction- Summer delivery! Award winning builder curated this plant to honor the natural setting with a waterfront living surrounded by egrets, wildlife and protected land. This exclusive plan oversized windows will immerse you in light at every turn. Open and Elegant modern home. Extensive HW flooring and 10' ceilings midlevel, plus HUGE 2nd floor Screened Porch with Trex decking overlooking rear yard. True entertainers' home! Stunning primary bedroom with gorgeous views, egrets, and serene trees swaying in the breeze. Spa bath w/zero entry shower, freestanding tub, and 12' vanity. Black windows and gutters with Heritage black glass garage door. Custom Paver driveway and extensive landscape. Inquire to see extensive list of upgrades included. Breathe in the fresh air and NO HOA!

1916 Mccoy 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.

How much is your home worth?

Get instant property value now!