Refine Search
Sort by
803 Gresham Way, South Chesapeake
$615,000
5 Beds ⋅ 3.1 Baths ⋅ 10654210 MLS
Space, space and more space! With over 3,600 square feet, this HOME gives you room to spread out, work, gather and entertain. Hardwood floors flow throughout the majority of the home, while the spacious kitchen features granite countertops and stainless steel appliances. Do you work remotely? There’s a private first-floor office, too. Outside, enjoy an in-ground saltwater pool, Trex deck and gazebo for pool days, cookouts and relaxing at home. And there’s more—the detached garage is ideal for a workshop, hobby space, teen retreat or extra storage. Pool, detached garage, first-floor office, cul-de-sac and no HOA—all wrapped into one very spacious home. If space and flexibility are at the top of your list, this one deserves a look!

803 Gresham Way, South Chesapeake

1414 Loose Strife Place, South Chesapeake
$268,000
3 Beds ⋅ 2 Baths ⋅ 10654280 MLS
Experience airy, sun-drenched living in this beautifully updated two-story home. Enjoy an open living and dining space elevated by soaring ceilings, architectural skylights, and expansive windows that maximize natural light. Refreshed in 2026, the interior showcases brand-new flooring across both levelsfresh paint, and a new water heater. The fully serviced HVAC ensures year-round comfort. The sleek kitchen features premium granite countertops, stainless steel appliances, and a breakfast bar. A rare main-level bedroom and full bath offer ultimate flexibility. Upstairs, the primary retreat boasts vaulted ceilings, a walk-in closet, and an upgraded bath. Complete with clever storage and 2 assigned spaces, this home sits in a vibrant neighborhood featuring scenic ponds, green spaces, a pool, and a playground.

1414 Loose Strife Place, South Chesapeake

237 Castleberry Drive, South Chesapeake
$758,900
6 Beds ⋅ 3 Baths ⋅ 10653849 MLS
Set on more than half an acre in a quiet Great Bridge cul-de-sac, this all-brick 6-bedroom, 3-bath home offers space, flexibility, and thoughtful upgrades throughout. The spacious layout features a two-story foyer, formal dining room, private office/study, and an open living area leading to a well-appointed kitchen with granite countertops, center island, gas cooking, double ovens, stainless appliances, beverage fridge, and wine storage. A first-floor bedroom and full bath are ideal for guests or multigenerational living. Upstairs, the primary suite offers three walk-in closets, plus additional bedrooms, laundry, and a media room. Enjoy the expansive fenced backyard with a 10x16 shed, sprinkler system, and plenty of room to entertain. Additional features include a built-in generator, tankless gas water heater, surround sound, and two-car garage.

237 Castleberry Drive, South Chesapeake

302 Honey Locust Way, South Chesapeake
$635,000
4 Beds ⋅ 2.2 Baths ⋅ 10653782 MLS
Former Home-A-Rama award-winning home with character you simply don't find every day. Tucked away on a .43-acre cul-de-sac lot, this 3-story Victorian-style home offers approximately 3,100 sq. ft. of living space and a wrap-around porch. Inside you'll find hardwood floors, generous living and dining spaces, custom details, two fireplaces and two staircases. The gourmet kitchen features quartz countertops, black stainless appliances, custom cabinetry, island and pantry. Spacious bedrooms lead to an impressive primary suite with walk-in closet, ensuite bath and fireplace. A third-level bonus space offers flexibility for an office, study or workout room. Outside, an in-ground saltwater pool, multi-level deck, gazebo, fire pit and expansive backyard create a setting for entertaining or relaxing. A truly unique home ready for its next chapter!

302 Honey Locust Way, South Chesapeake

832 Woodrow Court, South Chesapeake
$475,000
4 Beds ⋅ 2 Baths ⋅ 10653661 MLS
Tucked away at the end of a quiet cul-de-sac, this exceptionally clean and carefully maintained 4-bedroom home offers comfortable living and added peace of mind with a newly installed roof with warranty. The spacious bedroom over the garage provides flexibility, while the sunroom adds another 180 square feet of living space overlooking a private, fully fenced backyard. Start your morning in the kitchen’s inviting breakfast area, unwind beside the wood-burning fireplace, or enjoy outdoor gatherings in the backyard. A separate utility room, efficient geothermal heating and cooling, and low-maintenance exterior trim add everyday convenience. The seller will provide a clear termite and moisture letter. Located within the Great Bridge school attendance area, this move-in-ready home is priced to sell and ready for its next chapter. Put this one on your showing list!

832 Woodrow Court, South Chesapeake

1232 New Born Court, South Chesapeake
$445,000
5 Beds ⋅ 2.1 Baths ⋅ 10653581 MLS
Welcome home! This beautiful home in Chesapeake is ready for its new owners! With 5 bedrooms, 2.5 bathrooms, and a layout designed to offer the perfect balance of togetherness and privacy, there is room for everyone. The kitchen offers plenty of cabinets and counter space and flows right into the open dining/living area. Two separate living spaces provide flexibility for entertaining, relaxing, or everyday living. Outside, enjoy a spacious backyard with a great deck, storage shed, and even a chicken coop! Located in a highly sought-after school district and a close proximity to shopping, dining and interstate access, this house checks all the boxes! Shed and chicken coop convey as-is. Don't let this one get away - call today to schedule your tour!

1232 New Born Court, South Chesapeake

1914 Keeter Run, South Chesapeake
$437,500
4 Beds ⋅ 2.1 Baths ⋅ 10653149 MLS
Welcome home to Greenbrier! This beautifully maintained, move in ready home is tucked away on a desirable cul-de-sac in the heart of Chesapeake. Featuring numerous recent updates, you can move in with confidence and enjoy! The kitchen was updated in 2024 with new cabinets, countertops, and appliances. All bathrooms were refreshed in 2025 with new vanities, sinks, tubs, toilets, flooring, and paint. Major updates include a roof (2017), fence (2021), HVAC furnace (2025), condenser(2026), and water heater (2026). The first floor offers a spacious foyer, open living and dining areas, plus flexible bonus space great for a home office or playroom. Upstairs features a large primary suite with private bath and walk-in closet, three additional bedrooms, and a spacious shared bath. Conveniently located near Greenbrier shopping, dining, interstates, and local attractions. Don't miss your opportunity to make this home yours!

1914 Keeter Run, South Chesapeake

804 Wakedale Arch, South Chesapeake
$719,900
5 Beds ⋅ 4 Baths ⋅ 10653264 MLS
Nestled on a cul-de-sac in Saddle Ridge Estates with NO HOA, 804 Wakedale Arch offers 3,720 square feet of spacious living with five bedrooms and four full baths. New hardwood floors, new carpet, and fresh paint throughout make this home move-in ready. An expansive sunroom just off the eat-in kitchen provides additional space for entertaining or relaxing. The generously sized primary suite features a sitting area, walk-in closet, and private bath with dual vanities, a separate shower, and soaking tub. A first-floor bedroom and full bath offer flexibility for guests or multigenerational living. Enjoy practical extras, including ample built-in garage shelving and a backyard shed with electricity. Space, comfort, and convenience come together in this beautifully refreshed home!

804 Wakedale Arch, South Chesapeake

952 Checkerspot Way, South Chesapeake
$685,000
5 Beds ⋅ 2.1 Baths ⋅ 10652920 MLS
Welcome to a home where thoughtful design meets effortless comfort. Beautifully updated with brand-new LVP flooring, this inviting residence is enhanced by an impressive collection of custom upgrades. The primary suite features a California Closets custom system, while the office offers tailored shelving and storage. In the kitchen’s eat-in area, a dedicated dog station and additional pantry provide both style and everyday functionality. Step outside and discover a private backyard backing to peaceful woods, complete with a fire pit—for relaxing or entertaining under the stars. The screened-in porch offers another inviting space to unwind and enjoy your favorite show. With the neighborhood playground just across the street, this home blends privacy, convenience, and thoughtful details in all the right ways. A home this special deserves to be seen!

952 Checkerspot Way, South Chesapeake

2916 Mintwood Drive, West Chesapeake
$275,000
3 Beds ⋅ 2 Baths ⋅ 10652244 MLS
REAL ESTATE AUCTION – PRICE SHOWN IS THE ADVERTISED STARTING BID, NOT THE SELLER’S RESERVE OR GUARANTEED SALE PRICE. This single-story brick ranch offers approximately 1,564 square feet with 3 bedrooms, 2 full bathrooms, an attached garage and a 0.332-acre lot. Live on-site auction Saturday, October 24, 2026, at 11:00 a.m. Reserve auction subject to seller confirmation. A 10% buyer’s premium will be added to the accepted high bid to determine the contract purchase price. Successful bidder must provide the required $10,000 deposit and close within 30 to 45 days. Property is offered as-is, where-is, with all faults and without financing, appraisal, inspection or other contingencies. Pre-auction traditional real estate offers may be considered until 48 hours before the live auction. Sealed absentee bidding is available under the published auction terms. Bidders must be registered by Thursday October 23, 2026 5pm. Buyers should complete all inspections, financing arrangements and due diligence before bidding. Auction documents are available through the listing agent.

2916 Mintwood Drive, West Chesapeake

700 Sarasota Arch, South Chesapeake
$595,000
4 Beds ⋅ 2.1 Baths ⋅ 10651170 MLS
Welcome to 700 Sarasota Arch, offering nearly 2,900 sq. ft. of versatile living space on a .36-acre cul-de-sac lot in Chesapeake's Etheridge Lakes community. This 4-bedroom, 2.5-bath home features a spacious floor plan designed for everyday living and entertaining. The family room is anchored by a gas fireplace with custom built-in bookcases, while the bright breakfast nook provides views of the backyard. A formal dining room adds additional space for gatherings and special occasions. The generous FROG serves as the fourth bedroom and offers flexibility for an office, media room, hobby space, or guest accommodations. Located within the Hickory School zone, this home combines space and flexibility. Bring your vision and make this home your own!

700 Sarasota Arch, South Chesapeake

1010 Cuervo Court, South Chesapeake
$599,900
5 Beds ⋅ 3 Baths ⋅ 10650705 MLS
PRICED TO SELL! Welcome to 1010 Cuervo Court, a spacious 5-bedroom, 3-bath home offering approximately 3,000 sq ft in sought-after Las Gaviotas! Flexible floor plan includes a first-floor bedroom and full bath, formal living room and a separate dining room. The large family room features cathedral ceilings, a stunning floor-to-ceiling brick fireplace, abundant natural light, and golf course views. Spacious primary suite offers a private balcony, large walk-in closet, and spa-like bath with dual vanities, jetted tub, and separate shower. Generously sized bedrooms, excellent closet space throughout, and a finished room over the garage provide plenty of space and flexibility. Additional features include a second level laundry room, side-loading 2-car garage, brand new dehumidifier recently installed in the crawlspace, newer carpet, and fresh paint in select rooms. Enjoy the charm of this established Chesapeake community with beautiful streets, golf course surroundings, cul dec sac living, walking trails, and highly regarded schools.

1010 Cuervo Court, South Chesapeake

MM Raccoon (Reba On 16-3) Trail, South Chesapeake
$755,166
3 Beds ⋅ 2.1 Baths ⋅ 10650490 MLS
Welcome home to the Reba floor plan by Kirbor Homes, situated on a picturesque 1+ acre cul-de-sac lot in Sanderson Estates! This 3-bedroom home offers a tranquil backdrop featuring scenic views of a neighboring pond and mature trees. Inside, enjoy a functional design complete with a spacious main-level layout with a spacious kitchen, breakfast area, and great room, along with an oversized 2-car garage with plenty of extra storage space. Low-maintenance living is made simple with a low HOA dedicated solely to community amenity maintenance. Great location just minutes from shopping, restaurants, and easy access to roadways to all areas of Coastal VA and NC. Serene views and room to spread out—schedule your consultation today to personalize your home details!

MM Raccoon (Reba On 16-3) Trail, South Chesapeake

1213 Killington Square, South Chesapeake
$319,000
2 Beds ⋅ 2.1 Baths ⋅ 10650185 MLS
MOVE-IN READY end-unit townhome in highly desirable Greenbrier! Fresh paint and brand-new carpet throughout give this home a clean, modern feel. The bright eat-in kitchen features stainless steel appliances and granite countertops, perfect for everyday living and entertaining. The spacious great room includes a dining area, cozy fireplace, and direct access to a large fenced backyard with storage shed and utility room (shed conveys As-Is). A convenient half bath and laundry complete the first floor.Upstairs offers two spacious en-suite bedrooms filled with natural light. The third-floor loft provides flexible space ideal for a home office, media room, playroom, or guest suite.Enjoy low-maintenance living in a prime location close to shopping, dining, parks, and major highways making commuting a breeze. Don’t miss this stylish, move-in ready home!

1213 Killington Square, South Chesapeake

3604 Harding Drive, West Chesapeake
$895,000
4 Beds ⋅ 3.1 Baths ⋅ 10650231 MLS
Prepare to be captivated! With a cool, contemporary flair and a spectacular waterfront setting, this one-of-a-kind residence is truly unlike anything else. Positioned on a coveted cul-de-sac with sweeping 270-degree views of the Western Branch of the Elizabeth River, this 4-bedroom, 3.5-bath contemporary home is an entertainer's dream and private retreat in one. With 4,889 sq ft of living space, soaring ceilings, expansive windows for tons of natural light, 3 fireplaces, high-end appliances, (ice maker as is), and a steam-shower create an atmosphere of effortless sophistication. Lush landscaping and an inground pool near the river is a rarity! Designed for unforgettable gatherings, sunset cocktails, or peaceful mornings by the water. Freshly painted inside and out, new 2026 architectural shingle roof, new hot water heater, and newer HVAC systems. Highly desired schools. Recent home inspection for serious buyers. Clear Termite & Moisture Inspection provided at closing.

3604 Harding Drive, West Chesapeake

808 Monroe Court, South Chesapeake
$429,900
3 Beds ⋅ 2.1 Baths ⋅ 10649872 MLS
Low-maintenance living awaits in this rare detached 3 BR, 2.5 BA Greenbrier condo. Enjoy a 2-car garage, fully fenced backyard, & primary en-suite and laundry on the first-floor. The open kitchen to main living area with gas fireplace. Additional flex room great for a home office, or media room. Recent 2025 updates include a new HVAC, granite counters with subway tile backsplash, LED recessed lighting, and more; washer/dryer replaced in 2021. Association handles exterior care; roof, siding, power washing, termite prevention, and front yard maintenance. Conveniently near Town Center, grocery stores, dining, parks, farmer markets & easy interstate access. This home blends convenience, comfort, and low-maintenance living beautifully.

808 Monroe Court, South Chesapeake

3520 Sugar Run, West Chesapeake
$187,500
2 Beds ⋅ 2 Baths ⋅ 10649902 MLS
$5,000 seller credit toward the buyer's closing costs, interest rate buy-down, or other allowable expenses. This well-maintained 2-bedroom, 2-bath first-floor condo in desirable Miars Farm offers comfortable single-level living in the heart of Western Branch. Move-in ready with a new HVAC system and hot water heater, plus newer stainless steel appliances. The spacious layout features two full baths and easy access to the rear patio with additional outdoor storage. Community amenities include a pool and clubhouse, with trash service and grounds maintenance included for added convenience. Ideally located near shopping, dining, schools, and interstate access, this condo makes everyday living simple and convenient.

3520 Sugar Run, West Chesapeake

3120 Deans Court, West Chesapeake
$575,000
4 Beds ⋅ 3 Baths ⋅ 10649657 MLS
$5,000 SELLERS CREDIT TOWARDS CLOSING COST, COSMETIC ALLOWANCE OR RATE BUYDOWN with full price offer. Beautiful, solid, all brick 2 story home sitting on a quiet cul-de-sac lot with almost half an acre. Well maintained home of 3,444 sq. feet with 4 bedrooms and 3 full baths. Large foyer that flows into a dining room, family room and gorgeous living room with built in bookshelves, pocket doors, fireplace & cathedral ceilings looking into an upstairs loft area. Open kitchen with breakfast area that leads to a 4 seasons sunroom where you can listen to baseball games over the summer. Enjoy FIRST FLOOR LIVING in a massive primary bedroom and a second spacious bedroom with hallway full bath. Windows galore and natural light throughout the home. Downstairs laundry room. Upstairs, a separate loft living space and 3rd bedroom with full bath. 4th oversized bedroom over the garage feels like a private oasis. Newer fully fenced backyard with above ground salt water pool. 2 car garage, whole house backup generator, tankless water heater and storage shed. Well irrigation system conveys "as is". Fresh paint within the last few years and other cosmetic upgrades. Minutes from all Western Branch Schools, baseball field, interstate and military bases.

3120 Deans Court, West Chesapeake

2808 Willows Arch, South Chesapeake
$469,900
4 Beds ⋅ 2.1 Baths ⋅ 10648837 MLS
Welcome to this beautifully maintained 4-bedroom, 2.5-bath home on a desirable corner lot in a sought-after, sold-out Chesapeake neighborhood. Tucked away on a quiet cul-de-sac, this home offers a spacious contemporary floor plan perfect for everyday living & entertaining. The main level features a formal living room, dining room, den, & open kitchen with stainless steel appliances and a bright sunroom. The spacious primary suite offers beautiful skylights, abundant natural light, & a private en-suite bath with a relaxing soaking tub. Enjoy outdoor living on the large deck overlooking the expansive backyard, perfect for gatherings, grilling, or relaxing. With generous living spaces, a functional layout, & a prime location, this home is a wonderful opportunity to own in an established neighborhood with No POA & minutes from everything!

2808 Willows Arch, South Chesapeake

608 Archer Court, South Chesapeake
$698,000
4 Beds ⋅ 2.1 Baths ⋅ 10648396 MLS
Welcome to sought-after Cheshire Forest! This beautifully maintained 4-bedroom, 2 and half bath home offers an open floor plan with a spacious family room flowing into a gourmet kitchen with breakfast nook. Rich acacia hardwood floors grace the first floor, complemented by ceramic tile in the kitchen and an elegant marble-tiled foyer. Escape to your private backyard oasis featuring an in-ground pool with a 2-year-old liner, Dolphin robotic cleaner, extensive decking, a fire pit, and rock landscaping around the pool for low-maintenance living—no mowing! A 135-ft. well adds convenience for irrigation. Enjoy outstanding HOA amenities, including an Olympic-size pool, clubhouse, two parks, pond for fishing, and home of the Flying Fish Swim Team. A rare opportunity in one of Chesapeake's premier neighborhoods!

608 Archer 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.

How much is your home worth?

Get instant property value now!