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$487,500
5 Beds ⋅ 2.1 Baths ⋅ 10642464 MLS
Lakefront 5 bedroom home in Grassfield High and Middle School District! Fully updated $60k of premium upgrades intended for a forever home! Quiet, sought-after neighborhood. Just minutes from shopping and interstate. Large property features a 30-yrnew architectural roof, all-new hardwood floors, and a new driveway. Interior boasts an office, formal dining, eat-in-kitchen with a new refrigerator, and a family room with a fireplace. Enjoy a Master bath upgrade ($30k) and pristine Trex deck in the large, fenced-in backyard.

517 Whisper Walk, South Chesapeake
$288,500
3 Beds ⋅ 1 Baths ⋅ 10642393 MLS
Cute 1 story cottage in the heart of Greenbrier Chesapeake on almost an acre of private wooded property. This charming 2 bedroom home with a bonus room that has been used as a 3rd bedroom (no closet). Bright and Airy vintage appeal. Galley Kitchen opens to dining room with arched opening to living room. Open concept with character. The property is zoned Industrial and the current legal use is residential (nonconforming-grandfathered) Buyers should independently verify requirements with the City of Chesapeake, for any plans for additions or redevelopment or converting to an Airbnb STR.

106 Greenbrier Road, South Chesapeake
$440,000
4 Beds ⋅ 2.1 Baths ⋅ 10641959 MLS
Discover timeless charm in this beautiful, traditional home located in the heart of Chesapeake. Featuring 4 bedrooms, 2.5 bathrooms, and a spacious two-story layout, this home includes a bedroom with its own en suite bath, making it great for guests or added privacy. Gather around the cozy fireplace on cool evenings, or enjoy casual meals in the bright breakfast area. Step outside to a fully fenced backyard, great for entertaining, pets, or relaxing outdoors. Recent upgrades, including new siding and roof (2021) and a remodeled primary bathroom (2025), enhance both the home's beauty and value. An attached garage and attic complete this exceptional property. Don't miss your opportunity to make this Chesapeake gem your own!

744 Helmsdale Way, South Chesapeake
$635,000
4 Beds ⋅ 2 Baths ⋅ 10641777 MLS
Welcome home to this charming 4-bedroom, 2-bath brick ranch nestled on 4.22 wooded acres at the end of a quiet cul-de-sac. Inside, you'll find a warm and inviting layout featuring a family room with a wood-burning fireplace, formal living and dining rooms, granite countertops, and beautifully updated primary and hall bathrooms. Step outside to relax on the new composite deck (2024), gather around the fire pit, or enjoy the peaceful wooded surroundings. The property also includes a detached 2-car garage with a finished studio apartment and full bath, plus a whole-house generator and water softener for added convenience. Offering space, privacy, and versatile living, this property is ready to welcome you home! You won't want to miss this one!

1345 Oak Ridge Drive, South Chesapeake
$372,000
3 Beds ⋅ 1.1 Baths ⋅ 10641756 MLS
Welcome home to this well-appreciated 3-bedroom ranch, offering comfortable one-level living and plenty of space to enjoy. The open-concept home features a cozy eat-in kitchen, a spacious den with fireplace, a separate living room, a large sunroom perfect for relaxing or entertaining, and additional outdoor patio. Recent updates include new flooring in the sunroom, fresh interior paint, new gutter covers, and a sealed attic for added efficiency and peace of mind. Roof was done in 2016, Refrigerator (2018) and dishwasher, microwave, and oven (2016). Appliances and mechanical systems have been consistently maintained through a home warranty program. This solid, well-cared-for home reflects pride in ownership and is ready for its next chapter.

468 Blanche Drive W, South Chesapeake
$649,900
4 Beds ⋅ 3 Baths ⋅ 10641168 MLS
Nestled on a quiet double cul-de-sac in the heart of Great Bridge, this beautifully maintained all-brick home offers the perfect blend of timeless character and modern comfort. Situated on a lush corner lot this custom 4-bedrm, 3-bath home features spacious bedrooms, hardwood floors, & custom updates designed for today's lifestyle. The renovated kitchen serves as the heart of the home, while the beautifully updated primary suite provides a peaceful retreat. Plantation shutters add warmth throughout and a light-filled sunroom overlooks the private backyard, where a large paver patio and expansive deck create an ideal setting for entertaining, gathering, or relaxing outdoors. Major improvements include an updated roof, encapsulated crawl, and an energy-efficient geothermal HVAC system, helping keep utility costs low while providing year-round comfort. Located in one of Great Bridge's most desirable areas, this home is the prime example of "they just don't build them like that anymore"

413 Wickwood Drive, South Chesapeake
$624,900
4 Beds ⋅ 2 Baths ⋅ 10641403 MLS
Enjoy the tranquility of this charming ranch nestled on a private lot spanning nearly 3 acres. The inviting floor plan welcomes you with a cozy living room featuring a fireplace and wet bar, creating a great space to relax or entertain. At the heart of the home, the kitchen is filled with natural light from two large windows and offers ample cabinet and counter space, along with stainless steel appliances. Just off the kitchen, the dining area allows for effortless gatherings and everyday living. The spacious primary suite provides a peaceful retreat with a large walk-in closet and private ensuite bathroom. The additional bedrooms are generously sized, offering flexibility for family, guests, or a home office. Outside, the expansive backyard and screened porch provide endless opportunities to enjoy the surrounding natural beauty and peaceful setting. Experience the best of country living with the convenience of a short commute to shopping, dining, and everyday amenities.

2448 Johnstown Road, South Chesapeake
$599,000
4 Beds ⋅ 2.1 Baths ⋅ 10641342 MLS
Spacious Riverwalk home offering over 3,372 sq. ft. with 4 bedrooms, 2.5 baths, a two-car garage, 2 decks with private views of the lake. Recent improvements include gas HVAC in 2022, roof approximate 6 years old, encapsulated crawl space, Anderson windows with warranty, and new kitchen appliances. Large family room and kitchen - great for everyday life and easy hosting. Enjoy Riverwalk amenities including clubhouse, pool, playgrounds, and tennis courts. A wonderful opportunity to personalize a spacious home in a sought-after Chesapeake community. Close to the Hospital, Dining, Shopping and Interstates.

220 Marsh Island Drive, South Chesapeake
$334,900
2 Beds ⋅ 2.1 Baths ⋅ 10639821 MLS
MOVE-IN READY! Desirable END UNIT townhome in sought after Greenbrier. Fresh paint and new carpet throughout make this beautifully updated home shine. The bright eat-in kitchen features stainless steel appliances and granite countertops. The spacious great room offers a dining area, cozy fireplace, and access to the large, fenced backyard with utility room and storage shed (shed conveys As-Is). A half bath and laundry room complete the first floor. Upstairs, you'll find two generous EN-SUITE bedrooms filled with natural light. The third-floor loft provides flexible space perfect for a home office, study area, media room, playroom, or guest retreat. Conveniently located near shopping, dining, parks, and major highways, this low-maintenance home offers comfort, style, and an easy commute. Schedule your private showing today!

1213 Killington Square, South Chesapeake
$744,900
3 Beds ⋅ 3 Baths ⋅ 10639959 MLS
Updated farmhouse charm on nearly 4 acres! This traditional home offers 3 bedrooms, 3 full baths, and a spacious finished room over the garage. Outside, enjoy designated pastures, a barn, and a detached two-car garage with a framed upper level ready for future expansion or flexible use. A unique property with room to enjoy the outdoors and endless possibilities. Back on Market due to no fault of the seller. We have a clear termite & mositure letter, home inspection, recent septic inspection and pump 4/2026 and ready for a quick close.

3536 Riverwood Crescent, South Chesapeake
$393,900
3 Beds ⋅ 1 Baths ⋅ 10639906 MLS
Looking for space, privacy, and one-level living? Welcome to this move-in ready brick ranch nestled on nearly half an acre in Deep Creek. Inside you'll find beautiful original hardwood floors, an updated kitchen featuring quartz countertops and a butcher block island, plus a spacious flex room perfect for a family room, home office, or game room. Outside offers a detached two-car garage, storage shed, and plenty of room for gardening, entertaining, or simply enjoying peaceful country living. Conveniently located just minutes from shopping, dining, and major highways, this home combines the tranquility of rural living with everyday convenience.

3516 Parr Lane, South Chesapeake
$190,000
2 Beds ⋅ 2 Baths ⋅ 10638211 MLS
Move-in ready and ideally located in the heart of Chesapeake! This well-maintained home features a spacious layout, two private terraces, and convenient access to shopping, dining, and major commuter routes. Property is being sold as-is. Home could use some TLC, offering a great opportunity to make it your own in a prime location.** SOME PHOTOS ARE VIRTUALLY STAGED.

717 Inlet Quay Unit H, South Chesapeake
$1,695,000
5 Beds ⋅ 3.2 Baths ⋅ 10637839 MLS
Set within the sought-after Woodards Mill “loop,” this beautiful landscaped property blends impressive living with peaceful privacy just minutes from everyday conveniences. Originally built in 1984 and fully reimagined beginning in 2001 by professional contractors, the home has been thoughtfully expanded to over 6,000 square feet of refined, comfortable living space. Every addition and update was meticulously planned and expertly executed. The heart of the home features an expansive family and entertainment room overlooking a spacious blue stone lanai. A stunning all brick sunroom adds warmth while the main level offers a generous primary suite along with three additional bedrooms (one used as home office.) Upstairs, a private second primary suite provides an ideal retreat for guests or multi generational living. Outdoor enjoy a true gardeners paradise with mature hydrangeas, peonies, irises and much more. The fenced saltwater pool with new liner offers both relaxation and peace of mind. Life on the loop brings a unique sense of community, known for its annual parades from Jingle Bell and Horse Parade to July 4th to the famous Halloween Parade. As an added everyday convenience enjoy school bus pick up and drop at the home. Miele, Thermador and Viking appliances. This home is not like any others sold in this neighborhood, a must see.

517 Woodards Ford Road, South Chesapeake
$449,900
4 Beds ⋅ 2 Baths ⋅ 10637343 MLS
Welcome home to this beautifully maintained 4-bedroom property in the heart of Great Bridge! Pride of ownership is evident throughout, with numerous updates and upgrades completed over the years. The spacious primary suite features a private full bath, while the inviting living room offers a cozy fireplace framed by custom built-in cabinets, creating the perfect gathering space. The versatile room over the garage serves as a fourth bedroom, home office, media room, or additional living area to fit your needs. Step outside to a large deck overlooking an expansive .37-acre fenced backyard with privacy fencing—ideal for entertaining, pets, gardening, or relaxing outdoors. Conveniently located in the Hickory School District and near shopping, dining, entertainment, parks, and commuter routes, this move-in-ready Great Bridge home combines comfort, space, and location. Don't miss this exceptional opportunity!

540 Aylesbury Drive, South Chesapeake
$290,000
3 Beds ⋅ 2.1 Baths ⋅ 10636106 MLS
Short sale — offer accepted and currently pending lender approval.

526 Windward Drive, South Chesapeake
$465,000
4 Beds ⋅ 2 Baths ⋅ 10636036 MLS
Nestled in the sought-after Homestead Acres community of Chesapeake, this beautifully maintained brick ranch offers the perfect blend of comfort, charm, and functionality. Enjoy an inviting open floor plan with spacious living areas, an updated kitchen, bright sunroom, and screened-in porch to enjoy year-round. Step outside to a large backyard retreat complete with a built-in firepit, great for relaxing evenings under the stars. Additional features include reverse osmosis system, water softener maintained by Moody’s, and HVAC less than 3 years old with smart system technology. Conveniently located near top-rated schools, shopping, dining, and more. Please ask details from agent on short sale details.

2744 Horseshoe Drive, South Chesapeake
$665,000
4 Beds ⋅ 2.1 Baths ⋅ 10634965 MLS
Welcome to one of Riverwalks finest victorian style homes. As a previous Homearama winner this property features 3 stories on almost a half acre of land with a salt water pool and wrap around porch. Featuring 4beds 2.5 baths with a 2 car garage.

302 Honey Locust Way, South Chesapeake
$405,000
3 Beds ⋅ 1.1 Baths ⋅ 10632703 MLS
Welcome to this stunning, move-in-ready masterpiece located in the heart of Hickory. This home has been meticulously renovated, boasting new siding for exceptional curb appeal and energy efficiency. Step inside to discover a bright, open interior featuring stylish new flooring throughout and a renovated kitchen complete with modern cabinetry and high-end finishes. Combining the charm of an established Chesapeake neighborhood with the luxury of a brand-new renovation, this home offers a rare opportunity to enjoy high-end living in a premier location.

224 Hickory Road E, South Chesapeake
$225,000
2 Beds ⋅ 2 Baths ⋅ 10631872 MLS
JUST PLAIN CUTE. WELCOME TO THIS BEAUTIFULLY UPDATED FIRST FLOOR 2 BED/2 BATH CONDO WITH THE SWEETEST COASTAL INSPIRED KITCHEN WITH CUSTOM MOSIAC TILE. ITS COZY. LOW MAINTNANCE AND PERFECTLY LOCATED NEAR SHOPPING, RESTAURANTS AND INTERSTATE! CONDO ASSN COVERS MASTER INSURANCE POLICY, GROUNDS MAINTENANCE, WATER, SEWER.

1718 Rock Bridge Mews Unit B, South Chesapeake
$470,000
3 Beds ⋅ 2 Baths ⋅ 10631816 MLS
Welcome to 152 Mann Drive in the heart of Great Bridge! This well-built brick ranch offers the perfect blend of charm and modern updates. Nearly every major improvement was completed in 2023, including luxury vinyl plank flooring, a fully updated kitchen, renovated bathrooms, HVAC system, and roof—giving you peace of mind for years to come. You’ll appreciate the seamless flow of the floor plan, designed for both everyday living and easy entertaining. Just off the kitchen, a cozy wood-burning fireplace creates a warm and inviting ambiance—perfect for relaxing evenings at home. With solid construction, stylish updates, and plenty of potential to make it your own, this is one you won’t want to miss!

152 Mann Drive, South Chesapeake
$529,900
5 Beds ⋅ 3 Baths ⋅ 10631480 MLS
This is one of those rare homes that truly supports multi gen or other uses. TRUE in law suite with kitchenette full LARGE bath, living and bedroom, private access. The roof, paint, carpet dishwasher ALL NEW to get ready to SELL ! Just a little personalization and this could be your dream home. Its just waiting for you. Full brick, masonary fireplace, oversized deck, extra driveway and a covered parking area. City and Zillow records not reflective of the current dwelling. Three generous bedrooms plus room over the garage AND the suite make this home a winner for you!

229 Fresno Drive, South Chesapeake
$264,000
2 Beds ⋅ 2 Baths ⋅ 10630690 MLS
Well desired community. First Floor corner unit, move-in ready. Beautiful wood flooring, updated appliances, large primary bedroom with bathroom. Condo amenities include a pool, clubhouse, tennis courts and close to trails.

708 Inlet Quay Unit B, 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.