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$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
$885,000
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
$725,000
5 Beds ⋅ 2.1 Baths ⋅ 10642786 MLS
One of a kind property in Hickory area of Chesapeake with 2 (YES TWO) SFH that are legally deeded, WATERFRONT (ocean access) ~3.5 ac lot, with no neighbors in sight! Main house is over 3,000 sqft 5/2.5. Smaller house about 1200 sqft, 2/. Both have newer systems and New Roofs. Each home has its own Septic/Well system & pumped in 2024-large house/2025-small house. Property backs to 60 ft of riverfront that leads through the sounds and into the ocean. The main farmhouse has modern amenities but the old charm and character with original hardwoods, curved arches and entry ways, Juliet Balcony overlooking estate, 3rd floor finished attic bonus room and solid walk down basement foundation that can be turned into a finished room or used for storage. This home is solid and well maintained, being sold as is, seller to make no repairs. Call today for your private showing!

112 Station Road, South Chesapeake
$879,000
3 Beds ⋅ 2 Baths ⋅ 10642255 MLS
If these walls could talk, they would tell you 175 years of stories. Rare pre-Civil War farmhouse charm meets modern comfort in this private retreat that feels like a vacation every day. This 2-story home is filled with character, featuring 4 fireplaces, gorgeous original hardwood floors, 10-foot ceilings, hand-sawed original moldings, intricate ceiling details, and antique lighting. The living room offers a cozy wood-burning stove, while the family room showcases coffered ceilings and original hardwood floors. The spacious primary suite stands out with a beautiful fireplace and a wall of built-in cabinetry offering storage rarely found in modern homes. Enjoy two laundry areas, including one in the ADU over the detached tandem 4-car garage, plus a flexible space for an office or mudroom off the back of the main house. Outside, unwind and entertain by the pool oasis, or sit on the 250 sqft covered porch. There is a huge new chicken coop (26), and 2 dog runs for that farm life as well as a shed (as is). The brick walkways are the original bricks from the chimney repurposed. Updates include painted kitchen cabinets/walls (26), sealed and painted metal roof with 20 year paint (26), new pool liner (25), encapsulated crawlspace with dehumidifier/support beams (25), 50-gallon hot water heater (25), HVAC, and ductwork (23), new steps and railing out to the pool (26), breaker upgrade to house (25) 2 solar systems one to the main house and one to the ADU/garage (23). More updates listed in agent remarks. Near Hickory schools, shopping, Bypass, and OBX. Come own a piece of history in Hickory!

2410 Centerville Turnpike, South Chesapeake
$430,000
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
$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
$559,000
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, 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. Home needs TLC. Buyer can make it their own.

220 Marsh Island Drive, South Chesapeake
$475,000
3 Beds ⋅ 2 Baths ⋅ 10640771 MLS
Nestled off two quiet cul-de-sacs, this beautiful riverside ranch is the perfect candidate for a custom dream home transformation. Inside, the spacious layout kicks off with a large den centered around a classic wood-burning fireplace, showcasing original hardwood floors ready to be restored. The plan offers three sizeable bedrooms with large closets, a formal dining area, and a secondary rear den that opens to a large, screened-in porch. Off the kitchen, a sun-flooded breezeway provides excellent flexible square footage, great for a home gym or office. The real profit potential lies in the outdoor oasis. The backyard features an in-ground pool with a diving board, framed by palm trees. Fully fenced for privacy on the sides, the rear remains open to water views. Valuable waterfront infrastructure is already in place, including a concrete seawall and existing dock. Schedule your showing today! Some photos enhanced with AI to show maximum potential.

111 Goldcrest Drive, Central Chesapeake
$724,900
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
$434,999
5 Beds ⋅ 3.1 Baths ⋅ 10639654 MLS
Welcome to this spacious 5-bedroom, 3.5-bath home offering the size, features, and flexibility today’s buyers are looking for. With major items already in place, this property gives buyers the opportunity to add their own finishing touches while enjoying strong long-term value. The functional layout includes two ensuite bedrooms with private full bathrooms, two HVAC units for separate area comfort, a dedicated laundry room, and plenty of room for everyday living or entertaining. Outside, enjoy your own private pool, detached garage, and outdoor space made for relaxing or gathering. Conveniently located with easy access to major routes, shopping, dining, and local amenities, this home offers a rare combination of space, features, and opportunity.

316 Tudor Place, Central 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
$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
$184,900
3 Beds ⋅ 2 Baths ⋅ 10635979 MLS

1233 Transylvania Avenue, Central Chesapeake
$399,000
2 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
$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
$200,000
3 Beds ⋅ 1 Baths ⋅ 10627735 MLS
A brick house in the center of Plymouth Park neighborhood.

1317 Yeadon Road, Central 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.