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308 Sikeston Lane, South Chesapeake
$415,000
3 Beds ⋅ 2.1 Baths ⋅ 10656271 MLS
This move-in-ready, 3-bedroom, 2.5-bath features recently installed carpet throughout, and a new dishwasher. The open-concept layout flows between the kitchen, dining, and living areas, creating a space for daily living and entertaining. Generously sized rooms offer flexibility for furniture placement, while deep closets and storage help with organization. The kitchen features soft-close drawers, granite countertops, a custom backsplash, and an island with accent lighting. Upstairs, the primary suite offers a walk-in closet, double vanities, and a walk-in shower with dual shower heads. The hall bath also features double vanities and direct access from the second bedroom. The attached garage and fenced backyard patio provide an ease with daily living. Enjoy local shopping and dining along with outdoor recreation at Great Bridge Lock Park along the Intracoastal Waterway. Nearby commuter routes connect you to military bases and destinations throughout the area.

308 Sikeston Lane, South Chesapeake

1316 Oregon Crossing, South Chesapeake
$545,000
4 Beds ⋅ 3.1 Baths ⋅ 10656134 MLS
Waterfront living awaits in this spacious 4-bedroom, 2.5-bath home offering room, comfort, and thoughtful updates throughout. The main level features beautiful porcelain tile flooring and a welcoming family room with a fireplace converted to gas. The eat-in kitchen offers abundant cabinetry and plenty of space for everyday living and entertaining. Generously sized bedrooms include two primary suites, updated baths with newly tiled shower, a large walk-in closet, and a private deck off one of the bedrooms overlooking the waterfront setting. Additional highlights include new carpet, updated vinyl siding, a new storage shed, large deck for summer living, new dock to fish off of and extended concrete parking with a 50-amp RV hookup. Every detail has been thoughtfully maintained, making this home truly move-in ready. A rare opportunity to enjoy waterfront living, don't wait on this one!

1316 Oregon Crossing, South Chesapeake

403 Caravelle Court N, South Chesapeake
$474,900
4 Beds ⋅ 2 Baths ⋅ 10656242 MLS
Charming ranch with large backyard and pool! Enjoy the welcoming front porch before heading inside to the thoughtfully updated interior, where fresh paint and beautiful new LVP flooring create a bright, inviting atmosphere. New carpet in the room above the garage adds comfort and versatility to the home's flexible living space. Designed for both everyday living and effortless entertaining, the home features a living room, dining room, and a cozy family room accented by wood beams and a fireplace. At the heart of the home, the eat-in kitchen offers all new sleek cabinetry, granite countertops, and stainless steel appliances. Four spacious bedrooms provide comfortable accommodations, while both full bathrooms have been refreshed with stylish new vanities. Outside, you're sure to enjoy the fully fenced backyard featuring a spacious deck overlooking the swimming pool creating an inviting setting for relaxing, entertaining, or enjoying warm summer days. Two storage sheds provide additional room for lawn equipment, tools, or hobbies, while the attached garage adds everyday convenience and extra storage.

403 Caravelle Court N, South Chesapeake

501 Spurlock Way, South Chesapeake
$597,999
4 Beds ⋅ 3 Baths ⋅ 10656230 MLS
Ready for a home that gives you more space to live, gather, entertain, and enjoy? This 4 bedroom, 3 bath home offers over 2,500 square feet with flexible spaces inside and a backyard that may quickly become your favorite place to be. The inground saltwater pool features a newer liner and cover plus newer pool pumps and support equipment, complemented by a covered brick porch and pool house with electricity and kitchenette. From weekend cookouts and evenings on the porch to warm days spent poolside, this outdoor space offers plenty of reasons to stay home and enjoy it. Inside, the remodeled kitchen features quartz countertops, updated cabinetry, stainless steel appliances, and a double oven, with plenty of space for cooking and gathering. New flooring in the living areas and new carpet in the FROG give the home a fresh feel, while new lighting throughout and a wood burning fireplace add to the appeal. A separate office with French doors and built-in bookcases provides dedicated space for working, studying, or projects. The spacious primary suite includes an updated bath with multiple shower heads. The FROG serves as the 4th bedroom and includes additional attic storage, while a large permanent stair attic provides even more room to keep everything organized. Situated on approximately .366 acres, the property also offers an extended driveway with room for additional vehicles or a camper, garden shed, fully insulated garage, zoned geothermal HVAC with a new heat system booster pump, new water heater, new front door, and new crawl space vent covers. With generous living space inside and an outdoor setting designed to be enjoyed for years to come, this is a home with room to gather, entertain, unwind, and truly settle in.

501 Spurlock Way, South Chesapeake

713 Rapidan River Court Unit G, South Chesapeake
$230,000
2 Beds ⋅ 2 Baths ⋅ 10655996 MLS
Freshly transformed and move-in ready! This second-floor corner end-unit condo in Chesapeake's Riverwalk community just had a full cosmetic refresh of the interior, including fresh paint throughout, an updated kitchen, new flooring and more. The single-level layout offers 2 bedrooms and 2 full baths. A wood-burning fireplace anchors the living area, and a private balcony overlooks mature trees. The primary suite has its own full bath. Beyond the cosmetic work, the home also has newer windows and a newer HVAC system. Kitchen appliances convey along with an exterior storage shed and two assigned parking spaces. The condo fee includes water, trash, grounds maintenance, the community pool and clubhouse.

713 Rapidan River Court Unit G, South Chesapeake

317 George Washington Highway S, South Chesapeake
$524,900
3 Beds ⋅ 2 Baths ⋅ 10655769 MLS
Five acres. A powered detached workshop. Room to breathe, space to make your own. This updated Cape Cod offers the flexibility of acreage living in Chesapeake’s Grassfield area. The home features 3 bedrooms, 2 full baths and a first-floor bedroom and full bath. MLS square footage reflects 1,869 sq. ft. per tax records; a recent appraisal measured approximately 2,067 sq. ft.Updates include a renovated kitchen and baths, replacement windows, updated electrical and plumbing, a 2023 heat pump, 2024 whole-house paint and newer flooring. Beautiful hardwood floors, a fireplace, and generous mud/laundry space add function and character. The approx. 736 sq. ft. powered detached garage/workshop offers room for tools, projects, and storage. Gorgeous outdoors boast a fenced yard area, wooded acreage, mature fruit and fig trees, enclosed porch, deck and patio. City water/sewer add convenience. Recent appraisal at $600,000! Existing VA loan may be assumable, reach out to listing agent for more details.

317 George Washington Highway S, South Chesapeake

1005 Winged Foot Court Unit B, South Chesapeake
$335,000
3 Beds ⋅ 2.1 Baths ⋅ 10656159 MLS
Welcome Home to this charming twin Home style Condo in Greenbrier's Fairways Villas. Tucked away in the cul-de-sac with garage, driveway, and communal parking, low maintenance living meets style and convenience. Enter into your inviting foyer greeted with LVP floors and neutral paint. Layout features large open concept great room and dining area. Eat-in kitchen is spacious with granite tops and stainless appliances. Access to one car garage and laundry off kitchen and half bath for the ultimate first floor layout. Second level features large primary bedroom with ensuite bath and walk in closet. Bedroom features natural light and vaulted ceilings. Two large spare bedrooms and hall bathroom complete this ideal layout. Large slider leads to rear deck which is large and tranquil backing up to golf course views. Newer HVAC & water heater 2021 and replacement windows. Call this Home Today!

1005 Winged Foot Court Unit B, South Chesapeake

1407 Hawick Terrace, South Chesapeake
$499,999
3 Beds ⋅ 3 Baths ⋅ 10656063 MLS
Welcome home to Chesapeake’s premier 55+ community! This move-in-ready home offers a fantastic and flexible floor plan featuring TWO spacious primary suites—one on each level—providing plenty of room for guests. The beautiful family room features soaring vaulted ceilings, luxury vinyl plank flooring, and a cozy gas fireplace. Just off the main living area is an additional first-floor flex space, perfect for a home office, reading room, or a relaxing spot to enjoy your morning coffee. The spacious eat-in kitchen features new stainless steel appliances and recessed lighting, while the formal dining room provides the perfect space for entertaining. The large first-floor primary suite offers a private bath with double vanity, separate shower, and oversized jetted tub. At the heart of the community is the Bay Club, featuring indoor and outdoor pools, hot tub, fitness center, billiards, library, game rooms, and so much more. Come experience resort-style living at Eagle Pointe!

1407 Hawick Terrace, South Chesapeake

109 Causeway Drive, South Chesapeake
$429,900
3 Beds ⋅ 2 Baths ⋅ 10655782 MLS
Welcome to 109 Causeway Dr, a charming home nestled on a quiet street in the highly desirable Great Bridge area of Chesapeake! Enjoy major peace of mind with recent big-ticket upgrades, including a newly updated HVAC system, new water heaters, flooring throughout, and the electrical panel in the garage updated within the last 2 years. One of the standout features of this property is the HUGE backyard—providing an abundance of open space for entertaining, gardening, or play. Plus, there is ample parking and side access with more than enough space to park your large RV, boat, trailer, or multiple vehicles. Location is everything! Situated just off Battlefield Blvd, you are minutes away from top-rated Chesapeake public schools, local parks, waterways, and the Intracoastal Waterway. You'll love the convenience of quick access to everyday shopping, dining, medical facilities, and major highways for an easy commute throughout Hampton Roads.

109 Causeway Drive, South Chesapeake

2220 Edwin Drive, South Chesapeake
$585,740
3 Beds ⋅ 3 Baths ⋅ 10656034 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2220 Edwin Drive, South Chesapeake

1145 Sunlight Drive, South Chesapeake
$475,000
4 Beds ⋅ 2 Baths ⋅ 10655999 MLS
Escape to your own private waterfront retreat on nearly 1/2 acre in the sought-after Inland Colony community, where peaceful wooded surroundings and serene water views create the perfect connection to nature. This 2,494 sq. ft. home offers 4 bedrooms, 2 baths, a first-floor primary suite, detached ADU, 1-car garage, and private dock with access to the Intracoastal Waterway on the Elizabeth River. Enjoy the expansive deck overlooking the backyard and water or unwind on the screened porch off the primary suite. Fresh paint and new carpet enhance the bedrooms, while the spacious kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and generous prep space. French doors open from the dining room to the living area, creating an ideal layout for entertaining. The FROG with new carpet and large walk-in attic provide excellent flexibility and storage. Some photos may be virtually staged. Conveniently located near shopping, dining, top-rated schools, and interstate access while offering a true waterfront escape.

1145 Sunlight Drive, South Chesapeake

144 Downing Drive, South Chesapeake
$569,900
4 Beds ⋅ 3 Baths ⋅ 10655754 MLS
Going live on 10/8. Welcome to 144 Downing Drive in sought-after Hickory, Chesapeake! This spacious & well-maintained 4-bed, 3 full-bath, brick & vinyl ranch offers plenty of flexible living space on a .27-acre lot. The inviting great room features a vaulted ceiling & fireplace, while the spacious kitchen offers granite countertops, abundant cabinetry, stainless steel appliances, breakfast area, & bright sunroom. The finished room over the garage with a full bath offers excellent flexibility for an in-law suite, guest space, home office, or bonus room. Enjoy a fenced backyard built for entertaining with a deck & above-ground pool. Additional highlights include an attached 2-car garage & generous driveway parking space. Located in the desirable Tunbridge Station community with NO HOA and convenient access to Hickory schools, shopping, entertainment, dining, military bases, & major routes to get around Hampton Roads. Schedule your private showing today!

144 Downing Drive, South Chesapeake

1741 Fortune Terrace, South Chesapeake
$425,000
3 Beds ⋅ 2.1 Baths ⋅ 10655498 MLS
Welcome to your next home, where every day feels a little more special. Nestled in the highly sought-after Bryan's Cove community, this beautiful home offers more than just a place to live; it offers a lifestyle defined by comfort, convenience, and connection. Enjoy added privacy with a peaceful wooded backdrop and no rear neighbors. With a low condo fee, no flood insurance requirement, and zoning for the highly desirable Grassfield school district, this home truly checks all the boxes. Bryan's Cove is known for its scenic surroundings and exceptional amenities, offering the perfect blend of tranquility and everyday convenience. Residents enjoy access to a community dock, dog park, fitness center, clubhouse, and swimming pool. Nearby, you will find Publix, lots of other shopping and several restaurants, Tidewater Community College, and quick access to Interstates 64 and 264 makes commuting and daily errands effortless, while parks, recreation, and local attractions are all close by. Inside, you'll find a warm and inviting floor plan designed for both comfortable living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring a large center island with seating, abundant prep space, and a gas range that will delight home chefs. Every room has been thoughtfully designed to create a welcoming atmosphere where family and friends can gather and lasting memories can be made. Opportunities like this don't come along often. If you've been searching for a home in an exceptional community with outstanding amenities, top-rated schools, and a private, natural setting, this is one you won't want to miss. Schedule your private showing today and experience everything this remarkable home has to offer.

1741 Fortune Terrace, South Chesapeake

3145 Codorus Street, South Chesapeake
$500,000
4 Beds ⋅ 2.1 Baths ⋅ 10655704 MLS
Seller is offering $3,000 to be used at buyers discretion!!! Beautifully updated and move-in ready, this home offers the perfect blend of comfort, style, and community. Recent improvements include luxury vinyl plank flooring throughout, a beautifully renovated primary bath with a spacious walk-in shower, and the addition of a fourth bedroom for added flexibility. Outside, the large backyard is framed by mature weeping willow trees, creating a peaceful retreat on a quiet side street. Beyond your front door, enjoy a lifestyle that’s hard to find—golf cart rides to the clubhouse, afternoons at the resort-style pool, workouts in the fitness center, visits to the dog parks and playgrounds, and a calendar full of neighborhood events including community picnics, book club, cigar & bourbon nights, festive holiday celebrations, and the beloved Christmas golf cart parade. Experience everything this vibrant, close-knit community has to offer in sought-after Culpepper Landing.

3145 Codorus Street, South Chesapeake

220 Marion Drive, South Chesapeake
$435,000
3 Beds ⋅ 2 Baths ⋅ 10655721 MLS
Location, Location, Location, Welcome to the desirable Great Bridge area of Chesapeake! This beautifully updated 3-bedroom, 2-bath home offers approximately 1,700 square feet of comfortable living space, with many of the major projects already completed. Inside, enjoy an inviting layout featuring a remodeled kitchen, refreshed bathrooms, new dishwasher 2026, 2019 AC system, and new 2025 evaporator coil. The cozy fireplace and chimney have also been professionally maintained, ready to enjoy. Outside, your private backyard retreat awaits! The inground pool is great for relaxing and entertaining, while the detached workshop offers versatile space for hobbies, projects, storage, or gatherings. The fully fenced yard provides privacy and plenty of room to enjoy. The home has been thoughtfully maintained, including 6-inch commercial gutters and professionally leveled and graded ground for proper drainage. The major mature trees around the home have been removed, reducing the potential for damage from falling limbs during severe weather. Additional improvements include a 2014 roof on all structures, plus a vapor barrier and dehumidifier installed in the crawlspace in 2019. The major work has been done—just unpack and enjoy! Come see everything this well-maintained Great Bridge home has to offer and schedule your private tour today.

220 Marion Drive, South Chesapeake

300 San Roman Drive, South Chesapeake
$289,900
2 Beds ⋅ 1.1 Baths ⋅ 10655553 MLS
Welcome to this beautifully refreshed 2-bedroom, 1.5-bath townhome tucked away on a quiet cul-de-sac in sought-after Las Gaviotas. Head inside to a spacious living area featuring a cozy brick fireplace and an inviting floor plan perfect for relaxing or entertaining. Recent updates include fresh paint, new flooring and carpet, 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 full bath, and large hall closet for extra storage. Enjoy a private fenced backyard and new deck, perfect for morning coffee, grilling, or unwinding. Conveniently located near shopping, dining, parks, interstates, Chesapeake City Hall, and Grassfield schools. Move-in ready and waiting for its new owner!

300 San Roman Drive, South Chesapeake

518 Whisper Walk, South Chesapeake
$465,900
4 Beds ⋅ 2.1 Baths ⋅ 10655312 MLS
Welcome home to this beautifully maintained condominium in the highly sought-after Cedar Crossing community. This spacious open concept residence offers over 2,000 square feet of comfortable living space. Four bedrooms featuring a large primary bedroom suite on first level, with double vanity and large walk-in closet. Beautiful hardwood floors, and crown molding throughout. Tile in kitchen, bathrooms and mudroom. Enjoy the privacy of a fenced backyard with storage shed for additional equipment. Two car garage and driveway space. Neighborhood has a well-equipped playground, swimming pool, tennis court and clubhouse. Enjoy low-maintenance living in a vibrant community conveniently located near shopping, dining, schools, and major commuter routes.

518 Whisper Walk, South Chesapeake

2207 Edwin Drive, South Chesapeake
$597,740
3 Beds ⋅ 3 Baths ⋅ 10655508 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2207 Edwin Drive, South Chesapeake

3221 Stefanie Court, South Chesapeake
$380,000
4 Beds ⋅ 3 Baths ⋅ 10655445 MLS
Experience the easy charm of Strawberry Acres! This 4-bedroom, 3-bath offers a desirable first-floor primary suite with a private bath, plus two additional bedrooms and a full bath on the main level. The finished room over the garage provides a private retreat with its own full bathroom, ideal for guests, multigenerational living, a home office, or bonus space. The fully finished garage adds versatility for hobbies, storage, or a workshop. Outside, enjoy a large yard with plenty of room for entertaining, gardening, play, or simply relaxing in a peaceful setting. Located near schools, parks, shopping, dining, and with quick access to I-64, this home offers the combination of convenience and everyday comfort. Seller is offering a flooring allowance with an acceptable offer, giving buyers the opportunity to personalize the home to their taste. Don't miss this exceptional opportunity to own a home that combines space, flexibility, and location at an affordable price right in Chesapeake!

3221 Stefanie Court, South Chesapeake

3605 Mostiler Place, South Chesapeake
$399,900
4 Beds ⋅ 2 Baths ⋅ 10655390 MLS
Beautiful 4-bedroom, 2-bath home tucked away on a quiet dead-end street in Chesapeake! Situated on an exceptionally large lot surrounded by mature trees, this home offers space, privacy, and plenty of possibilities. Inside you'll find spacious bedrooms, fresh paint, new flooring, updated ceiling fans and fixtures, along with newer siding and windows. One of the standout features is the impressive detached two-story garage/workshop—perfect for a workshop, home gym, office, recreational equipment, or additional storage, with incredible potential for future use. Enjoy a large backyard with plenty of room for entertaining, pets, gardening, or simply relaxing outdoors. Conveniently located near shopping, dining, parks, and everyday necessities. A unique property with tons of potential and room to make it your own!

3605 Mostiler Place, South Chesapeake

245 Old Drive, South Chesapeake
$410,000
3 Beds ⋅ 1.1 Baths ⋅ 10655362 MLS
THE OPPORTUNITY YOU'VE BEEN WAITING FOR! If you've been searching for a well-maintained home with space, character and room to make it your own, this is definitely the one. Situated on an oversized corner lot, this 3 bd, 1.5 bth home offers approx 1629 sqft, beautiful hardwood floors, generous living spaces and a layout with plenty of possibilities. Large room off of living room with a closet that can easily be a 4th bedroom, home office, gym, in-law suite with it's own separate side entrance. Large screened in patio leads to a HUGE backyard that can be transformed into an oasis offering room to entertain, garden or just relax. Workshop-like attached shed and a detached shed. It's move in ready and can be customized over time. No trendy renovations. No inflated renovation price tag. Just a solid home in a great location with great bones and the opportunity to add your own style. Located within blocks to shopping centers, dining, hospitals and interstates. Come see today!

245 Old Drive, South Chesapeake

716 Tallahassee Drive, South Chesapeake
$545,000
4 Beds ⋅ 2.1 Baths ⋅ 10655350 MLS
Exceptional opportunity in the sought-after Etheridge Lakes community located in the highly desirable Hickory High School district! This well-maintained 4 Bedroom, 2.5 Bath home offers comfort, space, and peace of mind with a NEW ROOF installed in 2026. The home features a functional layout perfect for everyday living and entertaining, with spacious bedrooms and plenty of natural light throughout. Versatile room downstairs for office needs or additional living area. All appliances convey, making this home truly move-in ready. Fenced yard offering privacy, yard space for pets or entertaining. 3 TVS convey! Enjoy the benefits of a well-established neighborhood with NO HOA fees or restrictions. Conveniently located near shopping, dining, parks, and major commuting routes, this home combines value, location, and pride of ownership in one outstanding package

716 Tallahassee Drive, South Chesapeake

3433 Martin Johnson Road, South Chesapeake
$394,990
3 Beds ⋅ 2 Baths ⋅ 10655347 MLS
Welcome to this charming 3-bedroom, 2-bath Cape Cod nestled on 1.4 private acres in the Deep Creek area of Chesapeake! This property offers the perfect blend of peaceful outdoor living and everyday convenience. Enjoy gardening in the fenced garden, unwind in the wooded backyard, or take advantage of easy access to the nearby Portsmouth Ditch Trail for walking, biking, and outdoor recreation. Inside, you’ll find a warm and inviting layout with classic Cape Cod character and plenty of space to make your own. Whether you’re looking for room to spread out, enjoy nature, or simply escape the hustle while staying close to shopping, dining, and major commuting routes, this home checks all the boxes. Don’t miss this unique opportunity to own your own slice of Deep Creek!

3433 Martin Johnson 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.