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1428 Winslow Avenue, South Chesapeake
$390,000
4 Beds ⋅ 2 Baths ⋅ 10632026 MLS
Welcome to this spacious 4-bedroom, 2-bath home offering one of the largest floor plans in the neighborhood! Situated on a large corner lot, this property features an expansive backyard perfect for outdoor living, entertaining, the options are abundant. Including a detached garage with workshop space providing added versatility for hobbies, storage, or projects. Inside, enjoy a generously sized primary bedroom with a recently renovated en-suite bath and walk-in closet: creating a comfortable and updated retreat. Major system upgrades include a newer roof, water heater, and electrical panel for added peace of mind. The versatile layout offers ample living space for everyday living and entertaining. Ideally located near shopping, dining, bases, and major roadways—this home combines space, updates, and convenience you won't want to miss!

1428 Winslow Avenue, South Chesapeake
1219 Brookside Landing, South Chesapeake
$390,000
3 Beds ⋅ 2 Baths ⋅ 10630044 MLS
Welcome to this beautifully remodeled home in the heart of Greenbrier! This stunning 3-bedroom, 2-bath property offers modern updates throughout and true pride of ownership. Step inside to find a bright and open layout featuring updated flooring, fresh paint, and a stylish kitchen with upgraded finishes. The spacious primary suite includes a private en-suite bath, while two additional bedrooms provide flexibility for family, guests, or a home office. Enjoy the convenience of a one-car garage and a fully fenced backyard—perfect for entertaining, pets, or relaxing evenings outdoors. Ideally located near shopping, dining, interstates, and community amenities, this move-in ready home combines comfort, style, and convenience. Don’t miss your opportunity to own this turnkey property—schedule your showing today!

1219 Brookside Landing, South Chesapeake
1472 Otterbourne Circle, South Chesapeake
$389,900
3 Beds ⋅ 2.1 Baths ⋅ 10645889 MLS
This adorable 2-story, Townhouse-style, end-unit condo is conveniently located in sought after Hampshires @Greenbrier. The 1st floor features an open-concept layout consisting of an inviting foyer that flows into the formal dining room, Primary bedroom w/ensuite bathroom, walk-in closet, updated kitchen boasts quartz counter tops, stainless steel appliances, ample counter space, loads of cabinets for storage, family room w/cozy gas fireplace, utility closet, a powder room off the hallway for guests and access to the attached, 1- car garage & fenced-in patio area. The carpeted stairs lead to the 2nd floor that features 2 additional bedrooms, one w/an en-suite bathroom and large walk-in attic. Highlights include: some hardwood flooring, neutral carpet, lots of natural light & MORE! Neighborhood amenities include: a clubhouse, community pool & ample guest parking. Great central location adjacent to shopping, schools, parks, local beaches & highway access for an easy commute. Welcome Home!

1472 Otterbourne Circle, South Chesapeake
1201 Plantation Lakes Circle, South Chesapeake
$389,900
3 Beds ⋅ 2.1 Baths ⋅ 10633714 MLS
You do not see many corner/end unit homes pop up for sale in this neighborhood. Enjoy water views, with folks kayaking, paddling boarding, and fishing, from your own deck overlooking your beautiful fenced backyard. While inside your home, it boast of solid kitchen counter tops, tile bathroom floors, ceiling fans in all bedrooms. Updated appliances in the past year including washer, dryer and refrigerator, with the HVAC replaced only three years ago by R.A. Styron Heating & Air. Chesapeake near the Virginia Beach border. This is a home to be enjoyed inside and out.

1201 Plantation Lakes Circle, South Chesapeake
2315 Cross Street, South Chesapeake
$389,500
4 Beds ⋅ 2 Baths ⋅ 10630537 MLS
Welcome home to this charming ranch in a sought-after school district! Offering 3 spacious bedrooms plus a versatile FROG, this home easily adapts to your needs—home office, playroom, guest space, or workout area. Inside, enjoy a comfortable layout and a fantastic kitchen with plenty of room to cook and gather. All-electric systems make for efficient living. Major updates include a brand-new roof (2026) and HVAC (2025), water heater (2022), and newer fridge. The crawl space has a vapor barrier, and newer fencing adds value as well. Outside, the huge backyard is great for entertaining, pets, gardening, or relaxing evenings at home. Don’t miss your chance to make this home yours—schedule your showing today!

2315 Cross Street, South Chesapeake
204 Outlaw Street, South Chesapeake
$388,000
3 Beds ⋅ 2.1 Baths ⋅ 10631961 MLS
Welcome home to this inviting 3-bedroom, 2.5-bath property in Chesapeake, featuring gorgeous wood floors throughout the main level and plenty of natural light. The layout offers comfortable everyday living with a spacious loft and all bedrooms located upstairs, complete with carpet for added comfort. Spacious, fully fenced backyard with a large deck perfect for entertaining, relaxing, or enjoying time outdoors. A great combination of space, functionality, and charm.

204 Outlaw Street, South Chesapeake
4649 Backwoods Road, South Chesapeake
$387,000
3 Beds ⋅ 1 Baths ⋅ 10635736 MLS
Welcome to peaceful country living at its finest! Nestled on approximately 5 acres of cleared land, this charming ranch-style property offers the perfect blend of privacy, functionality, and opportunity. Great for horse lovers, hobby farmers, contractors, or anyone seeking room to spread out, the property features horse stalls, multiple outbuildings, and wide-open usable acreage ready for animals, equipment, recreation, or future expansion. The spacious ranch home provides comfortable single-level living with a relaxed rural atmosphere while still offering convenient access to Chesapeake amenities. Whether you envision a mini farm, equestrian retreat, workshop space, or simply enjoying sunsets over your own acreage, this versatile property delivers endless possibilities. Selling AS IS.

4649 Backwoods Road, South Chesapeake
504 Tuskegee Avenue, South Chesapeake
$386,000
3 Beds ⋅ 2.1 Baths ⋅ 10641078 MLS
This beautifully maintained home is open and bright with newer floors, kitchen, bathroom, and fixtures. All of the bedrooms are good-sized and there is a ton of closet space. The large deck overlooks a large and fully fenced backyard. Located just minutes from Greenbrier in the quiet and well-established Parkside neighborhood of Chesapeake, it is close to parks, shopping, highways, and bases. Great Bridge HS and the newly completed Crestwood Elementary are a huge plus! All you have to do is unpack!!

504 Tuskegee Avenue, South Chesapeake
1201 Brookside Landing, South Chesapeake
$385,000
3 Beds ⋅ 2 Baths ⋅ 10651042 MLS
Well maintained 3-bed 2-bath 1,577sqft ranch home in the Greenbrier area of Chesapeake. Pride of ownership shines by big-ticket updates including all-new exterior siding, trim & wrap by Window World in 2023, LeafGuard gutters 2022 that include a lifetime warranty, architectural shingled roof & windows installed within past 6-8 years. Interior upgrades last 5 years include, a tankless water heater, hallway shower & Corian countertops. The insulated garage is equipped with an AC unit. Relax in the backyard and entertain family & guests while sitting under the pergola or the retractable awning for shaded comfort. Plenty of extra storage besides the garage to include 2 storage sheds & an attic with pull down stairs. The neighborhood boasts scenic walking trails & playgrounds. Located close to interstate, shopping & restaurants, this home is ready for its new owner to make it their own. Call today before it is GONE!!!!

1201 Brookside Landing, South Chesapeake
1463 Winslow Avenue, South Chesapeake
$385,000
4 Beds ⋅ 2.1 Baths ⋅ 10650481 MLS
Welcome to 1463 Winslow Avenue! This well-maintained Chesapeake home is ready for its next owners. The current sellers have lovingly cared for the home for the past three years after purchasing it newly renovated, giving you the benefit of an updated home that has continued to be well cared for. Features include a newer roof and water heater, updated kitchen and bathrooms, and a newer backyard fence. Inside, you'll find 4 bedrooms, 2 full bathrooms, a half bath on the first floor and plenty of flexible living space. An additional bonus room gives you the freedom to make the space your own whether you need a home office, playroom, second living area, or hobby space. With thoughtful updates, flexible space, and a home that has been well maintained from top to bottom, 1463 Winslow Avenue is ready for you to move in and make it yours!

1463 Winslow Avenue, South Chesapeake
3329 Guenevere Drive, South Chesapeake
$385,000
4 Beds ⋅ 2.1 Baths ⋅ 10646350 MLS
Welcome to this beautiful 4-bedroom, 2.5-bath home nestled in the heart of the Camelot neighborhood! This move-in-ready home features newer luxury vinyl plank flooring, fresh interior paint, granite countertops, and stainless steel appliances. Offering a spacious and functional floor plan, you'll enjoy two separate living areas that provide plenty of room for entertaining, relaxing, or working from home. Situated on nearly a quarter-acre lot, the property also includes a huge two-car garage and a generous backyard with endless possibilities. Conveniently located just moments from Camelot Elementary School, the neighborhood park, shopping, dining, and more, this home truly has it all. Don't miss your opportunity to make this exceptional property your own! **Some photos have been virtually staged.

3329 Guenevere Drive, South Chesapeake
105 Cottonwood Lane, South Chesapeake
$385,000
3 Beds ⋅ 2 Baths ⋅ 10646690 MLS
ALL BRICK RANCH with Large Sunroom, HUGE Updated Eat-In Kitchen with New Cabinets, Quartz Countertops, & Stainless Steel Appliances; Fresh Paint, New LVP Flooring, & New Carpet; Living Room with Built-Ins & Formal Dining Room, Primary Suite with Updated Private Bath. New Windows & New Light Fixtures. Nice Backyard, Storage Shed, Attached Garage, & Off Street Parking. Established Neighborhood Convenient to Greenbrier, Summit Pointe, & Easy Access to I-64.

105 Cottonwood Lane, South Chesapeake
1519 Tallwood Circle, South Chesapeake
$385,000
3 Beds ⋅ 2.1 Baths ⋅ 10641471 MLS
Welcome home to this beautiful detached condo featuring an open and inviting floor plan designed for comfortable living and entertaining. The two-story living room fills the home with natural light and creates a spacious airy feel. The first-floor primary suite offers convenience and privacy complete with dual walk-in closets and an en-suite bath featuring dual vanity sinks. The kitchen boasts granite countertops, stainless steel appliances and a breakfast bar with counter seating, perfect for dining and gathering with guests. Upstairs you will find 2 additional bedrooms, a full bath and a loft overlooking the living room. This move-in ready home combines style, functionality and low maintenance living in the Greenbrier area. Don't miss this exceptional opportunity!

1519 Tallwood Circle, South Chesapeake
1616 Woodstock Court, South Chesapeake
$385,000
3 Beds ⋅ 2.1 Baths ⋅ 10638574 MLS
Experience effortless living in this beautifully updated Plantation Woods condo, where modern upgrades and low-maintenance convenience come together. The thoughtfully designed interior features elegant granite countertops throughout, brand-new stainless steel kitchen appliances, luxury vinyl plank flooring on the main level, and plush new carpeting upstairs. Spacious bedrooms offer generous walk-in closets, creating comfortable retreats with ample storage.Enjoy a lifestyle of ease with community amenities including a pool, while the low condo fee covers water, sewer, trash service, and grounds maintenance. Ideally situated near shopping, dining, and everyday conveniences, this move-in ready home presents an exceptional opportunity to enjoy stylish, carefree living in a sought-after community.

1616 Woodstock Court, South Chesapeake
633 Rock Drive, South Chesapeake
$385,000
4 Beds ⋅ 2 Baths ⋅ 10638253 MLS
Welcome home to this charming Deep Creek ranch, offering the perfect blend of comfort, space, and functionality. You'll love the open floor plan including: large living room centered around gas fireplace, kitchen, dining room, utility closet, & pantry. Downstairs you will also find 3 spacious bedrooms, including a primary suite. Off the kitchen you will find the FROG (the 4th bedroom). Outside you'll find a detached workshop with plenty of room for hobbies, along with an above-ground pool, fire pit area, deck, and playground perfect for entertaining. Located minutes from dining, entertainment, and interstate access.

633 Rock Drive, South Chesapeake
1117 Camelot Court, South Chesapeake
$385,000
4 Beds ⋅ 2 Baths ⋅ 10635113 MLS
Spacious ranch living with room to spread out, both inside and out. Situated on a large cul-de-sac lot, this well-maintained home offers very generous room sizes throughout, including 4 spacious bedrooms, a large living room, dining room, and an inviting eat-in kitchen refreshed with new flooring, painted cabinetry, new backsplash, recessed and pendant lighting, and new appliances (2024). The sunroom provides additional flexible living space filled with natural light, perfect for relaxing or entertaining. Other recent updates including new carpet (2023), new flooring in the foyer and sunroom (2024), and water heater (2018) Outside, the oversized detached garage offers an incredible combination of workshop space and added storage. Whole house generator conveys as-is and is not currently connected to propane. Well pump located in garage conveys as-is.

1117 Camelot Court, South Chesapeake
133 Mann Drive, South Chesapeake
$385,000
3 Beds ⋅ 1.1 Baths ⋅ 10631041 MLS
This beautifully maintained home is tucked away on a quiet street just minutes from the Intracoastal Waterway. Located in the heart of Great Bridge, you'll love being close to shopping, local restaurants, and everything you need for everyday living, while still enjoying a relaxed neighborhood feel. This home has been well cared for and thoughtfully updated over time, so you can move in without the stress of major projects. Big-ticket items like the roof, water heater, electrical panel, and some appliances have already been taken care of. The heating and cooling systems have been consistently maintained, helping keep things running smoothly year-round. Outside, you'll find even more to love. The home features a spacious deck, a large, fenced rear yard, and a storage shed for all your extras.

133 Mann Drive, South Chesapeake
1502 Long Parish Way, South Chesapeake
$385,000
3 Beds ⋅ 2.1 Baths ⋅ 10630804 MLS
Beautifully maintained and upgraded 3 bedroom, 2.5 bath condo offering 1835 sqft of comfortable living. This move-in ready home features new flooring throughout and elegant crown molding downstairs that adds a refined touch to the main living areas, newer HVAC unit, new paint throughout, updated kitchen, new windows, plantation shutters, and custom closets. The spacious layout is perfect for both everyday living and entertaining. The primary suite is located on the first floor and includes a fully remodeled bathroom with modern finishes, creating a private retreat. Additional highlights include Bluetooth ceiling fans with built in speakers. Enjoy low-maintenance living with a condo fee that covers water, exterior insurance, trash pickup, and access to community amenities including a pool and clubhouse. A perfect blend of space, style, and convenience to everything including shopping, interstates and restaurants. Don't miss this one!

1502 Long Parish Way, South Chesapeake
580 Etheridge Road, South Chesapeake
$385,000
3 Beds ⋅ 2 Baths ⋅ 10629550 MLS
Located in the highly sought-after Hickory area of Chesapeake, VA, this 3-bedroom, 2-full-bath home offers the perfect opportunity to build equity. If you’re searching for a home in Chesapeake, VA, with space, value, and long-term upside, this one deserves a look. Inside, you’ll find spacious rooms, a functional layout, and solid construction that give this home great bones. With a little TLC, this property can truly shine—making it ideal for buyers looking to personalize their space or invest in a Chesapeake, VA home for sale with built-in equity. Step outside to a huge fenced-in backyard, perfect for entertaining, pets, gardening, or simply enjoying your own private outdoor space. Opportunities like this—especially in Hickory—don’t come around often. Schedule your showing today and see the potential for yourself.

580 Etheridge Road, South Chesapeake
412 Tanners Green Court, South Chesapeake
$385,000
3 Beds ⋅ 2.1 Baths ⋅ 10627554 MLS
COMMUNITY BY ASHDON BUILDERS. EXTERIOR UNIT WITH 1ST FLOOR MASTER SUITE AND GARAGE; 2ND FLOOR FEATURES TWO BEDROOMS, BATH & LOFT AREA; OPTIONAL BONUS ROOM AVAILABLE; 9' CEILINGS ON 1ST & 2ND FLOOR; OPEN & SPACIOUS FLOOR PLAN WITH 2000+ SQUARE FEET OF LIVING AREA. ENCLOSED REAR YARD W/PATIO.

412 Tanners Green Court, South Chesapeake
520 Abelia Way, South Chesapeake
$385,000
3 Beds ⋅ 2.1 Baths ⋅ 10627285 MLS
Condo style townhouse awaits your fun lifestyle. As you enter your home you will see waterproof Cherry laminated, tongue & groove plank flooring in the living areas, the open kitchen with new microwave, plenty of storage and breakfast bar area. New lights throughout, Hunter ceilings fans, HVAC in 2024, new carpeting on stairs and 2nd level bedrooms, new LVP in laundry and hall bath. New dual bowl basin in primary bathroom, Moen faucets in all bathrooms. Travertine ledger panel stone around fireplace & kitchen backsplash. Freshly painted walls/trim throughout. All this, with 1 car attached garage and private patio area. 1 owner home awaits your furniture. Community pool, water/sewer included in fees. Beautiful, centrally located development that is established and shows pride throughout.

520 Abelia Way, South Chesapeake
801 Westbrook Lane, South Chesapeake
$385,000
3 Beds ⋅ 2.1 Baths ⋅ 10624884 MLS
Beautiful 3-bedroom, 2.5-bath townhouse with a 1-car garage located in the highly desirable Greenbrier area. This home offers comfortable living with a spacious layout and access to fantastic community amenities including a pool, tennis courts, basketball court, park, and scenic walking paths. Conveniently located near multiple shopping centers, restaurants, and entertainment options. Easy access to several military bases makes commuting simple. Don’t miss this opportunity to own in one of Chesapeake’s most sought-after areas.

801 Westbrook Lane, South Chesapeake
620 Norcova Drive, South Chesapeake
$385,000
3 Beds ⋅ 2 Baths ⋅ 10623540 MLS

620 Norcova Drive, South Chesapeake
2212 Carolina Road, South Chesapeake
$385,000
10606001 MLS
HORSE FENCE IS ELECTRIC AND TURNED ON. We offer 5.948 acres to build your new home, enjoy your horses, spend time on your hobbies! There is a 50' x 100' metal warehouse which has a partial concrete pad, power and well. Easy to show. REIN lockbox on side door of warehouse. Feel that country breeze, smell that country air!

2212 Carolina Road, South Chesapeake
521 Abelia Way, South Chesapeake
$384,900
3 Beds ⋅ 2.1 Baths ⋅ 10647937 MLS
You can be enjoying a great lifestyle when you decide to move to this townhouse/condo, convenient to stores, restaurants and interstates. Beautiful, sunny and inviting throughout. As soon as you walk in you will find engineered hardwood flooring, a cute sitting area and 1/2 bath. As you continue into your home you have a large dining area adjacent to the open kitchen with tile floors, and large island for extra seating. Your living room has built-in cabinet by the gas fireplace. Upstairs Is the laundry area, large primary with ensuite, hall bathroom and 2 additional bedrooms.

521 Abelia Way, South Chesapeake
1425 Otterbourne Circle, South Chesapeake
$384,000
3 Beds ⋅ 2.1 Baths ⋅ 10643380 MLS
Move right into this immaculate 3-BR, 2.5-bath condo offering 1,835 sqft of beautifully updated living space! Thoughtfully remodeled and upgraded with quartz kitchen countertops, stainless steel appliances, updated bathrooms, newer paint throughout, new HVAC units and new water heater. When first entering the unit, you will notice the attention to detail starts at the front door and doesn't stop with newly added crown molding that adds a refined touch to the main living areas. The primary suite is located on the first floor and includes a fully remodeled bathroom. Enjoy beautiful lake views from any rear window in the unit or while relaxing on your private back patio. The perfect spot for morning coffee or unwinding at sunset. Residents also enjoy access to a community pool and clubhouse, adding to the low-maintenance lifestyle. Fees also include water, sewer and trash pickup, as well as, the exterior insurance. Conveniently located near shopping, restaurants, major highways, and military bases.

1425 Otterbourne Circle, South Chesapeake
601 Bond Avenue, South Chesapeake
$383,000
3 Beds ⋅ 2 Baths ⋅ 10633998 MLS
This showstopper truly has it all! Open concept living meets exceptional functionality w/ a recently updated gourmet kitchen featuring custom cabinetry, granite countertops galore, induction cooktop, & wall ovens. The home offers a cozy wood-burning fireplace, 2 beautifully remodeled bathrooms, & a stunning primary suite w/ custom-designed walk-in closet. Car enthusiasts, hobbyists, & outdoor lovers will appreciate the incredible 25x35' detached garage featuring an 8x16' garage door, 10K lb 2-post automotive lift, pulling pots in the slab, new electrical wiring in 2025, 220V/60AMP service, plus an additional 650 sq ft insulated workshop w/ independent HVAC. The oversized carport, expansive driveway w/ space for 10+ vehicles, & dedicated parking areas for boats, campers, & recreational vehicles provide versatility. Enjoy outdoor living on the spacious deck w/ dedicated gas hookup for grilling, all with added benefit of no HOA. Bonus: 2.75% VA assumable loan for qualified VA buyers.

601 Bond Avenue, South Chesapeake
852 Royal Grove Court, South Chesapeake
$382,500
3 Beds ⋅ 2.1 Baths ⋅ 10648393 MLS
Welcome to 852 Royal Grove Court, a beautifully maintained 3-bedroom, 2.5-bath townhome in Chesapeake, Virginia. Offering 1,847 square feet, an attached one-car garage, and an open floor plan, this home blends comfort, style, and convenience. The first-floor primary suite features private patio access, a walk-in closet, a jetted walk-in tub, and a separate shower. The updated kitchen includes granite countertops, stainless steel appliances, generous cabinet space, and hardwood flooring. The spacious living area is filled with natural light and features a cathedral ceiling, skylights, hardwood floors, and a gas fireplace. Upstairs offers two additional bedrooms and a large loft that is ideal for a home office, media room, or flex space. Relax or entertain on the private patio overlooking the fenced backyard. Conveniently located near Greenbrier shopping, restaurants, entertainment, military installations, and major Chesapeake highways.

852 Royal Grove Court, South Chesapeake
3127 Patrick Henry Drive, South Chesapeake
$382,000
3 Beds ⋅ 2.1 Baths ⋅ 10647714 MLS
Welcome to 3127 Patrick Henry Drive, a beautifully maintained townhome nestled in the highly desirable Culpepper Landing community of Chesapeake. Offering 1,831 square feet of thoughtfully designed living space, this immaculate home features 3 spacious bedrooms, 2.5 baths, and stylish updates throughout. The open-concept floor plan provides comfortable everyday living while offering plenty of room for entertaining. Beyond the home itself, Culpepper Landing is one of Chesapeake's premier planned communities, offering an exceptional lifestyle with resort-style amenities. Residents enjoy a community clubhouse, swimming pool, fitness center, playgrounds, nature and biking trails and more! If you've been searching for a turnkey home in one of Chesapeake's most sought-after neighborhoods, this is one you won't want to miss!

3127 Patrick Henry Drive, South Chesapeake
655 Mill Creek Parkway, South Chesapeake
$382,000
3 Beds ⋅ 2.2 Baths ⋅ 10647229 MLS
Don't miss the chance to visit this beautiful well kept 3 bedroom townhome that offers a water view. This end unit shows like new with a first floor room that could be used as an office space or game room along with half bath. The main floor has a spacious open concept with a balcony off of the kitchen area. This townhome is apart of a fantastic community that offers great amenities, including a Clubhouse with an exercise room, Community Pool, Playgrounds, a Dog Park, Walking Trails, and Common Area Maintenance. HOA fees are due quarterly. This home won't disappoint. Seller willing to offer up to 3% CCA with full price offer.

655 Mill Creek Parkway, 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.

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