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1731 Woodmill Street, South Chesapeake
$400,000
3 Beds ⋅ 2.1 Baths ⋅ 10625791 MLS
Located in the heart of Chesapeake’s Greenbrier area, this meticulously maintained detached condo is just minutes from shopping, dining, grocery stores, and major interstates—making everyday living easy. The main level features an open layout with impressive cathedral ceilings that create a bright and spacious feel. The kitchen is designed with granite countertops, upgraded cabinetry, and tile flooring, offering a functional and inviting space for everyday living. Upstairs, the primary suite includes a walk-in closet, jetted tub, and vanity. Two additional bedrooms, a full bathroom, laundry area, and a versatile sitting space provide plenty of room for guests, work, or relaxation. Additional highlights include a 16 SEER HVAC system, gas furnace, and gutter guards. A move-in ready home with thoughtful features throughout!

1731 Woodmill Street, South Chesapeake

23 Diamond Avenue, South Chesapeake
$400,000
4 Beds ⋅ 2.1 Baths ⋅ 10624743 MLS
Welcome home to this beautiful 4-bedroom, 2.5-bath home in Chesapeake located in the highly sought-after Grassfield School District. The kitchen features granite countertops, a built-in microwave, glass-top range, and dishwasher, and opens to the dining area with wood laminate flooring. The spacious primary suite offers a huge walk-in closet and a private bath with dual vanity sinks, granite countertops, and a separate soaking tub and shower. Additional highlights include ceiling fans throughout, updated fixtures, fresh paint, a new hot water heater, and all new flooring downstairs and the upstairs bathroom. Enjoy outdoor living in the large fenced backyard, perfect for relaxing or entertaining. Conveniently located just minutes from I-64, shopping, the Norfolk Naval Shipyard, and multiple military bases.

23 Diamond Avenue, South Chesapeake

1400 Fentress Road, South Chesapeake
$399,900
4 Beds ⋅ 2 Baths ⋅ 10633925 MLS
Step into a timeless sanctuary nestled on a serene 1-acre lot, this charming 4-bedroom, 2-bathroom home offers the perfect blend of tranquility and convenience. Enjoy the privacy and peace of country living while still being within easy reach of city amenities. Step inside to find spacious interiors filled with natural light and cozy ambiance. Originally built circa 1898, this property exudes character and warmth. The four generously sized bedrooms provide ample space for everyone, while the two bathrooms ensure comfort and convenience. Outside, your private oasis awaits. Imagine spending your days enjoying the outdoors, gardening, or simply unwinding on your expansive property. The possibilities are endless! Don't miss this opportunity to make this peaceful retreat your own. Schedule a showing today and experience the lifestyle you've been dreaming of.

1400 Fentress Road, South Chesapeake

3408 Winterhawk Court, South Chesapeake
$399,500
3 Beds ⋅ 2 Baths ⋅ 10638336 MLS
Nestled in a fun-friendly quiet cul-de-sac, this well-maintained ranch offers comfortable living with thoughtful updates throughout. LVP flring extends through the home, creating a clean & cohesive feel. The generously sized primary bdrm features a recently remodeled bath with an oversized walk-in shower. The kitchen offers abundant cabinet space, providing plenty of room for storage and meal preparation. Updated windows and patio door (2019) fill the home with natural light, while cozy & comfortable inside with a 2023 HVAC . The fp has never been used by the current owner. Outside, enjoy a spacious backyard with room for gardening, outdoor activities, or simply relaxing. An oversized two-car garage and large storage shed provide exceptional space for tools, equipment, hobbies, and seasonal items. The home is under a termite contract, and the seller will provide a clear termite letter. Combining updates, storage, and outdoor space, this move-in-ready home is one you won't want to miss.

3408 Winterhawk Court, South Chesapeake

1013 Stern Way, South Chesapeake
$396,000
3 Beds ⋅ 2.1 Baths ⋅ 10635810 MLS
The Mendelssohn lower-level features 2-car garage & massive rec room w/ access to private back yard that backs up to woods! Nest thermostat & wi-fi enabled garage opener! The main living level kitchen includes granite island, dining area, pantry & access to 8'x18' composite deck. The kitchen opens onto a bright/airy living room w/ a conveniently placed powder room. Upstairs are 2 guest bedrooms w/ ample closet space, a hall bath & convenient 2nd floor laundry room along with the generous owner’s bedroom which features a tray ceiling & walk in closet. A separate owner’s bath features a double-bowl vanity & oversized shower. No flood insurance required. A private marina club, docks, boat tie-off. POOL, CLUBHOUSE, FITNESS CENTER, PLAYGROUND & DOG PARK.

1013 Stern Way, South Chesapeake

931 Centurion Circle, South Chesapeake
$395,000
3 Beds ⋅ 2.1 Baths ⋅ 10628451 MLS
perfect combination of style, space, and low-maintenance living. The first floor features a versatile flex room with backyard access and wooded views, ideal for a 4th bedroom, home office, guest suite, or den. The second floor boasts an open-concept layout with a spacious living area, dining space, and a well-appointed kitchen with island, granite countertops, pantry, and powder room, plus access to a large composite deck overlooking a private, tree-lined setting. The third floor offers three bedrooms, two full baths, and a convenient laundry area. The primary suite includes tray ceilings, a walk-in closet, and a private bath with double sinks and an oversized shower. Enjoy resort-style amenities including pool, clubhouse, fitness center, dog park, dock, pier, beach, and marina access. Conveniently located near Publix, Tidewater Community College, shopping, and dining.

931 Centurion Circle, South Chesapeake

2645 Roundtree Circle, South Chesapeake
$395,000
3 Beds ⋅ 2 Baths ⋅ 10625839 MLS
The original owners built this home in 1984, raised their family here and lovingly updated it over the years. Now moving closer to family, they are passing this well-cared-for home to its next lucky owners. Located in Oak Manor on a quiet dead-end street, this 3BR/2BA ranch at 2645 Roundtree Circle sits on 0.45 acres with 1,516 sqft. of comfortable living space. Updates include kitchen, windows, flooring, roof, HVAC and built-ins and surround sound system in Family Room. Eat-in kitchen features solid surface countertops, center island, stainless appliances and backsplash. Detached 2-car garage/workshop with power for machinery. No HOA! Easy access to interstates, shopping, dining and military bases via I-64 & Military Hwy. Move-in ready!

2645 Roundtree Circle, South Chesapeake

2301 Gates Landing, South Chesapeake
$391,100
3 Beds ⋅ 2 Baths ⋅ 10633101 MLS
Beautifully maintained cul-de-sac home in the highly desired Locks Landing neighborhood of Chesapeake. This move-in ready property offers 3 bedrooms and 2 full baths with thoughtful upgrades throughout. The kitchen features custom Greenwich cabinetry and high-end appliances, with charming coffee bar just off the dining room. The inviting living area includes cozy functional wood-burning fireplace, while the primary suite offers a private ensuite. Enjoy the picturesque garden-like yard with a fully fenced backyard complete with an above ground pool, deck, pergola-perfect for relaxing or entertaining. Additional highlights include parking for up to four vehicles, RV 30 amp electrical hookups, and new HVAC system (2025) and full encapsulation of the crawl space (2026). No HOA and conveniently located near Hampton Roads military bases, shopping, dining and entertainment.

2301 Gates Landing, South Chesapeake

216 Marion Drive, South Chesapeake
$391,000
3 Beds ⋅ 2 Baths ⋅ 10641722 MLS
Welcome to this charming 3-bedroom, 2-bath bungalow ranch style home nestled on a spacious .46 of an acre lot in the heart of Great Bridge! Offering approximately 1,288 square feet of comfortable living space, this well-maintained home combines timeless appeal with modern updates. The inviting kitchen features granite countertops, a convenient pantry, and a cozy breakfast area, creating an inviting space for everyday living. Enjoy your morning coffee on the welcoming front porch or entertain family and friends on the back deck overlooking the large, fully fenced backyard. A standout feature of this property is the large two-story detached workshop with electricity, great for hobbies, a home workshop, or additional storage needs. Supplemental concrete has also been poured to allow for more convenient SUV, boats or recreational vehicle parking. Conveniently located just minutes from shopping, dining, parks, Intra Coastal Waterway and everyday conveniences, this home offers the a balance of peaceful living and accessibility. Don't miss the opportunity to make this Great Bridge gem your next home! Call now before it is gone!

216 Marion Drive, South Chesapeake

716 Baywood Trail, South Chesapeake
$390,000
3 Beds ⋅ 2 Baths ⋅ 10646455 MLS
Beautifully reimagined ranch home with designer-inspired finishes throughout! Offering 1,482 square feet, this exceptional residence features 3 bedrooms, 2 beautifully updated baths, and a versatile bonus room ideal for a home office, playroom, guest space, or hobby room. The stunning kitchen showcases new custom-style cabinetry, elegant granite countertops, and brand-new stainless steel appliances, including a dishwasher, range, microwave, and disposal. Matching granite countertops extend into the bathrooms, which have been tastefully renovated with stylish new tile finishes. Additional upgrades include a new roof, new windows, new HVAC system, new water heater, new interior doors, fresh interior paint, and new flooring throughout. Blending timeless style with modern updates, this turnkey home offers comfort, quality, and exceptional value. Don't miss out, schedule your showing today!

716 Baywood Trail, South Chesapeake

432 Charleston Street, South Chesapeake
$390,000
3 Beds ⋅ 2.1 Baths ⋅ 10644759 MLS
Welcome home to this beautifully maintained townhome in the highly desirable Great Bridge area of Chesapeake! This spacious 3-bedroom, 2.5-bath home offers the perfect blend of comfort, style, and convenience. The open-concept floor plan is filled with natural light and features gleaming wood floors, granite countertops, stainless steel appliances, and crisp white cabinetry. The primary suite boasts a granite vanity and dual shower heads for a spa-like retreat. Pride of ownership shines throughout with a fresh interior paint refresh and a newly installed backyard gravel area, creating a low-maintenance outdoor space perfect for relaxing or entertaining. Complete with an attached garage and driveway parking, this move-in ready home is ideally located just minutes from shopping, dining, top-rated schools, parks, military bases, hospitals, and the area’s beautiful beaches. Don’t miss the opportunity to own this well-cared-for home in one of Chesapeake’s most sought-after communities!

432 Charleston Street, South Chesapeake

1421 Glendale Avenue, South Chesapeake
$390,000
4 Beds ⋅ 2 Baths ⋅ 10644668 MLS
Welcome home to 1421 Glendale Avenue! Designed for effortless living, where quality craftsmanship, modern style & everyday convenience come together in this beautifully updated 4-Bedroom, 2 Bathroom Ranch home w/exceptional indoor & outdoor living spaces in the heart of Chesapeake! The high-end custom eat-in kitchen features abundant cabinetry, granite countertops, stainless steel appliances, washer & dryer, custom tile backsplash & flooring, breakfast bar area that flows seamlessly to the open concept living & dining areas. The spacious primary suite includes a versatile bonus room, ample closets & private ensuite bathroom. Outdoors you'll find beautifully landscaped grounds, a fenced private backyard oasis offering plenty of space to enjoy the covered patio, marshmallows by the fire-pit, beautiful flower gardens, substantial vegetable, herb & fruit gardens…. and don’t miss out on the oversized insulated detached garage/workshop plus storage shed. Call today for your private tour!

1421 Glendale Avenue, South Chesapeake

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

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

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.