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620 Estates Way Unit 120, South Chesapeake
$365,000
3 Beds ⋅ 2.1 Baths ⋅ 10661737 MLS
Enjoy easy, low-maintenance living on a quiet street with peaceful wooded views in Riverwalk. This 3-bedroom, 2.5-bath townhome-style condo offers 1,831 sq. ft. and a thoughtfully designed floor plan with no wasted space. The open main level connects inviting living and dining areas, a gas fireplace, and a kitchen with granite counters, stainless steel appliances and a gas range. Upstairs, a spacious primary suite features double sinks, a tiled shower and a walk-in closet. A versatile loft adds room for work or relaxation, while the second-floor laundry room keeps everyday chores convenient. Unwind on the shaded rear deck overlooking the trees, and enjoy the storage and convenience of an oversized attached garage. High-efficiency York HVAC installed Dec. 2025. Condo fee includes master insurance, exterior/grounds maintenance and trash pickup. Shopping, dining, parks and interstate access are nearby. Pre-list inspection available.

620 Estates Way Unit 120, South Chesapeake

408 Brandon Way, South Chesapeake
$549,900
5 Beds ⋅ 3 Baths ⋅ 10661712 MLS
Welcome home to this immaculate meticulously maintained original owner home in sought after Clearfield Estates. Numerous improvements gas water tank 10/26, LG Refrigerator 5/26, dishwasher 3/26, windows 12/25, roof 30-year architectural 10/23, AC 2013. Triple French patio door looks out to expansive private .30 acre back yard. First floor guest bedroom with full bath, first floor features Brazilian engineered wood floors, open concept with cozy gas fireplace, 4 additional spacious second floor bedrooms including a massive 14.5 X 28 FROG with walk in attic & built ins great for entertaining! Spacious primary features a cathedral ceiling large walk in closet, duel vanities and jetted tub. Central Greenbrier location with easy commute to multiple bases, VB and Norfolk. Sq ft per tax record

408 Brandon Way, South Chesapeake

2500 Evans Lane, South Chesapeake
$1,250,000
4 Beds ⋅ 3.2 Baths ⋅ 10661534 MLS
A truly one-of-a-kind custom-built residence, where exceptional craftsmanship, distinctive architectural details and an extraordinary setting come together in the sought-after Hunters Ridge neighborhood. From the stunning stonework and graceful archways to the custom solid wood and glass doors, every detail reflects a level of character and design rarely found. The impressive primary suite offers a beautiful retreat overlooking the private woods. The tranquil primary bath provides the perfect setting to unwind and recharge.An exceptional feature of this home is the attached in-law suite, offering its own private entrance, garage, full kitchen, one bedroom, 1.5 bathrooms, dedicated washer/dryer and abundant storage. This thoughtfully designed space offers versatility without sacrificing privacy.Tucked away at the end of a cul-de-sac and backing to private wooded views, the property offers a peaceful sense of seclusion while remaining approximately 15 minutes from everyday conveniences

2500 Evans Lane, South Chesapeake

810 Royal Grove Court, South Chesapeake
$354,900
2 Beds ⋅ 2.1 Baths ⋅ 10661637 MLS
Stunning townhome in the sought-after Riverwalk community! Nestled on a quiet-cul-de-sac, this meticulously maintained home features a bright open floor plan with abundant natural light. The eat-in kitchen offers Stainless Steel appliances, pantry, ample cabinetry, generous counter space, and a coffee bar. Gleaming hardwood floors flow throughout the main level and stairs. All window treatments & all appliances convey. Spacious dining room and Great Room with a cozy gas fireplace. Upstairs, both Bedrooms feature en-suite baths, including a large primary suite with walk in shower and Jetted tub. Upgraded carpet upstairs. Private fenced-in large backyard- covered patio and direct access to trails. 2024 Gas Furnace. Tankless water heater. LeafGuard® gutters. Attached Garage, ample storage including attic. Oversized driveway for up to 4 vehicles. ADT® security system throughout home. Amenities include front yard maintenance, trash pickup, Walking trails, & playgrounds. Central location.

810 Royal Grove Court, South Chesapeake

568 Waters Road, South Chesapeake
$600,000
6 Beds ⋅ 2.1 Baths ⋅ 10661261 MLS
Motivated seller! This home offers an assumable FHA loan at 2.75% for a qualified buyer, and the seller is willing to contribute toward closing costs with an acceptable offer. Located in Chesapeake’s sought-after Grassfield school district, this freshly painted, move-in ready home offers space, flexibility, and room to grow. The open floor plan centers around a spacious kitchen with generous cabinet and counter space, pantry storage, and an easy connection to the main living areas. With multiple finished areas across three levels, the layout works well for multigenerational living, long-term guests, remote work, hobbies, a media room, playroom, or additional bedrooms. The third floor was expanded in 2021 to include two finished rooms, giving buyers even more space. Outside, the large fully fenced backyard and spacious deck are ready for cookouts, pets, play, relaxing evenings, and weekend gatherings. An expanded extra-wide driveway and EV charger add everyday convenience.

568 Waters Road, South Chesapeake

925 Cranberry Drive Unit 70, South Chesapeake
$514,900
4 Beds ⋅ 2.1 Baths ⋅ 10661392 MLS
Welcome to this beautifully maintained condo in one of Chesapeake's most desirable 55+ communities where, comfort and convenience come together in a park-like setting. Surrounded by mature landscaping, a scenic pond, and inviting seating area with a fireplace, this neighborhood offers a relaxed lifestyle with thoughtfully designed community spaces. Inside, this spacious home offers four bedrooms and two and a half bathrooms with a layout designed for both everyday living and entertainment. The primary suite provides a comfortable retreat with generous space and privacy. An in-unit elevator adds exceptional convenience and accessibility between levels. Call today for your private tour. Brand new heating and cooling systems installed 11/2026. Closing cost assistance available with acceptable offer!

925 Cranberry Drive Unit 70, South Chesapeake

3708 Riverwood Crescent, South Chesapeake
$750,000
5 Beds ⋅ 2.1 Baths ⋅ 10661394 MLS
Set on approximately 3 acres in Chesapeake’s Riverwood neighborhood (23322), 3708 Riverwood Crescent offers nearly 3,000 sq ft with 5 bedrooms, 2.5 baths, and a private, wooded backyard with a pool, screened porch, and updated deck. The remodeled kitchen features quartz countertops, soft-close cabinetry, recessed lighting, and mostly stainless steel appliances. Inside you’ll also find hardwood and luxury vinyl plank floors, new upstairs carpet, and updated baths with an enlarged porcelain-tiled primary shower. Major updates include dual-zone HVAC (2019/2021), a 2024 water heater, a water softener, an encapsulated crawl space with pump and dehumidifier (transferrable warranty), and replaced exterior and garage doors. The vinyl windows and screens have a transferable warranty, and the roof was replaced in 2011 with a 50-year warranty. The septic tank was recently pumped, and the shed and lawn tractor convey. Seller is willing to offer allowance for painting foyer and dining room.

3708 Riverwood Crescent, South Chesapeake

952 Checkerspot Way, South Chesapeake
$679,000
5 Beds ⋅ 2.1 Baths ⋅ 10661245 MLS
Come see all the thoughtful details that make this home truly special! Featuring brand-new LVP flooring and an impressive array of custom upgrades, this home blends style, comfort, and everyday convenience. The primary suite boasts a custom California Closets system, while the office features beautifully tailored shelving and storage. The kitchen’s eat-in area offers a clever built-in dog station and additional pantry space. Step outside to your own peaceful retreat, where a private backyard backs to the woods and features a fire pit for relaxing or entertaining. The screened-in porch provides yet another inviting space to unwind and catch your favorite show. With the neighborhood playground just across the street, this home offers the perfect blend of privacy, functionality, and lifestyle. Don't just take our word for it—come see everything this home has to offer. You won't want to miss it!

952 Checkerspot Way, South Chesapeake

3132 Benefit Road, South Chesapeake
$975,000
6 Beds ⋅ 3 Baths ⋅ 10661286 MLS
Modern Farmhouse Charm Meets Turnkey Living in Desirable Chesapeake! Discover the modern farmhouse you’ve been dreaming of, where peaceful country living meets thoughtful, top-to-bottom renovation. Set on 3 Serene acres with panoramic wooded views. It embraces the natural surroundings. This beautifully refreshed home is ideal for extended family/multi generational living. Natural light fills the home, showcasing new flooring, fresh interior paint, updated lighting, and beautifully renovated bathrooms. The completely redesigned custom kitchen is the heart of the home, featuring quartz countertops, ceramic backsplash, abundant prep space, an inviting eat-in area and a KitchenAid appliance suite, ideal for everyday living and entertaining. The expansive living area offers plenty of room to gather, while the renovated wood-burning fireplace creates a cozy focal point with a new firebox, flue, chimney cap, and Buck Stove-style insert. Step onto the Trex deck with PVC railing and enjoy peaceful wooded views from the living space, primary suite or deck. The primary suite is a true retreat, featuring a custom-tiled shower with built-in bench and generous niche, deep soaking tub, double vanity and ceramic tile flooring. The expansive custom closet with built ins provides all the space you have been longing for. Additional improvements include an encapsulated crawlspace with dehumidifier, new septic system designed for 10 occupants, finished room over the garage with generous storage, updated downstairs ductwork, new interior and exterior doors and hardware, new lighting throughout, and a freshly graded crushed-aggregate driveway. The painted brick exterior adds a fresh, modern look while preserving brick’s timeless durability and character. Best of all, the home features a highly energy-efficient geothermal HVAC system. From the crawlspace to the exterior, virtually nothing has been overlooked. Renovated by New Again Houses VB. It offers the feel of quality new construction without sacrificing character, space or setting. See it today!

3132 Benefit Road, South Chesapeake

601 Margaret Drive, South Chesapeake
$650,000
3 Beds ⋅ 2 Baths ⋅ 10661086 MLS
Do not miss this one! Completely updated home has an open floor plan with a beautiful kitchen and large island. Both bathrooms have new fixtures and tile. The room over the garage has been finished and can be used as a flex room. The large pool is only a few years old and has an expansive concrete patio and a gazebo for entertaining. Besides the 2 car garage there is a 15' x 20' shed with power for storage or workshop and a chicken coop for homesteading. The side yard is completely cleared with enough room for a soccer field or could be fenced in for animals. The backyard is wooded for privacy and wildlife. The neighborhood is sought after due to the lot sizes and located in the desirable Hickory school zone. You will have the feeling of living in the country while still centrally located between Great Bridge (Chesapeake) and Landstown (Virginia Beach) shopping. The square footage is approximate as the tax records do not include the FROG. Agent is related to seller.

601 Margaret Drive, South Chesapeake

641 Ravenwoods Drive, South Chesapeake
$1,499,000
6 Beds ⋅ 4.1 Baths ⋅ 10660835 MLS
Discover exceptional space, privacy, & luxury in this all brick estate situated on 3 private acres in Great Bridge with no HOA. 6 bedrooms, 4.5 baths in the main house + a 1,200 sq ft apartment above the detached garage for an impressive total 6,848 sq ft. This home has been thoughtfully updated throughout featuring a newer roof, windows, pool liner, kitchen with top of the line appliances, & bathrooms, fresh paint, & new flooring. The expansive primary suite is a true retreat, featuring its own fireplace, a beautifully renovated luxury bathroom, & an oversized walk-in closet with custom cabinetry. The outdoor living space is equally impressive, complete with an outdoor kitchen & pool + a 4 season room with hot tub. Car enthusiasts & those longing for extra space will appreciate the attached 2 car garage & detached 4 car garage with a separate apartment above featuring a full bathroom and kitchenette ideal for guests, multigenerational living, or additional flexibility. All of this in highly desirable school districts, offering the perfect combination of space, privacy, convenience, and upscale living!

641 Ravenwoods Drive, South Chesapeake

5013 Oriole Drive, West Chesapeake
$585,000
4 Beds ⋅ 2.1 Baths ⋅ 10660763 MLS
Welcome to Jolliff Woods! Step into an impressive foyer with gleaming engineered hardwood floors. The remodeled kitchen features rich cherry cabinetry, granite countertops, mosaic backsplash, beautiful chandelier, a spacious island overlooking the backyard. Enjoy a cozy family room with a gas fireplace, elegant formal living and dining areas, an updated powder room, and a separate laundry room. Upstairs, four generously sized bedrooms provide plenty of space. 5.75% INTEREST RATE FOR QUALIFIED BUYERS! MAJOR UPDATES: Roof (2022), HVAC (2016), engineered hardwood floors (2017), deck (2017), kitchen and half bath (2018), and water heater (2019). With so many updates already completed, this home is ready for its next owner! Don't miss this opportunity—schedule your private tour today!

5013 Oriole Drive, West Chesapeake

1228 Destiny Way, South Chesapeake
$469,900
3 Beds ⋅ 2.1 Baths ⋅ 10660882 MLS
Welcome to this spacious 3-bedroom, 2.5-bath home offering a versatile floor plan designed for both functionality and entertaining! The main level features 9-foot ceilings, two generous living areas, a dedicated dining space, and a cozy natural gas fireplace. The kitchen offers luxurious granite countertops and stainless steel appliances. Upstairs, the primary suite offers a spacious walk-in closet, dual-sink vanity, and relaxing jetted tub. To top it off, the laundry is located on the second-floor! Attached two-car garage, with lots of space for storage. Go outside to a fully fenced backyard featuring a composite deck overlooking a peaceful wooded setting, great for relaxing. Whether you're enjoying your morning coffee on the covered front porch or hosting friends out back, this home has plenty to offer! Conveniently located near shopping, dining, and major interstates. Schedule your private showing today!

1228 Destiny Way, South Chesapeake

4702 Mahogany Run, West Chesapeake
$457,023
4 Beds ⋅ 3 Baths ⋅ 10660350 MLS
The final building is under construction at The Retreat at Western Branch! The Lafayette floorplan delivers spacious, stylish living with an estimated March/April 2027 completion. The thoughtfully designed first-floor features a primary suite, guest bedroom or office with full bath, an impressive island kitchen flowing seamlessly into the great room and dining area. 2-car garage and covered porch, too! Upstairs, discover an expansive loft, two additional bedrooms, a full bath, and extra storage. All in a low-maintenance 55+ condo community with resort-style amenities, including a clubhouse with fitness center and billiards, swimming pool, outdoor grilling area, dog park, community garden, and beautifully landscaped grounds. Don't miss this exciting opportunity to make the Lafayette your next home!

4702 Mahogany Run, West Chesapeake

5037 Annapolis Drive, West Chesapeake
$579,000
4 Beds ⋅ 2 Baths ⋅ 10660299 MLS
Enjoy sought-after ranch-style living in this like-new, two-year-old Dogwood model in Estates at Joliff Landing! Located in Chesapeake's Western Branch area, this popular floor plan offers the convenience of first-floor living, with every room except the finished room over the garage on the main level. Two bedroom suites provide added flexibility, including one with a dual-entry bathroom accessible from the hallway. The upstairs bonus room offers space for a home office, media room, or guest retreat. Step outside to an oversized, fenced backyard with wooded views, a storage shed, and plenty of room to relax or entertain. Community amenities include a clubhouse, fitness room, playgrounds, and pool. Convenient to shopping, dining, military bases, and major interstates, this beautifully maintained home combines like-new appeal with an established neighborhood setting.

5037 Annapolis Drive, West Chesapeake

891 Bells Mill Road, South Chesapeake
$525,000
4 Beds ⋅ 3.1 Baths ⋅ 10660202 MLS
Welcome Home! Privacy, functionality, and convenience come together in this exceptional Grassfield property! Set back from the street along a private driveway, this nearly one-acre property is surrounded by mature woods and lush greenery. Inside, fresh paint and a flexible floor plan offer something for everyone. A rare find, the home features two distinct main-level suites, including an in-law suite with its own living room, great for multi-generational living, extended guests, a fifth bedroom, or home office. The primary bathroom features live-edge wood countertops, dual showerheads, and a custom walk-in closet system. Outside, enjoy a storage shed, chicken coop, separate hookups for a future pool and hot tub, and a massive detached two-car workshop/garage with carport and RV hookup. Over $17,000 in crawlspace work has been completed, and a survey is available in the listing documents. A truly unique Grassfield property offering flexibility and room to make it your own!

891 Bells Mill Road, South Chesapeake

1605 Mary Lou Lane, South Chesapeake
$475,000
3 Beds ⋅ 2.1 Baths ⋅ 10659685 MLS
Welcome to 1605 Mary Lou Lane in Cardinal Meadows! Built in 2022, this beautifully maintained condo feels brand new, with new carpet throughout and nearly 2,300 sq. ft. of stylish, low-maintenance living. The bright, open main level features high ceilings and a gorgeous kitchen with upgraded cabinetry and quartz countertops. A builder upgrade provides a larger first-floor primary suite and upstairs bedrooms than most homes in the community! The primary suite features a dual-vanity bath and walk-in closet. Upstairs offers a versatile loft, two bedrooms with walk-in closets, a full bath, and walk-in storage with potential for future finished space. Enjoy your private oasis with a newly fenced backyard backing to peaceful woods. Community amenities include a pavilion with grill, splash pad, playground, dog park, and walking trails. Conveniently located near Grassfield schools, shopping, and major interstates. Move-in ready! 1% towards closing cost is being offer to buyer if they use the Listing Edge program.

1605 Mary Lou Lane, South Chesapeake

1620 Sandy Pines Way, West Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10659944 MLS
OVER AN ACRE IN SANDY PINES—FULLY ENCLOSED BY A NEWER WOOD FENCE! Set on an expansive lot of approximately 1.10 acres, with newer wood fencing enclosing the entire property, this traditional two story home offers a standout amount of outdoor space. With approximately 1,628 square feet, 3 bedrooms, and 2.5 baths, the home pairs a generous setting with a practical layout. Enjoy a wood burning fireplace, a kitchen with a breakfast area and pantry, and a primary bedroom with an en suite bath. Walk in closets, walk in attic space, and an attached one car garage provide convenient storage. Situated on a cul-de-sac with driveway parking and 2 storage sheds, this property offers space inside and out, with the impressive fenced lot taking center stage!

1620 Sandy Pines Way, West Chesapeake

4317 Whitfield Lane, Central Chesapeake
$393,000
4 Beds ⋅ 3.1 Baths ⋅ 10659518 MLS
Welcome home to this beautifully updated, newer three-story condo! This move-in-ready gem features fresh paint throughout, new flooring and carpeting, newly installed ceiling fans, and stylish board-and-batten wainscoting. The open-concept design showcases soaring ceilings, recessed lighting, and a gourmet kitchen equipped with a full suite of appliances, "AS IS". Sliding glass doors lead to a private balcony, perfect for morning coffee or relaxing at the end of the day.The first-floor bedroom with an en-suite bathroom offers exceptional flexibility as a guest suite, home office, or additional living space. Enjoy community amenities, including a pool and playground, along with the added benefit of no flood insurance required! Don't miss this opportunity to own a stylish, low-maintenance home that blends comfort, convenience, and modern appeal!

4317 Whitfield Lane, Central Chesapeake

401 Truitt Road, West Chesapeake
$385,000
3 Beds ⋅ 2 Baths ⋅ 10659959 MLS
Enjoy a country feel on a 1.86-acre corner lot in Bowers Hill! This 3-bedroom, 2-bath ranch-style home offers approximately 1,659 square feet, a screened front porch, and a spacious kitchen with ample cabinetry and an island with cooktop and seating. A separate dining room, wood floors, first-floor primary bedroom with private bath, and utility room add to the layout. Upstairs space provides additional storage. Outside, you'll find mature trees, a detached one-car garage, separate storage shed, covered workspace, and a partially fenced side yard. The septic tank is approximately 2.5 years old. No HOA, with convenient access to I-664, I-64, and Route 58. Bring your ideas and make this property your own!

401 Truitt Road, West 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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