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302 Honey Locust Way Way, South Chesapeake
$650,000
4 Beds ⋅ 2.2 Baths ⋅ 10653782 MLS
Former Home-A-Rama award-winning home with character you simply don't find every day. Tucked away on a .43-acre cul-de-sac lot, this 3-story Victorian-style home offers approximately 3,100 sq. ft. of living space and a wrap-around porch. Inside you'll find hardwood floors, generous living and dining spaces, custom details, two fireplaces and two staircases. The gourmet kitchen features quartz countertops, black stainless appliances, custom cabinetry, island and pantry. Spacious bedrooms lead to an impressive primary suite with walk-in closet, ensuite bath and fireplace. A third-level bonus space offers flexibility for an office, study or workout room. Outside, an in-ground saltwater pool, multi-level deck, gazebo, fire pit and expansive backyard create a setting for entertaining or relaxing. A truly unique home ready for its next chapter!

302 Honey Locust Way Way, South Chesapeake

1741 Taft Road, South Chesapeake
$999,999
4 Beds ⋅ 2.1 Baths ⋅ 10653479 MLS
Three wooded acres. A saltwater pool. Five garage bays. Room for the boat, RV and workshop. And no HOA. 1741 Taft Road offers a combination that’s increasingly hard to find in Southern Chesapeake. The approx. 3,700-sq.-ft. home features 4 bedrooms, 2.5 baths and a welcoming wraparound porch. Inside, the kitchen is equipped with matte white Café appliances including a gas range, while the spacious living room centers around a wood-burning fireplace. Upstairs are 4 generously sized bedrooms, including a primary suite with 2 walk-in closets. A finished third floor adds 2 large bonus rooms, creating flexible space for a nursery, home office, gym, studio or private retreat. Outside, an approx. 32,000-gallon saltwater pool and composite deck anchor the backyard, with major pool components updated in 2025–26. A heated 2-car attached garage is joined by a 3-bay detached garage/workshop with propane heat plus mini-split heating and cooling. Covered paved storage accommodates a boat, camper or RV, with a pole barn and additional storage shed adding even more versatility. The acreage continues beyond the rear gate into the woods, where walking trails extend the ways to enjoy the property. Extensive paved parking and a private setting complete a property that offers breathing room without giving up convenient access to Chesapeake.

1741 Taft Road, South Chesapeake

1530 Jolliff Road, West Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10653544 MLS
Ready Soon! Your New Home in Western Branch! Exceptional new construction on a spacious half-acre lot, thoughtfully designed for modern living and outdoor enjoyment. This open-concept floor plan features a desirable first-floor guest suite with a private bath and walk-in closet. The chef-inspired kitchen showcases granite countertops, custom cabinetry, stainless steel appliances, and designer lighting. Luxury vinyl plank flooring flows throughout the first floor and all bathrooms. Enjoy a covered front porch, two-car garage, and rear patio overlooking your private backyard, with plenty of space to add a pool and create your own outdoor oasis. Quality craftsmanship and thoughtful design come together in this highly desirable Western Branch location. Completion in Fall 2026. Don't miss the opportunity to make this exceptional new home yours!

1530 Jolliff Road, West Chesapeake

4704 Mahogany Run, West Chesapeake
$447,340
4 Beds ⋅ 3 Baths ⋅ 10653533 MLS
It's happening as you read this! The final building is under construction at The Retreat at Western Branch. This Lafayette is ready for you to personalize with your choice of finishes and options. Featuring a first-floor primary bedroom, huge island kitchen open to the great room, first-floor office or guest room with full bath, 2-car garage and covered porch. Upstairs you'll find a loft/sitting area plus two bedrooms with a shared bath. This low-maintenance 55+ community features a clubhouse, fitness center, billiards, pool, outdoor grilling area, dog park, community garden, and landscaped grounds. Buy now and make it yours by selecting your finishes and options during construction. Final price will be determined by buyer-selected options and upgrades.

4704 Mahogany Run, West Chesapeake

3708 Riverwood Crescent, South Chesapeake
$775,000
5 Beds ⋅ 2.1 Baths ⋅ 10653033 MLS
Welcome to 3708 Riverwood Crescent! Situated on approx. 3 acres in sought after Chesapeake 23322, this nearly 3,000 sq. ft. home offers space, privacy & extensive updates! Enjoy a private backyard retreat with pool, screened porch & updated deck. Inside features a remodeled kitchen with quartz countertops, mostly stainless steel appliances, soft-close cabinetry, recessed lighting, hardwood & luxury vinyl plank flooring, plus new carpet upstairs, and solar hallway lighting. Updated baths include new countertops, toilets, fixtures, ceramic tile, tub/shower & an enlarged porcelain-tiled primary shower. Major improvements include dual-zone HVAC (2019/2021), 2024 water heater, water softener, encapsulated crawl space with pump & dehumidifier, replaced exterior/garage doors, vinyl windows & 2011 roof with 50-yr warranty. Shed and lawn tractor conveys! A rare combination of acreage, updates, pool & location; come see it!

3708 Riverwood Crescent, South Chesapeake

419 Granada Drive, South Chesapeake
$665,000
4 Beds ⋅ 3 Baths ⋅ 10652967 MLS
This home truly has it all! Welcome to this beautiful 4-bedroom, 3-full-bath home in the highly desirable Las Gaviotas golf course community. Offering 3,371 square feet of thoughtfully designed living space, this home immediately impresses with beautiful flooring and an inviting, open feel. Enjoy peaceful living along a quiet tidal creek from the Elizabeth River, where changing tides, abundant wildlife, and natural beauty create a truly serene backyard setting. Relax on the updated Trex deck and enjoy the peaceful views, or take in the scenery from the inviting sitting room just off the living room, where gorgeous windows bring the beauty of the outdoors inside. The flexible floor plan includes a first-floor bedroom, dedicated home office/gym, and an upstairs bonus room—providing plenty of space for guests, work, hobbies, or entertaining. Numerous recent updates provide peace of mind, including new ductwork in attic and crawlspace (2025), roof and skylight (2024), water heater (2024), Prodigy insulated siding, fascia and rain gutters (2024), Bosch BOVA upstairs HVAC system (2022), Trex decking (2023), first-floor LVP flooring (2021), and crawlspace dehumidifier (2026). With golf-course community living, a peaceful tidal-creek setting, abundant natural light, and an impressive list of updates, this is a home you won’t want to miss.

419 Granada Drive, South Chesapeake

952 Checkerspot Way, South Chesapeake
$685,000
5 Beds ⋅ 2.1 Baths ⋅ 10652920 MLS
Welcome to a home where thoughtful design meets effortless comfort. Beautifully updated with brand-new LVP flooring, this inviting residence is enhanced by an impressive collection of custom upgrades. The primary suite features a California Closets custom system, while the office offers tailored shelving and storage. In the kitchen’s eat-in area, a dedicated dog station and additional pantry provide both style and everyday functionality. Step outside and discover a private backyard backing to peaceful woods, complete with a fire pit—for relaxing or entertaining under the stars. The screened-in porch offers another inviting space to unwind and enjoy your favorite show. With the neighborhood playground just across the street, this home blends privacy, convenience, and thoughtful details in all the right ways. A home this special deserves to be seen!

952 Checkerspot Way, South Chesapeake

2556 Fieldsway Drive, Central Chesapeake
$415,900
3 Beds ⋅ 2.1 Baths ⋅ 10652794 MLS
Welcome to Coleman Farms! This bright and inviting 3-bedroom, 2.5 bath home features a very open living concept with seamless flow between kitchen, living and dining areas. The kitchen offers granite countertops, large pantry, stainless steel appliances and a new dishwasher. Upstairs you'll find 3 spacious bedrooms, including a comfortable primary suite with private bath, plus a convenient laundry room with new washer and dryer. Additional features include custom blinds throughout the home. Enjoy a private patio that backs up to the woods, offering a quiet, peaceful setting. The 2 car garage provides additional storage and parking. The driveway accommodates 2 additional vehicles, plus ample visitor parking. Coleman Farms is a private, tucked-away community that features a clubhouse, fitness center, and pool. Conveniently located near shopping, entertainment and major highways. Super clean and move in ready!

2556 Fieldsway Drive, Central Chesapeake

5 Harbor Watch Drive Unit 405, South Chesapeake
$310,000
3 Beds ⋅ 2 Baths ⋅ 10651901 MLS
Wake up to peaceful water views right from your bedroom! This spacious, well-maintained 3-bedroom, 2-bath condo offers 1,762 square feet per MLS of comfortable, single-level living and low-maintenance convenience. Featuring luxury vinyl plank flooring in the living areas. Large windows and a sliding glass door bring in plenty of natural light. The kitchen offers abundant cabinet space, newer stainless steel appliances, including a wine fridge, and a convenient pantry. The spacious primary suite features a walk-in closet, linen closet, and private bath with a double vanity, soaking tub, and separate stand-up shower. Additional features include newer windows and a sliding glass door, ceramic tile, carpeting, and plenty of storage throughout. Amenities include a pool and clubhouse. Association services also include dock maintenance, water, sewer, and trash. Deeded Boat Slip negotiable with sale

5 Harbor Watch Drive Unit 405, South Chesapeake

2100 Millville Road, South Chesapeake
$650,000
5 Beds ⋅ 2.1 Baths ⋅ 10652716 MLS
Custom 5-bedroom, 2.5-bath Chesapeake home on a huge half-acre lot, currently zoned for Grassfield High School! This beautifully updated home features an open floor plan, pickled oak hardwood floors, quartz countertops, stainless steel appliances, gas range, custom barn doors, and European-inspired lighting and fixtures. The spacious primary suite offers cathedral ceilings, dual closets, and a private deck with peaceful wooded views. The spa-like primary bath features a freestanding soaking tub and custom porcelain-and-glass shower. Outside, enjoy an expansive deck and plenty of room for outdoor living, entertaining, and recreation. If you’ve been searching for a custom Chesapeake home with space, style, updates, and a large lot, this one deserves a closer look. Schedule your tour today!

2100 Millville Road, South Chesapeake

620 Estates Way Unit 120, South Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10652230 MLS
Surrounded by trees, this 2006 townhome-style condo offers a quieter setting with shopping, dining, parks & interstate access close by. The open main level features flexible living spaces anchored by a gas fireplace. The adjoining kitchen offers granite counters, stainless appliances, & an efficient layout open to the living areas. Upstairs are comfortably sized bedrooms, including a spacious primary suite w/ ensuite bath, double sinks, tiled shower & generous storage. Enjoy a shaded rear deck overlooking the wooded setting plus an oversized attached garage. Major updates include a high-efficiency York heat pump/HVAC installed 12/2025 (includes 10 yr parts/3 yr labor warranty) & architectural-shingle roof estimated at 2–5 years old. Pre-list inspection completed 9/2026; report available.

620 Estates Way Unit 120, South Chesapeake

3132 Benefit Road, South Chesapeake
$1,000,000
6 Beds ⋅ 3 Baths ⋅ 10652479 MLS
Open House 9/26 & 9/27 1-3pm 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 serene acreage 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

568 Waters Road, South Chesapeake
$639,000
6 Beds ⋅ 2.1 Baths ⋅ 10652034 MLS
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, making daily life and entertaining feel natural. 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. Convenient to shopping, dining, highways, and Chesapeake amenities, this home brings together function, flexibility, and a location buyers love. Closing cost contribution available with acceptable offer.

568 Waters Road, South Chesapeake

620 Ambrose Street, South Chesapeake
$589,500
4 Beds ⋅ 2.1 Baths ⋅ 10651843 MLS
Beautifully crafted new construction by East Coast Development Group, Inc., a local, award-winning builder, with delivery end of 2026. LVP flooring flows through the first floor, complemented by tiled bathrooms. The primary suite features a luxurious walk-in shower and double vanity, while the large yard offers room to enjoy the outdoors. No HOA! Zoned for Grassfield High School, this home also includes an energy-efficient appliance package and a gourmet kitchen with granite counters, a deep sink, and a spacious island. Enjoy a large pantry, abundant storage, and a full attic. Carpet in all bedrooms adds warmth and comfort. Situated on an established street just off Johnstown Rd, minutes from the heart of the Great Bridge community. Up to $10,000 in closing cost assistance available with use of builder's preferred lender. Don't miss this opportunity. Other lots/plans available.

620 Ambrose Street, South Chesapeake

1204 Murray Drive, South Chesapeake
$769,000
5 Beds ⋅ 3 Baths ⋅ 10651816 MLS
Stunning one-owner home on 3 treed acres in the sought-after Hickory High School district, with easy access to Virginia Beach! Custom hardwood floors and trim/woodwork throughout, brand new carpet, and new luxury vinyl in the rec room off the garage. Main floor is 100% hardwood. 5 bedrooms plus two bonus rooms over the garage — great for a teenage suite or mother-in-law suite. Spacious great room with fireplace, formal dining room, and breakfast area off the kitchen. Remodeled kitchen features granite countertops, double oven, double sink, and a generous pantry. First floor offers a shelved library/home office. Florida room with screens and Andersen windows throughout, plus skylights including one in the primary suite. Newer Trex composite deck and storage building in back. Encapsulated crawlspace w/ sump pump & dehumidifier (JES). Well on-site, city water, septic. HVAC serviced annually. Lots of space to grow in this sturdy home!

1204 Murray Drive, South Chesapeake

641 Ravenwoods Drive, South Chesapeake
$1,519,000
5 Beds ⋅ 4.1 Baths ⋅ 10651679 MLS
Stunning property situated in the heart of Great Bridge on 3 acres! Brand new gourmet kitchen with 6 burner Cosmo range, additional prep sink, new top of the line appliances and custom cabinetry. All new paint, flooring and completely renovated baths and stairwells on first two primary living levels. Bonus third floor complete with full bath, new paint and new flooring! HUGE primary suite complete with fireplace, fantastic walk-in closet and beautiful new bath. The detached 3.5 car garage includes a garage apartment with kitchenette and full bath. New windows, roof, gutters, soffits and pool liner. Absolutely amazing opportunity to secure this gorgeous, move-in ready property. Awesome enclosed patio with hot tub as well as an outdoor kitchen/bar area. This is an entertainer's dream! See it today before it is SOLD!

641 Ravenwoods Drive, South Chesapeake

1853 Rockwood Drive, South Chesapeake
$610,000
4 Beds ⋅ 2.1 Baths ⋅ 10651226 MLS
This well-maintained home features hardwood floors throughout the main living areas. The kitchen includes stainless steel appliances, 42-inch cabinets, quartz countertops, a large deep sink, two pantries, and a spacious island with bar seating. The family-room offers a fireplace, and the dining room features French doors. Upstairs, the primary suite includes a vaulted ceiling and private bath with dual sinks, a custom tiled shower, and a jetted tub. Three additional bedrooms, a full bath with dual vanities, and a laundry room complete the second floor. The sunroom overlooks the fenced backyard and extended patio, providing additional space for outdoor living and entertaining. Exterior recently repainted. Located in the Grassfield school district with convenient access to the expressway, shopping, and dining.

1853 Rockwood Drive, South Chesapeake

2704 Faulkner Drive, West Chesapeake
$278,000
2 Beds ⋅ 2.1 Baths ⋅ 10651066 MLS
Welcome home! This beautifully maintained 2 BR 2.5 bath condo is located in the heart of Western Branch. The open concept main living area offers a spacious and inviting layout, featuring a breakfast bar stylish pendant lighting, and flexible space for entertaining, working or every day living. The gourmet kitchen is designed with functionality in mind, showcasing stainless steel appliances, ample cabinet & counter space, a large pantry, and recessed lighting. Upstairs you'll find 2 generously sized ensuite bedrooms, each w/expansive walk in closets. An additional flex space provides endless possibilities and can be used as a home office, fitness area, nursery, hobby room, or extra storage. Step outside to enjoy the private patio, great for outdoor dining or relaxing, complete with an attached storage shed. Residents also enjoy community amenities, including a swimming pool, cabanas, and exterior building maintenance.There is a reserved parking space just feet from the door

2704 Faulkner Drive, West Chesapeake

1432 Pine Grove Lane, West Chesapeake
$645,500
5 Beds ⋅ 3 Baths ⋅ 10650640 MLS
Over 3,200 sq ft beautifully maintained 5br brick ranch in the heart of Riverbend/ Western Branch area. Situated on a spacious 0.756 acre lot. This multigenerational layout offers 4 generously sized bedrooms on the main level, including a primary suite w/ a stunning custom-modeled bath. The flexible fourth main-level bedroom off the kitchen can easily function as an in-law suite with walk in closet & a full bath conveniently located off the kitchen. The home features three full baths, plus an additional large bd over the garage, for guests, bonus room, or home office. The expansive kitchen opens seamlessly to the family room and showcases stainless steel appliances and granite countertops, great for everyday living & entertaining. Spacious formal living & dining room. Additional highlights include, large laundry room, three-zone HVAC system, gas water heater replaced in 2021, newer gutters & electric fence. Two-car garage & a wonderful backyard w/ tree house complete this rare Riverbend opportunity. NO HOA

1432 Pine Grove Lane, West Chesapeake

705 Creekwood Drive, South Chesapeake
$595,000
5 Beds ⋅ 4 Baths ⋅ 10650611 MLS
This meticulously maintained home in the sought-after Grassfield area of Chesapeake is waiting for you! Featuring 5 bedrooms and 4 full bathrooms, this spacious home offers plenty of room for everyday living and entertaining. The upstairs primary suite provides a relaxing retreat with two closets, a double vanity, stand-up shower, and garden tub. Three additional bedrooms and two full bathrooms complete the upstairs living space. The downstairs bedroom with an en-suite bathroom offers flexibility for guests, an in-law suite, or home office. The well-appointed kitchen features granite countertops, a breakfast bar, and updated appliances. The spacious living room is warmed by a gas fireplace, creating a cozy gathering space. A bright sunroom offers peaceful views of the wooded backyard, where mature trees create a private and tranquil setting. Don't miss the opportunity to make this home in the desirable Grassfield area your next home! Come see today!

705 Creekwood Drive, South Chesapeake

2907 Seven Eleven Road, South Chesapeake
$799,900
4 Beds ⋅ 2.1 Baths ⋅ 10650499 MLS
The Aspen Barndominium! Customize this 4b/ 2.5b barndo with your style, colors and finishes with the builder. Stunning Covered Front Porch leads to the Open Great Room designed with 18ft vaulted ceiling for the perfect open Living, Dining and Kitchen space. Kitchen with Stainless Steel Appliances, granite counters, tile backsplash, and walk-in pantry. Large Primary with huge walk-in closet and Spa-like Bathroom. Large laundry room, mudroom with lots of storage space and wash area. Bedrooms 2, 3, 4 share a bathroom with rec/bonus space. Best spot may just be the huge covered back porch with lovely nature views and access from the kitchen great room. Pics of previously built Aspen and may show upgrades. Listing price includes Turn-Key Cost to build with a Construction Loan including cost of Land, Well, Septic, and Land Development.

2907 Seven Eleven Road, South Chesapeake

MM Raccoon (Reba On 16-3) Trail, South Chesapeake
$755,166
3 Beds ⋅ 2.1 Baths ⋅ 10650490 MLS
Welcome home to the Reba floor plan by Kirbor Homes, situated on a picturesque 1+ acre cul-de-sac lot in Sanderson Estates! This 3-bedroom home offers a tranquil backdrop featuring scenic views of a neighboring pond and mature trees. Inside, enjoy a functional design complete with a spacious main-level layout with a spacious kitchen, breakfast area, and great room, along with an oversized 2-car garage with plenty of extra storage space. Low-maintenance living is made simple with a low HOA dedicated solely to community amenity maintenance. Great location just minutes from shopping, restaurants, and easy access to roadways to all areas of Coastal VA and NC. Serene views and room to spread out—schedule your consultation today to personalize your home details!

MM Raccoon (Reba On 16-3) Trail, South Chesapeake

816 Poquoson Crossing, South Chesapeake
$688,900
5 Beds ⋅ 3 Baths ⋅ 10650242 MLS
Proudly offered by its original owner, this beautifully maintained 5-bedroom, 3 bathroom home is a rare opportunity in one of the area's most desired neighborhoods. The thoughtfully designed floor plan features a spacious downstairs bedroom and full bath, ideal for guest or multi-generational living along with a Great room, well-appointed kitchen, dining room, and flex room. Upstairs you will find 4 additional generous sized bedrooms, including the primary suite with a beautifully updated bathroom and large closet. Enjoy gathering with family and friends in the inviting family room complete with a built-in bar. Start your mornings on the welcoming front porch and unwind in the evenings on the spacious back patio, perfect for outdoor dining, entertaining, or simply relaxing. Find out why Warrington Hall is one of the most desired communities with all of its amenities including: pool, playgrounds, ball fields, and tennis courts.

816 Poquoson Crossing, 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.