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916 W Saint Brides Road Unit W, South Chesapeake
$850,000
6 Beds ⋅ 4 Baths ⋅ 10635980 MLS
Enjoy peaceful country living in this spacious 6-bedroom home on 3 acres with modern updates and room to spread out. Oak hardwood floors flow throughout the main level, which features a formal dining room and an open kitchen with stainless steel appliances, a center island, and a coffee station overlooking the great room with an electric fireplace. The first floor also has a bedroom and a full bath, which could make a great guest room or a dedicated home office. Upstairs, there are 4 generously sized bedrooms, two full bathrooms, plus a finished room over the garage with a private (3rd) full bath, perfect as a media room, guest suite, (6th Bedroom), or playroom. Outside, enjoy an above-ground pool (two years old) with deck, mature fig, blueberry, cherry, and mulberry trees, 3 established chicken coops with 10 hens producing a half dozen eggs a day. There is also a 23x15 workshop, and wide-open backyard views that complete the country lifestyle.

916 W Saint Brides Road Unit W, South Chesapeake

3511 Elaina Way, West Chesapeake
$449,900
3 Beds ⋅ 2.1 Baths ⋅ 10635860 MLS
Move-in ready end-unit Nansemond in the 55+ community of The Retreat at Western Branch. This home presents a great value opportunity with an open layout designed for easy living. The kitchen sits at the heart of the home, featuring bar seating, a walk-in pantry, and convenient access to the living and dining areas. The first floor features a spacious primary suite, while the second floor includes two additional bedrooms, a loft, guest bath, and walk-in attic for added storage. Enjoy outdoor living with a covered rear porch overlooking the wooded backdrop. Additional highlights include a two-car garage and low-maintenance living. Community amenities include a clubhouse, fitness center, billiards room, outdoor kitchen, dog park, community garden, and landscaped grounds. Limited homes remaining.

3511 Elaina Way, West Chesapeake

520 Dunning Lane, South Chesapeake
$535,000
3 Beds ⋅ 2.1 Baths ⋅ 10635653 MLS
Prepare to fall in love with this Elegant and meticulously maintained gem located in the gated 55+ resort style community of Eagle Pointe in Southern Chesapeake. Sitting on a premium home site with water views and no neighbors behind you, you will be impressed with the spacious and flowing Hamilton Floorplan. This lovely Home boasts a vaulted Great Room with gas fireplace and an Eat in Kitchen that opens to the bright and sunny Florida Room that offers peaceful and tranquil water views. Additional Details: Primary Suite with jetted tub and separate step in tile surround shower, 2 nice sized secondary bedrooms with ceiling fans, 2nd floor Loft overlooking the 1st floor, Formal Dining Room, lots of storage space, blinds throughout, central vacuum, patio, and a 2 car attached garage with opener and work sink. Eagle Pointe Bay Club amenities include a heated indoor pool and hot tub, outdoor pool, fitness center, billiards room, game room, library, catering kitchen, and celebration room.

520 Dunning Lane, 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

1390 Sebastian Court, South Chesapeake
$799,900
5 Beds ⋅ 4 Baths ⋅ 10634982 MLS
The Macon Model at Stoney Creek by Wetherington Homes blends refined design, luxury finishes, and modern functionality in a beautifully crafted open-concept layout. Gorgeous hardwood floors flow throughout the home, creating warmth and timeless sophistication. The chef-inspired kitchen is the heart of the home, featuring expansive prep space, a Butlers pantry, abundant cabinetry, high-end appliances, wine fridge, and a large island ideal fo rentertaining! Seamlessly connected dining and living spaces offer effortless flow for everyday living and hosting alike. The spacious owner's suite provides a peaceful retreat with a spa-inspired bath and generous closet space. Secondary bedrooms plus versatile loft space offer flexibility for guests, office space or additional living needs. Exceptional craftsmanship, thoughtful storage solutions, and elevated details throughout make this stunning MOVE-IN READY home truly stand out!

1390 Sebastian Court, South Chesapeake

961 Speight Lyons Loop, South Chesapeake
$600,000
4 Beds ⋅ 2.1 Baths ⋅ 10634733 MLS
Located in the sought-after Grassfield High School District, this beautifully maintained 4BR, 2.5BA Chesapeake home offers the warmth of southern charm, the confidence of major updates, and the comfort of everyday living. Relax on the wraparound front porch or enjoy the backyard deck with wooded privacy. Inside features engineered hardwood floors, spacious family room with wood-burning fireplace and built-ins, formal dining room, and flexible front room for office or playroom. The updated eat-in kitchen opens to the family room and is a chef’s delight with generous prep space, island, pantry storage, and ample cabinetry. Upstairs includes spacious FROG, dual staircase, generous bedrooms, and primary suite with walk-in closet and dual vanity. Major updates include roof (’24), crawlspace encapsulation (’20), fence (’20), water heater (’20), porch railing/post wrap (’23), garage opener (’23), HVAC (’14), and first-floor furnace (’26). Near dining, shopping, and interstates. Move-in ready!

961 Speight Lyons Loop, South Chesapeake

504 Sydenham Boulevard, South Chesapeake
$580,000
4 Beds ⋅ 2.1 Baths ⋅ 10634574 MLS
Beautifully redone and move in ready, this home blends updated finishes with functional living throughout. The first floor features durable LVP flooring and a recently renovated kitchen with quartz countertops, open shelving, farmhouse sink, LG stainless steel appliances, and a spacious walk in pantry. Custom trim details, shiplap accents, wainscoting, and dining room molding add character and charm throughout the home. Bathrooms have also been recently updated for a fresh, modern feel. Upstairs offers generously sized bedrooms with plenty of space to spread out. Enjoy the backyard oasis featuring a saltwater pool, pergola, playhouse, a chicken coop, and recently expanded concrete patio space perfect for entertaining and relaxing. Conveniently located near Edinburgh Shopping Center, grocery stores, dining, and everyday conveniences. An assumable loan with a rare 2.99% interest rate may also be available for qualified buyers.

504 Sydenham Boulevard, South Chesapeake

317 Sawyers Mill Crossing Crossing, South Chesapeake
$520,000
4 Beds ⋅ 2.1 Baths ⋅ 10634685 MLS
Welcome to 317 Sawyers Mill Crossing- where everyday living feels effortless. Imagine hosting holiday dinners that flow seamlessly from the dining room to the kitchen, enjoying slow mornings in the breakfast area, and gathering with friends in the living room before heading outside for summer barbecues under not one, but two pergolas on the spacious deck. Situated on a nicely sized lot in Chesapeake’s sought-after Grassfield school district, this well-maintained home offers 4 bedrooms, 2 full and 1 half bath, and 2,710 sq ft of comfortable living space. The first-floor primary suite feels like its own retreat with a luxurious walk-in shower, dual vanities, and a spacious walk-in closet. Complete with granite countertops, a spacious room over the garage, a 2-car garage, backyard storage shed, and neighborhood amenities including a pool, clubhouse, playground, and easy interstate access.This home offers the lifestyle today’s buyers are looking for. Seller open to $5k credit with full price offer.

317 Sawyers Mill Crossing Crossing, South Chesapeake

1616 Whittamore Road, South Chesapeake
$460,000
4 Beds ⋅ 2.1 Baths ⋅ 10633922 MLS
Enjoy the peaceful feel of country living without sacrificing city convenience. Tucked away in a quiet setting yet minutes from shopping, dining, and major routes, this home offers the space and lifestyle you’ve been looking for. Located in the highly desired Hickory School district near Battlefield Golf Club and Fentress Airfield. The open layout features spacious living and dining areas flowing into a large kitchen with granite countertops and stainless steel appliances. The primary suite offers a large bedroom, walk-in closet, and bath with double sinks, jetted tub, and separate shower. Secondary bedrooms are generously sized with walk-in closets. Enjoy the large fenced backyard complete with a playset that conveys and spacious shed, perfect for entertaining, relaxing evenings, pets, and play.

1616 Whittamore Road, South Chesapeake

4162 Reid Street, Central Chesapeake
$290,000
3 Beds ⋅ 2 Baths ⋅ 10633777 MLS
This adorable ranch home is move-in ready and has been professionally renovated from top to bottom. The architectural roof adds exceptional curb appeal, and quality craftsmanship is evident throughout the home. Conveniently located near schools, shopping, and neighborhood amenities. Fresh interior paint and carpet, stylish knockdown wall finish adds a modern touch throughout. The spacious layout includes a breezeway connecting the family room to the kitchen, which features updated appliances, including a refrigerator with ice maker and water dispenser, custom granite countertops, and ceramic tile flooring. Large utility/laundry room, spacious walk-in closet in the primary bedroom, custom-designed primary bathroom, beautifully updated hall bathroom, premium 18mm laminate flooring throughout main living areas. Large fenced backyard perfect for entertaining with installed deck and hot tub. This beautifully updated home is ready for its new owner!

4162 Reid Street, Central Chesapeake

908 Wheatfield Way, South Chesapeake
$648,000
4 Beds ⋅ 2.1 Baths ⋅ 10633581 MLS
Welcome to this beautifully maintained home ideally positioned along the protected Chesapeake Arboretum, offering 48 acres of scenic trails, natural beauty, and peaceful backyard views. Thoughtful updates include hardwood stairs, Anderson windows on the east/south (2025) side, gutter guards, and a new water heater, along with a roof (2012), 3-zone HVAC (2010), and luxury vinyl plank/carpet (2018). The driveway has been extended with added concrete, along with a newly added concrete back patio. The converted garage provides flexible space perfect for a game room, guest suite, or media area. Step outside to your private oasis featuring a saltwater pool, steps, safety cover, pump, and transferable warranties. Entertain year-round on the spacious patio with built-in lighting, pergola and beautifully landscaped yard designed for both relaxation and gatherings.

908 Wheatfield Way, South Chesapeake

1456 Branchview Way, West Chesapeake
$515,000
4 Beds ⋅ 2.1 Baths ⋅ 10633441 MLS
Located in a quiet and well-established neighborhood, 1456 Branchview Way offers comfortable living with a functional layout ideal for everyday life. This inviting home features spacious living areas filled with natural light, creating a warm and welcoming atmosphere. The kitchen provides ample cabinet and counter space, making it perfect for both daily meals and entertaining. Bedrooms are generously sized, offering flexibility for rest, work, or guests. The backyard provides a great space for relaxing, outdoor activities, or future customization. Conveniently situated near shopping, dining, schools, and major roadways, this home combines suburban comfort with easy access to local amenities. A wonderful opportunity to enjoy peaceful living in Chesapeake.

1456 Branchview Way, West Chesapeake

4335 Whitfield Lane Unit A, Central Chesapeake
$375,000
4 Beds ⋅ 3.1 Baths ⋅ 10632166 MLS
Stunning, highly updated end-unit condo in Reunion Condominiums offering 2,334 sq ft of stylish living space across three spacious levels! This modern home features 4 bedrooms, 3 full baths, and 1 half bath, including two luxurious primary suites with private ensuites—one on the first floor, great for guests or in-laws, and another on the third floor. The bright open-concept main level showcases a spacious living, dining, and kitchen area centered around a large island with bar seating. Step onto the oversized balcony and enjoy peaceful wooded views. Upgrades include modern fixtures, LVP/vinyl flooring, tankless water heater, security system, and hard-wired sound system. Enjoy a 1-car garage, driveway parking for two, large side yard, and ultra-low condo dues. Centrally located near shopping, dining, entertainment, military bases, and more!

4335 Whitfield Lane Unit A, Central Chesapeake

3029 Crossings Drive, West Chesapeake
$560,000
5 Beds ⋅ 3.1 Baths ⋅ 10630413 MLS
Well-maintained home on a corner lot in the heart of Western Branch. This centrally located property showcases a L-shaped Grecian-style pool and offers 5 spacious bedrooms and 3.5 bathrooms, including 2 ensuites. The layout is ideal for multi-generational living, with a primary ensuite on each floor. The 1st floor suite serves perfectly as an in-law suite, featuring a separate entrance and dry bar, while both suites include jetted tubs and expansive walk-in closets. The 2nd-floor primary suite adds a touch of warmth with a gas fireplace and a generous bathroom w/dual sinks. The open and airy main level is designed for both everyday living and gatherings, offering 2 large living areas, a dining room, a well-equipped eat-in kitchen, vaulted ceilings with skylights, and a cozy gas fireplace. Step outside to your private pool oasis that elevates the outdoor experience, creating a serene backyard retreat ideal for both relaxation and entertaining. Don't forget about the neighborhood park!

3029 Crossings Drive, West Chesapeake

4209 Stonebridge Landing, West Chesapeake
$484,699
4 Beds ⋅ 2.1 Baths ⋅ 10631007 MLS
Beautifully renovated home in the highly sought-after Stonebridge neighborhood of Western Branch, featuring major grades including new roof '25 and HVAC system '24 for peace of mind. The previous owners lovingly cared for this home for 23 years. The move-in-ready interior features new luxury vinyl plank flooring throughout the first floor, including the kitchen and foyer, complemented by newly refinished hardwood floors throughout the remainder of the home. The entire interior has been freshly painted and enhanced with updated light fixtures and hardware throughout. The brand-new kitchen boasts granite countertops, soft-close cabinetry, and stainless steel appliances. All 3 bathrooms have been thoughtfully updated, including new vanities and a fully tiled shower in the hall bath. Situated on nearly 1/3 of an acre, the expansive backyard offers endless possibilities. A spacious room over the garage and ample storage in the attic, 2-car garage, and shed complete this exceptional home.

4209 Stonebridge Landing, West Chesapeake

741 Corapeake Drive, South Chesapeake
$515,000
5 Beds ⋅ 2.1 Baths ⋅ 10630218 MLS
Timeless design meets everyday functionality at 741 Corapeake Drive in Chesapeake. Situated on a desirable corner lot in Albemarle Acres, this well-designed home offers a practical and inviting floor plan with defined living spaces and a dedicated dining area great for both daily living and entertaining. Recent updates throughout provide modern finishes and a move-in ready experience, blending classic charm with today’s style. Step outside to a spacious, fenced backyard offering room for outdoor enjoyment, relaxation, or future enhancements. The corner setting adds both curb appeal and additional yard space. Conveniently located in southern Chesapeake, this property offers easy access to shopping, dining, and major roadways, making commuting and daily errands simple. A well-maintained home that combines comfort, updates, and location—ready for its next chapter.

741 Corapeake Drive, South Chesapeake

348 Wisdom Path, South Chesapeake
$715,000
6 Beds ⋅ 3 Baths ⋅ 10630204 MLS
Get Ready to Fall in Love! 6-bedroom, 3-bath Home Features an Open Layout, Neutral Tones, & Tall ceilings w/ Two-Story Open Foyer & Den. A Balcony Overlooks the Main Living Space. The Kitchen Features a Large 7-ft Island, Granite Countertops, a Coffee Bar, & an Electric Range w/ a Gas Hookup Option. Sunroom Off the Kitchen For Extra Dining, a Cozy Gas Fireplace in the Family Room, & a Flexible Formal Living Space Great For a Library or Music Room. Sixth Bedroom Is Currently Used as an Office w/ Closet. Upstairs Primary Suite, w/ a Spa-Like Bath Featuring Double Sinks, a Soaking Tub, a Separate Shower, & a Large Walk-in Closet w/ Built-Ins. Upstairs Laundry. Backyard Includes Paver Patio, Custom Firepit, Playground Area, & a Fully Fenced Yard That Backs to a Wooded Green Space. Tesla Solar Panels w/ Battery System (paid for), & Extra Attic Insulation Keep Electric Costs Low.

348 Wisdom Path, South Chesapeake

607 Rockies Court, South Chesapeake
$640,000
5 Beds ⋅ 2.1 Baths ⋅ 10629620 MLS
Step inside this gorgeous & meticulously maintained 5 bedroom home in sought after 23320 area of Chesapeake w tons of extras!!! Real hardwood flooring throughout, open concept & flexible floorplan to work with your lifestyle. Downstairs offers formal dining room, huge kitchen w double pantry & breakfast nook, family room + bonus room perfect for game room/ home office/ craft room. etc. Located in a quiet cul de sac with private backyard lined w trees (and no immediate rear neighbors). Spacious primary suite w double sinks & walk in closet, second floor laundry room. Crawl space has been fully encapsulated w/ dehumidifier & 30 yr warranty, new garage door w/ opener, new lighting inside & out. Ideal location!

607 Rockies Court, South Chesapeake

1125 Sutherlyn Court, South Chesapeake
$709,500
4 Beds ⋅ 3 Baths ⋅ 10629056 MLS
You need to see this home in person to appreciate! Amazing open layout. This stunning all-brick home sits at the end of a quiet cul-de-sac on a beautifully maintained half-acre lot, offering privacy and charm. Inside, a spacious layout is perfect for everyday living and entertaining. The large living room features a cozy gas fireplace and views of the serene, wooded private backyard while the screened-in porch is ideal for relaxing or hosting. With 4 spacious bedrooms and 3 full baths, including two en-suites, the first-floor primary suite offers a spa-like retreat with a jetted tub, tiled shower and dual vanities. The large primary closet is a clothe’s lovers dream! Bamboo flooring and crown molding add elegance throughout. The FROG with a full bath is perfect for guests! Located in the desirable Great Bridge district near shopping, dining, and the expressway—this home has it all. Brand new sewer pump installed.

1125 Sutherlyn Court, South Chesapeake

407 B Street, Central Chesapeake
$37,500
10627323 MLS
Investor special! Infill lot located in the South Norfolk section of Chesapeake offering approximately 2,962 sq ft (0.07 acres) of residential land with clear development potential. Surrounded by existing homes and ongoing investor activity, this parcel is well-positioned for a spec build, rental portfolio addition, or long-term hold. Located with quick access to major corridors, shipyards, and military bases, supporting steady rental demand and resale viability. The smaller footprint allows for efficient construction costs while maintaining strong upside potential. Great for builders and investors seeking their next project in a market with continued growth and redevelopment. Opportunities at this price point are limited, move quickly. Buyer to perform all due diligence regarding zoning, utilities, setbacks, and buildability.

407 B Street, Central Chesapeake

403 B Street, Central Chesapeake
$37,500
10627317 MLS
Investor alert—opportunities like this don’t last. Prime infill lot located in the established South Norfolk section of Chesapeake, offering approximately 2,962 sq ft of buildable potential in an area seeing ongoing redevelopment and investor activity. Surrounded by existing residential homes, this parcel is great for a quick spec build, rental hold, or long-term appreciation play. Strong proximity to major highways, shipyards, and military bases supports consistent demand and future resale value. The manageable lot size keeps build costs efficient while maximizing ROI potential. Priced to move and ready for immediate action—serious inquiries only. Whether you’re a seasoned investor or builder looking for your next project, this is the type of opportunity that gets scooped up fast. Buyer to perform due diligence regarding zoning, utilities, setbacks, and buildability.

403 B Street, Central Chesapeake

2219 Captiva Lane, West Chesapeake
$660,415
6 Beds ⋅ 3 Baths ⋅ 10608812 MLS
PRE-SOLD | The Magnolia is a grand floor plan with a 2-story foyer as you enter! Large family room that opens to the Kitchen and Eating Area. Downstairs utility space that allows for the perfect 'Mudroom.' 4 spacious bedrooms & 2 baths on the 2nd floor with a finished room over the garage. The 3rd-floor walk-in attic can be upgraded to an additional bed/bath. The Estates at Jolliff Landing is a charming neighborhood boasting single-family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, a community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. Builder is offering partial CCA & $15,000 buyer incentive (see listing agent for details) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

2219 Captiva Lane, 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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