Chesapeake VA VA 2500+ Sq. Ft. Real Estate, Homes, Condos for Sale

FRESH EGGS, BIG FREEDOM, ENDLESS POTENTIAL in Chesapeake's desirable Blackwater area! Welcome to your private sanctuary—the ultimate lifestyle upgrade. Picture sipping morning coffee while collecting farm-fresh eggs from your backyard chickens, surrounded by peaceful green space. Enjoy pure, independent water from your premium 600+ ft Certified Artesian well, complete with a double tank water softener and an energy-efficient tankless electric water heater. Dream big with future-proof infrastructure: an oversized septic system is already in place to support an ADU, multi-generational living, or rental income. Built for comfort and efficiency, this ultimate hobbyist setup includes a premium dual-fuel HVAC and a sub-panel wired for a generator. Whether you envision a luxury guest cottage, a workshop, or an expanded country compound, the foundation is completely set. Schedule your tour today!

1336 Blackwater Road, South Chesapeake

$619,900

4 Beds ⋅ 3.1 Baths ⋅ 10645833 MLS

Come see this beautiful, move-in ready Stephen Alexander home, tucked away on a large private cul-de-sac in the sought-after Grassfield school district. The home’s downstairs features 10 foot ceilings, a family room with crown molding, custom built-ins, and a gas fireplace, and an updated kitchen with a pantry, granite counters, tile backsplash, newer SS appliances (2025), a bar, and a reclaimed barn wood island in the breakfast nook. The large upstairs primary bedroom has His and Hers walk-in closets and a spacious en-suite bathroom with a jetted tub and a separate tiled shower with double showerheads. The FROG serves as the 4th bedroom with its own full bathroom. Additional highlights include a beautiful front porch, a fully fenced-in backyard, a mud room off of the oversized side loading garage with opener, and dual zone HVAC with Nest thermostats. Located in desirable Great Bridge, this home offers easy access to interstates and is just minutes to schools, dining, shopping & more!

901 Hathaway Court, South Chesapeake

$620,000

4 Beds ⋅ 3 Baths ⋅ 10645463 MLS

If you've been looking for a home in Cheshire Forest, this is one you won't want to miss! Nestled in one of Great Bridge's most sought-after communities, this beautifully updated and meticulously maintained 4-bedroom, 3-bath home offers approximately 2,673 square feet of thoughtfully designed living space. The bright, functional floor plan is great for everyday living and entertaining, featuring a well-appointed kitchen with a gas range, center island, breakfast area, abundant cabinetry, and seamless flow into the inviting family room with a gas fireplace and formal dining room. The main level also includes a full bathroom with a walk-in shower, a convenient laundry room, and access to the attached two-car garage. Upstairs, the spacious primary suite offers a large walk-in closet and a relaxing ensuite with a soaking tub and separate shower, while two additional generously sized bedrooms share a full hall bathroom. The finished room over the garage provides incredible flexibility as a fourth bedroom, home office, playroom, media room, or guest space. Step outside to a beautifully landscaped, oversized backyard featuring a large deck great for entertaining, outdoor dining, or simply unwinding. Residents enjoy access to community amenities including a clubhouse, pool, playgrounds, and tennis courts, all conveniently located near shopping, dining, parks, and Great Bridge schools. VA assumable loan at 2.25%

819 Keeling Drive, South Chesapeake

$699,900

4 Beds ⋅ 3.1 Baths ⋅ 10645155 MLS

Welcome to this beautiful and spacious, well-maintained home that boasts 3261 sq.ft., four 2nd floor Bedrooms, 3.5 Baths + 1st floor Office, Dining Room, Sunroom, Family Room with cozy gas log fireplace, Living Room with handsome built-in bookcases, 12x10 shed, over 1/3rd acre corner lot, 1000 sq.ft. paver patio, 2nd floor Bedroom with ensuite bath & adjacent Loft is perfect for an In-Law Suite. 3 car garage provides ample parking and storage. Come see your dream home today!

2300 Burgess Court, South Chesapeake

$660,000

5 Beds ⋅ 3.1 Baths ⋅ 10645822 MLS

Gorgeous and spacious 3500 sq ft home has been updated plus FULLY PAID OFF SOLAR PANELS! Featuring an amazing open concept floor plan with new LVP flooring, a large primary suite with an updated full bath! The home includes fresh painting throughout, newer HVAC, granite counters, a tankless water heater, a large 2 car garage, a metal fenced-in backyard, gazebo and a large 320 sq ft powered shed/workshop! Right near the heart of Greenbrier in Kemp Bridge, you don't want to miss this one!

1439 Kemp Bridge Drive, South Chesapeake

$635,000

5 Beds ⋅ 3.1 Baths ⋅ 10645747 MLS

Beautiful 5-bedroom, 3-bath home built in 2017 and thoughtfully upgraded, located on a private cul-de-sac with a large, vinyl privacy-fenced yard. Inside, the open floor plan features LVP flooring, a gas fireplace, and a seamless flow into the remodeled kitchen, complete with quartz countertops, custom cabinetry, under-cabinet lighting, and updated appliances (2024). The kitchen complimented with a built-in breakfast nook and custom pantry, while additional custom cabinetry enhances select bedrooms. The primary suite offers a stylishly renovated bath for a true retreat feel. Come outside to enjoy the spacious, private backyard, ideal for relaxing or entertaining with gazebo patio, playground, trampoline and kids pool. The home also includes a finished 3+ car garage with epoxy floors, overhead storage, and a 240V outlet for EV/RV/generator use. Additional features include pre-wired surround sound, Cat5/TV connections in all bedrooms, an irrigation well, attic fan.

3500 Kathys Way, South Chesapeake

$725,000

5 Beds ⋅ 3 Baths ⋅ 10645753 MLS

This meticulously cared for home has an open floor plan! Bedroom and full bath downstairs to use for guests or office! Living room is large with gas fireplace and has surround sound. Granite countertops and breakfast bar in the kitchen with a stainless appliance package, custom built ins and large pantry plus a breakfast area. Huge Primary suite has custom closet factory walk in closet. Large bedrooms. Screened in porch overlooks saltwater in ground pool. Sprinkler system, and beautiful views of the water. Amenities in this neighborhood include lakes with fountains, a park, natural landscaping and trails.

136 Bella Drive, South Chesapeake

$699,900

4 Beds ⋅ 4 Baths ⋅ 10645397 MLS

Welcome home to Rollingwood Estates in the highly sought after Great Bridge school district. This one owner brick transitional home offers 4 bedrooms and 4 full baths with an open, bright floor plan designed for comfortable living and effortless entertaining. The spacious FROG serves as the fourth bedroom and features its own private full bath, making it ideal for guests or multigenerational living. The kitchen offers Corian countertops, generous workspace and opens to the main living areas. Step outside to your own backyard retreat with a sparkling inground pool, dedicated pool bath, stamped concrete patio, outdoor bar/kitchen area, screened porch, and professionally landscaped yard. A two car attached garage, irrigation well, and thoughtful layout add to the appeal. Offering exceptional value in an established neighborhood, this home is priced to sell and ready for its next owner to make it their own.

837 Greenfield Lane, South Chesapeake

$765,000

5 Beds ⋅ 4 Baths ⋅ 10645689 MLS

The Macon Model at Riverview Landing - Master Model Listing by Wetherington Homes. Buyers may select their lot and personalize available design options. The community offers eight thoughtfully designed floor plans along with multiple exterior elevations that highlight architectural detail and curb appeal. This plan features five bedrooms, four bathrooms, a loft, and a first-floor bedroom with a full bath. The chef-inspired kitchen includes upscale finishes, a large island, and a Butler's pantry. Designed to balance functionality and craftsmanship, this home offers modern conveniences with thoughtful design throughout. Contact us today for additional information, to join the VIP interest list, and to schedule an appointment. Discover the opportunity to build in this new community with convenient access to everyday amenities!

MM Macon, South Chesapeake

$540,000

4 Beds ⋅ 2.1 Baths ⋅ 10645295 MLS

Located in the highly sought-after Grassfield High School district, this home offers an incredible opportunity to make a home of your own in one of Chesapeake's most desirable areas. Inside features a spacious, functional floor plan boasting nearly 2700 square feet of living space. The living areas are generous with comfortable bedrooms and plenty of room to personalize. Head outside to the home's standout feature -- an expansive backyard and large deck with endless possibilities for entertaining or creating a private outdoor retreat. Conveniently located near shopping, dining, parks, and major interstates!

963 Speight Lyons Loop, South Chesapeake

$899,900

4 Beds ⋅ 3 Baths ⋅ 10645653 MLS

Welcome to The Ashford by Wetherington Homes - MOVE IN BY AUGUST 2026! A 5-bedroom, 3-bath new construction home with over 2,700 sqft on approximately 2 acres in Hickory School District with NO HOA! Designed for todays buyer, this open-concept floorplan offers luxury finishes, designer details, outdoor entertaining, & flexible living spaces. The kitchen features quartz countertops, Frigidaire Professional appliances, custom wood hood, shaker cabinetry, & upgraded lighting. The 1st floor Primary Suite includes a tiled spa-style shower, dual vanities, & oversized walk-in closet. Two additional 1st floor bedrooms offer flexibility for guests or office space. Upstairs includes 2 bedrooms, full bath, & loft ideal for media room, playroom, or gym. Enjoy luxury new construction convenient to Edinburgh, Greenbrier, shopping, dining, & commuter routes while still offering privacy & acreage!

435 Gallbush Road, South Chesapeake

$644,900

4 Beds ⋅ 2.1 Baths ⋅ 10645606 MLS

Ask Agent about a potential VA assumable loan opportunity! Better Than New and Built in 2023, this beautifully and thoughtfully upgraded home offers the benefits of newer construction without the wait. Move-in ready with quick closing available. Bright, open-concept floor plan with abundant natural light. Gourmet kitchen features quartz countertops, oversized island, premium gas range, stainless steel appliances, walk-in pantry, and custom cabinetry. Spacious primary suite includes tray ceiling, dual walk-in closets, soaking tub, tiled shower, and dual vanities. Enjoy covered front and rear porches, extended patio, fully fenced backyard with wooded views, irrigation system, storage shed, custom window treatments, and exceptional attic storage. Convenient to military bases, shopping, dining, and major commuter routes. Trusted lender Steve Hawley (NMLS #1813927) from Southern Trust Mortgage (NMLS #2921) will provide a 1% lender-paid buydown on this listing. Ask Listing Agent for details.

640 Appalachian Court, South Chesapeake

$675,000

6 Beds ⋅ 2.1 Baths ⋅ 10645171 MLS

Rare opportunity to own over 6 private acres in the heart of Deep Creek! This exceptional property includes two parcels conveying with the sale, creating a combined 6+ acres of wooded privacy at the end of a quiet road. The spacious 6-bedroom home offers endless possibilities for multigenerational living, a home office, hobby space, or guest accommodations. Enjoy the peace and seclusion of country-style living while remaining just minutes from shopping, dining, schools, and major interstates. Come see this one first!

3249 Pioneer Lane, South Chesapeake

$639,999

4 Beds ⋅ 2.1 Baths ⋅ 10645551 MLS

Welcome to Warrington Hall in Greenbrier, Chesapeake. This well-maintained brick home offers spacious living with four bedrooms, two and a half baths, and hardwood floors throughout the first floor. Home Features * Bright, airy layout * Well-equipped kitchen * Spacious four-bedroom with 2.5 baths *Community Amenities Enjoy access to a clubhouse, tennis courts, a pool, and playgrounds. Schedule your showing today before this home is gone.

948 Stanhope Gardens, South Chesapeake

$629,000

6 Beds ⋅ 3 Baths ⋅ 10645483 MLS

Rare 6-bedroom opportunity with an ideal multigenerational layout! The first floor features a bedroom, adjacent flex room, and a modified curbless shower, offering exceptional flexibility and accessibility. Beautiful neutral decor, 9' ceilings, hardwood floors, elegant crown molding, and a huge FROG provide room for everyone. The spacious primary suite features hardwood floors and two walk-in closets. Convenient second-floor laundry. Enjoy a large fenced backyard with a powered detached shed and private well for economical lawn irrigation, plus an attached 2-car garage. Meticulously maintained with annual service contracts on the HVAC, tankless water heater, and crawl space. Seller will provide a termite/moisture letter. Convenient to Millville Rd., Veterans Bridge, Shipyard Rd., and major interstates, Portsmouth, Norfolk and Suffolk! Small community vibe with minimal traffic. minimal traffic.

1816 Sunsprite Loop, South Chesapeake

$609,000

4 Beds ⋅ 2.1 Baths ⋅ 10645393 MLS

Premium location in one of Western Branch’s most sought-after neighborhoods & schools. Beautiful, manicured homes w/large lots & no homeowner’s association. Just minutes to 664 & ALL of Hampton Roads Military bases, shopping & entertainment and medical facilities. Step inside to a welcoming foyer that leads to a formal dining room, living room and a custom kitchen with an Island. The sunken den features a gas fireplace which exits to a multi-level deck for cookouts and entertaining. The upstairs features a primary suite for a private retreat with an en-suite bath, a large walk-in closet for keeping all your items organized, while two additional bedrooms (all with walk-in closets) provide versatility for guests or even a game (flex) room. In addition, a 4th bedroom is located over the 576 SQFT. Attached garage. New interior paint and carpet, move in ready

1416 Pine Grove Lane, West Chesapeake

$706,670

5 Beds ⋅ 3 Baths ⋅ 10645425 MLS

The Lehigh single-family home combines smart design with light-filled spaces. Enter the inviting foyer, where versatile flex space can be used as a playroom, living room or office. The gourmet kitchen boasts a large island and pantry and connects to the dining and family room. Off the 2-car garage, a family entry controls clutter and leads to a quiet study/bedroom. Upstairs, a loft is an ideal entertaining spot outside 3 spacious bedrooms and a double vanity bath. The luxurious owner's suite offers a cozy getaway with large closets and private bathroom. You'll love The Lehigh.

217 Henry Jefferson Way, South Chesapeake

$584,900

5 Beds ⋅ 2.1 Baths ⋅ 10645337 MLS

A versatile floor plan with ample space for entertaining! Tha Palm offers 5 Bedrooms , 2.5 Baths, a large Family room, open to the kitchen, all BR's on 2nd floor, large patio space for outdoor living. A desirable Primary Suite bath & walk-in closet.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. A plethora of outdoor activities right at your doorstep in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details, as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5 pm at 5023 Annapolis Drive.

2202 Wilmington Avenue, West Chesapeake

$645,000

4 Beds ⋅ 2.1 Baths ⋅ 10645288 MLS

First Time Buyer 5.5 rate, low down, NO PMI! Joseph’s Meadow MODEL GPS 369 Scotland Ln. Chesapeake. Nestled in Greenbrier come visit the newest community by renowned local builder. Lily Cottage welcomes you w/ a full front porch, soaring 10-foot ceilings, & beautiful hardwood floors throughout the first floor. Designed for entertaining, the open-concept layout seamlessly connects the living room, dining area, & stunning chef’s kitchen featuring a 9-foot quartz island, custom hood, & oversized walk-in pantry. Mudroom & powder room are conveniently tucked away by 2-car garage. Upstairs, a sun-filled loft, two spacious bedrooms, loft (opt 4th), & a large laundry room provide exceptional functionality. The private primary suite offers a custom walk-in closet & spa-inspired bath w/ quartz countertops, dual vanities, freestanding tub, tiled shower, & private water closet. Easy living with professionally managed grounds ensures low-maintenance living, making your dream truly a peaceful haven.

365 Scotland Lane, South Chesapeake

$674,000

5 Beds ⋅ 2.1 Baths ⋅ 10645285 MLS

Welcome home to a beautiful one owner home in the highly sought after neighborhood of Dominion Meadows, and Grassfield High School District. Built in 2020, this home offers a bright open-concept design, with 5 spacious bedrooms, and 2.5 baths. Versatile living room or home office, formal dining room, gourmet kitchen with large island, custom cabinetry, granite countertops, stainless appliances, and pantry flows into the spacious family room. Upstairs you will find a laundry room, and generously sized bedrooms. Luxurious primary suite with tray ceiling, spa bath, oversized custom closet. Outside unwind in the screen porch, or the large patio enjoying privacy in the fenced backyard while spending time with family or entertaining with friends. Easy commute to all military bases, and a few minutes away from shopping, restaurants, and entertainment.

815 Angel Wing Drive, South Chesapeake

$577,740

3 Beds ⋅ 3 Baths ⋅ 10645211 MLS

Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2166 Edwin Drive, South Chesapeake

$585,000

4 Beds ⋅ 2.1 Baths ⋅ 10645167 MLS

Beautifully updated and impeccably maintained, this exceptional 4BR/2.5BA home offers thoughtfully designed living space in the highly sought-after Kemp Woods neighborhood of Chesapeake. Nestled on a quiet, tree-lined street, this move-in ready home perfectly blends timeless elegance, quality craftsmanship, & modern updates. Step inside to an inviting floor plan filled with natural light, with rich hardwood flooring, elegant plantation shutters, and spacious living areas. Gourmet kitchen is designed to impress, featuring tall cabinetry, built-in appliances, abundant counter space, & oversized breakfast area surrounded by windows that fill the space with natural light. Spacious primary suite is a true private retreat, complete with large walk-in closet & stunning, spa-inspired ensuite featuring beautifully tiled, oversized frameless glass walk-in shower, dual vanity, designer lighting, & luxurious finishes that create a resort-like experience at home. 3 additional generously sized bedrooms. Seamlessly extending the living space outdoors, both the family room and breakfast area open to an expansive multi-level deck overlooking the private backyard. Designed for entertaining and everyday enjoyment, this outdoor retreat offers oversized deck and a hot tub—perfect for summer gatherings, peaceful evenings, or relaxing under the stars. Major improvements provide exceptional peace of mind, including a roof, two-zone HVAC system, & numerous updates completed within the last 5 years, allowing the next owner to simply move in and enjoy. Conveniently located just minutes from Greenbrier’s premier shopping, dining, entertainment, parks, hospitals, and major commuter routes including I-64, this home offers the perfect balance of convenience and the quiet charm of one of Chesapeake’s most established and desirable neighborhoods. Some photos were virtually staged or digitally enhanced for marketing purposes to help buyers visualize the property’s potential. Schedule your showing today to make this house YOUR HOME!!

1045 Winchester Way, South Chesapeake

$625,000

4 Beds ⋅ 2.1 Baths ⋅ 10645160 MLS

Stunning 4 bed 2 and a half bath custom-built home. Spacious bedrooms, upgraded kitchen with dual ovens and all newer appliances. Surround sound in the large family room. Newer flooring throughout. Custom built screened in back porch with a beautiful large yard. Relax on the front porch swing while overlooking the quiet cul de sac. Sought after neighborhood with the benefit of accessing major highways, bases & stores in minutes. Seller also providing a one year home warranty. Look at this one first!

1237 Spruce Lane, South Chesapeake

$629,900

4 Beds ⋅ 2.1 Baths ⋅ 10645157 MLS

BUY THIS AWESOME HOME, WE'LL BUY YOURS!* Welcome to your low-maintenance luxury retreat in the sought-after 23322 zip code! This beautifully designed 4-bedroom, 2.5-bath home offers 2,598 sq ft of stylish, comfortable living with minimal upkeep. The highlight is the exceptional outdoor living space—a 529 sq ft covered, screened patio with premium epoxy flooring for entertaining, outdoor dining, or relaxing in privacy. An additional patio and custom walkway are surrounded by professionally landscaped, easy-care grounds. Enjoy a true lock-and-leave lifestyle with an HOA that maintains the front yard, giving you more time to enjoy life instead of yard work. Resort-style community amenities are just steps away, while shopping, dining, parks, and major commuter routes are all nearby. This home offers the perfect blend of luxury, convenience, and carefree living.

1910 Briton Lane, South Chesapeake

$575,000

4 Beds ⋅ 2.1 Baths ⋅ 10645016 MLS

Welcome to this beautifully maintained 4-bedroom, 2.5-bath home offering an open-concept floor plan designed for comfortable everyday living and effortless entertaining. Conveniently located near shopping, dining, and with easy interstate access, this home combines comfort with convenience. Relax and unwind on the spacious deck while enjoying peaceful views of the pond and the surrounding wildlife. The generous primary suite features a large walk-in closet, providing plenty of storage space. The well-appointed kitchen includes a gas range, a large pantry, and ample workspace for cooking and gathering. Located in the highly sought-after Chesapeake School District, this home also offers numerous valuable upgrades, including a new roof (2024), HVAC system (2024), and water heater (2021). Additional features include solar panels for energy efficiency, an irrigation system with a dedicated well, a security system, and the washer and dryer, all of which convey with the home.

1311 Piedmont Arch, South Chesapeake

$689,900

5 Beds ⋅ 3 Baths ⋅ 10644830 MLS

SPACIOUS 5 BEDRM, 3 BATH ALL BRICK HOME NESTLED IN 1 OF GREAT BRIDGE'S MOST DESIRABLE COMMUNITIES. OVER 3,000 SQ FT OF SPACE. FEATURES VERSATILE FLOOR PLAN W/ GENEROUS ROOMS, HIGH CEILINGS, HARWOOD FLOORS & OVERSIZED GARAGES W/BUILT IN STORAGE & WORKSPACE. REAR DECK PROVIDES PRIVATE & RELAXING OUTDOOR AREA. EXCELLENT OPPORTUNITY FOR NEW OWNER TO PERSONALIZE THE INTERIOR & CREATE THEIR DREAM HOME WHILE BUILDING INSTANT EQUITY. CONVENIENTLY LOCATED NEAR TOP RATED SCHOOLS, INTERSTATE MUNICIPAL CTR

806 Falls Creek Drive, South Chesapeake

$1,195,000

4 Beds ⋅ 4.1 Baths ⋅ 10644941 MLS

Dreaming of a Serene Country Retreat just minutes from the city? YOU FOUND IT! A Rare Jewel! Horse Lover's Dream! Almost 9 ac Family Sanctuary. Elegant Custom Built, 4 Ensuite BRs & 1/2 Bath home w/an amazing 10' x 50' front porch! Lovely entry foyer opens to Great Room w/cathedral ceiling, hand scraped engineered flooring & wood burning fireplace framed w/bookshelf cabinetry. 1st Floor Primary BR boasts expansive Bath w/2 Separate Granite Vanities, jetted tub, separate shower & Grand Walk-In Closet. PBR Plantation Shutters reveal peaceful views of property! 10 ft ceilings down & 9 ft up. Kitchen w/granite counters, 2 large pantries, ample cabinetry & generous eat-in area. Formal Dining Room for festive gatherings. Upstairs reveals open sitting area w/chandelier. Expansive FROG-4th Bedroom. 3 Covered porches. 3 Car Garage, Spacious 2 Stall Stable, Large Storage Barn, approx 30' x 20' IG Pool w/stamped concrete surround. Fruit trees & acreage for hobby farming. Don't miss this one!

377 Homestead Road, West Chesapeake

$359,900

4 Beds ⋅ 2 Baths ⋅ 10643890 MLS

The Ultimate Chef's Kitchen: Equipped with a professional-grade gas stove & griddle, a rustic tile backsplash, granite countertops, a farmhouse sink, a pot filler, and stainless steel appliances. Fresh & Modern Upgrades: Brand-new paint, stunning flooring, carpet, and stylish finishes elevate every room while preserving the home's historic soul. Space to Live & Play: Featuring a spacious formal dining room, a bright and airy sunroom, a huge primary suite drenched in natural light, and a massive stand-in attic for ultimate storage. Outdoor Oasis: Step outside to a fully fenced backyard complete with an expansive deck—great for weekend BBQs and entertaining. Prepare to fall in love! This gorgeous home with upgrades in the Historic District of Chesapeake is a wounderful mix of historic curb appeal and sleek, modern living.

1006 Butt Street, Central Chesapeake

$542,000

5 Beds ⋅ 2.1 Baths ⋅ 10644796 MLS

Large Home 3300 sq ft in Western Branch area of Chesapeake 5 Bedrooms, Large Family room with wood burning fireplace. Gas Water Heater & Gas Heat, Large Fenced Yard w/10X10 Shed; Roof 2014 (50 year architectural) Well, Sprinkler System Front Yard. Large Kitchen with Island & Walk in pantry. Large Primary Ensuite with walk in Closets; Dual sinks. Seller Offering CCA or Rate Buy Down with Full Price offer

3025 Crossings Drive, West Chesapeake

$609,900

4 Beds ⋅ 3.1 Baths ⋅ 10644569 MLS

100% move-in ready in the Grassfield school district! This open floor plan offers quality finishes throughout. Hardwood flooring runs throughout the main living areas. The first-floor office/study has direct access to the wraparound front porch. The family room opens to the dining area and spacious kitchen featuring granite countertops, white soft-close cabinets, a large island, stainless steel appliances, and a walk-in pantry. Enjoy the private, fully fenced backyard with a custom paver patio. The room over the garage is a private guest suite with a full bath and separate access from the foyer. Upstairs also offers a loft, 2 spacious bedrooms, and the primary suite with a large walk-in closet, soaking tub, oversized tiled shower with custom glass enclosure, and private water closet. No HOA. Convenient to schools, shopping, dining, and major commuter routes.

1933 Reefwood Road, South Chesapeake

$719,000

5 Beds ⋅ 3 Baths ⋅ 10644835 MLS

Your new home in the beautiful Chapel Hill Estates has arrived. Spacious modern house on a 0.3 acre corner lot. 5 bedrooms including a room on the first floor with a full bath! Beautiful wood flooring and decor throughout that really makes this feel like home. Back porch looks out over an incredible fenced in backyard. Everything you want in your forever home can be found here!

1228 Rosebud Lane, South Chesapeake

$825,000

5 Beds ⋅ 3 Baths ⋅ 10644737 MLS

Beautiful 5 Bedroom Brick Home featuring a spacious open floor plan perfect for everyday living and entertaining. The large kitchen offers stainless steel appliances, abundant cabinetry, and ample prep space. A standout feature of the home is the custom library, complete with French doors, built-in shelving, and a rolling ladder, creating an elegant and inviting space for work, reading, or relaxation. The main level includes a guest bedroom and full bath. Upstairs you'll find a media room and an oversized primary suite with double closets and a luxurious bathroom featuring a jetted tub, separate shower, a double vanity and private toilet room. Be sure to notice the built-in light-up stairs going up to the second floor! Enjoy your own private backyard oasis with mature landscaping, an in-ground saltwater pool, hot tub, and an expansive custom paver patio, ideal for relaxing or entertaining. Extended driveway with Boat/RV pad. Located in the sought after Great Bridge school district and community, local shops and restaurants, and close to the interstate for a quick trip to OBX!

208 Leicester Court, South Chesapeake

$699,900

5 Beds ⋅ 3.1 Baths ⋅ 10644549 MLS

Experience everyday convenience and modern living in this stunning Ashburne floorplan featuring over $90,000 in custom upgrades. Situated on a large lot, this exceptional home offers the perfect blend of comfort and style. Relax on the spacious covered patio with peaceful pond views. Inside, enjoy open-concept living with 9' ceilings, beautiful wide oak flooring, and custom white cordless blinds throughout. The designer kitchen features white shaker cabinetry with custom pull-out drawers and dividers, a contrasting blue island, quartz countertops, and an upgraded appliance package. Two primary suites—1 on each level—plus 3 additional bedrooms provide exceptional flexibility. Additional highlights include a custom tile and frameless glass shower in the upstairs primary suite, crown moulding, walk-in closets with wood shelving, and a 2-car garage with epoxy flooring and 220V/50A EV outlet. Resort-style amenities include a pool, fitness center, clubhouse, playground, and scenic lakes.

410 Middleton Way, South Chesapeake

$499,900

4 Beds ⋅ 2.1 Baths ⋅ 10644750 MLS

Beautifully renovated and move-in ready, this spacious 4-bedroom, 2.5-bath home offers approximately 2,621 square feet, including an addition that provides extra living space. The open and inviting main level features fresh luxury vinyl plank flooring, updated lighting, and a bright sunroom. The updated kitchen offers granite countertops, stainless steel appliances, and attractive cabinetry. Upstairs, you’ll find four comfortably sized bedrooms with new carpeting and updated bathrooms featuring modern ceramic tile. The home is equipped with gas heat and central air conditioning on the first floor and a heat pump serving the second floor. Additional features include an attached garage, a generous lot, and a roof replaced approximately in 2021. Conveniently located in Western Branch near shopping, dining, schools, and major roadways with access throughout Hampton Roads. Schedule your showing and see all this home has to offer.

4257 Meadow Wood Drive, West Chesapeake

$749,900

5 Beds ⋅ 2.1 Baths ⋅ 10644769 MLS

Come relax and float in the lake. Stunning 2 story open & airy with cozy den & built in shelves and gas logs Newer kitchen with double ovens upgraded appliances. Large Sun Room Mr. Rogers lifetime windows. Shed with power. New light fixtures. Primary closet has California Closets System system. Tray ceiling. Freshly painted and new carpet.

928 Sydenham Boulevard, South Chesapeake

$815,000

5 Beds ⋅ 4 Baths ⋅ 10644739 MLS

This home has it all! Tall ceilings,recessed lighting throughout,custom built ins, ship lap walls, a high end kitchen with a built in area with electrical for a wine or beer fridge, frosted glass barn doors, a mud room, a primary suite like no other with a cool room off it that could be turned into a secret room for fun or games. The open floor plan and large lot invites entertaining or relaxation while spending time with friends or loved ones. The property line goes back into the woods beyond the large fenced in area. There is an extended drive way for plenty of parking, a large professionally built and installed shed that replicates a small home. Plush grass with installed drainage.There is so much more to tell but seeing is believing don't wait to take a tour of this magnificent home located on a small culdesac.

2504 Calabria Dr Drive, South Chesapeake

$594,900

4 Beds ⋅ 2.1 Baths ⋅ 10644498 MLS

Beautiful ranch-style home tucked away on a quiet cul-de-sac in Chesapeake’s Bayberry Forest! This spacious 4-bedroom, 2.5-bath home offers generous living areas, an attached 2-car garage and thoughtful updates throughout. The fenced backyard is made for relaxing or entertaining with a deck, storage shed and beautiful landscaping. Inside, enjoy a fully conditioned sunroom for year-round use, a finished room over the garage, large bedrooms with step-in showers in both bathrooms. Recent upgrades include a new HVAC system in 2024, new LVP flooring, an encapsulated crawl space and a whole-house generator for added peace of mind. The bright, open kitchen features an island with guest seating plus room for a table, while the formal dining room gives you extra space for gatherings. Between the inviting living room and comfortable den with gas fireplace, there is plenty of room to enjoy family and friends. Centrally located near shopping, dining, interstate 64 and bases.

1305 Forest Point Drive, South Chesapeake

$539,999

4 Beds ⋅ 2.1 Baths ⋅ 10644558 MLS

Located in the highly sought-after Jolliff Landing neighborhood of Western Branch, this like-new home has tons to offer! Backing to a protected preserve, you’ll have added privacy with no future construction behind you. Featuring an open floor plan with a versatile bonus/flex room and beautiful LVP flooring throughout the main living areas. The gourmet kitchen is equipped with stainless steel appliances, a gas range, quartz countertops, and a custom tile backsplash. A large center island makes entertaining easy, while the cozy gas fireplace adds warmth and charm to the living space. Additional upgrades include smart blinds, smart ceiling lighting in the living room, and an updated primary walk-in shower with a glass door. The community provides amenities such as a pool, walking trails, parks and plazas with outdoor seating, a playground, natural preservation areas, and a state-of-the-art clubhouse with kitchen, conference room, and fitness center. New construction without the wait! Schedule your showing today! Open to a 1-year lease at $3,600 per month. If you're interested in leasing or would like more information about this option, please contact the listing agent.

2216 Hampton Roads Parkway, West Chesapeake

$650,000

6 Beds ⋅ 3 Baths ⋅ 10644555 MLS

Only 4 yrs young, this thoughtfully designed home offers exceptional space, flexibility, and stylish finishes throughout. The versatile first-floor room with access to a full hall bath is ideal for a guest room, office, or playroom. The open-concept kitchen is beautifully appointed with quartz countertops, s/s appliances, a large island and generous prep space, flowing seamlessly into the main living areas. Upstairs, the spacious primary suite is a true retreat featuring a spa-inspired bath w/an oversized shower & two showerheads & a large walk-in closet. Total of 6 bedrooms provide endless possibilities for today's lifestyle & multi-generational living. Step outside to your private backyard oasis complete with an in-ground swimming pool, built-in hot tub, and plenty of room for relaxing or entertaining. Other highlights include an EV charger and modern construction, offering the peace of mind that comes with a newer home.

4026 Scotfield Drive, West Chesapeake

$670,000

4 Beds ⋅ 2.1 Baths ⋅ 10644514 MLS

Welcome home to sought after Etheridge Lakes! Nestled at the end of a cul-de-sac, this move in ready home in the Hickory school district has it all! Newer LVP flooring on first floor, granite counters, SS appliances, breakfast area, formal living and dining and sunroom overlooking the large backyard. The primary bedroom has an additional flex room - perfect as an office, nursery, exercise or sitting room. Primary bath recently updated, driveway extended, 30-amp electric added for RV, all surrounded by a white picket fence! See this one first!

806 Crosswood Court, South Chesapeake

$793,267

5 Beds ⋅ 3 Baths ⋅ 10644581 MLS

The Bellhaven at Riverview Landing by Wetherington Homes. Estimated September 2026 delivery. Flexible 4-5 bedroom floor plan with an open-concept layout. Chef’s kitchen connects to the dining area through a butler’s pantry and features dual ovens, gas range, hood, and large island overlooking the covered rear porch. Upstairs loft and main-level full bath add functional living space. Includes a curated list of standard features, with time to personalize select options. Cul-de-sac lot in an active community with walking trails, fire pit, and convenient access to schools, beaches, parks, restaurants, and more! Contact the sales counselor to schedule an appointment and learn about current incentives.

212 Kwanzan Court, South Chesapeake

$689,000

5 Beds ⋅ 2.1 Baths ⋅ 10644518 MLS

Beautifully maintained 5-bedroom, 3,383-square-foot home offering peaceful golf course views in sought-after Wedgewood Estates. The thoughtfully designed floor plan features spacious living areas, an updated kitchen with a large center island, abundant cabinetry, and an open flow into the family room, creating a welcoming space for everyday living and entertaining. Large rear windows fill the home with natural light while overlooking the golf course and a beautiful wooded backdrop. Step outside to enjoy the screened porch and expansive patio, creating a private outdoor retreat. Thoughtfully maintained and exceptionally cared for, this home combines timeless character, quality updates, and outstanding curb appeal. Conveniently located in the heart of Greenbrier, just minutes from shopping, dining, parks, major highways, military installations, and healthcare, while offering the privacy and charm of one of Chesapeake's most desirable established neighborhoods.

1118 Fairway Drive, South Chesapeake

$449,000

3 Beds ⋅ 2.1 Baths ⋅ 10644169 MLS

Enjoy low-maintenance living in this beautifully maintained end-unit townhome in a sought-after 55+ community. This home features a first-floor primary suite, an open-concept living area with a gas fireplace, a spacious kitchen with upgraded cabinetry, a dining room, private office, and a convenient first-floor laundry room. Step outside to the screened-in porch, where you can enjoy views of the community pool from your fenced backyard and take advantage of easy access to the clubhouse. Upstairs offers additional bedrooms, a versatile loft, abundant storage, and an unfinished fourth bedroom currently used for storage that can easily be finished to suit your needs. Community amenities include a fitness center, resort-style pool, full kitchen, fire pits, fire tables, and a dog park. Complete with an attached two-car garage, this home combines comfort, convenience, and an active lifestyle.

3106 Lantern Place, West Chesapeake

$599,000

5 Beds ⋅ 3 Baths ⋅ 10644309 MLS

Tired of expensive water and sewer bills, HOA restrictions, or dealing with the stress and cost of a fixer upper? Then this brand new home is exactly what you have been waiting for. Welcome to this stunning 2,600 sq. ft. open concept residence built by local award winning builder. Featuring 5 spacious bedrooms, including a first floor bedroom great for guests or multi generational living, and 3 full baths with upscale designer finishes throughout. Enjoy luxury features including granite countertops, ceramic tile, luxury vinyl plank flooring, a cozy fireplace, and a beautiful standalone soaking tub. With NO HOA, this property is superb for boat owners, campers, trailers, or anyone wanting freedom and flexibility without extra fees or restrictions. Located in a highly sought school district with flexible spaces wonderful for entertaining and everyday living. Everything is brand new, offering peace of mind and low maintenance living.

785 Caddie Street, South Chesapeake

$795,000

6 Beds ⋅ 3.1 Baths ⋅ 10643149 MLS

Well-maintained, spacious home on a prime lot in the beautiful Riverwalk community. New Roof, all new Windows, new paint interior and exterior, and new carpet in 2026! Beautiful wood floors in living and dining areas. Six bedrooms, 3 full and 1 half baths. Designed for those who love to entertain, the expansive floor plan offers elegant gathering spaces, abundant natural light, a formal butler station off the dining room. and exceptional flow throughout. The spacious eat-in kitchen and bar-top seating area open to the inviting family room with a cozy fireplace. Three additional bedrooms are located on the second level, including a versatile FROG that can serve as the 6th bedroom, home office, or recreation room. Current cooktop and built-in microwave to be replaced; buyer can choose. Large back deck with gas hookup. Residents of Riverwalk enjoy exceptional neighborhood amenities, including walking trails, a community pool, boat ramp and dock, playground, and a popular summer swim team. This is a wonderful opportunity to own a meticulously cared-for home in one of Chesapeake’s most desirable communities.

804 River Strand, South Chesapeake

$820,000

5 Beds ⋅ 3 Baths ⋅ 10643909 MLS

Spacious 5 Bedroom, 3 Bath home on a beautiful 3-acre lot in the Grassfield High School district! On the main level you'll find LVP flooring, elevated lighting, updated Eat-in Kitchen w/huge island, stainless steel appliances including a Viking gas range, pantry and reverse osmosis drinking water, Family room with gas fireplace, Living and Dining Rooms and full bath. Primary Bedroom with walk-in closet and luxury ensuite bath, 4 secondary bedrooms, laundry (combo W/D unit) and full hall bath complete the 2nd floor. 2-car garage and abundant storage. Outside is made for fun and entertaining with an in-ground pool, stamped concrete patio, and an outdoor kitchen with grill, smoker, and pizza oven. A wonderful space to make memories with family and friends! Major updates include a brand-new dual-zone HVAC (2026), water heater (2025), water softener, garage doors and openers, repaved driveway, new soffits, fascia, gutters, window wrap, and front railing. No HOA! Enjoy the best of both worlds with a peaceful private setting while just minutes from shopping, restaurants, highways and everyday conveniences. Move-in ready!

1932 Foxwood Drive, South Chesapeake

$650,000

5 Beds ⋅ 4.1 Baths ⋅ 10643883 MLS

FSBO Sale

636 Colonel Byrd Street, South Chesapeake

$645,000

4 Beds ⋅ 2.1 Baths ⋅ 10644442 MLS

Experience the lifestyle you've been searching for in one of Chesapeake's most desirable communities, just minutes from top-rated Grassfield High School. This beautifully maintained home welcomes you with a charming front porch and gleaming hardwood floors throughout the main level. A versatile flex room that can be used for a home office, playroom, or sitting area, while the formal dining room flows into the updated chef's kitchen featuring granite countertops, refreshed cabinetry, and new stainless steel appliances. The kitchen opens to a spacious family room centered around a cozy fireplace and an inviting sunroom filled with natural light. Upstairs, the expansive primary suite offers a spa-inspired bath with dual vanities, a jetted tub, and a glass-enclosed shower, along with three additional bedrooms, a full bath, and a convenient second-floor laundry room. Step outside to your own private backyard retreat complete with a stamped concrete patio, sparkling in-ground pool, and fully fenced yard—ready for relaxing or entertaining all summer long. Additional upgrades include a tankless water heater, solar panels that significantly reduce electric costs, updated main-level lighting, and a VA assumable loan with an incredible 3% interest rate for qualified buyers. Tesla EV charger.

2101 Beeblossom Lane, South Chesapeake

$1,299,997

4 Beds ⋅ 2.1 Baths ⋅ 10644328 MLS

Custom 4,300+ sq ft estate on 3 private, wooded acres on historic Taft Rd., located in the Hickory/Grassfield school districts. Perfect blend of country living & city access. Inside features exceptional build quality, ornate plasterwork, dentil moulding, & dual staircases. The main level hosts a home office, living room with a wood fireplace, half bath, & a sunroom. The spacious kitchen boasts a center island & matte white cafe; appliances, leading to a laundry room & 2-car heated garage. Upstairs features 4 large bedrooms, including a primary suite with 2 walk-in closets & 3rd-floor access. 2 full baths feature luxury defogging mirrors. The 3rd floor is ideal for a 2nd living room/studio. Outside boasts a wrap-around porch, 32k-gal saltwater pool (new liner 2025; new pump/filter/salt cell 2026), Trex deck, heated 3-car detached garage with mini-split, carport, shed (new roof 2026), & pole barn. Features 400A service (200A panel), generator tie, & grill propane line. Move-in ready!

1741 Taft Road, South Chesapeake

$664,990

5 Beds ⋅ 3 Baths ⋅ 10644366 MLS

Come see why families are calling Patriots Ridge home! The Hudson single-family home fits the way you live. Flex space can be used as a playroom, a library and more. Gather in the spacious family room, which flows into the dining room and gourmet kitchen, separated by a convenient breakfast bar. Off the 2-car garage, a family entry controls clutter, while a quiet study is tucked away. Upstairs, 3 bedrooms offer abundant closet space and a full bath provides privacy. Your luxurious owner's bath will stun with its double bowl vanity and huge closet. Come home to The Hudson.

212 Tinker Street, South Chesapeake

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