Refine Search
Sort by
1701 Pasture Place, South Chesapeake
$450,000
3 Beds ⋅ 3.1 Baths ⋅ 10640065 MLS
Welcome to The Reserve at Grassfield, one of Chesapeake's most sought-after communities. From the moment you enter this stunning 2021-built townhome, the meticulous care and decor from a curated eye is unmistakably clear. Spanning 2,228 sq ft of low-maintenance luxury across three finished levels, every corner radiates pride of ownership. The entry level offers a versatile flex space. Great for an inspiring home office or a welcoming guest suite, with direct garage access. The main level is an entertainer’s dream, featuring an open-concept layout, a cozy gas fireplace, and finishes bathed in abundant natural light. Upstairs, unwind in a serene primary suite complete with a double-sink vanity and walk-in closet, alongside two additional bedrooms. Enjoy premium community amenities: Fitcore Extreme Obstacle Course, playground, pavilion, scenic pond, and dog park. Near Naval Station Norfolk, NAS Oceana, I-64, and top schools. Low $125/mo fee. Your dream home awaits.

1701 Pasture Place, South Chesapeake

413 Creekwood Drive, South Chesapeake
$474,900
4 Beds ⋅ 2.1 Baths ⋅ 10638389 MLS
Completely transformed and move-in ready, this beautifully remodeled 4-bedroom, 2.5-bath home offers the perfect blend of modern style and everyday comfort. Nearly every interior surface has been updated, creating a fresh feel throughout. The stunning new kitchen features updated cabinetry, countertops, fixtures, and brand-new appliances, while the renovated bathrooms showcase stylish finishes and thoughtful upgrades. Fresh paint, new flooring, and modern touches throughout the home make it feel like new. The spacious floor plan includes an inviting eat-in kitchen, comfortable living areas, and a large primary suite with a walk-in closet and private bath. Outside, you'll find a huge fenced backyard with plenty of room for entertaining, pets, or play. Don’t miss out on this gorgeous home that is truly move-in ready!

413 Creekwood Drive, South Chesapeake

201 Andiron Arch, South Chesapeake
$545,000
5 Beds ⋅ 2.1 Baths ⋅ 10635829 MLS
Welcome to this beautifully maintained home on a spacious corner lot backing directly to a city park, offering the perfect blend of privacy, outdoor space, and neighborhood charm. Chosen by the current owners for its ideal setting and room for kids to play, this home offers both comfort and functionality throughout. Inside, you’ll find a large kitchen with plenty of space for gathering and entertaining, along with a dedicated office and formal dining room for added flexibility. Several bedrooms are generously sized, including the oversized room across from the primary suite, previously used as a playroom. Located in the highly sought-after Grassfield High School district, residents also enjoy HOA amenities including a community pool and rentable clubhouse for events and gatherings. Thoughtful updates over the years make this home move-in ready and easy to enjoy from day one

201 Andiron Arch, South Chesapeake

941 Painted Lady Place, South Chesapeake
$644,900
4 Beds ⋅ 2.1 Baths ⋅ 10634473 MLS
This home shows pride of ownership located in sought after Grassfield area! This spacious 4 bedroom, 2.5 bath home offers an open & inviting layout filled w/ natural light. The first floor features an eat in kitchen open to the living room, formal dining area, guest half bath, & a flexible sitting room can be used for a home office, playroom, or study. Upstairs you'll find a large primary suite with tray ceilings, a custom walk in closet, and beautifully updated shower, and 3 additional bedrooms and convenient second floor laundry. Enjoy the benefit of solar panels that will be paid off at closing, helping keep utility costs low while you enjoy all this home has to offer. Step outside to your private backyard oasis featuring an inground saltwater pool, patio & oversized lot backing to woods. Updates include kitchen appliances 2024-2025, pool pump & filter 2022, salt cell 2025, pool light & diving board 2026, carpet 2021, well & sprinkler system, 3rd driveway & backyard walkway 2022

941 Painted Lady Place, South Chesapeake

444 Fleming Circle, South Chesapeake
$464,000
4 Beds ⋅ 3 Baths ⋅ 10639032 MLS
Welcome to this well-maintained Chesapeake home tucked away on a cul-de-sac! Offering approximately 2,100 square feet of living space, this versatile property features 4 bedrooms, 3 full bathrooms, and plenty of room to fit your lifestyle. Inside, you’ll find fresh paint, abundant storage, and a flexible floor plan that includes a flex room, formal dining room, and a family room. The spacious eat-in kitchen offers ample cabinetry and storage, making meal prep and entertaining a breeze. One of the home’s standout features is the converted garage, creating a large additional living area complete with a full bathroom. This versatile space could serve as a second primary suite, guest quarters, media room, playroom, or whatever best suits your needs. Situated on a generous 0.4-acre lot, the expansive backyard provides endless opportunities for outdoor entertaining, gardening, or simply relaxing. Conveniently located near shopping, dining, schools, and major commuting routes.

444 Fleming Circle, South Chesapeake

733 Whisper Walk, South Chesapeake
$330,000
3 Beds ⋅ 2.1 Baths ⋅ 10638717 MLS
Beautifully located on the lake, this home includes part of the lake within its property lines. There is a spacious 1st-floor primary suite with walk-in closet, sun-filled full bath, including a large jetted tub & separate shower. Two additional BRs & a full bath are found upstairs. The loft area is used as one of the two upstairs BRs which currently overlooks the great room below with its cathedral ceiling and wall of windows. The trex-style deck overlooks the beautiful lake and includes a nice awning for those sunny afternoons. Easy access to the bulkheaded lake affords great fishing. The lot is huge (over 1/4 AC) and extends well to the right beyond the wood fence in the backyard (see plat map in listing documents). Being sold AS IS, seller believes all mechanicals and basic structure to be in good condition, but there are cosmetic repairs needed and updates to the kitchen and baths which will bring its new owner greater value. Similar homes have sold for $385K and $406K.

733 Whisper Walk, South Chesapeake

1440 New Mill Drive, South Chesapeake
$475,000
4 Beds ⋅ 2.1 Baths ⋅ 10636897 MLS
Gorgeous four bedroom home in the desirable Country Club Meadows community. Large windows throughout fill the home with natural light, creating a bright and inviting atmosphere. The main level offers a charming sitting area, a sunlit dining room, and a cozy living room with a fireplace. At the center of it all, the open kitchen features beautiful white cabinetry and stainless steel appliances. Upstairs, the primary suite includes a walk-in closet and a private ensuite bath, while three additional bedrooms are generously sized with ample closet space. Head outside to a spacious, fully fenced backyard featuring a covered patio and plenty of space for outdoor entertaining, gardening, or play. You'll also enjoy the attached garage providing additional storage and everyday convenience.

1440 New Mill Drive, South Chesapeake

4210 Cornland Road, South Chesapeake
$610,500
2 Beds ⋅ 2 Baths ⋅ 10631611 MLS
Set on an expansive 7.86+/- acres in Chesapeake’s desirable Hickory area, this property offers a rare blend of privacy, open space, and rural charm. The nearly eight-acre setting features a mix of wooded and open land, creating a peaceful and versatile environment ideal for a private retreat, recreation, or future potential. The 2,088+/- sq ft home is complemented by a detached garage with FROG, and separate workshop, providing comfort and functionality in a spacious countryside setting. Property will be sold at Auction on 5/20/26 at 11:00 AM, list price is starting bid only, final selling price TBD at live auction, with online bidding available. Sold as-is; seller will make no repairs. Termite and moisture inspection and home inspection reports are provided on the auction house website for informational purposes only. Pre-auction offers considered. Public preview 5/16/26 at 10:00 AM (no reservation required). Bid, Win & Sell Confidently!

4210 Cornland Road, South Chesapeake

1952 Lancing Crest Lane, South Chesapeake
$1,400,000
5 Beds ⋅ 4 Baths ⋅ 10629055 MLS
Stunning custom-built waterfront home on over 1.5 acres along the Elizabeth River in Chesapeake. This 5-bedroom, 4-bath residence offers an open, functional layout with granite countertops, custom cabinetry, and multiple living spaces ideal for entertaining. The spacious primary suite features a spa-like bath with soaking tub, tiled walk-in shower, and dual vanities. Enjoy resort-style outdoor living with a saltwater pool, stamped concrete surround, and black wrought iron fencing. The impressive 220-foot private pier provides deep water access and includes a 7,500 lb boat lift, two jet ski lifts, and a covered boathouse. A rare opportunity to own a private waterfront retreat offering space, luxury, and direct access to a boaters' paradise. Flood Insurance is less than 1k a year and is transferable. Community has a private dock and boat launch for residents.

1952 Lancing Crest Lane, South Chesapeake

404 Bracey Way, South Chesapeake
$835,000
5 Beds ⋅ 3.1 Baths ⋅ 10638026 MLS
Meticulously maintained all-brick waterfront home with deep-water access on the Elizabeth River. This thoughtfully designed residence features an open floor plan with expansive water views from the main living areas and the first-floor primary suite. Recent updates include dual HVAC systems and a water heater, all replaced in 2020. Enjoy direct river access from the recently added dock and boat lift, optimal for boating and other waterfront activities. The combination of quality construction and exceptional waterfront location creates a rare opportunity to enjoy life on the water. Conveniently designed for comfortable everyday living and entertaining, this home offers beautiful views, functional living spaces, and easy access to all the Elizabeth River has to offer.

404 Bracey Way, South Chesapeake

2305 Shorebird Court, South Chesapeake
$470,000
4 Beds ⋅ 2 Baths ⋅ 10636769 MLS
Located in one of the most desirable parts of Deep Creek and within the highly sought-after GRASSFIELD HIGH SCHOOL district, this rare find offers the perfect blend of space, comfort, and water access. This one-level floor plan features a MASSIVE KITCHEN ISLAND and beautiful MAPLE HARDWOOD FLOORS throughout. The sunroom is filled with NATURAL LIGHT and overlooks a VERY LARGE BACKYARD—featuring a four season porch, PREMIUM PLAYGROUND SET with a dedicated pea gravel play area, plus plenty of room to entertain, beautiful Spring plants, PERGOLA, and space to host a wedding. The insulated garage offers incredible flexibility and could easily function as a HOME GYM or workshop. The property backs up to TIDAL WATER with water access during high tide—perfect for launching a canoe or kayak Enjoy quiet days on the water or go fishing. Tucked away on a peaceful CUL-DE-SAC with NO FLOOD INSURANCE REQUIRED.

2305 Shorebird Court, South Chesapeake

225 Creston Court, South Chesapeake
$635,000
5 Beds ⋅ 3 Baths ⋅ 10633572 MLS
Welcome home to your private retreat—where comfort, space, and thoughtful design come together beautifully. Tucked away on a quiet cul-de-sac, this stunning home invites you to unwind the moment you step inside.The oversized great room, adorned with coffered ceilings and a cozy gas fireplace, flows effortlessly into the gourmet chef's kitchen. Enjoy preparing meals around the large granite island, surrounded by stainless steel appliances, soft-close dovetail cabinetry, and abundant storage.With five generously sized bedrooms, each featuring its own walk-in closet, everyone has room to relax. The luxurious primary suite is a true sanctuary, offering a spa-like ensuite with a jetted tub, standing shower, double sinks, and dual walk-in closets. A first-floor bedroom with its own ensuite provides the ideal space for guests or multi-generational living, while the formal dining room adds a touch of elegance for special occasions.

225 Creston Court, South Chesapeake

1000 Doe Run Court, South Chesapeake
$605,000
4 Beds ⋅ 2.1 Baths ⋅ 10636060 MLS
Welcome to this beautifully maintained 4-bedroom, 2.5-bath home tucked away on a quiet court in the highly sought-after Grassfield school district! A charming front porch added by the current owners welcomes you into a dramatic two-story entryway filled with natural light. The spacious layout features a dedicated home office, newer carpet, a large FROG, and a cozy wood-burning fireplace. The eat-in kitchen offers quartz countertops, stainless steel appliances, and a stunning tiled backsplash. The primary suite features a soaking tub, two separate walk-in closets, a new vanity, and filtered shower head. Additional updates include a new water heater. Enjoy the private backyard with a privacy fence and easy access through the rear gate to nearby dining and coffee shops. Conveniently located just minutes from the interstate in a peaceful neighborhood with minimal traffic.

1000 Doe Run Court, South Chesapeake

1949 Shipyard Road, South Chesapeake
$410,000
3 Beds ⋅ 2 Baths ⋅ 10633411 MLS
Enjoy the best of both worlds—PEACEFUL COUNTRY LIVING JUST MINUTES FROM CITY CONVENIENCES! This beautifully updated home sits on nearly 2 ACRES, offering space, privacy, and modern comfort. Step inside to find fresh paint, brand-new LVP flooring, and plush carpet throughout the bedrooms. The stunning open kitchen is a chef’s dream, equipped with gleaming quartz countertops, stainless steel appliances, white shaker soft-close cabinets and drawers, recessed lighting, tile backsplash and a farmhouse kitchen sink. Both bathrooms have been tastefully renovated with contemporary finishes, tile flooring and elegantly crafted tile surround shower and tub. The generous setback from the road enhances privacy and provides a tranquil setting. Plenty of storage with an oversized detached garage / workshop. Whether you're relaxing indoors or exploring your expansive property, this home delivers the perfect blend of rural tranquility and urban accessibility. Don’t miss this move-in ready gem!

1949 Shipyard Road, South Chesapeake

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

2301 Gates Landing, South Chesapeake

1203 Pino Court, South Chesapeake
$570,000
3 Beds ⋅ 2.1 Baths ⋅ 10632539 MLS
Beautifully situated on a cul-de-sac in Las Gaviotas, this home offers a spacious and functional layout great for everyday living and entertaining. The first floor features two generous living areas, an updated kitchen, and a formal dining space. The primary suite includes a versatile bonus area good for a home office, den, or easily converted fourth bedroom. Upstairs, two additional bedrooms offer abundant natural light and great space, along with a convenient second-floor laundry room. Recent updates include newer windows, ductwork, a 2-year-old HVAC system and hot water heater, and an encapsulated crawlspace for added efficiency and peace of mind. Enjoy a private backyard with a deck—great for relaxing or entertaining all summer long.

1203 Pino Court, South Chesapeake

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

931 Centurion Circle, South Chesapeake

1001 Azalea Court, South Chesapeake
$615,000
4 Beds ⋅ 2.1 Baths ⋅ 10632333 MLS
Nestled on a quiet cul-de-sac in the heart of Great Bridge, this beautifully maintained home is sure to impress. From the moment you arrive, the home’s curb appeal is undeniable, with a charming front porch that warmly welcomes you inside. The inviting floor plan features a formal dining room, a office/study, and a spacious living room. At the heart of the home, the kitchen shines with a large center island, shiplap backsplash, granite countertops, stainless steel appliances, and a bright breakfast nook. Upstairs, the primary suite offers a generous walk-in closet and an impressive en suite bathroom. Two additional bedrooms are well sized and provide ample closet space, while the finished room over the garage is great for a guest suite, media room, or flex space. Head outside to enjoy the expansive, fully fenced backyard complete with a large deck where you are sure to enjoy entertaining or relaxing while overlooking beautiful, mature trees.

1001 Azalea Court, South Chesapeake

2244 Benefit Road, South Chesapeake
$727,500
4 Beds ⋅ 2.1 Baths ⋅ 10631960 MLS
Welcome to 2244 Benefit Road in Chesapeake—a rare opportunity to own 6 private acres with the freedom of A-1 zoning and all the charm of country living, just minutes from city conveniences. This 2,300 sq ft home offers space, versatility, and major updates including a brand-new roof and new HVAC system for peace of mind. Bring your horses, cows, chickens and create the lifestyle you’ve been dreaming of—farmette, homestead, or private retreat. Bordered by a nature preserve, you’ll enjoy protected views and no future development behind you. The acreage, privacy, and agricultural zoning make this one stand out among Chesapeake homes for sale. Room to garden, ride, entertain, or simply enjoy wide open space under the stars. If you’ve been searching for homes with land in Chesapeake, horse property, or a unique rural escape with modern comfort, this is the one. Rarely does acreage, freedom, and location come together like this!

2244 Benefit Road, South Chesapeake

449 Sawyers Mill Crossing, South Chesapeake
$535,000
4 Beds ⋅ 3 Baths ⋅ 10630276 MLS
Beautifully remodeled 4-bed, 3 bath home, 2,384 sq. ft in sought after Sawyers Mill Community of Chesapeake & Grassfield Schools. Open/spacious living on 1st floor. New carpet & LVP, Fresh paint throughout, new light fixtures, ceiling fans, plumbing fixtures, toilets, new stainless steel appliances, white shaker cabinets in kitchen & baths, soft close doors & drawers, floor to ceiling pantry cabinet, Quartz/Granite countertops, blinds, patio slider. Flex room w/french doors can be used for a dining room/office/guest room. New tiled shower in primary bath, double vanities, walk in closet & separate water closet. Spacious bedrooms, hall bath features new tub shower surround, laundry closet on second floor. New Full bath on 1st floor. Modern finishes throughout. New HVAC system, roof replaced in 2022. Backyard features deck/shed & view of the community lake. Convenient to shopping, interstate, & bases. Enjoy activities hosted by the HOA to include a pool, playgrounds, & clubhouse.

449 Sawyers Mill Crossing, South Chesapeake

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

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

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

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

208 Pine Island Quay, South Chesapeake
$713,000
5 Beds ⋅ 3.1 Baths ⋅ 10632113 MLS
Spacious, elegant, & beautifully maintained, this all-brick home in the highly sought-after Grassfield High School district offers the perfect blend of luxury, comfort and functionality. Featuring 5 generously sized bedrooms, including 2 primary suites and 3 en-suite bathrooms. The gourmet kitchen is a chef's dream, complete with granite countertops, a gas cooktop, double ovens, brand-new refrigerator, new dishwasher, and abundant cabinetry. The open-concept layout flows seamlessly into the living room with soaring cathedral ceilings, custom built-ins, & so much natural light. Enjoy the stunning sunroom and a screened in porch with easy breeze windows, great for year-round enjoyment. Step outside to your private backyard retreat featuring a beautiful brick paver patio, built-in fire pit, and professionally landscaped grounds. A charming front porch welcomes you home while the new 2nd floor HVAC adds peace of mind. A rare opportunity in one of Chesapeake's most desired communities!

208 Pine Island Quay, 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.

How much is your home worth?

Get instant property value now!