Refine Search
Sort by
801 Keeling Drive, South Chesapeake
$695,000
4 Beds ⋅ 3.1 Baths ⋅ 10661449 MLS
Looking for room to grow, space to gather, and a backyard made for memories? Welcome to Cheshire Forest in the heart of Great Bridge! This beautifully maintained 4-bedroom, 3.5-bath home offers over 3,100 sq ft, gorgeous oak hardwood floors, and NO CARPET throughout. The updated open-concept kitchen is the heart of the home, complemented by formal dining, a flexible living room or study, a family room with fireplace, and a spacious primary suite with its own fireplace. Picture it: summer cookouts, pool days, and evenings on the expansive deck overlooking a fully fenced backyard with a heated in-ground pool. Big-ticket updates include a new pool liner (2025), upstairs A/C (2024), refinished hardwoods, and updates to the roof, gutters, garage door, and HVAC. A two-car garage and neighborhood clubhouse, pool, playground, and tennis courts complete the picture. Your next chapter starts here!

801 Keeling Drive, South Chesapeake

1060 Butte Lane, South Chesapeake
$479,900
4 Beds ⋅ 3.1 Baths ⋅ 10661327 MLS
Ready NOW-Model Home for sale!! Luxury End Unit townhome condo w/rear load 2 car garage. 2nd floor covered front deck overlooking open space and lake view. Covered entry, fenced front yard w/gate to multi trail and easy access to mail pavillion & guest parking.Luxury LVP,2nd Floor:Kitchen GE stainless appliances including refrigerator,pantry,center island w/shiplap pull out double trash, living area linear fireplace w/shiplap and built ins,office/flex room,dining area.1st floor:Br/ flex room,hall bath,mudroom.3rd floor:Primary bedroom,ceramic shower,dual sinks, linen closet, laundry room. Quartz tops kitch,all baths,wood shelving all closets.Pet Friendly.Quiet easy lifestyle with the comfort of quality construction & name brand building materials including James Hardie Fire Retardant Fiber Cement Board.Builder 2-10 home warranty, master insurance,trash pick up,private streets,city water/sewer, multipurpose trails with lake and fountain.End Corner Unit.Mortgage Incentives.

1060 Butte Lane, South Chesapeake

1235 Damyien Arch, South Chesapeake
$265,000
3 Beds ⋅ 2 Baths ⋅ 10661062 MLS
Don't miss this inviting end-unit townhome offering the perfect blend of comfort, space, and convenience! Welcome home to an open-concept living, dining, and kitchen area featuring granite countertops and stainless steel appliances, creating an ideal space for everyday living and entertaining. Enjoy the added privacy and outdoor space of a generously sized backyard, perfect for relaxing, hosting guests, or enjoying time outdoors. Upstairs, you'll find three well-appointed bedrooms, including a spacious primary suite with a private en-suite bath. Conveniently located with easy access to major interstates, shopping, military bases, and more, this home checks all the boxes. Don't wait—schedule your private tour today and make this home yours just in time for the holidays!

1235 Damyien Arch, South Chesapeake

301 Sikeston Lane, South Chesapeake
$449,000
4 Beds ⋅ 3 Baths ⋅ 10660542 MLS
Welcome home to this luxurious 4-bed, 3 full bath home located in the highly sought-after Great Bridge school district. The open floorplan is enhanced by 9-foot ceilings on both levels, recessed lighting, and plenty of natural light. The kitchen serves as the heart of the home, offering a large island, quartz countertops, and stainless-steel appliances— for both entertaining and everyday living. Upstairs, enjoy freshly installed carpet throughout, convenient upstairs laundry room, and a spacious primary suite that features both a generous walk-in closet and spa-like bathroom complete with a soaking tub, oversized shower, and double vanity. Additional highlights include a covered porch, relaxing back patio, and attached garage with extra driveway parking. Conveniently situated near interstates, shopping, schools, and military bases, this home combines modern style with low-maintenance living—an ideal opportunity to own in one of Chesapeake’s most desirable communities!

301 Sikeston Lane, South Chesapeake

720 Paula Drive, South Chesapeake
$670,000
5 Beds ⋅ 3.1 Baths ⋅ 10659692 MLS
Endless possibilities on over 3 acres! Bring your vision and transform this spacious 5-bedroom, 3.5-bath home your own! Offering both upstairs and downstairs primary suites and approximately 3,900 square feet of living space, this property is bursting with potential and features multiple living and entertaining areas, providing plenty of room to spread out and create your dream home. Situated on over 3 acres of beautiful wooded land, the possibilities are endless! The expansive property features the footprint of a former swimming pool, along with an existing brick pool equipment building, offering potential for a future backyard oasis. A separate 320-square-foot workshop with electricity provides excellent space for hobbies, projects, or additional storage. Whether you envision a private wooded retreat, space for gardening, agricultural pursuits, potential livestock use, or simply room to roam and explore, this unique property offers an incredible opportunity to bring your ideas to life. With abundant space both inside and out, this is your chance to create something truly special!

720 Paula Drive, South Chesapeake

1312 Woodview Lair, South Chesapeake
$715,000
4 Beds ⋅ 3.1 Baths ⋅ 10660380 MLS
Welcome to 1312 Woodview Lair a beautiful all-brick home in Chesapeake's desirable Grassfield area! This spacious home offers an open floor plan with hardwood flooring throughout the first floor, a formal dining room with butler's pantry, private office with French doors, and a welcoming family room with custom built-ins and gas fireplace. The kitchen features granite countertops, stainless appliances, center island, breakfast bar, and new refrigerator and stove. The primary suite offers a sitting area and completely remodeled bathroom. Additional bedrooms include a Jack & Jill bath and second primary suite with private bath. Recent improvements include fresh paint throughout most of the interior and a new pool liner, salt cell, and pump in 2025–2026. Enjoy the backyard saltwater pool, stamped concrete patio, and nearby walking trails. Convenient to shopping, dining, and major commuter routes!

1312 Woodview Lair, South Chesapeake

543 Bright Red Run, South Chesapeake
$399,900
3 Beds ⋅ 2.1 Baths ⋅ 10660236 MLS
Immaculately maintained, this 2022 Craftsman-style end-unit townhome is in the sought-after Grassfield School District. The open-concept layout features a light-filled Great Room & gourmet kitchen with Quartz countertops, white shaker cabinetry, stainless steel appliances, gas range, oversized breakfast bar, & pantry. LVP flooring spans the first floor. Upstairs, the spacious primary suite boasts a double tray ceiling, walk-in closet, & en-suite bath with dual vanity & oversized tiled shower with built-in bench. Two additional bedrooms, 2.5 baths, laundry room, tankless water heater, and all appliances convey. Enjoy outdoor living on the patio, just a short distance from community amenities including walking trails, playground, dog park, splash pad, & covered pavilion. Ground maintenance included. Convenient to shopping, dining, military installations, & major interstates. Assumable VA loan at an attractive 3.5% interest rate; Loan can only be assumed by a VA eligible buyer! Call for details.

543 Bright Red Run, South Chesapeake

1400 Dons Way, South Chesapeake
$529,900
4 Beds ⋅ 3.1 Baths ⋅ 10660222 MLS
Immaculately maintained & better than new, this stunning end-unit townhome in Greenbrier is move-in ready! The entry level offers a 1-car garage, bedroom, full bath, flex room, mudroom with built-ins, & access to the fenced patio. The main level features an open-concept design with a sun-filled Great Room, electric fireplace, dining area, & gourmet kitchen boasting Quartz countertops, white shaker cabinetry with under-cabinet lighting, stainless steel appliances, oversized breakfast bar, & large pantry. Durable LVP flooring spans the first and second levels. The third-floor Primary Suite includes a spacious walk-in closet & private bath with dual vanities, Quartz counters, & a tiled shower. Two additional bedrooms, a full bath, & laundry complete the upper level. All appliances convey. Conveniently located near Greenbrier Mall, dining, medical facilities, military installations, interstates, and tunnels. *Assumable 5.75% VA loan available; Loan can only be assumed by a VA eligible buyer. Call for details.

1400 Dons Way, South Chesapeake

1451 Rollesby Way, South Chesapeake
$330,000
2 Beds ⋅ 2.1 Baths ⋅ 10660184 MLS
Lovely 2 primary bedroom condo with an extra room on the 1st floor in the lovely Greenbrier area. Lot's of upgrades throughout and very well cared for. A better deal than todays new construction! Newer LVP flooring on the 1st floor and newer plush carpet on the 2nd floor. Lovely kitchen with stainless appliances and solid surface countertops. Newer updated paint throughout. Priced to sell quickly! Condo fee of $387 covers water, sewer, trash pick up, landscaping, access to the neighborhood pool, and even the roof maintenance. This area is super convenient to the mall, golf course, bases, shopping, schools, churches and just a short way to the interstate. An awesome place to call home! Beautiful easy care living. Don't miss this beauty!!!

1451 Rollesby Way, South Chesapeake

609 Edgewood Arch, South Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10660136 MLS
Nestled in one of the area's most desirable neighborhoods, this stunning home offers over 3000 sq ft of beautifully designed living space. Step inside to an inviting floor plan featuring a spacious living room with soaring cathedral ceilings and a gorgeous stone fireplace. The large eat in kitchen flows seamlessly to the living area with ample cabinetry, a brand-new kitchen sink, plenty of space for entertaining. This spacious 4-bedroom home also features a versatile flex room off the foyer, great for a home office or den. Retreat to the expansive primary suite through French doors, where you will find a generous walk-in closet & a en-suite bath designed for comfort and relaxation. All new windows 2024 and a new HWH. Outside, you'll love the newer deck and fenced in yard. Cheshire Forest residents enjoy exceptional lifestyle amenities including a neighborhood pool, the flying fish swim team, clubhouse, playgrounds, tennis & pickleball courts, pond for fishing & scenic walking paths.

609 Edgewood Arch, South Chesapeake

2214 Averill Drive, South Chesapeake
$629,000
4 Beds ⋅ 3 Baths ⋅ 10659880 MLS
Enjoy spacious living in this 4-bedroom, 3-bath brick ranch on a corner lot in Chesapeake’s established Marsh Creek neighborhood. Cathedral ceilings, hardwood floors, and a gas fireplace welcome you into the main living area, which opens to a kitchen with granite countertops, two pantries, and new stove, microwave, and refrigerator. The first-floor primary suite features a large closet and a spacious bath with dual sinks, a jetted tub, and a separate shower. A finished room over the garage with a full bath offers flexibility as a fourth bedroom, guest retreat, or recreation space. The oversized three-car garage provides ample room for parking and storage. Outside, enjoy a fenced backyard, two-level deck, pergola, and in-ground irrigation. No HOA in Grassfield School District!

2214 Averill Drive, South Chesapeake

817 Wickford Drive, South Chesapeake
$260,000
3 Beds ⋅ 2 Baths ⋅ 10658699 MLS
3 BEDROOM 2.0 BATH SINGLE STORY END UNIT TOWNHOME. LIVING ROOM LAMINATE WOOD FLOOR, BOOKSHELVING, LIGHTED CEILING FAN AND BRICK FIREPLACE. OPEN DINING AREA TO THE UPDATED KITCHEN, BREAKFAST BAR AREA, STAINLESS APPLIANCE PACKAGE, REFRIGERATOR, SMOOTH TOP STOVE, BUILT IN MICROWAVE/DISHWASHER, DOUBLE STAINLESS SINK. PRIMARY SUITE LIGHTED CEILING FAN AND WALK-IN CLOSET. PRIMARY BATH RAISED VANITY TUB/SHOWER. LAUNDRY AREA CABINET AND SHELVES. TWO ADDITIONAL BEDROOMS, FULL HALL BATH, TUB/SHOWER, MARBLE TOP VANITY, LVP PLANK FLOOR, MEDICINE CABINET AND OVAL MIRROR. FEATURES: NEW ROOF, NEWER PAINT AND FLOORING, DIGITAL AC THERMOSTAT, UPGRADED BLINDS, CEILING FANS, STORMDOOR, PRIVACY FENCED BACKYARD, PATIO, TREES, STORAGE SHED, SIDE BY SIDE DRIVEWAY PARKING. AVAILABLE FOR QUICK CLOSING.

817 Wickford Drive, South Chesapeake

1900 Briton Lane, South Chesapeake
$635,000
4 Beds ⋅ 2.1 Baths ⋅ 10658981 MLS
Welcome Home to Hickory Manor’s sought-after Bentley model, packed with upgrades! This 4-bedroom, 2.5-bath home features a first-floor office with built-in cabinetry, 50A Tesla EV charger, and generator hookup. The kitchen shines with quartz countertops, two-tone cabinetry, Samsung Bespoke appliances, and a gas range. Light-toned LVP flooring adds warmth and style throughout the downstairs and primary bedroom. Enjoy the oversized 15x25 screened porch with vaulted ceiling for relaxing or entertaining, plus an adjoining concrete patio. The 16x8 outbuilding features a finished 12x8 workshop with 100A power, separate storage space, and an additional lean-to shed for extra storage. Enjoy community amenities: pool, fitness room, clubhouse, and playgrounds. Modern upgrades, versatile spaces, and exceptional indoor-outdoor living make this home a must-see!

1900 Briton Lane, South Chesapeake

408 Wenger Road, South Chesapeake
$624,900
4 Beds ⋅ 2.1 Baths ⋅ 10658823 MLS
Prepare to fall in love with this well maintained home sitting on 1.63 acres. Viwinco impact-resistant windows with sound reduction, gas tankless water heater, gas grill hookup, new refrigerator, new water system and so much more! Spacious living space and generously sized bedrooms and bathrooms. 1,232-square-foot metal pole barn with 3 garage doors, a separate meter, multi 220 outlets, a heater, and an air compressor. It's perfect for someone who needs a separate workshop or storage for extra vehicles and boats. The possibilities are endless! Septic has been maintained regularly by R & K. Seller also has a netted batting cage available for installation! Convenient country living! Excellent school district!

408 Wenger Road, South Chesapeake

471 San Roman Drive, South Chesapeake
$324,900
3 Beds ⋅ 1.1 Baths ⋅ 10658841 MLS
Welcome to this updated 3-bedroom townhome in the Grassfield school district! Situated on a spacious corner lot, this home offers a generous fenced backyard with room to create your own outdoor retreat. Inside, enjoy quartz countertops in the kitchen and bath, updated flooring, fresh interior paint, and brand-new upstairs carpet. The living area features a cozy fireplace, while the bright breakfast area offers a welcoming place to start your day. The primary bedroom connects to the hall bath and includes its own vanity area with a sink and closet. The tub has also been resurfaced. A newer deck expands your outdoor living space, and the storage shed conveys. Convenient to shopping, dining, and major roadways!

471 San Roman Drive, South Chesapeake

707 River Gate Court, South Chesapeake
$674,900
5 Beds ⋅ 2.1 Baths ⋅ 10658800 MLS
Convenient location. 20 min to Downtown Norfolk. 35 min to NAS Oceana, Dam Neck & beaches. 20 min to Norfolk Int Airport. Over 10 grocery stores in a 5 mile radius. 5 min to Hickory H.S., 1 of the BEST in Hampton Roads. Easy access to Chesapeake Bypass, I-64, I-264, & I-464. This property is a gardener's dream sequenced for near year round color. Back yard oasis includes a hot tub, goldfish pond and six foot privacy fence. Two patios are connected by a master-crafted paver walk-way. Oversized garden shed helps keep garage clutter free. In ground sprinkler system fed by well water to keep watering cost low. Two outdoor water taps fed by the well & two additional taps fed by city water. Tank-less water heater provides endless hot water. The oversized Primary Bedroom includes two walk in closets. One large walk-in closet features two side cubby units for storage. The other walk-in closet is medium sized with plenty of storage space. Washer & dryer are on the second floor for convenience to bedrooms. Some photos are AI-virtually staged.

707 River Gate Court, South Chesapeake

461 Gloria Drive, South Chesapeake
$500,000
5 Beds ⋅ 3 Baths ⋅ 10658716 MLS
Spacious brick rancher offering 5 bedrooms and 3 full baths with an abundance of living space and approximately $250,000 in improvements over the past 13 years! The home features a living room, formal dining room, and inviting family room with fireplace. The kitchen offers granite countertops and plenty of cabinet space. The primary suite includes a private bath and walk-in closet, while the finished room over the garage provides additional flexibility for a home office, recreation room, or guest space. Enjoy outdoor living on the large covered deck overlooking the above-ground saltwater pool and fenced backyard. Additional highlights include an oversized attached 1-car garage and an oversized detached 2-car garage with workshop, valued at approximately $60,000. With generous space, extensive improvements, and exceptional garage and workshop space, this property offers plenty to appreciate!

461 Gloria Drive, South Chesapeake

905 Camp Street, South Chesapeake
$599,000
4 Beds ⋅ 3.1 Baths ⋅ 10658354 MLS
A Community with year-round events, clubhouse, pool, playgrounds and a brand NEW school scheduled to open in 2027, that would be Culpepper Landing in Chesapeake! The BEST part is this like new home, built in 2021 & meticulously maintained! It offers 4 Bedrms, 3 1/2 Bath, almost 2,500 sqft of open, bright natural light, living space. A FROG that is private off of the kitchen w/its own full bath & walk-in closet, could be used as multi-generational liv'g as an In-law Suite, or flex space. A Large eat-in kitchen w/custom cabinets, an abundance of storage, granite counters, SS appliances, & an XL island perfect for a family & entertaining. Upstairs you'll find a large laundry room, primary bedroom w/tray ceiling, ensuite bath, & walk-in closet it truly is your own peaceful retreat. A 3rd full bath & 2 large bedrooms upstairs give you a very versatile layout. Relax in fenced in backyard, this home was designed for everyday living w/plenty of room to spread out! Min from shopping/interstates

905 Camp Street, South Chesapeake

2630 Cecilia Terrace, South Chesapeake
$474,900
4 Beds ⋅ 2.1 Baths ⋅ 10657960 MLS
This beautiful property sits on a huge, fully fenced corner lot in a quiet neighborhood within the highly desirable Grassfield School District! This open and bright home features a spacious primary bedroom with multiple closets, separate dining room, a good-sized kitchen with a gas stove, and two beautifully updated bathrooms. Enjoy outdoor living on the large deck overlooking the expansive yard. The oversized room over the garage offers endless possibilities as a fourth bedroom, second family room, game room, or media room. Located in an amazing neighborhood, this home offers convenient access to shopping, major highways, and military bases. Space, comfort, and location make this home a must-see!

2630 Cecilia Terrace, South Chesapeake

1266 Auburn Hill Drive, South Chesapeake
$725,000
5 Beds ⋅ 3 Baths ⋅ 10657857 MLS
Experience refined comfort in sought-after Albemarle River! Tucked away on a beautiful corner lot yet near I-64, shopping, dining, & all Greenbrier has to offer, this exceptional one-owner Craftsman home has been meticulously maintained. Beautiful Craftsman trim, columns on front porch, hardwood floors, & an inviting open floor plan create a warm, elegant feel. The kitchen features Cortez countertops and stainless-steel appliances. The expanded primary suite offers a custom dream closet & spa-inspired bath with dual vanities, walk-in shower, & oversized soaking tub. The FROG offers flexible space for a 4th bedroom, office, or media room. Step outside to your private backyard oasis with a sparkling heated saltwater in-ground pool, & plenty of room to entertain. Beautifully cared for and move-in ready, this is the one you've been waiting for!

1266 Auburn Hill Drive, South Chesapeake

1125 Sir Gawaine Drive, South Chesapeake
$360,000
4 Beds ⋅ 2.1 Baths ⋅ 10658020 MLS
Welcome home to this charming Chesapeake property offering comfort, functionality, and space to grow. Enjoy peaceful mornings and quiet evenings from the charming covered porch, an ideal extension of the home's living space. This traditional home features a fenced backyard ideal for entertaining, pets, or play, along with a patio for relaxing evenings outdoors. Inside, you'll find thoughtful living spaces including a breakfast area, pantry, utility room, and a converted garage that provides flexibility for a home office, playroom, guest space, or hobby room. Located in an established neighborhood with easy access to shopping, dining, and major commuter routes. Don't miss your chance to make this Chesapeake home your own!

1125 Sir Gawaine Drive, South Chesapeake

938 Olmstead Street, South Chesapeake
$630,000
5 Beds ⋅ 3.1 Baths ⋅ 10657755 MLS
Gorgeous & 4-years-young in community-friendly Culpepper Landing with scenic outdoor areas, clubhouse & pool! Huge open & bright floor plan enhanced by classic neutral décor. Enjoy flexible living spaces great for home office, study, dining room or homeschool station. Dreamy kitchen with an abundance of cabinetry, counter space & massive breakfast bar great for gathering & entertaining. Inviting family room sits at the heart of the home & opens to covered porch overlooking fenced backyard. Extra highlights include a convenient mudroom, organization area & finished room over the garage with full bath offering endless possibilities for a guest suite, media room or private retreat. With 5 bedrooms & 3.5 bathrooms, there's plenty of room for everyone to spread out. Elegant primary suite features exercise area, walk-in closet, dual-sink vanity & oversized shower with double shower heads. This is the Total Package & Across the street from brand NEW elementary school opening 2027-2028.

938 Olmstead Street, South Chesapeake

1324 Cambridge Way, South Chesapeake
$595,000
4 Beds ⋅ 2.1 Baths ⋅ 10657862 MLS
Welcome to this truly custom-built home in the highly desirable Hunningdon Woods neighborhood nestled in the heart of Greenbrier! Situated on a beautiful corner lot, this charming home offers a wonderful blend of comfort, character, and thoughtful design. The inviting living area flows into a lovely eat-in kitchen, creating the perfect setting for everyday living and entertaining. The spacious first-floor primary suite offers comfort and convenience, while the generously sized other bedrooms provide plenty of room for family or guests. Enjoy relaxing on the screened porch overlooking a beautifully landscaped yard filled with absolutely stunning array of blooming perennials that provide color and beauty throughout the seasons. Complete with a side-load garage, this special home offers timeless appeal. A wonderful opportunity to make this exceptional property your own.

1324 Cambridge Way, 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!