Refine Search
Sort by
1805 Dockwood Trail, West Chesapeake
$380,000
3 Beds ⋅ 1.1 Baths ⋅ 10657429 MLS
Opportunity awaits in the desirable Western Branch area of Chesapeake! This 3-bedroom, 1.5-bath home is full of potential and ready for its next chapter. With solid bones and a little TLC, this property offers a wonderful opportunity to make it your own. The spacious family room leads to an impressive four-season room, providing additional space to relax, entertain, or simply enjoy the backyard views year-round. Situated on a generously sized lot, there's plenty of room to create your own outdoor retreat. Conveniently located near shopping, dining, and everyday amenities. Schools include Edwin W. Chittum Elementary, Jolliff Middle, and Western Branch High. Whether you're looking for a home to personalize or your next investment opportunity, bring your vision and discover the possibilities this property has to offer!

1805 Dockwood Trail, West Chesapeake

1108 Cumberland Court, South Chesapeake
$600,000
4 Beds ⋅ 3 Baths ⋅ 10657974 MLS
Welcome to 1108 Cumberland Ct, a beautifully staged Chesapeake home with a pool and a fenced backyard made for entertaining. Inside, enjoy bamboo flooring and premium crown molding throughout the main level. The kitchen features granite counters, tiled backsplash, a pocket door, a gas range (2022), a 2024 dishwasher, and whole-house plus reverse-osmosis water filtration. A full downstairs bath with a walk-in shower adds convenience, and the wood-burning fireplace is perfect for cool evenings. Major updates include roof and skylights (2015), gas furnace and A/C (2017), front windows (2020), and an encapsulated crawl space with new vapor barrier (2022). Walk-in attic, garage shelving, and comfort-height toilets. Open house Saturday, 10/17. Schedule your showing today!

1108 Cumberland Court, South Chesapeake

810 Hedgerow Court, South Chesapeake
$675,000
5 Beds ⋅ 3 Baths ⋅ 10657871 MLS
Well maintained all brick home with 2-car side loading garage, long driveway, 1/3 acre beautifully landscaped lot, situated on a cul-de-sac in Great Bridge. Open floor plan features huge kitchen with quartz countertops and overlooks fam room. FR has wood burning FP which is also plumbed for gas. In addition to the 5 bedrooms on 2nd floor, there is a 6th bedroom/office with adjacent full bathroom on 1st floor. Recent updates include 2nd floor 3 ton HVAC (Sept 2026), new carpets (Sept 2026), windows, roof, water heater, garage door, leaf filter gutters, more. Award winning Cheshire Forest community amenities include clubhouse, pool, tennis/pickle ball courts, parks and playgrounds. Screened porch with concrete floor overlooks the beautiful backyard. Seller to provide clear Termite/Moisture letters and 1 year home warranty.

810 Hedgerow Court, South Chesapeake

2711 Lake Drummond Cswy, South Chesapeake
$625,000
4 Beds ⋅ 2.1 Baths ⋅ 10657073 MLS
** INCREDIBLE OPPORTUNITY ** An exceptional combination of space, privacy and versatility awaits on nearly 4 acres with this beautifully refreshed 4-bedroom, 2.5-bath home! Has the following FEATURES: Freshly Painted throughout, Large Family Room with a Wood Burning Fireplace, New LVP Flooring, Great Kitchen with a Full Stainless Steel Appliance Package, wrap around bar and Eat-In Breakfast Area, Formal Dining Room and MORE!! Additional HIGHLIGHTS: 4 comfortable Bedrooms along with a LARGE FROG (Finished Room Over Garage) that offers exceptional versatility as possible media or recreation room, home office, playroom, hobby space, guest area or whatever best suits your needs, 2 Car Attached Garage, generous rear deck provides an ideal setting for morning coffee, afternoon relaxation or memorable gatherings with family and friends. Step outside and discover the true appeal of this expansive nearly 4-acre property. There's plenty of room to enjoy the peaceful surroundings, entertain outdoors, garden, play, accommodate pets or simply relax and enjoy the privacy and freedom that come with owning a larger homesite. With its beautiful setting, spacious living areas and nearly 4 acres of land, this is a rare and truly special opportunity that offers the space, flexibility and lifestyle you've been looking for!

2711 Lake Drummond Cswy, South Chesapeake

628 Gladesdale Drive, South Chesapeake
$499,900
4 Beds ⋅ 2 Baths ⋅ 10657378 MLS
Well maintained all brick ranch on a large .34 acre corner lot in the Hickory School District . Enter the large greatroom through foyer which opens to formal dining room. Greatroom features chairrail, wainscoating, exposed beams, built in bookcase and masonry wood burning fireplace.Kitchen has been updated with new cabinet faces, countertops and laminate floors; all appliances convey. Primary bath updated with new vanity, toilet and has tile floor. Hall bath updated with new toilet. Laundry closet convenietly off eat-in area in kitchen. Large frog has plenty of head space and large closet; partially floored walk in attic. HVAC, hot water heater newer, encapsulated crawl with dehumidifier. Large deck off greatroom. No neighborhood fees.

628 Gladesdale Drive, South Chesapeake

443 Supplejack Court, South Chesapeake
$484,000
4 Beds ⋅ 2 Baths ⋅ 10657404 MLS
Welcome to sought-after Riverwalk! This beautifully maintained 4-bedroom, 2-bath ranch sits on a desirable corner lot with great curb appeal. The freshly painted interior offers an inviting floor plan, vaulted ceilings, updated lighting, luxury vinyl plank flooring, and thoughtful custom touches, including enhanced closet space and added shelving. The kitchen features quartz countertops, stainless steel appliances, and two pantries. A versatile 4th bedroom/FROG above the 2-car garage offers flexible space for guests, an office, or hobbies. Enjoy the beautifully landscaped backyard with a deck and paver patio, perfect for outdoor entertaining. Riverwalk amenities include a clubhouse, pool, dock, boat ramp, playground, trails, tennis and pickleball courts, plus seasonal concerts and food trucks. Discover the charm, convenience, and lifestyle that make Riverwalk a wonderful place to call home!

443 Supplejack Court, South Chesapeake

3616 Riverwood Crescent, South Chesapeake
$749,000
4 Beds ⋅ 3 Baths ⋅ 10657714 MLS
COUNTRY LIVING AT ITS BEST!Imagine sipping your morning coffee while deer graze in your backyard! This incredible 3-acre property in desirable Hickory/Grassfield offers privacy, space, and endless possibilities!2,200 sq ft home with 4 bedrooms and 3 fully renovated bathrooms, a cozy wood-burning fireplace, new waterproof laminate flooring throughout, and a 2-car attached garage.The 1,500 sq ft heated workshop features a vehicle lift, compressor — perfect for car enthusiasts, hobbies, or business needs! Enjoy one of the largest above-ground pools available, extensive decking, and a recently repaired and painted shed. Additional features include newer HVAC and appliances, an ivwr thw top water softener, and a sealed crawlspace with dehumidifier and warranty. Not in a designated flood zone! Three acres, a spacious heated workshop, and your own private backyard oasis in the sought-after Hickory/Grassfield school district!Country charm, modern comforts, and room to live your way!

3616 Riverwood Crescent, South Chesapeake

911 Charing Cross, South Chesapeake
$535,000
4 Beds ⋅ 2.1 Baths ⋅ 10655533 MLS
Welcome to this beautiful four-bedroom, 2.5-bath home in the desirable Tunbridge Station neighborhood of Great Bridge! With nearly 2,600 square feet of living space, this home offers plenty of room to live, relax, and entertain. Situated on a spacious corner lot in a quiet neighborhood, this home features wood flooring throughout the first floor and new LVP flooring on the second floor. The kitchen offers a cozy eat-in area with a bay window, while the separate living room provides added privacy and could also serve as a home office. A formal dining room offers the perfect space for hosting family and friends. One of the home's standout features is the oversized family room over the garage, offering endless possibilities for a media room, game room, or playroom. Enjoy outdoor living with a new deck and patio for relaxing or entertaining. Located in the sought-after Hickory school district, this home offers space, versatility, and a wonderful opportunity to enjoy all that Great Bridge has to offer.

911 Charing Cross, South Chesapeake

901 Summerfield Crescent, South Chesapeake
$475,000
4 Beds ⋅ 2.1 Baths ⋅ 10657121 MLS
Fully updated and move-in ready, this spacious 4-bedroom (potentially 5), 2.5-bath home offers plenty of room to spread out! The downstairs primary suite is a true retreat, featuring a generous bedroom and ensuite designed to feel like your own private escape. Double vanity, jetted tub, separate stand-alone shower & toilet room and huge walk-in closet! The remodeled kitchen shines with brand-new cabinets, new granite countertops, and stainless-steel appliances, while fresh paint, new carpet, and all-new fixtures throughout give the entire home a clean, modern feel. Upstairs, you’ll find three additional bedrooms plus a versatile loft space that could easily be converted into a 5th bedroom, home office, playroom, or flex space. With updates throughout and a functional layout, this home offers space and flexibility. This corner lot condo provides low maintenance living with the space and privacy of a single-family home. Located nearby shopping, dining, great schools, major roadways & everyday conveniences, you’ll have everything you need just minutes from home!

901 Summerfield Crescent, South Chesapeake

5 Lydney Circle, Central Chesapeake
$320,000
3 Beds ⋅ 1.2 Baths ⋅ 10657187 MLS
Saturday night on a big back deck, dinner from a kitchen where every appliance is new, and not a single project on the to-do list. This Ipswich townhouse in Chesapeake has been refreshed top to bottom with fresh exterior paint, all-new windows that pour in light, and new flooring throughout. The kitchen feels brand new, and plates go straight out to the deck as the evening cools down. Upstairs, all three bedrooms share one level, leaving the main floor open for everyday living. The updated Jack-and-Jill bath is designed for busy mornings: two private toilet-and-sink rooms connected by a shared tub/shower. A newer roof and newer water heater mean the big-ticket items are handled before the first box is unpacked. Spend summer afternoons at the community pool, then head out on the walking and biking trails in the park just behind it. New windows, new floors, new appliances, fresh paint. The only project left here is deciding where the couch goes. Come see 5 Lydney Circle. Some photos were virtually staged using AI.

5 Lydney Circle, Central Chesapeake

2309 Drum Creek Road, West Chesapeake
$439,900
4 Beds ⋅ 2 Baths ⋅ 10656969 MLS
Beautifully renovated brick ranch tucked away on a quiet street and situated on an impressive .69-acre lot! This move-in-ready 4-bedroom, 2-bath home shows beautifully with fresh paint and hardwood floors throughout. The open floor plan features a spacious great room centered around a traditional wood-burning fireplace, creating a warm and welcoming space. The updated kitchen offers shaker-style cabinetry, granite countertops, upgraded stainless steel appliances, and plenty of room for everyday living and entertaining. Spacious bedrooms and beautifully renovated bathrooms add to the appeal. The converted garage provides incredible flexibility and could easily serve as a 4th bedroom, home office, playroom, gym, or additional living space. Enjoy the perfect combination of an updated home, generous lot size, and a peaceful setting!

2309 Drum Creek Road, West Chesapeake

1306 Virginia Avenue, Central Chesapeake
$409,000
5 Beds ⋅ 2.1 Baths ⋅ 10657160 MLS
Stunning 5-Bedroom Home with an Assumable 2.75% VA Loan! Beautifully remodeled from top to bottom, this 5 bedroom, 2.5 bath home features an open floor plan, updated kitchen with granite countertops, custom vaulted ceilings, sunroom, wood-burning fireplace, updated bathrooms, and tankless gas water heater. Rare financing opportunity! Qualified buyers may be able to assume the existing 2.75% VA mortgage with an approximate balance of $202,668. The estimated equity difference is $215,832 based on the $418,500 asking price. Cash or additional approved financing may be used to cover the difference. Allow 45+ days for lender approval and processing. Conveniently located in historic South Norfolk, near interstates, shopping, downtown, military bases, and shipyards. Beautiful updates, great location, and an opportunity you don’t want to miss!

1306 Virginia Avenue, Central Chesapeake

1508 Bayberry N Court, South Chesapeake
$455,000
3 Beds ⋅ 2 Baths ⋅ 10657060 MLS
Welcome home to this beautiful ranch tucked away on a quiet cul-de-sac in a desirable Chesapeake location! This well-maintained home offers comfortable one level living, a spacious lot, and a long list of recent updates. Inside, the home features updated bathrooms, new carpet in the living room, and a welcoming living space with a fireplace and large sliding glass doors overlooking the backyard. Major updates include a new AC unit (2021), new roof, soffit and gutters (2023), new siding (2025), front door (2026) and new crawlspace insulation (2026). The two-car garage provides ample storage. Ideally located near Greenbrier’s shopping, dining, entertainment and recreational amenities, with easy access to I-64, beaches and Naval bases. A peaceful cul-de-sac setting combined with a private backyard and convenient location makes this a home you won’t want to miss!

1508 Bayberry N Court, South Chesapeake

2448 Johnstown Road, South Chesapeake
$624,900
4 Beds ⋅ 2 Baths ⋅ 10657067 MLS
Enjoy the tranquility of this charming ranch nestled on a private lot spanning nearly 3 acres. The inviting floor plan welcomes you with a cozy living room featuring a fireplace and wet bar, creating a great space to relax or entertain. At the heart of the home, the kitchen is filled with natural light from two large windows and offers ample cabinet and counter space, along with stainless steel appliances. Just off the kitchen, the dining area allows for effortless gatherings and everyday living. The spacious primary suite provides a peaceful retreat with a large walk-in closet and private ensuite bathroom. The additional bedrooms are generously sized, offering flexibility for guests, or a home office. Outside, the expansive backyard and screened porch provide endless opportunities to enjoy the surrounding natural beauty and peaceful setting. Experience the best of country living with the convenience of a short commute to shopping, dining, and everyday amenities.

2448 Johnstown Road, South Chesapeake

904 Barrington Court, South Chesapeake
$525,000
4 Beds ⋅ 2 Baths ⋅ 10657061 MLS
Welcome home! Nestled in the established Waterford neighborhood in Chesapeake's highly sought-after Great Bridge area! Situated on a spacious cul-de-sac lot, this charming 4-bedroom, 2-bath home offers the perfect combination of comfort, functionality, and location. Enjoy the convenience of single-level living with an inviting floor plan designed for both everyday living and entertaining. The spacious living areas feature a cozy fireplace, creating a warm and welcoming atmosphere. Enjoy a beautifully renovated primary bathroom, offering updated finishes and a refreshed, modern feel. Additional improvements include a recently encapsulated crawlspace equipped with two dehumidifiers, providing added moisture protection and peace of mind. Outside, the generous backyard offers plenty of space for outdoor gatherings, gardening, or simply relaxing. Located in the desirable Great Bridge School District and just minutes from shopping, dining, parks, and major commuting routes.

904 Barrington Court, South Chesapeake

3316 Kindlewood Crescent, West Chesapeake
$498,250
4 Beds ⋅ 2.1 Baths ⋅ 10657022 MLS
This charming brick colonial home is on a corner lot of a cul-de-sac in the desirable Silverwood development. The spacious 20x40 ft. pool boasts of a new liner in 2024, complemented by a brand-new back porch added three years ago and a freshly renovated front porch completed this summer. Inside, the updated kitchen shines with granite countertops, freshly painted cabinets (including upper cabinets repainted this summer), a new sink, and modern cabinet pulls. Beautiful hardwood floors grace the front half of the downstairs (recently refinished) and all of the upstairs, creating a warm and inviting atmosphere. Western Branch High School, middle school, and elementary school all located within the development, along with festive community events like the annual Holiday parade with firetruck and spring egg hunt. Restaurants, shopping all nearby and just a quick trip to downtown Norfolk, this home offers the ideal blend of comfort, updates, and community charm. Seller has recent clear Termite and Moisture reports.

3316 Kindlewood Crescent, West Chesapeake

701 New River Court Unit B, South Chesapeake
$235,000
2 Beds ⋅ 2 Baths ⋅ 10657033 MLS
Honey stop the car! Townhouse-style living w/condo convenience in Chesapeake's Riverwalk community! This 2 bedroom, 2 full bath home offers approximately 1,100 sq ft across two levels, giving you the feel of a townhome without the upkeep. Fresh paint and new LVP flooring run throughout, so it's truly move-in ready. One of the two full baths has been remodeled. The main level is built for everyday living, with a fireplace in the living room and access to a private patio for morning coffee or quiet evenings. An exterior storage room adds space for bikes, tools and seasonal gear. The condo fee covers water, sewer, trash, grounds and exterior maintenance, plus access to the community pool and clubhouse. Convenient to Greenbrier shopping, dining and medical facilities, with easy access to I-64, local military installations CALL TODAY!

701 New River Court Unit B, South Chesapeake

737 Willow Oak Drive, South Chesapeake
$560,000
4 Beds ⋅ 2 Baths ⋅ 10656926 MLS
This one checks ALL the boxes! Immaculate, beautifully updated, and exceptionally well maintained, this 4 bedroom, 2 bath Chesapeake home truly stands out. The remodeled kitchen features stainless steel appliances, a gas range and hood, beautiful countertops and backsplash, abundant cabinetry, eat-in space, and a custom butler’s pantry. Recessed lighting throughout enhances the bright, modern feel, while the inviting living room showcases beautiful hardwood floors, a large cozy fireplace, and abundant natural light. The separate dining room is ideal for everyday meals and entertaining. The primary suite features an impressive custom designed en-suite bathroom with gorgeous custom cabinetry, double vanity, and an oversized walk-in shower. Outside, enjoy a large, beautifully manicured backyard and expansive deck. An attached garage plus an impressive, detached 2 story garage provides exceptional space for vehicles, hobbies, storage, or a workshop. This home truly has it all! Now offering $10k towards closing cost or rate buy down with full price offer.

737 Willow Oak Drive, South Chesapeake

316 Tudor Place, Central Chesapeake
$434,000
5 Beds ⋅ 3.1 Baths ⋅ 10656972 MLS
Welcome to this spacious 5-bedroom, 3.5-bath home offering the size, features, and flexibility today’s buyers are looking for. With major items already in place, this property gives buyers the opportunity to add their own finishing touches while enjoying strong long-term value. The functional layout includes two ensuite bedrooms with private full bathrooms, two HVAC units for separate area comfort, a dedicated laundry room, and plenty of room for everyday living or entertaining. Outside, enjoy your own private pool, detached garage, and outdoor space made for relaxing or gathering. Conveniently located with easy access to major routes, shopping, dining, and local amenities, this home offers a rare combination of space, features, and opportunity.

316 Tudor Place, Central Chesapeake

424 Pines Of Warrick Drive, South Chesapeake
$530,000
4 Beds ⋅ 2.1 Baths ⋅ 10656970 MLS
Welcome to this exceptional Pines of Warrick residence in sought-after Great Bridge, where timeless elegance meets thoughtful modern updates. This beautifully maintained 4-bedroom, 2.5-bath home offers gracious living spaces, impressive room sizes, and a long list of improvements that make this home truly special. The renovated kitchen is a standout, featuring gorgeous custom high-end cabinetry, granite countertops, a stunning beveled ceramic subway tile backsplash, and a charming breakfast nook. Rich hardwood floors, crown moulding, and classic architectural details add warmth and sophistication throughout. The formal dining room and private library/office with French doors offer elegant spaces for entertaining or working from home. The inviting family room centers around a wood-burning fireplace (gas line remains if desired) and flows naturally into the sunroom, creating a wonderful connection to the spacious deck and large fenced backyard. The first-floor primary suite offers double closets and a beautifully remodeled en-suite bath, while the generously sized secondary bedrooms provide plenty of flexibility. Upstairs, the finished room over the garage with custom built-ins offers endless possibilities as a media room, 4th bedroom, playroom, office, or hobby space. Extensive recent improvements include TWO new zoned HVAC heat pump systems, inside and out (March 2025), a condensate drain pump with alarm (April 2025), and significant crawlspace improvements including a new vapor barrier, dehumidifier, lighting, extended access door, and sump system to divert gutter, HVAC condensate, and dehumidifier drains (2020). Additional updates include a new garage door and opener (2021) and newer dishwasher. Meticulously cared for and thoughtfully updated, this is a home that offers both character and peace of mind in one of Chesapeake's most desirable communities. Come see it for yourself—you won't want to miss this one!

424 Pines Of Warrick Drive, South Chesapeake

2024 Lisbon Road, West Chesapeake
$404,900
4 Beds ⋅ 3 Baths ⋅ 10656307 MLS
SELLER WILL PAY 2% TOWARD BUYER'S CLOSING COSTS OR RATE BUY DOWN WITH ACCEPTABLE OFFER! Enjoy easy one-level living in this beautifully updated 4BR/3BA ranch on a spacious 1/3-acre corner lot. The remodeled kitchen is the heart of the home, featuring leathered granite countertops, stainless steel appliances, new cabinetry, tile backsplash, breakfast bar, and dining area. Refinished hardwoods, fresh paint, updated fixtures, a new roof, and a new full bath add to the move-in-ready appeal. Need room to work, relax, or accommodate guests? A dedicated office with built-ins and a 4th bedroom with ensuite bath and separate entrance offer flexibility for multigenerational living, a home office, gym, or private guest suite. Utility sunroom with backyard access. Entertain on the deck beneath the gazebo, complete with electricity. Two sheds provide plenty of room for storage, tools, and hobbies. Western Branch High School district. Convenient to bases, shopping, I-664 and all that Hampton Roads has to offer!

2024 Lisbon Road, West Chesapeake

1149 Crystalwood Circle, South Chesapeake
$525,000
4 Beds ⋅ 2.1 Baths ⋅ 10656507 MLS
Welcome home to 1149 Crystalwood Circle! This inviting Chesapeake home has been thoughtfully cared for and updated over the years, offering the comfort of knowing many major improvements have already been completed. The electrical system was upgraded to 200-amp service in 2020, when the spacious 24' x 26' detached garage/workshop was added with its own 100-amp service. The HVAC received a new furnace and condenser in 2022, followed by a new washer and dryer in 2024 and a new water heater in 2025. In 2026, the home received a brand-new kitchen, new carpet, and a fully remediated crawl space with a new vapor barrier. With so much already done, there's more time to relax, enjoy your space, and make wonderful memories. Come see why this could be the one you've been waiting for!

1149 Crystalwood Circle, South Chesapeake

229 Fresno Drive, South Chesapeake
$500,000
4 Beds ⋅ 3 Baths ⋅ 10656410 MLS
This is one of those rare homes that truly supports multi gen or other uses. TRUE DETACHED in law suite with kitchenette full LARGE bath, living and bedroom, private access. The roof, paint, carpet dishwasher ALL NEW to get ready to SELL ! Just a little personalization and this could be your dream home. Its just waiting for you. Full brick, masonry fireplace, oversized deck, extra driveway and a covered parking area. City and Zillow records not reflective of the current dwelling. Three generous bedrooms plus room over the garage AND the suite make this home a winner for you! DONT DRIVE? NO PROBLEM! VERY NEAR ALL ANCILLARY SERVICES Extra nice YMCA with indoor and outdoor pool just a few short blocks. Physicians, groceries, dining and the highway system.

229 Fresno Drive, 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!