Refine Search
Map
Sort by
497 Cobblewood Bend, South Chesapeake
$227,000
2 Beds ⋅ 1 Baths ⋅ 10643240 MLS
Welcome home! This cozy 2 bedroom 1 bathroom twin home is easy to maintain and ready for a new owner! Nestled on a corner lot in the Dominion Pines neighborhood of Chesapeake, you are just minutes from highway access to bases, shopping, restaurants, and beaches. The fenced in backyard with deck provides private space for shaded quiet enjoyment.

497 Cobblewood Bend, South Chesapeake
1005 Bluebird Drive, South Chesapeake
$395,000
3 Beds ⋅ 4 Baths ⋅ 10642281 MLS
BRING ALL OFFERS! ROOF IS APPROXIMATELY 4 YEARS OLD, NEW LVP FLOORING. PROPERTY SOLD STRICTLY "AS IS, WHERE IS". THE SELLER ACQUIRED THROUGH INHERITANCE AND HAS NO KNOWLEDGE OF THE CONDITION. SELLER MAKES NO WARRANTIES, REPRESENTATIONS OR GUARANTEES, EXPRESSED OR IMPLIED REGARDING WELL, SEPTIC SYSTEM OR PROPERTY IMPROVEMENTS. BUYERS SHOULD CONDUCT INSPECTIONS AND DUE DILIGENCE. .75 ACRE LOT. SELLER TO DO NO REPAIRS!

1005 Bluebird Drive, South Chesapeake
468 Blanche Drive W, South Chesapeake
$372,000
3 Beds ⋅ 1.1 Baths ⋅ 10641756 MLS
Welcome home to this well-appreciated 3-bedroom ranch, offering comfortable one-level living and plenty of space to enjoy. The open-concept home features a cozy eat-in kitchen, a spacious den with fireplace, a separate living room, a large sunroom perfect for relaxing or entertaining, and additional outdoor patio. Recent updates include new flooring in the sunroom, fresh interior paint, new gutter covers, and a sealed attic for added efficiency and peace of mind. Roof was done in 2016, Refrigerator (2018) and dishwasher, microwave, and oven (2016). Appliances and mechanical systems have been consistently maintained through a home warranty program. This solid, well-cared-for home reflects pride in ownership and is ready for its next chapter.

468 Blanche Drive W, South Chesapeake
3127 Patrick Henry Drive, South Chesapeake
$382,000
3 Beds ⋅ 2.1 Baths ⋅ 10647714 MLS
Welcome to 3127 Patrick Henry Drive, a beautifully maintained townhome nestled in the highly desirable Culpepper Landing community of Chesapeake. Offering 1,831 square feet of thoughtfully designed living space, this immaculate home features 3 spacious bedrooms, 2.5 baths, and stylish updates throughout. The open-concept floor plan provides comfortable everyday living while offering plenty of room for entertaining. Beyond the home itself, Culpepper Landing is one of Chesapeake's premier planned communities, offering an exceptional lifestyle with resort-style amenities. Residents enjoy a community clubhouse, swimming pool, fitness center, playgrounds, nature and biking trails and more! If you've been searching for a turnkey home in one of Chesapeake's most sought-after neighborhoods, this is one you won't want to miss!

3127 Patrick Henry Drive, South Chesapeake
3145 Kenelm Drive, South Chesapeake
$370,000
4 Beds ⋅ 2 Baths ⋅ 10647914 MLS
Welcome home to this beautifully renovated 4-bedroom, 2-bath WATERFRONT property, where timeless character meets modern style. Originally built in the 1970s, this home has been thoughtfully refreshed while preserving the warmth and charm that make it truly inviting. The stunning kitchen and beautifully updated bathrooms showcase contemporary finishes, creating a move-in-ready home you’ll love from day one. Natural light pours into the spacious sunroom, offering endless possibilities for whatever best fits your lifestyle. Step outside to a large, privacy-fenced backyard that backs to the water, providing a peaceful setting for entertaining, relaxing, gardening, or simply enjoying the outdoors. With a functional layout, generous living spaces, and quality updates throughout, this home offers the perfect balance of comfort, character, and modern convenience. Schedule your private showing today before it’s gone!

3145 Kenelm Drive, South Chesapeake
104 Bishops Court, South Chesapeake
$520,000
4 Beds ⋅ 2.1 Baths ⋅ 10645829 MLS
WELCOME HOME! Tucked away on a quiet cul de sac and set on nearly an acre backing to peaceful woods, this beautifully maintained home offers the perfect blend of privacy, outdoor living, and everyday convenience. Whether you’re enjoying your morning coffee in the screened gazebo or entertaining family and friends, you’ll appreciate the peaceful setting this property provides. Inside, you’ll find stainless steel appliances, a spacious walk in pantry, a cozy gas fireplace, and thoughtful updates throughout, including a new roof installed in 2024. A transferable 2-10 Home Warranty provides added peace of mind for the next owner. Conveniently located near Interstate 64, Route 17, shopping, dining, and major military installations throughout Hampton Roads, this home offers the ideal balance of tranquility and accessibility. Don’t miss your opportunity to make this exceptional property your next home. Schedule your private showing today!

104 Bishops Court, South Chesapeake
927 Thatcher Way, South Chesapeake
$444,000
3 Beds ⋅ 2.1 Baths ⋅ 10643564 MLS
Welcome to your golfer’s paradise on the 14th hole of Greenbrier Country Club! Meticulously updated, this stunning home blends modern elegance with everyday comfort. Come into a breathtaking living area showcasing soaring cathedral ceilings, high-end LVP flooring, and massive, picturesque windows that bathe the space in natural light while framing panoramic fairway views. Retreat to the first-floor primary suite—a true sanctuary beautifully reimagined with contemporary, spa-like finishes. Enjoy the lifestyle in the heart of Chesapeake, conveniently located just minutes from premier dining and shopping. Don't miss this rare opportunity to live on the green! Seller offering a $2,500 appliance credit.

927 Thatcher Way, South Chesapeake
600 Windmill Point, South Chesapeake
$354,900
3 Beds ⋅ 2.1 Baths ⋅ 10637408 MLS
Tucked away on a quiet cul-de-sac in Chesapeake's highly desirable Cedar Lakes community, this beautiful 3-BR + Loft, 2.5-BA end-unit townhome offers 1,621 sq ft of bright, comfortable living space. This bright & airy home offers soaring ceilings and skylights that provide lots of natural light. The versatile upstairs loft includes a closet - perfect for a home office, playroom, or extra bedroom. Lots of storage space and attached 1-car garage. Easy access to the neighborhood pool and clubhouse.

600 Windmill Point, South Chesapeake
1201 Brookside Landing, South Chesapeake
$385,000
3 Beds ⋅ 2 Baths ⋅ 10651042 MLS
Well maintained 3-bed 2-bath 1,577sqft ranch home in the Greenbrier area of Chesapeake. Pride of ownership shines by big-ticket updates including all-new exterior siding, trim & wrap by Window World in 2023, LeafGuard gutters 2022 that include a lifetime warranty, architectural shingled roof & windows installed within past 6-8 years. Interior upgrades last 5 years include, a tankless water heater, hallway shower & Corian countertops. The insulated garage is equipped with an AC unit. Relax in the backyard and entertain family & guests while sitting under the pergola or the retractable awning for shaded comfort. Plenty of extra storage besides the garage to include 2 storage sheds & an attic with pull down stairs. The neighborhood boasts scenic walking trails & playgrounds. Located close to interstate, shopping & restaurants, this home is ready for its new owner to make it their own. Call today before it is GONE!!!!

1201 Brookside Landing, South Chesapeake
708 Canoe St, South Chesapeake
$564,757
4 Beds ⋅ 3.1 Baths ⋅ 10650738 MLS
**More space. More flexibility. More to love in Culpepper Landing!** If you're looking for a home that gives everyone room to spread out while still bringing people together, this one is worth a look. This 3-story home offers 4 bedrooms, 3.5 baths, and a layout that gives you room to live, work, entertain, and relax. The main level features an open kitchen and living area designed for cooking and entertaining, along with a wonderful sunroom that adds even more space to gather or simply enjoy a little quiet time. Upstairs, you'll find three bedrooms plus a spacious second living area that could be a media room, playroom, office, or whatever your lifestyle needs. The private third-floor suite includes its own full bath and offers even more flexibility for guests or a peaceful retreat. A 2-car garage, generous driveway parking, and fenced backyard round out the home. And outside your front door, Culpepper Landing offers an incredible community lifestyle with the largest community pool in Hampton Roads, clubhouse, fitness center, playgrounds, walking trails, stocked fishing ponds, dog park, and events throughout the year. Convenience matters too. Shopping, dining, major highways, and military installations are all within easy reach, making this a great location for enjoying everything Hampton Roads has to offer. **Come walk through this home and see how much space, flexibility, and opportunity it offers. You may be surprised by just how much this home has to offer.**

708 Canoe St, South Chesapeake
9.37AC Douglas Road, South Chesapeake
$250,000
10649275 MLS
Discover the possibilities on 9.37 acres in desirable Pleasant Grove! This spacious parcel offers plenty of room to build your dream home while enjoying privacy, open space, and the peaceful feel of country living. Bring your builder, your vision, and create the home you've always wanted. A wonderful opportunity to own acreage and make it your own!

9.37AC Douglas Road, South Chesapeake
3016 Aaron Drive, South Chesapeake
$375,000
4 Beds ⋅ 2.1 Baths ⋅ 10649682 MLS
Welcome home to waterfront living! Solar panels will be paid off at closing! Completely renovated in 2019, this stunning home offers the feel of new construction with modern finishes throughout. Enjoy fishing or kayaking right from your own backyard! Located in a quiet community with convenient access to the interstate, NMCP, USCG, shopping, and more. Major 2019 updates include the roof, windows, siding, and HVAC system. Move-in ready, beautifully updated, and waterfront—this home is ready for you!

3016 Aaron Drive, South Chesapeake
948 Saint Andrews Reach Unit C, South Chesapeake
$230,000
2 Beds ⋅ 2 Baths ⋅ 10648079 MLS
Beautiful 2 Bed, 2 Bath condo on a quiet street in Greenbrier! Spacious living room leads to a cozy den that has a wood burning fireplace. From the den access to a fenced in patio for entertaining and views of the lake. The kitchen offers a lot of storage. Upstairs are both large bedrooms each with sizeable closets. Some updates over the years include LVP flooring downstairs, carpet upstairs and paint throughout. Roof is around 5 years old, condo association maintains courtyard and the fees include water, trash pickup and one assigned parking space with the option of a second reserved parking space for an additional annual fee. Minutes from Greenbrier shopping, Greenbrier Country Club golf course, YMCA, Chesapeake City Park and easy access to highway.

948 Saint Andrews Reach Unit C, South Chesapeake
308 Wisdom Path, South Chesapeake
$675,000
5 Beds ⋅ 3 Baths ⋅ 10646827 MLS
Wisdom Path= Welcome to Viridian Reserve at Hickory, where comfort, space, and peaceful wooded views come together in one exceptional South Chesapeake home. From the moment you step inside, you'll be greeted by soaring cathedral ceilings, an inviting multi-landing staircase, and a warm, open layout designed for everyday living and entertaining. The spacious family room features a cozy gas fireplace, while the incredible kitchen is truly the heart of the home, offering beautiful wood cabinetry, abundant cabinet space, updated appliances, and a convenient wine/beverage refrigerator. The formal dining area provides plenty of room for gatherings, and the first floor also includes a private office, bedroom, and full bathroom—great for guests, multigenerational living, or working from home. Upstairs, the oversized primary suite is a true retreat with room for a sitting area, three closets, and a luxurious ensuite bath featuring granite countertops, dual vanities, a walk-in shower, private water closet, and an additional spacious walk-in closet. Outside, relax on the charming covered porch overlooking the backyard and peaceful wooded views, with the option to easily screen it in for year-round enjoyment. Enjoy extremely low electricity costs with a fully paid-off solar system. The oversized two-car garage offers exceptional storage, a built-in workbench, and plenty of room for hobbies, while the extended driveway provides additional parking. Located in the highly desirable Hickory area, this home offers the perfect combination of space, functionality, privacy, and energy efficiency.

308 Wisdom Path, South Chesapeake
1254 Winfall Drive, South Chesapeake
$414,000
4 Beds ⋅ 2.1 Baths ⋅ 10651925 MLS
** Easy Fixer Upper. ** Great House and Neighborhood. ** 3,000 Square Feet. ** Priced well below market value! ** ARV $615k to $625k+ ** Selling As-Is. ** No Contingencies. ** Cash Preferred. ** Excellent Opportunity for Handyman, Investor or Landlord.

1254 Winfall Drive, South Chesapeake
1212 Dragon Lane, South Chesapeake
$347,000
4 Beds ⋅ 2 Baths ⋅ 10649820 MLS
Under Contract - Listing for Input Only!

1212 Dragon Lane, South Chesapeake
1215 Brookside Landing, South Chesapeake
$425,000
4 Beds ⋅ 2.1 Baths ⋅ 10649222 MLS
Located in a wonderful and desired community, this home boasts great curb appeal that you see immediately with exterior vinyl siding and triple-pane windows for lower heating and cooling costs. The curb appeal continues with a new glass front door, new roof (2022), replaced shutters and gutters with downspout to match the color scheme. New Composite Fence in rear (2026). Enter and immediately get drawn into the black stained stairway with wrought iron spindles capped off with a black railing/bannister. Waterproof luxury vinyl flooring throughout completes the updated look. The kitchen features white cabinets, granite countertops and stainless steel appliances that conveys to include a commercial-sized refrigerator.

1215 Brookside Landing, South Chesapeake
216 Shore Side Road, South Chesapeake
$369,900
3 Beds ⋅ 1.1 Baths ⋅ 10647829 MLS
Kayak, paddleboard or fish right from your own backyard!! This 1447 sqft all brick ranch boasts 3 bedrooms and 1 1/2 baths, beautiful hardwood floors, updated kitchen with stainless appliances & granite countertops, Primary Bedroom with half bath, updated bath with clawfoot tub, Den with electric fireplace, Rinnai on demand gas water heater, and sunroom. Backyard has 3 sheds, greenhouse, a kayak rack, & a chicken coop! Enjoy the views of water & nature from your deck.

216 Shore Side Road, South Chesapeake
513 Corlew Court, South Chesapeake
$570,000
4 Beds ⋅ 3.1 Baths ⋅ 10647537 MLS
This beautifully maintained ranch-style home offers an inviting blend of comfort, style, and functionality. The spacious open layout is filled with abundant natural light and enhanced by plantation blinds, decorative doors, recessed lighting, and a tasteful combination of LVP flooring and carpet throughout. The open kitchen provides ample cabinetry, generous storage, a large pantry, and elegant granite countertops. The luxurious primary suite features a beautiful tray ceiling, dual vanities, a separate stand-up shower, and a large jetted tub for added relaxation. Situated on a desirable corner lot, the expansive yard is great for summer and fall entertaining. An extended driveway, ample parking for up to 6 vehicles, and a wide street add everyday convenience. There is an unfinished detached hobby space that is ready for whatever your imagination desires. The large utility shed allows ample space for storing outside lawn equipment. A custom grill awning and a huge gazebo, complete with TV, is like your own personal oasis right at home. Warm, welcoming, and thoughtfully designed, this home is truly a must-see.

513 Corlew Court, South Chesapeake
173 Harbor Watch Drive, South Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10645496 MLS
Don't miss out on this waterfront Penthouse condo in the heart of Great Bridge. Relax on one of two huge decks overlooking your own private boat slip offering the epitome of coastal living. Once inside, you will find a light-filled open space great for indoor-outdoor living and entertaining. The updates, including the HVAC, low-maintenance LVP flooring, and fresh paint mean you can pack your backs (and life jackets) and move right in! The ample storage indoor and out (don't miss the walk-in attic inside the primary closet) adds practicality and function. The resort-style condo amenities are not to be missed- not only is trash, water, and sewer covered, but you also have a community pool, clubhouse, and ground maintenance to leave all of your free time to enjoy your new coastal lifestyle. The sellers are open to selling the new boat and floating dock for an additional cost.

173 Harbor Watch Drive, South Chesapeake
1025 Ramsgate Lane, South Chesapeake
$549,000
4 Beds ⋅ 2.1 Baths ⋅ 10642714 MLS
Impeccably maintained brick ranch with 4 bedrooms, 2.5 baths, an attached one-car garage, wood-burning fireplace and a spacious backyard. The remodeled kitchen features quartz countertops, soft-close cabinetry, stainless steel appliances, under-cabinet lighting, and a movable island. Updated bathrooms, custom wood trim, and closet organization systems add thoughtful touches throughout. Enjoy the 15x40 deck, fenced yard, storage shed, and newly expanded driveway with RV pad, 50-amp hookup, and generator connection. Major improvements over the years include windows, HVAC, 200-amp electrical panel, flooring, garage door, water heater, sprinkler/well system, and more. Convenient to bases, shopping & highways for easy access in Hampton Roads and to NC. Hickory HS district. This home has been diligently cared for inside and out and is truly move-in ready!

1025 Ramsgate Lane, South Chesapeake
2317 Wildwood Road, South Chesapeake
$251,500
2 Beds ⋅ 1 Baths ⋅ 10643751 MLS
Move-in ready and beautifully updated, this home offers the perfect blend of modern style and everyday functionality. Step inside to a bright, inviting interior featuring a beautifully renovated kitchen with soft-close shaker cabinetry, granite countertops, and brand-new stainless steel appliances—perfect for cooking, gathering, and entertaining. Outside, the spacious backyard provides plenty of room for pets, gardening, play, or weekend cookouts. An oversized detached garage/workshop offers exceptional space for storage, hobbies, or DIY projects. Major updates have already been done for you, including a new roof, HVAC, upgraded panel and windows. Situated in an established neighborhood, this home is conveniently located just minutes from shopping, dining, major highways, the shipyard, and military bases, making daily commuting a breeze. Combining comfort, convenience, and thoughtful updates, this is a home you won't want to miss!

2317 Wildwood Road, South Chesapeake
1420 Carrolton Way Unit 91, South Chesapeake
$478,000
3 Beds ⋅ 2 Baths ⋅ 10643765 MLS
Highly desired CHARLESTON plan that included 3rd bedroom rather than a primary sitting room and welcoming morning room just off the kitchen. 2-car garage, open floor plan with spacious front porch & loads of natural light. Granite counter tops in kitchen included.

1420 Carrolton Way Unit 91, South Chesapeake
145A Beaver Dam Road, South Chesapeake
$575,000
10640859 MLS
Gorgeous cleared country acreage in the Hickory High School district, just appx 2.4mi from the high school, 4mi from Edinburgh, 7 mi from the VA/NC line and 7.8mi from City Hall. Some ditching in place for drainage. No access without permission from the Listing Agent, as property is currently being used as farm land.

145A Beaver Dam Road, South Chesapeake
20A Head Of River Road, South Chesapeake
$575,000
10640862 MLS
Gorgeous 20+ acre site in the Hickory High School district. Just app 2.4mi from the high school, 4mi from Edinburgh, 7mi from the VA/NC line and 7.8mi from City Hall. Land is cleared with some ditching in place. No access without permission from Listing Agent.

20A Head Of River Road, South Chesapeake
2A Head Of River Road, South Chesapeake
$575,000
10640860 MLS
Gorgeous Unique acreage just under 2acres in Hickory High School district, just app 2.4 mi from the high school, 4mi from Edinburgh, 7mi from VA/NC line, and 7.8mi from City Hall. Land is cleared with some ditching in place. Approx 340' of frontage with two nearly one acre square potential build sites, allowing for a barn, detached garage or acre of crops to be utilized privately, with a path that connects behind existing home in the center.

2A Head Of River Road, South Chesapeake
1213 Head Of River Road, South Chesapeake
$575,000
10640857 MLS
Gorgeous 3 Acre site in the Hickory High School District. Just 2.4mi from the high school, and approx 4mi from Edinburgh, approx 7mi from the Virginia/NC line, and 7.8mi from City Hall. Land is cleared, currently used for crops, with some ditching in place for drainage. No access without permission from Listing Agent.

1213 Head Of River Road, South Chesapeake
918 Seabreeze Court, South Chesapeake
$254,900
2 Beds ⋅ 1.1 Baths ⋅ 10641047 MLS
NEW HVAC SYSTEM BEING INSTALLED! Charming 2-bedroom townhome in the highly desirable Greenbrier area! The main level features a spacious living room that flows seamlessly into the kitchen, creating an easy, comfortable layout. The kitchen offers ample cabinetry and counter space, a new refrigerator, and room for a breakfast table. Sliding glass doors lead to a fully fenced backyard with a patio, for relaxing or entertaining. Upstairs, you’ll find two large bedrooms, each with generous closet space and access to a full bathroom. Enjoy peaceful neighborhood walking paths around the lake, all while being conveniently located near shopping, dining, and everyday essentials.

918 Seabreeze Court, South Chesapeake
Court, South Chesapeake
$102,000
10653427 MLS
Entered for Comp/Data Purposes Only.

Court, South Chesapeake
625 Marston Drive, South Chesapeake
$525,000
4 Beds ⋅ 2 Baths ⋅ 10650072 MLS
Welcome to 625 Marston Drive, the kind of home that checks the boxes buyers are searching for—and adds a backyard you’ll fall in love with! Located in Chesapeake’s highly desirable Hickory school district, this beautifully maintained 4-bedroom, 2-bath home offers an inviting, spacious layout with soaring ceilings, a cozy gas fireplace with built-ins, and a gorgeous kitchen featuring granite countertops, stainless steel appliances, generous storage, and a bright dining area. The spacious primary suite is the perfect place to unwind, while the finished room over the garage offers incredible flexibility as a bedroom, home office, playroom, or guest space. Outside is where this home truly shines—enjoy your own private retreat on approximately 0.30 acres with a pool, deck, covered patio, and plenty of space to entertain, relax, and enjoy summer days at home. Add in the 2-car garage and NO HOA, and this is a home that’s easy to get excited about. Great location, beautiful living spaces, an incredible backyard, and room to make it your own—come see 625 Marston Drive before someone else calls it home!

625 Marston 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!