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1561 Rollesby Way, South Chesapeake
$335,000
3 Beds ⋅ 2.1 Baths ⋅ 10651317 MLS
Welcome to 1561 Rollesby Way! This well-appointed 3-bedroom, 2.5-bathroom home offers a spacious and functional layout in the desirable Greenbrier area of Chesapeake. The first-floor primary suite features a large walk-in closet & private bathroom for added convenience. The kitchen offers stainless steel appliances, ample cabinetry, & a convenient bar overlooking the dining area. The living room provides a comfortable gathering space with a sliding glass door leading to the fenced-in backyard & patio, great for relaxing or entertaining. A first-floor half bath is conveniently located for guests. Upstairs, you’ll find two additional bedrooms, both featuring walk-in closets, along with a full bathroom & a versatile bonus room that would make an ideal home office, reading room, or flex space. Condo dues include access to the community pool, ground maintenance, trash pickup, & water service. Conveniently located in Greenbrier with easy access to shopping, dining, & entertainment.

1561 Rollesby Way, South Chesapeake
28 Hinton Avenue, South Chesapeake
$330,000
4 Beds ⋅ 2 Baths ⋅ 10654130 MLS
Experience total move-in readiness in this beautifully updated Chesapeake home! Featuring fresh paint and new flooring throughout, the bright interior flows into a modern kitchen equipped with shaker cabinets and stainless steel appliances. Bathrooms boast stylish tile updates, while peace of mind comes standard with a new roof, HVAC, some new windows and new water heater. There is also a bonus florida room and lovely front porch. Perfectly blending comfort and modern upgrades, this property is an absolute must-see today!

28 Hinton Avenue, South Chesapeake
514 Trellis Trail, South Chesapeake
$329,400
2 Beds ⋅ 2.1 Baths ⋅ 10646125 MLS
Spacious 1,870-square-foot, 2-bedroom townhome in a four-unit building. Peacefully set among trees, the home offers a feeling of privacy. BRAND NEW air conditioning unit will keep you cool on hot summer days. The versatile first-floor office can easily serve as a third bedroom, guest room, or flex space. Beautiful wood floors throughout the lower level offer aesthetic appeal and simplify cleaning and maintenance. An oversized kitchen features a generous pantry, breakfast area, and plenty of cabinet space. Sliding glass doors open to a private, fenced in patio, wonderful for relaxing or entertaining. Upstairs, you'll find two generously sized primary suites, each with its own private full bathroom, providing comfort and privacy for residents and guests alike. A spacious second floor laundry room includes washer and dryer hookups and a utility sink for added convenience. Community amenities include a sparkling swimming pool, grounds maintenance, trash pickup, and sewer, all included with the HOA. Ideally located in the sought-after Greenbrier area, with easy access to interstates, shopping, and dining. Quick move in available, come see this beauty today!

514 Trellis Trail, South Chesapeake
1773 Land Of Promise Road, South Chesapeake
$327,540
10655658 MLS
Lot is 37.28 cleared acres and located offroad. Easy access is by a recorded right of way. There is a crushed-asphalt path back to this lot and runs down the center of the 37.28 acres. The lot is rectangular. Soybeans are currently growing. Do not drive on plants. There are two available lots. The lot immediately in front of this one can be sold with or sold alone. First parcel consists of 25 acres. Buyers must do their own due diligence, but it is the understanding of the sellers that one home may be built on each of the two lots. Recorded plat is available.

1773 Land Of Promise Road, South Chesapeake
1540 Eldwick Drive #103, South Chesapeake
$325,130
2 Beds ⋅ 2 Baths ⋅ 10650599 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Addison model features an open-concept floorplan & high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with center island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms & 2 baths. Owner’s suite includes a private bath & walk-in closet with custom wood shelving. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #103, South Chesapeake
758 Creekside Crescent, South Chesapeake
$325,000
3 Beds ⋅ 2.1 Baths ⋅ 10656884 MLS
SPACE, LOCATION, & UPGRADES! Welcome to this spacious 3 BR, 2.5 BA, 1,562 sq. ft. END-UNIT townhome in the sought-after Riverwalk community along the Elizabeth River! Featuring one of the largest original floor plans, this home boasts a generously sized, privacy-fenced backyard, spacious deck and oversized secondary storage shed. Inside, enjoy ceramic tile flooring in the hallway, kitchen and baths, stainless-steel appliances, and Delta faucets and Kohler toilets installed in 2026. Major improvements include a new $14,000 3-ton HVAC system, 6-inch gutters (2025), replacement windows and doors (2011), and roof (2015). Embrace the vibrant Riverwalk lifestyle with a clubhouse, pool, tennis, pickleball, dock access, playgrounds, walking trails, weekly food trucks, swim team, garden club and community events. Convenient to shopping, dining and major interstates, this home offers an exceptional combination of space, upgrades and community living!

758 Creekside Crescent, South Chesapeake
1025 Shore Road, South Chesapeake
$325,000
3 Beds ⋅ 1.1 Baths ⋅ 10654363 MLS
Come tour this ranch home with beautiful hardwood floors and a functional living space. This property has a partially open floor plan with a versatile layout. The open room space can be used to entertain, as an office, or as spare living space. The backyard is large and wooded, offering a storage shed and plenty of space for gardening and entertaining. The dishwasher, water heater, and refrigerator are all new (2025) and convey with the property.

1025 Shore Road, South Chesapeake
5341 Libertyville Rd, South Chesapeake
$325,000
3 Beds ⋅ 2 Baths ⋅ 10652746 MLS
Welcome home to an unparalleled narrative of comfort in this prime Chesapeake real estate sanctuary. Fully dialed-in for its next owner, this 3-bedroom, 2-bathroom single-story home showcases an inviting open concept layout. The primary suite serves as a quiet retreat with a custom-tiled shower, while the gourmet kitchen shines with granite surfaces and custom cabinetry. Complete with a generous backyard and storage shed, commuters will love the quick highway access! Ask about the potential VA loan assumption at a 5.1% interest rate! Available to a qualified buyer, subject to lender/servicer approval and applicable VA requirements.

5341 Libertyville Rd, South Chesapeake
650 Lacy Oak Drive, South Chesapeake
$325,000
2 Beds ⋅ 2.1 Baths ⋅ 10651928 MLS
Welcome to this spacious two-bedroom, two-and-a-half-bath condo in the desirable Greenbrier/Kempsville area. The versatile bonus room on the main level is ideal for a home office, playroom, or guest space. The kitchen features stainless steel appliances and opens to the dining area, with a walk-in pantry and convenient half bath nearby. Laminate flooring flows throughout the first floor, while the second floor offers comfortable carpeting. Upstairs, both bedrooms include private full baths and walk-in closets. A large walk-in laundry room with a utility sink adds extra convenience. Condo dues include trash pickup, pool access, and grounds maintenance. Move-in ready and waiting for its new owners!

650 Lacy Oak Drive, South Chesapeake
11.8 Acres Ballahack Road, South Chesapeake
$325,000
10650830 MLS
Great opportunity on 11.811 acres of cleared land in southern Chesapeake. This is a flag lot and comes with 25' of road frontage going south to the remaining 11.3 acres of cleared crop land. The bulk of this lot is located approx. 800 feet off the paved city road and will allow for a relaxed setting for that custom homesite you have been wanting. Sit on the back porch and watch the sun set while enjoying the expansive view across almost 600 acres of open crop land. Hickory school district and just minutes from the 168 bypass. Convenient to all of Hampton Roads and Chesapeake Genera Hospital. Zoned A1 presently. Sale subject to existing farm lease.

11.8 Acres Ballahack Road, South Chesapeake
320 Esplanade Place, South Chesapeake
$325,000
2 Beds ⋅ 2.1 Baths ⋅ 10650351 MLS
Welcome home to this cozy 2-bedroom, 2.5-bath townhome in the desirable Riverwalk community, offering 1,352 square feet of comfortable, light-filled living space. The open-concept kitchen and living area creates an inviting space for everyday living and entertaining. The kitchen features granite countertops and stainless steel appliances, while the main living area offers durable LVP flooring and a gas fireplace for added warmth and character. Two sets of double French exterior doors fill the space with natural light and open directly onto the refinished back deck. Step outside to enjoy a refinished private deck surrounded by flower beds, creating a relaxing outdoor retreat. Upstairs, both bedrooms feature comfortable carpeting, while the home's bathrooms are fully tiled for a clean, polished finish. Enjoy everything the Riverwalk community has to offer, including a clubhouse, swimming pool, tennis courts, and multiple walking trails throughout the neighborhood.

320 Esplanade Place, South Chesapeake
5 Harbor Watch Dr Unit 413, South Chesapeake
$325,000
3 Beds ⋅ 2 Baths ⋅ 10648847 MLS
PARK YOUR BOAT HERE! Enjoy waterfront living in the heart of Great Bridge. This beautifully maintained 3BR/2BA condo offers an open floor plan and a private balcony with harbor views. The spacious primary suite includes a walk-in closet, double vanity, soaking tub, and separate shower. Sale includes a boat slip in the protected private harbor, two reserved parking spaces, and assigned storage. Community amenities include elevator access, pool, clubhouse, gazebo, grilling area, kayak storage, and docks. Exceptionally clean and move-in ready with plenty of opportunity to make it your own!

5 Harbor Watch Dr Unit 413, South Chesapeake
1439 Rollesby Way, South Chesapeake
$325,000
3 Beds ⋅ 2.1 Baths ⋅ 10647568 MLS
Approved for VA, FHA, and conventional loan. Welcome home to this beautifully maintained 3-bedroom, 2.5-bath condo in the highly desirable Greenbrier area of Chesapeake. This well designed home features two primary suites, each with a private bath, offering exceptional flexibility for guests, roommates, or multigenerational living. The bright open floor plan provides comfortable living and entertaining space, while the 1st floor bedroom can be used as a home office or guest room. Conveniently located near shopping, dining, parks, and major interstates, this low-maintenance home combines comfort, convenience, and an unbeatable location.

1439 Rollesby Way, South Chesapeake
1115 Warrington Boulevard, South Chesapeake
$325,000
2 Beds ⋅ 2.1 Baths ⋅ 10645916 MLS
Loan is assumable at 5.625% interest rate. Enjoy low-maintenance living in this move-in ready townhome-style condo in the desirable Warrington Hall community! Conveniently located just minutes from shopping, restaurants, parks, and major interstates, you'll have easy access to everything Chesapeake and Hampton Roads have to offer. Community amenities include a clubhouse, pool, tennis courts, and ground maintenance for a carefree lifestyle. Inside, the spacious layout features a kitchen with abundant cabinetry, all appliances, pantry, and a breakfast bar which opens up to the dining room. The inviting family room provides lots of natural lighting, and there is a convenient powder room for guests. Upstairs, both spacious bedrooms offer walk-in closets and private ensuite bathrooms. The primary suite features a dual vanity and tub/shower combination. Step outside to enjoy your own private patio, perfect for morning coffee or relaxing at the end of the day. Just move in and start enjoying all this community has to offer!

1115 Warrington Boulevard, South Chesapeake
772 Shell Road, South Chesapeake
$325,000
3 Beds ⋅ 1.1 Baths ⋅ 10644798 MLS
Own A Piece Of "Country Living" In "The City!" Original Farmhouse Type Home Situated On Approx. 2 Acres - Very Unusual Lot! Really Private Setting! Home Needs Renovating...Has Lots Of Potential! Located Off Shell Rd. (Firman St) With Flag Driveway To Back Of Properties. HVAC System 2 Years Old, Roof Approx 16 Years Old, 3 Bedrooms, 1 Bathroom Upstairs, Half Bath Downstairs. Good Sized Kitchen With Real Knotty Pine Cedar Cabinets! Laundry Room Off Kitchen. French Doors Into Living Room And Columns Into Dining Room. Original Hardwood Floors Downstairs. Just A Charming House...Needs Renovation! Huge "Pie Shape" Additional Lot...All On One Deed. Interested In Building Another Dwelling? Look Up The New Senate Bill 531 Which Requires All Localities To Allow Assessory Dwelling Units (ADVs) "By Right" In Single Family Residential Zones...It Might Apply! Buyer Would Do Their Own Due Diligence On This Property.

772 Shell Road, South Chesapeake
2008 Girard Avenue, South Chesapeake
$325,000
3 Beds ⋅ 1 Baths ⋅ 10644687 MLS
Own the end of the street! Tucked away in Deep Creek, this rare 7 parcel package spans both sides of Girard Avenue and offers a surprising sense of privacy within an established Chesapeake neighborhood. This residential listing represents 2 of the 7 parcels and includes the existing home, which conveys strictly as is. The remaining 5 parcels are offered through the coordinated land listing referenced as 2004 Girard Avenue, with all 7 sold together as one package. Altogether, the property offers approximately 2.59 acres of R10 zoned land and room to imagine something bigger. Create a starter homestead, explore a shared living concept with room for more than one generation to call home together, take on your next rehab or investment project, hold the property for the future or bring an entirely new vision to life. Any proposed use is subject to zoning and required approvals. The end of Girard Avenue is ready for its next chapter!

2008 Girard Avenue, South Chesapeake
1540 Eldwick Drive #302, South Chesapeake
$320,130
2 Beds ⋅ 2 Baths ⋅ 10650581 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, see agent for details. Our Rowen model is a corner location that features an open-concept floorplan, high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms and 2 baths. Owner’s suite includes a private bath and walk-in closet with custom wood shelving. Enjoy a patio or balcony space off living room. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #302, South Chesapeake
948 Shoal Creek Trail Unit A, South Chesapeake
$320,000
2 Beds ⋅ 2 Baths ⋅ 10654731 MLS
Beautiful end-unit condo features an open first-floor layout with tall ceilings and abundant natural light, creating a bright and airy feel. The kitchen is equipped with modern appliances and a well-designed layout for both everyday living and entertaining. The spacious primary suite offers both comfort and style, with an updated attached bath. Additional bedroom provides versatile space for guests, a home office, or hobbies, and are served by a second full bath. All appliances including washer and and dryer convey. Centrally located in the heart of Greenbrier, with easy access to shopping, dining, and major highways.

948 Shoal Creek Trail Unit A, South Chesapeake
709 Montrose Court, South Chesapeake
$320,000
3 Beds ⋅ 2.1 Baths ⋅ 10643459 MLS
Welcome to 709 Montrose Ct., Chesapeake, VA! This well- maintained two-story townhome offers 1,610 +/- sq. ft. of comfortable living space in a convenient location. Built in 1991, the home features 3 bedrooms, 2.5 baths, and a functional floor plan designed for everyday living. The spacious layout provides ample room for relaxing, entertaining, and working from home. Conveniently located near shopping, dining, schools, medical facilities, and major highways, this property offers easy access to everything Chesapeake has to offer. Whether you're a first-time homebuyer, downsizing, or seeking an investment opportunity, this townhome presents n excellent opportunity. Quarterly HOA fees help mINTin the community, providing added convenience nd peace of mind. Don't miss your chance to make this Chesapeake property your next home!

709 Montrose Court, South Chesapeake
1505 Waitsel Drive Unit 304, South Chesapeake
$319,900
2 Beds ⋅ 2 Baths ⋅ 10651771 MLS
Welcome home to easy, low-maintenance living in this beautifully appointed 3rd-floor condo! Featuring an open-concept floor plan, soaring ceilings, and large windows that fill the space with natural light, this home offers comfortable one-level living with stylish interior finishes throughout. The spacious kitchen is designed for both everyday living and entertaining, with quartz countertops, stainless steel appliances, and a convenient breakfast bar. The owner's suite provides a relaxing retreat with an attached bath and walk-in closet featuring custom wood shelving. Outside, enjoy a peaceful pond with a short trail loop, plus a dedicated dog park in this pet-friendly community. Condo amenities include ground maintenance, sewer, trash pickup, and water for added convenience. Located just minutes from shopping and dining at Sam's Circle and offering an easy Battlefield commute, this home truly has everything you need for comfortable Chesapeake living!

1505 Waitsel Drive Unit 304, South Chesapeake
1213 Killington Square, South Chesapeake
$319,000
2 Beds ⋅ 2.1 Baths ⋅ 10650185 MLS
MOVE-IN READY end-unit townhome in highly desirable Greenbrier! Fresh paint and brand-new carpet throughout give this home a clean, modern feel. The bright eat-in kitchen features stainless steel appliances and granite countertops, perfect for everyday living and entertaining. The spacious great room includes a dining area, cozy fireplace, and direct access to a large fenced backyard with storage shed and utility room (shed conveys As-Is). A convenient half bath and laundry complete the first floor.Upstairs offers two spacious en-suite bedrooms filled with natural light. The third-floor loft provides flexible space ideal for a home office, media room, playroom, or guest suite.Enjoy low-maintenance living in a prime location close to shopping, dining, parks, and major highways making commuting a breeze. Don’t miss this stylish, move-in ready home!

1213 Killington Square, South Chesapeake
4108 Wake Avenue, South Chesapeake
$317,000
3 Beds ⋅ 1.1 Baths ⋅ 10630259 MLS
Beautifully and fully remodeled ranch-style home offered by the original owners. Located in a quiet, well-established neighborhood and conveniently close to shopping, dining, and amenities. This three-bedroom, two-and-a-half-bath home features a spacious layout with numerous updates throughout and all new appliances.Enjoy a large backyard ideal for outdoor living and gatherings, along with a sizable storage shed. The garage includes built-in shelving for organization and can be converted into a family room, den, or office space if desired. Accessibility features include a well-maintained wheelchair ramp and a walk-in shower.Move-in ready and thoughtfully updated. Come see all this home has to offer.

4108 Wake Avenue, South Chesapeake
504 Plummer Drive, South Chesapeake
$315,000
3 Beds ⋅ 1 Baths ⋅ 10650561 MLS
Investor Special! Brick ranch in Chesapeake featuring 3 bedrooms, 1 bathroom, a detached garage/workshop, and a spacious yard. This fixer-upper is being sold as-is and offers plenty of potential for renovation and customization. Bring your vision and transform this property into a great investment or personal home!

504 Plummer Drive, South Chesapeake
304 Centerville Turnpike N, South Chesapeake
$315,000
2 Beds ⋅ 1 Baths ⋅ 10648165 MLS
Rare 1.54-acre homesite in a highly desirable Chesapeake location! The property includes an existing home and out buildings that convey as-is. Suitable for renovation. R-15S zoning and an outstanding location near Greenbrier, major highways, shopping, dining, and schools, this property offers endless possibilities for investment.

304 Centerville Turnpike N, South Chesapeake
316 Esplanade Place, South Chesapeake
$315,000
2 Beds ⋅ 2.1 Baths ⋅ 10643193 MLS
INVESTMENT LOAN OR CASH - TENANTS IN THE PROPERTY UNTIL 31 JAN 2027. TWO PRIMARY SUITES EACH WITH A FULL BATH, EAT-IN KITCHEN WITH REFRIGERATOR, ELECTRIC RANGE, DISHWASHER, BUILT-IN MICROWAVE, AND PANTRY. LARGE FAMILY ROOM WITH GAS FIREPLACE, PEDESTAL SINK IN HALF BATH, TRAY CEILINGS, WASHER/DRYER HOOKUP, WOOD FLOORS, CEILING FANS, NEWER CARPET AND PAINT, FRENCH DOORS, PULL DOWN ATTIC STEPS, ATTACHED GARAGE WITH ELECTRIC OPENER, 2-CAR DRIVEWAY, CORNER LOT WITH DECK AND PRIVACY FENCE, HOA AMMENITIES INCLUDE CLUB HOUSE, POOL, TENNIS COURTS, PLAYGROUNDS AND WALKING TRAILS.

316 Esplanade Place, South Chesapeake
1417 Gust Lane, South Chesapeake
$314,000
5 Beds ⋅ 3.1 Baths ⋅ 10644206 MLS
This unique property offers a main home and a separate second residence, creating flexibility that's hard to find. Whether you're looking for multigenerational living, a private in-law suite, rental income, guest accommodations, or space to run a home-based business (where permitted), this property adapts to your lifestyle. The main home features 3 bedrooms and 2.5 baths, while the second home offers 2 bedrooms and 1 bath. Two detached garages provide excellent space for workshops, hobbies, storage, vehicles, or equipment, and two sheds add even more functionality. Enjoy a deck for one home, a patio for the other, separate electric meters, ample parking, and room to spread out. Priced to sell

1417 Gust Lane, South Chesapeake
5 Harbor Watch Drive Unit 405, South Chesapeake
$310,000
3 Beds ⋅ 2 Baths ⋅ 10651901 MLS
Wake up to peaceful water views right from your bedroom! This spacious, well-maintained 3-bedroom, 2-bath condo offers 1,762 square feet per MLS of comfortable, single-level living and low-maintenance convenience. Featuring luxury vinyl plank flooring in the living areas. Large windows and a sliding glass door bring in plenty of natural light. The kitchen offers abundant cabinet space, newer stainless steel appliances, including a wine fridge, and a convenient pantry. The spacious primary suite features a walk-in closet, linen closet, and private bath with a double vanity, soaking tub, and separate stand-up shower. Additional features include newer windows and a sliding glass door, ceramic tile, carpeting, and plenty of storage throughout. Amenities include a pool and clubhouse. Association services also include dock maintenance, water, sewer, and trash. Deeded Boat Slip negotiable with sale

5 Harbor Watch Drive Unit 405, South Chesapeake
719 Creekside Crescent, South Chesapeake
$305,000
3 Beds ⋅ 2.1 Baths ⋅ 10653124 MLS
Welcome home to this well-maintained End unit 3-bedroom, 2.5-bath townhome located in the Riverwalk community. The inviting open floor plan provides a comfortable flow between the living, dining, and kitchen areas, making it ideal for everyday living and entertaining. Step outside to enjoy the private rear patio, complete with a storage shed for added convenience. Upstairs, you’ll find three generously sized bedrooms, including a spacious primary suite with an en-suite bath and ample closet space.

719 Creekside Crescent, South Chesapeake
1540 Eldwick Drive #202, South Chesapeake
$300,130
2 Beds ⋅ 2 Baths ⋅ 10655131 MLS
Now Pre-Selling The Flats at Grayson Commons. Limited time incentives: $10K anyway allowance plus up to $7,000 toward closing cost assistance when using preferred lender for financing, listed price reflects $10K incentive taken off price of home, see agent for details. Our Rowen model is a corner location that features an open-concept floorplan, high ceilings, large windows for plenty of natural light, & beautiful interior finishes. Spacious kitchen with island, quartz countertop, and stainless steel appliances. One level living w/ 2 bedrooms and 2 baths. Owner’s suite includes a private bath and walk-in closet with custom wood shelving. Enjoy a patio or balcony space off living room. Photos and video are for illustrative purposes only and are of models in a previous community, Finishes, upgrades and included features vary.

1540 Eldwick Drive #202, South Chesapeake
1528 Hambledon Loop, South Chesapeake
$300,000
3 Beds ⋅ 2.1 Baths ⋅ 10656711 MLS
Welcome to 1528 Hambledon Loop, a desirable end-unit in Brighton Park at Greenbrier! This 3-bedroom, 2.5-bath home, 2 master bedrooms with ensuites offers a comfortable floor plan with the added privacy and natural light of an end-unit location. Recent updates include a NEW water heater, offering added peace of mind for the next homeowner. Enjoy the convenience of low-maintenance community living with access to neighborhood amenities, including 2 community pools. Ideally located in Chesapeake’s Greenbrier area, close to shopping, dining, entertainment and major roadways. Whether you're a first-time buyer, looking for additional space, or seeking a convenient Chesapeake location, this home is ready for its next owner. Schedule your showing today!

1528 Hambledon Loop, 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.