Refine Search
Sort by
700 Nottoway River Court Unit D, South Chesapeake
$265,000
2 Beds ⋅ 2 Baths ⋅ 10653023 MLS
Welcome to this spacious and comfortable condo located in the desirable Riverwalk neighborhood. This home offers plenty of room to spread out and entertain. With both bedrooms connected to their own en suites you can enjoy both privacy and convenience. Upstairs includes a versatile loft area leading into the primary bedroom; providing additional space for a home office, reading area, or flex space. With new upgrades like the Heat Pump (2021) and the Roof (2025, by the association) you can have the peace of mind that you're in a good space. Outside, a cute private patio provides a pleasant spot to relax and enjoy some fresh air. The condo association gives low-maintenance living by covering the siding and roof, water and sewage, trash pickup, while maintaining the pool, clubhouse, and public spaces! With large living areas, a functional multi-level floor plan, and important updates, this condo is ready for its next owner! Setup a tour and make it you!

700 Nottoway River Court Unit D, South Chesapeake

1336 Blackwater Road, South Chesapeake
$550,000
5 Beds ⋅ 2 Baths ⋅ 10646017 MLS
Embrace the off-the-grid lifestyle on 0.96 acres in Chesapeake's desirable Blackwater area, zoned for highly sought Hickory schools! This property maximizes self-sufficiency with pure water from a premium 600+ ft Certified Artesian well, a double tank water softener, and a tankless electric water heater. To drive utility costs down further, consider adding a maintenance-free solar panel program at no cost for instant savings without equipment hassles. Inside, the layout features a versatile room off the living room (perfect for an office or homeschool/playroom) plus a FROG, creating up to 6 bedroom-like spaces. The oversized septic system easily supports an ADU, multi-generational living, or rental income. Picture sipping morning coffee while collecting farm-fresh eggs from your backyard chickens. Best of all, sellers are open to negotiating improvements with an acceptable offer to help customize this homestead exactly to your liking!

1336 Blackwater Road, South Chesapeake

905 Calhoun Way, South Chesapeake
$645,840
3 Beds ⋅ 3.1 Baths ⋅ 10629473 MLS
TO BE BUILT - Dreamy Augusta Cottage by coveted local builder w/unmatched architectural detail, from custom arches to soaring 10’ ceilings & stunning hardwood floors. Open-concept 1st floor blends Dining & Great Rm, w/French doors opening to private courtyard & patio, your outdoor oasis. Chef’s kitchen shines w/oversized island, Quartz counters & custom range hood. Generous 1st-floor BR w/en-suite bath offers flexible living. Versatile mudroom w/pantry, powder room & access to 2-car garage make everyday living effortless. Upstairs, sun-filled BR3 features walk-in closet, while BR4 (or loft) adapts to your needs. Also included are a shared dual bath & oversized laundry room. Private Primary retreat boasts spa bath w/ dual sinks, garden tub, large tiled shower & super-sized walk-in closet w/ dual storage areas. Professionally managed grounds offer low-maintenance living. Luxury, comfort & lifestyle in one exceptional home.

905 Calhoun Way, South Chesapeake

2206 Edwin Drive, South Chesapeake
$573,390
3 Beds ⋅ 3 Baths ⋅ 10627394 MLS
Welcome to The Charleston at Retreat at Edinburgh—a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more—all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections.

2206 Edwin Drive, South Chesapeake

1300 Oregon Crossing, South Chesapeake
$555,000
4 Beds ⋅ 2 Baths ⋅ 10654828 MLS
Remarkable brick ranch situated on a corner lot overlooking the community pond! Meticulously maintained and beautifully updated, this home offers exceptional style and comfort throughout. Recent improvements include gorgeous flooring, fresh paint, and updated fixtures that create a warm, inviting atmosphere. The spacious room over the garage serves as a fourth bedroom and offers additional space perfect for a home office, hobby room, or flex area. The well-appointed kitchen features gas appliances, while the cozy gas fireplace adds charm to the living space. Step outside to your private backyard retreat featuring a sparkling in-ground pool, captivating landscaping, and multiple deck areas designed for relaxing and entertaining. Every detail has been thoughtfully maintained, making this home truly move-in ready. A rare opportunity, don't sit on this one

1300 Oregon Crossing, South Chesapeake

515 Sweet Leaf Place, South Chesapeake
$425,000
3 Beds ⋅ 2.1 Baths ⋅ 10654218 MLS
Welcome to this beautifully maintained 3 bedroom, 2.5 bath home. Step inside to a bright, open floor plan featuring rich dark wood floors that flow throughout the main living areas. The stunning kitchen is designed to impress with custom cabinetry, upgraded appliances, and plenty of space for cooking and entertaining. The inviting great room is the heart of the home, complete with gas fireplace and custom built-in shelving, creating the perfect space to relax or gather with family and friends. Upstairs, you'll find spacious bedrooms, including a comfortable primary suite, offering room for everyone to spread out. Outside, enjoy your own private patio, ideal for morning coffee or simply unwinding after a long day. Residents enjoy fantastic community amenities, including a pool, clubhouse, and exterior grounds maintenance, allowing you to spend more time enjoying your home and less time on upkeep. BRAND NEW ROOF (July 2026). Don’t miss your opportunity to make this your next home!

515 Sweet Leaf Place, South Chesapeake

604 Colonel Byrd Street, South Chesapeake
$550,000
4 Beds ⋅ 3.1 Baths ⋅ 10653623 MLS
Gorgeous planned community with neighborhood clubhouse, swimming pool, fitness center and recreation spaces. At the center of the home, the chef-inspired kitchen features an oversized prep island, stone countertops, stainless steel appliances, premium soft-close cabinetry, and a walk-in pantry. The primary suite is conveniently situated on the main level, complete with a generous walk-in closet and en-suite bath. Upstairs, you will find two sizable secondary bedrooms, a full bath, and an open loft enhanced with custom built-ins. A private fourth bedroom or versatile bonus suite sits above the garage, featuring its own dedicated full bath and integrated shelving—ideal for guests, a home office, or a media room. Outdoor living is a standout feature, highlighted by a screened porch, an open patio, and a wood-burning firepit overlooking peaceful water views within a fully fenced backyard.

604 Colonel Byrd Street, South Chesapeake

1100 Dane Street, South Chesapeake
$430,000
3 Beds ⋅ 2 Baths ⋅ 10653150 MLS
If you’re looking for a home that feels like a luxurious vacation retreat all year long, this is the one. Beautifully renovated inside and out, this home blends timeless traditional elegance with comfort and resort-style living. Inside, you’ll find two spacious living rooms, each with its own fireplace, creating warm and inviting spaces for relaxing or entertaining. The over sized primary bedroom is a private retreat, complete with a beautifully renovated, spa-inspired bathroom designed to make everyday life feel luxurious. Step outside into your own private backyard oasis, featuring a beautiful in-ground pool, covered pergolas, landscaped surroundings, and inviting outdoor living spaces where you can relax, entertain, and feel like you’re on vacation without leaving home. The property also features a two-car carport and a huge detached two-story workshop/flex storage building, offering exceptional additional space for storage, hobbies, projects, or more. This is more than a home, it's a lifestyle designed to enjoy every day. Extensive improvements completed in 2024 - 2025. A detailed Features & Upgrades, Conveyance/Exclusion, and Seller Information package available upon request. This home is a must-see in person contact your agent to schedule a private showing.

1100 Dane Street, South Chesapeake

2801 Southport Ave., Central Chesapeake
$305,000
3 Beds ⋅ 1 Baths ⋅ 10653156 MLS
This beautifully updated property situated on a spacious corner lot of over a quarter acre in Chesapeake! Recent improvements completed in June 2026 include: a brand-new GAF architectural shingle roof, new gutters, Updated new LVP flooring, and fresh interior paint, giving this home a clean, modern feel and added peace of mind. The versatile FLEX room offers endless possibilities and can easily serve as a 4th bedroom, home office, playroom, or home workout space to fit your lifestyle. Step outside to your fully fenced backyard retreat, designed for both relaxation and entertaining. Enjoy summer days in the above-ground pool and unwind or host gatherings under the pergola on the patio while appreciating the privacy this backyard provides. Conveniently located near shopping, dining, schools, and major interstates, this move-in-ready home combines thoughtful updates, flexible living space, and exceptional outdoor setting you won't want to miss.

2801 Southport Ave., Central Chesapeake

1120 Kathleen Lane, South Chesapeake
$1,500,000
5 Beds ⋅ 3.1 Baths ⋅ 10650552 MLS
A builder's own estate — private, impeccable, and set on approximately eight wooded acres at the end of a quiet Chesapeake cul-de-sac. Custom-built by the builder for his own family, this brick-and-stone home reflects a level of care you rarely find. Nothing here has been left untouched; it lives like new construction. A long gravel drive winds past mature trees to the home, where a sweeping front porch offers multiple entries and room to linger. Deer, turkey, and other wildlife are frequent visitors. Inside, a grand open floor plan rises to cathedral ceilings, finished with updated tile flooring, crown molding, and Hunter ceiling fans. The living area anchors around a dramatic stone fireplace and flows into an eat-in kitchen with rustic cabinetry, updated KitchenAid appliances, an electric cooktop, and a large center island with bar seating. The first floor holds a spacious primary suite, generously sized baths, and a well-placed Jack-and-Jill. Upstairs, brand-new carpet runs through bedrooms of exceptional size, and the primary closet is fitted with extensive custom built-ins. The two-story garage apartment is a standout, two bedrooms, 1.5 baths, multiple living areas, and a full eat-in kitchen, great for guests, multigenerational living, or income potential. The garages themselves have been freshly painted white, bright and spotless. Recent improvements include fresh paint throughout, LED lighting, updated kitchen and bath fixtures, two new HVAC units, a mini-split serving the room over the garage, smoke detectors, smart locks, and an on-demand propane water heater. Estate infrastructure is equally serious: 600-amp electrical service, a four-inch private well with pump house, a new water-softening system, hard-ducted HVAC, an illuminated crawl space, and a septic system serviced in 2026. A concrete parking pad completes the property. Privacy, craftsmanship, and acreage — a genuinely distinctive Chesapeake estate.

1120 Kathleen Lane, South Chesapeake

1421 Chesapeake Avenue, Central Chesapeake
$345,000
3 Beds ⋅ 2.1 Baths ⋅ 10647836 MLS
Timeless character meets modern comfort in this beautifully updated 1915 South Norfolk home. A spacious wraparound porch sets a welcoming tone, while the light-filled, open-concept interior showcases an original staircase and updated finishes throughout. The custom kitchen features gray shaker cabinetry, soft-close doors and drawers, granite countertops, a large center island, stainless steel appliances, and distinctive lighting. The generous primary suite offers a private bath with dual sinks. Additional highlights include updated flooring, carpet, windows, doors, siding, and an HVAC system installed in 2021. Outside, enjoy a fenced backyard, side porch, and two-vehicle driveway. Move-in ready and filled with charm. Schedule your tour today!

1421 Chesapeake Avenue, Central Chesapeake

1145 Sunlight Drive, South Chesapeake
$465,000
4 Beds ⋅ 2 Baths ⋅ 10655999 MLS
Escape to your own private waterfront retreat on nearly 1/2 acre in the sought-after Inland Colony community, where peaceful wooded surroundings and serene water views create the perfect connection to nature. This 2,494 sq. ft. home offers 4 bedrooms, 2 baths, a first-floor primary suite, detached ADU, 1-car garage, and private dock with access to the Intracoastal Waterway on the Elizabeth River. Enjoy the expansive deck overlooking the backyard and water or unwind on the screened porch off the primary suite. Fresh paint and new carpet enhance the bedrooms, while the spacious kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and generous prep space. French doors open from the dining room to the living area, creating an ideal layout for entertaining. The FROG with new carpet and large walk-in attic provide excellent flexibility and storage. Some photos may be virtually staged. Conveniently located near shopping, dining, top-rated schools, and interstate access while offering a true waterfront escape.

1145 Sunlight Drive, South Chesapeake

313 Holyoke Lane, South Chesapeake
$283,999
2 Beds ⋅ 2.1 Baths ⋅ 10653079 MLS
Turnkey Luxury in Oakbrooke Crossing – Fully Updated & Pre-Inspected!Welcome to this beautifully updated 2-bedroom, 2.5-bathroom townhome-style condo in desirable Oakbrooke Crossing! This move-in-ready home features brand-new LVP flooring, fresh neutral paint, and an updated kitchen with laminate countertops, breakfast bar, and stainless steel appliances. Upstairs, you’ll find two spacious primary suites, each with its own private en-suite bathroom great for guests, roommates, or a home office. Enjoy added peace of mind with a brand-new water heater (2024), recently serviced HVAC, and a professional pre-inspection with the report available upon request.Conveniently located in the heart of Chesapeake, just minutes from Greenbrier shopping, dining, business centers, and interstate access. The low-maintenance condo lifestyle includes ground maintenance, trash service, and community upkeep. Ready for you! Schedule your showing today!

313 Holyoke Lane, South Chesapeake

1070 Mesa Loop, South Chesapeake
$501,763
4 Beds ⋅ 3.1 Baths ⋅ 10631709 MLS
Ready Now: Luxury End Unit townhome condo w/rear load 2 car garage. Luxury LVP floor in select living areas, 2nd floor: Kitchen GE Cafe Matt Black appliances including refrigerator, center island w/shiplap, living room linear fireplace w/shiplap, pantry, living area w/Office/flex room, 1st floorbr/flex room, hall bath & mudroom. 3rd floor Primary w/ceramic shower-2 shower heads, dual sinks, 2 closets, 2 br's - jack & jill bath, linen closet, laundry. Quartz tops kitchen & all baths, covered entry, fenced front yard w/gate to multi trail, 2nd floor Deck off dining area. 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. 2-10 home warranty, master insurance, trash pick up, private streets, city water/sewer, guest parking, multipurpose trails with lake and fountain. Only 56 homes. Central Greenbrier location.

1070 Mesa Loop, South Chesapeake

5108 Annapolis Drive, West Chesapeake
$550,000
4 Beds ⋅ 2 Baths ⋅ 10630795 MLS
A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch style living with 4 bedrooms including a large finished room over the garage. From the front porch to the Family Room also open to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your door step in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

5108 Annapolis Drive, West Chesapeake

415 Prince Phillip Court, South Chesapeake
$409,000
3 Beds ⋅ 2.1 Baths ⋅ 10654072 MLS
Welcome to this spacious 3-bedroom, 2.5-bath split-level condo in a great Chesapeake location near Oak Grove Park, the hospital, shopping, and interstate access. The mid-level foyer leads to the lower level, featuring a comfortable sitting room with a fireplace, access to the back deck and fenced backyard, a utility closet, two bedrooms with large closets, full hall bathroom, and access to the attached 2-car garage with a convenient garage door opener. Upstairs, the updated kitchen offers stainless steel appliances, a pantry, bar, and breakfast area with bench seating, along with a fireplace and built-in storage. The upper-level living room provides additional space for relaxing or entertaining. The spacious primary suite features a walk-in closet and ensuite bathroom with a granite vanity, built-in makeup table, jetted tub, separate shower, and water closet.

415 Prince Phillip Court, South Chesapeake

3527 Radford Circle, West Chesapeake
$230,000
2 Beds ⋅ 1.1 Baths ⋅ 10653212 MLS
Welcome to this spacious 2-bedroom townhome in sought-after Western Branch with no HOA! The main level features a comfortable living area with a wood-burning fireplace, convenient half bath, and sliding glass doors leading to the back deck. The kitchen offers an eat-in dining area and includes a stainless steel appliances, disposal, and dishwasher. The washer and dryer are conveniently located on the main floor in the utility closet. Upstairs, the primary bedroom features a dual-entry ensuite bathroom with a large vanity and water closet with shower. Enjoy one of the largest fenced backyards in the neighborhood, with plenty of space for outdoor activities and entertaining. Great location with easy access to shopping, dining, major roads, and highly sought-after Western Branch schools.

3527 Radford Circle, West 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!