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$689,000
5 Beds ⋅ 2.1 Baths ⋅ 10644518 MLS
Beautifully maintained 5-bedroom, 3,383-square-foot home offering peaceful golf course views in sought-after Wedgewood Estates. The thoughtfully designed floor plan features spacious living areas, an updated kitchen with a large center island, abundant cabinetry, and an open flow into the family room, creating a welcoming space for everyday living and entertaining. Large rear windows fill the home with natural light while overlooking the golf course and a beautiful wooded backdrop. Step outside to enjoy the screened porch and expansive patio, creating a private outdoor retreat. Thoughtfully maintained and exceptionally cared for, this home combines timeless character, quality updates, and outstanding curb appeal. Conveniently located in the heart of Greenbrier, just minutes from shopping, dining, parks, major highways, military installations, and healthcare, while offering the privacy and charm of one of Chesapeake's most desirable established neighborhoods.

1118 Fairway Drive, South Chesapeake
$210,000
2 Beds ⋅ 2.1 Baths ⋅ 10644311 MLS
Welcome to easy living in the desirable Riverwalk community! This adorable 2-bedroom, 2.5-bath condo offers a bright, open floor plan with spacious bedrooms, each featuring its own private bath. Enjoy low-maintenance living with fantastic community amenities, including a pool, ground maintenance, playgrounds, and more. Conveniently located near Greenbrier shopping, dining, hospitals, and major interstates. Association covers the roof.

802 Primrose Lane, South Chesapeake
$235,000
2 Beds ⋅ 2 Baths ⋅ 10644371 MLS
Move-in ready condo living at its best, situated in much sought-after the Riverwalk/Queens Gate community. Living level upstairs has open layout for easy living and entertainment + desirable natural light. Primary bedroom w/ensuite, second bedroom w/full bathroom across the hall. Renovated with new LVP flooring throughout condo, carpet on stairway, recently painted interior, remodeled kitchen includes new cabinets, quartz countertop, stainless steel appliances, and recessed lighting. New vanity lights and faucets in both bathrooms. Convenient location near dining, shopping, and entertainment! Must see before its gone!

709 Rapidan River Court Unit D, South Chesapeake
$190,000
2 Beds ⋅ 2.1 Baths ⋅ 10644380 MLS
Unlock incredible potential with this two-bedroom, two-bathroom condo, offering a fantastic blank canvas for investors, flippers, or homeowners looking to customize their own space. The main living area features a bright, open-concept layout with wood floors, a cozy fireplace, and sliding glass doors that open to a private patio. The adjacent kitchen features white cabinetry and a convenient breakfast bar that overlooks the dining and living spaces, creating a great flow for daily living and entertaining. Upstairs, the home offers two bedrooms, including a spacious primary suite complete with a walk-in closet and an en-suite vanity area. While the property requires cosmetic updates and repairs throughout—including new flooring, fresh paint, and bathroom updates—it presents the perfect opportunity to build immediate equity. Bring your vision and design ideas to transform this property into a modern personal retreat or a highly profitable addition to your portfolio! Residents will enjoy low-maintenance living with HOA dues that cover community pool and clubhouse access, ground maintenance, and trash pickup.

747 Ridge Circle, South Chesapeake
$375,000
3 Beds ⋅ 2 Baths ⋅ 10644346 MLS
You will love coming home to this comfortable ranch home with cozy rooms. Located near the intersection of Greenbrier Parkway and Volvo Parkway in Turtle Rock on a cul-de-sac. Enjoy the floor plan which includes living room, dining room, den with fireplace, eat-in kitchen, laundry room, primary bedroom with bathroom, two other bedrooms and hall bathroom. Walking trails & playgrounds nearby. Lots of shopping and dining closeby in Greenbrier area. This home has been well cared for and is ready for you. Welcome home!

1109 Hearthstone Landing, South Chesapeake
$410,000
3 Beds ⋅ 2 Baths ⋅ 10643754 MLS
Nestled in Oak Grove Meadows, this beautifully maintained, single-owner gem offers 3 bedrooms, 2 full bathrooms, and an unbeatable central location just minutes from the Chesapeake Expressway and endless dining and shopping. You are also uniquely positioned just a stone's throw from 51 acres of peaceful nature trails at the Chesapeake Arboretum. Step inside to find a completely turn-key home where all the big-ticket items are already done, boasting brand-new windows and carpet, durable 2-year-old Pergo laminate flooring, a 2022 HVAC, a 2019 tankless water heater, and a 2016 roof. The 2024 kitchen remodel features new cabinets and countertops. You will love the gorgeous, built-in sunroom that was part of the original home's construction and not a later addition. Outside, the property continues to impress with a fully fenced backyard perfect for relaxing and an oversized driveway with an abundance of parking for family and friends. This beautifully updated home is truly a rare find!

209 Rose Ash Way, South Chesapeake
$275,000
2 Beds ⋅ 1.1 Baths ⋅ 10643623 MLS

824 Nottaway Drive, South Chesapeake
$350,000
3 Beds ⋅ 3 Baths ⋅ 10643626 MLS
Experience waterfront living at its finest in this well maintained and beautifully updated condo on the Elizabeth River. Featuring LVP flooring throughout, this residence offers a seamless blend of style and durability. The updated kitchen shines with quartz countertops and stainless steel appliances, flowing effortlessly into the living space anchored by a cozy gas fireplace. The oversized primary suite is a true retreat, complete with a stunning en-suite bath showcasing floor-to-ceiling tile, dual sinks, and a new vanity with updated countertops. Two additional baths have been fully renovated with modern finishes. Go outside to your covered rear deck and take in serene water views, perfect for relaxing or entertaining. Community amenities include a pool, boat slip access, clubhouse, and more, offering a lifestyle of comfort and convenience.

143 Harbor Watch Drive, South Chesapeake
$255,000
2 Beds ⋅ 2.1 Baths ⋅ 10643204 MLS
Located in the Riverwalk section of Chesapeake, this corner unit offers added privacy and a great position tucked toward the backside of the building. Enjoy a quiet serene lifestyle. The functional floor plan provides comfortable everyday living. 2 Bedrooms on the 2nd floor along with 2 Full-Baths with a convenient powder room on the 1st floor. Generous closet space and plenty of storage throughout. A private, new fully fenced patio provides a great space to relax or unwind. Additional highlights include an HVAC system replacement (2025), stove and microwave (2025) and two reserved parking spaces right out front. Just minutes from major interstates, shopping, dining, hospitals and everyday conveniences. Vacant and move-in ready,

1002 Willow Green Court, South Chesapeake
$389,000
3 Beds ⋅ 2.1 Baths ⋅ 10643380 MLS
Move right into this immaculate 3-BR, 2.5-bath condo offering 1,835 sqft of beautifully updated living space! Thoughtfully remodeled and upgraded with quartz kitchen countertops, stainless steel appliances, updated bathrooms, newer paint throughout, new HVAC units and new water heater. When first entering the unit, you will notice the attention to detail starts at the front door and doesn't stop with newly added crown molding that adds a refined touch to the main living areas. The primary suite is located on the first floor and includes a fully remodeled bathroom. Enjoy beautiful lake views from any rear window in the unit or while relaxing on your private back patio. The perfect spot for morning coffee or unwinding at sunset. Residents also enjoy access to a community pool and clubhouse, adding to the low-maintenance lifestyle. Fees also include water, sewer and trash pickup, as well as, the exterior insurance. Conveniently located near shopping, restaurants, major highways, and military bases.

1425 Otterbourne Circle, South Chesapeake
$599,999
3 Beds ⋅ 2.1 Baths ⋅ 10643390 MLS
Move right into this beautifully upgraded, detached single-family home that perfectly pairs charm with an inviting, modern design. Built in 2014, this roughly 2,389 sq ft masterpiece is fully optimized for comfortable daily living and effortless entertaining. Main Level Highlights: Step through the welcoming entry foyer into a bright, open-concept floor plan radiating with natural light, custom blinds, and beautiful wood and laminate flooring. The expansive living space features a cozy electric fireplace. The updated kitchen boasts stainless steel appliances, a modern tile backsplash, crisp cabinetry, a large pantry, and a sunlit breakfast and dining area. Upper Level Retreats: Find ultimate comfort upstairs with a versatile second-floor loft that could be a home office, play area or convert into 4th Bedroom. The spacious primary bedroom suite serves as your personal oasis, offering a private retreat complete with an en suite bath and a large walk-in closet. Outdoor Living & Efficiency: Relax on the rear deck overlooking a sprawling, fully fenced backyard that directly overlooks a peaceful local farm. Large Modern Play-set conveying to buyer is negotiable. High-value capital updates include a new HVAC system in 2025, a tankless water heater, smart house features, and energy-efficient window tinting. Features an attached 2-car garage used for parking, storage, or a home gym. Centrally located near shopping, interstates, and area military bases. Bonus: Seller's preferred lender is offering closing cost assistance if utilized by buyer ask LA for more information!

712 Appalachian Court, South Chesapeake
$429,900
4 Beds ⋅ 2 Baths ⋅ 10643538 MLS
Welcome home to this charming brick ranch near Summit Pointe in Chesapeake, Virginia.Brick ranch near Summit Pointe! The heart of the home is the inviting country kitchen, equipped with stainless steel appliances and plenty of space for gathering with family and friends. The standout feature is the oversized primary suite, providing a private retreat with room for a sitting area, home office, or workout space! The huge backyard features a 2-year-old above-ground saltwater pool surrounded by a wraparound deck with recess lighting, creating the ideal setting for cookouts, entertaining, and relaxing weekends at home. Spacious floor plan featuring a welcoming living room and cozy den, both complete with fireplaces, perfect for relaxing on cool winter evenings. Upgrades for peace of mind include newer paint, newer windows, newer stainless steel appliances, newer vapor barrier, newer drain line, newer roof, newer ceiling fans and 200 amp electric panel. Call today to view!

224 Essex Drive, South Chesapeake
$369,000
3 Beds ⋅ 2.1 Baths ⋅ 10643081 MLS
Welcome to your beautifully maintained turn-key dream home in the heart of Chesapeake. This wonderful condo features a high-efficiency HVAC system less than one year old, brand new carpets, freshly painted, 9' ceilings, crown molding, beautiful hardwood floors, custom blinds, upgraded lighting, alongside a convenient second-floor laundry room. The kitchen is a chef's delight, featuring granite countertops, tiled backsplash, custom cabinets with under-cabinet lighting and stainless steel appliances. Retreat to the primary suite, vaulted ceilings, an oversized walk-in closet, and a spa-like en suite bath complete with dual vanity sinks. Outside, the 1.5-car garage offers ample storage or workshop space, while the concrete patio is perfect for relaxing in your low-maintenance yard. Conveniently located near shopping, malls, restaurants, parks and easy interstate access. Don't miss out on this perfect Greenbrier location.

432 Autumn Green Lane, South Chesapeake
$630,000
5 Beds ⋅ 3 Baths ⋅ 10643153 MLS
Home is being sold AS-IS.Come home to the beautiful 5bdrm, 3 bth with 3000 sqft of living space to enjoy. Freshly painted. Centrally located in the heart Great Bridge near shopping, dining, and the interstate.

1202 Copper Knoll Lane, South Chesapeake
$410,000
3 Beds ⋅ 2.1 Baths ⋅ 10643082 MLS
Welcome to this spacious 3-bedroom, 2.5-bath home offering over 1,900 square feet of comfortable living in the heart of Chesapeake's desirable Greenbrier area. The thoughtfully designed floor plan features generous living spaces, a welcoming great room with a fireplace, and an updated kitchen with beautiful quartz countertops that continue into the bathrooms for a cohesive, modern look. Step outside to enjoy the stamped concrete patio, added in 2021, providing the perfect space for relaxing or entertaining. Additional updates include a new HVAC system (2018), refrigerator (2024), and dryer (2026), offering peace of mind for years to come. Conveniently located within driving distance of shopping, dining, parks, Greenbrier's business district, major interstates, and military bases, this well-maintained home is ready for its next owner.

640 Sweet Leaf Place, South Chesapeake
$234,900
2 Beds ⋅ 1 Baths ⋅ 10643302 MLS

844 Wickford Drive, South Chesapeake
$524,900
3 Beds ⋅ 2.1 Baths ⋅ 10643243 MLS
Beautifully maintained 55+ condominium in the desirable Greenbrier area. Built by Stephen Alexander Homes, this elegant residence blends historically inspired architecture with timeless craftsmanship, featuring 10-foot ceilings, transom windows, custom crown moulding and trim work, and hardwood floors. Offering 3 bedrooms plus a spacious room over the garage, this home provides exceptional flexibility for guests, hobbies, or a home office. The gourmet kitchen with double ovens is designed for everyday living and entertaining. An interior private elevator provides effortless access to both levels. Additional features include an attached two car garage with overhead storage and utility sink, brand-new dual-zone HVAC, a Rinnai tankless water heater, and a freshly painted exterior. Relax on the spacious front porch or entertain on the private tiled patio with a SunSetter retractable awning. Whole-house audio and family room surround sound add comfort and ambiance throughout. Move in ready!

1016 Briars Landing Landing, South Chesapeake
$239,900
3 Beds ⋅ 1.1 Baths ⋅ 10643144 MLS

824 Huntly Drive, South Chesapeake
$999,985
6 Beds ⋅ 4 Baths ⋅ 10642034 MLS
White all-brick 2-story contemporary home with front porch, arches and large foyer. The backyard is a private oasis with trees, pond and flowing fountain. Enjoy the serenity of nature, including the blue herons, egrets, ducks and more, as you sip your morning coffee or have dinner on the patio. As you enter the first-floor foyer, notice the large formal dining room on the left and an archway to the familyroom with gas fireplace. Enter the huge open kitchen with granite counters, an oversized island, eat-in area and pantry. Also, on the first level are 2 bedrooms (one can be used as an office), a full bath with shower, and an archway inset that holds the Stiltz-Lift elevator. Either take the wooden stairs with wrought-iron railings or the elevator to the 2nd level. Upstairs are the Primary bedroom with extra-large walk-in closet and an incredible ensuite bath, complete with 2 sinks, large, deep soaking tub, 5 x 4 ft shower with rainfall head and sit-down area. A separate laundry room, three other bedrooms and 2 full bathrooms provide the space for family and friends to come and visit. BUT, there's more to complete the 2nd floor. Check-out the theater/game room (great for entertainment) and additional wrought-iron railings that overlook the stairs, foyer area and lead to the elevator. The extra-large 3-car garage has enough room for your cars or anything else. AND then there's the backyard; well, you'll just have to see it for yourself. This home is convenient to shops, restaurants, malls, stores, country club, banks, parks, interstate, university and so much more!

1324 Simon Drive, South Chesapeake
$509,000
4 Beds ⋅ 2.1 Baths ⋅ 10642834 MLS
This home is a Wellspring gem with valuable upgrades. The front lawn and spacious 2 car garage create a warm and inviting first impression. Inside, the thoughtfully designed first floor offers multiple living spaces including a formal living room, dining room, eat in kitchen and cozy den featuring a gas fireplace. A convenient half bath makes everyday living and entertaining a breeze. Upstairs has four generously sized bedrooms including a primary suite with vaulted ceilings. Throughout the home, you'll appreciate having no carpet and LVP in every bedroom. The deck right outside the patio door is superb for hosting, overlooking an expansive newly fenced backyard with endless possibilities for play, gardening, pets or outdoor gatherings. A storage shed provides additional space for tools and equipment. TESLA EV charger conveys.

405 S Monterey Drive, South Chesapeake
$309,000
3 Beds ⋅ 2.1 Baths ⋅ 10642451 MLS
Welcome home to this charming and spacious interior townhome, perfectly located in the heart of everything! Offering nearly 1,600 sq ft of well-maintained living space, this home has 3 spacious sized bedrooms & 2.5 baths, providing the perfect blend of comfort and functionality. Filled with character and warmth, the thoughtfully designed floor plan offers plenty of room to relax and entertain. Step outside to enjoy the private backyard an ideal space for morning coffee or weekend entertaining! Conveniently located just minutes from the interstate, shopping, restaurants, and everyday amenities, you'll love the ease of living this central location provides. With ample parking and a welcoming neighborhood feel, this home truly has it all.

1404 River Birch Run, South Chesapeake
$315,000
3 Beds ⋅ 1.1 Baths ⋅ 10642736 MLS
no showings until 07/08.

1360 Mill Lake Quarter, South Chesapeake
$499,000
4 Beds ⋅ 2.1 Baths ⋅ 10642093 MLS
This beautiful home features a spacious floor plan designed for comfortable everyday living and effortless entertaining. The main level showcases an updated kitchen, beautiful hardwood floors in the main living areas, a tiled hallway, powder room, kitchen, and an oversized laundry room for added convenience. Upstairs, you'll find four generously sized bedrooms. The finished room over the garage offers exceptional flexibility and can easily serve as a fourth bedroom, game room, media room, home office, or playroom to suit your needs. Step outside to a large, fully fenced backyard featuring an expansive deck that's perfect for cookouts, outdoor dining, and entertaining. With plenty of room for kids and pets to play, this backyard is the ideal setting for relaxing, gathering with friends, and creating lasting memories.Centrally located, this home is just minutes from Greenbrier Mall, major interstates, Chesapeake Regional Medical Center, shopping, dining, and everyday conveniences. Combining space, versatility, and an unbeatable location, this move-in ready home is ready to welcome its next owners. Schedule your private tour today!

1028 Austin Drive, South Chesapeake
$370,000
4 Beds ⋅ 2.1 Baths ⋅ 10642424 MLS
Welcome to this exceptional end-unit luxury townhome, original owner bought as the community's model home. Built in 2014 and thoughtfully upgraded throughout, Thomason Trail offers nearly 1,900 square feet of living space, combining timeless finishes with everyday comfort. You'll appreciate the warmth of rich hardwood flooring, abundant natural light, and the attention to detail that sets this home apart. The kitchen is designed to impress, featuring granite countertops, ample cabinetry, a pantry and an open layout that flows seamlessly into the main living and dining areas. All of the mechanicals have been recently updated to include hot water heater 2026. Ceiling fans in every room plus custom wood blinds provide both style, privacy and comfort. One of the home's most distinctive features is the versatile loft, complete with custom built in shelves. Minutes from Greenbrier for shopping and restaurants you won't want to miss this opportunity.

1601 Thomason Trail, South Chesapeake
$624,900
6 Beds ⋅ 4.1 Baths ⋅ 10642445 MLS
Rare opportunity to own a beautifully updated 6-bedroom, 4.5-bath home featuring a private, fully equipped in-law suite for multigenerational living, extended family, guests, rental income, or a private home office. The main residence offers 5 spacious bedrooms, 3 full baths, and a stunning remodeled kitchen with quartz countertops, sleek high-gloss cabinetry, stainless steel appliances, and space for a large center island. The separate in-law suite lives like its own home, complete with an open loft-style bedroom, 1.5 baths, walk-in closet, full-size laundry, upgraded kitchen with quartz counters and stainless appliances, and generous living space. Recent upgrades include renovated baths, new windows, patio doors, and Nest thermostats. Step outside to your backyard oasis featuring an 8-foot in-ground pool with newer liner, filter, and pump, plus a built-in deck bar ideal for entertaining. Conveniently located near shopping, dining, schools, military bases, beaches, and major commuter routes.

501 Thornloe Ln Lane, South Chesapeake
$288,500
3 Beds ⋅ 1 Baths ⋅ 10642393 MLS
Cute 1 story cottage in the heart of Greenbrier Chesapeake on almost an acre of private wooded property. This charming 2 bedroom home with a bonus room that has been used as a 3rd bedroom (no closet). Bright and Airy vintage appeal. Galley Kitchen opens to dining room with arched opening to living room. Open concept with character. The property is zoned Industrial and the current legal use is residential (nonconforming-grandfathered) Buyers should independently verify requirements with the City of Chesapeake, for any plans for additions or redevelopment or converting to an Airbnb STR.

106 Greenbrier Road, South Chesapeake
$385,000
3 Beds ⋅ 2.1 Baths ⋅ 10642308 MLS
Well cared for 3 bedroom 2.5 bathroom hoe in sought after neighborhood of Knells Ridge/Oak Lake Estates Freshly painted, new deck, new LVP flooring in hall bathroom, LG smart washer 2024, ADT touchscreen smart alarm system 2024, google nest protect smart smoke & carbon monoxide detector 2024, LG smart dishwasher 2023, LG smart dryer 2021, LG smart refrigerator 2021, hot water heater 2021, ring pro door bell 2018, ecobee smart thermostat 2017, 2013 new roof, new patio door 2013 Condo/HOA fees include mowing of front yard and trimming of bushes, trash pick up and pool

208 Oak Grove Run, South Chesapeake
$719,000
5 Beds ⋅ 3.1 Baths ⋅ 10642010 MLS
Look no further! Come check out this beautiful home located at the end of a cul-de-sac featuring 5 bedrooms, 3 and a half bathrooms, as well as an office. The amazing kitchen includes a farm sink, custom cabinets, and granite countertops throughout. Did I mention the large island which includes a wine refrigerator too. Other features in this home: remote controlled blinds in downstairs windows; Google home front doorbell, backyard floodlight camera and Google Nest thermostat both upstairs and downstairs; epoxy garage floor; backyard shed with electric including lights, outlets and panel. Tesla wall connector charger. Tankless Water Heater. Kids playset!! All of this with NO monthly HOA!!

1303 Fulton Lane, South Chesapeake
$449,000
4 Beds ⋅ 2.1 Baths ⋅ 10641959 MLS
Discover timeless charm in this beautiful, traditional home located in the heart of Chesapeake. Featuring 4 bedrooms, 2.5 bathrooms, and a spacious two-story layout, this home includes a bedroom with its own en suite bath, making it great for guests or added privacy. Gather around the cozy fireplace on cool evenings, or enjoy casual meals in the bright breakfast area. Step outside to a fully fenced backyard, great for entertaining, pets, or relaxing outdoors. Recent upgrades, including new siding and roof (2021) and a remodeled primary bathroom (2025), enhance both the home's beauty and value. An attached garage and attic complete this exceptional property. Don't miss your opportunity to make this Chesapeake gem your own!

744 Helmsdale Way, South Chesapeake
$309,000
3 Beds ⋅ 2 Baths ⋅ 10641791 MLS
Renovated condo in private waterfront community in the heart of Great Bridge! This beautiful 3BR/2BA condo boasts an open floor plan great for entertaining. New LVP floors, carpet, tiled bathrooms, quartz countertops throughout, appliances, fixtures, paint & more ALL just in 2023. New HVAC 2025 .Enjoy a lifestyle with such amenities as ,communal fire pit and grilling area, outdoor pool, clubhouse, gazebo, kayak storage, docks, elevator, building exterior, water, sewer, trash pickup, grounds, master insurance policy, storage & 2 dedicated parking. Sale includes a deeded boat slip #5 in protected private harbor on the Intercostal Waterway that you can view from your unit and balcony! Call today for your private showing.

4 Harbor Watch Drive Unit 508, 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.