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900 Golden Cypress Court, South Chesapeake
$425,000
5 Beds ⋅ 2 Baths ⋅ 10653879 MLS
Tucked at the end of a quiet cul-de-sac in the heart of Greenbrier, one of Chesapeake’s most desirable areas, with easy interstate access to everything! Situated on a large 11,327 sq ft lot, this home features a fenced backyard, large shed, firepit, front & rear decks, mature cypress tree & Japanese maple. Inside offers an open-concept layout, luxury vinyl tile, built-in entertainment cabinet & spacious primary bedroom (15’3”x19’) with large walk-in closet. Kitchen features double oven, new 36” SS gas cooktop, glass electric cooktop, new SS refrigerator & dishwasher. Updates include new roof, siding, carpet, blinds & 3/4-glass front door. Additional features include 2 hotel-style shower valves, 2 commercial thermostats, hot water recirculating pump & laundry room with deep sink. Heated & cooled 2-car garage includes workbench & extensive cabinetry, plus 4 off-street parking spaces and a beautifully landscaped yard.

900 Golden Cypress Court, South 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

1547 Orchard Grove Drive, South Chesapeake
$290,000
2 Beds ⋅ 2 Baths ⋅ 10654011 MLS
Welcome home to easy living in Orchard Grove! This spacious 2-bedroom, 2-bath condo offers a flexible layout designed for both everyday comfort and entertaining. Start your morning at the dedicated coffee bar before settling into the light-filled living room, where soaring ceilings and skylights create an open, airy feel. When the weather cools down, the gas fireplace makes the perfect spot to unwind. The updated kitchen features new cabinets, quartz countertops, stainless steel appliances, and plenty of space for preparing meals and gathering. Upstairs, the loft adds even more flexibility—create a home office, workout space, reading nook, hobby room, or explore modifications for an additional sleeping area. With two bedrooms and two full baths, there’s room to spread out while still enjoying the convenience of condo living. Orchard Grove puts shopping, dining, interstate access, military installations, and everyday conveniences nearby, making it easy to spend less time getting where you need to go and more time enjoying home.

1547 Orchard Grove Drive, South Chesapeake

100 Alice Street, South Chesapeake
$369,000
4 Beds ⋅ 2.1 Baths ⋅ 10653943 MLS
Welcome Home to Deep Creek! This beautifully renovated brick ranch offers 4 bedrooms, 2.5 baths, and an impressive list of brand-new updates. Step inside to discover brand-new gray carpet and luxury vinyl flooring throughout, complemented by fresh finishes that give the home a clean, modern feel. The updated kitchen features brand-new white cabinetry, a center island, granite countertops, and stainless steel appliances, creating a functional space for everyday living and entertaining. Both full bathrooms have been refreshed with brand-new ceramic marble tile in the showers for a polished, spa-inspired touch. And the updates continue beyond the interior! This home features a brand-new roof, HVAC system, and water heater, offering peace of mind for years to come. With two front and two back entry points, the layout also provides added flexibility for how you enter and use the home. Located in the desirable Deep Creek subdivision and just moments from the Gilmerton Bridge, this home offers convenient access to surrounding areas while providing the space and comfort of a brick ranch-style home. Four bedrooms. Two and a half baths. Brand-new major systems and finishes. Move-in ready. Come see all this home has to offer!

100 Alice Street, South Chesapeake

224 Northview Drive, South Chesapeake
$485,000
3 Beds ⋅ 2.1 Baths ⋅ 10653649 MLS
Welcome to 224 Northview Drive in Chesapeake, VA where pride of ownership is evident from the moment you arrive. Thoughtful updates, beautifully maintained spaces, and inviting indoor and outdoor areas make this home truly stand out. Inside, enjoy hardwood floors throughout the main living areas and bedrooms, along with a renovated kitchen featuring LVP flooring, Corian countertops, and stainless steel appliances. Both the main bathroom and en suite bathroom have been fully renovated with natural stone flooring, custom tile details, updated vanities, and premium finishes. Bedroom closets feature IKEA BOAXEL organization systems, and updated ceiling fans throughout add to the refreshed feel of the home. Outside, the upgrades continue with a custom two-level composite deck with low-voltage lighting, a large pea gravel patio and walkways, Wellis London spa, gazebo with swing, powered 10' x 14' shed with loft and workbench, privacy fencing, and a separate gated dog or play area. Mature trees, Japanese maples, azaleas, rhododendrons, and other established landscaping create a peaceful, wooded setting with plenty of character. The front exterior features a custom brick mailbox, brick hardscaping, fresh mulch, accent landscaping, and a double-width driveway with parking for up to five vehicles. Located in the Great Bridge school district and just minutes from shopping, restaurants, and everyday conveniences, this home offers a great blend of privacy and accessibility. If you’ve been searching for a well maintained home in Chesapeake, VA with upgrades throughout, hardwood floors, renovated kitchen and bathrooms, natural stone bathroom flooring, a large composite deck, hot tub, powered shed, privacy fenced backyard, mature landscaping, and generous parking, 224 Northview Drive is one to see.

224 Northview Drive, South Chesapeake

1115 Killington Arch, South Chesapeake
$335,000
3 Beds ⋅ 2.1 Baths ⋅ 10653708 MLS
End-unit townhouse in Greenbrier with a peaceful pond view right in your backyard-no neighbors behind you! This home has 3 bedrooms, 2.5 baths, plus a versatile loft that works as an office, 4th bedroom, or hangout space. The kitchen features butcher block countertops & stainless steel appliances. The primary bedroom is generously sized with plenty of room to spread out. Being an end unit means extra privacy, more natural light, and fewer shared walls than a typical interior unit. Outside, it's quiet and low-key with lakes and a playground to enjoy. Located in the heart of Greenbrier East with quick access to major highways, you are just minutes away from everything Hampton Roads has to offer, including military bases, shopping, dining, beaches, and parks.

1115 Killington Arch, South Chesapeake

1232 New Born Court, South Chesapeake
$450,000
5 Beds ⋅ 2.1 Baths ⋅ 10653581 MLS
Welcome home! This beautiful home in Chesapeake is ready for its new owners! With 5 bedrooms, 2.5 bathrooms, and a layout designed to offer the perfect balance of togetherness and privacy, there is room for everyone. The kitchen offers plenty of cabinets and counter space and flows right into the open dining/living area. Two separate living spaces provide flexibility for entertaining, relaxing, or everyday living. Outside, enjoy a spacious backyard with a great deck, storage shed, and even a chicken coop! Located in a highly sought-after school district and a close proximity to shopping, dining and interstate access, this house checks all the boxes! Shed and chicken coop convey as-is. Don't let this one get away - call today to schedule your tour!

1232 New Born Court, South Chesapeake

1128 Sir Galahad Drive, South Chesapeake
$357,000
3 Beds ⋅ 2.1 Baths ⋅ 10653187 MLS
PCS timing just right! Welcome to 1128 Sir Galahad Dr, an updated 3-bedroom, 3-bath Chesapeake home offering the flexibility, location, and lifestyle so many Hampton Roads buyers are looking for. Conveniently positioned near major commuter routes with easy access to Norfolk, Portsmouth, Virginia Beach, shopping, dining, and multiple military installations, this home makes getting around the region easy. Planning a PCS but not arriving until later this fall? This property offers a unique head start. Previously operated as a short-term rental and currently occupied by a long-term tenant through the end of November, the existing tenancy provides income in place during the transition and may help offset ownership costs before you’re ready to move in. It can also be a great fit for buyers looking for an approximately 60-day closing timeline. Inside, you’ll find an updated, move-in-ready interior with modern flooring, a refreshed kitchen featuring stainless steel appliances, generous cabinet and counter space, a fireplace, and comfortable living and dining areas. Large glass doors bring in natural light and lead directly to the backyard, creating an easy flow for everyday living and entertaining. The standout feature is your own in-ground pool! Whether you’re hosting friends, relaxing after work, or enjoying warm Hampton Roads days at home, the backyard adds a lifestyle feature that’s hard to beat. Whether you’re relocating to the area, planning ahead for your next move, or looking for a property with rental history and future flexibility, 1128 Sir Galahad Dr offers an uncommon combination of convenience, updates, rental potential, and a private pool. Secure your Chesapeake home now and make your move when the timing is right!

1128 Sir Galahad Drive, South Chesapeake

1914 Keeter Run, South Chesapeake
$440,000
4 Beds ⋅ 2.1 Baths ⋅ 10653149 MLS
Welcome home to Greenbrier! This beautifully maintained, move in ready home is tucked away on a desirable cul-de-sac in the heart of Chesapeake. Featuring numerous recent updates, you can move in with confidence and enjoy! The kitchen was updated in 2023 with new cabinets, countertops, and appliances. All bathrooms were refreshed in 2024 with new vanities, sinks, tubs, toilets, flooring, and paint. Major updates include a roof (2017), fence (2021), HVAC furnace (2025), condenser(2026), and water heater (2026). The first floor offers a spacious foyer, open living and dining areas, plus flexible bonus space great for a home office or playroom. Upstairs features a large primary suite with private bath and walk-in closet, three additional bedrooms, and a spacious shared bath. Conveniently located near Greenbrier shopping, dining, interstates, and local attractions. Don't miss your opportunity to make this home yours!

1914 Keeter Run, 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

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

2615 Cedar Road, South Chesapeake
$408,000
4 Beds ⋅ 2 Baths ⋅ 10653157 MLS
Renovated over the past few years, this beautifully kept brick ranch home is ready to welcome its next owners! Inside, the kitchen offers a fresh, modern feel with crisp white shaker cabinets, gleaming granite countertops, and newer stainless-steel appliances that make every day cooking a pleasure. Enjoy the charm of the hardwood floors, and other cozy features throughout this home as you add your own touch of decor! Before entering your backyard, enter into your fully screened and covered sunroom from your back door, enjoying the sounds and peace of your backyard. The adjoining fully enclosed sunroom provides a bright, inviting space for relaxing or entertaining, while the large backyard offers plenty of room for gatherings, play, or quiet evenings outdoors. Recent updates - including a newer installed roof and windows (2022), new front fencing (2025) newly remodeled bathroom showers (2024), and newly encapsulated crawl space by JES (2025), and for added peace of mind and long-term value with transferrable warranties! This charming home is truly move-in ready. Schedule your showing today!

2615 Cedar Road, South Chesapeake

1013 Saint Andrews Way Unit C, South Chesapeake
$220,000
2 Beds ⋅ 2 Baths ⋅ 10652873 MLS
This 2-bedroom, 2-bath condominium is located in Chesapeake’s desirable Greenbrier area. The home features new interior paint, new windows, new doors, and new carpet throughout, creating a clean and comfortable setting for everyday living, entertaining, or working from home.Enjoy living near the golf course while remaining close to Greenbrier Mall, Summit Pointe, Chesapeake Regional Medical Center, Norfolk International Airport, and the Port of Virginia terminals. The location also offers convenient access to Norfolk Naval Shipyard, Naval Station Norfolk, Naval Air Station Oceana, Joint Expeditionary Base Little Creek–Fort Story, Naval Support Activity Hampton Roads, U.S. Coast Guard Base Portsmouth, and Naval Medical Center Portsmouth.With shopping, dining, entertainment, and major highways nearby, many of Hampton Roads’ popular destinations are within easy reach. Schedule your showing today!

1013 Saint Andrews Way Unit C, 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

620 Estates Way Unit 120, South Chesapeake
$375,000
3 Beds ⋅ 2.1 Baths ⋅ 10652230 MLS
Surrounded by trees, this 2006 townhome-style condo offers a quieter setting with shopping, dining, parks & interstate access close by. The open main level features flexible living spaces anchored by a gas fireplace. The adjoining kitchen offers granite counters, stainless appliances, & an efficient layout open to the living areas. Upstairs are comfortably sized bedrooms, including a spacious primary suite w/ ensuite bath, double sinks, tiled shower & generous storage. Enjoy a shaded rear deck overlooking the wooded setting plus an oversized attached garage. Major updates include a high-efficiency York heat pump/HVAC installed 12/2025 (includes 10 yr parts/3 yr labor warranty) & architectural-shingle roof estimated at 2–5 years old. Pre-list inspection completed 9/2026; report available.

620 Estates Way Unit 120, South Chesapeake

152 Mann Drive, South Chesapeake
$460,000
3 Beds ⋅ 2 Baths ⋅ 10652558 MLS
Welcome to 152 Mann Drive in the heart of Great Bridge! This well-built brick ranch offers the perfect blend of charm and modern updates. Nearly every major improvement was completed in 2023, including luxury vinyl plank flooring, a fully updated kitchen, renovated bathrooms, HVAC system, and roof—giving you peace of mind for years to come. You’ll appreciate the seamless flow of the floor plan, designed for both everyday living and easy entertaining. Just off the kitchen, a cozy wood-burning fireplace creates a warm and inviting ambiance—perfect for relaxing evenings at home. With solid construction, stylish updates, and plenty of potential to make it your own, this is one you won’t want to miss!

152 Mann Drive, South Chesapeake

418 Supplejack Court, South Chesapeake
$485,000
4 Beds ⋅ 2.1 Baths ⋅ 10652092 MLS
Gorgeous renovated 4-bedroom, 2.5-bath home in sought after Riverwalk perfectly situated on a cul-de-sac. Open floor plan filled with natural light and stylish upgrades throughout. Stunning kitchen with custom cabinets, butcher block countertops, stainless-steel appliances and amazing center island. The formal dining room and cozy living room with fireplace offer ideal spaces for entertaining or relaxing. The primary ensuite has vaulted ceiling, double sink vanity, stunning shower and walk in closet. Enjoy relaxing on the oversized back deck for a peaceful backyard retreat. Additional highlights include a generous walk-in attic, oversized 2-car garage, and excellent storage throughout. Residents enjoy access to amenities including a clubhouse, swimming pool, playground, tennis courts, scenic trails, and a boat ramp and dock on the Elizabeth River. Close to beaches, military bases, amazing restaurants, shopping and more. Fantastic home and vibrant community!

418 Supplejack Court, 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.