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106 Greenbrier Road, 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
1717 Orchard Way, South Chesapeake
$288,000
3 Beds ⋅ 2 Baths ⋅ 10626941 MLS
Beautifully Renovated Condo - Looks like New! 3 Bedrooms with First Floor Primary Bedroom! Eat-In Kitchen with New Appliances, huge breakfast bar, large great room w/Cathedral Ceilings & Fireplace. Spacious Bedrooms and Screened in Porch! Windows on Order!

1717 Orchard Way, South Chesapeake
5 Harbor Watch Drive Unit 419, South Chesapeake
$287,500
3 Beds ⋅ 2 Baths ⋅ 10633000 MLS
Enjoy low-maintenance living at Harbor Watch in Great Bridge. This well-maintained third-floor condo with elevator access offers 3 bedrooms, 2 baths, and 1,764 sq ft of comfortable living space. The open-concept layout connects the kitchen, dining, and living areas, with sliding glass doors leading to a private balcony and filling the home with natural light. The spacious primary suite includes a walk-in closet and en-suite bath with double vanity, soaking tub, and separate shower. Community amenities feature a pool and clubhouse, while the HOA covers exterior maintenance, roof, insurance, water, sewer, trash, and grounds care. Conveniently located near shopping, dining, parks, and major commuter routes. **BONUS** Seller will pay 5 months of condo fees on an acceptable offer.

5 Harbor Watch Drive Unit 419, South Chesapeake
322 Holyoke Lane, South Chesapeake
$287,000
2 Beds ⋅ 2.1 Baths ⋅ 10651614 MLS
Come fall in love with this beautiful move-in ready corner unit in sought-after Greenbrier. You will be impressed by this spacious & bright open-concept layout connecting the living & dining areas, the updated kitchen with granite countertops & SS appliances. Kitchen & half bath grouted tile. New flooring downstairs in 2025. Home features 2 large bedrooms with 2 full en-suite baths & 2 large walk-in closets. Enjoy private enclosed patio with additional storage. Appl. working, but convey "as is". Condo fees include inground pool, trails with park benches, water, sewer, trash, grounds maintenance & master insurance policy. Minutes from shopping, dining & entertainment. Easy access to VAB oceanfront. Schedule a tour today!

322 Holyoke Lane, South Chesapeake
704 Inlet Quay Unit J, South Chesapeake
$287,000
3 Beds ⋅ 2 Baths ⋅ 10624805 MLS
Located in the heart of Riverwalk, this second-floor condo features cathedral ceilings in the great room and primary bedroom, a balcony, a deck, and dual-entry exterior stairs. Enjoy a wooded view with a charming bridge just behind the unit. Updates include newer LVP flooring and fresh paint (2023), an updated kitchen with quartz countertops, stainless steel appliances, subway tile backsplash, and custom white cabinetry, as well as an updated primary bath with new shower tile, fixtures, a glass enclosure, toilet, and garden tub trim. Major systems include a Rheem water heater (2017) and a Goodman 2 1/2-ton heat pump (2021). Riverwalk amenities include scenic trails, water views, tennis courts, swimming, and biking. This home shows beautifully—don’t miss it!

704 Inlet Quay Unit J, South Chesapeake
1535 Hambledon Loop, South Chesapeake
$286,000
2 Beds ⋅ 2.1 Baths ⋅ 10649710 MLS
Well maintained townhouse-style condo in the highly sought-after Brighton Park at Greenbrier community! Bright and open two-story home features an open-concept layout, fresh paint and all appliances convey to include washer and dryer. Kitchen features a brand new microwave and the home is freshly painted and cleaned. New roof installed in this year. Two primary suites each offer a private en-suite bath and large walk-in closets. Fully fenced private patio, and storage shed. Amenities include a community pool, water, sewer, trash, exterior & ground maintenance, siding, roof coverage for easy, low-maintenance. So just relax and enjoy your new home. Conveniently located near shopping, dining, and interstate access. Schedule your showing today.

1535 Hambledon Loop, South Chesapeake
917 Brice Court, South Chesapeake
$285,500
10588693 MLS
Build your dream home on this spacious vacant lot located in a quiet, family-friendly subdivision. Situated on a level parcel with utility connections available at the street (water, sewer, electricity), this lot offers the perfect blend of privacy and community. Enjoy well-maintained surroundings, paved roads, and close proximity to schools, shopping centers, parks, and major highways. Whether you're an investor, builder, or future homeowner, this is a rare opportunity to secure a premium piece of land in a desirable neighborhood - Need a builder - we can help - have your own - no problem.

917 Brice Court, South Chesapeake
939 Still Harbor Circle, South Chesapeake
$285,000
3 Beds ⋅ 1.1 Baths ⋅ 10645022 MLS
Be settled before summer ends! Townhome offers a modern/functional layout. First floor features a light & bright eat-in kitchen, SS appliances, ample counter space & vintage cabinets. Living room boasts an attractive wood burning fireplace, you'll finally have that mantle for holiday decorating! Three bedrooms up with a full bath, new carpet, fresh paint throughout. Enjoy direct access to the fully fenced back yard from the dining area. Back yard provides the perfect space for entertaining, relaxing or allowing pets to roam. Take advantage of the path that runs along the lake, just outside the rear gate.

939 Still Harbor Circle, South Chesapeake
1984 Woodgate Arch, South Chesapeake
$285,000
3 Beds ⋅ 1.1 Baths ⋅ 10630209 MLS
Welcome home to this beautifully updated 3-bedroom townhome in the heart of Greenbrier! Bursting with style and warmth, this move-in ready gem features fresh paint, luxury LVP flooring, and brand-new carpet throughout. The stunning kitchen is a true showstopper with crisp white cabinetry, quartz countertops, and sleek stainless steel appliances, perfect for everything from busy mornings to cozy nights in! Upstairs, has 3 beautifully updated bedrooms & bathroom that feel fresh, modern, and inviting. Major updates, including a NEW ROOF, newer water heater, and recently serviced HVAC, offer peace of mind so you can focus on enjoying your new home!! Ideally located in a sought-after neighborhood with top-rated schools nearby, and just minutes from shopping, dining, and interstates, this home blends convenience with charm. Whether you're entertaining, relaxing, or creating new memories, this one just feels right. Call today for your personal tour!

1984 Woodgate Arch, South Chesapeake
213 Cedar Creek Terrace, South Chesapeake
$285,000
2 Beds ⋅ 1.1 Baths ⋅ 10624196 MLS
SOLAR PANEL LOAN TO BE PAID AT SETTLEMENT!!!Townhouse in the heart of Great Bridge with many new updates to include, updated bathrooms, upstairs carpet, downstairs stamped concrete, hot water heater, asphalt roof, doors, ceiling fans, attic insulation, HVAC in 2021 and a new sewer line. Conveniently located to shopping, and sought after Great Bridge school district. Appliances work but convey as is. SOLAR PANEL LOAN TO BE PAID AT SETTLEMENT!!!

213 Cedar Creek Terrace, South Chesapeake
1447 Leckford Drive, South Chesapeake
$285,000
2 Beds ⋅ 2.1 Baths ⋅ 10624728 MLS
Tucked into the easy rhythm of the Greenbrier area with a Brand New Roof installed yesterday, this is a two-story condo that feels a little like a quiet song at the end of the day. Sitting beside a small pond where the water catches the light just right, this place offers a peaceful view while keeping you nearby everything Chesapeake has to offer. Step inside and the first floor opens up with a comfortable living room that flows naturally into the dining area, making it a great spot to gather, unwind or simply let the day slow down a bit. The kitchen is ready for anything from a quick cup of coffee to a late night snack, and the laundry room and convenient half bath keep everyday living easy. Upstairs you’ll find two well sized bedrooms, each with its own full bath – a layout that gives everyone their own space to relax and recharge. Simple, comfortable, and set in a location that makes life a little easier. 1447 Leckford is the kind of place that just feels right.

1447 Leckford Drive, South Chesapeake
1217 Cedar Mill Square, South Chesapeake
$285,000
3 Beds ⋅ 1.1 Baths ⋅ 10622882 MLS
Welcome HOME! This immaculate three bedroom townhouse features new carpet, fresh paint, and updated touches throughout! Eat-in kitchen with easy access to brick paver patio and privacy fenced backyard. Propane grill in place for grilling out.Laundry room/pantry with washer & dryer has shelves & cabinets for great storage! Primary bedroom has spacious walk-in closet. Room to park two vehicles at your front door.

1217 Cedar Mill Square, South Chesapeake
1457 Whittamore Road, South Chesapeake
$285,000
3 Beds ⋅ 1 Baths ⋅ 10622769 MLS
Home sweet home deep in the heart of Hickory! Situated on a close to one-acre lot and priced under $300K, this updated property offers space, value, and opportunity. Major components recently replaced include roof, HVAC system, windows, and hot water heater for added peace of mind. Interior upgrades feature fresh paint, updated flooring, renovated bathroom with tiled shower and modern fixtures, stainless steel appliances, updated cabinetry, butcher block countertops, subway tile backsplash, and marble-style tile flooring. Open living area with decorative stair railing and flexible layout. Finished upper-level loft provides additional space for bedroom, office, or bonus room. Large lot offers room to expand or create your ideal outdoor retreat. Tons of upgrades completed with opportunity to add your finishing touches.

1457 Whittamore Road, South Chesapeake
2400 Payne Road, South Chesapeake
$285,000
3 Beds ⋅ 1 Baths ⋅ 10613045 MLS
Spacious ranch on a large corner lot featuring 3 large bedrooms and a large living area that’s great for entertaining. The property also offers a large detached garage and a fenced-in backyard. Recent updates include a new roof and recently installed water heater, with HVAC installed in 2013.

2400 Payne Road, South Chesapeake
1023 Winged Foot Court Unit A, South Chesapeake
$285,000
2 Beds ⋅ 2 Baths ⋅ 10609827 MLS
Welcome home to this charming Fairways Villas condo perfectly positioned on the golf course! Enjoy single-story living with a bright, open floor plan featuring vaulted ceilings in both the great room and the primary bedroom, adding a spacious and airy feel. The primary suite offers a walk-in closet with shelving and a decorative display ledge. The dining area is just off the kitchen, providing easy access for meals to be served. The updated kitchen offers a pass-through opening for conversation with family and friends. You’ll love the convenience of the utility room and pantry off the garage, plus a private walkway leading to your own side entrance. Relax on your patio overlooking the golf course, the perfect spot to unwind or read. There is extra parking in the driveway and off-street. New HVAC system installed in 2024. This is one to see! Call today for a private showing.

1023 Winged Foot Court Unit A, South Chesapeake
2060 Maywood Street, South Chesapeake
$285,000
2 Beds ⋅ 1 Baths ⋅ 10608049 MLS
Adorable Bungalow situated on a half-acre lot. The detached garage has room for multiple cars. The room above offers a pool table that comes with the sale and plenty of storage. Freshly painted and new carpet throughout. Large walk-in closet. Buck stove offers a alternative heat source. Move in Ready.

2060 Maywood Street, South Chesapeake
2249 Tennessee Drive, South Chesapeake
$285,000
3 Beds ⋅ 1 Baths ⋅ 10606772 MLS
Come see this well-maintained 3 bedroom, 1 bathroom home sitting on just over an acre of land! This charming property features beautiful hardwood floors, a cozy living room, and an inviting front porch great for rocking or swinging while you enjoy the view.Outside, you’ll find plenty of options — park under the carport or in the large detached garage. The spacious fenced backyard offers room for play, pets, or relaxing, and there’s additional open land beyond the fence great for a garden, hobbies, or future projects.Don’t miss your chance to make this peaceful property your new home — come see it today!

2249 Tennessee Drive, South Chesapeake
1457 Leckford Drive, South Chesapeake
$285,000
3 Beds ⋅ 2.1 Baths ⋅ 10606627 MLS
Beautiful and move-in ready condo in desirable Brighton Park at Greenbrier! This light-filled home features new carpet throughout, fresh paint, and an open floor plan perfect for entertaining. Enjoy a private patio ideal for grilling or relaxing outdoors. Two spacious primary bedrooms each offer en-suite baths and walk-in closets, plus a bonus room perfect for an office or guest space. Community amenities include 2 pools, trails, water, sewer, ground maintenance, trash, exterior maintenance, lighting, roads, siding and roof-all covered by the condo association. Ample parking available throughout the community. Convenient location near shopping, dining and interstates.

1457 Leckford Drive, South Chesapeake
3613 Weiss Lane, South Chesapeake
$285,000
3 Beds ⋅ 1 Baths ⋅ 10602712 MLS
Discover this charming home in Chesapeake featuring 3 bedrooms, 1 bathroom, living room, laundry room and updated kitchen with SS electric range, SS dishwasher and SS microwave situated on a large lot. New paint and flooring throughout, ceiling fans and updated lighting. This house has close proximity to schools, shopping and more. Don't miss out! Schedule your showing today!

3613 Weiss Lane, South Chesapeake
303 Middle Oaks Drive, South Chesapeake
$285,000
2 Beds ⋅ 2.1 Baths ⋅ 10597350 MLS
Nicely appointed townhome, great location, and amenities. No HOA, POA or condo fees. Come see this home before it's gone. All upgrades are approx. 7 yrs old. HVAC was replaced 2019, New fence in 2025. Home is being sold "AS IS", seller willing to make some concessions with acceptable offer. Fireplace has been used for decorative only.

303 Middle Oaks Drive, South Chesapeake
1244 Mill Lake Quarter, South Chesapeake
$284,900
3 Beds ⋅ 1.1 Baths ⋅ 10612399 MLS
Welcome to 1244 Mill Lake Quarter. A charming 3 bedroom, 1.5 bathroom townhome perfectly situated in Greenbrier with beautiful lake views. This home features a bright and spacious living area with an updated kitchen, dining area, and living room which is perfectly centered around the wood burning fireplace. Downstairs you'll also find the half bathroom, and utility closet. Upstairs you'll find three comfortable bedrooms, a full bathroom, and plenty of storage. Enjoy peaceful mornings or relaxing evenings in your fully fenced in backyard with tranquil water views. Conveniently located close to shopping, dining, and the interstate.

1244 Mill Lake Quarter, South Chesapeake
901 Seabreeze Court, South Chesapeake
$284,200
3 Beds ⋅ 1.1 Baths ⋅ 10633805 MLS
Completely remodeled end-unit townhome next to the water. New flooring throughout, new paint, new bathrooms, updated kitchen with stainless appliances and granite countertops, backyard space perfect for gardening or relaxing outdoors, 2 parking spaces, fireplace as-is

901 Seabreeze Court, South Chesapeake
649 Mill Landing Road, South Chesapeake
$284,000
2 Beds ⋅ 1.1 Baths ⋅ 10619406 MLS
Super cute brick townhome in Great bridge. Kitchen has granite counters, stainless steel appliances, LVP flooring, freshly painted. Both bathrooms have been updated. Nice backyard with shed that has electric. Fireplace has not been used and is in as is condition. While in great condition home is sold as is. Seller offering a 1 year supreme 2/10 warranty.

649 Mill Landing Road, South Chesapeake
712 Inlet Quay Unit F, South Chesapeake
$283,500
3 Beds ⋅ 2 Baths ⋅ 10630813 MLS
Welcome to this spacious condo in the desirable Riverwalk community!! This home features an open-concept floor plan with a convenient first-floor bedroom. The kitchen and bathrooms were fully renovated in 2022, showcasing modern cabinetry and elegant granite countertops .New Carpet and LVP , Water heater replaced 2024. Step outside to a large private balcony—great for entertaining or relaxing. Residents enjoy a wide range of community amenities, including a clubhouse, swimming pools, scenic walking trails, and tennis courts. Don’t miss this opportunity—this one won’t last long!

712 Inlet Quay Unit F, South Chesapeake
1713 Orchard Way, South Chesapeake
$283,000
2 Beds ⋅ 2 Baths ⋅ 10641020 MLS
Welcome to 1713 Orchard Way—an inviting home offering comfort, style and versatility. Enjoy 2 dedicated parking spaces + ample guest parking & a charming covered front porch. 1st floor features incl BR with attached bath, soaring vaulted ceilings, new LVP flooring, fresh paint and cozy gas log FP, creating a bright, welcoming living space. Updated kitchen with new counters & SS appliances. Spacious primary BR offers large walk-in closet (easy attic access) & bath with relaxing Jacuzzi tub. Upstairs, HUGE loft/flex area ideal for office, gym or 3rd BR. Add’l highlights: new carpet, generous interior storage, ext storage & screened porch for seamless indoor/outdoor living. Community amenities incl pool. Conveniently located just minutes to bases, interstates, dining, shopping & all of Hampton Roads.

1713 Orchard Way, South Chesapeake
3501 Old Mill Road, South Chesapeake
$282,500
2 Beds ⋅ 2 Baths ⋅ 10586781 MLS
Don’t miss this incredible opportunity to make this 2-bedroom, 2-bathroom home your own! Situated on a .62-acre lot, this 1,884 sq ft property offers abundant space both inside and out, plus additional bonus areas great for a home office, guest space, or creative use. With a little TLC, this home can truly shine. Bring your vision and transform this property into a personalized haven or a smart investment. Whether you're a first-time buyer looking for a project, an investor, or someone ready to create your dream home, this is the great canvas. With so much potential in the heart of Chesapeake, this one may not last long. Call today for more information and to schedule your tour!

3501 Old Mill Road, South Chesapeake
1940 Woodgate Arch Unit A, South Chesapeake
$282,000
3 Beds ⋅ 2 Baths ⋅ 10650616 MLS
Welcome home to this beautifully updated 3-bedroom, 2-bath home, completely renovated in 2022! Thoughtfully refreshed from top to bottom, this move-in-ready gem offers a stylish, modern feel with updates designed for comfortable everyday living. The beautifully updated kitchen features crisp cabinetry, sleek countertops, stainless steel appliances, and plenty of space for cooking and gathering. All three bedrooms are bright and inviting, while both updated bathrooms offer fresh, modern finishes. With the major renovations already completed, you can simply move in and enjoy! Conveniently located near shopping, dining, schools, and major interstates, this home offers the perfect combination of comfort, style, and convenience. Whether you're entertaining, relaxing, or making new memories, this one is ready to welcome you home.

1940 Woodgate Arch Unit A, South Chesapeake
1204 Corkwood Circle, South Chesapeake
$282,000
3 Beds ⋅ 2.1 Baths ⋅ 10629899 MLS
Rare Find - Do not miss out! This end unit townhome on a culdesac features a downstairs primary suite with brand new carpet and attached full bathroom and two additional bedrooms upstairs. Step out of your bedroom and into your serene screened-in porch. The backyard offers a HUGE storage shed with built in shelves. Storage is not a problem inside either with a walk-in closet in the primary bedroom and a converted garage which could serve as extra storage/home office/craft room/etc. Plenty of parking in the expanded driveway too- can easily fit 3+ cars. HVAC system (including duct work) was replaced in 2024.

1204 Corkwood Circle, South Chesapeake
538 Hadleybrook Drive, South Chesapeake
$282,000
2 Beds ⋅ 2.1 Baths ⋅ 10617345 MLS
Move-in ready corner unit sought-after Greenbrier! Stylish light fixtures, abundant natural light, and a spacious open-concept layout connecting the living and dining areas to the updated kitchen with quartz countertops—ideal for everyday living and entertaining. This home features two primary suites, each with a full en-suite bath and oversized walk-in closet. Living space extends outdoors to a private, enclosed patio with additional storage. Assigned parking plus ample guest spaces. Condo dues include water, sewer, trash, pool, trails, grounds maintenance, and master insurance policy. Quiet, secluded setting just minutes from Greenbrier shopping, restaurants, and entertainment. Schedule a tour today!

538 Hadleybrook Drive, South Chesapeake
1628 Ballahack Road, South Chesapeake
$282,000
3 Beds ⋅ 1 Baths ⋅ 10608247 MLS
Enjoy the best of both worlds—peaceful country living just minutes from town! This updated 3-bedroom, 1-bath home offers an open floor plan and thoughtful upgrades, including a new roof, fresh exterior and interior paint, updated pump in the pump house, new bathroom flooring, and a new hot water heater. Located in a highly sought-after school district, this property provides comfort, privacy, and easy access to major routes, shopping, and dining. Move-in ready with modern updates and a quiet setting—perfect for anyone seeking a relaxed lifestyle with convenience close by.

1628 Ballahack Road, 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.

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