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201 Andiron Arch, South Chesapeake
$545,000
5 Beds ⋅ 2.1 Baths ⋅ 10635829 MLS
Welcome to this beautifully maintained home on a spacious corner lot backing directly to a city park, offering the perfect blend of privacy, outdoor space, and neighborhood charm. Chosen by the current owners for its ideal setting and room for kids to play, this home offers both comfort and functionality throughout. Inside, you’ll find a large kitchen with plenty of space for gathering and entertaining, along with a dedicated office and formal dining room for added flexibility. Several bedrooms are generously sized, including the oversized room across from the primary suite, previously used as a playroom. Located in the highly sought-after Grassfield High School district, residents also enjoy HOA amenities including a community pool and rentable clubhouse for events and gatherings. Thoughtful updates over the years make this home move-in ready and easy to enjoy from day one

201 Andiron Arch, South Chesapeake

941 Painted Lady Place, South Chesapeake
$644,900
4 Beds ⋅ 2.1 Baths ⋅ 10634473 MLS
This home shows pride of ownership located in sought after Grassfield area! This spacious 4 bedroom, 2.5 bath home offers an open & inviting layout filled w/ natural light. The first floor features an eat in kitchen open to the living room, formal dining area, guest half bath, & a flexible sitting room can be used for a home office, playroom, or study. Upstairs you'll find a large primary suite with tray ceilings, a custom walk in closet, and beautifully updated shower, and 3 additional bedrooms and convenient second floor laundry. Enjoy the benefit of solar panels that will be paid off at closing, helping keep utility costs low while you enjoy all this home has to offer. Step outside to your private backyard oasis featuring an inground saltwater pool, patio & oversized lot backing to woods. Updates include kitchen appliances 2024-2025, pool pump & filter 2022, salt cell 2025, pool light & diving board 2026, carpet 2021, well & sprinkler system, 3rd driveway & backyard walkway 2022

941 Painted Lady Place, South Chesapeake

331 Appaloosa Trail, South Chesapeake
$475,000
4 Beds ⋅ 2.1 Baths ⋅ 10632128 MLS
Welcome home to a home where comfort, style, and space come together beautifully! This charming 4-bedroom, 2.5-bath home has been thoughtfully updated with brand new flooring and stunning granite countertops, creating a fresh, modern feel throughout. Step inside to find a warm and inviting layout. The spacious kitchen flows effortlessly into the main living areas, making it easy to gather with family and friends. Upstairs, you’ll find generously sized bedrooms, including a relaxing primary suite designed for comfort at the end of the day. Out back, enjoy your own private retreat with a large fenced-in backyard. This home truly checks all the boxes. Don’t miss your opportunity to make it yours—schedule your private showing today!

331 Appaloosa Trail, South Chesapeake

503 Esterview Lane, South Chesapeake
$540,000
3 Beds ⋅ 2.1 Baths ⋅ 10630875 MLS
Fresh, updated, and completely move-in ready in Westfield at Hickory Manor—this 3 bedroom, 2.5 bath home built in 2020 offers a bright, open layout with modern finishes, fresh paint throughout, and thoughtful updates that stand out from the moment you walk in. The spacious living area is filled with natural light and flows seamlessly into the kitchen, featuring ample cabinet space, a pantry, and plenty of room for everyday living and entertaining. The primary suite offers a comfortable retreat with a walk-in closet and private bath, while two additional bedrooms provide flexibility for guests, a home office, or additional living space. Step outside to enjoy the patio space along with the convenience of an attached garage, all within a community that offers a clubhouse, fitness center, playgrounds, and walking trails close to shopping, dining, and major roadways. Don’t miss your chance, ask for our video tour or schedule your in-person showing today before it’s gone.

503 Esterview Lane, South Chesapeake

3216 Farange Drive, South Chesapeake
$535,000
4 Beds ⋅ 2.1 Baths ⋅ 10624338 MLS
$10,000 IN CLOSING COST ASSISTANCE OFFERED... use it to lower your rate or your cash to close. The spacious front porch overlooking the neighborhood park welcomes you to this beautiful home. Inside, tall ceilings and natural light create a bright, open feel with a layout designed for both everyday living and gathering. The kitchen flows into the main living area, while formal living and dining spaces offer flexibility for offices or additional living. Upstairs, four bedrooms include a spacious primary suite with two walk-in closets and a soaking tub. The large room over the garage adds versatility for a guest space, playroom, or media room. With new HVAC, new carpet, and access to neighborhood amenities, this home offers comfort, flexibility, and a setting that stands out.

3216 Farange Drive, South Chesapeake

301 Lomond Loop Unit 24, South Chesapeake
$912,971
2 Beds ⋅ 2 Baths ⋅ 10561975 MLS
Located in the highly desired Edinburgh neighborhood in Chesapeake, Tara Preston Homes presents an exquisite newly constructed 55+ Custom single family home. Although this new construction has not been built yet, it allows you the freedom to tailor exterior selections, paint colors, cabinets, countertops, and flooring to your taste. Boasting two spacious bedrooms and two full baths, this luxurious home is 2,005 sq. ft. Revel in the tranquilityof a tucked away neighborhood while still enjoying the convenience of shopping, dining, and easy Chesapeake Bypass access just minutes away. Lawn and flowerbed maintenance with irrigation and community common area with large gazebo and fire pit included with HOA dues. Only awaiting a 6 month build time. 1 year builder warranty and 5 year structural warranty included. Welcome home to The Cottages at Edinburgh.

301 Lomond Loop Unit 24, South Chesapeake

444 Fleming Circle, South Chesapeake
$464,000
4 Beds ⋅ 3 Baths ⋅ 10639032 MLS
Welcome to this well-maintained Chesapeake home tucked away on a cul-de-sac! Offering approximately 2,100 square feet of living space, this versatile property features 4 bedrooms, 3 full bathrooms, and plenty of room to fit your lifestyle. Inside, you’ll find fresh paint, abundant storage, and a flexible floor plan that includes a flex room, formal dining room, and a family room. The spacious eat-in kitchen offers ample cabinetry and storage, making meal prep and entertaining a breeze. One of the home’s standout features is the converted garage, creating a large additional living area complete with a full bathroom. This versatile space could serve as a second primary suite, guest quarters, media room, playroom, or whatever best suits your needs. Situated on a generous 0.4-acre lot, the expansive backyard provides endless opportunities for outdoor entertaining, gardening, or simply relaxing. Conveniently located near shopping, dining, schools, and major commuting routes.

444 Fleming Circle, South Chesapeake

733 Whisper Walk, South Chesapeake
$330,000
3 Beds ⋅ 2.1 Baths ⋅ 10638717 MLS
Beautifully located on the lake, this home includes part of the lake within its property lines. There is a spacious 1st-floor primary suite with walk-in closet, sun-filled full bath, including a large jetted tub & separate shower. Two additional BRs & a full bath are found upstairs. The loft area is used as one of the two upstairs BRs which currently overlooks the great room below with its cathedral ceiling and wall of windows. The trex-style deck overlooks the beautiful lake and includes a nice awning for those sunny afternoons. Easy access to the bulkheaded lake affords great fishing. The lot is huge (over 1/4 AC) and extends well to the right beyond the wood fence in the backyard (see plat map in listing documents). Being sold AS IS, seller believes all mechanicals and basic structure to be in good condition, but there are cosmetic repairs needed and updates to the kitchen and baths which will bring its new owner greater value. Similar homes have sold for $385K and $406K.

733 Whisper Walk, South Chesapeake

1440 New Mill Drive, South Chesapeake
$475,000
4 Beds ⋅ 2.1 Baths ⋅ 10636897 MLS
Gorgeous four bedroom home in the desirable Country Club Meadows community. Large windows throughout fill the home with natural light, creating a bright and inviting atmosphere. The main level offers a charming sitting area, a sunlit dining room, and a cozy living room with a fireplace. At the center of it all, the open kitchen features beautiful white cabinetry and stainless steel appliances. Upstairs, the primary suite includes a walk-in closet and a private ensuite bath, while three additional bedrooms are generously sized with ample closet space. Head outside to a spacious, fully fenced backyard featuring a covered patio and plenty of space for outdoor entertaining, gardening, or play. You'll also enjoy the attached garage providing additional storage and everyday convenience.

1440 New Mill Drive, South Chesapeake

716 River Hollow Court, South Chesapeake
$650,000
5 Beds ⋅ 3 Baths ⋅ 10636740 MLS
WELCOME HOME! Check out this beautiful 5-bedroom, 3 full bath ranch tucked away on a cul-de-sac! This spacious home features an open floor plan with gorgeous hardwood floors, a cozy gas fireplace, a large kitchen with granite countertops, stainless steel appliances and pantry. The main level offers 4 bedrooms and 2 full baths, while the second floor includes an additional bedroom, loft, full bath and a sizable walk-in attic that provides abundant storage or the potential to be converted into additional living space — perfect for guests, a private retreat or multi-family living! Additional features include a 2-car garage, lawn irrigation/sprinkler system, surround sound in the living room and CAT 5 wiring. Enjoy the large backyard complete with a paver patio and firepit, ideal for entertaining. No HOA, POA or flood insurance required. Seller is offering 3.25% VA assumption to VA buyers with substitution of eligibility. Call now for your private tour!

716 River Hollow Court, South Chesapeake

230 Marina Reach, South Chesapeake
$550,000
4 Beds ⋅ 2.1 Baths ⋅ 10633810 MLS
Welcome to Riverwalk, nestled along the Southern Branch of the Elizabeth River, where residents enjoy a boat dock, clubhouse, swimming pool, tennis courts, biking trails, playgrounds and more. This beautiful all-brick ranch on a crawl space offers timeless charm and comfortable living. The kitchen features custom-built cherry wood cabinets and opens to a spacious great room with vaulted ceilings and a cozy gas fireplace. Step outside to a large deck flowing down to an expansive concrete patio with pergola, perfect for entertaining or relaxing outdoors. Well designed landscaping provides vibrant color year-round, creating a private backyard retreat. Come see if this exceptional house, paired with riverfront community amenities and endless fun in the sun, is the perfect place for you to call home.

230 Marina Reach, South Chesapeake

4210 Cornland Road, South Chesapeake
$610,500
2 Beds ⋅ 2 Baths ⋅ 10631611 MLS
Set on an expansive 7.86+/- acres in Chesapeake’s desirable Hickory area, this property offers a rare blend of privacy, open space, and rural charm. The nearly eight-acre setting features a mix of wooded and open land, creating a peaceful and versatile environment ideal for a private retreat, recreation, or future potential. The 2,088+/- sq ft home is complemented by a detached garage with FROG, and separate workshop, providing comfort and functionality in a spacious countryside setting. Property will be sold at Auction on 5/20/26 at 11:00 AM, list price is starting bid only, final selling price TBD at live auction, with online bidding available. Sold as-is; seller will make no repairs. Termite and moisture inspection and home inspection reports are provided on the auction house website for informational purposes only. Pre-auction offers considered. Public preview 5/16/26 at 10:00 AM (no reservation required). Bid, Win & Sell Confidently!

4210 Cornland Road, South Chesapeake

516 Beecher Stowe Street, South Chesapeake
$607,500
4 Beds ⋅ 2.1 Baths ⋅ 10630895 MLS
Welcome to a home that blends timeless charm with thoughtful design and elegant detail. From the moment you arrive, the double front porches create a striking first impression Inviting you to slow down and enjoy the lifestyle this home offers. Inside, an open and light-filled floor plan showcases extensive trim work, custom built-ins, and architectural touches throughout. The main living area features a coffered ceiling and gas fireplace, while the formal dining room and eat-in kitchen provide the perfect balance of entertaining and everyday living. A secondary living space with a full built-in bookcase offers flexibility for an office, library, or lounge. Upstairs, the expansive primary suite includes vaulted ceilings, a sitting area, dual vanities, soaking tub, separate shower, and walk-in closet. Enjoy a fenced backyard with patio, all in a community with pool, parks, and more.

516 Beecher Stowe Street, South Chesapeake

608 Ravenstone Drive, South Chesapeake
$510,000
4 Beds ⋅ 2 Baths ⋅ 10630541 MLS
Welcome to 608 Ravenstone Drive—nestled in one of Chesapeake’s most sought-after neighborhoods! This beautifully maintained home offers the perfect blend of comfort, style and location. Step inside to find a warm and inviting layout designed for both everyday living and entertaining. The spacious living areas flow effortlessly, creating a bright and airy feel throughout. Whether you’re hosting friends or enjoying a quiet evening at home, this property delivers the ideal setting. The kitchen serves as the heart of the home, offering ample cabinet and counter space, perfect for preparing meals and gathering with loved ones. Generously sized bedrooms provide comfort and privacy, while the primary suite offers a relaxing retreat after a long day. Outside, enjoy a well-maintained yard with plenty of space for outdoor living—ideal for morning coffee, evening unwinding or weekend get-togethers. This home offers convenience to shopping, dining, schools and major routes.

608 Ravenstone Drive, South Chesapeake

815 Denham Arch, South Chesapeake
$715,000
5 Beds ⋅ 3 Baths ⋅ 10628778 MLS
Immaculate home in the Hickory area of Chesapeake. This home boosts 5 bedrooms, 3 full baths with one bedroom and full bath on 1st level. Living room or office with beautiful sliding French doors to the cozy family room with gas fireplace. Family room opens to the kitchen with stainless appliances, granite countertops with island and 2 pantries. Nice size dining room. Lovely primary suite w/tray ceiling and large walk in closet and a beautiful updated ensuite. Room over the two car garage is the 5th bedroom or perfect for a workout or entertainment room. Beautiful fenced in backyard with deck to enjoy those family barbeques. This cul-de-sac home is move in ready. You will want to call this your new home!

815 Denham Arch, South Chesapeake

410 Cobblewood Arch, South Chesapeake
$322,500
3 Beds ⋅ 2 Baths ⋅ 10638344 MLS
Completely Updated 3BR/2BA Canal-Front Home! Attached only by the garage, this beautifully renovated home offers the privacy and feel of a single-family residence. Recent updates include a stunning new kitchen with cabinets, countertops, and appliances; new LVP flooring; new carpet; fresh paint; updated bathrooms; updated windows; roof; HVAC; new water heater; new fixtures; new ceiling fans; and new hardware. The flexible floor plan features rare 1st floor primary, 3 bedrooms and 2 full bathrooms. Fully Fenced backyard overlooking a peaceful canal has two patios and a water view—perfect for relaxing, entertaining, pets, or play. Additional features include a one-car attached garage and a convenient location close to shopping, dining, schools, and major interstates. Move-in ready with the feel of new construction—just unpack and enjoy! Owner Agent.

410 Cobblewood Arch, South Chesapeake

608 Woodcott Drive, South Chesapeake
$610,000
5 Beds ⋅ 3 Baths ⋅ 10637938 MLS
Rare opportunity in the Hickory Section of Chesapeake! Welcome to 608 Woodcott Drive, tucked away on a private cul-de-sac with a spacious layout. This 5 bedroom 3 full bath home features a first floor multi-generational in-law suite. Added in 2019, this private suite is the true differentiator featuring its own separate entrance, large living/sitting area, bedroom space, closet, and accessible full bath with a custom tiled curbless shower. Perfect for extended family, guests, in-laws, parents, caregivers, or flexible work from home living. Large fenced in yard with a 2 car attached garage and shed for storage. The main home offers bright, comfortable living spaces with updated LVP flooring throughout, and a refreshed kitchen with updated countertops, tile backsplash, soft close cabinet doors, and GE Black Slate stainless appliances. The primary suite features a dual vanity and Jacuzzi fiberglass walk-in shower, while the guest bath has also been updated. Step outside and enjoy a private backyard retreat with a large Cambridge paver patio, mature landscaping, sprinkler system, ideal for entertaining, pets, play, or relaxing under the trees. Additional updates include new replacement windows, exterior siding/paint/fascia, stainless gutter guards, updated electrical service with subpanel, generator transfer switch connection. New gas water heater. Laundry room has a newer washer/dryer, with gas and electric hookups. Great Chesapeake location near shopping, dining, parks, interstates, military bases, and everyday conveniences. A flexible, updated home with the space and functionality for growing or multi-generational families.

608 Woodcott Drive, South Chesapeake

328 Hagenspring Road, South Chesapeake
$595,000
6 Beds ⋅ 3 Baths ⋅ 10637201 MLS
Welcome home! This spacious 6-bedroom, 3-bath home offers over 2,850 square feet of versatile living space designed for today's lifestyle. The flexible floor plan features a first-floor bedroom and full bath, making it ideal for guests, play room, multigenerational living, or a home office. The updated kitchen with large island & farm house sink showcases modern high-end finishes and opens seamlessly to the inviting family room with a cozy gas fireplace, creating the perfect space for everyday living and entertaining. Soaring ceilings and abundant natural light add to the home's warm and welcoming feel. Step outside to enjoy the privacy-fenced backyard complete with a new stamped patio, providing the perfect setting for cookouts, gatherings, or relaxing evenings around the fire pit. Additional features include a two-car garage, paid off solar panels (low energy costs!), and plenty of space for work, play, and abundant storage in this house. Conveniently located near parks, walking trails, shopping, dining, and major commuter routes including I-64, I-464, and Route 168. Best of all, there is no HOA and no flood insurance required. This beautifully maintained home offers the perfect combination of space, updates, and location. Don't miss your opportunity to make it yours!

328 Hagenspring Road, South Chesapeake

823 Rivanna River Reach, South Chesapeake
$315,000
2 Beds ⋅ 2 Baths ⋅ 10636110 MLS
Welcome to this beautifully renovated condo in the desirable Kingsford section of the Riverwalk community! Offering 2 bedrooms, 2 baths, and an open-concept layout, this home blends modern updates with comfortable living. The stunning kitchen is a true centerpiece, featuring quartz countertops, stainless steel appliances, and brand-new soft-close cabinetry—perfect for entertaining and everyday life. Fresh interior paint, plush new carpet, and durable luxury vinyl plank flooring create a stylish, cohesive feel throughout. Cathedral ceilings and abundant natural light make the living spaces feel bright and airy. Upstairs, enjoy a versatile loft-style office/flex space along with a spacious primary suite complete with a walk-in closet and private ensuite bath. Conveniently located near interstates, schools, shopping, and dining, this home also offers low-maintenance living with condo association coverage that includes exterior building maintenance.

823 Rivanna River Reach, South Chesapeake

967 Saint Andrews Reach Unit D, South Chesapeake
$230,000
2 Beds ⋅ 2 Baths ⋅ 10636147 MLS
6/11/26 - BOM THROUGH NO FAULT OF THE SELLER. Two story corner unit within the Saint Andrews Condo neighborhood. One of the closest units to the golf course and plenty of green space just out your front door! Very open first floor with an updated kitchen, and the upstairs primary bedroom features it's own full bathroom. New roof installed in 2024, BRAND NEW LVP flooring and carpet, updated light fixtures, and recently painted. The attic has plenty of storage space, and both bedrooms have generous closet space and wonderful views of the golf course. Condo fees include the water/sewer and trash pickup, as well as ground maintenance. 2 parking spots are reserved for this unit. Conveniently located near interstates, YMCA and Greenbrier shopping areas.

967 Saint Andrews Reach Unit D, 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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