South Chesapeake VA Single Family Real Estate, Homes for Sale

This beautifully maintained and tastefully designed 4 bedroom home in the highly sought after community of Culpepper Landing is waiting for you to call it home! At only 11 years old, it offers the peace of mind of low maintenance on your high ticket items such as HVAC, roof and windows. Not to mention, fresh paint floor to ceiling throughout, year old flooring on stairs and upstairs, the spacious front porch, dual walk-in closets in the primary bedroom and the perfect open concept downstairs living space with ample natural light and 9' ceilings. The 4th Bedroom on the main level is the perfect flex space, ideal for a home office, playroom or guest room! The golf-cart friendly community offers low maintenance living with exceptional neighborhood amenities, including a community pool, clubhouse, fitness center, playground and even a dog park! An additional benefit, a brand new elementary school is scheduled to open in 2027, tucked right inside of the neighborhood! Truly move in ready, this home offers comfort, style and convenience!

513 Simpson Lane, South Chesapeake

$439,900

4 Beds ⋅ 2.1 Baths ⋅ 10643438 MLS

Welcome home to this beautifully updated 4-bedroom, 2.5-bath home offering comfort, style, and peace of mind! The inviting floor plan is perfect for everyday living and entertaining, featuring a spacious living area with an electric fireplace and an updated kitchen with an oversized quartz island, new sink, faucet, and dishwasher. Enjoy the large privacy-fenced backyard with a Leonard metal storage shed. Recent updates include professionally painted interior and garage, new front and garage entry doors, updated primary bath vanity and toilet, new primary bedroom ceiling fan, all-new CO2 and smoke detectors, and a 50-gallon water heater. Major improvements include a new roof (2020) and replacement windows (2021). See attached list for additional updates. All appliances convey. Truly move-in ready!

2521 Southern Pines Drive, South Chesapeake

$374,900

4 Beds ⋅ 2 Baths ⋅ 10643138 MLS

Wonderfully updated and absolutely meticulously maintained and spotless ranch style home with 4 bedrooms 2 baths a 2 car DETACHED GARAGE in this lovely Chesapeake waterfront neighborhood! Modest sized home that comes to life with an open concept lover's dream!! This is the perfect house for entertaining! Sprawl out on the kitchen island and enjoy hosting- make sure to invite all your friends; the driveway and backyard can hold just about anyone and anything! Exclusive access to a public boat ramp—perfect for weekend adventures on the water!! Enjoy the convenience of a dedicated laundry room, and take full advantage of the expansive, fully fenced backyard—perfect for pets, play, and outdoor gatherings. Everything in the home has been updated in the last few years. Roof, hvac, water heater, flooring, kitchen, bathrooms and all new appliances. It’s all virtually new. All that’s missing is YOU!

1089 Saint Julian Drive, South Chesapeake

$720,000

5 Beds ⋅ 2.1 Baths ⋅ 10643367 MLS

Located in the highly sought after Hickory School District, this exceptional 5 bedroom, 2.5 bath home in Hickory Landing offers the timeless design, flexible floor plan, and quality finishes today's buyers are looking for. Years of thoughtful improvements throughout have enhanced this home inside and out. Enjoy peaceful pond views from the covered front porch before going into a welcoming foyer with impressive architectural details and wide plank hardwood floors. The formal dining room and versatile first floor bedroom provide flexibility for guests or a home office. At the rear of the home, the spacious family room with custom built ins and a gas fireplace flows effortlessly into the kitchen and casual dining area. The kitchen features gas cooking, stainless steel appliances, abundant cabinetry, and is designed for everyday living and entertaining. The inviting three season room overlooks the professionally landscaped, fenced backyard, while the finished room over the garage provides exceptional bonus space. Highlights include a beautifully remodeled primary bath, new carpet throughout the upstairs bedrooms, custom laundry room cabinetry, and a black wrought iron fence. Conveniently located just minutes from the Edinburgh shopping area with easy access to Target, dining, entertainment, the YMCA, and everyday conveniences.

1932 Ferguson Loop, South Chesapeake

$669,900

4 Beds ⋅ 2.1 Baths ⋅ 10643473 MLS

Your new home in Hickory awaits! Expertly crafted by Kirbor Homes, this beautiful home is only 4 years old and meticulously cared for! Featuring 4 spacious bedrooms and 2.5 baths, this gem sits on over 4 1/2 acers! Board and batten accent siding, rear covered porch, custom built in closets, tile shower in primary bathroom are just the beginning of the upgrades! Kitchen features beautiful white cabinetry, 8ft island, and stainless appliances. Walk in closets in all bedrooms, tons of storage space and so much more! All with no HOA in a Hickory School neighborhood! Schedule your personal tour today of this move in ready Hickory gem today!

141 Indian Creek Road, South Chesapeake

$1,104,938

4 Beds ⋅ 3.1 Baths ⋅ 10643126 MLS

Warning: You may never want to leave home! Welcome to the Buena Vista by Kirbor Homes, where every room is designed to make everyday life feel a little more extraordinary. Whether you're hosting the holidays, cheering on your favorite team, or simply enjoying a quiet evening in, this home is ready for it all. The show-stopping kitchen is sure to become everyone's favorite gathering spot, featuring our upgraded Chef's Appliance Package, an oversized island, and plenty of room for everything from charcuterie boards to cookie decorating marathons. The open-concept layout keeps the conversation flowing from the kitchen to the dining area and great room, so no one ever misses out on the fun. When it's time to recharge, the luxurious first-floor primary suite offers the perfect escape, while the additional bedrooms and flexible living spaces provide endless possibilities for guests, hobbies, a home office, or that home gym you've been promising yourself. Step outside to the covered rear porch and imagine slow mornings with coffee, backyard cookouts, or winding down with a glass of wine as the sun sets. Located in the desirable Sanderson Estates, the Buena Vista pairs spacious homesites with the quality craftsmanship and thoughtful details Kirbor Homes is known for. This isn't just another new construction home—it's the kind of place where memories are made, traditions begin, and you'll happily volunteer to host every family gathering. Schedule your tour or Design Center appointment today and see why the Buena Vista might just ruin every other floor plan for you. Builder contract. Ask about available lender incentives!

2801 Raccoon Trail, 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

$585,000

4 Beds ⋅ 2.1 Baths ⋅ 10643196 MLS

Welcome to this one of a kind custom all brick home designed for buyers who appreciate true craftmanship, architectural character, and timeless traditional design. Offering nearly 3000 sqft, 4 bedrooms and 2.5 baths, this home showcases features rarely found in newer construction, including a stunning wood spiral staircase, custom millwork, rich hardwood flooring, and 3 fireplaces that bring warmth and character throughout. This is not a builder grade flip or cookie cutter renovation, but a home built with quality, detail, and lasting charm. Outside, enjoy a private backyard retreat with a saltwater inground pool. Ideally located near local bases, shopping, dining, and major interstates, this is a rare opportunity to own a home with true character and lasting value.

913 Montebello Circle, South Chesapeake

$605,000

4 Beds ⋅ 2.1 Baths ⋅ 10642996 MLS

Welcome to luxury, low-maintenance living in the highly sought-after Westfield at Hickory Manor! This beautifully upgraded Galloway Model, built in 2018, offers 2,059 sq ft of stylish, thoughtfully designed living space with quality finishes throughout. The open-concept layout is superb for everyday living and entertaining, featuring spacious, light-filled rooms, an upgraded kitchen, a private primary suite, and flexible additional bedrooms. Enjoy resort-style amenities including a pool, 24-hr fitness center, clubhouse/community center, and playgrounds. Located in the sought-after Hickory School District with easy access to shopping, dining, military bases, major interstates, and more, this move-in ready home offers comfort, convenience, and lifestyle. Schedule your private showing today!

508 Cavendish Way, 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

$699,000

5 Beds ⋅ 2.1 Baths ⋅ 10642890 MLS

This property is a gardener's dream. It has a variety of flowering plants that provide blossoms throughout the growing season. Blooms are sequenced for near year round color. There are 10 field-stone edged garden beds add stunning features to the landscape. One garden bed in the back has a goldfish pond. One in the front features an unique natural stone bench. Back yard includes vegetable garden plot that faces the sun for garden fresh produce. Back yard oasis includes a hot tub and six foot privacy fence. Two patios are connected by a master-crafted pave walk-way. Oversized garden shed helps keep garage clutter free. Two lockable gates one on each side of the property. In ground sprinkler system fed by well water to keep watering cost low. Two outdoor water taps fed by the well and two additional taps fed by city water. Tank-less water heater provides endless hot water. The oversized primary bedroom includes two walk in closets. One large walk-in closet features two side cubby units for storage. The other walk in closet is medium sized with plenty of storage space. Washer and dryer are on the second floor for convenience to bedrooms.

707 River Gate Court, South Chesapeake

$250,000

3 Beds ⋅ 1 Baths ⋅ 10642992 MLS

Charming ranch nestled on a spacious lot in Chesapeake! This 3 bedroom, 1 bath home offers a warm and inviting layout that’s ready for you to make your own. Enjoy the convenience of a detached two-car garage, plenty of driveway parking, and a large yard with endless possibilities for entertaining, gardening, or simply relaxing. There’s even room to park your boat, RV, trailer, or recreational toys! Whether you’re a first-time homebuyer, downsizing, or looking for a property with space to spread out, this home offers the perfect blend of comfort, functionality, and outdoor living. Conveniently located with easy access to shopping, dining, schools, and major highways, this is one you won’t want to miss! * Some photos are virtually enhanced or staged*

2420 Payne Road, South Chesapeake

$615,000

3 Beds ⋅ 3 Baths ⋅ 10643157 MLS

This beautifully updated brick home combines comfort, functionality, and style with flexible spaces designed for modern living. At the heart of the home, the stunning kitchen features a custom island perfect for gathering, entertaining, and everyday life. Spacious bedrooms, versatile living areas, and an expansive sunroom provide plenty of room to spread out, with ideal spaces for a home office, virtual learning, hobbies, or creative pursuits. A true standout feature is the oversized two-car garage/workshop, complete with a full bath and approximately 780 square feet of unfinished space above—offering endless possibilities for guest accommodations, a studio, home gym, office, or additional storage. Step outside to enjoy beautifully landscaped grounds, custom decking, and an inviting patio designed for entertaining. A charming custom she-shed adds even more versatility, along with an additional flex space inside the home. Thoughtful updates throughout and adaptable spaces are a win!

103 Ashley Road, South Chesapeake

$729,000

4 Beds ⋅ 2.1 Baths ⋅ 10643077 MLS

Sitting on just under 1 ACRE escape to your own private retreat in the heart of Hickory! Nestled on a peaceful wooded setting, this beautifully maintained home offers the perfect blend of space, comfort and modern updates. Inside, you'll find souring ceilings, abundant natural light, and inviting living spaces designed for both relaxing and entertaining. Enjoy the tranquility of country style living while still being conveniently located near shopping, dining, and sought after schools. Major system updates provide peace of mind including updated heat pump, septic improvements, well and water filtration updates, gutter systems enhancements, oversized shed, extended driveway offering ample space for boat or RV storage, and a generator hookup. This property combines rural charm with everyday practicality. Whether you're hosting guests, enjoying quiet mornings outdoors, or simply looking for more privacy and space, this property offers a rare opportunity to enjoy the best of Chesapeake.

1740 Land Of Promise Rd Road, South Chesapeake

$949,608

4 Beds ⋅ 3.1 Baths ⋅ 10643106 MLS

Welcome to the Kentland by Kirbor Homes; where your Pinterest board finally gets to come to life! Designed for the way you really live, this home offers the perfect blend of style, comfort, and flexibility. With a luxurious first-floor primary suite, spacious open-concept living, and room to spread out upstairs, there's a place for everyone (and everything). The chef-inspired kitchen is ready for everything from holiday feasts to takeout nights, featuring our upgraded Chef's Appliance Package, a large center island, and plenty of space to gather. The great room is designed for game nights, movie marathons, or simply relaxing after a long day. Located in the sought-after Sanderson Estates, you'll enjoy spacious homesites, beautiful surroundings, and the quality craftsmanship Kirbor Homes is known for. Whether you're entertaining friends, hosting family, or just enjoying a quiet morning coffee on the porch, the Kentland is ready to fit your lifestyle. Come see why your next chapter deserves a home this fun to live in! Contact Listing Agent to schedule a tour or appointmnet at our design center today! Builder contract. Ask about Lender incentives!

1516 Cedarville Court, South Chesapeake

$900,000

7 Beds ⋅ 4 Baths ⋅ 10643086 MLS

Welcome home! This beautifully updated 7 bedroom and 4 full bath property offers over 3 acres of land and ample parking. First floor primary suite features a fireplace and upgraded bathroom with sleek tile. The kitchen boasts a large island, all new countertops, stainless steel appliances, and tile backsplash. Two upstairs bedrooms include full baths and walk-in closets. Open layout with recessed ceiling lighting, two fireplaces, and two sets of sliding glass doors lead to a spacious backyard. Schedule your showing today!

537 Margaret Drive, South Chesapeake

$479,000

4 Beds ⋅ 2 Baths ⋅ 10642873 MLS

Tucked away on a quiet wooded cul-de-sac in Brandermill, this quality-built 4-bedroom, 2-bath home blends timeless charm with modern updates. New Architectural roof, new beautifully renovated bathrooms, new kitchen countertops, newer LVP flooring. Centrally located dining area creates the warm, functional heart of the home. A spacious sun-filled addition with cathedral ceiling opens to the perfect patio gathering area for cookouts and a large backyard made for entertaining, yard games and having fun with family and friends. Unwind on the spacious shaded front porch and soak in the peaceful surroundings. This home has been thoughtfully maintained, a genuine gem offering comfort, character and is convenient to schools, shopping, dining and everyday essentials. Sparkling with style and ready to welcome you home!

804 Greenspring Court, South Chesapeake

$372,000

4 Beds ⋅ 2 Baths ⋅ 10642985 MLS

Don't miss your chance to own this beautiful and tastefully updated home in Deep Creek. This 4 BR home features the following updates completed in 2022: new plumbing throughout, remodeled bathrooms, new HVAC, water heater and windows. The converted garage is the perfect space for an office or bonus living area. The neighborhood is conveniently located near parts, schools, and several shopping centers. Schedule your showing today!

1107 Sean Drive, South Chesapeake

$540,000

4 Beds ⋅ 2 Baths ⋅ 10642998 MLS

Welcome to 233 Downing Drive, where everyday living feels easy, comfortable, and connected. Set in Chesapeake’s Tunbridge Station, this 4-bedroom, 2-bath home offers approximately 2,046 square feet with an open floor plan designed for gathering, relaxing, and enjoying time at home. Start your mornings in the bright all-season room, host dinner with room to spread out, then step outside to your own backyard retreat. The above-ground pool is surrounded by Trex decking, creating the perfect setting for summer afternoons, weekend cookouts, and unwinding with friends. When the day slows down, the hot tub conveys and is ready for quiet evenings under the stars. The detached workshop with power gives you space for projects, storage, hobbies, or tools. Inside, enjoy a first-floor bedroom and full bath, updated kitchen, refreshed baths, walk-in attic, pantry, and flexible spaces. With a fenced backyard, attached 2-car garage, and thoughtful updates, this home is ready for its next chapter.

233 Downing Drive, South Chesapeake

$999,985

6 Beds ⋅ 4 Baths ⋅ 10642034 MLS

This gorgeous home can be your "White-House"!! Step into this ALL-White brick 2-story contemporary home with front porch, arches and large foyer, and be ready to fall in love! 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 that is perfect for entertainment, an archway to the 2 first-floor bedrooms (one currently being used as an office), full bath with shower and another archway to the large familyroom with gas fireplace. You will be excited by the huge open kitchen with granite counters, an oversized island, eat-in area and pantry. Also, on the first level is an archway inset that holds the Stiltz-Lift (elevator). Either take the wooden stairs with wrought-iron railings or the Stiltz 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. The primary bedroom has a gas fireplace and a wall of glass windows and french doors that lead to the Juliet balcony. 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 Stiltz lift doorway. The extra-large 3-car garage has enough room for your cars or anything else. BUT there's more!! YES, then there's the backyard oasis! Well, you'll just have to see it for yourself. This home is convenient to shops, restaurants, malls, stores, Greenbrier Country club, banks, parks, interstate, university and so much more!

1324 Simon Drive, South Chesapeake

$580,000

4 Beds ⋅ 3 Baths ⋅ 10642916 MLS

Retreat to the expansive second-level primary suite, featuring a private sunroom, spacious loft, luxurious garden tub, separate tiled shower, and beautiful cherry hardwood flooring. The main level offers three additional bedrooms, two full bathrooms, and a generous sunroom complete with a built-in bar—perfect for entertaining or relaxing. Enjoy 3.16 acres of peaceful outdoor living, featuring a barn, chicken coop, and storage shed, offering endless possibilities for hobbies, animals, or gardening. Major updates provide peace of mind, including a new roof (2017), two-zone HVAC system (2020), and water heater (2023). Fresh interior paint throughout and brand-new downstairs carpet make this home truly move-in ready. Welcome Home!

2600 Saint Brides Road W, South Chesapeake

$499,900

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. Loan is assumable.

405 S Monterey Drive, South Chesapeake

$755,000

5 Beds ⋅ 3.2 Baths ⋅ 10642808 MLS

A Full Acre. Two Primary Suites. Room for Everyone — 1833 Benefit Rd, Chesapeake VA. Over 3,600 sf. Motivated sellers! Renovated 5-bedroom home on a full acre in Chesapeake — brand new carpet, all freshly painted. The space, privacy, and flexibility that rarely come together at this price point. Two primary suites, one up and one down, give you real options: multigenerational living, long-term guests, or a main-level owner's retreat. The downstairs in-law suite has its own private entrance — space for older parents, adult kids, or a home business with client access that never touches your living space. The renovated kitchen features stainless steel appliances and opens to living areas built for gathering. The upstairs primary offers double sinks and a large walk-in closet. A mudroom with half bath handles the daily traffic so the rest of the house stays put together. Outside is where this property separates itself. A wrap-around deck surrounds the above-ground pool — your built-in venue for summer weekends. The roundabout driveway and attached 2-car garage mean parking is never a problem, whether it's a cookout for twenty or just everyday life. And the full acre gives you room to add, expand, or simply breathe — no neighbors ten feet from your window. Homes with this much land, this much flexibility, don't sit long in Chesapeake. Schedule your showing today.

1833 Benefit Road, South Chesapeake

$135,000

2 Beds ⋅ 1 Baths ⋅ 10642815 MLS

Investor Special! Selling completely “as is”. Seller to do NO repairs. All contents of house, attic and yard convey to buyer at closing. HVAC is approximately 10 years old. Roof is approximately 8 years old. Gas Water heater new in 2025. Floored attic space. Cash or Renovation Loans only. Buy it, renovate it (cost to renovate estimate approximately $50k) and live there! Or fix it and flip it and make some moola! Probable value after renovations $200k or more. Nice sized fenced yard. Many newer homes on the street. Buy it, renovate it and rent it out! Great income producing potential. Or, knock it down and build a whole new house! You decide! Priced well below city assessed value. Hurry! This one won’t last.

1025 Calloway Avenue, South Chesapeake

$550,000

4 Beds ⋅ 2 Baths ⋅ 10642398 MLS

Welcome to 529 Royal Grant Drive in the desirable Cheshire Meadows area of Chesapeake. This well-maintained 4-bedroom, 2-bath ranch offers approximately 2,064 square feet of living space with a comfortable layout, office/study, finished room over the garage, and attached 2-car garage. The updated kitchen features granite countertops and stainless appliances, along with cathedral ceilings, skylights, a wood-burning fireplace, updated bath tile and fixtures, new interior paint, updated exterior vinyl trim, new exterior doors, and a new garage door and opener. The backyard is perfect for relaxing or entertaining with a deck, patio, privacy fence, storage shed, and salt system in-ground pool with new liner. Conveniently located near Great Bridge schools, shopping, restaurants, and commuter routes. A wonderful opportunity in a sought-after Chesapeake location. Listed at $550,000.

529 Royal Grant Drive, South Chesapeake

$459,900

3 Beds ⋅ 2 Baths ⋅ 10642749 MLS

Welcome to this lovingly maintained, one-owner ranch-style home nestled on 3 private acres. This well-built residence has been meticulously cared for and is ready for its next chapter — offering the perfect canvas for cosmetic updates to make it entirely your own. The open, manageable layout is ideal for those seeking single-level living with room to breathe. A standout feature is the oversized detached 2-car garage/workshop, perfect for hobbyists, car enthusiasts, or anyone needing serious storage and workspace. The expansive acreage provides privacy and tranquility rarely found at this price point, with mature surroundings that create a true retreat from the everyday. Whether you are looking to personalize a solidly built home or simply enjoy the peace and space this property offers, the opportunity here is undeniable. Priced to reflect its cosmetic potential while honoring the exceptional care this home has received throughout its single ownership.

3600 Martin Johnson Road Unit RD, South Chesapeake

$1,750,000

4 Beds ⋅ 4 Baths ⋅ 10642797 MLS

Set at the end of a quiet Hunters Ridge cul-de-sac, this custom brick estate rests on three private, gated acres, held by a single owner since its 2006 build. Beyond its 5,707 square feet of main finished living space, the home offers approximately 1,800 additional square feet of year-round conditioned space. A two-story foyer with a curved staircase opens to formal rooms and a two-story great room with a see-through gas fireplace. The island kitchen features granite, stainless, and a wet bar. The primary suite is a private retreat with a tray ceiling and a spa bath with a soaking tub. A temperature-controlled pool room, a rarity in Hunters Ridge, holds a heated pool beneath vaulted, skylit ceilings for year-round swimming and entertaining. A detached guest suite of about 715 finished square feet adds a kitchenette and full bath, ideal for extended family or long-term guests. A three-car garage, brick-pillar drive, pergola with hot tub, and patios complete the grounds.

2505 Sylvia Court, South Chesapeake

$775,000

5 Beds ⋅ 2.1 Baths ⋅ 10642786 MLS

One of a kind property in Hickory area of Chesapeake with 2 (YES TWO) SFH that are legally deeded, WATERFRONT (ocean access) ~3.5 ac lot, with no neighbors in sight! Main house is over 3,000 sqft 5/2.5. Smaller house about 1200 sqft, 2/. Both have newer systems and New Roofs. Each home has its own Septic/Well system & pumped in 2024-large house/2025-small house. Property backs to 60 ft of riverfront that leads through the sounds and into the ocean. The main farmhouse has modern amenities but the old charm and character with original hardwoods, curved arches and entry ways, Juliet Balcony overlooking estate, 3rd floor finished attic bonus room and solid walk down basement foundation that can be turned into a finished room or used for storage. This home is solid and well maintained, being sold as is, seller to make no repairs. Call today for your private showing!

112 Station Road, South Chesapeake

$534,900

5 Beds ⋅ 2.1 Baths ⋅ 10642746 MLS

Welcome home to lakefront living in sought-after Bryant Farms! From cozy nights by the custom gas fireplace to lazy mornings soaking in peaceful water views. The open-concept family room and kitchen create the perfect heart-of-the-home feel, while formal living and dining rooms offer beautiful hardwood and tile floors for those special gatherings. Chefs will love the eat-in kitchen, featuring a center island, granite countertops, a full pantry, and stainless steel appliances including a Frigidaire Gallery gas range and fridge. Step outside to the screened porch — your new favorite spot for morning coffee or unwinding after a long day. Upstairs, retreat to a spacious primary suite with a walk-in closet, double vanity, soaking tub, and separate shower. Three additional bedrooms, including a generous FROG, offer flexible space for family, guests, or a home office, and full guest bath.

2428 Annie Circle, South Chesapeake

$369,500

3 Beds ⋅ 2.1 Baths ⋅ 10642744 MLS

Beautifully maintained 3 bedroom, 2.5 bath detached condo offering the perfect blend of comfort, style, and high end living. The spacious interior features granite countertops, stainless steel appliances, and a custom built nook tucked beneath the staircase, adding both character and functionality. Thoughtfully updated, this home includes a new roof, windows, and water heater (all 2021), plus an HVAC system replaced in 2022 for added peace of mind. Every detail has been well cared for, making this move in ready home an exceptional opportunity. Don't miss your chance to own this inviting property with modern updates and timeless appeal.

732 Fallcreek Run, South Chesapeake

$950,000

5 Beds ⋅ 4 Baths ⋅ 10642562 MLS

Welcome to your own private backyard retreat! This beautifully updated home offers the perfect blend of stylish interior living and incredible outdoor entertaining. Step outside to a true backyard oasis featuring a stunning 6-foot in-ground pool with a new liner and pump, a covered lounge area, outdoor fire pit, built-in bar, outdoor kitchen with grill, and plenty of space to host family and friends all season long. A screened porch conveniently connects the outdoor living space to the home, creating seamless indoor-outdoor living. Inside, the nearly renovated kitchen is the heart of the home, showcasing gorgeous marble countertops, a spacious center island, all LG appliances, bar-height seating, and a built-in desk area great for working from home or everyday organization. The open-concept design flows effortlessly into the inviting living room, making entertaining easy. Upstairs, you'll find generously sized bedrooms with abundant closet space, including a spacious room over the garage that offers endless possibilities for a media room, playroom, guest suite, or home office. The luxurious primary suite is a true retreat, featuring a cozy sitting area with its own fireplace, an oversized walk-in closet, and a beautifully appointed en-suite bath complete with dual-height vanities, a private water closet, soaking tub, and separate walk-in shower. Light wood-look luxury vinyl plank flooring adds warmth and elegance throughout the main living areas, while plush carpeting creates comfort upstairs. Thoughtfully updated and impeccably maintained, this home offers the perfect combination of comfort, style, and resort-style outdoor living. Don't miss the opportunity to make this exceptional property your next home!

129 Greengable Way, South Chesapeake

$425,000

4 Beds ⋅ 2 Baths ⋅ 10642702 MLS

Pride of ownership shines throughout this beautifully maintained 4-bedroom, 2-bath ranch nestled on a corner lot in the desirable Clearfield community. From the moment you arrive, you'll be welcomed by impeccable curb appeal, lush landscaping, and vibrant flower beds that create a beautiful first impression. Inside, you'll find over 2,100 square feet of comfortable living space featuring a cathedral ceiling, a cozy gas fireplace, a spacious primary suite with a private bath, and a finished room over the garage that offers endless possibilities as a home office, playroom, or flex space. Relax on the covered rear deck, enjoy the privacy-fenced backyard, and appreciate the convenience of the attached 2-car garage. No HOA! Conveniently located near shopping, dining, schools, and major commuter routes. This lovingly cared-for home is ready to welcome its next owners.

500 N Hills Drive, South Chesapeake

$545,000

4 Beds ⋅ 2.1 Baths ⋅ 10642683 MLS

WELCOME HOME! Check out this beautifully updated 4 bed, 2.5 bath home in the highly desirable Stonegate neighborhood and Great Bridge School District! This home features a cook's dream kitchen w/ tons of cabinets, granite counters, new LVP downstairs and updated bathrooms. Outside enjoy an above ground pool with a deck, spacious patio fire pit and pergola. Seller is offering 2.375% VA assumption to VA buyers with substitution of eligibility. No HOA/POA or flood insurance. There is a voluntary Civic League in this community. Call now for your private tour!

909 Cantor Street, South Chesapeake

$639,000

4 Beds ⋅ 2.1 Baths ⋅ 10642673 MLS

Welcome to your private country retreat! Nestled on 3 beautiful acres in the desirable Grassfield School District, this custom-built 2014 home offers the perfect blend of space, comfort, and privacy. Featuring 4 spacious bedrooms, 2.5 baths, and an open-concept layout for entertaining, this property is designed for both everyday living and peaceful relaxation. Enjoy the charm of country living with modern conveniences, surrounded by serene views and plenty of room to roam.

2828 Seven Eleven Road, South Chesapeake

$455,000

3 Beds ⋅ 2.1 Baths ⋅ 10642666 MLS

Beautiful 3 bedroom 2.5 bath home in the desirable Grassfield area of Chesapeake. This home offers a spacious layout with plenty of room for everyday living and entertaining. The kitchen has lots of cabinet and counter space and opens to the dining and living areas. The primary bedroom features a private bath and a walk-in closet. Roof replaced in 2017, windows replaced in 2021 and HVAC in 2025 for added peace of mind. Step outside to a fenced backyard that's great for kids, pets, or weekend cookouts. Conveniently located near Grassfield schools, shopping, restaurants, and interstate access. Move in ready and waiting for its new owners!

440 Fleming Circle, South Chesapeake

$889,000

3 Beds ⋅ 2 Baths ⋅ 10642255 MLS

If these walls could talk, they would tell you 175 years of stories. Rare pre-Civil War farmhouse charm meets modern comfort in this private retreat that feels like a vacation every day. This 2-story home is filled with character, featuring 4 fireplaces, gorgeous original hardwood floors, 10-foot ceilings, hand-sawed original moldings, intricate ceiling details, and antique lighting. The living room offers a cozy wood-burning stove, while the family room showcases coffered ceilings and original hardwood floors. The spacious primary suite stands out with a beautiful fireplace and a wall of built-in cabinetry offering storage rarely found in modern homes. Enjoy two laundry areas, including one in the ADU over the detached tandem 4-car garage, plus a flexible space for an office or mudroom off the back of the main house. Outside, unwind and entertain by the pool oasis, or sit on the 250 sqft covered porch. There is a huge new chicken coop (26), and 2 dog runs for that farm life as well as a shed (as is). The brick walkways are the original bricks from the chimney repurposed. Updates include painted kitchen cabinets/walls (26), sealed and painted metal roof with 20 year paint (26), new pool liner (25), encapsulated crawlspace with dehumidifier/support beams (25), 50-gallon hot water heater (25), HVAC, and ductwork (23), new steps and railing out to the pool (26), breaker upgrade to house (25) 2 solar systems one to the main house and one to the ADU/garage (23). More updates listed in agent remarks. Near Hickory schools, shopping, Bypass, and OBX. Come own a piece of history in Hickory!

2410 Centerville Turnpike, 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

$535,000

4 Beds ⋅ 2 Baths ⋅ 10642565 MLS

Welcome to this charming brick-front ranch offering 3 bedrooms plus a spacious room over the garage that can serve as a fourth bedroom, home office, hobby room, or flexible living space. Situated on just under an acre, this property provides an expansive backyard with plenty of room to enjoy outdoor activities, gardening, or simply relaxing.Unwind on the inviting front porch or entertain on the large composite back deck overlooking the generous outdoor space. Inside, the open-concept kitchen and family room create a comfortable gathering area, while the formal living and dining rooms provide additional space for entertaining or everyday living. The attached garage is equipped with a mini-split system, offering year-round comfort and added versatility for a workshop, home gym, studio, or other uses. With its spacious layout, flexible living areas, and expansive lot, this home offers a wonderful blend of comfort, functionality, and outdoor enjoyment. 2024 Gutter shudder gutters, 2022 closed crawl dehumidification system/polly vapor barrier system. 2019 Trane a/c unit, upgraded w/trane clean air effects package w/reme halo bacteria eliminator & ac duct work. 2025 Landscape lighting.

940 Saddleback Trail, South Chesapeake

$630,000

4 Beds ⋅ 2.1 Baths ⋅ 10642546 MLS

Space, comfort, and quality updates come together in this 4-bedroom, 2.5-bath home in Upton Farms. A welcoming wraparound porch leads to an open floor plan with hardwood floors throughout the main living areas. The kitchen features granite countertops, stainless steel appliances, a large island, coffee bar area, bay window breakfast area, and backyard views from the sink. It opens to the spacious family room with a natural gas fireplace and abundant natural light. Upstairs offers a convenient laundry room and a beautifully renovated primary suite with marble tile, heated towel rack, and spa-inspired finishes. Enjoy outdoor living on the multi-level Trex deck with a pergola-covered saltwater hot tub, established herb and vegetable gardens, mature Japanese maples, and a rare Camellia. Come see why this home is one you’ll remember long after your visit.

923 Blackthorne Dr, South Chesapeake

$249,900

3 Beds ⋅ 1 Baths ⋅ 10642530 MLS

Beautifully maintained 3-bedroom, 1-bath brick home featuring refinished hardwood floors, fresh paint, and a new stove. Nestled among mature trees with a gorgeous lawn, this property also includes a detached garage and workshop, offering plenty of storage and workspace. Move-in ready and full of charm!

1003 White Pine Drive, South Chesapeake

$487,500

5 Beds ⋅ 2.1 Baths ⋅ 10642464 MLS

Lakefront 5 bedroom home in Grassfield High and Middle School District! Fully updated $60k of premium upgrades intended for a forever home! Quiet, sought-after neighborhood. Just minutes from shopping and interstate. Large property features a 30-yrnew architectural roof, all-new hardwood floors, and a new driveway. Interior boasts an office, formal dining, eat-in-kitchen with a new refrigerator, and a family room with a fireplace. Enjoy a Master bath upgrade ($30k) and pristine Trex deck in the large, fenced-in backyard.

517 Whisper Walk, South Chesapeake

$614,900

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

$619,900

4 Beds ⋅ 2.1 Baths ⋅ 10641071 MLS

Welcome home to this stunning like new construction in the highly sought-after Great Bridge School District! Move-in ready and thoughtfully designed, this beautiful home offers the freedom of no HOA and all the modern finishes today's buyers are looking for.Step inside to discover a bright, open-concept floor plan perfect for both everyday living and entertaining. The spacious first-floor office provides an ideal work-from-home space or flex room to fit your lifestyle. The gourmet kitchen is sure to impress with elegant quartz countertops, a classic subway tile backsplash, white shaker cabinetry, and a full stainless steel appliance package.Throughout the home, crown molding adds a touch of sophistication, while the energy-efficient tankless water heater provides modern convenience. Retreat outdoors to enjoy the fully fenced backyard, perfect for pets, play, or relaxing evenings. Make this home yours today.

1229 Waters Road, South Chesapeake

$570,000

5 Beds ⋅ 3 Baths ⋅ 10642122 MLS

Rare find in sought after neighborhood. Spacious and flexible floor plan features 5 bedrooms and 3 full baths, 4 closets in primary bedroom, huge family room and a flex room with fireplace that would be perfect for an office, library or study. Large back bedroom has its own entrance with easy, close access to full bath. Workshop has electricity. Well maintained by original owners. Make an appointment today to view this treasure and update to make it your own.

1213 Lakeford Place, South Chesapeake

$378,000

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

$640,000

4 Beds ⋅ 2.1 Baths ⋅ 10641989 MLS

Welcome to the popular Wells Model in Hickory Manor, offering 4 bedrooms, 2.5 baths, and a versatile upstairs loft. This home features exceptional storage throughout, including a double-door pantry, hall closet, under-stair storage, two upstairs linen closets, and dual closets in the spacious primary suite. The oversized 8-foot-long island has quartz countertops, perfect for entertaining and everyday living. 9-foot ceilings throughout bring in abundant natural light, with unobstructed southern and western exposures. Upstairs, the primary suite offers double closets, dual vanities, a soaking tub, and a separate shower. Three additional bedrooms, a full bath, and a conveniently located laundry room complete the second floor. Additional features include a 50-amp outlet in the garage, ideal for EV charging. Hickory Manor is conveniently located near Edinburgh shopping in top-rated Hickory school district and provides neighborhood pool, clubhouse, fitness center, park, and lawn maintenance.

445 Middleton Way, South Chesapeake

$589,000

5 Beds ⋅ 3 Baths ⋅ 10642362 MLS

Tired of expensive water and sewer bills, HOA restrictions, or dealing with the stress and cost of a fixer upper? Then this brand new home is exactly what you have been waiting for. Welcome to this stunning 2,600 sq. ft. open concept residence built by a local award winning builder. Featuring 5 spacious bedrooms, including a first floor bedroom great for guests or multi generational living, and 3 full baths with upscale designer finishes throughout. Enjoy luxury features including granite countertops, ceramic tile, luxury vinyl plank flooring, a cozy fireplace, and a beautiful standalone soaking tub. With NO HOA, this property is superb for boat owners, campers, trailers, or anyone wanting freedom and flexibility without extra fees or restrictions. Located in a highly sought school district with flexible spaces wonderful for entertaining and everyday living. Everything is brand new, offering peace of mind and low maintenance living.

789 Caddie Street, South Chesapeake

$619,900

4 Beds ⋅ 2.1 Baths ⋅ 10642204 MLS

Built in 2018 and showing like new, this stunning 4-bedroom home is a must-see! Situated on a beautiful lot backing to a wooded area, the backyard is an entertainer’s dream, featuring a paver patio and an in-ground salt water pool for relaxing or hosting family and friends.The chef’s kitchen opens seamlessly to the spacious family room, creating an ideal layout for everyday living and entertaining. Custom built-ins add both style and functionality, while the mudroom/drop zone provides convenient organization.Upstairs, the versatile loft offers endless possibilities as a sitting area, playroom, home office, or media space. Generously sized bedrooms provide comfort for everyone, and additional features include a whole-house backup generator and a 3-car garage.Meticulously maintained and reflecting true pride of ownership, this exceptional home is ready for its next owners to enjoy.

3637 Kathys Way, South Chesapeake

$995,000

4 Beds ⋅ 3.1 Baths ⋅ 10641759 MLS

Experience the a blend of luxury, space, and country charm in this stunning 2026 new construction home situated on a picturesque 3-acre lot where horses are welcome. Offering approximately 2,957 square feet of thoughtfully designed living space, this two-story home features 4 spacious bedrooms, 3.5 baths, and an open-concept floor plan great for both everyday living and entertaining. Step inside through the impressive entry foyer and discover 9-foot ceilings on both the first and second floors, smooth drywall finishes, craftsman trim, and quality finishes throughout. The heart of the home is the expansive kitchen featuring granite countertops, a large center island, walk-in pantry complete with cabinetry and countertop workspace, breakfast nook, and seamless flow into the spacious family room with an inviting electric fireplace. A dining room, private office, and convenient mudroom provide additional flexibility for today's lifestyle. The luxurious first-floor primary suite offers generous walk-in closets and a spa-inspired bath with a double vanity, tile flooring, tiled shower, and linen closet. Upstairs, you'll find three oversized bedrooms, each with walk-in closets. The front bedroom includes its own private bath, while the two rear bedrooms share a convenient Jack-and-Jill bath. A spacious loft/game room with durable LVP flooring creates a space for recreation, media, or a second living area. Built for comfort and efficiency, this home includes an elevated slab foundation, premium vinyl lap siding, architectural shingle roof, attached two-car garage, dual-zone HVAC systems, a high-efficiency 50-gallon heat pump water heater, conventional septic system, and pre-wiring for Ethernet and Wi-Fi. Relax on the front or rear concrete porches while enjoying peaceful country views, all while being just minutes from shopping, dining, and everyday conveniences. This exceptional property offers the best of both worlds—modern amenities, quality craftsmanship, and the freedom of country living on your own 3-acre retreat.

1630 Taft Road, South Chesapeake

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