Chesapeake VA VA 3+ Acres Real Estate, Homes for Sale

Wonderful opportunity to get 4+ acres in high rated schools. HUGE outbuilding with 3 bays garage bays, powered, multi-level, for storage and recreational activities. Home sold as is. Part of an estate. Seller to do no repairs.

2323 Herring Ditch Road, South Chesapeake

$675,000

6 Beds ⋅ 2.1 Baths ⋅ 10645171 MLS

Rare opportunity to own over 6 private acres in the heart of Deep Creek! This exceptional property includes two parcels conveying with the sale, creating a combined 6+ acres of wooded privacy at the end of a quiet road. The spacious 6-bedroom home offers endless possibilities for multigenerational living, a home office, hobby space, or guest accommodations. Enjoy the peace and seclusion of country-style living while remaining just minutes from shopping, dining, schools, and major interstates. Come see this one first!

3249 Pioneer Lane, South Chesapeake

$765,000

5 Beds ⋅ 2.1 Baths ⋅ 10645076 MLS

Why wait on new construction when this one's already done? This home was taken all the way down to the foundation and completely rebuilt and expanded — outside of one corner of the home everything here is new. Home inspection is complete, every item addressed, so you can move in with genuine peace of mind. Tucked away on a quiet country road in Chesapeake and surrounded by 3 peaceful acres of mature trees, this modern farmhouse ranch offers the privacy and charm buyers dream about. Huge wraparound-feel porches front and back give you outdoor living space to spare, and the wide-open yard makes this property feel like a true retreat. Inside, gorgeous LVP flooring flows throughout, while the spacious living area with a stunning brick fireplace creates a warm gathering space. The farmhouse-inspired kitchen features white cabinetry, an oversized island with bar seating, and ample storage. Bedrooms are thoughtfully spaced for added privacy, while the hall bath offers a double vanity, step-in shower, and beautiful natural light. The primary suite feels like its own getaway, with private porch access, dual closets, and a spa-style bath featuring a floor-to-ceiling marble-tiled shower. A detached storage shed conveys, and the sprawling backyard offers endless possibilities — gardening, entertaining, or future additions. All the character of country living, with the peace of mind of a brand new home. Welcome home.

1629 Shillelagh Road, South Chesapeake

$1,195,000

4 Beds ⋅ 4.1 Baths ⋅ 10644941 MLS

Dreaming of a Serene Country Retreat just minutes from the city? YOU FOUND IT! A Rare Jewel! Horse Lover's Dream! Almost 9 ac Family Sanctuary. Elegant Custom Built, 4 Ensuite BRs & 1/2 Bath home w/an amazing 10' x 50' front porch! Lovely entry foyer opens to Great Room w/cathedral ceiling, hand scraped engineered flooring & wood burning fireplace framed w/bookshelf cabinetry. 1st Floor Primary BR boasts expansive Bath w/2 Separate Granite Vanities, jetted tub, separate shower & Grand Walk-In Closet. PBR Plantation Shutters reveal peaceful views of property! 10 ft ceilings down & 9 ft up. Kitchen w/granite counters, 2 large pantries, ample cabinetry & generous eat-in area. Formal Dining Room for festive gatherings. Upstairs reveals open sitting area w/chandelier. Expansive FROG-4th Bedroom. 3 Covered porches. 3 Car Garage, Spacious 2 Stall Stable, Large Storage Barn, approx 30' x 20' IG Pool w/stamped concrete surround. Fruit trees & acreage for hobby farming. Don't miss this one!

377 Homestead Road, West Chesapeake

$780,000

4 Beds ⋅ 2.2 Baths ⋅ 10644986 MLS

Welcome Home to this newly remodeled from top to bottom classic Home in Hickory's Pleasant Ridge neighborhood. Nestled back on this 3+ acre lot is this elegant and stylish two-story residence with new siding, windows, trim, fascia - the ultimate facelift. Enter into your foyer with new floors and fresh paint, new hardware, finishes, and lighting flow through this ideal layout. Formal living or dining off the left of foyer and to the right is large great room. Half bath for guests. Kitchen is spacious and feat. breakfast area and access to rear FROG stairs and garage. Second level feat. large primary suite with ensuite bath, two secondary bedrooms, hall bath, and FROG with half bath for convenience. Large newly installed deck leads to massive backyard waiting for you to put your stamp on. Call this Home Today!

705 Pleasant Ridge Court, South Chesapeake

$599,999

4 Beds ⋅ 2 Baths ⋅ 10644979 MLS

Welcome to this fully remodeled all-brick ranch located in the Hickory area of Chesapeake. Offering 4 bedrooms, 2 updated bathrooms, and situated on approximately 3 acres, this property provides generous indoor and outdoor living space. Interior updates include luxury vinyl plank flooring, tiled showers, granite countertops, stainless steel appliances, and an open, light-filled layout designed for everyday living and entertaining. Outdoor features include a covered front porch, an expansive rear deck, and a private deck accessible from the primary suite. Additional improvements include a newly poured driveway and a 50-AMP power pole ready for RV hookup. This move-in-ready home combines updated finishes with functional living space in a convenient Chesapeake location.

913 Long Ridge Road, South Chesapeake

$700,000

4 Beds ⋅ 2.1 Baths ⋅ 10644422 MLS

Welcome to peaceful country living without sacrificing convenience, this 4 bed 3 bath home is situated on 3 beautiful acres in the desirable Hickory area of Chesapeake. Enjoy the privacy and open space you’ve been looking for while remaining close to shopping, restaurants, and movies in the Edinburgh shopping area. Choose your own adventure, take route168 down to the Outer Banks in NC or go north to Virginia Beach. Get all of this with no HOA restrictions!!

1924 Land Of Promise Road, South Chesapeake

$820,000

5 Beds ⋅ 3 Baths ⋅ 10643909 MLS

Spacious 5 Bedroom, 3 Bath home on a beautiful 3-acre lot in the Grassfield High School district! On the main level you'll find LVP flooring, elevated lighting, updated Eat-in Kitchen w/huge island, stainless steel appliances including a Viking gas range, pantry and reverse osmosis drinking water, Family room with gas fireplace, Living and Dining Rooms and full bath. Primary Bedroom with walk-in closet and luxury ensuite bath, 4 secondary bedrooms, laundry (combo W/D unit) and full hall bath complete the 2nd floor. 2-car garage and abundant storage. Outside is made for fun and entertaining with an in-ground pool, stamped concrete patio, and an outdoor kitchen with grill, smoker, and pizza oven. A wonderful space to make memories with family and friends! Major updates include a brand-new dual-zone HVAC (2026), water heater (2025), water softener, garage doors and openers, repaved driveway, new soffits, fascia, gutters, window wrap, and front railing. No HOA! Enjoy the best of both worlds with a peaceful private setting while just minutes from shopping, restaurants, highways and everyday conveniences. Move-in ready!

1932 Foxwood Drive, South Chesapeake

$1,299,997

4 Beds ⋅ 2.1 Baths ⋅ 10644328 MLS

Custom 4,300+ sq ft estate on 3 private, wooded acres on historic Taft Rd., located in the Hickory/Grassfield school districts. Perfect blend of country living & city access. Inside features exceptional build quality, ornate plasterwork, dentil moulding, & dual staircases. The main level hosts a home office, living room with a wood fireplace, half bath, & a sunroom. The spacious kitchen boasts a center island & matte white cafe; appliances, leading to a laundry room & 2-car heated garage. Upstairs features 4 large bedrooms, including a primary suite with 2 walk-in closets & 3rd-floor access. 2 full baths feature luxury defogging mirrors. The 3rd floor is ideal for a 2nd living room/studio. Outside boasts a wrap-around porch, 32k-gal saltwater pool (new liner 2025; new pump/filter/salt cell 2026), Trex deck, heated 3-car detached garage with mini-split, carport, shed (new roof 2026), & pole barn. Features 400A service (200A panel), generator tie, & grill propane line. Move-in ready!

1741 Taft Road, South Chesapeake

$440,000

3 Beds ⋅ 1.1 Baths ⋅ 10644034 MLS

Escape to serene equestrian country living! This inviting 3-bedroom, 1.5-bath ranch (with additional non-heated/cooled bedroom/flex room over garage and additional full bath) sits on over 3 acres in Chesapeake's desirable Western Branch area, offering the perfect blend of privacy, open space, and modern updates. Inside, you'll find a move-in-ready home featuring a bright, updated kitchen, durable LVP flooring, spacious bedrooms, and the convenience of single-level living. The room over the attached garage provides flexible space for a home office, guest suite, 4th bedroom, or in-law suite. Outside, the 3-stall horse barn needs TLC, plus plenty of room for gardening, recreation, or creating your own mini homestead. Recent improvements include land improvements (2019), well service (2020), electrical panel service (2020), foundation improvements (2021), new appliances (2022). Tenant occupied at $2,800 per month thru 1/31/27. Live in or rent out.

4309 East Road, West Chesapeake

$988,613

4 Beds ⋅ 3.1 Baths ⋅ 10643550 MLS

CURRENTLY IN FOUNDATION! STILL TIME TO PERSONALIZE THE FINISHES IN YOUR DREAM HOME! Meet the Holden by Kirbor Homes! A home that checks all the boxes and then a few you didn't even know you wanted! From the moment you step inside, you'll love the bright, open layout that's designed for everything from holiday gatherings to cozy movie nights. The chef-inspired kitchen is the true heart of the home, featuring a spacious island where everyone naturally gather, plenty of cabinet space, and an easy flow into the dining area and Great Room. Whether you're hosting friends or enjoying a quiet morning with coffee, this home is designed to make every day feel a little more special. When it's time to unwind, head on over to the first-floor primary suite, complete with a spa-like bath and generous walk-in closet. Need a home office, playroom, or hobby space? You've got that, too! Upstairs, you'll find spacious secondary bedrooms and a versatile loft that's ready to become your game room, media room, fitness space, or whatever best fits your lifestyle. If you've been searching for a home that's equal parts stylish, functional, and welcoming, you've just found it. Come see why the Holden feels like home the moment you walk through the door. Builder contract required. Reach out today to schedule an appointment at our Design Center and experience the beautiful finishes and thoughtful selections that have been chosen for this home. Ask about current builder incentives and available opportunities to make this dream home yours!

2116 Sanderson Road, South Chesapeake

$997,724

5 Beds ⋅ 4.1 Baths ⋅ 10643679 MLS

Some homes simply check the boxes. The Miles by Kirbor Homes is designed to exceed expectations. Thoughtfully crafted for the way you live today, this home combines stylish finishes, functional spaces, and everyday comfort in all the right places. The heart of the home is the beautifully designed kitchen, where morning coffee turns into family dinners, holiday traditions, and conversations that linger long after the meal is over. Featuring our upgraded Chef's Appliance Package, a spacious center island, abundant cabinetry, and an open flow into the dining area and Great Room, this space was made for gathering, whether you're entertaining a crowd or enjoying a quiet night at home. When it's time to unwind, head to the spacious primary suite featuring a walk-in closet that's practically the size of a bedroom and a spa-inspired bath that makes every day feel a little more like a vacation. Additional bedrooms and versatile living spaces provide endless opportunities for a home office, playroom, fitness room, media lounge, or whatever your lifestyle calls for next. Step outside to the covered rear porch and imagine weekend cookouts, evenings under the stars, or slow Sunday afternoons where the only thing on your schedule is deciding whether to refill your coffee or fire up the grill. Built with the exceptional craftsmanship and attention to detail Kirbor Homes is known for, the Miles offers the perfect blend of style, flexibility, and livability. This isn't just another floor plan: it's the one you'll find yourself measuring every other home against. Schedule an appointment at our design center today and discover why the Miles just feels like home. Builder contract required. Ask about available lender incentives!

1533 Sanderson Road, South Chesapeake

$875,000

4 Beds ⋅ 3.1 Baths ⋅ 10643488 MLS

Set on just over three private wooded acres in sought after Shillelagh Farms and located in the Grassfield School District, this custom-built home offers a rare combination of privacy, space, and freedom with no HOA restrictions. A dramatic two story foyer, soaring vaulted ceilings, and front and rear staircases add character and functionality while the inviting floor plan is designed for both everyday living and entertaining. Featuring four bedrooms, 3.5 baths, a dedicated office, spacious FROG with full bath, and a primary suite with oversized walk-in closet. Enjoy the expansive multi-level deck overlooking the private wooded backyard. The detached 1,092 square foot garage/workshop with full attic storage offers endless possibilities for car enthusiasts, crafts people, or those needing exceptional storage and workspace for RVs, boats, and recreational vehicles. Rarely does a property offer this combination of acreage, privacy, detached workshop, no HOA and prime Grassfield location.

2025 Hallmark Way, South Chesapeake

$700,000

4 Beds ⋅ 3 Baths ⋅ 10643450 MLS

Welcome to this beautiful 4-bedroom, 3-bath home nestled on just over 3 acres in the highly sought-after Grassfield area of Chesapeake. Tucked away in a community with no HOA, this property offers the perfect blend of privacy and convenience. Relax on the spacious front porch. Inside, find soaring ceilings that create an open, airy feel in the living room. The home features a water filtration system, a beautifully renovated primary bath, and a huge flex room over the garage ideal for a media room, home office, gym, or guest space. Out back, enjoy your own private retreat with a patio and swimming pool, perfect for entertaining or unwinding after a long day. With generous indoor and outdoor living spaces, this property offers the lifestyle you've been looking for in one of Chesapeake's most desirable locations.

1116 Tundrah Court, 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

$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

$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

$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

$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

$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

$549,500

3 Beds ⋅ 2 Baths ⋅ 10642197 MLS

Calling all homesteaders! Looking for space to work, build, or spread out in the Grassfield school district? This 5-acre Chesapeake property is built for it. The 720 sq. ft. detached garage runs on full electric — great for a contractor, tradesman, hobbyist, or anyone needing a real workshop, equipment storage, or room for the toys. Easy road frontage means simple access for trucks, trailers, and equipment. The move-in-ready 3-bed, 2-bath home means no work waiting on you: 2023 heat pump, 2024 whole-house professional paint, and new 2025 carpet. Inside you'll find an open kitchen with wood cabinets and breakfast nook, a spacious sunroom, and a large mudroom. Outside: fenced backyard, mature fruit and fig trees, and wildlife right off the Dismal Swamp Canal Trail. minutes from Deep Creek Park. Rare acreage, real workspace, and a home that's ready now. Seller facing unexpected military move. Highly motivated seller. Recently sold comparable properties have sold for $645k. Contact an agent today for a private showig!

317 George Washington Highway S, South Chesapeake

$834,900

4 Beds ⋅ 2.1 Baths ⋅ 10641919 MLS

Your Chesapeake dream home awaits! With over 7 acres of privacy and woods, you're going to love the peaceful seclusion your new home brings. We are a truly custom builder and can build any home here you'd like. Shown is our popular Aspen model: with 2400 square feet, a gorgeous open floor plan and a common sense layout this home checks all the boxes. We're unlike any other builder you've experienced! Call now to learn more!

7 AC Shillelagh Road, South Chesapeake

$650,000

4 Beds ⋅ 2 Baths ⋅ 10641777 MLS

Welcome home to this charming 4-bedroom, 2-bath brick ranch nestled on 4.22 wooded acres at the end of a quiet cul-de-sac. Inside, you'll find a warm and inviting layout featuring a family room with a wood-burning fireplace, formal living and dining rooms, granite countertops, and beautifully updated primary and hall bathrooms. Step outside to relax on the new composite deck (2024), gather around the fire pit, or enjoy the peaceful wooded surroundings. The property also includes a detached 2-car garage with a finished studio apartment and full bath, plus a whole-house generator and water softener for added convenience. Offering space, privacy, and versatile living, this property is ready to welcome you home! You won't want to miss this one!

1345 Oak Ridge Drive, South Chesapeake

$750,000

4 Beds ⋅ 3 Baths ⋅ 10641597 MLS

Welcome to 1028 Pleasant Ridge Drive, where space, privacy, and comfort come together on a beautifully wooded three-acre homesite. From the moment you arrive, the setting is peaceful and private with natural light filling spacious living areas. The layout is ideal for both everyday living and entertaining, with generous gathering areas and well-sized bedrooms. This custom ranch-style residence offers approximately 3,700 square feet of thoughtfully designed living space, featuring four bedrooms, three full baths, and flexible areas suited for a growing family and today’s lifestyle. The first-floor primary suite provides a relaxing escape with a large walk-in closet and an ensuite bath featuring a beautiful tiled shower, separate tub and large vanity. This home opens to serene outdoor views of your private backyard retreat, complete with an in-ground saltwater pool, mature trees, and room to enjoy the peaceful setting that makes this one of Chesapeake’s most sought-after addresses. Whether you’re looking for space for family, hobbies, recreational vehicles, or simply a quieter way of life, this property delivers the rare combination of acreage, convenience, and versatility. Located within the highly regarded Hickory area, residents enjoy a rural atmosphere while remaining minutes to shopping and major highways. Also conveniently located to beaches, amazing restaurants and military bases with No HOA making this property truly the perfect blend of tranquility and accessibility.

1028 Pleasant Ridge Drive, South Chesapeake

$1,175,000

5 Beds ⋅ 4 Baths ⋅ 10641376 MLS

Welcome to this exceptional 5-bedroom, 4-bath custom home in the sought-after Hickory Station community in the sought-after Hickory School District! Situated on over 3 acres with beautiful wooded views, this stunning property offers the perfect blend of luxury, space, and modern updates. Boasting more than 4,200 square feet of living space, this home features a beautifully renovated kitchen, a spacious primary suite with a newly renovated bath, and an updated guest bathroom. Fresh paint throughout, new LED lighting, refinished hardwood floors, new windows, and new garage doors add style and efficiency throughout the home. Designed for both everyday living and entertaining, you'll love the expansive media room, generous living spaces, and seamless indoor outdoor flow. Step outside to your private backyard retreat featuring a beautiful 20' x 40' inground pool. A detached two-car garage provides additional storage and flexibility. Other recent improvements include a new roof, new second-floor HVAC system, Kinetico water treatment system for added peace of mind. This rare Hickory Station gem offers privacy, acreage, exceptional updates, and access to one of Chesapeake's most desired school districts. Don't miss the opportunity to make this remarkable property your next home.

2104 Hickory Forest Dr, South Chesapeake

$774,900

4 Beds ⋅ 3.1 Baths ⋅ 10641375 MLS

Set on over 3 acres and tucked back from the road, this meticulously updated 4-bedroom, 3.5-bath Chesapeake property offers a rare blend of space, privacy, and modern finishes. Renovated with care and attention to detail, updates include a new roof, all-new kitchen cabinetry, upgraded stainless steel appliances, quartz countertops, engineered hardwood flooring, fresh paint, and beautifully redesigned bathrooms with custom tile. The spacious first-floor primary suite adds convenience, while a second en suite offers flexibility. Enjoy a welcoming front porch and a new back patio overlooking a partially-fenced yard backing to wooded views. Ample closet space and storage throughout, plus a 2-car attached garage. Move-in ready with a unique combination of land and updates.

1124 Saint Brides Road W, South Chesapeake

$1,999,000

10640859 MLS

Gorgeous cleared country acreage in the Hickory High School district, just appx 2.4mi from the high school, 4mi from Edinburgh, 7 mi from the VA/NC line and 7.8mi from City Hall. Some ditching in place for drainage. No access without permission from the Listing Agent, as property is currently being used as farm land.

145A Beaver Dam Road, South Chesapeake

$425,000

10640862 MLS

Gorgeous 20+ acre site in the Hickory High School district. Just app 2.4mi from the high school, 4mi from Edinburgh, 7mi from the VA/NC line and 7.8mi from City Hall. Land is cleared with some ditching in place. No access without permission from Listing Agent.

20A Head Of River Road, South Chesapeake

$240,000

10640857 MLS

Gorgeous 3 Acre site in the Hickory High School District. Just 2.4mi from the high school, and approx 4mi from Edinburgh, approx 7mi from the Virginia/NC line, and 7.8mi from City Hall. Land is cleared, currently used for crops, with some ditching in place for drainage. No access without permission from Listing Agent.

1213 Head Of River Road, South Chesapeake

$290,000

10640910 MLS

Rare opportunity to own approximately 7.4 acres in the desirable Hickory area! This city-approved homesite has already been cleared and is ready for your dream home. Extensive due diligence and site preparation have been completed, including a boundary survey, successful perc test, engineered septic system design, wetlands mitigation, and full compliance with U.S. Army Corps of Engineers requirements. Save valuable time and expense with approvals already in place, and enjoy the flexibility of bringing the builder of your choice. Offering privacy, space, and a prime location, this exceptional parcel is ready for your vision to become reality.

1813 Shillelagh Road, South Chesapeake

$799,900

4 Beds ⋅ 2.1 Baths ⋅ 10640783 MLS

The Aspen Barndominium! Customize this 4b/ 2.5b barndo with your style, colors and finishes with the builder. Stunning Covered Front Porch leads to the Open Great Room designed with 18ft vaulted ceiling for the perfect open Living, Dining and Kitchen space. Kitchen with Stainless Steel Appliances, granite counters, tile backsplash, and walk-in pantry. Large Primary with huge walk-in closet and Spa-like Bathroom. Large laundry room, mudroom with lots of storage space and wash area. Bedrooms 2, 3, 4 share a bathroom with rec/bonus space. Best spot may just be the huge covered back porch with lovely nature views and access from the kitchen great room. Pics of previously built Aspen and may show upgrades. Listing price includes Turn-Key Cost to build with a Construction Loan including cost of Land, Well, Septic, and Land Development.

2907 Seven Eleven Road, South Chesapeake

$939,900

4 Beds ⋅ 3.1 Baths ⋅ 10640467 MLS

1421 Saint Brides Rd West, the ASHBEE Model by Wetherington Homes. Ready Now. Situated on a wooded and private 16+ acre parcel in Southern Chesapeake, this spacious and open concept floorplan offers 4 bedrooms PLUS AN OFFICE AND A LOFT! Great Room opens to Kitchen with center island with overhang for extra seating, dining area, quartz counters, tile backsplash, pantry, and stainless appliances. First Floor Owner's Suite features extra large walk in closet with wood shelving and full bath with tile surround step in shower, soaking tub, tile flooring, vanity with double bowls and quartz counters, and water closet. You will love the Covered Porch to enjoy the peaceful wooded setting! Add'l Details: LVP flooring on 1st floor; wood treads on stairs; carpeting in all bedrooms; quartz counters in full baths; 1st floor Laundry Room; Mud Room with drop zone; craftsman style doors & trim; stylish finishes; Front Porch; 2 car garage; and more!

1421 Saint Brides Road West, South Chesapeake

$250,000

10640341 MLS

Incredible value on this 4.75 acre lot. Don't miss this opportunity to own a piece of country living. This property is not in a flood zone.

1836 Mount Pleasant Road, South Chesapeake

$750,000

3 Beds ⋅ 3 Baths ⋅ 10639959 MLS

Updated farmhouse charm on nearly 4 acres! This traditional home offers 3 bedrooms, 3 full baths, and a spacious finished room over the garage. Outside, enjoy designated pastures, a barn, and a detached two-car garage with a framed upper level ready for future expansion or flexible use. A unique property with room to enjoy the outdoors and endless possibilities. Back on Market due to no fault of the seller. We have a clear termite & mositure letter, home inspection, recent septic inspection and pump 4/2026 and ready for a quick close.

3536 Riverwood Crescent, South Chesapeake

$860,500

4 Beds ⋅ 3 Baths ⋅ 10639826 MLS

Custom throughout and thoughtfully designed with an open floor plan, this exceptional home offers luxury living on a private 3-acre cul-de-sac lot in the sought-after Hickory High School district. The custom kitchen is loaded with upgrades and opens beautifully to the main living areas featuring hardwood floors, granite countertops, and beautifully tiled baths throughout. The fantastic primary suite offers a true retreat with a huge spa-like primary bathroom. Enjoy breathtaking sunset views from the screened-in porch overlooking the expansive backyard great for kids, pets, entertaining, or simply enjoying the peaceful setting. Part of the backyard is fully fenced and enclosed for added convenience. Additional highlights include a whole-house generator and an oversized detached 3-car garage with a large finished room above offering endless possibilities for a home office, gym, guest suite, hobby space, or recreation room.

2312 Dapple Grey Court, South Chesapeake

$1,325,000

5 Beds ⋅ 3.1 Baths ⋅ 10639607 MLS

Rarely does a property offer this much space, flexibility and freedom. Situated on over 28 private acres in Chesapeake's desirable Hickory area, this one-of-a-kind property offers 3,677 square feet, 5 bedrooms and 3.5 baths. Inside, you'll find abundant natural light, spacious living areas, an open-concept layout, and warm, inviting finishes throughout. A rare feature, the home includes two primary suites, one on the main level and one upstairs, each with its own private ensuite bath, appealing for multigenerational living, extended guests, or added privacy. Outside, enjoy a wraparound-style porch extending along the front and sides of the home, an expansive composite deck, detached 4-car garage, professionally equipped workshop, private shooting and archery areas, fruit trees, grape vines, and endless opportunities for hunting, recreation, and outdoor living. Be sure to review the attached feature and upgrade sheet for additional highlights and improvements!

509 Ballahack Road, South Chesapeake

$450,000

10639627 MLS

Well-established, highly profitable Mediterranean restaurant generating $700K+ in annual gross sales with strong, consistent cash flow. This is a turnkey operation situated in a prime, high-traffic location with a deeply loyal local customer base. The favorable lease is secured through 2030 at $3,900/month. Multiple flexible purchasing options are available to fit your investment goals: Purchase the established brick-and-mortar Restaurant Business alone for $300,000. Acquire the complete mobile expansion assets, including a brand-new, fully branded food trailer and dedicated Ford tow vehicle, for an additional $150,000. Purchase the entire comprehensive package (Restaurant + Trailer + Tow Vehicle) for $450,000. This is an incredible turnkey opportunity perfectly suited for an owner-operator or an investor looking to immediately capitalize on established dine-in, catering, and lucrative mobile/festival revenue streams. Complete financial records (POS data and tax returns) and an equipment inventory list are available upon request with a signed NDA. Seller is relocating. Please do not disturb employees or discuss the sale on-site. All showings are strictly by appointment only. Serious, qualified buyers only.

1437 Sam's Drive, South Chesapeake

$749,000

4 Beds ⋅ 2.1 Baths ⋅ 10639261 MLS

Privately located on 3.065 treed lot. Enjoy peace and tranquility at the end of a day. Home is approximately 3203 sq ft with 4 bedrooms, 2.5 baths. Great Rm + Sunroom. Oversized primary bedroom + 2 car garage attached. Property has a detached building (approx. 1440 sq ft) used as a gym. 3 bay garage with 14ft, 11 ft and 10' doors to accommodate large vehicles. This building includes a 2nd floor approximately 1K sq ft apartment with kitchen, full bath, with newer wall to wall carpet. Apartment could be used for guests or to operate a home business. Main architectural grade roof is approximately 15 yrs old. Hot water heater '23. 1st floor HVAC '25. Septic tank pumped 8 mos. ago. Property sold in as is condition. No flood insurance required.

353 Sign Pine Road, South Chesapeake

$699,000

6 Beds ⋅ 4.1 Baths ⋅ 10638550 MLS

Lovely all brick home situated on a private 3-acre lot in Timberwood. Home offers 6 bedrooms + FROG and 4.5 bathrooms. Welcoming entry opens to a formal living room with lots of windows and abundant natural sunlight + a formal dining room with bar, hardwood floors. Large open great room with kitchen + pantry, living room with gas fireplace, breakfast area, cathedral ceilings, lots of natural light. Spacious 1st floor primary suite with sitting area, walk in closets, dual sinks, garden tub, shower, and toilet closet (shower remodel is unfinished - may require repair escrow for financing). 3-car attached garage + detached shed/workshop. Fresh paint; some new plumbing & electrical fixtures.

3815 Cypress Mill Road, South Chesapeake

$1,175,000

4 Beds ⋅ 2.1 Baths ⋅ 10638388 MLS

Welcome to 2333 Land of Promise Road — an extraordinary custom estate tucked behind a solar-powered gated entrance in the heart of Hickory, Chesapeake. Set on 6.21 fully fenced, private acres lined with mature Leyland Cypress trees, this property delivers luxury living, ultimate privacy, and unmatched industrial-grade functionality. Built in 2018, this modern farmhouse spans ~3,080 sq ft of open-concept living with a soaring two-story living room featuring a dramatic shiplap fireplace and oversized windows. The chef's kitchen boasts top-of-the-line GE appliances, custom solid wood cabinetry with soft-close dovetail joints, an oversized island, crown molding, and a copper farmhouse sink, while the main-floor primary suite offers double tray ceilings and a spa-inspired bathroom. Smart home features include a whole-house propane generator, Kinetico reverse osmosis water filtration, whole-home surround sound, surge protection, and a French drain system. Outside, enjoy a heated saltwater fiberglass pool with built-in seating, a pool pavilion, an insulated she-shed with wood-burning stove, fruit/nut orchards, and a recreational shooting range. The outbuildings are truly unmatched: a 4,800 sq ft workshop with three-phase power (480V), private office, bathroom, and separate well/septic; an attached 1,200 sq ft lean-to with 50-amp RV hookups; and three converted silos totaling 6,500+ sq ft of powered space — currently a yoga studio, woodworking shop, and storage facility. Whether your vision is a private compound, luxury hobby farm, business headquarters, or automotive haven, this estate offers a lifestyle that cannot be replicated.

2333 Land Of Promise Road, South Chesapeake

$1,695,000

5 Beds ⋅ 3.2 Baths ⋅ 10637839 MLS

Set within the sought-after Woodards Mill “loop,” this beautiful landscaped property blends impressive living with peaceful privacy just minutes from everyday conveniences. Originally built in 1984 and fully reimagined beginning in 2001 by professional contractors, the home has been thoughtfully expanded to over 6,000 square feet of refined, comfortable living space. Every addition and update was meticulously planned and expertly executed. The heart of the home features an expansive family and entertainment room overlooking a spacious blue stone lanai. A stunning all brick sunroom adds warmth while the main level offers a generous primary suite along with three additional bedrooms (one used as home office.) Upstairs, a private second primary suite provides an ideal retreat for guests or multi generational living. Outdoor enjoy a true gardeners paradise with mature hydrangeas, peonies, irises and much more. The fenced saltwater pool with new liner offers both relaxation and peace of mind. Life on the loop brings a unique sense of community, known for its annual parades from Jingle Bell and Horse Parade to July 4th to the famous Halloween Parade. As an added everyday convenience enjoy school bus pick up and drop at the home. This home is not like any others sold in this neighborhood, a must see.

517 Woodards Ford Road, South Chesapeake

$750,000

10637870 MLS

A 28-acre property is located in the Grassfield/Hickory region of Chesapeake. Whether you intend to build your dream home or utilize it for investment purposes, the property offers limitless potential. The property is sold “as is,” “where is,” and the buyer bears the responsibility of conducting their due diligence.

28 Johnstown Crescent, South Chesapeake

$1,274,900

4 Beds ⋅ 4 Baths ⋅ 10637217 MLS

MOTIVATED SELLER!!! Welcome to 709 Forest Mills Road, a stunning private estate nestled on approximately three acres in Chesapeake's highly sought-after Hickory community. This exceptional custom-built residence offers over 5,300 square feet of thoughtfully designed living space, blending timeless elegance with everyday comfort. Featuring four spacious bedrooms and four full bathrooms, the home boasts generous living and entertaining areas, soaring ceilings, abundant natural light, and quality craftsmanship throughout. The expansive floor plan provides flexibility for both formal gatherings and relaxed family living. Outside, the beautifully maintained acreage offers a rare combination of privacy and open space, creating the perfect setting for outdoor entertaining, recreation, gardening, or simply enjoying peaceful country living. Mature landscaping and a picturesque setting enhance the property's impressive curb appeal. Located within the award-winning Hickory school district and just minutes from shopping, dining, and major commuter routes, this remarkable property delivers the ideal balance of luxury, convenience, and tranquility. Experience the space, privacy, and lifestyle that make 709 Forest Mills Road a truly exceptional place to call home.

709 Forest Mills Road, South Chesapeake

$240,000

10636984 MLS

Western Branch school zoned 6 acre parcel ready for you to build your dream home. NO Hoa fees or rules. Seller will provide survey just recently done and a copy of perk test for approved offers only. Non conforming septic systems can be used, and you will need to dig a private deep water well. Listing agent can provide some options for septic and local well companies, along with local builders and land lenders. Enjoy the privacy of "country style" living while being minutes from interstate access. Centrally located between Va Beach and Suffolk. This land was just appraised in January of 2026.

4809 Sondej Avenue, West Chesapeake

$1,650,000

4 Beds ⋅ 3.1 Baths ⋅ 10636693 MLS

Welcome to your dream escape — a stunning, brand new 2025 modern farmhouse nestled on 25.9 breathtaking acres in the heart of Hickory! From the moment you arrive, this 3,876 sq ft masterpiece captivates with its crisp white exterior, soaring cathedral ceilings, and gorgeous open-concept layout designed for both everyday living and unforgettable entertaining. The chef's kitchen is an absolute showstopper, featuring white cabinetry, a hooded range, and charming farmhouse finishes that perfectly blend style with function. Light brown LVP flows throughout the main level, adding warmth and elegance to every room. The oversized 3+ car garage is equipped with an EV charging station and a fully finished room above with a full bath — great for guests, a home office, or a private retreat. Step outside to your own private oasis where a sparkling saltwater heated pool and expansive deck await, with endless possibilities to add an outdoor kitchen, bar, and lounge. Horse lovers and hobby farmers, this one's for you — horses are welcome and the land is ready to bring your vision to life, with soybean fields already in place. A geo-thermal HVAC system, water softener, rainwater harvesting, and well water make this estate as efficient as it is beautiful. This is more than a home — it's a lifestyle. Don't miss your chance to own this rare, one-of-a-kind property!

1200 Beaver Dam Road, South Chesapeake

$387,000

3 Beds ⋅ 1 Baths ⋅ 10635736 MLS

Welcome to peaceful country living at its finest! Nestled on approximately 5 acres of cleared land, this charming ranch-style property offers the perfect blend of privacy, functionality, and opportunity. Great for horse lovers, hobby farmers, contractors, or anyone seeking room to spread out, the property features horse stalls, multiple outbuildings, and wide-open usable acreage ready for animals, equipment, recreation, or future expansion. The spacious ranch home provides comfortable single-level living with a relaxed rural atmosphere while still offering convenient access to Chesapeake amenities. Whether you envision a mini farm, equestrian retreat, workshop space, or simply enjoying sunsets over your own acreage, this versatile property delivers endless possibilities. Selling AS IS.

4649 Backwoods Road, South Chesapeake

$955,000

5 Beds ⋅ 4.1 Baths ⋅ 10636102 MLS

Nestled on a 3.44 acre wooded lot, this full brick home features beautiful craftsmanship, traditional floor plan with a resort style backyard. The main level offers an inviting family room with cozy fireplace, Dining room with designer wallpaper, crown and chair rail moldings, and a flexible study/ or 5th bedroom located near a full bath with walk-in shower. The eat-in kitchen has solid wood, dovetail cabinetry, backsplash and wine refrigerator. Fresh paint throughout, some new flooring, updated light fixtures. Second level has an oversized Primary Bedroom large enough for a sitting area with great en suite, Two additional guest bedrooms that have direct access to a spacious lounge/bonus room. FROG is oversized with a full bathroom, great for an in-law suite! The expansive sunroom overlooks the beautiful backyard complete with in ground pool, pool house, and covered deck great for entertaining. Move-in ready, a must see!

2408 Johnstown Road, South Chesapeake

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