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$575,000
5 Beds 2 Baths 10646017 MLS
FRESH EGGS, BIG FREEDOM, ENDLESS POTENTIAL in Chesapeake's desirable Blackwater area! Welcome to your private sanctuary—the ultimate lifestyle upgrade. Picture sipping morning coffee while collecting farm-fresh eggs from your backyard chickens, surrounded by peaceful green space. Enjoy pure, independent water from your premium 600+ ft Certified Artesian well, complete with a double tank water softener and an energy-efficient tankless electric water heater. Dream big with future-proof infrastructure: an oversized septic system is already in place to support an ADU, multi-generational living, or rental income. Built for comfort and efficiency, this ultimate hobbyist setup includes a premium dual-fuel HVAC and a sub-panel wired for a generator. Whether you envision a luxury guest cottage, a workshop, or an expanded country compound, the foundation is completely set. Schedule your tour today!

1336 Blackwater Road, South Chesapeake

$699,900
4 Beds 4 Baths 10645397 MLS
Welcome home to Rollingwood Estates in the highly sought after Great Bridge school district. This one owner brick transitional home offers 4 bedrooms and 4 full baths with an open, bright floor plan designed for comfortable living and effortless entertaining. The spacious FROG serves as the fourth bedroom and features its own private full bath, making it ideal for guests or multigenerational living. The kitchen offers Corian countertops, generous workspace and opens to the main living areas. Step outside to your own backyard retreat with a sparkling inground pool, dedicated pool bath, stamped concrete patio, outdoor bar/kitchen area, screened porch, and professionally landscaped yard. A two car attached garage, irrigation well, and thoughtful layout add to the appeal. Offering exceptional value in an established neighborhood, this home is priced to sell and ready for its next owner to make it their own.

837 Greenfield Lane, South Chesapeake

$899,900
4 Beds 3 Baths 10645653 MLS
Welcome to The Ashford by Wetherington Homes - MOVE IN BY AUGUST 2026! A 5-bedroom, 3-bath new construction home with over 2,700 sqft on approximately 2 acres in Hickory School District with NO HOA! Designed for todays buyer, this open-concept floorplan offers luxury finishes, designer details, outdoor entertaining, & flexible living spaces. The kitchen features quartz countertops, Frigidaire Professional appliances, custom wood hood, shaker cabinetry, & upgraded lighting. The 1st floor Primary Suite includes a tiled spa-style shower, dual vanities, & oversized walk-in closet. Two additional 1st floor bedrooms offer flexibility for guests or office space. Upstairs includes 2 bedrooms, full bath, & loft ideal for media room, playroom, or gym. Enjoy luxury new construction convenient to Edinburgh, Greenbrier, shopping, dining, & commuter routes while still offering privacy & acreage!

435 Gallbush Road, South Chesapeake

$629,000
6 Beds 3 Baths 10645483 MLS
Rare 6-bedroom opportunity with an ideal multigenerational layout! The first floor features a bedroom, adjacent flex room, and a modified curbless shower, offering exceptional flexibility and accessibility. Beautiful neutral decor, 9' ceilings, hardwood floors, elegant crown molding, and a huge FROG provide room for everyone. The spacious primary suite features hardwood floors and two walk-in closets. Convenient second-floor laundry. Enjoy a large fenced backyard with a powered detached shed and private well for economical lawn irrigation, plus an attached 2-car garage. Meticulously maintained with annual service contracts on the HVAC, tankless water heater, and crawl space. Seller will provide a termite/moisture letter. Convenient to Millville Rd., Veterans Bridge, Shipyard Rd., and major interstates, Portsmouth, Norfolk and Suffolk! Small community vibe with minimal traffic. minimal traffic.

1816 Sunsprite Loop, South Chesapeake

$575,000
4 Beds 2.1 Baths 10645016 MLS
Welcome to this beautifully maintained 4-bedroom, 2.5-bath home offering an open-concept floor plan designed for comfortable everyday living and effortless entertaining. Conveniently located near shopping, dining, and with easy interstate access, this home combines comfort with convenience. Relax and unwind on the spacious deck while enjoying peaceful views of the pond and the surrounding wildlife. The generous primary suite features a large walk-in closet, providing plenty of storage space. The well-appointed kitchen includes a gas range, a large pantry, and ample workspace for cooking and gathering. Located in the highly sought-after Chesapeake School District, this home also offers numerous valuable upgrades, including a new roof (2024), HVAC system (2024), and water heater (2021). Additional features include solar panels for energy efficiency, an irrigation system with a dedicated well, a security system, and the washer and dryer, all of which convey with the home.

1311 Piedmont Arch, 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

$689,000
5 Beds 2.1 Baths 10644518 MLS
Beautifully maintained 5-bedroom, 3,383-square-foot home offering peaceful golf course views in sought-after Wedgewood Estates. The thoughtfully designed floor plan features spacious living areas, an updated kitchen with a large center island, abundant cabinetry, and an open flow into the family room, creating a welcoming space for everyday living and entertaining. Large rear windows fill the home with natural light while overlooking the golf course and a beautiful wooded backdrop. Step outside to enjoy the screened porch and expansive patio, creating a private outdoor retreat. Thoughtfully maintained and exceptionally cared for, this home combines timeless character, quality updates, and outstanding curb appeal. Conveniently located in the heart of Greenbrier, just minutes from shopping, dining, parks, major highways, military installations, and healthcare, while offering the privacy and charm of one of Chesapeake's most desirable established neighborhoods.

1118 Fairway Drive, South Chesapeake

$599,000
5 Beds 3 Baths 10644309 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 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.

785 Caddie Street, 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

$685,000
5 Beds 3 Baths 10643877 MLS
A Gem! Pristine condition all brick transitional on 1/3 acre cul de sac lot in Great Bridge. 5 bedrooms plus 1st floor 6th bedroom or office with ensuite. Open floor plan with huge updated kitchen (quartz counters), breakfast room and family room overlooking impeccably landscaped and treed backyard. Remodeled primary & hall bathrooms. 2 zone HVAC. Wood burning fireplace also plumbed for gas. Spacious family room, living and dining rooms, bedrooms and FROG. Screened porch with concrete floor. 2 car side loading garage with long driveway. Updates include windows, roof, 1st floor gas pack HVAC, garage door and leaf filter gutters. Award winning Cheshire Forest community. Amenities include clubhouse, pool, tennis/pickleball court, parks and playground. In-ground sprinkler system, appliances, and window treatments convey "as is". Home warranty.

810 Hedgerow Court, South Chesapeake

$549,000
4 Beds 2.1 Baths 10642714 MLS
Impeccably maintained brick ranch with 4 bedrooms, 2.5 baths, an attached one-car garage, wood-burning fireplace and a spacious backyard. The remodeled kitchen features quartz countertops, soft-close cabinetry, stainless steel appliances, under-cabinet lighting, and a movable island. Updated bathrooms, custom wood trim, and closet organization systems add thoughtful touches throughout. Enjoy the 15x40 deck, fenced yard, storage shed, and newly expanded driveway with RV pad, 50-amp hookup, and generator connection. Major improvements over the years include windows, HVAC, 200-amp electrical panel, flooring, garage door, water heater, sprinkler/well system, and more. Convenient to bases, shopping & highways for easy access in Hampton Roads and to NC. Hickory HS district. This home has been diligently cared for inside and out and is truly move-in ready!

1025 Ramsgate Lane, South 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

$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

$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

$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

$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

$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

$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

$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

$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

$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

Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.