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$545,000
3 Beds 2.1 Baths 10649408 MLS
Welcome to this beautifully appointed 3-BR, 2.5-bath home located in a highly sought-after community w/ desirable schools, convenient shopping, & an exceptional lifestyle.The Lg primary suite features a spa-inspired bath w/lg soaking tub, walk-in shower, & linen closet. XXL walk-in closet is complete w/ built-in shelving for effortless organization. Designed for both everyday living & entertaining, the open floor plan showcases a chef-style kitchen w/ an abundance of cabinetry, a beautiful new backsplash, pantry& an island/bar with seating. Kitchen flows seamlessly into family rm & dining area, creating a warm & inviting gathering space. Step outside to one of the largest backyard areas available for this model, offering a peaceful & private setting that backs to a picturesque pond complete w/ fountain & walking path. It’s the perfect spot to relax, entertain, or simply enjoy the beautiful surroundings. Enjoy resort-style amenities w/o the maintenance - your HOA takes care of the front yard and flowerbeds, while residents take advantage of the beautiful club house, community pool, and extensive exercise room. $5000 carpet allowance. You decide carpet or other! Call to schedule an appointment

316 Middleton Way, South Chesapeake

$464,900
3 Beds 2.1 Baths 10648866 MLS
Experience low-maintenance living at its finest in this beautifully appointed home in the heart of Chesapeake. Built in 2019, this 3-bed, 2.5-bath residence offers a modern, open-concept design w/stylish finishes and thoughtful details throughout. The spacious main living area flows seamlessly into a well-designed kitchen. A first-floor primary suite provides comfort and convenience, while additional bedrooms offer flexibility for guests, a home office, or hobbies. Enjoy the ease of a low-maintenance lifestyle with community amenities that elevate everyday living, all in a sought-after location near shopping, dining, and top conveniences. This is the perfect blend of comfort, style, and simplicity, great for those ready to enjoy more and maintain less.

419 Heartfield Drive, South Chesapeake

$789,900
5 Beds 3 Baths 10648928 MLS
NEW PRICE—NOW $789,900! $25K+ REDUCTION. Located in a welcoming, highly desirable community with NO HOA, this meticulously maintained home offers the feel of new construction with over $75,000 in thoughtful upgrades. The customized gourmet kitchen features double ovens, a built-in microwave drawer, designer finishes, and a dry bar with beverage refrigerator—great for gathering and entertaining. Custom window treatments, upgraded lighting, smart-home features, a reverse-osmosis water system, and more elevate everyday living. A first-floor bedroom and full bath offer flexibility. Relax on the inviting front porch, enjoy the screened-in porch, expansive patio, fully fenced yard, and peaceful wooded backdrop. Close to shopping, dining, and everyday conveniences, this truly move-in-ready home delivers the best of both worlds: a strong sense of community with privacy in your own backyard. Luxury country living at its finest!

633 Ambrose Street, South Chesapeake

$799,000
4 Beds 3 Baths 10648602 MLS
Pristinely kept home on over 3 Acres located in the highly sought-after Hickory School District! This move-in-ready home has been meticulously cared for with major system upgrades including a 3- year old roof, all new siding, a rebuilt HVAC package unit with all new components, two water heaters, a whole-house generator and updated windows and gutters! The renovated kitchen (2017), main room refinished hardwood and recently updated Primary bedroom set this home apart! Enjoy outdoor living on the Trex decking and rest easy knowing the septic system was cleaned and pumped in January 2026. With extensive updates, exceptional maintenance, and a prime location in the Hickory area of Chesapeake, this home offers the perfect combination of comfort, efficiency, and long-term value with land to go with it! Come see your new home today!

2020 Sanderson Road, South Chesapeake

$1,199,000
5 Beds 3.1 Baths 10648292 MLS
Welcome home!! 28.18 private acres, 3,714 sq ft, 5 bedrooms, 3.5 updated baths, TWO primary suites, a detached 4-car garage and 20x30 workshop—all in Chesapeake’s sought-after Hickory area?! Yes! Here at 509 Ballahack Rd. Extensively improved inside and out, this one-of-a-kind property delivers the space, flexibility and freedom of country living with modern comfort. Abundant natural light fills the spacious living areas, while warm finishes and thoughtful updates create an inviting feel throughout. The kitchen is complemented by a butler pantry with granite countertop, cabinetry and additional storage, adding function for everyday living and entertaining. The rare dual-primary layout offers one suite on each level, both with private ensuite baths—ideal for multigenerational living, extended guests or added privacy. The main-level primary has been refreshed with new flooring, paint, lighting and hardware. Upstairs, the second primary features a showstopping spa-inspired ensuite with an oversized wet room, rainfall shower, body jets, two-person soaking tub, porcelain tile and polished marble mosaic. All 3.5 bathrooms have been updated with fresh flooring, lighting, paint, mirrors and hardware. Outside, enjoy a nearly wraparound front porch, expansive 20x40 composite deck, outdoor kitchen setup, custom fire pit, fruit trees, grape vines and 28+ acres to explore. Proven deer and turkey hunting is literally steps from your back door, with private shooting and archery areas already in place. The detached 4-car garage provides exceptional storage, while the 20x30 workshop features concrete flooring, lighting and its own electrical panel. Additional improvements include 33 solar panels (to be paid off with acceptable offer), Level 2 EV charger, major electrical upgrades, crawlspace encapsulation, updated HVAC and a private well with NO monthly water bill. A rare combination of acreage, recreation, extensive improvements and flexible living in Southern Chesapeake. See attached Feature & Upgrade Sheet for even more! Make this an easy day and stop here first!

509 Ballahack Road, South Chesapeake

$935,000
5 Beds 3 Baths 10648261 MLS
Welcome to your private 3.25-acre country oasis, where luxury finishes, heavy-duty infrastructure, and absolute peace of mind converge. This beautifully updated single-story home offers an open-concept layout and highly functional spaces, making it a rare market find. INTERIOR HIGHLIGHTS Step inside to a bright, airy open floor plan where the living and dining areas flow seamlessly into the chef-inspired kitchen. The kitchen is outfitted with premium Cambria countertops for unmatched durability and sleek modern style. The primary suite serves as a spa-like retreat, boasting natural quartzite surfaces, a deep jetted soaking tub, and a massive 4x4 walk-in shower. Upstairs, a versatile finished room over the garage (FROG) and a charming attic dormer offer excellent bonus spaces for a home office, media room, gym, or guest quarters. OUTDOOR LIVING & ENTERTAINING Embrace the scenic acreage from your choice of outdoor living areas. Relax on the welcoming covered front porch, or host unforgettable gatherings on the expansive rear covered patio. The outdoor living experience is anchored by a fully equipped outdoor kitchen, great for weekend barbecues and dining al fresco while overlooking your sprawling, private acreage. THE ULTIMATE DETACHED WORKSHOP A true standout feature is the massive 2,200 sq. ft. detached workshop. This incredible building is fully powered and completely climate-controlled with heating and cooling, making it an ideal setup for a home business, car enthusiast, hobbyist, or extensive machinery storage. PREMIUM SYSTEMS & INFRASTRUCTURE No expense was spared on the home's mechanics and structural integrity: * Power Security: Whole-home generator supported by a recently added 500-gallon propane tank. * Efficiency: All-new energy-efficient windows and updated insulation throughout. * Roof & Plumbing: Roof is approx. 4 years young. All plumbing has been fully updated with zero cast iron. * Utilities: Tankless water heater for endless hot water; septic system recently serviced. Welcome Home.

1908 Benefit Road, South Chesapeake

$624,900
4 Beds 2.1 Baths 10647922 MLS
Nestled on more than four acres, this beautifully designed home offers an exceptional blend of space, style, and comfort. Filled with natural light, the inviting open floor plan creates a seamless flow between the living room, dining area, and stunning kitchen, making it well suited for both everyday living and entertaining. The kitchen is thoughtfully appointed with white cabinetry, an 8-foot island, generous counter space, a walk-in pantry, and stainless steel appliances. Upstairs, the spacious primary suite features a beautifully finished ensuite bath and a walk-in closet, while each additional bedroom is generously sized and includes its own walk-in closet. A two-car attached garage provides added convenience and storage. The covered rear porch overlooks the spacious backyard, offering a wonderful setting to relax, entertain, or simply enjoy the privacy and peaceful surroundings.

141 Indian Creek Road, South Chesapeake

$735,000
4 Beds 2.1 Baths 10647624 MLS
Welcome to your dream home in Hickory Landing! Situated on a premium corner lot in one of Chesapeake's most desirable neighborhoods, this stunning property is located in the highly sought-after Hickory school district. Outdoor living is an absolute oasis featuring an in-ground pool, a screened porch, immaculate professional landscaping, and an in-ground sprinkler system to keep it pristine. Plus, enjoy massive energy savings with fully paid-off solar panels! Inside, discover an entirely carpet-free layout boasting beautiful hardwood floors throughout both levels. The chef-inspired kitchen offers abundant cabinet space and two walk-in pantries. Even the oversized 2-car garage is meticulously finished with custom epoxy flooring. Upstairs, the luxurious primary suite serves as a private retreat, complete with two walk-in closets and a spa-like en-suite bathroom showcasing a custom tiled shower, deep soaking tub, and separate water closet. This rare gem truly has it all!

2121 Ferguson Loop, South Chesapeake

$599,000
4 Beds 2.1 Baths 10647636 MLS
Step into this Bentley Model with 4-bedrooms, 2.5-bath, 2,456 sqft offering modern living with community amenities buyers love. With a welcoming foyer entry leading to an open kitchen with mudroom & pantry, spacious dining area, and bright living room it's perfect for everyday comfort. Upstairs features all four bedrooms, including a generous primary suite with a custom walk-in closet system and convenient second-floor laundry. The fenced backyard provides great outdoor space for relaxing or entertaining, a blank slate ready for dream inspiration. Create your own private oasis with room for a pool, patio seating, or BBQ station. Solar panels convey at closing providing year-round savings at no cost to you! The front yard is professionally landscaped by the HOA, ensuring a polished curb appeal. This amenity rich Hickory Manor community with access to the clubhouse, pool, fitness center, playground, and scenic neighborhood spaces is the "one". Seller offering a flooring credit with acceptable offer, an excellent opportunity to customize the home to your style. Schedule your showing today!

614 Middleton Way, South Chesapeake

$925,000
4 Beds 3.1 Baths 10647773 MLS
Enjoy a slower pace of life as you relax on the front porch w/ morning coffee or watch loved ones play in the expansive yard. This beautifully remodeled farmhouse-style home sits on approx. 5.207 acres, extensively updated in 2021.Step inside to a dramatic 2-story foyer that opens to a spacious living area featuring kitchen, dining, & family room, ideal for everyday living & entertaining. The 1st-floor primary suite offers comfort & convenience. Upstairs, you'll find a generous flex space perfect for a 2nd living area, home office, playroom, or gym. The 2nd level also features an additional primary bedroom suite w/ private bath, plus 2 more bedrooms connected by a Jack & Jill bath. Abundant storage can be found throughout the home. The outdoor lifestyle is just as inviting. Spend your days fishing in your private pond, harvesting produce from the garden, or enjoying peaceful views of the neighboring horse farm from your kitchen window, at the end of the day, unwind by the pool

2008 Pocaty Creek Lane, South Chesapeake

$583,740
4 Beds 2.1 Baths 10647703 MLS
Welcome to the Shenandoah at Retreat at Edinburgh -Chesapeake’s premier 55+ low-maintenance community! Enjoy luxury townhome living with a modern open-concept design, gourmet kitchen with quartz countertops and stainless steel appliances, and a sunlit family room perfect for entertaining. The first-floor primary suite offers a spa-inspired bathroom, featuring a walk-in shower, and oversized walk-in closet, while upstairs features three spacious bedrooms, a loft, and ample storage. Community amenities include a resort-style pool, clubhouse, fitness center, dog park, walking paths, and more. Embrace the ultimate active adult lifestyle near fine dining, shopping, and beautiful parks. Photos and renderings are from builder's library, actual finishes and features may vary.

2009 Barton Lane, South Chesapeake

$1,200,000
4 Beds 3.1 Baths 10647623 MLS
Rare opportunity for true multi-generational living with exceptional flexibility, privacy, and space! This beautifully updated ranch offers one-level living with a finished room over attached 2-car garage, soaring ceilings, formal dining, first-floor laundry, and a luxury granite kitchen featuring KitchenAid appliances, built-in desk and a sun-filled eat-in. Relax year-round in the vaulted sunroom with a wood-burning fireplace or step outside to your private resort with a an inground saltwater pool, luxury landscaping, and expansive patio. The standout feature is the detached 3-car garage with a separate 3-bedroom, 1-bath apartment complete with kitchen, laundry, and private living space. Additional highlights include RV storage/hangar, workshop, Tesla charger, whole-house water filtration and softener, geothermal HVAC, encapsulated crawl space, buried drainage, sprinkler system, high-speed Cox WiFi, oversized walk-in attic, and extensive updates throughout.

1717 Long Ridge Road, South Chesapeake

$825,000
4 Beds 4 Baths 10647485 MLS
Welcome to this custom-built retreat situated on 5 acres in a highly desirable Grassfield school district. Thoughtfully designed this exceptional property offers generous indoor and outdoor space with features ideal for multigenerational living, entertaining, hobbies, and storage. The private in-law suite includes a kitchenette and its own screened porch, creating a welcoming space for guests or extended family. Upstairs, you’ll find two ensuite bedrooms, along with an additional bedroom that offers excellent potential as a theater room, home office, or flexible living space. Car enthusiasts, hobbyists, and those seeking extra workspace will appreciate the two-car attached garage, one-car detached garage with work area, and two storage sheds. From the inviting front porch—perfect for quiet mornings and scenic views—to the rear deck designed for gathering with family and friends, this one-of-a-kind property offers the space, privacy, and versatility today’s buyers are looking for.

1837 Benefit Road, South Chesapeake

$599,900
5 Beds 3 Baths 10646979 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.

789 Caddie Street, South Chesapeake

$725,000
5 Beds 3.1 Baths 10646366 MLS
See features sheet & survey attached — you’ll be amazed by this NEW custom home by Overholt Contracting (40+ yrs)! Must see now: modern floorplan with 2 spacious primary suites (or use one as a game room), 4 large bedrooms, first-floor home office, high-end kitchen & baths with quartz, freestanding tub + tiled shower, smart-home Wi-Fi, and full landscaping with sod. Sited on almost 1/2 acre in Hickory (Chesapeake) on city/county septic & water — NO HOA, additional buildings allowed, room for pool, boat or RV. James Hardie siding, carriage garage door with glass, brushed concrete patio. Closing cost assistance available with preferred lender Wes Flowers, Southern Trust. Also see something you would love to have but it’s not here. Contact me and my builder will have his design team work on it. He is easy going and ready to make your new home all about you!!! You wont find another build of this quality at this amazing price.

343 Ewell Lane, South Chesapeake

$597,740
3 Beds 3 Baths 10646287 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2205 Edwin Drive, South Chesapeake

$550,000
5 Beds 2 Baths 10646017 MLS
Embrace the off-the-grid lifestyle on 0.96 acres in Chesapeake's desirable Blackwater area, zoned for highly sought Hickory schools! This property maximizes self-sufficiency with pure water from a premium 600+ ft Certified Artesian well, a double tank water softener, and a tankless electric water heater. To drive utility costs down further, consider adding a maintenance-free solar panel program at no cost for instant savings without equipment hassles. Inside, the layout features a versatile room off the living room (perfect for an office or homeschool/playroom) plus a FROG, creating up to 6 bedroom-like spaces. The oversized septic system easily supports an ADU, multi-generational living, or rental income. Picture sipping morning coffee while collecting farm-fresh eggs from your backyard chickens. Best of all, sellers are open to negotiating improvements with an acceptable offer to help customize this homestead exactly to your liking!

1336 Blackwater Road, South Chesapeake

$899,800
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

$16,700
10645394 MLS
Three adjoining wooded residential lots available as a package in the established Hillcrest area of South Chesapeake. Includes 1534, 1536 & 1538 Tuck St. These contiguous parcels offer a unique opportunity for builders, investors, or buyers looking to get multiple lots for future development or personal use. Conveniently located near S. Battlefield Blvd and Johnstown Road with access to nearby shopping, dining, and major roadways. No utilities currently installed. No survey available. Buyer to perform all due diligence regarding lot dimensions, boundaries, zoning, buildability, utility availability/access, and development requirements with the City of Chesapeake and appropriate authorities. Rare opportunity to acquire three adjoining parcels in an established Chesapeake neighborhood with future potential.

1536 Tuck Street, South Chesapeake

$16,700
10645392 MLS
Three adjoining wooded residential lots available as a package in the established Hillcrest area of South Chesapeake. Includes 1534, 1536 & 1538 Tuck St. These contiguous parcels offer a unique opportunity for builders, investors, or buyers looking to get multiple lots for future development or personal use. Conveniently located near S. Battlefield Blvd and Johnstown Road with access to nearby shopping, dining, and major roadways. No utilities currently installed. No survey available. Buyer to perform all due diligence regarding lot dimensions, boundaries, zoning, buildability, utility availability/access, and development requirements with the City of Chesapeake and appropriate authorities. Rare opportunity to acquire three adjoining parcels in an established Chesapeake neighborhood with future potential.

1534 Tuck Street, South Chesapeake

$16,700
10645395 MLS
Three adjoining wooded residential lots available as a package in the established Hillcrest area of South Chesapeake. Includes 1534, 1536 & 1538 Tuck St. Offered at $16,700 per lot. These contiguous parcels offer a unique opportunity for builders, investors, or buyers looking to get multiple lots for future development or personal use. Conveniently located near S. Battlefield Blvd and Johnstown Road with access to nearby shopping, dining, and major roadways. No utilities currently installed. No survey available. Buyer to perform all due diligence regarding lot dimensions, boundaries, zoning, buildability, utility availability/access, and development requirements with the City of Chesapeake and appropriate authorities. Rare opportunity to acquire three adjoining parcels in an established Chesapeake neighborhood with future potential.

1538 Tuck Street, South Chesapeake

$574,900
4 Beds 2.1 Baths 10645491 MLS
Located in the Hickory school district, the home is less than one mile from the interstate and just minutes from the shopping, dining, and everyday conveniences of Edinburgh. With its bright interior, flexible layout, generous outdoor space, and convenient location, this home is ready to welcome its next owners. Tucked along a quiet, tree-lined street, this beautifully updated home offers a light, welcoming atmosphere and plenty of space to enjoy. Natural light fills the thoughtfully refreshed interior, creating bright and comfortable living spaces throughout. At the heart of the home is an inviting kitchen featuring stone countertops, newer cabinetry, stainless steel appliances, and durable LVT flooring—perfect for everyday living and entertaining. The spacious fourth bedroom above the garage offers wonderful flexibility as a home office, gym, playroom, guest suite, or private retreat. Outside, the expansive backyard provides plenty of room for gatherings, gardening, play, or simply relaxing beneath the open sky. The home also features a long list of valuable improvements, including PEX plumbing in place of the original polybutylene, an upgraded electrical panel, replacement of most windows, updated lighting and flooring, select exterior doors, siding, and trim. A private well serves the irrigation system, and the roof was replaced in 2014.

712 Woodcott Drive, South Chesapeake

$577,740
3 Beds 3 Baths 10645211 MLS
Welcome to The Charleston at Retreat at Edinburgh -a stunning 3-bedroom, 3-bath home. Enjoy an open great room with vaulted ceilings and a cozy fireplace, a gourmet kitchen with quartz countertops and stainless steel appliances, and a versatile Morning Room perfect for relaxing or entertaining. The spacious first-floor primary suite features a tiled shower, double vanity, and two large closets, while an upstairs bonus room with a full bath provides extra flexibility. Nestled in Chesapeake’s premier 55+ low-maintenance community, you’ll have access to a brand-new clubhouse, resort-style pool, walking paths, and more, all just minutes from fine dining, shopping, and beautiful parks. Experience the perfect blend of modern comfort and vibrant, active living in a tranquil coastal neighborhood you’ll love to call home. Photos are to be used as an example and do not represent exact listings selections. Taxes are estimated and will be updated after county assessment.

2166 Edwin Drive, South Chesapeake

$629,900
4 Beds 2.1 Baths 10645157 MLS
BUY THIS AWESOME HOME, WE'LL BUY YOURS!* Welcome to your low-maintenance luxury retreat in the sought-after 23322 zip code! This beautifully designed 4-bedroom, 2.5-bath home offers 2,598 sq ft of stylish, comfortable living with minimal upkeep. The highlight is the exceptional outdoor living space—a 529 sq ft covered, screened patio with premium epoxy flooring for entertaining, outdoor dining, or relaxing in privacy. An additional patio and custom walkway are surrounded by professionally landscaped, easy-care grounds. Enjoy a true lock-and-leave lifestyle with an HOA that maintains the front yard, giving you more time to enjoy life instead of yard work. Resort-style community amenities while shopping, dining, parks, and major commuter routes are all nearby. This home offers the perfect blend of luxury, convenience, and carefree living.

1910 Briton Lane, 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.