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$755,000
5 Beds 3.2 Baths 10642808 MLS
A Full Acre. Two Primary Suites. Room for Everyone — 1833 Benefit Rd, Chesapeake VA. Over 3,600 sf. Motivated sellers! Renovated 5-bedroom home on a full acre in Chesapeake — brand new carpet, all freshly painted. The space, privacy, and flexibility that rarely come together at this price point. Two primary suites, one up and one down, give you real options: multigenerational living, long-term guests, or a main-level owner's retreat. The downstairs in-law suite has its own private entrance — space for older parents, adult kids, or a home business with client access that never touches your living space. The renovated kitchen features stainless steel appliances and opens to living areas built for gathering. The upstairs primary offers double sinks and a large walk-in closet. A mudroom with half bath handles the daily traffic so the rest of the house stays put together. Outside is where this property separates itself. A wrap-around deck surrounds the above-ground pool — your built-in venue for summer weekends. The roundabout driveway and attached 2-car garage mean parking is never a problem, whether it's a cookout for twenty or just everyday life. And the full acre gives you room to add, expand, or simply breathe — no neighbors ten feet from your window. Homes with this much land, this much flexibility, don't sit long in Chesapeake. Schedule your showing today.

1833 Benefit Road, South Chesapeake

$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

$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

$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

$935,000
6 Beds 3.1 Baths 10642291 MLS
Welcome to luxury living in Chesapeake's coveted Cahoon Plantation community! This custom brick home was built in 2012. The stunning 6-bedroom home showcases a spacious open-concept design that works for both everyday living & entertaining. The beautifully appointed kitchen flows seamlessly into the main living and dining areas, creating a bright, inviting space filled with natural light & modern elegance. The kitchen offers maple cabinets, range hood, backsplash granite countertops & brand-new matte black Kitchen Aid appliances. The first-floor primary bedroom has an ensuite bathroom w/ shower, soaking tub, dual vanities and large walk-in closet. Upstairs the generously sized bedrooms provide flexibility for family, guests, or a home office. Step outside to your backyard retreat featuring a large, heated saltwater in-ground pool, play area, gas fire pit all while overlooking the woods. This home has been meticulously maintained and is ready for its new owners. Just minutes from interstates, restaurants & shopping.

409 Torre Pine Court, 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

$515,000
4 Beds 2.1 Baths 10641783 MLS
WELCOME HOME TO THIS BEAUTIFULLY UPDATED WATERFRONT PROPERTY TUCKED AWAY ON A QUIET CULDESAC. RECENT UPDATES INCLUDE LVP FLOORS, SOLID OAK STAIRS, FRESH PAINT THROUGHOUT. NEW 6 BURNER GAS RANGE WITH BEAUTIFUL HAND MADE BUTCHER BLOCK COUNTERS SURROUNDING. NEWER GAS FIREPLACE COMPONENTS, WATER FILTRATION SYSTEM AND RECENTLY SERVICED HVAC. BACKYARD FEATURES AN ABOVE GROUND POOL WITH POOL HOUSE AND ALL EQUIPMENT, SWINGSET, GORGEOUS RAISED FLOWER BEDS, BEAUTIFUL FRUIT TREES AND OWNERS HAVE CAUGHT 5 POUND BASS RIGHT FROM THEIR BACK YARD. EASY ACCESS TO PLUMBING COMPONENTS MAKES FOR EASY MAINTENANCE. THIS HOUSE IS MOVE IN READY WITH SO MANY GREAT FEATURES. MOTORCYCLE PAD AND COVER CONVEY AS WELL AS SOME FURNITURE.

801 Winter King Court, South Chesapeake

$539,000
3 Beds 2.1 Baths 10641886 MLS
Welcome home to this beautifully appointed, move-in ready Seafield model in Eagle Pointe, Chesapeake's premier 55+ resort-style community. The gourmet eat-in kitchen features granite countertops, stainless steel appliances, gas range, breakfast bar, & butler's pantry plumbed for a sink. Enjoy both casual & formal entertaining with an eat-in kitchen & elegant formal dining room. Relax year-round in the bright Florida room w/custom doors. Plantation shutters & custom window treatments enhance the home's timeless appeal. The first-floor primary suite offers a spacious walk-in closet & spa-inspired bath w/split vanities & walk-in shower. Upstairs features a loft overlooking the family room, two bedrooms, full bath, & walk-in storage/mechanical room. Patio w/electric awning, gas grill line, certified green construction, spray foam insulation, & Rinnai tankless water heater. Enjoy The Bay Club's indoor/outdoor pools, fitness center, ballroom, library, billiards, game rooms, and more!

1517 Eagle Glen Drive, 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

$560,000
4 Beds 2.1 Baths 10641575 MLS
Exceptional 4-bedroom, 2.1-bath home perfectly positioned on a corner lot overlooking the fairway in highly sought-after Las Gaviotas & the Grassfield school district. The first floor offers two generous living areas, a formal dining room, and an updated kitchen featuring granite countertops, tile backsplash, gas range, and ample cabinetry. Large windows frame peaceful views of the golf course, creating a bright, inviting atmosphere throughout. Four spacious bedrooms with the primary including a walk-in closet & a beautifully finished primary ensuite bathroom with a soaker tub, separate shower, and double-sink vanity. Step outside to enjoy composite decking & a backyard that opens directly to the fairway—an ideal setting for morning coffee, evening unwinding, or hosting friends. Just minutes from top-rated schools, shopping & dining, this home blends convenience with the charm & prestige of golf-course living. A rare opportunity in one of Chesapeake’s most desirable neighborhoods.

400 Las Gaviotas Boulevard, South Chesapeake

$974,500
4 Beds 3.1 Baths 10641558 MLS
Grace, Beauty, Functionality, Beautiful private location (acreage on a cul de sac), only 10 lots on clear land bordered by mature trees as a backdrop. The primary bath is oppulant includes over sized vanity, soaking tub, large tile shower and including an extra large closet. There's a second en suite on the first floor along with a flex room. Amazing storage over the THREE car garage with room for EVERYTHING. Newest feature is a "butlers kitchen" complete with full sink tucked just behind the well equiped main kitchen. Two additional large bedrooms upstairs. Covered rear porch with an amazing view! You couldn't ask for more. This semi custom building package is hard to beat! We have additional lots and plans available. This will be the last acreage neighborhood to be appproved within the city. No main road lots here! If you are looking for new construction it's a definite "MUST SEE"! Ponds, wildflower field, private walking trail and more add up to an exceptional "positive vibe" . No upgrades needed, come see! Preferred lender incentives

4020 Tucker Lane, South Chesapeake

$899,999
6 Beds 3.1 Baths 10641499 MLS
Welcome to your own private retreat in the heart of Grassfield! Nestled on approximately 5 acres, this beautifully maintained 6-bedroom, 3.5-bath home offers more than 4,200 square feet of space designed for both everyday living and unforgettable entertaining. Inside, you'll find generous living areas with room for everyone—whether you're hosting holiday gatherings, working from home, or simply enjoying quiet evenings with family. Go outside to enjoy the peaceful surroundings, then unwind in the hot tub, which conveys with the home, making it easy to relax under the stars after a long day. Now offered at an improved price, this exceptional property also includes a seller-paid carpet allowance with an acceptable offer, giving you the opportunity to add your own personal style before moving in. If you've been dreaming of acreage, privacy, and a home that offers the perfect blend of comfort, flexibility, and room to grow, this Grassfield gem is ready to welcome you home. Schedule your private tour today and experience everything this incredible property has to offer.

2536 Seven Eleven Road, South Chesapeake

$624,900
4 Beds 2 Baths 10641403 MLS
Enjoy the tranquility of this charming ranch nestled on a private lot spanning nearly 3 acres. The inviting floor plan welcomes you with a cozy living room featuring a fireplace and wet bar, creating a great space to relax or entertain. At the heart of the home, the kitchen is filled with natural light from two large windows and offers ample cabinet and counter space, along with stainless steel appliances. Just off the kitchen, the dining area allows for effortless gatherings and everyday living. The spacious primary suite provides a peaceful retreat with a large walk-in closet and private ensuite bathroom. The additional bedrooms are generously sized, offering flexibility for family, guests, or a home office. Outside, the expansive backyard and screened porch provide endless opportunities to enjoy the surrounding natural beauty and peaceful setting. Experience the best of country living with the convenience of a short commute to shopping, dining, and everyday amenities.

2448 Johnstown Road, 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

$649,900
6 Beds 2.1 Baths 10641222 MLS
Located in Chesapeake's sought-after Grassfield school district, this freshly painted, move-in ready home offers space, flexibility, and modern updates. The open floor plan is anchored by a spacious kitchen featuring Samsung Bespoke appliances, generous cabinet and counter space, and a pantry, creating a natural gathering place for everyday living and entertaining. The third floor was expanded in 2021 to include two finished rooms, providing flexible space for a home office, media room, playroom, hobbies, guests, or additional bedrooms. Major improvements include a new 1st floor HVAC in 2024 and 2nd/3rd floor HVAC installed in 2021. Outside, you'll find an expanded extra-wide driveway, EV charger, fully fenced backyard, and a spacious deck ready for cookouts, relaxing evenings, or weekend gatherings. Conveniently located near shopping, dining, major highways, and everyday conveniences, this home combines space, function, and updates in one of Chesapeake's most desirable locations. Some photos are virtually staged.

568 Waters Road, South Chesapeake

$423,000
3 Beds 2.1 Baths 10641328 MLS
This end unit townhome has been meticulously cared for by the original owners since purchasing it new in 2023. From the welcoming foyer, LVP flooring throughout the 1st floor leads to a stunning great room, which flows nicely into the dinette and gourmet kitchen that provides abundant counter space for all your kitchen storage needs. Upstairs, 3 spacious bedrooms and 2 full bathrooms provide privacy and comfort. Your luxurious owner’s suite includes tray ceilings, a generous sized walk-in closet, a double vanity sink and large stand up shower. When you live in Cardinal Meadows, you’ll love the easy access to Route 17, Cedar Road, I-64 and I-464, not to mention being located right off Cahoon Parkway puts you just minutes away from all your shopping needs at Cahoon Commons.

1607 Songbird Lane, South Chesapeake

$649,900
4 Beds 2.1 Baths 10641240 MLS
Welcome Home! A Stephen Alexander build where timeless design meets the comfort of everyday living. Tucked away on nearly half an acre in sought-after Grassfield, this beautifully cared-for home has been lovingly maintained by its original owners since day one. 4 spacious bedrooms, 2.5 baths, and nearly 3,200 sqft of inviting space with room for both quiet mornings and lively gatherings. The screened-in porch creates the perfect spot for coffee, conversations, and slow summer evenings. Outside, the backyard feels like a private escape, backing to peaceful woods with space to play, relax, and enjoy nature right at home. Homes this well cared for, in this setting, and with so much character are hard to find. Come see all that 2008 Burson Drive has to offer— a place designed not just to live, but to make memories!

2008 Burson Drive, 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

$674,000
5 Beds 2.1 Baths 10640526 MLS
Upgrade your lifestyle in highly sought-after Grassfield with this move-in ready home offering nearly 3,000 sq ft of relaxed, coastal living space. Impeccably maintained, it features open gathering areas and oversized bedrooms. The chef's kitchen showcases granite countertops, custom cabinetry, and a built-in pet station. A dedicated library with custom bookshelves makes an ideal space for reading, relaxing or a home office. The spacious primary retreat boasts double doors, tray ceilings, a spa-inspired en suite, and a custom walk-in closet. Step outside to a fenced backyard with dual patios, a built-in firepit, and raised garden beds. Relax on the screened-in porch and enjoy the rare privacy of a protected, undeveloped nature preserve. Buyer may choose between a flooring allowance or significant ***Rate Buy Down** with acceptable offer, allowing buyers to personalize select finishes. Seller wishes 3 televisions to convey to buyer.

952 Checkerspot Way, 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

$609,900
5 Beds 3 Baths 10639976 MLS
Welcome home to this spacious & beautifully maintained residence located in a highly sought-after neighborhood. Offering a versatile floor plan & generous living spaces, this home is designed to accommodate a variety of lifestyles.The main level features dining room & living room w/built ins, providing the perfect setting for entertaining, hardwood flooring flows throughout downstairs living areas, newer carpet adds comfort throughout the upper level. A rare & desirable feature, this home offers spacious first floor bedroom w/full bath. The upstairs primary retreat boasts an elegant tray ceiling & two closets. All 5 bedrooms include walk-in closets & ceiling fans, providing ample storage & comfort for everyone! The updated kitchen is a chef's dream with SS appliances, gas range,granite countertops,new microwave & refrigerator. It flows seamlessly to a breakfast nook & sunroom! Private backyard oasis, featuring stamped concrete patio & firepit to enjoy peacful evenings!!!

712 Creekwood Drive, South Chesapeake

$675,000
4 Beds 2.1 Baths 10640188 MLS
Welcome to this meticulously maintained one-owner home! Offering 4 bedrooms, 2.5 baths, and approximately 3,415 square feet, this spacious residence combines timeless quality with thoughtful updates throughout. Step inside to find soaring cathedral ceilings, generously sized rooms, and a floor plan designed for both everyday living and entertaining. The beautifully updated kitchen features quality cabinetry, Thermador gas range, and ample workspace for the home chef. The inviting living spaces provide comfort and flexibility, while the private office is great for working from home. Major improvements include a tankless water heater, Pella windows and doors, vinyl siding, and updated flooring. The walk-up floored attic provides exceptional storage opportunities. Outside, you'll discover stunning landscaping that creates a beautiful setting year-round. Enjoy relaxing on the welcoming front porch or entertaining in the spacious backyard. The irrigation system helps keep the grounds looking their best with minimal effort. Located in the highly sought-after Las Gaviotas area of Chesapeake, this home offers convenient access to shopping, dining, parks, schools, and major commuting routes. Pride of ownership is evident throughout this exceptional property, move-in ready and waiting for its next chapter!

1006 Seville Drive, 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.