Refine Search
Map
Sort by
$525,000
4 Beds ⋅ 2 Baths ⋅ 10643319 MLS
Over $42,420 in Renovations! Beautiful Ranch with screened porch, detached garage, and circular driveway. Open Floor plan, spacious, ready for New Owners! Please see attached upgrade sheet.

858 Waters Road, South Chesapeake
$295,000
2 Beds ⋅ 1.1 Baths ⋅ 10642955 MLS
Welcome home to this beautifully updated 2-bedroom, 1.5-bath townhome tucked away on a quiet cul-de-sac in desirable Las Gaviotas. Head inside to a spacious living area featuring a cozy brick fireplace, fresh finishes, and an inviting layout perfect for everyday living or entertaining. Recent improvements include fresh paint, new flooring, new carpet, an updated full bath, new rear deck, front porch railing, sliding glass doors, gutters, and water heater. Energy-efficient windows and kitchen appliances were replaced in 2020. Upstairs offers two generously sized bedrooms, a dual-entry bath, and a large hall closet for extra storage. Enjoy a private fenced backyard with a new deck, ideal for relaxing or entertaining. Conveniently located near shopping, restaurants, parks, major interstates, Chesapeake City Hall, and award-winning Grassfield schools, this move-in ready home is ready for its new owner.

300 San Roman Drive, South Chesapeake
$710,000
4 Beds ⋅ 3.2 Baths ⋅ 10642808 MLS
A Full Acre of Land in the Heart of Southern Chesapeake.... Two Primary Suites. Room for Everyone! Over 3,600 sf. Renovated 4-bedroom 3 full baths and 1 1/2 baths home on a beautiful piece of land 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/owners 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. Sellers are motivated. Some images are digitally staged.

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
$524,900
3 Beds ⋅ 2 Baths ⋅ 10642197 MLS
Recently appraised at $600k, opportunities for instant equity like this are rare. Situated on 5 acres in Chesapeake's Grassfield High School district, this move-in-ready 3-bed, 2-bath home features a 720 sq. ft. detached, fully powered workshop—great for a contractor or hobbyist. Located near Deep Creek Park and the Dismal Swamp Canal Trail, enjoy peaceful surroundings, deer sightings, and views of sailboats on the Intracoastal Waterway. A 2012 renovation opened the layout, updated the kitchen and baths, and added central duct HVAC. Recent improvements include a new 3-ton heat pump (2023), whole-house paint (2024), new carpet (2025), and new utility room vinyl flooring, plus upgraded electrical, plumbing, and replacement windows. Outdoors features a fenced yard with mature fruit and fig trees throughout the property. Motivated seller facing an unexpected military relocation (PCS). Contact agent for more information!

317 George Washington Highway S, South Chesapeake
$635,000
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
$850,000
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
$419,900
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
$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
$49,900
10640840 MLS
Corner lot for sale in established neighborhood. Buy individually or in conjunction with 28 Hinton.

Folk Street, South Chesapeake
$724,900
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
$7,000
10640052 MLS

Lot 21 Arthurs Court, South Chesapeake
$7,000
10640049 MLS

1 Arthurs Court, South Chesapeake
$7,000
10640002 MLS
One of four adjacent parcels offered for sale in the Hillcrest neighborhood. Fantastic opportunity for holding as an investment, camping, urban archery hunting, riding fourwheelers, etc. Not required but you can buy all four and have a full acre for activities just 10 minutes from the heart of Great Bridge or Edinburgh! Roughly 900' from the paved St. of Arthurs Ct.

1737 Binford Street, South Chesapeake
$650,000
5 Beds ⋅ 3.1 Baths ⋅ 10639977 MLS
OPEN HOUSE SAT SEPT 12th 12-2PM! Beautifully appointed transitional style home offers the perfect balance of comfort, style & privacy. Nestled in cul-de-sac w/ no HOA, the home welcomes you w/ elegant natural stone accents that frame the covered front porch and enhance its timeless curb appeal. Inside, hardwood floors & ceramic tile complement a bright, thoughtfully designed layout. A versatile first-floor room provides an ideal space for a private office, guest suite, or flex room. The open-concept great room flows seamlessly into a well-equipped kitchen featuring granite countertops, stainless steel appliances, and generous workspace. Formal living and dining rooms offer inviting spaces for entertaining or everyday gatherings. Go outside to enjoy a private backyard retreat complete w/ an elevated Trex deck, saltwater pool, hot tub, gazebo & det. garage—creating an ideal setting for relaxing, entertaining & making the most of life at home. VA assumable loan.

803 Gresham Way, South Chesapeake
$365,000
3 Beds ⋅ 1 Baths ⋅ 10639800 MLS
Closing cost assistance! Welcome to 1073 Scenic Boulevard! This beautifully updated ranch-style home offers modern finishes, flexible living space, and a private setting on approximately .4 acres in the desirable Great Bridge area. Step inside to an open and inviting floor plan featuring updated flooring, fresh paint, modern fixtures, and a stunning kitchen w/ white shaker cabinetry, granite countertops, stainless steel appliances, and a large breakfast bar for entertaining. The spacious living and dining areas flow seamlessly together, creating a bright and comfortable atmosphere. The updated bathroom adds a fresh, contemporary touch, while the screened porch provides the perfect place to relax and enjoy the peaceful, wooded backdrop. Outside, you'll find a detached garage with electricity, additional storage shed, ample parking, and a large backyard offering endless possibilities for recreation, gardening, or gatherings. Conveniently located near top-rated schools, shopping, dining, and more!

1073 Scenic Boulevard, South Chesapeake
$7,000
10639836 MLS
One of four parcels adjacent to each other offered at just above tax value. Makes for great holding investment opportunity as the tax value has doubled to 6000 for the upcoming year, or for recreational use, riding fourwheelers, camping, etc. Come take a look! Roughly 900' from the paved section of Arthurs Ct.Ten minutes to the heart of Great Bridge or Edinburgh.

Lot 22 Trinkle Street, South Chesapeake
$444,000
3 Beds ⋅ 3.1 Baths ⋅ 10639592 MLS
Juniper Model built in 2021. 1st floor has flex room, can be used as office, mud room, or rec room. Also, separate bedroom with full bath. 2nd floor has huge open floor plan. Kitchen has large island, SS appliances, lots of cabinets, and large pantry. Great room with gas electric fireplace. Deck off front. Lots of windows for natural lighting. Please call night before to see.

450 Asuza Street, South Chesapeake
$489,900
4 Beds ⋅ 2 Baths ⋅ 10638400 MLS
WELCOME HOME! to this 1.5 story waterfront home on corner lot with 1st floor master bedroom with tray ceiling & 2 closets/master bath. Former model with converted garage-unlimited possibilities: he/she cave, office, daycare, home school, playroom, sewing/craft room, media room, bedroom, in-law apartment with separate entrance. Updates: new roof, new fence,freshly painted interior & beautiful! New carpet upstairs BR, new gas fireplace igniter & cleaned, large loft, new sink/vanity/floor-master bath w/jetted tub/separate shower. Kit with open bar to dining area, open dining area with pantry and mirrored accent wall, open family room with cathedral ceiling & sliding doors overlooking deck and water with nice shade tree & storage shed. Neighborhood park, clubhouse & pool for summer fun. Dog park and soccer park nearby as well as golf driving range, campground and shopping/dining. Hurry before it is gone!

2705 Sawyers Arch, 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
$465,000
4 Beds ⋅ 2 Baths ⋅ 10636036 MLS
Nestled in the sought-after Homestead Acres community of Chesapeake, this beautifully maintained brick ranch offers the perfect blend of comfort, charm, and functionality. Enjoy an inviting open floor plan with spacious living areas, an updated kitchen, bright sunroom, and screened-in porch to enjoy year-round. Step outside to a large backyard retreat complete with a built-in firepit, great for relaxing evenings under the stars. Additional features include reverse osmosis system, water softener maintained by Moody’s, and HVAC less than 3 years old with smart system technology. Conveniently located near top-rated schools, shopping, dining, and more. Please ask details from agent on short sale details.

2744 Horseshoe Drive, South Chesapeake
$1,089,000
5 Beds ⋅ 3.1 Baths ⋅ 10635945 MLS
NEW CONSTRUCTION HOME SITUATED ON 3 ACRE PRIVATE LOT. TRANSITIONAL STYLE HOME OFFERS AN OPEN FLOOR PLAN, 5 BEDROOMS, 3.5 BATHS & LOFT. KITCHEN WITH LARGE ISLAND, SPACE FOR SEATING AND OPENS TO THE GREAT ROOM AND FEATURES GRANITE COUNTERS, TILE BACKSPLASH, PANTRY AND GE CAFE STAINLESS APPLIANCES TO INCLUDE A REFRIGERATOR, GAS COOKTOP. FIRST FLOOR PRIMARY SUITE FEATURES A LARGE WALK IN CLOSET, WOOD SHELVING, FULL BATH, SHOWER, TILE SURROUND, SOAKING TUB, TILE FLOORING, DOUBLE VANITY, QUARTZ COUNTERS, SEPARATE WATER CLOSET. UPSTAIRS JACK & JILL BATH, AND A HALL BATH. LOFT CAN BE UTILIZED FOR TV/OFFICE/PLAYROOM THE CHOICE IS YOURS. COVERED SCREENED PORCH OFFERS A RETREAT-LIKE SETTING FOR HOMEOWNERS TO ENJOY. 3 CAR ATTACHED GARAGE, TANKLESS GAS WATER HEATER, LVP FLOORING ON 1ST FLOOR, CARPETING IN UPSTAIRS BEDROOMS, WOOD SHELVING FOR ALL BEDROOM CLOSETS, GRANITE COUNTERTOPS IN BATHS, ARCHITECTURAL SHINGLE/METAL ROOF.

2624 Ballahack Road, South Chesapeake
$771,900
4 Beds ⋅ 3.1 Baths ⋅ 10634877 MLS
Let’s be real—a "dream home" should do more than just look good in photos; it should actually make your life easier. The Engle welcomes you with a spacious dining room that’s practically begging for holiday gatherings (even if your "cooking" usually involves a delivery app). The kitchen is the undisputed heart of the home, featuring a massive island. The second floor is where the magic really happens. The primary suite is tucked away —offering a much-needed sanctuary from the household buzz—complete with dual walk-in closets (because sharing is overrated). In a rare move, every single guest bedroom also features its own walk-in closet, finally solving the "where do we put all the stuff?" dilemma. Plus, the central loft is a total chameleon, ready to serve as a cozy media den or a quiet home office. The Engle is all about "Truly Living" with plenty of room to breathe. Ask about our current Incentives and come see us at the design center to start personalizing yours!

MM Taft (Engle B-1) Road, South Chesapeake
$844,900
4 Beds ⋅ 3.1 Baths ⋅ 10634845 MLS
Indulge in the versatile beauty of The Davidson, a stunning floor plan that perfectly balances formal elegance with a spacious, modern flow. The heart of this 3,124+ square foot home is a gourmet kitchen featuring a massive multi-seating island, seamlessly overlooking a great room designed for grand holiday feasts and cherished family memories. On the main level, the stately primary suite serves as a true sanctuary, complete with a spa-inspired en-suite and a room-sized walk-in closet, while a sunlit flex room offers the perfect space for a quiet home office or a cozy reading nook. Upstairs, three additional bedrooms and a convenient second-level laundry station ensure plenty of space and privacy for guests and growing families alike. From the charming country front porch to the adaptable loft, The Davidson provides a wholesome, rewarding living experience on spacious 5+ acre homesites within the Grassfield School District. Contact LA2 today for an appointment!

MM Taft (Davidson Homesite A-2) Road, South Chesapeake
$692,950
4 Beds ⋅ 2.1 Baths ⋅ 10634859 MLS
The Derring isn’t just a house; it’s a high-energy hub designed for the pulse of a busy, modern life. Forget those traditional, boxy layouts—this plan throws the doors open with a massive, light-drenched great room that flows straight into a kitchen built for "main character" energy, complete with a substantial floating island that’s destined to be your morning coffee spot and evening social headquarters. While the main floor offers a versatile flex room designed for a high-productivity home office or a sun-soaked reading nook, the second floor is where everyone gets their own space to recharge. We’re talking four spacious bedrooms, each featuring its own walk-in closet (yes, really!), all centered around a massive loft that’s ready to become anything from a cinema to a dedicated gaming zone. The Derring is all about "Truly Living" without the clutter. Snag those Trusted Lender Incentives and book your design center appointment to see how we can level up your lifestyle!

MM Taft (Derring A-5) Road, South Chesapeake
$849,900
4 Beds ⋅ 3.1 Baths ⋅ 10634643 MLS
The Holden, where every detail is meticulously crafted to elevate your daily routine. Morning light floods the first-floor primary wing, a sanctuary complete with a room-sized walk-in closet and a spa-inspired bath. The heart of this home is a masterclass in modern architecture, featuring a soaring great room that flows into a chef’s kitchen and sun-drenched breakfast area—designed for everything from quiet espresso shots to grand holiday hosting. Beyond the communal spaces, The Holden offers an intelligent layout designed for the modern lifestyle, including a dedicated front-end flex space designed for a quiet home office. Venture upstairs to discover the expansive loft and media room, providing the perfect canvas for a cinema, a library, or a high-tech gaming hub. With 4 to 5 generous bedrooms and the seamless functionality of a mudroom and independent laundry, this home doesn't just provide space; it provides a tailored backdrop for your most cherished memories.

MM Taft (Holden 2-A) Road, South Chesapeake
$695,351
3 Beds ⋅ 2 Baths ⋅ 10633226 MLS
The Squire offers a living experience centered on ease, elegance, and flexibility. The main-level primary suite provides a peaceful escape, thoughtfully positioned and enhanced by a spa-inspired bathroom and a generously sized walk-in closet. Flowing from room to room, the home’s open layout creates a natural sense of connection. The great room, filled with natural light, opens seamlessly to a well-appointed kitchen designed to handle both everyday meals and special occasions with equal ease. With the option for 3 to 5 bedrooms—including a dedicated study or home office—The Squire adapts effortlessly to your needs, whether you're growing, hosting, or simply enjoying quiet moments at home. Ask about available Trusted Lender Incentives to make this home yours. Call today to make an appointment at our design center.

MM Fields At Taft (Squire A-5) Road, South Chesapeake
$769,900
3 Beds ⋅ 2.1 Baths ⋅ 10633234 MLS
In The Kentland, every day unfolds in a home designed for both comfort and connection. The primary suite offers a retreat, where natural light and generous proportions create a relaxing escape from the pace of daily life. Thoughtful architectural details, including elevated ceilings, add depth and character throughout. The main living area is designed with versatility in mind, bringing together the great room, kitchen, and breakfast space into one cohesive environment. Whether preparing meals, entertaining guests, or enjoying a quiet night in, this central space easily adapts to your needs. On the main level, two secondary bedrooms provide flexibility for guests or family members. Upstairs, a spacious loft expands the home’s possibilities—designed for a home office, creative studio, or entertainment space tailored to your lifestyle. Design center appointments available now! Trusted lender incentives available.

MM Taft (Kentland B-1) Road, 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.