Refine Search
Map
Sort by
938 Olmstead Street, South Chesapeake
$630,000
5 Beds ⋅ 3.1 Baths ⋅ 10657755 MLS
Gorgeous & 4-years-young in community-friendly Culpepper Landing with scenic outdoor areas, clubhouse & pool! Huge open & bright floor plan enhanced by classic neutral décor. Enjoy flexible living spaces great for home office, study, dining room or homeschool station. Dreamy kitchen with an abundance of cabinetry, counter space & massive breakfast bar great for gathering & entertaining. Inviting family room sits at the heart of the home & opens to covered porch overlooking fenced backyard. Extra highlights include a convenient mudroom, organization area & finished room over the garage with full bath offering endless possibilities for a guest suite, media room or private retreat. With 5 bedrooms & 3.5 bathrooms, there's plenty of room for everyone to spread out. Elegant primary suite features exercise area, walk-in closet, dual-sink vanity & oversized shower with double shower heads. This is the Total Package & Across the street from brand NEW elementary school opening 2027-2028.

938 Olmstead Street, South Chesapeake
2432 Youngman Road, South Chesapeake
$259,900
2 Beds ⋅ 1 Baths ⋅ 10657727 MLS
MUST SEE! Beautiful move-in ready home with fantastic updates, including a new roof, siding, flooring, appliances, fresh paint, and more. Features spacious bedrooms, an open-concept layout, and a great kitchen. Situated on a large lot (nearly 6,800 sq. ft.) with a massive backyard offering endless possibilities. Conveniently located near shopping, dining, military bases, and the airport. Schedule your private tour today!

2432 Youngman Road, South Chesapeake
3019 Roundtable Drive, South Chesapeake
$345,000
4 Beds ⋅ 2 Baths ⋅ 10657719 MLS
Welcome to 3019 Roundtable Drive. A charming ranch-style home in the heart of Chesapeake. This 4-bedroom, 2-bathroom home offers an open layout everyday life or entertainment. recent updates include granite countertops w/backsplash in kitchen, new Roof, HVAC-2026, Hot water Heater-2026 and fresh paint throughout home. Outside, there’s a large backyard that offers plenty of space for entertaining, gardening, or play. Conveniently located on a quiet cul-de-sac near shopping, dining, and local amenities, this home is ready to welcome you. Fence and shed convey as is. Schedule your showing today!

3019 Roundtable Drive, South Chesapeake
1021 Roundtable Court, South Chesapeake
$260,000
3 Beds ⋅ 1.1 Baths ⋅ 10657685 MLS
Welcome to 1021 Roundtable Court! This beautifully renovated, move-in-ready Chesapeake home offers modern upgrades, stylish finishes and exceptional convenience! Enjoy fresh interior paint, updated flooring, new lighting, updated trim and new blinds throughout. The refreshed kitchen features brand-new stainless steel appliances, including a refrigerator, electric range, microwave, and garbage disposal. Both bathrooms feature updated vanities, faucets, and fixtures. Additional improvements include new interior and exterior doors, storm doors, updated vinyl siding, exterior trim, and a replacement window. Enjoy modern technology with a smart ceiling fan that operates by remote or through a Wi-Fi-connected app. The washer and dryer also convey, making your move even easier! The roof and HVAC system were replaced approximately 10 years ago. With extensive interior and exterior improvements, this home offers the comfort, style, and convenience today’s buyers appreciate. This one is a gem - you don't want to miss out! Schedule your showing today!

1021 Roundtable Court, South Chesapeake
844 Parapet Road, South Chesapeake
$345,000
4 Beds ⋅ 2.1 Baths ⋅ 10657384 MLS
Welcome to this spacious two-story home offering a fantastic layout and incredible potential! The first floor features a formal living room, separate dining room, a cozy den, and a convenient half bath. Upstairs, you will find three comfortably sized bedrooms alongside a primary suite complete with its own private en suite bath. Excellent storage and parking are provided by the attached two-car garage. Situated in a prime location just minutes from shopping, local dining, entertainment, major interstates, and area bases. This property is a wonderful opportunity to bring a little elbow grease, add your personal touches, and truly make it your own. Call today to schedule your private showing! Some virtual staging utilized in pictures.

844 Parapet Road, South Chesapeake
512 Bay Oak Drive, South Chesapeake
$334,900
4 Beds ⋅ 2.1 Baths ⋅ 10657097 MLS
Welcome home! This 4 bedroom, 2.5 bathroom home in the heart of Chesapeake is waiting for you! With over 1,700 square feet, there’s ample space to make your own! The screen in deck opens to a spacious yard that is great for entertaining, gardening, or anything you’d like! The attached garage allows for the possibility for extra parking or storage space! Conveniently located with easy access to major highways, making commuting or travel a breeze! Call today for more information and to schedule your tour!

512 Bay Oak Drive, South Chesapeake
2317 Firman Street, South Chesapeake
$429,900
10657200 MLS
Beautiful setting on 2.198 acres on Deep Creek canal of the intercoastal waterway. Peaceful setting with mature trees. Potential to subdivide, buyer to do their due diligence. Current home is uninhabitable. Total road frontage is 208 ft. The Wetlands Assessment is in documents. Do not walk the property without a scheduled appointment.

2317 Firman Street, South Chesapeake
1425 Glendale Avenue, South Chesapeake
$339,900
3 Beds ⋅ 2 Baths ⋅ 10657065 MLS
Charming ranch with thoughtful updates throughout. The interior has been freshly painted and features new lighting, laminate flooring, and carpet. Upon entering, you are welcomed by a cozy family room with a stone fireplace. The eat-in kitchen offers all new cabinets, granite countertops, and stainless steel appliances. The home offers three spacious bedrooms and two full bathrooms, both updated with new tubs and tile surrounds. The large fenced backyard provides plenty of room to enjoy the outdoors. An attached garage adds convenient parking and storage. Schedule your private tour today!

1425 Glendale Avenue, South Chesapeake
3204 Eight Star Court, South Chesapeake
$560,000
4 Beds ⋅ 2.1 Baths ⋅ 10656875 MLS
Now This Is a Place You Can Call Home! This beautiful 4-bedroom, 2.5 bath home is nestled on a quiet cul de sac, offering space, comfort, and charm. Featuring a grand two-story foyer, hardwood flooring throughout the first floor, formal living and dining rooms, and a spacious gathering room with a cozy gas fireplace. The eat in kitchen boasts 42-inch cabinets, generous counter space, and a custom backsplash. Enjoy the large sunroom with vaulted ceilings, perfect for relaxing or entertaining. The spacious primary suite features a sitting area, walk in closet, double sink vanity, jetted tub, and separate shower. A huge backyard offers plenty of room for outdoor fun and gatherings, plus a storage shed. This home has it all! Schedule your showing today and make it yours!

3204 Eight Star Court, South Chesapeake
2610 Elkhart Street, South Chesapeake
$450,000
10656716 MLS
Build-ready townhome development opportunity in Chesapeake! This 0.558-acre parcel is approved for 5 townhome units and offers a rare chance to step into an already entitled project. Zoned R-TH-1 with plans and approvals in place, saving valuable time and development costs. Appraisal, site plans, and renderings available. Great location with strong resale potential and easy access to major commuter routes.

2610 Elkhart Street, South Chesapeake
3342 Martin Johnson Road, South Chesapeake
$1,650,000
5 Beds ⋅ 3.2 Baths ⋅ 10656180 MLS
Quiet Luxury. Architectural Artistry. This Custom Built Estate was designed not simply to be lived in, but to be experienced on 4 acres, 5,900 sqft (plus add'l 980 ROG). The dramatic, soaring ceilings & windows throughout a 2-story family rm w/stone fireplace, along w/every custom architectural detail make a statement of true Luxury. From the picturesque curb appeal to first floor Primary Suite & your own private spa, a cedar-lined wellness retreat w/hot tub. The expansive fl plan provides flexibility for formal gathering & relaxed everyday living. This home was thoughtfully designed, w/ 4 add'l spacious bedrms, generous living & entertainment areas, abundant nat'l light & craftsmanship throughout. New 6 burner-gas Wolf range in large kitchen, Trex board decking outside, endless possibilities to entertain & peace/privacy. An inground pool, pool house, pergola & plenty of open space. Large ROG is ready for you to make it your own movie/game room! Ask your agent for feature sheet!

3342 Martin Johnson Road, South Chesapeake
3145 Codorus Street, South Chesapeake
$490,000
4 Beds ⋅ 2.1 Baths ⋅ 10655704 MLS
Seller is willing to negotiate CCA/rate buy down! VA Assumable rate of 2.875%. Beautifully updated and move-in ready, this home offers the perfect blend of comfort, style, and community. Recent improvements include luxury vinyl plank flooring throughout, a beautifully renovated primary bath with a spacious walk-in shower, and the addition of a fourth bedroom for added flexibility. Outside, the large backyard is framed by mature weeping willow trees, creating a peaceful retreat on a quiet side street. Beyond your front door, enjoy a lifestyle that’s hard to find—golf cart rides to the clubhouse, afternoons at the resort-style pool, workouts in the fitness center, visits to the dog parks and playgrounds, and a calendar full of neighborhood events including community picnics, book club, cigar & bourbon nights, festive holiday celebrations, and the beloved Christmas golf cart parade. Experience everything this vibrant, close-knit community has to offer in sought-after Culpepper Landing.

3145 Codorus Street, South Chesapeake
2604 Elkhart Street, South Chesapeake
$395,000
4 Beds ⋅ 2 Baths ⋅ 10655711 MLS

2604 Elkhart Street, South Chesapeake
3240 Joplin Lane, South Chesapeake
$605,000
5 Beds ⋅ 3.1 Baths ⋅ 10655526 MLS
Beautifully maintained 5-bedroom, 3½-bath home situated on nearly half an acre, featuring generously sized rooms, beautifully landscaped grounds, and tasteful brick garden beds filled with year-round evergreens. The inviting interior offers a sunroom, spacious eat-in kitchen, formal dining room, and formal living room, providing plenty of room for everyday living as well as entertaining family and friends. Step outside to the huge backyard, where you'll find plenty of space to gather and enjoy the outdoors. A charming pergola. Seller offering closing cost assistance with full price offer

3240 Joplin Lane, South Chesapeake
3433 Martin Johnson Road, South Chesapeake
$385,000
3 Beds ⋅ 2 Baths ⋅ 10655347 MLS
Welcome to this charming 3-bedroom, 2-bath Cape Cod nestled on 1.4 private acres in the Deep Creek area of Chesapeake! This property offers the perfect blend of peaceful outdoor living and everyday convenience. Enjoy gardening in the fenced garden, unwind in the wooded backyard, or take advantage of easy access to the nearby Portsmouth Ditch Trail for walking, biking, and outdoor recreation. Inside, you’ll find a warm and inviting layout with classic Cape Cod character and plenty of space to make your own. Whether you’re looking for room to spread out, enjoy nature, or simply escape the hustle while staying close to shopping, dining, and major commuting routes, this home checks all the boxes. Don’t miss this unique opportunity to own your own slice of Deep Creek!

3433 Martin Johnson Road, South Chesapeake
3404 Winterhawk Court, South Chesapeake
$444,900
4 Beds ⋅ 2.1 Baths ⋅ 10655111 MLS
THE WRAP AROUND PORCH WELCOMES YOU TO THIS BEAUTIFUL HOME THAT TRULY HAS IT ALL. THE SPACIOUS FAMILY ROOM OPENS IMMEDIATELY TO THE RIGHT OF THE FRONT DOOR AND WITH ITS NEWER LAMINATE FLOORING LEADS YOU INTO THE SEPARATE DINING ROOM. LARGE GREAT ROOM WITH CATHEDRAL CEILINGS AND SKYLIGHTS ADD SPACE AND LOTS OF NATURAL LIGHT. SPACIOUS KITCHEN WITH BREAKFAST NOOK AND FRENCH DOORS TO THE GENEROUS DECK, GREAT FOR ENTERTAINING AND OUTDOOR LIVING. LARGE MASTER BEDROOM WITH WALK IN CLOSET AND ATTACHED BATHROOM. LARGE FROG WITH PLENTY OF STORAGE. THE LARGE FENCED IN BACK YARD OFFERS ROOM FOR A GARDEN, PLAYGROUND AND EVEN A POOL!! ATTACHED 2 CAR GARAGE!! COME SEE TODAY!

3404 Winterhawk Court, South Chesapeake
737 Big Bear Lane, South Chesapeake
$545,000
4 Beds ⋅ 2.1 Baths ⋅ 10655103 MLS
Welcome Home! This 4 bedroom 2.5 bath home located in Beautiful Culpepper Landing is waiting for you to move right in. This well maintained home has an open floor plan that allows tons of natural light. Gourmet kitchen w/island, granite countertops , newer appliances and plenty of cabinet storage. Snuggle up to cozy fireplace in the large family room. Upstairs primary suite with walk in closet, double vanity and 3 more bedrooms, a utility room and a full bath. And don't forget to checkout the garage! Pool, Clubhouse, Playgrounds. Minutes to shopping, restaurants.

737 Big Bear Lane, South Chesapeake
000 Pioneer Lane, South Chesapeake
$125,000
10654995 MLS
Discover this 0.6-acre lot in the heart of Deep Creek! Tucked away along a residential lane, this partially wooded parcel offers a peaceful country setting for your future home. The property has been surveyed, and the seller has completed a preliminary soil report indicating potential for a single-family home. Enjoy the charm of country living and make Pioneer Lane the setting for your next chapter!

000 Pioneer Lane, South Chesapeake
609 Veery Street, South Chesapeake
$379,500
3 Beds ⋅ 2.1 Baths ⋅ 10654632 MLS
Wonderful end-unit townhome in the sought-after community of Culpepper Landing! Great open concept living area with hardwood flooring and large kitchen for entertaining!!! This property has been well maintained and includes granite counters throughout with high ceilings and all the updates that like-new construction provide!! Includes a huge, 2 car garage with plenty of storage as well as an inviting patio/courtyard area! Enjoy the clubhouse, pool, exercise room and playgrounds!! See this one today before it is SOLD!!!

609 Veery Street, South Chesapeake
732 Colonel Byrd Street, South Chesapeake
$799,900
6 Beds ⋅ 4 Baths ⋅ 10654449 MLS
Welcome to this beautiful home in the highly sought-after community of Culpepper Landing! Offering an impressive 3,656 square feet of living space, 6 bedrooms, 4 full bathrooms, and a dedicated office that provides the flexibility of a 7th room, this beautifully designed home delivers the perfect blend of space, comfort, and functionality. Step inside to discover an inviting open-concept floor plan, designed for everyday living and effortless entertaining. The kitchen is the heart of the home, showcasing custom cabinetry and a large center island creating a welcoming space for gatherings with family and friends. A convenient first-floor bedroom provides added flexibility for guests or multigenerational living. With generous living areas, a versatile layout, and plenty of room to spread out, this home is designed to accommodate a variety of lifestyles. Whether you're hosting memorable gatherings or enjoying a quiet evening at home, this spacious Chesapeake property has room for it all.

732 Colonel Byrd Street, South Chesapeake
1025 Shore Road, South Chesapeake
$325,000
3 Beds ⋅ 1.1 Baths ⋅ 10654363 MLS
Come tour this ranch home with beautiful hardwood floors and a functional living space. This property has a partially open floor plan with a versatile layout. The open room space can be used to entertain, as an office, or as spare living space. The backyard is large and wooded, offering a storage shed and plenty of space for gardening and entertaining. The dishwasher, water heater, and refrigerator are all new (2025) and convey with the property.

1025 Shore Road, South Chesapeake
1209 Sir Galahad Drive, South Chesapeake
$359,000
3 Beds ⋅ 2 Baths ⋅ 10654313 MLS
Welcome to 1209 Sir Galahad! This beautifully updated one-owner home offers a comfortable, inviting flow with plenty of natural light throughout. Recent improvements include new LVP flooring, fresh paint, updated light fixtures, and a completely renovated primary bathroom. The kitchen features all-new GE appliances, quartz countertops, and new soft-close cabinetry. Tucked away on a quiet street in a mature, established neighborhood with convenient access to the interstate, this home offers the perfect combination of thoughtful updates, comfort, and accessibility.

1209 Sir Galahad Drive, South Chesapeake
100 Alice Street, South Chesapeake
$366,000
4 Beds ⋅ 2.1 Baths ⋅ 10653943 MLS
Welcome Home to Deep Creek! This beautifully renovated brick ranch offers 4 bedrooms, 2.5 baths, and an impressive list of brand-new updates. Step inside to discover brand-new gray carpet and luxury vinyl flooring throughout, complemented by fresh finishes that give the home a clean, modern feel. The updated kitchen features brand-new white cabinetry, a center island, granite countertops, and stainless steel appliances, creating a functional space for everyday living and entertaining. Both full bathrooms have been refreshed with brand-new ceramic marble tile in the showers for a polished, spa-inspired touch. And the updates continue beyond the interior! This home features a brand-new roof, HVAC system, and water heater, offering peace of mind for years to come. With two front and two back entry points, the layout also provides added flexibility for how you enter and use the home. Located in the desirable Deep Creek subdivision and just moments from the Gilmerton Bridge, this home offers convenient access to surrounding areas while providing the space and comfort of a brick ranch-style home. Four bedrooms. Two and a half baths. Brand-new major systems and finishes. Move-in ready. Come see all this home has to offer!

100 Alice Street, South Chesapeake
1101 Gauntlet Drive, South Chesapeake
$370,000
4 Beds ⋅ 2.1 Baths ⋅ 10653901 MLS
Welcome to 1101 Gauntlet Drive in Chesapeake! This spacious 4-bedroom 2.5-bath home offers approximately 1,824 square feet of comfortable living space. Step inside to a freshly painted interior featuring luxury vinyl plank flooring and an inviting living room with a cozy fireplace. The kitchen features white cabinetry, stainless steel appliances, a farmhouse-style sink, and plenty of workspace. Enjoy additional living and entertaining space in the Florida room overlooking the backyard. Upstairs, you’ll find generously sized bedrooms with great natural light. Stop here first! This is a wonderful opportunity to make this Chesapeake home your own!

1101 Gauntlet Drive, South Chesapeake
753 Willow Bend Drive, South Chesapeake
$389,900
4 Beds ⋅ 2 Baths ⋅ 10653770 MLS
Welcome home to this spacious 4-bedroom, 2-bath home offering a wonderful combination of comfort and open space. The inviting living room features vaulted ceilings, two skylights, and abundant natural light, creating a bright and open feel. The primary bedroom and bath are conveniently located on the main floor, along with main-level laundry for easy everyday living. One of the standout features is the very large second living room, featuring cathedral ceilings and lots of windows that fill the space with natural light while overlooking the backyard and pond. A 2-car attached garage provides plenty of room for parking and storage.

753 Willow Bend Drive, South Chesapeake
1128 Sir Galahad Drive, South Chesapeake
$357,000
3 Beds ⋅ 2.1 Baths ⋅ 10653187 MLS
This beautifully updated 3-bedroom, 3-bath home offers the perfect combination of comfort, style, and convenience. Ideally located near major commuter routes, shopping, dining, and entertainment, with easy access to Norfolk, Portsmouth, and Virginia Beach. Step inside to discover an inviting interior featuring modern flooring, a refreshed kitchen with stainless steel appliances, generous cabinet and counter space, a cozy fireplace, and spacious living and dining areas. Large glass doors fill the home with natural light and provide easy access to the backyard. The true showstopper? Your very own in-ground pool! The fenced backyard offers a wonderful space to relax, cool off on warm summer days, or entertain family and friends while enjoying the privacy of your outdoor retreat. With thoughtful updates, comfortable living spaces, and a backyard featuring a private pool, 1128 Sir Galahad Drive is a home you won't want to miss! Schedule your private showing today!

1128 Sir Galahad Drive, South Chesapeake
1333 Boxwood Drive, South Chesapeake
$349,000
3 Beds ⋅ 1.1 Baths ⋅ 10652758 MLS
Have you been searching for a home with a large garage and a no-tree lot? This is it. The kitchen has been completely renovated with a new gas stove, dishwasher, and refrigerator. A new mini-split system keeps the sun-filled Florida room (with its wall of windows) comfortable year-round. The oversized garage is a standout - wired with a 240V outlet, cooled by a window AC unit, and offering plenty of room for whatever organizing system you need. A small outdoor shed keeps lawn equipment tucked away, and the carport is a nice bonus.

1333 Boxwood Drive, South Chesapeake
1121 Sir Gawaine Drive, South Chesapeake
$344,900
4 Beds ⋅ 2 Baths ⋅ 10652250 MLS
Stunning four bedroom ranch with updates from top to bottom including a new roof, siding, trim, and exterior doors. The interior has been freshly painted and features new lighting, interior doors and hardware, and flooring throughout. The spacious living room and dining area flow seamlessly into the beautifully updated kitchen, complete with all new cabinetry, granite countertops, stainless steel appliances, and a large center island. Four generously sized bedrooms and two full bathrooms provide plenty of comfortable living space, with both bathrooms featuring updated vanities. Schedule your private tour today and come see all this beautifully updated home has to offer!

1121 Sir Gawaine Drive, South Chesapeake
1412 Sherbrooke Road, South Chesapeake
$499,900
4 Beds ⋅ 2.1 Baths ⋅ 10652040 MLS
Welcome to your dream Craftsman-style 4 bdrm 2 1/2 bath home w/a 2 car side loading garage nestled in Chesapeake. This meticulously crafted residence offers a perfect blend of modern convenience & classic charm promising a lifestyle of comfort & sophistication. The heart of the home lies in the gourmet kitchen adorned w/luxurious granite countertops & equipped with stainless steel appliances. Whether you're whipping up a culinary masterpiece or enjoying a casual meal at the breakfast bar, this culinary haven is sure to inspire your inner chef. As you venture outdoors, discover & enjoy your own oasis in the backyard waiting for your personal touch. You will enjoy easy access to local amenities, schools & major thoroughfares, ensuring that every convenience is w/in reach. Projected completion is December 2026. LVP flooring will be installed throughout the 1st floor. Photos from previous build. Make your appt today to see a previously built home.

1412 Sherbrooke Road, South Chesapeake
102 Ford Street, South Chesapeake
$250,000
2 Beds ⋅ 2.1 Baths ⋅ 10651883 MLS
Move-in ready! This 2-bedroom home offers a rare dual-ensuite layout — each bedroom has its own full bath, plus a powder room downstairs for guests. Brand-new LVP flooring and carpet, fresh paint throughout, and a new hot water heater. Kitchen and bath cabinetry has been freshly painted in a soft sage tone, paired with a brand-new stainless steel appliance package — refrigerator, range, dishwasher, and microwave hood. A new sliding glass door off the family room leads to a rebuilt rear landing and steps, and the HVAC condenser sits on a new stand. Seller to provide a clear termite/moisture report. Nestled in the established Fordville/Deep Creek area with easy access to shopping, dining, and I-64 — truly nothing to do but move in. Schedule your showing today!

102 Ford 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.

How much is your home worth?

Get instant property value now!