Chesapeake Homes for Sale

Welcome to Chesapeake, Virginia—a vibrant city that beautifully blends suburban charm with urban convenience. Nestled in the heart of Hampton Roads, Chesapeake is known for its lush landscapes, rich history, and a strong sense of community. With over 350 miles of navigable waterways, this city is a paradise for boating enthusiasts, offering endless opportunities for fishing, kayaking, and enjoying the serene beauty of nature.

Chesapeake is home to a diverse population and a variety of amenities, including top-rated schools, shopping centers, and recreational parks. Whether you’re exploring the scenic Dismal Swamp Canal or enjoying a family day at the Chesapeake City Park, there's something for everyone in this welcoming city. The local dining scene is equally impressive, featuring everything from cozy cafes to fine dining establishments that celebrate the region's culinary heritage.

If you’re considering making Chesapeake your home, you’ll be pleased to know there are a variety of homes for sale to suit every lifestyle. From charming single-family houses in friendly neighborhoods to modern townhomes with all the latest amenities, the real estate market in Chesapeake offers something for everyone. Many properties boast spacious yards, perfect for family gatherings or quiet evenings under the stars.

With its perfect blend of nature, community spirit, and convenient access to nearby cities, Chesapeake is more than just a place to live; it’s a place to thrive. Explore our listings today and discover the perfect home in this delightful city!

Newest Chesapeake Homes for Sale

$575,000

4 Beds ⋅ 3 Baths ⋅ 10656145 MLS

WESTERN BRANCH HOME WITH A DETACHED 2-CAR GARAGE, SPACIOUS FENCED YARD, AND FLEXIBLE LIVING SPACE! Welcome to 2044 Columbo Avenue, set on a generous .34-acre lot in Chesapeake’s Western Branch area. This well-maintained home is an excellent fit for buyers who need room for vehicles, tools, hobbies, storage, a home business setup, or recreational equipment. In addition to the attached 1-car garage, the property offers an oversized detached 2-car garage with a finished second floor. Built approximately 2009, it includes insulation, drywall, electrical, and a Wi-Fi-controlled mini-split HVAC system—ideal for a workshop, office, studio, recreation room, hobby space, or conditioned storage. Inside, the kitchen features granite countertops, black stainless appliances, a breakfast bar, and an open connection to the great room for easy everyday living and entertaining. A formal dining room, first-floor flex room, full bath, and enlarged laundry room add valuable versatility. Upstairs, the spacious FROG serves as the fourth bedroom with a full bath nearby, while the primary suite includes a refreshed bath. Recent improvements include a Trane dual-zone Wi-Fi HVAC system approximately four months old, vinyl siding, metal exterior wrap, newer front and sliding rear doors, screened porch, LVP/laminate flooring, rear windows, and gutters. Natural gas serves the heat and hot water. Enjoy the large fenced backyard with a deck, screened porch/patio, and hot tub—plenty of room to relax, entertain, play, garden, or let pets roam. Convenient to I-664, military installations, tunnels, shopping, dining, and destinations throughout Hampton Roads.

2044 Columbo Avenue, Chesapeake

$695,000

4 Beds ⋅ 3.1 Baths ⋅ 10656163 MLS

Your own private retreat in the heart of Cheshire Forest! This beautifully maintained 4 bedroom, 3.5 bath home offers over 3,100 sq ft with a floor plan made for everyday living and entertaining. Inside, enjoy gorgeous oak floors, an updated open concept kitchen, formal living and dining rooms, a sun-filled family room with fireplace, and a spacious primary suite with its own fireplace. Outside is where this home truly shines; take a dip in the heated in-ground pool, relax on the deck, or unwind in your private, fully fenced backyard. An impressive list of improvements includes a new pool liner (2025), upstairs A/C (2024), refinished hardwood floors, updated roof, gutters, garage door, HVAC, water heater and more. Two-car garage plus Cheshire Forest amenities including a clubhouse, community pool, playground and tennis courts. A rare combination of space, updates and resort-style living in Great Bridge!

801 Keeling Drive Drive, Chesapeake

317 George Washington Highway S, Chesapeake

$524,900

3 Beds ⋅ 2 Baths ⋅ 10655769 MLS

Five acres. A powered detached workshop. Room to breathe, space to make your own. This updated Cape Cod offers the flexibility of acreage living in Chesapeake’s Grassfield area. The home features 3 bedrooms, 2 full baths and a first-floor bedroom and full bath. MLS square footage reflects 1,869 sq. ft. per tax records; a recent appraisal measured approximately 2,067 sq. ft.Updates include a renovated kitchen and baths, replacement windows, updated electrical and plumbing, a 2023 heat pump, 2024 whole-house paint and newer flooring. Beautiful hardwood floors, a fireplace, and generous mud/laundry space add function and character. The approx. 736 sq. ft. powered detached garage/workshop offers room for tools, projects, and storage. Gorgeous outdoors boast a fenced yard area, wooded acreage, mature fruit and fig trees, enclosed porch, deck and patio. City water/sewer add convenience. Recent appraisal at $600,000! Existing VA loan may be assumable, reach out to listing agent for more details.

317 George Washington Highway S, Chesapeake

$450,000

3 Beds ⋅ 2.1 Baths ⋅ 10655125 MLS

Imagine coming home to a peaceful cul-de-sac tucked away just minutes from everything Greenbrier has to offer. The nearby city park is wonderful for a quick bike ride or leisurely stroll, while restaurants, shopping, and entertainment at Summit Pointe are just minutes away.This home offers the best of both worlds... the privacy and peacefulness of your own backyard while keeping you close to the places you want to go and the things you love to do. Enjoy the feeling of a quiet retreat without giving up convenience or connection.Don't miss your opportunity to make this move in ready Greenbrier gem your next home. Schedule your showing today!

621 Windward Drive, Chesapeake

$575,000

4 Beds ⋅ 3 Baths ⋅ 10656015 MLS

Welcome to 423 Las Gaviotas Blvd., located in the desirable Las Gaviotas golf course community. Situated directly on the golf course, this 4-bedroom, 3-bath home offers approximately 2,585 square feet of living space and a spacious, versatile floor plan, with crown molding throughout. In-ground sprinkler system. Enjoy golf course views and the opportunity to personalize the home with your own finishes and style. Generous living areas provide plenty of space for everyday living and entertaining. Conveniently located in an established Chesapeake community, this property offers a wonderful combination of space, location, and possibilities. Motivated seller—schedule your private showing today!

423 Las Gaviotas Boulevard, Chesapeake

$310,000

3 Beds ⋅ 1 Baths ⋅ 10655713 MLS

Welcome home to this cute little ranch that perfectly blends comfort, charm, and convenience! This move-in-ready home offers easy one-level living with a welcoming layout and a warm, inviting feel throughout. Whether you're a first-time buyer, downsizing, or simply looking for a home that's easy to love and easy to maintain, this one is worth a look.Enjoy the convenience of being just minutes from major highways, making commuting and getting around Hampton Roads a breeze. When it's time to slow down and enjoy the outdoors, you'll appreciate having a beautiful nearby park and walking areas close to home. It's the perfect setting for an evening stroll, morning walk, or simply enjoying some fresh air.

4316 Taylor Road, Chesapeake

$289,900

3 Beds ⋅ 1.1 Baths ⋅ 10656065 MLS

Don’t miss this charming brick starter home offering 3 bedrooms, 1.5 baths, and just under 1,200 sq. ft. The updated kitchen, newer roof, HVAC, and windows (all under 5 years old) provide peace of mind, while the fully fenced backyard offers plenty of space to relax or play. Conveniently located near interstates, military bases, shopping, and restaurants, and zoned for Indian River schools. A great opportunity to add your personal touches and make it your own!

718 Osborn Avenue, Chesapeake

$429,900

3 Beds ⋅ 2 Baths ⋅ 10655782 MLS

Welcome to 109 Causeway Dr, a charming home nestled on a quiet street in the highly desirable Great Bridge area of Chesapeake! Enjoy major peace of mind with recent big-ticket upgrades, including a newly updated HVAC system, new water heaters, flooring throughout, and the electrical panel in the garage updated within the last 2 years. One of the standout features of this property is the HUGE backyard—providing an abundance of open space for entertaining, gardening, or play. Plus, there is ample parking and side access with more than enough space to park your large RV, boat, trailer, or multiple vehicles. Location is everything! Situated just off Battlefield Blvd, you are minutes away from top-rated Chesapeake public schools, local parks, waterways, and the Intracoastal Waterway. You'll love the convenience of quick access to everyday shopping, dining, medical facilities, and major highways for an easy commute throughout Hampton Roads.

109 Causeway Drive, Chesapeake

$475,000

4 Beds ⋅ 2 Baths ⋅ 10655999 MLS

Escape to your own private waterfront retreat on nearly 1/2 acre in the sought-after Inland Colony community, where peaceful wooded surroundings and serene water views create the perfect connection to nature. This 2,494 sq. ft. home offers 4 bedrooms, 2 baths, a first-floor primary suite, detached ADU, 1-car garage, and private dock with access to the Intracoastal Waterway on the Elizabeth River. Enjoy the expansive deck overlooking the backyard and water or unwind on the screened porch off the primary suite. Fresh paint and new carpet enhance the bedrooms, while the spacious kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and generous prep space. French doors open from the dining room to the living area, creating an ideal layout for entertaining. The FROG with new carpet and large walk-in attic provide excellent flexibility and storage. Some photos may be virtually staged. Conveniently located near shopping, dining, top-rated schools, and interstate access while offering a true waterfront escape.

1145 Sunlight Drive, Chesapeake

$950,000

4 Beds ⋅ 3.1 Baths ⋅ 10655919 MLS

Your dream home awaits!! Craftsman bones, a custom remodel, and a horse barn out back: acreage living with refined character. Every inch of this home was designed by the sellers who were contractors with love over the years. Inside, coffered ceilings meet warm cedar and wood-plank ceilings, giving every room a crafted, finished feel, and Brazilian cherry hardwoods run underfoot toward a stone gas-log fireplace that anchors the living space. Floor-to-ceiling windows and skylights flood the home with light, while custom barn doors and Restoration Hardware fixtures make even the transitions between rooms feel intentional. The kitchen is built to gather around. An oversized honed granite island with a built-in microwave takes center stage, backed by custom cabinetry, an etched tile backsplash, a built-in pantry, newer appliances, and purified water at the sink. Next door, color-changing upper lighting lets the dining room shift from weeknight dinner to late-night celebration at the flip of a switch. The first-floor and second story primary suite comes with its own bath, the bathrooms have been updated throughout, and a sun room, bar and mudroom with drop zone give the layout room to breathe. Then step outside, where the property really shows off. A 40,000-gallon saltwater pool, 8 feet deep with a diving board and fountain, sits beside a koi pond and gazebo linked by brick walkways. Made for a party or a wedding. Beyond it, a fenced acre of pasture leads to a barn with two stalls, a wash stall, a brick-paved breezeway, tack room, and horses are allowed. Wrapped in Hardie plank and stone, heated and cooled by geothermal, and tucked into a wooded setting of nearly five acres neighboring Greenbrier Farms in the Hickory school zone. Morning coffee in the sun room, afternoons at the barn, evenings by the pool: this home makes every part of the day worth staying for. And let's talk privacy.

241 Sign Pine Road, Chesapeake

$640,000

5 Beds ⋅ 2.1 Baths ⋅ 10655665 MLS

Welcome home to 1103 Madison Lynn Way in Chesapeake! Located in the sought-after Hanbury Manor community and Great Bridge School District, this spacious 5-bedroom, 2.5-bath home offers approximately 2,557 square feet with a bright, open layout designed for everyday living and entertaining. The main level features an inviting living area, dedicated dining space, and a first-floor bedroom ideal for guests, a home office, or flex space. The updated kitchen features quartz countertops, stainless steel appliances, ample cabinetry, and LVP flooring. Upstairs, you’ll find four additional bedrooms, including a spacious primary suite with cathedral ceilings, a walk-in closet, and ensuite bath with a soaking tub and separate walk-in shower, along with a dedicated laundry room with a utility sink. Outside, enjoy a fully fenced backyard with a patio and storage shed, plus an attached two-car garage. With no HOA and a convenient location near Great Bridge schools, shopping, dining, and interstate access, this home offers the space, updates, and location you’ve been looking for!

1103 Madison Lynn Way, Chesapeake

$655,000

3 Beds ⋅ 3.1 Baths ⋅ 10655918 MLS

This SHOWCASE home can be yours - MOVE IN READY! Award-winning builder blends elegance and easy living w/all grounds maintained! Exceptional details - Custom lighting throughout, Designer wallpaper, Culinary bar, White oak beams and more, and Matte White GE Cafe appliances w/Brushed Brass. French doors open to custom 12x30 paver w/fenced yard. HW throughout first floor, first floor BR with full bath, tiled shower, first-floor laundry (and full laundry up). Upstairs HW flooring in Up Hall, Loft and Primary BR. Loft with custom bar for relaxing evenings. Stunning primary BR with 10'x13' custom walk-in closet and 2 finished closets 10'x5' finished storage closets. Spa-inspired bath with 9' vanity, WOW shower, free-standing tub, champagne ready. Professionally managed community.

200 Traditions Way, Chesapeake

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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.