Chesapeake Homes under $500,000

Welcome to Chesapeake, Virginia—a vibrant city that beautifully blends suburban charm with urban conveniences. Nestled in the heart of Hampton Roads, Chesapeake is known for its picturesque landscapes, rich history, and a plethora of recreational opportunities. With over 22 miles of waterfront along the Elizabeth River and the Intracoastal Waterway, residents enjoy a lifestyle filled with outdoor activities, from boating and fishing to hiking in the lush parks that dot the area.

Chesapeake boasts a diverse array of neighborhoods, each offering its own unique character and community spirit. Whether you’re drawn to the bustling atmosphere of Greenbrier or the serene appeal of Great Bridge, there’s something for everyone. The city is also home to top-rated schools, making it an ideal choice for families.

If you’re in the market for a home, you’ll be pleased to discover that Chesapeake offers a variety of properties under $500,000. From charming single-family homes to modern townhouses, there are plenty of options that cater to different lifestyles and budgets. These homes often feature spacious layouts, contemporary finishes, and access to community amenities, making them perfect for first-time buyers or those looking to downsize.

With its friendly atmosphere, excellent amenities, and affordable housing options, Chesapeake is not just a place to live; it’s a place to thrive. Come explore this wonderful city and find your dream home today!

Newest Chesapeake Homes under $500,000

$459,900

4 Beds ⋅ 2 Baths ⋅ 10656377 MLS

Welcome to this spacious 4-bed, 2-bath home situated on a beautiful half-acre lot in the heart of Great Bridge! Offering a flexible floor plan, this home features 2 oversized living areas, 2 spacious primary bedrooms, & 2 additional bedrooms—ideal for multigenerational living, a home office, playroom, or the potential for a 5th bedroom. Updates include fresh interior paint, new flooring, restored hardwood floors, & renovated bathrooms. The updated kitchen offers new countertops, ample cabinet space, & a cozy breakfast nook. Step outside to the covered deck overlooking the expansive backyard, providing plenty of room for entertainment, gardening, pets, or future outdoor additions. With no HOA, you’ll also enjoy plenty of space to park your RV or boat on the property. Located in the highly desirable Great Bridge school district, you’ll enjoy the convenience of being just minutes from shopping, restaurants, & everyday amenities. Don’t miss this rare opportunity to own a move-in-ready home with space, flexibility, & an unbeatable location. Schedule your showing today!

145 Hurdle Drive, Chesapeake

$479,972

3 Beds ⋅ 2.1 Baths ⋅ 10656369 MLS

Move right in to this beautifully maintained home, built in 2016 and perfectly situated on over ¾ of an acre at the end of a quiet cul-de-sac. Designed with both comfort and entertaining in mind, this home features 9-foot ceilings, an open-concept floor plan, quartz countertops, and stainless steel appliances. Upstairs, you’ll find a convenient laundry room with washer and dryer that convey. The expansive backyard offers endless possibilities, with plenty of room to add a pool, garden, or outdoor living space—all enhanced by attractive fencing.Enjoy a tucked-away, private setting while still being just minutes from shopping, interstates, and military bases. This home truly offers the best of space, style, and location. Attractive financing using the Seller's preferred lender . Be sure to inquire.

1121 Kinderly Lane, Chesapeake

$465,000

3 Beds ⋅ 2 Baths ⋅ 10656198 MLS

Step into this beautifully maintained ranch-style home that blends comfort, convenience, and charm. Featuring updated bathrooms and a modern kitchen with stylish finishes, this home is ready for you to move right in. Enjoy the spacious large open yard perfect for gatherings, gardening, or simply relaxing surrounded by a newer upgraded wooden privacy fence for peace and seclusion. The screened-in porch offers a cozy spot to unwind year-round, while those who work from home or need a creative space, there is an outdoor office with electric and AC to ensure comfort and productivity. Schedule your showing today.

729 Mount Pleasant Road, Chesapeake

$350,000

3 Beds ⋅ 2 Baths ⋅ 10656240 MLS

Welcome home to this inviting 3 bdrm, 2 full bath plus a bonus room that can be used as an office, nursery, craft room or guest room. This ranch offers comfortable and spacious one-level living. Beautiful wood floors add warmth and character throughout the home. The kitchen features attractive granite countertops with a large breakfast bar, providing both style and functionality for everyday living and entertaining.The thoughtfully designed floor plan offers comfortable living spaces, well-proportioned bedrooms, extra large primary bedroom and the convenience of single story living. Enjoy the large yard and detached garage with carport. Whether you are a first-time homebuyer, downsizing, or simply looking for the convenience of ranch-style living, this home is ready to welcome you. Conveniently located near major military installations, naval shipyards, and employment centers throughout Hampton Roads, making it an excellent location for military personnel, contractors, and commuters.

3210 Indigo Road, Chesapeake

$415,000

3 Beds ⋅ 2.1 Baths ⋅ 10656271 MLS

This move-in-ready, 3-bedroom, 2.5-bath features recently installed carpet throughout, and a new dishwasher. The open-concept layout flows between the kitchen, dining, and living areas, creating a space for daily living and entertaining. Generously sized rooms offer flexibility for furniture placement, while deep closets and storage help with organization. The kitchen features soft-close drawers, granite countertops, a custom backsplash, and an island with accent lighting. Upstairs, the primary suite offers a walk-in closet, double vanities, and a walk-in shower with dual shower heads. The hall bath also features double vanities and direct access from the second bedroom. The attached garage and fenced backyard patio provide an ease with daily living. Enjoy local shopping and dining along with outdoor recreation at Great Bridge Lock Park along the Intracoastal Waterway. Nearby commuter routes connect you to military bases and destinations throughout the area.

308 Sikeston Lane, Chesapeake

$370,000

3 Beds ⋅ 2 Baths ⋅ 10656177 MLS

Welcome home to this beautifully updated and well kept 3 bedroom, 2 bath home tucked away on a quiet dead end street in a welcoming, close knit community. Step inside to find an updated, spacious kitchen with plenty of room for cooking, entertaining, and everyday living. The primary suite offers a private retreat featuring a large en suite bathroom with a double vanity sink, Jacuzzi tub, separate shower, and walk in closet. Outside, enjoy a fully fenced backyard with plenty of space to relax, entertain, or play. A two car garage provides additional parking and storage. With modern updates throughout, generous living spaces, and a peaceful neighborhood setting, this home is truly move-in ready and waiting for its next owner.

5008 James Street, Chesapeake

$489,900

4 Beds ⋅ 2 Baths ⋅ 10656242 MLS

Charming ranch with large backyard and pool! Enjoy the welcoming front porch before heading inside to the thoughtfully updated interior, where fresh paint and beautiful new LVP flooring create a bright, inviting atmosphere. New carpet in the room above the garage adds comfort and versatility to the home's flexible living space. Designed for both everyday living and effortless entertaining, the home features a living room, dining room, and a cozy family room accented by wood beams and a fireplace. At the heart of the home, the eat-in kitchen offers all new sleek cabinetry, granite countertops, and stainless steel appliances. Four spacious bedrooms provide comfortable accommodations, while both full bathrooms have been refreshed with stylish new vanities. Outside, you're sure to enjoy the fully fenced backyard featuring a spacious deck overlooking the swimming pool creating an inviting setting for relaxing, entertaining, or enjoying warm summer days. Two storage sheds provide additional room for lawn equipment, tools, or hobbies, while the attached garage adds everyday convenience and extra storage.

403 Caravelle Court N, Chesapeake

713 Rapidan River Court Unit G, Chesapeake

$230,000

2 Beds ⋅ 2 Baths ⋅ 10655996 MLS

Freshly transformed and move-in ready! This second-floor corner end-unit condo in Chesapeake's Riverwalk community just had a full cosmetic refresh of the interior, including fresh paint throughout, an updated kitchen, new flooring and more. The single-level layout offers 2 bedrooms and 2 full baths. A wood-burning fireplace anchors the living area, and a private balcony overlooks mature trees. The primary suite has its own full bath. Beyond the cosmetic work, the home also has newer windows and a newer HVAC system. Kitchen appliances convey along with an exterior storage shed and two assigned parking spaces. The condo fee includes water, trash, grounds maintenance, the community pool and clubhouse.

713 Rapidan River Court Unit G, Chesapeake

1005 Winged Foot Court Unit B, Chesapeake

$335,000

3 Beds ⋅ 2.1 Baths ⋅ 10656159 MLS

Welcome Home to this charming twin Home style Condo in Greenbrier's Fairways Villas. Tucked away in the cul-de-sac with garage, driveway, and communal parking, low maintenance living meets style and convenience. Enter into your inviting foyer greeted with LVP floors and neutral paint. Layout features large open concept great room and dining area. Eat-in kitchen is spacious with granite tops and stainless appliances. Access to one car garage and laundry off kitchen and half bath for the ultimate first floor layout. Second level features large primary bedroom with ensuite bath and walk in closet. Bedroom features natural light and vaulted ceilings. Two large spare bedrooms and hall bathroom complete this ideal layout. Large slider leads to rear deck which is large and tranquil backing up to golf course views. Newer HVAC & water heater 2021 and replacement windows. Call this Home Today!

1005 Winged Foot Court Unit B, 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

$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

$499,999

3 Beds ⋅ 3 Baths ⋅ 10656063 MLS

Welcome home to Chesapeake’s premier 55+ community! This move-in-ready home offers a fantastic and flexible floor plan featuring TWO spacious primary suites—one on each level—providing plenty of room for guests. The beautiful family room features soaring vaulted ceilings, luxury vinyl plank flooring, and a cozy gas fireplace. Just off the main living area is an additional first-floor flex space, perfect for a home office, reading room, or a relaxing spot to enjoy your morning coffee. The spacious eat-in kitchen features new stainless steel appliances and recessed lighting, while the formal dining room provides the perfect space for entertaining. The large first-floor primary suite offers a private bath with double vanity, separate shower, and oversized jetted tub. At the heart of the community is the Bay Club, featuring indoor and outdoor pools, hot tub, fitness center, billiards, library, game rooms, and so much more. Come experience resort-style living at Eagle Pointe!

1407 Hawick Terrace, 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.