West Chesapeake Homes under $500,000

Welcome to West Chesapeake, Virginia—a vibrant community that perfectly blends suburban charm with urban convenience. Nestled in the heart of Chesapeake County, this delightful area offers residents a unique lifestyle characterized by its friendly atmosphere, scenic parks, and rich history. West Chesapeake is known for its family-oriented environment, making it an ideal place for individuals and families alike to call home.

One of the standout features of West Chesapeake is its affordability. With a selection of beautiful homes priced under $500,000, it provides an exceptional opportunity for first-time homebuyers, growing families, or anyone looking to invest in a property without breaking the bank. These homes come in various styles, from cozy single-family residences to modern townhouses, ensuring that there’s something for everyone.

West Chesapeake’s real estate market is thriving, and the homes in this price range are often characterized by spacious layouts, inviting backyards, and proximity to local amenities. Residents enjoy easy access to top-rated schools, shopping centers, and recreational areas, making it a convenient choice for daily living.

Moreover, the community is well-connected to major highways, allowing for seamless commutes to nearby cities and attractions. Whether you’re exploring the lush parks, indulging in local dining, or participating in community events, West Chesapeake offers a lifestyle filled with opportunities and warmth.

Discover your dream home in West Chesapeake today, where comfort meets affordability, and a welcoming community awaits you!

Newest West Chesapeake Homes under $500,000

$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

$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

$489,000

4 Beds ⋅ 2.1 Baths ⋅ 10655779 MLS

This beautifully maintained home that offers the look and feel of new construction. . . without the wait! Thoughtfully upgraded with custom finishes throughout, this home perfectly blends modern style with everyday comfort. Step inside to discover an open, light-filled floor plan featuring a stunning custom accent wall that adds warmth and character to the main living space. The spacious kitchen flows seamlessly into the dining and living areas for entertaining or spending time with family. Retreat to the generously sized bedrooms, each offering plenty of space for relaxation, a home office, or growing families. The primary suite provides a peaceful escape with exceptional closet space and a well-appointed ensuite bath. Conveniently located near shopping, dining, schools, and major highways. Schedule your private showing today!

539 Schaefer Avenue, Chesapeake

$199,900

3 Beds ⋅ 1 Baths ⋅ 10655489 MLS

Rare package deal opportunity in highly sought-after Western Branch! This move-in ready 3-bedroom ranch sits on a quiet street. The home has new paint, new floors, new A/C & heat systems, new wrap around porch, newer appliances and windows. The large rear yard and side lot provide an abundance of space for storing an RV, boat, or multiple extra cars. Nestled in a quiet neighborhood just minutes from local shopping, parks, schools, and military bases. No HOA. Additional lot next door can be purchased as well at 4999 Clifton St.

5001 Clifton Street, Chesapeake

$425,000

3 Beds ⋅ 2 Baths ⋅ 10655209 MLS

Welcome home to this single-story masterpiece offering high-end designer finishes & modern elegance from top to bottom. Step inside to the seamless open flow accented by recessed lighting, modern light fixtures, stylish ceiling fans, & durable Luxury Vinyl Plank (LVP) flooring throughout the main living spaces. The chef-inspired kitchen features pristine quartz countertops, a custom tile backsplash, brand-new stainless steel appliances, & soft-close shaker cabinetry. Both bathrooms feature artistic custom tile work surrounding the tub & shower, elevated by high-end fixtures & vanity details. All 3 bedrooms feature fresh plush carpet for maximum comfort. Outdoors, enjoy an expansive, private backyard complete w/ a custom deck for entertaining, an extended driveway, & additional concrete pad—great for extra vehicle parking or outdoor storage setup. Located in a top-tier school district & just minutes from premier shopping, dining, & retail options. Nothing left to do but move right in!

2821 Meadow Wood Dr E Drive, Chesapeake

$359,900

4 Beds ⋅ 2 Baths ⋅ 10654830 MLS

Come check out this DIAMOND IN THE ROUGH. House is in need of updating and priced accordingly. But the BONES TO THE HOUSE ARE GOOD. NEW ROOF (2023), 1 out of 2 AC UNITS NEW (2025). (and the other AC unit has been RECENTLY SERVICED). Unique floor plan with an area that could serve as an IN LAW SUITE, a QUIET NEIGHBORHOOD and a GOOD SCHOOL SYSTEM. LARGE CORNER LOT. Close to shopping, food, and the interstate. PRIVATE BACKYARD with a deck and an additional storage shed.

2600 Janson Drive, Chesapeake

$150,000

2 Beds ⋅ 2 Baths ⋅ 10655093 MLS

Get the movers ready! 2-bedroom, 2-bath condo in a highly desired location with easy access to I-664 for a quick commute. Conveniently located near shopping, grocery stores, restaurants, and everyday amenities. Fresh paint and new carpet throughout create a bright, welcoming atmosphere. The spacious living area features a cozy wood-burning fireplace, perfect for relaxing evenings at home. Exceptionally clean!! Enjoy affordable low-maintenance living in a location that puts everything within reach. A wonderful opportunity for first-time buyers, downsizers, or anyone seeking comfort, convenience, and value.

3418 Clover Road, Chesapeake

4332 Hillingdon Bend Unit 206, Chesapeake

$227,000

2 Beds ⋅ 2 Baths ⋅ 10653350 MLS

Welcome home! This beautiful residence features an open floor plan and soaring nine-foot ceilings. The layout includes two bedrooms and two full bathrooms, highlighted by a primary suite with dual closets. The kitchen is equipped with stainless steel appliances and ample cabinetry, flowing seamlessly into the main living and dining areas. Additional interior features include central air conditioning, forced air heating, and dedicated washer and dryer hookups. As part of a common-interest community, this property offers one assigned parking space and access to shared amenities, including a swimming pool, grounds maintenance, and trash removal. Conveniently located near major highways, military bases, local shipyards, and the retail options surrounding Chesapeake Square, this home is perfectly positioned. Call today to schedule your private showing!

4332 Hillingdon Bend Unit 206, Chesapeake

$435,000

4 Beds ⋅ 2.1 Baths ⋅ 10654524 MLS

Welcome to this charming 4 bedroom, 2.5 bathroom home nestled in the sought after Western Branch area of Chesapeake! As you step inside, you'll be greeted by luxurious LVP flooring that flows gracefully throughout majority of the first floor. The kitchen has been tastefully upgraded with brand new tile and features convenient bar seating, perfect for casual meals and entertaining. With sliding doors leading to the fenced-in backyard, the open living area is filled with natural light and offers a seamless transition between indoor and outdoor spaces. Freshly painted walls throughout the home provide a crisp backdrop for your personal touches. This home enjoys a prime location with easy access to neighborhood schools and I-664. Don't miss the opportunity to make this immaculate residence your new haven!

5207 Pughsville Road, Chesapeake

$355,000

3 Beds ⋅ 2 Baths ⋅ 10654393 MLS

There's plenty of opportunity to create your own vision with this all brick, 3 bedroom, 2 bath house in Western Branch. The interior was renovated 4 years ago with a roof replacement 2022, refrigerator 2022, primary bath renovated 2022 as some of the upgrades. With a large backyard, spacious deck and both attached and detached garages, there's plenty of space to entertain. Make sure to add this one to the list!

4109 Taylor Road, Chesapeake

$280,693

3 Beds ⋅ 1.1 Baths ⋅ 10654356 MLS

Solid rancher on a crawl space. Three bedrooms and one and a half baths. Newly installed vinyl plank flooring. Spacious living room. Eat in kitchen with solid wood cabinets and utility closet. Brick exterior with vinyl siding accents. Double paned windows. Fenced backyard. Driveway parking. Shed.

3228 Bangor Drive, Chesapeake

$384,000

3 Beds ⋅ 2 Baths ⋅ 10654099 MLS

Rare GEM in the Western Branch school district! This meticulously maintained brick ranch was renovated in 2021 and offers 3 bedrooms, 2 baths, and a functional floor plan with spacious living and dining rooms, a sunken family room, good-sized bedrooms, and a primary bedroom with a private bath. Features include newer LVP flooring, modern updated bathrooms, and a stylish kitchen with granite countertops, stainless steel appliances, and newer cabinets. Two wood-burning fireplaces have been maintained and used during winter. Enjoy the screened-in back porch, large backyard, and wooded views. Major improvements include a new roof ('21), new hot-water heater tank and gutters ('26). Two parcels total approximately 0.78 acre: a 0.45-acre homesite and a rear parcel of approximately 0.33 acre. Attached 1-car garage with ample room to expand parking. NO HOA! Move-in ready and close to bases, interstates, shopping, and restaurants. Schedule your showing today!

2924 Taylor Road, 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.