Chesapeake VA County Homes under $500,000

Welcome to Chesapeake, Virginia, a vibrant city nestled in the heart of the Tidewater region. Known for its rich history, diverse culture, and picturesque landscapes, Chesapeake offers a perfect blend of urban convenience and natural beauty. With its sprawling parks, serene waterways, and charming neighborhoods, this city is an ideal place for families, young professionals, and retirees alike.

Chesapeake boasts a variety of homes under $500,000, making it an attractive option for those looking to settle in a thriving community without breaking the bank. Whether you’re searching for a cozy single-family home, a modern townhouse, or a spacious property with room to grow, the real estate market in Chesapeake has something for everyone. Many of these homes feature contemporary designs, updated amenities, and lovely outdoor spaces, perfect for enjoying the mild Virginia climate.

One of the greatest advantages of living in Chesapeake is its strategic location. Residents benefit from easy access to major highways, making commutes to nearby cities like Norfolk and Virginia Beach a breeze. Additionally, Chesapeake is home to excellent schools, shopping centers, and recreational activities, ensuring that families have everything they need within reach.

If you’re considering a move to Chesapeake, you’ll find a welcoming community that values both tradition and progress. With homes under $500,000, this city provides an incredible opportunity to invest in a bright future. Explore the charm of Chesapeake, where every neighborhood has its unique character, and discover the perfect place to call home!

Newest Chesapeake VA County Homes under $500,000

$375,000

4 Beds ⋅ 3 Baths ⋅ 10656923 MLS

2406 Drum Creek Rd, Chesapeake VA 23321 is a 1,288-square-foot home built in 1962. A fireplace anchors the main living area, adding warmth and ambiance to the central gathering space. The primary bathroom includes double sinks for everyday convenience. Outdoors, a storage shed adds extra utility. This residence combines practical design with comfortable living spaces, delivering functional amenities throughout every room.

2406 Drum Creek Road, West Chesapeake

$415,900

3 Beds ⋅ 2.1 Baths ⋅ 10657874 MLS

Welcome to this beautifully maintained home in the highly sought after Cardinal Meadows neighborhood! A bright, open layout designed for comfortable everyday living and effortless entertaining. The kitchen features granite countertops, ample workspace, and flows seamlessly into the main living areas. Natural light throughout creates a warm and inviting atmosphere. Move-in ready and waiting for its new owners, this home offers the perfect combination of comfort, style, and functionality. Enjoy added privacy and peace of mind with a fully fenced backyard, featuring a low-maintenance vinyl privacy fence- perfect for pets, entertaining or relaxing outdoors.

1625 Redwing Arch, South Chesapeake

$197,500

3 Beds ⋅ 1.1 Baths ⋅ 10657866 MLS

Spacious 3-bedroom, 1.5-bath home in the heart of South Norfolk offering over 1,300 sq ft of living space. Property needs some TLC but presents tremendous potential for investors or buyers looking to build equity. Bring your vision and really make this home shine! Conveniently located near dining, shopping, the interstate, and more! Call today for more information and to schedule your tour!

710 B Street, Central Chesapeake

$379,900

4 Beds ⋅ 3.1 Baths ⋅ 10657809 MLS

Situated in Chesapeake's Norfolk Highlands neighborhood, this 4-bedroom, 3.5-bath home offers approximately 2,000 square feet with a flexible floor plan and plenty of indoor and outdoor space to enjoy! Step inside to find inviting living and dining areas that flow into an updated kitchen featuring granite countertops, shaker-style cabinetry, stainless steel appliances, and a center island with additional seating. The flexible floor plan features two bedrooms on the first floor, including one with a private ensuite bathroom, and two additional bedrooms upstairs, one also featuring its own ensuite bathroom. This layout offers great options for guests, home offices, or multigenerational living. Recent improvements include updated bathrooms (2024), plumbing (2021), and fresh interior paint. An encapsulated, unfinished basement offers additional storage or workspace. Out back, the fully fenced yard is ready for entertaining with an above-ground pool, multiple decks, and a separate man shed with power, a bar, and a window unit. Additional highlights include dual driveways, an electric vehicle charging station, and a roof replaced in 2020. 3.5 PERC ASSUMABLE VA LOAN!! Incentives may be available through preferred partners. Contact the listing agent for details and eligibility.

1129 Hazel Avenue, Central Chesapeake

$415,000

3 Beds ⋅ 2.1 Baths ⋅ 10657801 MLS

Welcome to 458 Blue Beech Way! This spacious 3-bedroom, 2.5-bath home offers a flexible floor plan with two primary suites—one conveniently located on the first floor and another upstairs. The living area features a cozy gas fireplace, while the generous walk-in attic provides abundant storage and potential for additional finished living space, subject to buyer verification and applicable approvals. Enjoy the amenities of this desirable community, including three scenic lakes with fountains, a community pool and clubhouse. Conveniently located near shopping, dining, entertainment and major roadways. This home offers comfort, flexibility and plenty of potential. Schedule your showing today

458 Blue Beech Way, South Chesapeake

$233,500

2 Beds ⋅ 2 Baths ⋅ 10657659 MLS

Low-maintenance living with a little poolside fun? Yes, please! Welcome to this beautifully maintained 2-bedroom, 2-bath condo in Chesapeake. Tucked away in a quiet corner location, this home offers comfortable living with the convenience of easy interstate access. Enjoy peace of mind with an HVAC system just 3 years old and a water heater only 1 year old. The community pool is included with the HOA, making it easy to enjoy a little fun in the sun without the upkeep. One assigned parking space plus plenty of visitor parking adds to the convenience. Well cared for and ready for its next chapter, this condo is a charming place to call home!

710 Rue Marseille, South Chesapeake

$380,000

3 Beds ⋅ 2 Baths ⋅ 10657636 MLS

Welcome to this beautifully maintained 3-bedroom, 2-bath ranch offering comfortable single-level living! This inviting home features hard-surface flooring throughout, a kitchen with new granite countertops, and a functional layout designed for everyday living. Step outside to enjoy the fully fenced backyard with privacy fencing, offering a wonderful space for outdoor entertaining, gardening, or simply relaxing. An attached one-car garage provides additional parking and storage. With thoughtful updates, easy maintenance, and desirable features throughout, this home offers the perfect combination of comfort and convenience!

1453 Debbs Lane, South Chesapeake

$499,900

4 Beds ⋅ 2 Baths ⋅ 10657378 MLS

Well maintained all brick ranch on a large .34 acre corner lot in the Hickory School District . Enter the large greatroom through foyer which opens to formal dining room. Greatroom features chairrail, wainscoating, exposed beams, built in bookcase and masonry wood burning fireplace.Kitchen has been updated with new cabinet faces, countertops and laminate floors; all appliances convey. Primary bath updated with new vanity, toilet and has tile floor. Hall bath updated with new toilet. Laundry closet convenietly off eat-in area in kitchen. Large frog has plenty of head space and large closet; partially floored walk in attic. HVAC, hot water heater newer, encapsulated crawl with dehumidifier. Large deck off greatroom. No neighborhood fees All Hikc

628 Gladesdale Drive, South Chesapeake

2112 Willow Point Arch, South Chesapeake

$240,000

2 Beds ⋅ 2 Baths ⋅ 10657769 MLS

Move-in ready 2-bedroom, 2-bath condo with spacious loft in the sought-after Riverwalk community! Freshly painted throughout with a new water heater and HVAC replaced in 2018. Bright, open floor plan features a kitchen overlooking the dining and living areas, creating a comfortable space for everyday living and entertaining. Generous first-floor bedroom offers a walk-in closet and direct access to a full bathroom. Upstairs features a versatile loft with built-ins and a spacious primary suite with ample closet space and private bath. Enjoy your own fenced front patio and additional storage shed. Conveniently located near shopping, restaurants, major highways, and military installations throughout Hampton Roads. Low-maintenance living, thoughtful updates, and an excellent location make this condo a fantastic opportunity. Schedule your showing now.

2112 Willow Point Arch, South Chesapeake

$489,900

4 Beds ⋅ 2 Baths ⋅ 10657404 MLS

Welcome to sought-after Riverwalk! This beautifully maintained 4-bedroom, 2-bath ranch sits on a desirable corner lot with great curb appeal. The freshly painted interior offers an inviting floor plan, vaulted ceilings, updated lighting, luxury vinyl plank flooring, and thoughtful custom touches, including enhanced closet space and added shelving. The kitchen features quartz countertops, stainless steel appliances, and two pantries. A versatile 4th bedroom/FROG above the 2-car garage offers flexible space for guests, an office, or hobbies. Enjoy the beautifully landscaped backyard with a deck and paver patio, perfect for outdoor entertaining. Riverwalk amenities include a clubhouse, pool, dock, boat ramp, playground, trails, tennis and pickleball courts, plus seasonal concerts and food trucks. Discover the charm, convenience, and lifestyle that make Riverwalk a wonderful place to call home!

443 Supplejack Court, South Chesapeake

$420,000

3 Beds ⋅ 2 Baths ⋅ 10657748 MLS

Welcome home to this charming, well-maintained ranch-style home in Chesapeake, VA! Offering move-in-ready, one-level living, this home features 3 spacious bedrooms, 2 full updated bathrooms, an updated eat-in kitchen with new appliances, and washer and dryer. The roof was replaced in 2021, providing added peace of mind. Outside, enjoy a large backyard with plenty of space for entertaining, pets, gardening, or relaxing. A detached garage provides additional storage or workshop space. Conveniently located near shopping, dining, everyday amenities, and major Hampton Roads interstates. If you're looking for a 3-bedroom ranch-style home for sale in Chesapeake, Virginia with an updated kitchen, detached garage, and spacious backyard, this home is a must-see. Schedule your private showing today!

908 Levee Court, South Chesapeake

$329,900

2 Beds ⋅ 2.1 Baths ⋅ 10657742 MLS

Welcome to Piney Grove, an exquisite community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This 2-level plan beautifully showcases an open floorplan w/ luxurious upgrades. The kitchen stuns guests w/ upgraded quartz countertops, subway tile backsplash, cabinet crown molding & soft-close drawers. Easily maintained & durable LVP flooring 1st level, baths, & laundry. Crown molding throughout entire 1st level. Lighted tray ceiling in primary bedroom. WIC's in both bedrooms. Quartz vanity in primary bath w/ shower. Enjoy a view of the surrounding woods & exceptional community amenities, including stet-of-the-art clubhouse & sparkling pool, great for relaxation & socializing. Discover your new home today! Call agent to schedule an appointment & to take advantage of pre-opening special pricing!

4995 Boone Road Unit 8, West 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.