Chesterfield Homes under $500,000

Welcome to Chesterfield, Virginia – a vibrant community that perfectly blends suburban charm with urban convenience. Nestled just south of Richmond, Chesterfield boasts a rich history, stunning landscapes, and a welcoming atmosphere that makes it an ideal place to call home. With its picturesque parks, top-rated schools, and a plethora of shopping and dining options, it’s no wonder that Chesterfield is a sought-after destination for families and professionals alike.

One of the most appealing aspects of Chesterfield is the diverse range of homes available, especially for those looking to invest in properties under $500,000. Whether you’re a first-time homebuyer or looking to downsize, Chesterfield offers a variety of options that cater to different lifestyles and preferences. From charming single-family homes with spacious yards to modern townhouses nestled in friendly neighborhoods, there’s something for everyone.

Imagine starting your day with a stroll through one of Chesterfield’s beautiful parks or enjoying a weekend at the local farmer’s market. With its strong sense of community and numerous recreational activities, residents enjoy a high quality of life. The area is also well-connected, making commuting to Richmond and beyond a breeze.

If you’re searching for a place that combines affordability with a rich array of amenities, Chesterfield, VA, is the perfect choice. Explore the homes available under $500,000 and discover how you can become part of this wonderful community. Your dream home in Chesterfield awaits!

Newest Chesterfield Homes under $500,000

$260,000

3 Beds ⋅ 2 Baths ⋅ CVR-2627091 MLS

Welcome home! This beautifully completely remodeled 3-bedroom, 1.5-bath home offers modern comfort, style, and convenience with all the work already done for you. Step inside to a bright open-concept living area, featuring a spacious great room that flows seamlessly into the kitchen—perfect for entertaining, family gatherings, or everyday living. The home has been thoughtfully updated from top to bottom with new flooring, fresh paint, new siding, new cabinets, new appliances, updated bathrooms, and a new heat pump. Enjoy peace of mind with a NEW ROOF, plus a new deck and welcoming front porch that provide great outdoor spaces for relaxing and enjoying the large yard. With extensive renovations already completed, this home is truly move-in ready. Just bring your belongings and make it your own! 3 Bedrooms | 1.5 Baths | Open Concept | Completely Remodeled | Large Yard | Move-In Ready

21108 Matoaca Road, Chesterfield

$376,950

3 Beds ⋅ 2 Baths ⋅ CVR-2627074 MLS

Lovely neighborhood of well cared for brick ranchers, this one is a true gem. Almost an acre lot (rear lot extends well beyond the fencing, marked in rear with red flag) this immaculate home has formal liv and dining and separate fam rm. Many upgrades including hardwood floors, new carpet in fam room, brick fireplace with gas logs, pull down attic, insulated and floored end to end, encapsulated crawl space with dehumidifier and water filtration system, recently painted interior, upgraded tile shower in primary ensuite, extra large deck for entertaining, vinyl replacement windows, gutters and leaf guards. Very large exterior workshop/building with electricity, this building is even covered under the yearly termite bonding program. All appliances are functioning properly but please include in contract: THE FOLLOWING CONVEYS "AS IS" Washer, Dryer, SS Refrigerator, Freezer, Dishwasher, Microwave, Fireplace & Chimney, Exterior Workshop/Storage Building, Mounted TV in Fam Rm, Mounted TV in Kitchen. The Grandfather Clock and Bookcase in foyer can also convey. The Rolling Cart under bar in kitchen DOES NOT convey. Roof is 10 years old, Heat Pump 10 years.

12113 Chesmount Drive, Chesterfield

$325,000

4 Beds ⋅ 3 Baths ⋅ CVR-2627051 MLS

Welcome to this four-bedroom, two-and-a-half-bath home located in the established Sleepy Hollow subdivision of Chesterfield County. This property offers a great opportunity for buyers looking to bring their vision to a home with excellent potential. The home will require some repairs and updates, providing the opportunity to customize and enhance the property to suit your needs. Ideally situated with convenient access to Hull Street, Route 288, and Richmond, this home offers a desirable location within an established residential community. With thoughtful improvements and some TLC, this property has the potential to become a beautiful home in a wonderful neighborhood. Bring your ideas and explore the possibilities this property has to offer. This home is being sold AS IS, Where IS, Fireplace and Shed are AS IS as well. Please provide AS IS addendum in all offers. Priced below county assessment!

12341 Escada Drive, Chesterfield

$335,000

3 Beds ⋅ 2 Baths ⋅ CVR-2627013 MLS

Welcome home to this nicely appointed ONE LEVEL LIVING three bedroom, two bathroom home located on a quiet cul-de-sac. Upon entry, you'll appreciate the large family room with vaulted ceilings and brick fireplace, which flows seamlessly to the kitchen and built in breakfast area. The primary suite is located at the end of the home with two large closets and a private ensuite bathroom. The other two bedrooms share an updated hall bath with tub/shower combo. The back deck overlooks a large fenced backyard that is perfect for both entertaining and relaxing. Conveniently located to Powhite Parkway and Midlothian Turnpike, you'll be close to endless shopping and dining options. Don't miss this one, schedule your showing today!

401 Grinell Drive, Chesterfield

$499,990

3 Beds ⋅ 3 Baths ⋅ CVR-2626943 MLS

Brand-new Paired Villa END UNIT Monroe in the Cottages at Millwood, estimated for completion in early 2027! This thoughtfully designed 3-bedroom, 2.5-bath home combines stylish finishes with an easy, functional layout and a homesite that backs to open space for a little extra breathing room. The main level features a dedicated home office, spacious family room and a beautiful kitchen with 42" white cabinetry, quartz countertops, stainless steel appliances and a sage tile backsplash laid in a herringbone pattern. Durable LVP flooring extends throughout the foyer, office, family room, kitchen and powder room. Upstairs you'll find all three bedrooms plus a loft, including a spacious primary suite with a double vanity and tiled shower. Outside, enjoy low-maintenance fiber-cement siding and a covered rear porch overlooking open space which is a great spot for morning coffee or winding down at the end of the day. An attached 2-car garage adds even more convenience. New construction without the long wait! Come see why the Monroe at the Cottages at Millwood is such a great combination of style, space and low-maintenance living. This home is currently UNDER CONSTRUCTION with floor plan and design selections already finalized.

6435 Quinlynn Place, Chesterfield

$494,990

5 Beds ⋅ 3 Baths ⋅ CVR-2626942 MLS

Need more bedrooms without giving up the ease of low-maintenance living? Meet the Chamberlayne at the Cottages at Millwood! This brand-new END UNIT Paired Villa offers an impressive 5 bedrooms including a first floor primary, a loft and 2.5 baths, giving you the flexibility for guest rooms, home offices, playrooms; or simply room to spread out. The open main level is designed for everyday living and entertaining, while the kitchen features stylish finishes, quartz countertops, stainless steel appliances, upgraded lighting and a gas range. Upstairs, you'll find four bedrooms, large loft, plenty of storage and a bathroom featuring a double sink vanity. Outside, Mountain Sage fiber-cement siding, crisp white trim and a black Craftsman-style front door give this home fantastic curb appeal. Relax out back on the covered porch, or enjoy the extra light and privacy that comes with an end-unit homesite located in a cul-de-sac. An attached garage completes the package. This home is currently UNDER CONSTRUCTION with floor plan and design selections already finalized, and will be available early 2027!

6440 Quinlynn Place, Chesterfield

$430,000

3 Beds ⋅ 3 Baths ⋅ CVR-2626460 MLS

Welcome to 4907 Lancewood Road. This inviting home features an open, flowing floor plan filled with an abundance of natural light. The spacious layout creates an easy connection between the living areas, making the home comfortable for both everyday living and entertaining. The primary suite offers a private retreat with an attached primary full bathroom, walk-in closet, and plenty of space for a seating area. Outside, enjoy easy-maintenance landscaping supported by an irrigation system and established grass. The backyard also borders a natural wooded area, providing a peaceful, scenic backdrop and a sense of privacy.

4907 Lancewood Rd, Chesterfield

$454,999

4 Beds ⋅ 3 Baths ⋅ CVR-2626937 MLS

$5,000 SELLER CREDIT TO BUYER! Classic charm meets stylish finishes in this inviting 4-bedroom, 3-full-bath home. A generous covered front porch, distinctive exterior, and picket fence create memorable curb appeal. Inside, warm wood floors, abundant natural light, recessed lighting, and crisp trim complement the thoughtfully designed layout. The main level offers a welcoming living room, separate dining room, and breakfast nook adjoining a kitchen with white cabinetry, stainless steel appliances, and ample counter space. The spacious main-level primary suite features a beautifully appointed bathroom with a double-sink vanity, glass-enclosed shower, and freestanding soaking tub. A second bedroom and additional full bathroom provide added flexibility on the main floor. Upstairs, two bedrooms and a versatile bonus area offer space for a home office, reading lounge, play area, or additional sitting room. A dedicated laundry area adds everyday convenience

12105 Mathenay Drive, Chesterfield

$425,000

5 Beds ⋅ 3 Baths ⋅ CVR-2626828 MLS

Fantastic home in very desirable neighborhood! Remodeled with a huge open family room, updated bathrooms, neutral colors, and move in ready. The 3rd floor 5th bedroom is completely finished with its own heat and air mini-split, can be a playroom, media room, craft area, or he/she cave! Inside you will find hardwood floors, updated fixtures, ceiling fans, vinyl windows throughout, stainless appliances, and more. The primary bedroom has his and her closets, and the attached primary bath that features glass wall shower and updated fixtures. All bedrooms have ceiling fans and updated lighting. Outside you have plenty of paved off street parking, attached one car garage, concrete basketball court, oversize rear deck, 10x10 detached storage shed, and large level fenced in rear yard. Roof and HVAC are both less than 7 years old so you should have no major expenses anytime soon. Move in and make it your own. Community pool is included with HOA dues, plus playground, tennis, volleyball, and sports field, all just a short walk away. Award winning Chesterfield County Public Schools, and easy access to shopping, dining, and major roads.

4207 Brixton Road, Chesterfield

$399,000

4 Beds ⋅ 3 Baths ⋅ CVR-2626567 MLS

Opportunity awaits in Kings Grove! This 4-bedroom, 2.5 bathroom home offers 2,306 sq ft, a 2-car garage, and a thoughtfully designed floor plan with plenty of room to live, work and entertain. The two-story foyer welcomes you with hardwood floors and abundant natural light and leads to an office, formal dining room, and well-appointed kitchen with ample cabinet and counter space, new dishwasher, pantry and eat-in area. The kitchen opens to the family room, featuring a gas fireplace and access to the 12' x 16' rear deck—perfect for gatherings. A large laundry room with convenient laundry chute from the 2nd floor adds functionality. Upstairs, the generous primary suite features a walk-in closet and private bath with a soaking/jetted tub, separate shower and double vanity. Three additional bedrooms offer excellent accommodations, including a fourth bedroom nearly the size of the primary. Additional features include 2-zone HVAC with 2nd-floor system replaced in 2019, water heater replaced in 2019, vinyl siding, a substantial vinyl privacy fence enclosing the backyard with 2 separate access gates, as well as a double-width, paved driveway. Priced at $399,000 to reflect the opportunity for new paint, new carpet, several deck board replacements and deck restaining. Comparable 4-bedroom homes in the neighborhood with new paint and new carpet have recently sold in the $425,000–$430,000+ range. Bring your vision and make this home your own! Conveniently located near shopping, dining, parks and major commuter routes. Property is being sold As-Is. Floor plan available in photos.

5718 S Jessup Road, Chesterfield

$216,600

3 Beds ⋅ 1 Baths ⋅ CVR-2626821 MLS

ESTATE AUCTION Cash, AS IS terms Price shown is tax value, name your price at online auction~ Early offers presented - Brick Ranch 1,116 SF, N Chesterfield, VA Classic Mid-Century Brick Home Well-Maintained, Original Kitchen/Bath Hardwood Floors under Carpet Renovate for Tenant or Flip First time on market since 1976 Living room with Picture Window Eat-in Kitchen 3 bedrooms Hall bath, linen and coat closets Mud room with Washer/Dryer hookups Pull down attic, partially floored Rear Deck and Shed Central air just a few years old, oil heat with above ground tank Convenient to VA Hospital, Walmart, Meadowbrook County Club

4738 Willesden Road, Chesterfield

$349,000

3 Beds ⋅ 3 Baths ⋅ CVR-2626575 MLS

THIS IS YOUR CHANCE TO OWN A NEWER END-UNIT TOWNHOME OFFERING UPGRADES THROUGHOUT, LOW MAINTENANCE & COMFORTABLE LIVING WITH COMMUNITY AMENITIES IN CHESTERFIELD. This home offers 3 beds, 2.5 baths, open concept & an attached garage! A brick front with arched hidden entry welcomes you inside to ample living space & an abundance of natural light making this townhome feel like a single-family home. On the main level, a large Kitchen with gas cooking, backsplash, granite and an oversized island provides plenty of room for cooking and entertaining. The kitchen opens to a spacious dining room and airy living room with a beautiful corner gas fireplace and tons of natural light. A powder room and rear family entryway from the garage, as well as the rear driveway, complete the 1st floor. Notice the detail to the upgraded staircase as you make your way upstairs. Oak stairs, metal spindles and a beautiful trim wall warms the space up beautifully! On the 2nd floor is a generous primary bedroom that features a tray ceiling, a huge walk-in closet and a cozy window bench. The en-suite bath features a double vanity, walk-in tiled shower and a large soaking tub. Two more spacious bedrooms with ample closet space, a hall bath and laundry closet complete the 2nd floor. A 1-car attached garage w/storage can be found at the rear of the property, with access to the rear entry driveway. This gem is conveniently located within a short commute to major highways & has access to the community amenities including beach entry pool, clubhouse with fitness, splash park, playgrounds and more!

7853 Old Guild Road, Chesterfield

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