Chester Homes under $500,000

Chester Homes under $500,000

Welcome to Chester, Virginia—a charming town nestled in the heart of Chesterfield County, where suburban tranquility meets vibrant community spirit. With its rich history, beautiful parks, and convenient access to both Richmond and the scenic James River, Chester offers a perfect blend of small-town charm and urban convenience.

Homebuyers seeking affordability without sacrificing quality will be delighted to discover that Chester boasts a variety of homes priced under $500,000. This dynamic market features an array of styles, from cozy single-family homes to modern townhouses, catering to diverse lifestyles and preferences. Whether you’re a first-time buyer, a growing family, or looking to downsize, Chester has something to suit your needs.

Imagine living in a community where friendly neighbors gather for local events, children play in well-kept parks, and outdoor enthusiasts can explore miles of scenic trails. Chester is known for its excellent schools, making it an ideal place for families. The town's rich historical backdrop, highlighted by landmarks such as the Chesterfield County Museum and the historic Chester Village Green, adds a unique character that residents cherish.

As you explore the real estate options in Chester, you’ll find homes that not only fit your budget but also offer the chance to create lasting memories in a welcoming environment. With its affordable housing market, beautiful landscapes, and a strong sense of community, Chester, VA, is a place where you can truly feel at home. Come discover the charm and potential that await you in this delightful town!

Newest Chester Homes under $500,000

no property photo
$174,950
3 Beds ⋅ 1 Baths ⋅ CVR-2628071 MLS
Three Bedroom Rancher with great potential. Washer/Dryer and Refrigerator are included. Conveniently located! Cash or Conventional financing only. Property is being sold As-Is. Call today!

15900 Gary Avenue, Chester
3641 Kiefer Road, Chester
$335,000
3 Beds ⋅ 2 Baths ⋅ CVR-2628047 MLS
Welcome to this charming, ranch-style home located in the heart of Chester! Lovingly cared for by the same owner for over 40 years, this home offers a wonderful opportunity to make it your own while enjoying the benefits of an inviting layout, a beautiful lot and an unbeatable location. Inside, you'll find three spacious bedrooms, a large family room, a formal living room, and a dedicated dining room, providing plenty of space for everyday living and entertaining. This home has been exceptionally maintained and offers great space throughout while also showcasing the character of each room. Step outside to enjoy the expansive yard, beautifully accented by mature crepe myrtles in both the front and backyard. Relax on the welcoming front porch, entertain on the rear deck, or take advantage of the one-car garage, which includes a convenient workspace for hobbies or projects. Ideally situated just minutes from Chester Village, this home offers easy access to Interstate 288, making commuting and daily conveniences a breeze.

3641 Kiefer Road, Chester
no property photo
$275,000
3 Beds ⋅ 2 Baths ⋅ CVR-2627995 MLS
Bring Your Imagination and Restore This Home to Its Former Luster! Solid brick ranch home with a basement offering endless potential for investors, renovators, or buyers looking to make a home their own. The first floor features three bedrooms, one full bath, an eat-in kitchen, and a comfortable family room. A convenient first-floor stack washer and dryer add everyday practicality. The basement provides additional possibilities, with an unfinished bedroom, a second utility room with full-size washer and dryer hookups, and a one-car attached garage. Additional features include upgraded vinyl windows and an interior French drain system in the basement. With its solid brick construction and versatile layout, this property is ready for someone with vision to bring it back to life!

10601 Lunswood Road, Chester
15500 Richmond Street, Chester
$335,000
5 Beds ⋅ 3 Baths ⋅ CVR-2627925 MLS
Charming Cottage Cape with Space, Character & Endless Possibilities! Fall in love with the charm and versatility of this inviting Cottage Cape, offering spacious living areas and room for everyone! The first floor features a living room, dining room, and family room, all with beautiful hardwood flooring, along with a galley kitchen and separate utility room. The first-floor primary bedroom includes a full bath for added convenience. Upstairs, you'll find two additional bedrooms with walk-in closets, a full bath, and hardwood flooring. The basement offers even more possibilities, featuring a kitchenette with sink, two additional bedrooms, and a separate family room—ideal for extended family, guests, or a flexible living space. Outside, enjoy a large lot shaded by mature trees, providing a lovely setting with plenty of room to relax, entertain, or garden. This unique home offers generous space and a flexible layout to suit a variety of needs!

15500 Richmond Street, Chester
11319 Vulcan Lane, Chester
$438,900
3 Beds ⋅ 2 Baths ⋅ CVR-2627887 MLS
Welcome home to this beautifully like-new, one-level home! Featuring 3 bedrooms, 2 full bathrooms, and a 2-car garage, this home offers an open and functional layout with plenty of space for entertaining. As you enter, you’ll find two spacious bedrooms and a full hall bathroom, providing a great setup for guests, family, or a home office. Continue down the hallway into the heart of the home, where the open-concept family room and kitchen create an inviting space to gather. The kitchen features granite countertops, a large center island, and plenty of space for cooking, dining, and entertaining. The private primary bedroom includes an en suite with dual vanities, a tiled shower and a walk in closet. Step outside to enjoy the fully screened-in porch and beautifully designed patio, perfect for relaxing or entertaining. The finished two-car garage is equipped with a mini-spilt for cooling and heating, and the home also includes a generator, providing added convenience and peace of mind when you need it most!

11319 Vulcan Lane, Chester
11111 Surry Place, Chester
$499,900
4 Beds ⋅ 4 Baths ⋅ CVR-2627698 MLS
Welcome to your brand new, Chesterfield County, home! Perfectly situated on a large cul-de-sac lot, this well crafted two-story home comes with that finished basement you've always dreamed of! Upon arriving, you'll take note of the two car garage and welcoming front porch. Beyond the front door, attractive LVP flooring fills the living room and the entire first floor. From here, the view to the staircase and beyond will impress you as you make your way to the rear of the home where the open floorplan allows family room, dining room and kitchen to blend seamlessly! Sliding doors provide rear deck access. This kitchen will feature quartz countertops, stainless appliances, a pantry, recessed lighting and a 6 ft island with 10 inch overhangs! There's also a half bath on this entry level. Upstairs is where you'll find the deluxe master suite complete with a full bath, double vanity and walk-in closet. Three more generously sized bedrooms and another full bath are up here as well, along the the laundry room that is accessed from the upstairs landing. Okay, come check out the basement! What will you do with the tremendous rec room? The possibilities are many and the back yard can be accessed from this space. Also in the basement, you'll be delighted to discover another full bath and a room that would make a perfect office, study or hobby room. Out back, a 12x14 deck offers a perfect environment for enjoying your favorite beverage, pleasant breezes and time with loved ones. On the basement level, there's a concrete patio that provides yet another outdoor space to take advantage of. There's a 30 year, dimensional shingled, roof and the home has been wired for high-speed internet. From this fantastic address, Route 1, 288, I-95 and Route 10 are all just a few minutes away providing quick commutes to Downtown Richmond and all surrounding counties. Restaurants, shopping, banking and more are all close by making it more and more clear what a great opportunity this home represents. You'll be proud to own it!

11111 Surry Place, Chester
4137 Hamlin Terrace, Chester
$385,000
3 Beds ⋅ 3 Baths ⋅ CVR-2627717 MLS
** SHOWING BEGIN Friday 10/23/26**Amazing opportunity in Hamlin Estates. This 3 Bedroom, 2-1/2 BATH home has been well kept, and many upgrades have been applied. Kitchen has been Fully Upgraded w/Choice Detailed Cabinetry/Granite Tops (with Bar Stool Island) Custom Light + Plumbing fixtures/Stainless Steel appliances (Double Oven) and LG Tile flooring. Open Family Room from Kitchen is dressed in pristine Hardwood Floors, Detailed Hardwood moldings, Nat Gas Fireplace, custom Ceiling Fan/Light, an bright Earth-tone colors to support much natural light. Dining Room has a Pristine Hardwoods, generous Bowed Bay window with Crown+ Chair molding, Ceiling Fan + Light and Custom Sliding Barn Door. Primary Bedroom is very well sized and offers NEWER CARPET (Throughout All bedrooms and Stairwell) Ceiling Fan+Light, Walk-in Closet, and Fine Moldings. Primary Bath has been Partially Upgraded with Extra-Wide Vanity, Jetted Tub, Separate Shower Stall and Lavatory nook. Bed#2 Offers Fine Moldings, Cheerful Colors WTW Carpet and Nice Close Space/ Bed#3 is HUGE Offers Deep Walk-in Closet, Fine Moldings, WTW Carpet and Ceiling Fan + Light/ (3rd Floor- FLEX RM Could be 4th Bedrm) with a Built-in Bed, Built-in Shelves, Ceiling Fan and Light and a Double Closet. 3rd Floor also provides the large Walk-in Attic (15’3” x 11’6”)for all of your storage needs.2nd Floor Full Bath has been upgraded w/Custom Vanity, Mirror, Lighting to stay in harmony with other interior improvements in the house. The Laundry room is generously sized with Built-in Shelves and Linen Closet for the day-to-day needs. Garage Space has been used as Flex Space and offers countless possibilities. Rear Decking (off the Family Room) is another pleasing feature to this exciting property. 13” square Brick Paver Sidewalk leads to Children's Play Equipment and the Rear Fire Pit. Large Detached Shed conveys with the sale for all types of equipment storage. Property is close to Shopping,Interstate travel,Schools + Hospitals.

4137 Hamlin Terrace, Chester
4104 Birchleaf Court, Chester
$479,000
5 Beds ⋅ 4 Baths ⋅ CVR-2627424 MLS
**Need more room? Want flexibility without giving up charm? This is the one!** This spacious Colonial Revival-style brick home offers an impressive 3,520 sq. ft., 5 bedrooms, 3.5 baths, and a versatile multi-level floor plan on a beautiful 0.617-acre lot. From the grand front porch with classic columns to the expansive backyard and oversized Trex deck, this home offers space to live, gather, entertain, and make it your own. The main level features beautiful bamboo flooring throughout the living room, dining room, kitchen, hallway, and three bedrooms. The updated kitchen is ready for everything from weeknight dinners to entertaining, with oak cabinetry, granite countertops, a built-in wine cooler, and stainless-steel appliances. Fresh interior paint, vinyl tilt windows, an updated hall bath, and new carpet in the fourth bedroom add to the home's move-in appeal. **The lower level is a true game changer!** The spacious family room showcases a dramatic floor-to-ceiling stone fireplace with insert, blower, and custom mantel, creating an inviting place to relax. New luxury vinyl plank flooring and an adjoining butler's pantry/bar with built-in wine cooler make this level ideal for entertaining. And the possibilities don't stop there! A separate flex area with **private exterior access** includes a bedroom, upgraded full bath, tile flooring, and large storage closet. Think guests, extended family, a teen retreat, home office, hobby space, or your own private living area—the choice is yours. Step outside to the **33' x 20' Trex deck**, overlooking the large backyard and offering plenty of room for summer cookouts, morning coffee, gatherings, or simply enjoying your own space. Additional features include two-zone heating and cooling, central vacuum, and a two-car garage with one bay converted to conditioned flex space—perfect for a gym, workshop, studio, or hobby room. **Classic brick character + generous space + flexible living + a fantastic outdoor setting = a home you'll want to see in person!**

4104 Birchleaf Court, Chester
13624 Thornhill Place, Chester
$435,000
4 Beds ⋅ 3 Baths ⋅ CVR-2627455 MLS
Welcome to 13624 Thornhill Place, where thoughtful updates, generous outdoor space, and an inviting neighborhood setting come together to create a home that truly feels ready to enjoy. Tucked away on a quiet CUL-DE-SAC situated on more than half an acre, this property offers the privacy and breathing room buyers crave, complete with a spacious fenced backyard, welcoming front porch, and expansive rear deck perfect for morning coffee and evenings with friends. Inside, the beautifully UPDATED KITCHEN was completed in 2026 and serves as the heart of the home, featuring granite countertops, a stylish tile backsplash, shaker-style cabinetry, and new LVP flooring. The LVP continues throughout the first floor, creating a fresh, seamless look, with hardwood flooring underneath. Updated lighting throughout the main level and a refreshed powder room add to the home's polished, move-in-ready feel.The impressive family room offers plenty of room to gather and unwind, anchored by a cozy gas fireplace and complemented by dual ceiling fans. The outdoor setting is just as appealing, with a fenced backyard installed in 2023, mature surroundings, and plenty of room to play, garden, entertain, or simply enjoy the privacy of the lot. ENJOY ACCESS TO THE LARGE DECK FROM THE LIVING ROOM AND EAT IN KITCHEN. The ROOF was REPLACED in 2020, and a two-car garage provides additional convenience and storage. Beyond the home itself, the neighborhood offers the kind of lifestyle that's easy to appreciate, with a community pool, clubhouse, walking trails, and nearby elem. and middle schools within walking distance. It’s a setting that feels established, welcoming, and connected while still offering plenty of space at home. For additional peace of a mind sellers will pay for home warranty. This home has also been thoughtfully refreshed with buyer feedback in mind, with meaningful updates made to the kitchen, flooring, lighting, and upstairs bathroom. The result is a fresh, inviting home that is truly ready for its next chapter.

13624 Thornhill Place, Chester
2803 Jolly Lane, Chester
$439,000
5 Beds ⋅ 3 Baths ⋅ CVR-2626028 MLS
Welcome to 2803 Jolly Lane! This spacious 5-bedroom, 3-bath Chester home offers 2,674 square feet of comfortable living space and a functional floor plan designed for everyday living and entertaining. The beautifully updated kitchen features refinished cabinetry and granite countertops, creating a fresh and inviting space for preparing meals and gathering with family and friends. With five bedrooms, there is plenty of room for family, guests, a home office, or flex space. A convenient 2-car garage provides ample parking and storage. Located in a desirable Chester area with convenient access to shopping, dining, schools, and major roadways, close to Thomas Dale high school and walking distance to shopping. Fort Lee is only a 20 mins drive. This home is ready for its next chapter. Come see all that 2803 Jolly Lane has to offer!

2803 Jolly Lane, Chester
3552 Castlebury Drive, Chester
$309,950
3 Beds ⋅ 2 Baths ⋅ CVR-2627254 MLS
Easy one-level living meets comfort, style & convenience in this move-in-ready ranch in Cameron Run! This 3-bedroom, 1.5-bath home offers a bright, functional layout highlighted by a spacious great room with a cathedral ceiling & brick fireplace, creating an inviting centerpiece for everyday living. The updated kitchen features granite countertops, white cabinetry, stainless steel appliances & plenty of workspace, while wood-plank flooring adds a clean, cohesive look through the main living areas. Three generously sized bedrooms provide flexibility for family, guests or a home office. Outside, enjoy the spacious 17x12 rear deck overlooking the yard, plus an attached storage shed. The home is also equipped with a solar panel system, adding another modern feature to the property. Replacement windows, vinyl siding, an updated heat pump, water heater, and crawlspace insulation & vapor barrier add to the home's appeal. Conveniently located near shopping, schools, dining & interstate access, this is a fantastic opportunity to enjoy the simplicity of single-level living in an established Chester neighborhood.

3552 Castlebury Drive, Chester
10818 Belvoir Road, Chester
$355,000
3 Beds ⋅ 3 Baths ⋅ CVR-2627304 MLS
Welcome home to this charming 3-bedroom, 2.5-bath Colonial offering 1,632 square feet of comfortable living space! A welcoming covered front porch sets the tone before stepping inside to a spacious family room featuring exposed wood beams, a beautiful stone fireplace and plenty of natural light. The bright kitchen offers ample cabinet, pantry and counter space as it flows into the dining area, while an additional flex space provides the perfect spot for a home office, playroom or sitting room. Upstairs, you’ll find three generously sized bedrooms, including a spacious primary suite with a walk-in closet and private bath. The additional 2 bedrooms offer plenty of flexibility for children's rooms, a home office, guest space or whatever fits your lifestyle. Outside, enjoy the best of both worlds with a screened porch for relaxing, an adjoining deck for grilling and entertaining, and a fenced backyard with plenty of room to play, garden or simply unwind. With its inviting spaces, functional floor plan and being meticulously and thoughtfully updated, this holme reflects true pride of ownership throughout, with loads of character. This home is ready for its next chapter!

10818 Belvoir Road, Chester
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