Chesterfield County Real Estate

Chesterfield County Real Estate

Welcome to Chesterfield County, Virginia, a vibrant and welcoming community that perfectly blends suburban charm with the conveniences of urban living. Nestled just south of the bustling city of Richmond, Chesterfield offers residents a unique opportunity to enjoy a peaceful lifestyle while being only minutes away from the rich history and cultural attractions of Virginia's capital.

Chesterfield County is renowned for its picturesque landscapes, featuring lush parks, serene lakes, and scenic trails that invite outdoor enthusiasts to explore. The county boasts over 30 parks, providing ample opportunities for hiking, picnicking, and enjoying nature. Notably, the beautiful Pocahontas State Park, one of Virginia's largest state parks, offers miles of trails, a swimming lake, and a variety of recreational activities for families and individuals alike.

Education is a cornerstone of Chesterfield County, with a highly-rated school system that prioritizes academic excellence and student development. Families appreciate the diverse range of educational options, including public, private, and charter schools, ensuring that every child receives a quality education.

Chesterfield also features a thriving economy, with a mix of local businesses and major employers providing ample job opportunities. The county is home to a variety of shopping centers, restaurants, and entertainment venues, making it a hub for social and cultural activities.

Whether you're looking to buy your first home, upgrade to a larger space, or find a cozy retreat, Chesterfield County offers a diverse range of real estate options to suit every lifestyle. Come discover the charm and warmth of Chesterfield, where community spirit and Southern hospitality await you!

Newest Listings in Chesterfield County

8307 Sterling Tide Court Unit CT, Chesterfield
$599,000
4 Beds ⋅ 4 Baths ⋅ CVR-2629418 MLS
Priced under $600,000 in The Highlands! Tucked away on a quiet cul-de-sac, this 4-bedroom, 3.5-bath home offers exceptional versatility, generous storage, and the privacy you’ve been looking for. With TWO primary suites—including one on the first floor with THREE closets—you’ll enjoy flexible living options and room to spread out. Grand windows fill the living room with beautiful natural light, creating an inviting setting for everyday living and entertaining. French doors add charm to the dedicated office, while the upstairs loft offers space for a lounge, game room, or your favorite hobbies. The spacious upstairs primary suite features an additional room ready for your imagination: create a dream dressing room, separate closets, a private office, or a relaxing retreat. A spacious walk-up attic provides abundant storage, and the two-car garage adds everyday convenience. Outside, the private backyard sets the scene for hosting friends, enjoying morning coffee, or unwinding at the end of the day. Updates include a downstairs HVAC unit replaced in (2025) and a roof replaced in (2017). Enjoy The Highlands’ golf-course community setting, with amenities including walking trails, basketball, a playground, a pool, tennis courts, and more. The Reserve restaurant, located within the neighborhood, offers dining overlooking the golf course an inviting spot to gather with friends or enjoy an evening close to home. This is more than a neighborhood it’s a lifestyle!

8307 Sterling Tide Court Unit CT, Chesterfield
11624 Switch Drive, Midlothian
$749,990
3 Beds ⋅ 5 Baths ⋅ CVR-2627843 MLS
MOVE IN READY! 4-story townhome features ROOFTOP deck, many designer upgrades including QUARTZ island, LVP flooring in main living areas, WOLF Range and Microwave drawer, SUBZERO refrigerator, outdoor Fireplace on the rooftop deck, Allusion gas fireplace in the family room, composite deck on 2nd floor, and many more upgrades to see! Welcome to The Junction at Midlothian Depot — Eastwood’s new boutique townhome community. This isn’t just a new street of homes. It’s a 13-acre mixed-use destination built for how people actually want to live: walk to dinner, grab groceries, meet a friend for coffee, walk your furry friend to the neighborhood dog park, then come home to a modern townhome with your own 2-car garage. We’re talking about roughly 60 upscale townhomes, private garages, green space, and a dog park for the four-legged family members. And right here at Midlothian Depot, the neighborhood is built around everyday convenience. The centerpiece is Chesterfield County’s first Whole Foods Market — a full-size organic grocery anchor, with tens of thousands of square feet of shopping, dining, and wellness around it.

11624 Switch Drive, Midlothian
11608 Switch Drive, Midlothian
$614,990
3 Beds ⋅ 4 Baths ⋅ CVR-2627935 MLS
MOVE IN READY! Welcome to The Junction at Midlothian Depot — Eastwood’s new boutique townhome condominium community! This 3-story townhome features KitchenAid 30" 5 burner smart gas range, upgraded designer finishes, composite deck, and a 2-car garage! This isn’t just a new street of homes. It’s a 13-acre mixed-use destination built for how people actually want to live: walk to dinner, grab groceries, meet a friend for coffee, then come home to a modern townhome with your own garage. And right here at Midlothian Depot, the neighborhood is built around everyday convenience. The centerpiece is Chesterfield County’s first Whole Foods Market — a full-size organic grocery anchor, with tens of thousands of square feet of shopping, dining, and wellness around it.

11608 Switch Drive, Midlothian
11616 Switch Drive, Midlothian
$624,990
3 Beds ⋅ 4 Baths ⋅ CVR-2627844 MLS
MOVE IN READY! This 3-story townhome features fabulous designer upgrades and finishes including an electric Allusion fireplace, beautiful lighting, QUARTZ countertop ISLAND, LVP flooring in main living spaces, KitchenAid wall ovens, gas cooktop, and dishwasher! This isn’t just a new street of homes. It’s a 13-acre mixed-use destination built for how people actually want to live: walk to dinner, grab groceries, meet a friend for coffee, then come home to a modern townhome with your own garage. And right here at Midlothian Depot, the neighborhood is built around everyday convenience. The centerpiece is Chesterfield County’s first Whole Foods Market — a full-size organic grocery anchor, with tens of thousands of square feet of shopping, dining, and wellness around it.

11616 Switch Drive, Midlothian
2459 Osborne Road, Chester
$229,500
2 Beds ⋅ 1 Baths ⋅ CVR-2629407 MLS
Super renovation of this 1951 villa. Everything inside is new. All fixtures, doors, hardware, HVAC. Refinished floors and fresh paint. Located minThis is the best value in the area. Scheduele your appointment soon!

2459 Osborne Road, Chester
14600 Castleford Court, Midlothian
$1,035,000
5 Beds ⋅ 5 Baths ⋅ CVR-2629408 MLS
Situated on 1.75 beautiful acres on a peaceful street with a cul-de-sac, this property offers an incredible combination of privacy, space, and thoughtful updates throughout! The gorgeous setting provides plenty of opportunities to enjoy the outdoors. Inside, you'll find hardwood floors, fresh paint, new carpet (2024), updated bathrooms, and two wood-burning fireplaces that add warmth and character. The beautifully updated kitchen (2022) features a new refrigerator, gas hookup for the range, and a convenient butler's pantry, making everyday living and entertaining a breeze. The primary ensuite offers a comfortable retreat, while the sunroom, provides a peaceful space to relax and enjoy the surrounding wooded views and trails. Outdoor living is just as impressive with a screened-in porch featuring TimberTech flooring, a deck overlooking the woods, a hot tub installed in 2023, and a newer patio (2025). The finished basement offers additional living and entertaining space, complete with a wood-burning fireplace and half bath. Recent improvements include replacement windows (2022), newer siding, updated lighting and sconces throughout the upstairs bedrooms and hallway, a new ceiling fan in the primary bathroom water closet, fresh interior paint and wall coverings, a new driveway retaining wall, and new fencing. The aggregate circular driveway, abundant storage, basketball goal, and outdoor gas grill hookup add even more convenience. With an incredible setting, spacious indoor and outdoor living areas, and numerous updates already completed, this property offers the perfect opportunity to enjoy privacy without sacrificing comfort or convenience!

14600 Castleford Court, Midlothian
14100 Southshore Road, Midlothian
$1,350,000
5 Beds ⋅ 4 Baths ⋅ CVR-2627046 MLS
Waterfront living at its finest! Imagine waking each morning to the peaceful beauty of Swift Creek Reservoir, where sparkling water, towering trees, and abundant wildlife create a private retreat you'll never want to leave. Nestled along the shoreline in desirable Southshore, this exceptional home offers more than beautiful water views—it offers a lifestyle! Start your day with coffee on the expansive rear deck or beneath the stunning vaulted, wood-beamed ceiling of the screened porch, watching ducks glide across the water and eagles soar overhead. Spend afternoons fishing from your private dock or cruising the 1,700-acre reservoir aboard the included 2023 22' Ranger pontoon boat with fishing package. Boat over to The Boathouse Restaurant at Sunday Park for dinner, then return home to unwind as breathtaking sunsets paint the sky over the water. Surrounded by nature yet just minutes from the shopping and restaurants along Hull Street Road, this peaceful Southshore sanctuary offers the rare opportunity to feel miles away without sacrificing convenience. Inside, the beauty of the outdoors takes center stage. A dramatic two-story family room with soaring arched windows floods the home with natural light while framing picturesque views of the wooded backyard and reservoir. The inviting, open living spaces flow effortlessly to the outdoors, making everyday living and entertaining a pleasure. Brick and Hardiplank siding complement the home's timeless appeal, while the main-level primary suite offers comfort and convenience. A formal dining room provides an elegant setting for gatherings, and a dedicated office/flex space accommodates work or hobbies. Upstairs, four additional bedrooms and two full baths offer generous accommodations, while a walk-up attic provides abundant storage or future expansion possibilities. Here, life moves at the pace of the water, and every day feels like a getaway. Welcome home to a waterfront retreat that feels like a vacation without ever leaving home!

14100 Southshore Road, Midlothian
1725 Winbury Drive, Midlothian
$399,000
4 Beds ⋅ 3 Baths ⋅ CVR-2629403 MLS
**LOCATION, SPACE & OPPORTUNITY!** Priced to Sell - Welcome to 1725 Winbury Drive, where a great location, spacious floor plan, and plenty of potential come together! If you've been looking for a home with room to spread out and the opportunity to make it your own, this one deserves a closer look! Offering 4 bedrooms, 2.5 baths, and 1,932 square feet, this home provides comfortable living spaces for everyday life and entertaining. Step inside to a generously sized living room featuring a gas fireplace, perfect for gathering with family and friends or relaxing at the end of a busy day. The separate dining room offers space for holiday celebrations and special occasions, while the eat-in kitchen provides a casual spot for morning coffee or everyday meals. You'll also appreciate the convenience of a first-floor laundry room and an attached 2-car garage! Upstairs, the spacious primary bedroom features vaulted ceilings that create an open, airy feel, along with its own private bath. Three additional bedrooms and a full hall bath provide plenty of flexibility for family, guests, a home office, or whatever fits your lifestyle. Pull-down attic access adds another practical feature! And let's talk about the outdoor space! A large deck stretches across the rear of the home, offering a wonderful place for grilling, entertaining, or simply enjoying some fresh air. The fenced rear yard provides even more possibilities for outdoor activities, gardening, or relaxing in your own backyard. LOCATION is another great reason to take a look!** Enjoy the convenience of nearby shopping, dining, and everyday necessities while having a place to call your own. This property is being sold **AS IS**, presenting a wonderful opportunity for buyers who recognize the potential and are ready to add their own personal touches. With 4 bedrooms, generous living spaces, a gas fireplace, attached garage, and great outdoor space, there's so much to work with! Bring your ideas, imagine the possibilities, and schedule your showing today!

1725 Winbury Drive, Midlothian
14440 Michaux Springs View, Midlothian
$445,000
3 Beds ⋅ 4 Baths ⋅ CVR-2628567 MLS
Welcome to Winterfield Park, described as a “one-of-a-kind urban community with suburban charm,” located between Salisbury and Midlothian Village. Enjoy low maintenance luxury while still having the privacy from the woods right outside your front door. This gorgeous light filled 3 Bedroom, 3.5 Bath townhome has three finished levels with 2 car rear-entry Garage, 1st floor bedroom with tinted windows and full bath access, open floor plan on 2nd level with hardwood floors. The gourmet kitchen, open to the living and dining rooms, includes granite countertops and 8-foot island. Enjoy the beautiful view of the wooded conservation space (with walking trails) from the balcony off of the dining area & relax or grill on the back deck off of the living room. The 3rd level features the expansive primary bedroom with an ensuite and walk-in closet & one additional bedroom also with an ensuite bath. The laundry room is conveniently located in the upstairs hallway. Attached 2 car garage is a bonus for storage & is already equipped with a plug for your generator or EV charger (220v line). The HVAC has also been upgraded to include a HEPA filter system. Winterfield Park is adjacent to multiple dining options, grocery shopping, coffee shops and more! Sidewalk access to places such as Triple Crossing, Wong's Tacos, Roots, and Starbucks - just to name a few. Minutes from the shops in the town of Midlothian, Winterfield Crossing, Kroger, Publix, Westchester Commons, and 288. The Resident’s Clubhouse is nearby and rentable for celebrations or can be used when you need an escape. The community pool has handicap pool lift & is open from Mid-May to Mid-September.

14440 Michaux Springs View, Midlothian
4624 Overlea Drive, Chesterfield
$319,000
3 Beds ⋅ 2 Baths ⋅ CVR-2629118 MLS
Welcome home to this 3-bedroom, 1.5-bath brick rancher! This home offers comfortable one-level living with hardwood flooring throughout much of the home, along with a cozy wood stove and central HVAC for year-round comfort. Recent updates include fresh interior paint, newer vinyl windows, and a newer roof. The crawl space has also been encapsulated and conditioned, offering added peace of mind. Step outside to enjoy the back deck and a nice backyard with room to relax, entertain, or enjoy the outdoors. Conveniently located near schools, shopping, and interstate access, this home offers a great combination of location, comfort, and potential. Come see all this home has to offer!

4624 Overlea Drive, Chesterfield
4401 Village Garden Circle, Chester
$449,000
3 Beds ⋅ 3 Baths ⋅ CVR-2629317 MLS
Welcome to this 1.5 story, all brick home in Chester Village Green. Living, dining, kitchen, foyer, hall & family room have new wood floors & fresh paint. Primary suite on 1st floor offers large walk-in closet & new carpet; ceramic tiled bath floor, large shower with double sinks & linen closet. 2nd bedroom has new carpet & double closets, ceiling fan. Kitchen has custom cabinets, large pantry, moveable island; open to family room with vented natural gas fireplace. Large 3rd bedroom on 2nd floor with 3rd bath, 2 closets, & walk-in to floored attic. This beautiful home has flipped gutters, central vac, storm doors. Hot water heater replaced in 6/25, new stove in 9/26. Walk into the home from the garage or backyard with no steps.

4401 Village Garden Circle, Chester
14301 Summercreek Terrace, Chesterfield
$749,999
6 Beds ⋅ 5 Baths ⋅ CVR-2629383 MLS
Welcome home to the Reserve at Summerford by Richmond American Homes, an exclusive collection of custom brick exteriors, side-entry garages, and spacious homesites. Situated on a lovely corner lot, this home features 6 bedrooms, 5 full bathrooms, and more than 3,600 square feet of beautifully designed living space. A dramatic two-story foyer welcomes you into a bright, open floor plan made for everyday comfort and memorable gatherings. The formal dining room connects through a butler’s pantry to the gourmet kitchen, where an expansive quartz island and stainless-steel appliances create an inviting place to cook, gather, and entertain. The spacious family room features a gas fireplace, while the sunroom opens to a 19’ x 10’ composite deck for effortless indoor and outdoor living. A first-floor bedroom and full bathroom offer flexibility for guests or multigenerational living, complemented by a convenient mudroom. Upstairs, retreat to a luxurious primary suite alongside four additional bedrooms, including two with private en-suite bathrooms, plus a full hall bathroom and a versatile homework or home office nook. Explore this limited new construction opportunity in the sought-after Summerford neighborhood. Schedule your private showing today. Showings by appointment only.

14301 Summercreek Terrace, Chesterfield
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