Chesterfield, Virginia MLS Real Estate Search

Chesterfield, VA MLS Real Estate Search and Listing

Commonly referred to as the "South Side" of Greater Richmond, Chesterfield County is located just south of the state capital in the Commonwealth of Virginia. The county borders are primarily the James River to the north and the Appomattox River to the South. The Chesterfield Court House is the county seat.

The population of Chesterfield has been growing and it is the third-most populous county in Virginia (behind Fairfax County and Prince William County, respectively). 

The following MLS real estate listing includes the Chesterfield County area with the most recent listings first. Please contact us if you would like a customized real estate listing, which we'll be glad to provide.

Chesterfield MLS Real Estate Listings

$545,000
3 Beds 3 Baths CVR-2624849 MLS
Welcome to 1799 Outrigger Drive in Twin Rivers at Meadowville Landing! This beautifully designed 2,152-square-foot home offers true one-level living with three bedrooms, three full bathrooms, two private primary suites, and a spacious open floor plan. Step inside the welcoming foyer, where elegant picture-frame wall molding and five-panel interior doors create a polished first impression. One side of the home features a private primary suite with its own full bathroom, a second bedroom, and a spacious office enclosed by French doors. The main primary suite is thoughtfully positioned on the opposite side of the home, providing added privacy and separation. At the heart of the home, the kitchen opens seamlessly to the dining and family rooms—perfect for everyday living and entertaining. The kitchen features granite countertops, abundant cabinetry, stainless steel appliances, and a generous center island. The family room offers a tray ceiling, built-in shelving, and a cozy fireplace. French doors lead to the beautiful screened porch, where a second stone fireplace creates the perfect setting for relaxing or entertaining throughout the seasons. Additional highlights include three full bathrooms and an attached two-car garage. Twin Rivers residents enjoy access to Meadowville Landing’s resort-style amenities, including a clubhouse, fitness center, pool with slide and splash area, playground, fishing ponds, river walk, and community dock along the James River. Pickleball and bocce ball courts add even more ways to enjoy the community—all conveniently located near Route 10 and I-295. Community details

1799 Outrigger Drive, Chester

$399,990
2 Beds 2 Baths CVR-2624831 MLS
Don’t miss this immaculate maintenance free home sitting on one of the best lots in The Townes at Notting Place with exceptional private water views!! This 55+ community home offers just under 1600 sq ft, 2 first floor bedrooms, 2 full baths, and a one car attached garage. The exterior offers maintenance free living with a concrete driveway, vinyl siding, 30 year dimensional roof, professional landscaping, and an awesome rear covered porch with a stamped concrete patio extension overlooking the community pond. The interior is meticulously keep with an open inviting floor plan from Stylecraft Builders. The main area offers a large and bright family room with natural colored LVP flooring, recessed lighting, and ceiling fan. The bright and open chef’s kitchen boasts a large center island, granite counter tops, 42’ custom cabinets with soft close drawers, stainless steel appliances, large pantry, coffee bar area, and natural colored LVP flooring. The first level primary suite is huge with views overlooking the community pond and offers W/W carpeting, ceiling fan, walk in closet, and a large en suite with large walk in shower with bench seating, double vanity, and tile flooring. The second first level bedroom offers W/W carpeting and a large closet with an adjacent hall bath with walk in shower and tile flooring. Upstairs you will find a nice sized loft area perfect for an office or just some relaxing time. There is also a great conditioned walk in storage space upstairs. Other features include first level laundry area and tankless hot water. Lastly in case you missed it the large covered porch area over looking the pond is perfect for morning coffee and afternoon relaxation. The HOA covers all exterior maintenance, trash pick up, roof and siding repairs. This community is close to hospitals, interstates, all dining and shopping chesterfield has to offer, and 15 mins to downtown RVA!!

1537 Westhall Gardens Drive, Midlothian

$780,000
4 Beds 5 Baths CVR-2624793 MLS
Gorgeous, fully renovated stately Dutch Colonial in sought-after Bexley! Lots of space for everyone, amazing flexible floor plan, and a natural wooded lot for exceptional privacy in a super convenient location. From the foyer, the living room to the right features recessed lights, a wood-burning fireplace, and French doors leading to the formal dining room. This room could easily be used as an office or converted to a first floor bedroom, as it has direct access to the downstairs laundry, which includes a large closet and full bath. Perfect for multi-generational families or a mother-in-law suite. The family room on the other side of the first floor offers a beautiful gas fireplace, wet bar, and access to the massive screened back porch with beautiful floors and ceiling fan for slow mornings or quiet evenings. Anchoring the first floor is a show-stopping brand new kitchen boasting white shaker cabinets, stainless appliances, including gas cooktop and double wall ovens, center island with seating, stunning quartz counters and tile backsplash, and breakfast nook. Take the party downstairs, where you'll find another half bath, and half of the walk-out basement serving as a rec room with tile floors and another wet bar and gas fireplace, and the other half dedicated to the 2+ car garage. Beautiful outdoor space on this level as well, with a covered slate patio with fan directly under the deck.  The second floor is home to a tranquil primary suite with brand new hardwood floors, custom closet, en suite spa bath with double vanities, tiled shower with seat, and separate tub.  Three more bedrooms share a hall bath, also with double vanity. Laundry also on this level. Brand new and refinished flooring throughout, freshly painted inside and outside, Hardieplank siding, new light and plumbing fixtures—it's all been done!

9365 Cardiff Loop Road, Midlothian

$461,440
2 Beds 4 Baths CVR-2624834 MLS
Welcome to the Richmond “A” by Main Street Homes at Oasis! This three-story townhome pairs modern style with thoughtful design and exceptional craftsmanship. Offering 2 bedrooms, a study/office, 3.5 baths, a rear-entry 2-car garage, rear deck, tankless water heater, and low-maintenance vinyl siding, this home delivers comfort and convenience across three beautifully designed levels. The first floor welcomes you with a versatile study/office and full bath—ideal for working from home, guests, or creating a flexible personal space. Upstairs, the open-concept main level is designed for effortless everyday living and entertaining, featuring a spacious great room, dining area, powder room, and a beautifully appointed center-layout kitchen. Quartz countertops, ceramic tile backsplash, stainless-steel appliances, and an oversized island create a stylish and functional gathering space. The third-floor primary suite offers a private retreat with TWO walk-in closets and a luxurious ensuite featuring a large ceramic tile shower and double-bowl vanity. A spacious guest bedroom with its own full bath and a convenient laundry room complete the upper level. Beyond your front door, Oasis offers an exceptional low-maintenance lifestyle with a state-of-the-art clubhouse, resort-style outdoor pool, pickleball courts, dog park, community garden, playground, parks, and sidewalks throughout. Conveniently located in Chesterfield County with easy access to shopping, dining, entertainment, and major roads, Oasis puts everyday conveniences within reach while offering an inviting place to call home.THIS HOME IS UNDER CONSTRUCTION. THE PHOTOS, VIDEOS, AND/OR 3D TOUR SHOWN REPRESENT THE FLOOR PLAN BUT ARE NOT OF THIS SPECIFIC HOME. SELECTIONS AND FEATURES ARE SAMPLES AND NOT THE ACTUAL SELECTIONS AND FEATURES IN THE HOME. SEE A NEW HOME CONSULTANT FOR DETAILS.

15361 Oasis Sun Way, Midlothian

$837,777
5 Beds 4 Baths CVR-2624818 MLS
Fully renovated 1.4-acre turn-key estate in Brandy Oaks! This meticulously updated property features a stately brick-pillared entrance, English gardens, an attached 2-car garage, and an extended gravel lot for effortless parking. Inside, a grand foyer with 12-foot ceilings leads to a private enclosed office, a cozy library, and an open-concept dining room with a fireplace. The chef's dream kitchen is beautifully upgraded with pristine quartz countertops, a farmhouse sink, stainless steel appliances, and Italian-inspired tile. Unwind in the sunroom, which boasts vaulted ceilings and a wall of windows capturing beautiful outdoor views. Designed with distinct wings, the home features exceptional space: West Wing: Huge great room with a fireplace, bar, billiard room, and a private primary loft suite featuring a massive walk-in closet and spa-like tub. East Wing: Second primary suite with a new double shower, three additional bright bedrooms, a full hallway bath, and a dedicated laundry room. The resort-style backyard features an expansive two-level deck with a covered grilling area, hot tub, and outdoor fireplace. Beyond the deck, enjoy a private beach, swimming lagoon, beachside fire pit, mini vineyard, and fruit orchard. A detached 2-car garage is currently utilized as a personal home gym but also suits a workshop or additional finished space. Practical upgrades include a solar panel system, new water heaters, and a full-lawn sprinkler system. Near local schools, shopping, and hiking at Pocahontas State Park.

13720 Brandy Oaks Drive, Chesterfield

$565,000
5 Beds 3 Baths CVR-2623470 MLS
Welcome to 11106 Jimmy Ridge Drive, a beautifully updated home offering generous living space, a flexible 4–5 bedroom floor plan, and an impressive list of recent improvements. The first floor offers a sunny living room and dining room, plus a renovated eat-in kitchen with quartz countertops, tile backsplash, large sink, new faucet, disposal and microwave, and Frigidaire Professional appliances, including a gas range with oven and French-door refrigerator. 2 pantry closets for extra storage. Wood-look laminate flooring flows throughout the first floor, and fresh paint gives the home a bright, move-in-ready feel. The spacious family room features a gas fireplace and opens to a wonderful screened porch. Beyond, enjoy a hardscaped patio with hot tub and built-in sitting wall overlooking a fenced backyard that backs to woods for added privacy. Upstairs, the expansive primary suite is a true retreat with its own gas fireplace, two closets, and beautifully remodeled en suite bath. Renovated in 2026, the bath features two vanities with connecting counter, quartz countertops, new sinks, fixtures, mirrors and lighting, updated flooring, large tub, private water closet and walk-in closet. The hall bath has also been refreshed with painted cabinetry, new fixtures, mirrors and lighting. Brand-new carpet Sept. 2026. Three additional bedrooms complete the second floor, including one with a walk-in closet. A spacious laundry room with built-in cabinetry adds convenient storage, along with 2 hall closets. The third-floor flex space offers even more versatility as a fifth bedroom, home office, playroom, exercise or media room, plus walk-in attic storage. Outside, low-maintenance vinyl siding complements valuable recent improvements, including a new roof, gutters, downspouts and hot water heater in 2023, heat pump in 2022, garage door in 2025, plus a storage shed. The two-car garage has storage racks. Move-in ready with the updates, space, storage and outdoor living you're looking for! Convenient to highways and shopping.

11106 Jimmy Ridge Drive, Chesterfield

$549,000
4 Beds 3 Baths CVR-2624516 MLS
Welcome to 4601 Otterdale Road, a fully renovated home on just over one private acre with no HOA in the award- winning Cosby High School District. Every space has been updated with quality materials and thoughtful design throughout, including a new roof, new HVAC system, and new hot water heater. Inside, you'll find hardwood floors, fresh paint, new lighting, designer wallpaper, and two living areas. One offers abundant natural light and opens to the kitchen, while the second is moody and comfortable with a wood-burning fireplace. The custom kitchen features backlit Cristallo quartzite countertops, custom cabinetry, stainless steel appliances, a large skylight, and a built-in banquette. The primary suite includes vaulted ceilings with remote-controlled skylights, a spa-inspired bathroom with a walk-in shower, an oversized custom closet, and private access to the rear deck. Three additional bedrooms are located in their own wing of the home, along with a custom tiled and wallpapered full bathroom. Each bedroom offers its own personality with ample space, storage, and natural light. Outside, the fully fenced property spans just over an acre and includes raised garden beds and multiple outdoor seating areas. The driveway has two entrances, providing easy access and potential for a future detached garage. Located directly across from Summer Lake and near Moseley's new and upcoming development, as well as minutes from Westchester Commons, the home offers convenient access to shopping, restaurants, grocery stores, fitness centers, and coffee shops.

4601 Otterdale Road, Moseley

$799,900
5 Beds 4 Baths CVR-2624810 MLS
Modern design, custom craftsmanship, and a thoughtfully designed floor plan come together in this striking Homesmith Construction home in Summer Lake. A custom take on the Keswick floor plan, the home pairs clean architectural lines with warm, elevated finishes, including hardwood floors throughout and carefully considered details at every turn. Inside, the spacious family room is anchored by a gas fireplace with custom built-ins and opens seamlessly to the beautifully appointed kitchen. Custom cabinetry, quartz countertops, a generous walk-in pantry, and an oversized breakfast nook create a space equally suited for everyday living and entertaining. A first-floor guest bedroom adds valuable flexibility for visitors, a private office, or multi-generational living, while the expansive screened porch extends the living space outdoors. Upstairs, the primary suite offers a private retreat with a large walk-in closet and beautifully finished en suite featuring a soaking tub and oversized tiled shower. Two additional bedrooms share a Jack-and-Jill bath, while a fifth bedroom enjoys its own en suite bath and spacious closet. With five bedrooms, multiple gathering spaces, and the quality and character of a custom Homesmith build, this Summer Lake home delivers modern design without sacrificing comfort or functionality. An exciting opportunity to own a truly distinctive home in one of Chesterfield County’s premier communities.

4612 Singing Bird Drive, Moseley

$645,000
4 Beds 3 Baths CVR-2623878 MLS
Welcome to 9507 Simonsville Road, an exceptional 2021-built Amelia floor plan by Main Street Homes offering 3,388 finished sq. ft. of beautifully designed living space. From the moment you arrive, the quality and attention to detail are evident, with a concrete driveway and walkway, lush irrigated lawn, and a spacious front porch. Inside, 9-foot ceilings and engineered hardwood floors create a bright, polished feel throughout the main living areas. The open-concept kitchen and family room are ideal for both everyday living and entertaining. The family room features a gas fireplace and ceiling fan, while the impressive eat-in kitchen showcases a large island with pendant lighting, leathered granite countertops, pantry, and stainless appliances. The first-floor primary suite offers a private retreat with a beautifully appointed bath featuring a glass-enclosed shower, jetted tub, dual vanity, and an oversized walk-in closet. A dedicated first-floor laundry room adds everyday convenience, while the additional main-level spaces offer flexibility for dining, guests, work, or hobbies. Upstairs, the spacious loft provides a versatile gathering area, while the separate bonus room offers endless possibilities. The finished garage is a standout feature, equipped with Mitsubishi mini-split HVAC and built-in surround sound. Whether used for recreation, fitness, or additional entertaining space, this is far more than a typical garage. Outside, the 19' x 12' concrete rear patio overlooks a lush lawn with mature trees along the rear property line, creating a private and inviting outdoor setting. A custom-built detached shed provides additional storage, and generator pre-wire adds valuable convenience. This home offers easy access to shopping, dining, services, and recreation while providing a beautifully appointed place to call home. Homes offering this combination of newer construction, upscale finishes, flexible living space, and an extraordinary finished garage are hard to find. Schedule your private showing today!

9507 Simonsville Road, Midlothian

$599,000
3 Beds 3 Baths CVR-2624781 MLS
Welcome to 14119 Shawhan Place, an exceptionally well-maintained, freshly painted original-owner Boone Homes residence designed for comfortable, low-maintenance living. Located in Madison Village at Charter Colony, this home offers the space, quality and convenience with features that make it easy to enjoy for years to come. Inside, you’ll find 3 bedrooms, 2.5 bathrooms, a timeless and airy kitchen, granite countertops, tile backsplash and a lovely inviting florida room with french doors adding elegance and privacy. All bedrooms are equipped with ceiling fans, closets and large windows. The primary en-suite bedroom includes two walk in closets and a separate vanity between the closets. The primary bathroom offers a soaking tub, walk in shower and a two sink vanity. The spacious walk-in attic offers exceptional storage or can easily be finished to add a fourth bedroom or entertainment area, even another bathroom. Outside, the HOA takes care of the work you don’t want to worry about, including lawn maintenance, snow removal, gutter cleaning and shrubbery upkeep. Spend less time on home maintenance and more time enjoying life. Madison Village at Charter Colony offers a convenient, connected lifestyle close to medical care, physicians, pharmacies, grocery stores, restaurants and everyday shopping. The new fire department is less than a mile away, and nearby Lifelong Learning in Midlothian provides opportunities to stay active and engaged. Comfortable. Convenient. Low-maintenance. Designed for the next chapter. New roof was installed in August 2026. HVAC units were recently inspected and are on a maintenance rotation twice a year.

14119 Shawhan Place, Midlothian

$1,349,950
4 Beds 4 Baths CVR-2624771 MLS
Discover exceptional craftsmanship and modern comfort at 13216 Bradley Bridge Road. Set on 6.5 picturesque acres with beautiful water views, this stunning new-construction home offers privacy, natural beauty, and refined single-level living with premium finishes and a thoughtfully designed floor plan. Soaring 10-foot ceilings in the bedrooms and bathrooms and dramatic 12-foot ceilings in the main living areas create an impressive sense of space. Spray-foam insulated walls, a conditioned spray-foam insulated crawl space, insulated thermal interior doors, and Harvey windows with black exterior trim enhance comfort and efficiency. The open-concept living room, dining area, and expansive eat-in kitchen provide an inviting space for entertaining and everyday living. The kitchen showcases upgraded Wolf Cabinetry in Grove White, a contrasting Grove Sandalwood island, quartz countertops with a waterfall edge, breakfast nook, and walk-in pantry. The laundry room is conveniently located off the primary suite, while the additional bathrooms and laundry feature Wolf Cabinetry in Grantley White. Premium Shield 4Max rigid-core flooring with a 28-mil wear layer offers waterproof and scratch-resistant performance and a lifetime warranty. Bathrooms and laundry feature porcelain flooring and wall finishes.The exterior features durable metal siding, metal soffits, metal roofing over the front porch, and a shingle roof. The spacious 3-car garage offers impressive 14-foot ceilings and insulated polyurethane garage doors with windows. Enjoy peaceful water views from the welcoming front porch or relax on the rear screened-in porch overlooking the serene landscape. With beautiful acreage, premium materials, energy-efficient construction, and quality craftsmanship throughout, this exceptional home was designed for comfort, style, and lasting enjoyment.

13216 Bradley Bridge Road, Chester

$475,000
4 Beds 3 Baths CVR-2624741 MLS
Tucked away on a quiet cul-de-sac, this beautifully updated home offers the perfect blend of comfort, style, and space—ready for you to simply unpack and enjoy your next chapter. As you step inside, you’re welcomed by a formal living room and dining room that flow seamlessly together, creating an inviting space for entertaining, holiday gatherings, or everyday living. Fresh paint, refinished hardwood floors, updated lighting, new hardware and faucets, and polished tile flooring give the home a fresh, modern feel throughout. Toward the heart of the home, the spacious kitchen opens directly to the family room, creating a comfortable gathering space anchored by a cozy fireplace. The kitchen features granite countertops, new stainless steel appliances, a center island, eat-in kitchen and plenty of room for cooking, conversation, and entertaining. Upstairs, brand-new carpet leads to generously sized bedrooms, including a spacious primary suite with a corner soaking tub and separate shower—your own private place to recharge. The finished third floor adds even more flexibility and is ready to become a home office, media room, playroom, fitness space, or guest retreat. Outside, enjoy a fenced backyard and freshly re-stained deck with plenty of room for cookouts, entertaining, morning coffee, or simply unwinding. A two-car garage and paved driveway add everyday convenience. With a brand-new roof, new HVAC system, new appliances, refreshed flooring, fresh interior paint, updated fixtures, and more, many of the big-ticket improvements have already been handled. Move-in ready, thoughtfully refreshed, and waiting for its next story—come make this one yours.

4101 Cara Hill Court, Chester

$485,000
4 Beds 3 Baths CVR-2623852 MLS
Welcome to the Highlands! This 4-bedroom, 2.5-bath home offers the perfect blend of comfortable living, spacious surroundings, and access to an incredible array of community amenities. Situated on a spacious 1+ acre corner lot with a natural tree buffer on three sides, this property offers privacy while being just a short walk from the golf course, pool and fitness room. Inside, the updated kitchen features newer cabinetry, quartz countertops, tile backsplash, and stainless-steel appliances, creating a functional and inviting space for everyday living and entertaining. The kitchen opens to a spacious family room complete with wood floors and a gas fireplace, while the formal dining room and first-floor half bath provide additional space for hosting family and friends. Upstairs, the generous primary suite offers a walk-in closet and private en-suite bath, complete with a large soaking tub and separate shower. Three additional bedrooms and a full hall bath provide plenty of space for family, guests, or a home office. Additional updates and features include new upstairs HVAC in 2026, a conditioned crawl space designed to improve efficiency and longevity, and an attached garage with a newer garage door. Enjoy all that The Highlands has to offer, from golf and dining to fitness, pool, recreation, and beautiful surroundings. This home is ready for its next owners to add their own personal touches and create years of wonderful memories. Come see for yourself and fall in LOVE!

12000 Glen Kilchurn Drive, Chesterfield

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