Chesterfield Real Estate Search

Chesterfield Homes with a Pool for Sale

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Newest Chesterfield Homes with a Pool for Sale

14167 Parliament Dr, Chesterfield
$699,900
COMING SOON Status ⋅ David Werner
Welcome to LADUE TRAILS, one of the MOST SOUGHT AFTER NEIGHBORHOODS in Chesterfield! Spacious, inviting, and designed for connection, this 1970's brick ranch offers approximately 3,800 square feet, four bedrooms, and three full bathrooms—along with the flexible spaces and outdoor amenities that make everyday living and entertaining feel effortless. The main level welcomes you with three bedrooms, new flooring, and a beautifully appointed kitchen featuring custom cabinetry, marble countertops, and a stylish backsplash. Gather around the new gas fireplace in the comfortable living area, or extend the conversation into the large sunroom, where expansive views of the pool, patio, and park-like backyard create a natural backdrop for entertaining. Electrical service is already in place for a future hot tub, adding even more potential for outdoor relaxation. The expansive lower level is ideal for multigenerational living, extended guests, or a private retreat. It includes a spacious bedroom suite with an egress window, a full bathroom, a bar area, and a partial kitchen with the potential to be converted into a full kitchen. Additional washer and dryer hookups, generous storage, and extra closet space provide the flexibility and independence today’s households appreciate. Outdoor enjoyment comes naturally here, with a beautiful pool, inviting patio, and expansive backyard offering plenty of room for summer gatherings, play, and quiet evenings under the stars. The rear-facing, two-car garage is insulated and finished with drywall and includes storage shelving, washer and dryer hookups, and a freezer that stays. Ample parking makes hosting family and friends convenient. Additional highlights include a whole-house water softener, a roof approximately three years old, newer HVAC, and large televisions in nearly every room that remain with the home. Accessibility features, including safety grab bars, add comfort and convenience. With generous living spaces, a flexible lower level, and a backyard made for gathering, this well-appointed ranch offers room for everyone to live comfortably, entertain often, and enjoy every season together.

14167 Parliament Dr, Chesterfield
17711 Birch Leaf Ct, Chesterfield
$949,000
ACTIVE Status ⋅ Jill Lich
New Improved Price! Nestled on a quiet cul-de-sac in the highly sought-after Wildhorse subdivision, this stunning atrium ranch sits on a premium wooded lot and offers a backyard retreat rarely found in today's market. The show-stopping outdoor living area features a sparkling PebbleTec pool, inground trampoline, expansive entertaining spaces, and exceptional privacy surrounded by mature trees. Inside, the vaulted great room with a masonry gas fireplace opens seamlessly to two maintenance-free decks overlooking the resort-like backyard. The beautifully updated kitchen showcases granite countertops, a center island, gas cooktop, stainless appliances, and a sunny breakfast room and sitting area. The main level includes three bedrooms, highlighted by a spacious primary suite with a custom walk-in closet and luxurious vaulted bath. The professionally finished walkout lower level adds tremendous living space with a large family room, bedroom with walk-in closet, updated bath, full bar/kitchenette, exercise room, and potential fifth bedroom. An oversized three-car garage, newer roof, irrigation system, and security system complete the package. Enjoy all the amenities Wildhorse is known for, including pools, tennis courts, and scenic walking trails. Virtual Furniture Staging is Displayed in some of the Rooms.

17711 Birch Leaf Ct, Chesterfield
17915 White Robin Ct, Chesterfield
$1,299,000
ACTIVE Status ⋅ Jeff Lottmann
Set on a quiet cul-de-sac in the prestigious Greystone neighborhood, 17915 White Robin Court is a beautifully built Hayden Homes two-story offering more than 5,000 square feet of finished living space. Meticulously maintained and spotless throughout, the home offers impressive scale while still feeling warm and comfortable. A dramatic two-story foyer with volume ceilings creates a beautiful first impression, with extensive millwork, recently refreshed hardwood floors, and 9-foot ceilings on all three levels adding character throughout. The updated kitchen features 42-inch cabinetry, quartz countertops, JENNAIR double ovens, generous workspace, and an easy flow into the family room, where custom illuminated bookcases provide another layer of architectural detail. A formal dining room is ideal for entertaining, while the oversized laundry room adds exceptional everyday functionality. Upstairs, the spacious primary suite features a large private bath and impressive walk-in closet. Three additional bedrooms include two connected by a Jack-and-Jill bath and another with its own ensuite. The outdoor setting is one of the home’s standout features. A screened-in patio with ice/serving and beverage cooler overlooks the Baker pool and park-like, fully fenced backyard. An outdoor fireplace creates another inviting place to gather, while the yard extends well beyond the pool with mature surroundings, privacy, and plenty of green space to enjoy. The finished lower level adds even more versatility with a fifth bedroom, full bath, recreation space, and dedicated workout room. Additional highlights include zoned HVAC and a side-entry garage with epoxy-coated flooring. Located in the Rockwood School District with neighborhood access to Chesterfield Elementary, this exceptional Greystone home brings together quality construction, generous living spaces, outstanding outdoor amenities, and the unmistakable care of a home that has been exceptionally well maintained.

17915 White Robin Ct, Chesterfield
1843 Shadywood Ct, Chesterfield
$699,000
ACTIVE Status ⋅ Christi Miceli
*** OPEN HOUSE - SUNDAY, OCTOBER 11 FROM 1-3 PM *** GET READY TO FALL IN LOVE WITH THIS CHESTERFIELD BEAUTY! YOU WILL BE AMAZED AT THE UPDATES TO THIS TRUE SIX BEDROOM, FIVE FULL BATHROOMS AND 1.5 STY HOME WITH AN AMAZING LOCATION AND YOUR OWN PRIVATE POOL! NEWER MULTI-ZONE HVAC SYSTEM AND WATER HEATER. UPDATES SERVICE PANEL. FRESHLY PAINTED AND GORGEOUS FLOORING THROUGHOUT. UPDATED KITCHEN FEATURES NEWER STAINLESS APPLIANCES AND GRANITE COUNTERTOPS. MAIN FLOOR LAUNDRY (WASHER AND DRYER STAY) THE SPACIOUS LOWER LEVEL OFFERS TWO BEDROOMS AND TWO FULL BATHS AND A FAMILY/RECREATION AREA. THE UPPER LEVEL FEATURES TWO BEDROOMS AND FULL BATH. THE PRIMARY SUITE FEATURES GENEROUS CLOSET SPACE. SO MANY QUALITY UPDATES!! REFRIGERATOR AND FREEZER IN GARAGE STAY. TRULY AN OUTSTANDING HOME!

1843 Shadywood Ct, Chesterfield
1009 Savonne Ct, Chesterfield
$1,530,000
ACTIVE Status ⋅ Tamara Byrd
Looking for a new home for the Holidays? You must see this 1 1/2 story private oasis nestled on a 1.03-acre level lot close to Chesterfield Valley and other shopping, restaurants, and entertainment venues. The 2-story foyer welcomes you with marble flooring and elegant, curved staircase. The front room can be transformed into a home office, den, library, or whatever your heart desires. The main floor master bedroom suite with 2 walk-in closets, a sitting room and fireplace (need I say more) is the perfect sanctuary after a long day. Each of the three upper bedrooms has its own private, full bath and walk-in closets. Enjoy a soothing view of inground pool and lavish backyard from great room. The kitchen, which opens into the cozy hearth room, is a chef's delight with a walk-in pantry, newer electric stovetop and downdraft, newer electric convection oven, and microwave. The finished walk-out lower level is an entertainer's dream with limitless possibilities. It boasts an extra bedroom, wet bar, kitchenette, media room with built in riser, recreational area(s), double sided fireplace, and plenty of storage space. The scenic, large, level backyard boasts a patio with pergola, gas tiki torches, gas firepit, inground saline pool for those warm summer days, and a relaxing, soothing hot tub for those chilly nights. Inground sprinkler system.

1009 Savonne Ct, Chesterfield
15250 Kingsman Cir, Chesterfield
$535,000
ACTIVE UNDER CONTRACT Status ⋅ Aaron Wilson
Welcome to 15250 Kingsman Circle—a move-in-ready Chesterfield home tucked on a quiet cul-de-sac in the highly sought-after Parkway School District. With extensive updates, flexible living spaces, a finished lower level, and your own private pool, this home offers an exceptional combination of comfort, convenience, and recreation. Inside, the bright and welcoming main level offers generous living and dining spaces designed for both everyday life and entertaining. A custom built-in bar, completed in 2026, creates a stylish gathering spot, while renovated bathrooms and a thoughtfully added hall closet/mudroom bring modern function to the home. The finished lower level, renovated in 2025, significantly expands the home’s living space and includes a versatile bonus room—ideal for a home office, guest space, playroom, fitness area, or media room. Outside, skip the crowded community pool and enjoy summer at home with your own private pool, featuring a new liner (2025) and pool pump (2026). A wired outdoor TV setup makes it easy to catch the game poolside, entertain friends, or unwind on a summer evening. Major improvements have already been completed, including a new HVAC system, front door, and garage door in 2025, allowing the next owner to move in and enjoy the home rather than inherit a long project list. Located in the heart of Chesterfield with convenient access to shopping, restaurants, parks, highways, and Parkway schools, 15250 Kingsman Circle delivers the space, updates, location, and amenities that make everyday living easy. Come see everything this home has to offer.

15250 Kingsman Cir, Chesterfield
1224 Patchwork Flds, Chesterfield
$1,950,000
ACTIVE Status ⋅ Mary Krummenacher
Homes like this rarely become available in Fienup Farms—and this one is just two years new, extensively upgraded, meticulously maintained, and truly move-in ready. Set on a premium walkout lot, this exceptional Chesterfield home offers a rare opportunity to enjoy the look and feel of custom new construction without the wait. From the moment you enter, the difference is evident. An abundance of windows fills the home with natural light, creating bright, open living spaces and a beautiful connection to the outdoors. Engineered hardwood floors, oversized solid-core doors, and curated lighting add to the sophisticated yet welcoming feel. The main level flows beautifully from the formal dining room to the expansive great room and inviting hearth room, all centered around a showpiece chef’s kitchen with quartzite countertops, professional appliances, extensive custom cabinetry and a beautifully appointed butler’s pantry. Integrated Sonos speakers add another layer of effortless living and entertaining. The primary suite feels like a private luxury retreat, a two-person shower, soaking tub, dual vanities and separate custom-organized closets. Even more unusual, each additional main-level bedroom has its own ensuite with a zero-entry shower and designer finishes—providing exceptional comfort, privacy and accessibility. The walkout lower level extends the living space beautifully, offering an additional bedroom and full bath, generous entertaining areas and an abundance of storage, with additional space offering flexibility for future expansion. Natural light continues into the walkout level, giving the space a bright, inviting feel and making it a true extension of the home rather than simply a lower level. Outside is where this property becomes even harder to replicate. The sellers made a substantial investment in a new heated saltwater pool and custom fencing, transforming the backyard into a private outdoor retreat that is already completed and ready to enjoy. The premium lot still provides plenty of surrounding yard space for recreation, pets and outdoor activities—an increasingly rare combination of pool, usable yard and privacy. Then there is the Fienup Farms lifestyle. Residents enjoy a large lake, scenic walking trails, pickleball courts and playgrounds, while included landscaping—mowing, fertilizing, mulch and trimming—and snow removal provide the ease of low-maintenance living. Nearly new. Exceptionally upgraded. Light-filled. Heated saltwater pool already in. Custom fencing already completed. Meticulously maintained and truly move-in ready. In a community where opportunities like this are few and far between, this is the kind of home buyers wait for—and rarely find.

1224 Patchwork Flds, Chesterfield
1212 Walnut Hill Farm Dr, Chesterfield
$1,639,000
ACTIVE UNDER CONTRACT Status ⋅ Tammy Degenhardt
3.1 acres on a cul-de-sac, gunite saltwater pool with automatic cover, elevator, and side-entry OVERSIZED DEEP 4-car garage. A RARE SECOND OPPORTUNITY -- NOW EVEN BETTER. Price repositioned with a $161,000 reduction. Original structure was built in 1975 with 2 major additions, making the home 6712 total square ft of living space currently. Amazing opportunity to own this one-of-a-kind custom, stunning home 3 acres in a spectacular Chesterfield location, cul-de-sac and backing to woods. Features include soaring ceilings in the entry, living room, dining room, primary suite and primary bath. Walls of windows flood the home with natural light. The custom chef's kitchen with Viking Professional appliances, 8 1/2 foot movable island. Open flow to the hearth room with built-in shelving and a fireplace, perfect for gathering with family and friends. Off the kitchen a brand new composite deck with soffits and guttering. The main floor has two bedrooms with custom closets. The main floor full bathroom with luxurious walk-in shower featuring both a rainfall showerhead and a convenient handheld shower wand. Laundry room on the main level. Living room, family room and half bath also on the main level. Upstairs the primary suite is pure luxury with gas fireplace, sitting area, deck to have your morning coffee and watch the sunrise. The primary bath with soaring ceilings, lots of natural light, walk-in shower, separate jetted tub, 9 1/2 ft. double vanity. The next bedroom on 2nd floor has custom closets and "it's own" new composite deck with soffits and guttering, overlooking the pool. The bath has a NEW beautiful walk-in shower with incredible rainfall showerhead and a handheld wand as well, an adult-height double vanity. Third floor has a bedroom/bonus room with built-in shelving, sitting area and a large window that overlooks the back yard. This home has a total of 5 fireplaces. New closet systems. Large finished walkout lower level with family room, rec room w/bath that would work well as in-law quarters. Inviting exercise room featuring a wall of windows overlooking the beautifully landscaped backyard, bringing in an abundance of natural light. Full bath with walk-in shower. Sunroom that's perfect for hosting pool parties. Gunite saltwater pool with automatic pool cover. Fenced yard, perfect for your pet, circle drive, side-entry 4-car garage with new polyaspartic flooring. Elevator, ADA features, home security system and ring camera system. Ultraviolet Air System, Custom windows and doors. Art pieces commissioned by local artist, Brother Melvin Meyer in three separate locations throughout the house. This is a truly MUST SEE custom estate you won't want to miss.

1212 Walnut Hill Farm Dr, Chesterfield
220 Woodcliffe Place Dr, Chesterfield
$1,250,000
ACTIVE Status ⋅ Marie Kutryb
This stunning two story offers 6 bedrooms, 4.5 baths, and more than 5,500 square feet of beautifully designed living space. Situated on a private lot with a secluded backyard, the property features a sparkling saltwater pool, abundant natural light, and thoughtful updates throughout. The main level showcases a dreamy kitchen including Custom cabinetry, solid surface countertops, walk-in pantry and stainless steel appliances. A luxurious primary suite complete with a spa-inspired bathroom and two spacious walk-in closets. The inviting great room features a gas fireplace and large windows that fill the home with natural light. rounds out the main floor. Upstairs, you'll find a massive loft area along with four generously sized bedrooms, including one bedroom with a private ensuite bath and two bedrooms connected by a Jack-and-Jill bathroom. The finished walk-out lower level is ideal for entertaining, offering a built-in bar, a sixth bedroom, and a full bath, providing excellent space for guests or multigenerational living. Recent Updates Include: Roof (2025) Siding (2026) New pool equipment (2023) Vent hood (2026) Garage doors (2021) Deck flooring, stairs, and railing (2026) With spacious living areas, extensive updates, and resort-style outdoor amenities, this home offers the perfect blend of luxury, comfort, and functionality.

220 Woodcliffe Place Dr, Chesterfield
1577 Kehrs Mill Rd, Chesterfield
$2,900,000
ACTIVE UNDER CONTRACT Status ⋅ Catherine Shaw-Connely
An EXQUISITE EQUESTRIAN ESTATE nestled in the woods amongst 14+/- scenic rolling acres in Chesterfield along Kehrs Mill Road! Idyllic & rare, this extraordinary estate features a sprawling, custom designed 4,125 sq ft, 7 bedroom, 3 full & 1 half bath, pool, pool house, barn, 1 paddock, 1 pasture, and workshop! 2 story home w/impressive architectural detail, original wood flooring & abundant windows allowing expansive views of the lavish acreage! Perfect location for your dream home, a contemporary farmhouse, or even a country estate. Within the Rockwood School District with easy access to Hwy 40/64, shopping, dining, and Chesterfield Valley amenities. ALL buildings are being sold "as is", NO Seller's Disclosure available. DUPLICATE LISTING OF MLS#25026775.

1577 Kehrs Mill Rd, Chesterfield
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Listings courtesy of Mid America Regional Information Systems Internet Data Exchange as distributed by MLS GRID.


Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker of MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some listings have been excluded from this website.


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