Chesterfield Real Estate | Chesterfield Homes with a Pool for Sale

Discover this beautifully updated, stately two-story home in the heart of Chesterfield, offering five bedrooms, three bathrooms, and more than 4,000 square feet of finished living space. The homeowners have meticulously maintained and improved the property, blending elegance, functionality, and timeless appeal. Just inside, the formal dining room is on the left, while a sitting room or flexible home office is on the right. The family room features a wood-burning fireplace, a walk-behind bar, and newer hardwood floors. The eat in kitchen offers a generous amount of counter space, stainless steel appliances, a breakfast area, bay window and newer hardwood flooring. From the kitchen, step into a private backyard oasis with a fabulous pool—perfect for hot St. Louis summer days. Upstairs are five bedrooms, including an exceptionally spacious primary suite with a walk-in closet and a beautifully updated bathroom featuring marble tile. The four additional bedrooms offer tons of closet space and share an updated full bathroom. The finished lower-level features two separate recreation areas, new luxury vinyl flooring, fresh paint, and storage areas. Outside, the main event is the large private in-ground pool with a diving board, large pool deck, fresh landscaping, and a mini basketball court, all creating an ideal setting for an active and relaxing lifestyle. Additional features of this home include a main-floor laundry room, newer zoned HVAC (4 years) newer roof (10 years), a stately covered front porch, and side entry garage. Just minutes to major highways, shopping, top rated Parkway schools, you can’t beat the location and convenience. This beautiful home is ready for you to make it yours.

1372 White Rd, Chesterfield

$1,100,000

ACTIVE Status ⋅ Mitzie Fenberg

A truly special property where Tudor character meets resort-style living, tucked into a lush, wooded lot in one of the area's most private settings. This 4-bedroom, 3.5-bath home pairs a striking gabled façade, handsome brick accents and a richly textured shake-style roof with mature landscaping and a stacked-stone waterfall built into the hillside. Step inside to a soaring two-story foyer with a wraparound balcony, skylights and fluted columns. The great room features a brick fireplace and stained-glass transom windows — a detail that repeats throughout the home. French doors lead to a formal living room. The kitchen offers ornate custom cabinetry, solid-surface counters, a professional-grade range and a hand-carved butcher-block island, with a window over the sink framing the waterfall and pool beyond. A breakfast nook, a vaulted skylit sunroom and a main-floor laundry room finished with matching custom cabinetry round out the main level. The main-level primary suite includes its own gas fireplace and a spa-like bath: a corner soaking tub in a bay window, an oversized walk-in shower, dual vanities, a separate water closet and a stained-glass accent window. An exceptional walk-in closet boasts extensive custom built-ins, creating a beautifully organized dressing space with abundant storage. Upstairs, a second primary suite offers its own bath, dual closets and a private composite deck overlooking the grounds — ideal for guests or family. The finished lower level adds a spacious rec room and a custom wet bar with brass hardware and a mirrored back bar, built for movie nights and gatherings. Outside, a flagstone patio wraps a free-form pool, with the stacked-stone waterfall cascading into its own pond just steps away — all framed by mature trees and total privacy. The detached, heated 3-car garage connects to the home via a covered breezeway and hides a bonus: a finished upper loft with new luxury vinyl flooring, built-in storage and its own dedicated furnace — ideal as a home gym, hobby space or flex room. Central vacuum runs through both the home and garage. Architecturally distinctive and set on one of the most private lots around, this is a home that has to be walked through to be believed.

16463 Dapple Gray Ct, Chesterfield

$1,199,900

COMING SOON Status ⋅ Kimberly Jones

Welcome to 1109 Windridge Estates Lane, an exceptional residence set on a private 0.73 acre lot in the heart of Chesterfield. Offering approximately 6,000 square feet of meticulously finished space, this 5 bedroom, 4.5 bath two story home pairs refined interiors with resort inspired outdoor living. A beautifully renovated exterior accented by warm wood details and charming dormer windows creates striking curb appeal. Inside, a light filled grand foyer showcases a redesigned dual staircase and opens to an elegant formal dining room and dedicated office with designer built-ins. Crown molding, custom shutters and luxury vinyl plank flooring lend a polished aesthetic throughout the main level. Designed for entertaining, the inviting living room features a gas fireplace framed by shiplap, built-ins and a dramatic window wall. The spacious kitchen is appointed with a tiered center island and breakfast bar, stainless steel appliances, double wall ovens, walk-in pantry, butler's pantry and adjoining breakfast room with deck access. An impressive vaulted hearth room offers a second gas fireplace, built-in speakers and a wall of windows overlooking the backyard. Main floor laundry and an updated powder room add everyday convenience. Upstairs, the primary suite provides a serene retreat with tray ceiling, generous walk-in closet and spa inspired bath featuring dual vanities, heated floors, soaking tub and tiled shower. Three additional bedrooms include one with a dedicated ensuite bath and two connected by a shared bath, each offering a walk-in closet. The finished walkout lower level extends the home's versatility with a family room, recreation area, fifth bedroom, full bath and substantial storage, with direct access to the lower patio and exceptional outdoor amenities. Outside, a resort inspired retreat awaits. The expanded deck overlooks a heated inground saltwater pool, hot tub, covered pergola seating and fully fenced backyard, creating an enviable setting for entertaining, recreation and relaxation. An oversized side entry, 3 car garage, professional landscaping and irrigation system complete this distinctive Chesterfield residence with over $300k in owner investment. Ideally located within the award-winning Rockwood School District, just minutes from Chesterfield Valley shopping, dining and recreation with convenient access to Highway 40/64.

1109 Windridge Estates Ln, Chesterfield

$2,275,000

ACTIVE Status ⋅ Melinda McCarthy

This amazing contemporary home sets on an end cap lot in this gem enclave community of 35 homes. The home's location within the neighborhood not only affords the most privacy, and a view of the lake from its front Lanai and second floor covered porch but also provided the perfect location for its spectacular private Gunite courtyard pool built by Pool Tron. The courtyard pool was built to remain open year-round and features a Peacock paver brick patio and stairwells and provides a lovely year-round view from the interior of the home. The home is constructed from upgraded Nichiha panels, Stone veneer, Stucco and Hardie board. The owner is a professional designer which is easy to see with all the custom luxury features that were chosen for this home. Appliances include "48 Wolf range, a 48 " Subzero, Electrolux, and Cove. There are Hunter Douglas Vignettes and Silhouette Treatments thought out on the sliders, French doors and windows. The main floor features 7'8" French doors and the whole house has Luxury Lifestyle upgraded Pella windows. The second floor was designed as a secondary "private" primary suite with bedroom and open loft sitting area. The bathroom includes a makeup/office nook, and the space offers a panoramic view of the lake from the private upper covered veranda porch. The lower level is partially finished with a 9" basement pour and half bath plus all rough-ins (plumbing and electric) are in place for buyer to finish a custom wet bar to their own specifications. Vintage 1875 Brunswick pool table in lower level will stay. Seller has a bar plan designed by Beck and Allen and will provide it to buyer if they so desire. There is a security system and an EV car charger in the garage. There was extensive extra landscaping done including extra trees and bushes to take advantage of this premium lot and giving total privacy to the pool area. Also, the landscape and uplighting at night makes this home stand out. The location of this community is fabulous. Adjacent to two lakes, with parks, 4 recreational walking trails, the YMCA and the Chesterfield Amphitheater, The District and Chesterfield Commons, quick access to Hwy 64-40, retail and restaurants are all nearby. Most are within walking distance. This home is perfect for the buyer looking for exquisite finishes, privacy and easy accessibility to all the wonderful activities Chesterfield provides.

16529 Waterfront Ave, 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

$1,950,000

COMING SOON 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, with heated bathroom floors, 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. Additional upgrades include smart-home controls for thermostats, lighting, security and irrigation, along with numerous builder and post-construction enhancements. All appliances, including the washer and dryer, are included. 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

$1,800,000

ACTIVE Status ⋅ Tammy Degenhardt

Amazing opportunity to own this one of a kind, stunning home with 6712 sq. ft. of living space and over 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 chefs 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. 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 over looks 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 is perfect for hosting pool parties. Gunite saltwater pool with automatic pool cover. Fenced yard, perfect for your pet, inground sprinkler system, circle drive, side entry 4 car garage with new polyaspartic flooring. Elevator, ADA features, home security system and ring camera systems. 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

$770,000

ACTIVE UNDER CONTRACT Status ⋅ Michael Weiss

Stately two-story brick home on a lush, level lot with an incredible resort-style backyard and Roman-style pool is sure to capture your attention. Enter through the two-story foyer and be amazed by the care and exceptional condition of this home. The formal living and dining rooms are beautiful, featuring thick crown molding. The enormous family room offers built-in shelves, a gas fireplace, and an alcove area. The chef's kitchen features double ovens, stainless steel appliances, solid-surface countertops, an impressive island, abundant cabinetry, views of the backyard, and access to the incredible screened-in porch. The laundry room, with side-by-side units and a sink, is conveniently located just off the kitchen and attached two-car garage. Upstairs, the beautiful primary suite features hardwood floors, a walk-in closet, and a spacious bath with dual vanities, a jetted soaking tub, separate shower, and private water closet. Three additional generously sized bedrooms and a full bath provide plenty of space for family or guests. The finished lower level offers a half bath, two large finished living areas with built-in shelves and a desk, plus a separate bonus room, all perfect for hobbies, entertaining, or endless fun. The backyard is the true star, offering an incredible setting with a pristine pool, a sublime patio area, expansive green space, and outstanding natural privacy. Tours begin 7/29! Schedule your appointment today.

14046 Boxford Ct, 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

$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

Chesterfield Homes with a Pool for Sale

Newest Chesterfield Homes with a Pool for Sale