Chesterfield Real Estate Search

Chesterfield 5 Bedroom Properties for Sale

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Newest Chesterfield 5 Bedroom Properties for Sale

216 Trailtop Ct, Chesterfield
$570,000
5 Beds ⋅ 4 Baths ⋅ 26065563 MLS ⋅ ACTIVE Status
Incredible Home with TWO PRIMARY SUITES! One on the main level and another on the upper level. This home has so much to offer including but not limited to the following: 30 year architectural roof, Insulated garage, Brazilian Hard wood deck, "Dana King Design Build" Remodeled kitchen, Brazilian Ipe hardwood floors on the main level, Upper level primary bath remodel, HVAC 5 year young, finished walk out lower level. All of this beauty sits on a large half acre culdesac lot backing to trees. Exterior of the home is mostly brick with elegant curb appeal. Remodeled kitchen includes Amish cabinetry, quartz counter, farmhouse sink with touchless faucet, built in china cabinet with tv insert & lighting, double oven, counter microwave, center island and breakfast table, built in private dining area for pets, unique backsplash, brazilian ipe hardwood floors, large picture window and so much more. Main level includes the remodeled kitchen, separate dining room, greatroom with decorative fireplace, primary bedroom and bath, and a front living room perfect for game night, entertaining, or even a home office. Upper level has 3 bedrooms and a nursery/sitting room. The 4th bedroom was opened and connected to the primary bedroom. Lower level is a finished walkout with a large rec room and bar/counter space. Home has easy access to highways yet tucked away in private haven. So much to love. Come check it out. FYI.... two HOA. $100 annual to Green Trails and $250 annual to the master Ladue Woods.

216 Trailtop Ct, Chesterfield

2 Fairlake Dr, Chesterfield
$2,295,000
5 Beds ⋅ 6 Baths ⋅ 26064265 MLS ⋅ ACTIVE Status
Set on a private, one-acre lot adjacent to Forest Hills Country Club and ideally situated near the clubhouse and first hole of the championship golf course, this exceptional custom-built ranch offers an extraordinary combination of elegance, scale, privacy and lifestyle. Built in 2012, the residence features 5 bedrooms, 6 bathrooms and approximately 5,910 square feet of finished living space, thoughtfully designed for both refined entertaining and comfortable everyday living. The main level welcomes you with soaring ceilings and an impressive sense of volume throughout. The open yet sophisticated floor plan includes a stunning kitchen with adjoining hearth room, spacious great room, formal dining room, private office, convenient main-level laundry and mud room, and an expansive primary suite with luxurious bath. A second main-level bedroom with ensuite bath provides an ideal private retreat for guests or family. The walk-out lower level is equally impressive, featuring tall ceilings, three additional bedrooms, three bathrooms, and a spacious family/media room. A dedicated sport court provides an exceptional amenity for recreation and fitness. The lower level opens directly to an expansive stone patio, complete with fireplace—an inviting setting for outdoor entertaining, relaxing evenings and gatherings with family and friends. Outdoor living is beautifully integrated throughout the home, with an elevated deck off the main level and a screened-in porch overlooking the private, tree-lined grounds. Mature trees surround the property, creating a peaceful sense of seclusion while maintaining an enviable proximity to the country club and golf course. An oversized three-car garage provides abundant space for vehicles, recreational equipment and storage. Every aspect of this custom residence reflects thoughtful design, quality construction and an exceptional attention to detail. A remarkable opportunity to own a premier one-acre property in one of the area's most desirable golf course settings.

2 Fairlake Dr, Chesterfield

1723 Millstream Dr, Chesterfield
$790,000
5 Beds ⋅ 5 Baths ⋅ 26065094 MLS ⋅ ACTIVE Status
Nestled on a quiet cul-de-sac lot backing to mature trees, this gorgeous open-concept ranch offers the perfect blend of elegance, comfort, and natural beauty. From the moment you step inside, you’ll be captivated by the soaring vaulted ceilings, expansive wall of windows overlooking the peaceful wooded backyard, and light-filled living spaces. The impressive great room features a dramatic floor-to-ceiling brick fireplace, skylights that fill the space with natural light, and gleaming wood floors. Designed for both everyday living and entertaining, the gourmet kitchen boasts two oversized islands, stylish modern chandeliers, abundant cabinetry, a double oven, pantry, and beverage refrigerator. The adjoining breakfast room is surrounded by windows and offers direct access to the composite deck—an ideal spot for outdoor dining and entertaining. The spacious primary suite features a large picture window framing serene wooded views and a beautifully updated luxury bath complete with a walk-in shower, elegant clawfoot soaking tub, and double vanity. A second generously sized bedroom with an en-suite bath and large closet, convenient main-floor laundry, and a half bath complete the main level. The open staircase leads to an expansive lower-level family room featuring another stunning brick fireplace, a wall of windows with a walkout door, crown molding, and recessed lighting. Three additional spacious bedrooms offer large picture windows, ample closet space, and ceiling fans, providing plenty of room for family, guests, or a home office. Additional highlights include a three-car garage, abundant lower-level storage, and a large, level side yard offering even more outdoor possibilities. With its beautiful architectural details, spacious layout, abundant natural light, and tranquil wooded backdrop, this exceptional home offers a rare combination of style, space, and privacy.

1723 Millstream Dr, Chesterfield

17915 White Robin Ct, Chesterfield
$1,299,000
5 Beds ⋅ 5 Baths ⋅ 26062792 MLS ⋅ ACTIVE Status
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

823 Silver Buck Ln, Chesterfield
$1,299,000
5 Beds ⋅ 5 Baths ⋅ 26059085 MLS ⋅ ACTIVE Status
GREAT NEW PRICE!! This beautifully appointed 1.5-story home combines generous living spaces, thoughtful upgrades and a setting designed to be enjoyed. From the moment you enter, the home feels bright and inviting, with a spacious 2-story great room framed by a wall of windows, custom lighting and an easy connection to the dining area and foyer. Durable LVP flooring flows through the main living areas, creating a cohesive feel while offering everyday practicality. At the heart of the home, the kitchen delivers both style and function with quartz countertops, a custom tile backsplash, center island, upgraded cabinetry with crown molding, double ovens, built-in microwave, stainless dishwasher, recessed lighting and a walk-in pantry. The adjoining breakfast room adds even more flexibility with custom built-ins featuring glass-front cabinetry and crown molding, plus a slider leading directly to the new composite deck. The main-level laundry room is equally well appointed with built-in cabinetry, marble countertop, wash tub and folding area. Upstairs, the spacious primary suite offers a peaceful retreat with a bay window and dual walk-in closets with custom organizers. The primary bath features a tiled floor, double-sink vanity, walk-in shower, freestanding soaking tub and private commode area. Three additional bedrooms provide generous space and walk-in closets, complemented by a Jack-and-Jill bath and an additional full bath for added convenience. The walk-out finished lower level gives the home another dimension, featuring a large family room with recessed lighting and built-in speakers, a fifth bedroom with walk-in closet and a full bath with walk-in shower. Whether used for guests, movie nights, recreation or simply spreading out, this level offers valuable additional living space. Outside, the fenced backyard and level lot backing to trees create a private setting for outdoor living and entertaining. The new composite deck provides an inviting space to relax or gather, with stairs leading directly to the lower-level patio for easy access between outdoor living areas. A concrete driveway leads to the oversized three-car garage, while an electric vehicle charger adds modern convenience. Zoned HVAC with air purifiers provides additional comfort throughout the home. A versatile floor plan, extensive storage, upgraded finishes and a peaceful outdoor setting come together in a home that offers the space and flexibility today’s lifestyle demands. And when it’s time to venture out, this home puts the best of the Chesterfield area within easy reach, with Chesterfield Valley, premier shopping and dining, parks, and convenient highway access just minutes away.

823 Silver Buck Ln, Chesterfield

1768 Orchard Hill Dr, Chesterfield
$649,900
5 Beds ⋅ 3 Baths ⋅ 26057026 MLS ⋅ ACTIVE Status
BACK ON MARKET NO FAULT OF SELLER. Luxury lakefront living in the highly sought after Baxter Lakes neighborhood in the heart of Chesterfield! This completely updated five bedroom, three bath ranch offers over 3,700 square feet of beautifully finished living space, an open floor plan, and breathtaking views overlooking two lakes. Beautiful LVP flooring flows throughout the main living areas, where a fireplace creates a warm and inviting focal point. The stunning kitchen is designed for both everyday living and entertaining with an oversized island, gorgeous quartz countertops, stainless steel appliances, and plenty of space to gather. The primary suite feels like a private retreat with its own beautifully updated en suite bath, walk-in closet, and an oversized sliding glass door that fills the room with natural light and allows you to wake up to the peaceful views just outside. The thoughtfully designed main level also features a private office, main floor laundry and a butler’s pantry, new windows, beautifully tiled bathrooms, modern finishes, and thoughtful updates throughout. The completely finished lower level is an incredible extension of the home, offering a spacious second living and entertaining area anchored by a cozy fireplace, three versatile bonus rooms ideal for a home gym, playroom, hobby room, additional office, or guest space, and generous storage without sacrificing finished living space. Step outside onto the expansive deck and take in the peaceful lake views from the large, private backyard surrounded by mature trees. Baxter Lakes offers beautiful walking trails and an incredible natural setting where deer, birds, and other wildlife are frequent visitors, including a resident owl that returns to the tree out back each year to raise her owlets. Enjoy the tranquility and privacy of a setting that feels like a retreat while remaining just minutes from shopping, dining, entertainment, and major highways. Located in the highly sought after Parkway School District, this is more than a beautifully updated home, it is a lifestyle that is incredibly difficult to replicate. With over 3,700 square feet of finished living space, a fully finished lower level, incredible lake views, and the perfect combination of space, style, privacy, and convenience, this is a rare opportunity to own a home you will love coming home to.

1768 Orchard Hill Dr, Chesterfield

184 Gunston Hall Ct, Chesterfield
$624,900
5 Beds ⋅ 4 Baths ⋅ 26055713 MLS ⋅ ACTIVE Status
Timeless Colonial style home with classic brick elevation and traditional symmetry, thoughtfully expanded for modern living. Classic design meets everyday comfort in this beautifully maintained home featuring a spacious tiled entry foyer, flanked by formal living and dining rooms—perfect for both entertaining and flexible living. The kitchen offers rich dark wood cabinetry and solid surface countertops, flowing seamlessly into the inviting den anchored by a wood-burning fireplace with brick surround. A convenient powder room sits just off this space. Sliding doors lead to a large patio overlooking a level, private backyard surrounded by mature trees—ideal for outdoor living and relaxation. The main level also includes a generously sized laundry room with service door to the backyard and access to the rear-entry 2-car garage. Upstairs, you’ll find FIVE spacious bedrooms, including an owner’s suite with private bath and dual closets. A full hall bath with tub/shower and linen closet serves the additional bedrooms. The partially finished lower level expands your living space with a large rec room, kitchenette area, and two additional rooms perfect for a home office, craft room, or hobbies. Nestled on a quiet cul-de-sac in a desirable location with top-rated schools, this home offers space, privacy, and a traditional layout designed for today’s lifestyle. HSA Home Warranty being offered to new buyer for extra peace of mind.

184 Gunston Hall Ct, Chesterfield

1224 Patchwork Flds, Chesterfield
$1,950,000
5 Beds ⋅ 5 Baths ⋅ 26048658 MLS ⋅ ACTIVE Status
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

1278 Harvester Dr, Chesterfield
$1,179,000
5 Beds ⋅ 5 Baths ⋅ 26052914 MLS ⋅ ACTIVE Status
Exceptional McBride-built 1.5 Sty located in the premier Chesterfield community of Fienup Farms. This popular “Pin Oak” model features an open light-filled layout with soaring ceilings, detailed trim work and large windows that offer continuous wooded views throughout the home’s interior. Welcoming covered front porch leads to formal dining room and stunning great room highlighted by a dramatic wall of windows. Designer kitchen with 42” white Shaker cabinetry, Helix quartz countertops, premium stainless steel appliances & 7’ center island adjoins bright breakfast room with sliding glass door that opens to deck. Spacious primary bedroom suite with luxury bath offers an appealing retreat. The 2nd floor extends the living quarters with 3 additional bedrooms, 1 with ensuite bath & 2 with Jack n’ Jill bath. The walk-out Lower Level provides an ideal space for both everyday living and effortless entertaining with an expansive recreation room & game room plus office, hot stone steam sauna, 5th bedroom and full bath. Situated on a premium wooded lot with composite deck, covered & open flagstone patios surrounded by built-in seating, fully fenced backyard & oversized 3-car garage with Tesla EV charger. Fienup Farms offers a vibrant lifestyle with 26-acre lake, pickleball courts, playgrounds, walking trails and beautifully maintained green spaces. Award-winning Rockwood School district.

1278 Harvester Dr, Chesterfield

2251 Whitby Rd, Chesterfield
$845,500
5 Beds ⋅ 3 Baths ⋅ 26049810 MLS ⋅ ACTIVE Status
**New & improved Price!** Masterfully renovated from top to bottom, this exceptional custom brick Colonial offers a rare opportunity to own a truly turnkey luxury home on nearly one acre in one of the area's most sought after neighborhoods. This remarkable residence delivers an effortless balance of sophistication, comfort, and everyday livability. From its stately curb appeal to its thoughtfully curated custom interiors, every detail has been carefully selected to create a home that is as impressive as it is welcoming. Inside, a gracious traditional floor plan unfolds with beautifully proportioned living spaces designed for both elegant entertaining and comfortable daily living. Rich engineered hardwood flooring extends throughout the main and upper levels, while abundant natural light fills every room through large new windows. The inviting family room is anchored by exquisite millwork, a stunning fireplace, and a beautifully appointed bar with mini fridge, creating the perfect gathering space. Expansive double sliding glass doors open to the impressive patio, seamlessly blending indoor and outdoor living. The heart of the home is a spectacular custom chef's kitchen designed to satisfy both the passionate cook and the avid entertainer. Custom built soft close cabinetry, quartz countertops, premium stainless steel appliances, designer tile backsplash, under cabinet lighting, and exceptional craftsmanship create a space that is equal parts beautiful and functional. The adjoining breakfast room, complete with its own fireplace, offers a warm and inviting setting for casual meals, while a separate dining room is perfect for more formal occasions such as dinner parties or hosting the family for the holidays. A spacious mudroom and main floor laundry area provide everyday convenience, while an additional main level room offers outstanding flexibility as a private home office, guest bedroom, second laundry room, or an extraordinary butler's pantry- This space can easily be customized to your family's needs. The private backyard is a peaceful extension of the home, offering nearly an acre of beautifully maintained grounds backing to common ground and surrounded by mature trees. The space feels private and upscale while still being close to all of the amenities that Chesterfield has to offer. Whether hosting family and friends, enjoying summer evenings on the expansive recently landscaped patio, or simply relaxing in complete privacy, the outdoor space provides the perfect setting for every occasion. The luxurious primary suite serves as a true retreat, offering generous proportions, abundant natural light, and ample space for both a king sized bedroom set and a comfortable sitting area. A custom solid wood walk-in closet system provides exceptional organization, while the beautifully renovated spa-inspired bathroom offers elegant finishes and a sophisticated atmosphere. Three additional spacious bedrooms and a beautifully updated bathroom with a double vanity finish out the second floor and continue the home's commitment to quality and timeless design. The finished lower level provides substantial additional living space ideal for a recreation room, media room, fitness area, game room, or guest accommodations. There is also a large unfinished area with additional laundry hookups. Perfect for storage or a second washer and dryer set. Extensively renovated with no detail overlooked, this extraordinary residence features new windows, a spectacular custom kitchen, three beautifully renovated luxury bathrooms, two stunning fireplaces, a finished lower level, and countless premium upgrades throughout. Combining timeless elegance, exceptional craftsmanship, and modern luxury in one of the area's most desirable locations, this is a rare opportunity to own a home where every space has been thoughtfully designed and every finish carefully selected. Simply move in and enjoy!

2251 Whitby 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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