Chesterfield Real Estate | Chesterfield 5 Bedroom Properties for Sale

5 Beds ⋅ 4 Baths ⋅ 26046683 MLS ⋅ COMING SOON Status

COMING SOON Fully updated this home is worth $1M+! RARE opportunity for a fixer upper in Chesterfield! Current owner is a contractor and willing to do the renovation for the buyer if they need someone.

2223 Twin Estates Cir, Chesterfield

$1,375,000

5 Beds ⋅ 5 Baths ⋅ 26047514 MLS ⋅ COMING SOON Status

Welcome to 823 Silver Buck Ln, an exceptional luxury residence nestled in the prestigious Silver Buck subdivision within the highly sought-after Bluff view community. Situated on a premium lot with outstanding curb appeal, this beautifully appointed home showcases quality craftsmanship, extensive upgrades, and an open-concept floor plan designed for both everyday living and elegant entertaining. Soaring ceilings, an upgraded staircase, and walls of oversized windows fill the spacious great room with an abundance of natural light, creating a warm and inviting atmosphere throughout. The gourmet kitchen is a chef’s dream, featuring custom cabinetry, premium stainless steel appliances, dual ovens, quartz countertops, and generous prep and storage space, while the spacious laundry room offers custom cabinetry for added functionality. The luxurious primary suite serves as a private retreat with bay windows overlooking the scenic bluff, a spa-inspired bathroom with granite countertops, a soaking tub, walk-in shower, and oversized walk-in closets. Additional bedrooms are generously sized and feature walk-in closets, including both a Jack-and-Jill bathroom and an attached en-suite bath, providing comfort and privacy for family and guests. The finished walkout lower level expands the living space with a large recreation area featuring a built-in speaker system, an additional bedroom with a walk-in closet, a full bathroom, abundant storage, and direct access to the backyard patio. The oversized three-car garage includes a built-in electric vehicle charger and a Wi-Fi-enabled garage door opener, adding modern convenience to this impressive home. Located within the award-winning Rockwood School District and just minutes from Chesterfield Valley, premier shopping, restaurants, parks, and Highway 40/I-64, 823 Silver Buck Ln offers the perfect combination of luxury, comfort, and an unbeatable location.

823 Silver Buck Ln, Chesterfield

$749,900

5 Beds ⋅ 4 Baths ⋅ 26045110 MLS ⋅ ACTIVE Status

Welcome to 2259 Sycamore Drive in sought after enclave in Chesterfield. This home offers the perfect blend of timeless character and everyday functionality. 5 spacious bedrooms, 3.5-baths, features beautiful hardwood flooring throughout the main level, creating a warm and inviting atmosphere from the moment you enter. The heart of the home is the welcoming family room, where a stunning Carrara marble fireplace is framed by an ornate custom built-in bookcase, creating an elegant focal point with timeless appeal. A second fireplace with matching built-in shelving anchors the finished lower-level recreation area, offering another inviting space for entertaining, relaxing, or gathering with family and friends. Enjoy the convenience of main-level laundry along with a bright sun room off of the kitchen. The walk out lower level features a full bar, entertainment space, along with an extra bedroom, full bathroom, study, and a wine cellar! The primary suite includes a luxurious soaking tub and separate shower. The oversized garage is large enough to fit 6 cars and has plenty of space for a workshop, storage, a RV and boat. Situated on a generously sized corner lot, the property offers plenty of outdoor space to enjoy. This exceptional home is ready for its next chapter. Don't miss the opportunity to own a spacious, well-appointed property with easy access to your every day needs!

2259 Sycamore Dr, Chesterfield

$1,149,900

5 Beds ⋅ 3 Baths ⋅ 26043533 MLS ⋅ ACTIVE Status

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. Blending timeless architecture with refined contemporary finishes, this remarkable residence delivers an effortless balance of sophistication, comfort, and everyday livability. From its stately curb appeal and professionally landscaped grounds to its thoughtfully curated 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. The inviting family room is anchored by exquisite millwork, a stunning fireplace, and a beautifully appointed wet bar, creating the perfect gathering space. Expansive 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 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. A spacious mudroom and 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 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. Whether hosting family and friends, enjoying summer evenings on the expansive 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 bath offers elegant finishes and a sophisticated atmosphere. Additional spacious bedrooms and a beautifully updated bath with a double vanity 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. Extensively renovated with no detail overlooked, this extraordinary residence features new windows, a spectacular custom kitchen, three beautifully renovated luxury bathrooms, 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. Join us for the open house on Thursday July 9th from 5:00pm-7:00pm to see this stunning home.

2251 Whitby Rd, Chesterfield

$2,000,000

5 Beds ⋅ 6 Baths ⋅ 26017344 MLS ⋅ ACTIVE Status

First showings on Saturday, 7/25 from 1-3pm. Homes of this caliber and level of finish, built as recently as 2023, rarely become available in Chesterfield, especially within the sought after Fienup Farms subdivision off Wild Horse Creek. Offering over 6,700 square feet, this residence presents a true opportunity to secure newer construction without the time, cost, or compromise of building. A striking interior unfolds with clean architectural lines, refined finishes, and a chef’s kitchen anchored by Wolf appliances, seamlessly connecting to the main living spaces. The layout is thoughtfully designed with a luxurious main floor primary suite, complemented by a private secondary ensuite on the opposite wing, ideal for guests or multigenerational living. A private office and formal dining room are positioned with intention, enhancing functionality while maintaining a seamless flow throughout the home. Upstairs, three spacious bedrooms and a generous bonus room provide flexible living and gathering spaces. The finished lower level expands the experience with extensive recreation areas and direct walkout access to an expansive patio. Outdoor living is equally considered, with a covered deck offering privacy and a relaxed setting overlooking the level backyard, well suited for a pool or curated outdoor living environment. A three car side entry garage completes the offering. For the buyer seeking newer construction without compromise, in one of Chesterfield’s most desirable settings, this is a rare and complete opportunity.

16936 Lake Mdw, Chesterfield

$525,000

5 Beds ⋅ 4 Baths ⋅ 26037558 MLS ⋅ ACTIVE Status

RIVER BEND ESTATES - MOVE IN READY / Parkway Schools / 5 Bedrooms, 3 1/2 Baths, Full walk-out basement. Two-Story on quiet cul-de-sac. Updates throughout include refinished hardwood floors, luxury vinyl flooring, updated light fixtures, freshly painted and refreshed bathrooms. Fenced yard backs to wooded common ground for private setting. Large composite deck perfect for entertaining or simply relaxing. Lots of wildlife for your viewing enjoyment including deer, turkey, racoons, foxes and birds. Basement is large and has lots of storage space, as well as a half bath. Oversized 2 car garage with storage room. Driveway is large enough to fit 6 cars. Plus, great neighbors! This is the listing agents' home.

166 Southdown Dr, Chesterfield

$950,000

5 Beds ⋅ 5 Baths ⋅ 26041581 MLS ⋅ ACTIVE UNDER CONTRACT Status

Open House Sunday 7/12, 1-3. Set on a beautifully landscaped 1.02-acre homesite with private lake access in the prestigious Chesterfield Meadow community, this distinguished all-brick estate offers a rare combination of timeless architecture, refined comfort, and resort-style living within the Rockwood School District. A sweeping circular drive creates a grand first impression, complemented by a side-entry garage and expansive parking designed to accommodate both everyday living and elegant entertaining. Inside, the home unfolds with generously scaled living spaces, a sophisticated neutral palette, and sunlit bay windows that bathe the interiors in natural light. The thoughtfully designed floor plan blends form and function, featuring a private main-floor guest suite, an adaptable formal living space ideal for a refined home office or sitting room, cheerful eat-in kitchen with granite counters and a well-appointed main-floor laundry. The updated primary suite offers a serene retreat, while spacious secondary bedrooms upstairs provide comfort and privacy for family and guests. Outdoor living is truly exceptional. A screened-in porch overlooks the tranquil lake and lush grounds, while the saltwater pool creates a resort-like setting perfect for both quiet relaxation and elevated entertaining. The finished walk-out lower level, complete with a full bath and dressing area, offers seamless access to the pool and grounds—ideal for hosting or extended stays. Designed to accommodate both intimate moments and grand gatherings, this residence delivers an unparalleled lifestyle in one of Chesterfield’s most desirable settings.

1868 Stenton Path, Chesterfield

$494,900

5 Beds ⋅ 2 Baths ⋅ 26032975 MLS ⋅ ACTIVE Status

Spacious story-and-a-half home featuring a main-floor primary bedroom suite plus 4 additional bedrooms on the upper level. Hardwood flooring throughout. Full bathroom on each floor. Eat-in kitchen with newer stainless steel appliances and separate dining room. Main-floor family room with gas logs, plus partially finished lower level with recreation room and HUGE storage/workshop area. Newer heating/cooling and water heater, brand new 200-amp electrical service. Oversized 2-car garage. Patio overlooks a spacious backyard. Conveniently located close (but not too close) to Hwy 141 and other major highways. Just minutes from hospitals, restaurants, supermarkets and retail. Parkway Central Schools (Green Trails).

44 Forestvale Dr, Chesterfield

$800,000

5 Beds ⋅ 5 Baths ⋅ 26040690 MLS ⋅ ACTIVE Status

Impeccably kept and ideally located, this exceptional villa offers more than 4,000 square feet of living space with a thoughtful, comfortable floorplan designed for both everyday living and entertaining. The updated kitchen serves as the heart of the home, while several newer windows bring in wonderful natural light throughout. Enjoy two gas fireplaces, inviting living spaces, and a nice rear patio that provides a great place to relax or entertain outdoors. The finished lower level adds valuable living area and flexibility for guests, hobbies, recreation, or a home office. Located in a secure villa community with a pool and desirable amenities, this home combines low-maintenance living with convenience to shopping, dining, parks, and major routes. Move-in ready and clearly cared for with pride, this is a fantastic opportunity to enjoy spacious villa living in a highly convenient setting.

15920 Picardy Crest Ct, Chesterfield

$729,000

5 Beds ⋅ 4 Baths ⋅ 26033374 MLS ⋅ ACTIVE Status

Welcome to 394 Branchport Drive in the highly sought-after Green Trails Estates! This stunning, move-in-ready ranch offers over 4,400 square feet of beautifully updated living space with 4 bedrooms and 3.5 baths. From the moment you walk in, you'll appreciate the fresh paint, updated lighting, new luxury vinyl plank flooring, and thoughtfully renovated bathrooms throughout. The heart of the home is the updated kitchen featuring brand-new stainless steel appliances, including a smart refrigerator, wine fridge, and gas stove—all included with the sale. The spacious floor plan flows seamlessly for both everyday living and entertaining. The finished lower level is an entertainer's dream, complete with a custom bar featuring a wine fridge, refrigerator, and dishwasher, plus plenty of space for game nights, gatherings, or movie marathons. A brand-new washer and dryer are also included. Major updates provide peace of mind, including a newer HVAC system, water heater, sump pump, smart toilets, and a roof replaced in 2006. Outside, you'll enjoy fresh landscaping and a private backyard perfect for relaxing or entertaining. Located in the award-winning Parkway School District and just minutes from shopping, dining, parks, and highways, this turnkey Chesterfield home offers the perfect blend of space, style, and convenience. Simply unpack and start enjoying everything this exceptional home has to offer!

394 Branchport Dr, Chesterfield

$499,900

5 Beds ⋅ 3 Baths ⋅ 26039469 MLS ⋅ ACTIVE Status

***HUGE Price Improvement!!! Seller says sell!! ***Updated ranch on a private, wooded lot! This spacious home offers an open and inviting floor plan with a fully finished walkout lower level featuring a full bath, large recreation room, custom marble-tile bar, and two versatile bonus rooms. Recent improvements include hardwood flooring, updated bathrooms, new bedroom carpeting, and a deck perfect for outdoor entertaining. The primary suite features a separate tub and shower, while maintenance-free vinyl siding and insulated thermal windows provide added value and efficiency. A rare combination of privacy, updates, and functional living space. This home is a must-see! Make your appointments today!

1272 Beaver Creek Rd, Chesterfield

$585,000

5 Beds ⋅ 4 Baths ⋅ 26037570 MLS ⋅ ACTIVE Status

Recently renovated 5 bedroom home boasting over 3600 total square feet in Parkway Central. Perfect for multi generational living including a walk-out basement with In-Law quarters, kitchen and wet bar! Private fenced in backyard backs to woods and has two-zone fencing to provide pets their own space. Main floor offers 2 separate family rooms, open kitchen and dining. Recent renovations to lighting and flooring throughout with modern accents in kitchen overhaul with beautiful quartz cabinets and all brand-new appliances. This home is turn-key and move-in ready, all of the details have been thoughtfully prepared for the right family. This neighborhood and location of East Chesterfield is quick proximity to Creve Coeur shops and restaurants that are some of the best in West County! Welcome home.

343 Ridge Trail Dr, Chesterfield

$1,450,000

5 Beds ⋅ 6 Baths ⋅ 26037315 MLS ⋅ ACTIVE Status

Opportunity to own a premium estate in Chesterfield’s highly coveted Dunhill Farm neighborhood are rare, but this exceptional property is truly in a league of its own. Situated perfectly on a sprawling, level 1.04-acre waterview lot, 2325 Sterling Pointe Drive delivers an exquisite blend of open, light-filled architecture and backyard resort living that discerning buyers spend years searching for. From the moment you step through the front door, the home’s stunning atrium ranch design captivates. An elegant foyer with classic marble floors introduces a soaring, bright floor plan framed by floor-to-ceiling Palladian windows, arched doorways, and custom built-ins. The main level is masterfully planned for both seamless entertaining and effortless everyday comfort, highlighted by a chef’s kitchen featuring rich natural cherry cabinetry, premium granite countertops, double ovens, and an oversized central island. The kitchen flows into a sunlit breakfast nook and a warm, inviting hearth room anchored by a handsome stone-and-brick fireplace. Tucked away on the main floor, the serene primary suite serves as a true private retreat, complete with detailed coffered ceilings, spacious walk-in closets, and a spa-like bath featuring a jacuzzi soaking tub and a separate walk-in shower. The lower level is a fully finished, walk-out destination all its own. Boasting sweeping 10-foot poured concrete ceilings, this massive footprint includes a large recreation room with its own cozy fireplace, a full wet bar, a dedicated exercise room, and an amazing home theater room designed for ultimate movie nights. Three additional guest bedrooms, each paired with their own private baths, provide complete comfort and privacy for family or multi-generational visitors. Step outside to discover a private backyard oasis that rivals a luxury resort. Whether you're relaxing under the covered patio, gathering around the built-in fire pit, or swimming laps in the pristine 40' x 20' in-ground pool, the level grounds offer an unmatched backdrop with peaceful views adjoining open ground and the neighborhood waterfront. Equipped with a three-car garage, zoned heating and cooling, and a full inground sprinkler system, this 5-bedroom, 5.5-bath estate spans over 6,570 square feet of total living space where no detail has been overlooked. Located in the top-rated Rockwood School District and just minutes from the area’s premier dining, boutique shopping, and recreation, this isn't just a home—it's your private everyday escape.

2325 Sterling Pointe Dr, Chesterfield

$739,900

5 Beds ⋅ 4 Baths ⋅ 26034383 MLS ⋅ ACTIVE Status

Back on Market, No Fault of Sellers. Welcome to this beautifully updated 5 bedroom, 3 bath home located in the highly sought after White Gate Farms Estates! Offering over 5,000+ square feet of living space, this stunning home has been thoughtfully updated from top to bottom and is truly move in ready. From the moment you step inside, you’ll appreciate the bright and open layout featuring fresh paint, sleek new flooring and an abundance of natural light throughout. The main floor offers plenty of space for both everyday living and entertaining, featuring a formal living room that can easily double as a home office, a cozy family room centered around a gas fireplace, a separate dining room and a convenient main floor laundry area. The fully renovated kitchen is truly the heart of the home, complete with custom cabinetry, granite countertops, stainless steel appliances and ample prep and storage space, making it perfect for family meals or hosting guests. Just off the kitchen, enjoy the bright and spacious sunroom that leads out to a large deck overlooking the beautifully landscaped backyard, professionally designed to create the perfect outdoor retreat for relaxing or entertaining. Upstairs, you’ll find five spacious bedrooms and two full bathrooms, including a private primary suite featuring a walk in closet, separate shower and jetted tub, creating the perfect place to unwind at the end of the day. The hallway bathroom is already plumbed for a double sink vanity, offering an easy opportunity for added functionality and convenience. Every vanity throughout the home has been updated, adding a fresh and modern touch. The finished lower level is an entertainer’s dream, offering a large rec room, sleek new theatre room and an additional half bath with a rough in already in place to easily convert it into a full bathroom, giving you even more flexibility and future potential. Conveniently located just minutes from top rated Parkway West schools, shopping, dining and major highways, this exceptional home offers the perfect blend of space, comfort and modern updates in one of the area’s most desirable neighborhoods. Do not miss your chance to make this one yours!

14901 Jockey Club Dr, Chesterfield

$999,900

5 Beds ⋅ 5 Baths ⋅ 26031012 MLS ⋅ ACTIVE Status

Discover a home that feels like a private retreat in the heart of Chesterfield. 15875 Kettington Road blends everyday comfort with resort-style amenities, offering the space, warmth, and lifestyle today’s families dream of. Set on a quiet street in one of West County’s most desirable neighborhoods, this beautifully maintained residence welcomes you with its new roof, bright open living spaces that is perfect for gatherings, celebrations, and the simple joy of being together. Sunlight fills each room, creating a warm, inviting atmosphere from the moment you step inside. The kitchen serves as the heart of the home — a functional, welcoming space ideal for weeknight dinners, weekend baking, and hosting friends and family. Generously sized bedrooms provide peaceful retreats, while the primary suite offers the privacy and calm every homeowner deserves. But the true magic of this property unfolds outdoors. Your Own Backyard Resort Step outside to a stunning in-ground saltwater pool, the centerpiece of a backyard designed for relaxation, fun, and unforgettable moments. Whether it’s summer barbecues, pool parties, or quiet evenings under the stars, this outdoor space elevates everyday living. While enjoying the pool you’ll find two full bathrooms off the patio, making pool days effortless and keeping the main home cool, clean, and dry. If you need a quite spot the attached pool house also has a large deck on the opposite side from the pool. A Full Pool House — Practically a Second Home The attached pool house expands the property’s versatility and value. It includes: A full kitchen A family room/living area A bedroom A laundry room A separate deck Perfect for hosting guests, creating a private in-law suite, giving teens their own hangout space, or even generating rental income. It’s a rare amenity that transforms the property into a true multi-generational or multi-use home. Location That Supports Your Lifestyle Just minutes from Chesterfield’s top-rated schools, parks, shopping, dining, and major commuter routes, this home offers the perfect balance of tranquility and convenience. It’s a place where you can grow, gather, and enjoy the best of West County living. 15875 Kettington Road isn’t just a home — it’s a lifestyle, a retreat, and a place where memories are made.

15875 Kettington Rd, Chesterfield

$499,000

5 Beds ⋅ 4 Baths ⋅ 26014129 MLS ⋅ ACTIVE Status

Welcome to this spacious and beautifully maintained villa located in the desirable Cedar Springs community in Chesterfield. This impressive home offers over 5,300 square feet of living space, featuring 5 bedrooms, 3.5 bathrooms, and a thoughtfully designed floor plan perfect for comfortable everyday living and entertaining. Step inside to discover expansive living areas, soaring ceilings, and abundant natural light. The great room features a cozy fireplace, creating a warm and inviting atmosphere for relaxing or hosting guests. The spacious kitchen flows seamlessly into the main living and dining areas, making gatherings effortless. The main-level primary suite offers a peaceful retreat with generous closet space and an en-suite bath. Additional bedrooms and living areas provide flexibility for guests, office space, or hobbies. A finished lower level adds significant living space ideal for a recreation room, media area, or additional entertaining space. Enjoy outdoor living with a private patio/deck, perfect for morning coffee or evening relaxation. The home also includes an attached garage, central heating and cooling, and low-maintenance living within a well-maintained community. Conveniently located near shopping, dining, parks, and major highways, and served by the highly regarded Parkway School District, this home combines comfort, space, and location in one exceptional property.

730 Willow Spring Hill Ct, Chesterfield

Chesterfield 5 Bedroom Properties for Sale

Newest Chesterfield 5 Bedroom Properties for Sale