5 Bedroom homes for sale & real estate in Chesterfield, MO

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OPEN SUN, 1PM TO 3PMFLOOR PLAN

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
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 i

$595,000

5 beds3.5 baths3,897 sq ft

216 Trailtop Ct, Chesterfield, MO 63017

Insulated garage • Remodeled kitchen • Two primary suites

FLOOR PLAN

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
Exceptional privacy and effortless indoor-outdoor living await in this meticulously maintained California-style atrium ranch on 2.41 acres in the gated community of Chesterfield Lakes. Offering over 5,000 SF of living space, the spacious, open floor plan is filled with loads of natural light. A large courtyard creates a welcoming entrance, while a composite deck, two screened porches and patio provide inviting spaces to relax and enjoy the serene surroundings. The dining room shares a see-through fireplace with the inviting living room with wet bar and access to a screened porch, deck and backyard. The open kitchen features custom cabinetry, a center island and a generous breakfast room ove

$1,210,000

5 beds4 baths5,000 sq ft

56 Chesterfield Lakes Rd, Chesterfield, MO 63005

Gated community • Two screened porches • Large courtyard

FLOOR PLAN

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
Welcome to 17026 Kimwood Court, a spacious and inviting home in sought-after Chesterfield Estates offering more than 4,000 square feet of finished living space, a main-floor primary suite, and a versatile walkout lower level. The main level features generous living and entertaining spaces, including a light-filled great room, an adjoining sunroom, a formal dining area, and a large kitchen with abundant cabinetry and workspace. The primary suite offers the convenience of main-level living, while additional bedrooms provide flexibility for family, guests, or a home office. Downstairs, the finished walkout lower level expands the living space with a large recreation area, wet bar, additional s

$789,000

5 beds3.5 baths4,771 sq ft

17026 Kimwood Ct, Chesterfield, MO 63005

Wet bar • Adjoining sunroom • Large kitchen

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
MOTIVATED SELLER * * An Extraordinary Home. An Exceptional Opportunity. * * Discover The Grand Estate at Jockey Club, an impressive five-bedroom residence offering over 5,000 square feet of living space in the desirable White Gate Farms Estates community. Designed for both everyday comfort and exceptional entertaining, this home features a beautifully renovated kitchen, a newly finished basement with a dedicated movie theater room, and an inviting four-season room overlooking the beautifully landscaped backyard and oversized deck. Beyond these highlights, discover a private primary retreat, generous living areas, and thoughtful updates throughout that bring comfort, functionality, and

$715,000

5 beds3 baths4,960 sq ft

14901 Jockey Club Dr, Chesterfield, MO 63017

Private theater room • Four season room • Landscaped backyard

OPEN SUN, 1PM TO 3PMFLOOR PLAN

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
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 cu

$1,299,000

5 beds4.5 baths5,118 sq ft

17915 White Robin Ct, Chesterfield, MO 63005

Formal dining room • Two-story foyer • Screened-in patio

Property at 1723 Millstream Dr, Chesterfield, MO 63017, 5 beds, 4 baths

$790,000

5 beds4 baths4,502 sq ft

1723 Millstream Dr, Chesterfield, MO 63017

Property at 1768 Orchard Hill Dr, Chesterfield, MO 63017, 5 beds, 3 baths

$649,900

5 beds3 baths3,720 sq ft

1768 Orchard Hill Dr, Chesterfield, MO 63017

Property at 823 Silver Buck Ln, Chesterfield, MO 63005, 5 beds, 4.5 baths

$1,299,000

5 beds4.5 baths5,584 sq ft

823 Silver Buck Ln, Chesterfield, MO 63005

Property at 35 Arrowhead Estates Ct, Chesterfield, MO 63017, 5 beds, 4 baths

$1,630,000

5 beds4 baths4,469 sq ft

35 Arrowhead Estates Ct, Chesterfield, MO 63017

Property at 184 Gunston Hall Ct, Chesterfield, MO 63017, 5 beds, 3.5 baths

$624,900

5 beds3.5 baths3,340 sq ft

184 Gunston Hall Ct, Chesterfield, MO 63017

Property at 1278 Harvester Dr, Chesterfield, MO 63005, 5 beds, 4.5 baths

$1,179,000

5 beds4.5 baths4,527 sq ft

1278 Harvester Dr, Chesterfield, MO 63005

Property at 1224 Patchwork Flds, Chesterfield, MO 63005, 5 beds, 4.5 baths

$1,950,000

5 beds4.5 baths4,528 sq ft

1224 Patchwork Flds, Chesterfield, MO 63005

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
Meticulously maintained 10-year-old home on a fabulous one-acre lot in Town & Country! A two-story entry welcomes you to a spacious, open floor plan featuring hardwood flooring, 9-foot ceilings on main level and custom cabinetry. The kitchen offers a center island, granite countertops and generous cabinet space, while the inviting hearth room with a cozy fireplace provides the perfect place to unwind. A separate dining room is ideal for holiday gatherings and special occasions. A main-floor office creates an ideal quiet workspace. Upstairs, the spacious primary suite features a coffered ceiling, complemented by three additional bedrooms and a full bath. One bedroom currently serves as

$995,000

5 beds3.5 baths3,896 sq ft

12372 S 40 Dr, Saint Louis, MO 63141

One acre lot • Open floor plan • Two story entry

FLOOR PLAN

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
Finding a home with five true bedrooms, 3.5 bathrooms, a finished walkout lower level, a three-car garage and this level of renovation is rare. At 2414 Tuckahoe Circle, you get all of it in one beautifully finished and thoughtfully designed home. Offering approximately 3,400 square feet of finished living space, including 2,506 square feet above grade and an approximate additional 900 square feet in the lower level, this home has the room and flexibility to handle everyday life, entertaining, working from home and overnight guests without sacrificing style. The updates begin as soon as you step inside. Wide-plank LVP flooring, fresh neutral paint, updated lighting and carefully selected, pr

$509,000

5 beds3.5 baths3,411 sq ft

2414 Tuckahoe Cir, O Fallon, MO 63368

Redesigned kitchen • Dual hvac system • 0.27 acre lot

OPEN SAT, 1PM TO 3PM

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
Welcome to this stunning 5-bedroom, 4.5-bath Craftsman-style home situated on 4.22 beautiful acres, offering the perfect blend of space, comfort, and privacy! Surrounded by natural beauty and adjoining a wooded area, this property provides a peaceful setting with plenty of room to enjoy both indoor and outdoor living. Step inside to discover soaring ceilings, abundant natural light, and a spacious, thoughtfully designed floor plan. The inviting living room features a wood-burning fireplace, creating a warm and welcoming atmosphere. The eat-in kitchen offers generous cabinet space, all-electric appliances, and plenty of room for gathering, while a separate formal dining room provides the per

$1,350,000

5 beds4.5 baths4,870 sq ft

715 Madison Vly, Wildwood, MO 63005

4.22 acre lot • 3 garage spots • Built 2015

COMING SOON

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
An impressive brick, stone, and cedar exterior sets the tone for this fully reimagined estate, designed by Lauren Strutman Architects. The thoughtfully crafted open floor plan features well-proportioned rooms, wide-plank oak hardwood floors, contemporary lighting, and expansive windows that fill the home with natural light. A vaulted porch entrance, accented by timber trusses and a mahogany front door with beveled glass panes, welcomes you into an elegant oak-lined foyer. The formal dining room and library-paneled great room exude timeless sophistication, with a beamed ceiling, stone fireplace, and marble wine bar. The spacious family room, anchored by a dramatic floor-to-ceiling fireplace,

$2,495,000

5 beds4.5 baths7,174 sq ft

1824 Topping Rd, Saint Louis, MO 63131

Open floor plan • Stone fireplace • Beamed ceiling

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
Seller is offering a $5,000 credit to the buyer. A fresh start in established Glan Tai! Beautifully renovated by Rocklin Group, this spacious two-story sits on a . 38-acre lot and offers five bedrooms, three full baths, and 2,519 square feet of luxury. The updated eat-in kitchen features new cabinetry, quartzite countertops, stainless steel appliances, and generous storage. Renovated bathrooms, new flooring, and fresh paint carry the updates throughout. A main-floor bedroom and full bath offer flexibility for guests or a home office, with four additional bedrooms upstairs. Improvements include new HVAC, plumbing, vinyl windows, and an updated electrical panel, plus newer siding, soffit, fas

$539,900

5 beds3 baths2,519 sq ft

3 Leaside Ct, Manchester, MO 63011

Renovated home • New siding • New flooring

OPEN SUN, 1PM TO 3PM

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
Beautifully remodeled from top to bottom, this stunning 5-bedroom, 3-bath home offers 3,178 square feet of beautifully finished living space, thoughtfully updated with modern finishes while maintaining its inviting character! Gorgeous new hardwood flooring flows seamlessly throughout the main level, while oversized picture windows fill the home with an abundance of natural light. Step inside the welcoming foyer, which opens to a charming sunken living room and formal dining room, offering versatile spaces for relaxing, entertaining, or gathering with family and friends. Continue into the beautifully redesigned kitchen, featuring natural wood soft-close cabinetry, elegant white quartz counte

$519,900

5 beds3 baths3,178 sq ft

25 Leaside Ct, Manchester, MO 63011

Hardwood flooring • Remodeled • Formal dining room

Property at 258 Montecito Ter, Saint Peters, MO 63304, 5 beds, 3.5 baths

$575,000

5 beds3.5 baths3,038 sq ft

258 Montecito Ter, Saint Peters, MO 63304

Property at 55 Marsala Ct, Saint Charles, MO 63304, 5 beds, 3.5 baths

$409,000

5 beds3.5 baths3,208 sq ft

55 Marsala Ct, Saint Charles, MO 63304

Property at 33 Weldon Spring Heights Dr, Weldon Spring, MO 63304, 5 beds, 4 baths

$725,000

5 beds4 baths4,187 sq ft

33 Weldon Spring Heights Dr, Weldon Spring, MO 63304

Property at 12305 Wildlife Trl, Town And Country, MO 63141, 5 beds, 5.5 baths

$1,489,900

5 beds5.5 baths4,535 sq ft

12305 Wildlife Trl, Town And Country, MO 63141

Property at 16620 Wycliffe Place Dr, Wildwood, MO 63005, 5 beds, 4.5 baths

$1,350,000

5 beds4.5 baths6,340 sq ft

16620 Wycliffe Place Dr, Wildwood, MO 63005

Property at 2 Fairlake Dr, Chesterfield, MO 63005, 5 beds, 5.5 baths

$2,400,000

5 beds5.5 baths5,910 sq ft

2 Fairlake Dr, Chesterfield, MO 63005

Property at 2508 Peppermill Lake Ct, Wildwood, MO 63005, 5 beds, 3 baths

$710,000

5 beds3 baths4,000 sq ft

2508 Peppermill Lake Ct, Wildwood, MO 63005

Property at 511 Lalor Dr, Manchester, MO 63011, 5 beds, 3 baths

$475,000

5 beds3 baths3,524 sq ft

511 Lalor Dr, Manchester, MO 63011

Property at 218 Ella Rose Ln, Saint Charles, MO 63304, 5 beds, 3 baths

$1,379,000

5 beds3 baths3,640 sq ft

218 Ella Rose Ln, Saint Charles, MO 63304

Property at 5364 Tower Hill Ct, Weldon Spring, MO 63304, 5 beds, 5 baths

$1,295,000

5 beds5 baths4,848 sq ft

5364 Tower Hill Ct, Weldon Spring, MO 63304

Property at 3029 Rockwood Trl, Saint Charles, MO 63303, 5 beds, 2.5 baths

$675,000

5 beds2.5 baths3,207 sq ft

3029 Rockwood Trl, Saint Charles, MO 63303

Property at 12313 Tempo Dr, Saint Louis, MO 63146, 5 beds, 3 baths

$490,000

5 beds3 baths2,801 sq ft

12313 Tempo Dr, Saint Louis, MO 63146

Property at 5872 Wellington Farm Dr, Saint Charles, MO 63304, 5 beds, 3.5 baths

$399,900

5 beds3.5 baths3,038 sq ft

5872 Wellington Farm Dr, Saint Charles, MO 63304

Property at 12543 Merrick Dr, Saint Louis, MO 63146, 5 beds, 2 baths

$364,900

5 beds2 baths2,105 sq ft

12543 Merrick Dr, Saint Louis, MO 63146

Based on information submitted to the MLS GRID as of Fri Oct 23 2026. All data is obtained from various sources and may not have been verified by broker or 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.

5 Bedroom Homes for Sale in Chesterfield

There are currently 12 5 bedroom homes in Chesterfield. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chesterfield stay on the market for 42 days and receive 1 offers. Popular neighborhoods include Village Green, and Fairmount. This map is refreshed with the newest listings in Chesterfield every 15 minutes.

In the past month, 66 homes have been sold in Chesterfield. In addition to houses in Chesterfield, there were also 44 condos, 14 townhouses, and 0 multi-family units for sale in Chesterfield last month. Chesterfield is a not walkable city in St. Louis County with a Walk Score of 19. Chesterfield is home to approximately 47,130 people and 43,775 jobs. Find your dream home in Chesterfield using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chesterfield are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chesterfield. Our Chesterfield real estate stats and trends will give you more information about home buying and selling trends in Chesterfield. If you're looking to sell your home in the Chesterfield area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chesterfield with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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