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

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ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
Rarely available, TRUE 5-bedroom home in the highly sought-after Lake on White Road subdivision, offering over 3,000 square feet of comfortable living space. Enjoy the peaceful, low-traffic setting of of this neighborhood, ideally located adjacent to the vibrant Green Trails community. A spacious foyer welcomes you into the formal living and dining rooms, while the open floor plan seamlessly connects the updated eat-in kitchen, featuring granite countertops, stainless steel appliances, a gas range, and abundant cabinetry, to the inviting family room with a cozy gas fireplace. Convenient main-floor laundry adds to the home's functionality. Upstairs, zoned HVAC provides year-round comfort, an

$625,000

5 beds3 baths3,168 sq ft

14261 Finger Lake Dr, Chesterfield, MO 63017

5 bedroom home • Granite countertops • Gas range

OPEN FRI, 5PM TO 7PM

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
Welcome to 2315 Wellington Estates Drive, an impressive two-story residence situated in the desirable Wellington Estates neighborhood of Chesterfield. Offering over 5,400 square feet of living space, five bedrooms, four full bathrooms, and one half bathroom, this stately brick home combines timeless architectural character, generous living spaces, and exceptional versatility. Set on a level lot, the property features an inviting exterior, a three-car garage, and a thoughtfully designed floor plan ideal for both everyday living and entertaining. A grand two-story entry foyer makes an immediate impression, showcasing a sweeping staircase, soaring ceilings, intricate millwork, and elegant arch

$775,000

5 beds5 baths5,446 sq ft

2315 Wellington Estates Dr, Chesterfield, MO 63017

Two story residence • Three car garage • Level lot

3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
Absolutely fabulous 1.5-story home in the sought-after Green Trails Estates community, located in the award-winning Parkway Central School District. Offering 5+ bedrooms, 4.5 baths, and a versatile, light-filled floor plan, this spacious home sits on a beautiful . 28-acre lot with a private, lush backyard. The welcoming center-hall layout features hardwood floors throughout, a formal dining room, a living room ideal for a home office, and a stunning family room with custom built-ins, a gas fireplace, and views of the backyard. The updated eat-in kitchen showcases custom cabinetry, granite countertops, and stainless steel appliances, complemented by a breakfast room and breakfast bar. A stan

$685,000

5 beds4.5 baths4,834 sq ft

14258 Dinsmoor Dr, Chesterfield, MO 63017

Formal dining room • Gas fireplace • Custom built-ins

VIDEO TOUR

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
Stunning Fully Remodeled 5-Bedroom Home in the Heart of Chesterfield! An incredible opportunity to make this gorgeous, completely remodeled 5-bedroom, 3.5-bath home in the heart of Chesterfield yours! Beautifully updated from top to bottom, this home combines modern finishes, spacious living areas, and thoughtful design throughout. Step inside to a grand two-story entry foyer, flanked by a formal living room on one side and an elegant dining room on the other. The spacious family room features a cozy fireplace and opens seamlessly to the impressive chef’s kitchen, creating the perfect setting for entertaining and everyday living. The stunning kitchen boasts a large center island, cus

$825,000

5 beds3.5 baths3,454 sq ft

1823 York Ridge Ct, Chesterfield, MO 63017

Custom cabinetry • Fully remodeled • Large center island

OPEN SAT, 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

$570,000

5 beds3.5 baths3,897 sq ft

216 Trailtop Ct, Chesterfield, MO 63017

Insulated garage • Remodeled kitchen • Two primary suites

Property at 14901 Jockey Club Dr, Chesterfield, MO 63017, 5 beds, 3 baths

$715,000

5 beds3 baths4,960 sq ft

14901 Jockey Club Dr, Chesterfield, MO 63017

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 56 Chesterfield Lakes Rd, Chesterfield, MO 63005, 5 beds, 4 baths

$1,210,000

5 beds4 baths5,000 sq ft

56 Chesterfield Lakes Rd, Chesterfield, MO 63005

Property at 17915 White Robin Ct, Chesterfield, MO 63005, 5 beds, 4.5 baths

$1,299,000

5 beds4.5 baths5,118 sq ft

17915 White Robin Ct, Chesterfield, MO 63005

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

$1,949,000

5 beds4.5 baths4,528 sq ft

1224 Patchwork Flds, Chesterfield, MO 63005

Property at 1120 Cabinview Ct, Chesterfield, MO 63017, 5 beds, 2.5 baths

$824,900

5 beds2.5 baths4,476 sq ft

1120 Cabinview Ct, Chesterfield, MO 63017

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OPEN TODAY, 4PM TO 6PMFLOOR PLAN

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
Welcome home to 145 Shortleaf Pine! Nestled on a huge corner lot in the highly sought after Estates at Timberleaf neighborhood, this property is sure to impress. Upon entering, you are greeted by a generous foyer, office space to the left and formal dining to the right. The great room impresses with stone fireplace and natural light for days. The sightline extends into a chef's dream kitchen that speaks for itself. The island is enormous and storage is ample. A mudroom and laundry room extend the space en route to a 3 car, side-entry garage. The remainder of the main level includes a primary suite that is sure to provide more than enough space. The second floor includes 4 spacious bedroom a

$825,000

5 beds3.5 baths3,806 sq ft

145 Shortleaf Pine Dr, Saint Charles, MO 63304

Enormous island • Chef's dream kitchen • Huge corner lot

NEW 17 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
* * Exceptional 1.5-Story Residence with Main-Floor Primary Suite & 7+ Car Garage Potential! * * Meticulously maintained and thoughtfully improved, this exceptional home is situated at the end of a cul-de-sac on a beautifully landscaped lot with an expansive backyard. A dramatic two-story entry welcomes you into spacious, beautifully appointed living areas with hardwood floors and a luxurious main-floor primary suite. The private retreat features a sitting room with fireplace, two walk-in closets, a private balcony, and a stunning renovated bath with freestanding soaking tub, separate shower, automated blinds, and private water closet with premium electronic bidet toilet. The eat-

$1,999,000

5 beds4 baths5,915 sq ft

423 Conway Aire Dr, Saint Louis, MO 63141

Private balcony • Renovated bath • Expansive backyard

NEW 21 HRS AGO

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
Gorgeous rear tree lined lot in the very desirable Williamsburg neighborhood. The entry foyer opens up to large living area with separate dining and study. Gourmet center isle kitchen with large breakfast area and solid surface counters, walk in pantry, wolf appliances, sub zero refrigerator. The main floor master bedroom suite is privately located in the rear of the home. The master bath has large walk in tiled shower, soaking tub, two separate vanities, and two large walk in closets. Laundry is available on both 1st and 2nd floors. The main floor has high ceilings and beautiful moldings thru out. Upstairs there are 4 additional bedrooms, two full baths, bonus room and laundry. The finishe

$2,949,000

5 beds4.5 baths5,586 sq ft

26 Williamsburg Rd, Saint Louis, MO 63141

Rear tree lined lot • Wolf appliances • Walk in pantry

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
This Stunning 4+ beds & 3.5 bath ranch with over 5,000SF of luxury living space is exactly what you've been waiting for! The vaulted great room w/ updated gas fireplace, a wall of windows overlooking the private backyard and opens to the kitchen with bonus room beyond. The wide plank hardwood floors flow throughout the entire main floor. Breathtaking gourmet kitchen features 42"custom cabinetry, Wolfe gas range, custom hood vent, stone counters, stainless appliances, gorgeous custom island, beverage station, custom stone slab backsplash all new in the last 2 years! The kitchen opens to the den, breakfast area and walks out to the new incredible vaulted covered deck with outdoor k

$1,249,500

5 beds3.5 baths5,082 sq ft

17606 Lasiandra Dr, Wildwood, MO 63005

Custom cabinetry • Wolfe gas range • Vaulted great room

COMING SOON

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
Enjoy the neighborhood's multiple lakes, scenic walking trails, and convenient additional parking for guests. Further property details, including interior photography, disclosures, and a feature sheet, are anticipated early next week. Please check back for updates!

$1,400,000

5 beds4.5 baths6,394 sq ft

2642 Wynncrest Falls Dr, Wildwood, MO 63005

Multiple lakes • 0.63 acre lot • 3 garage spots

COMING SOON

ABOUT THIS HOME
5 Bedroom Homes for Sale in Chesterfield, MO
A masterful renovation has transformed this atrium ranch into a showcase of luxury and style for the way you live and entertain with sophisticated interiors with exceptional outdoor living. Rich hardwood flooring flows throughout the main level, highlighted by vaulted ceilings, designer finishes, and an open-concept layout ideal for both everyday living and hosting guests. The chef's kitchen is appointed with quartz countertops, a built-in column refrigerator, five-burner gas cooktop, double ovens, and a built-in microwave drawer. The adjoining great room showcases a gas fireplace, formal dining room, and a seamless flow to the outdoor living spaces. Step outside to your own private retreat

$1,300,000

5 beds3.5 baths5,216 sq ft

724 Forest Gate Ct, Wildwood, MO 63011

Masterful renovation • Custom wet bar • Private balcony

Property at 13214 Pinetree Lake Dr, Chesterfield, MO 63017, 5 beds, 3.5 baths

$799,000

5 beds3.5 baths4,788 sq ft

13214 Pinetree Lake Dr, Chesterfield, MO 63017

Property at 12372 S 40 Dr, Saint Louis, MO 63141, 5 beds, 3.5 baths

$995,000

5 beds3.5 baths3,896 sq ft

12372 S 40 Dr, Saint Louis, MO 63141

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 4 Williamsburg Rd, Saint Louis, MO 63141, 5 beds, 4.5 baths

$3,495,000

5 beds4.5 baths6,825 sq ft

4 Williamsburg Rd, Saint Louis, MO 63141

Property at 75 Garden Ln, Maryland Heights, MO 63043, 5 beds, 2 baths

$350,000

5 beds2 baths2,024 sq ft

75 Garden Ln, Maryland Heights, MO 63043

Property at 715 Madison Vly, Wildwood, MO 63005, 5 beds, 4.5 baths

$1,350,000

5 beds4.5 baths4,870 sq ft

715 Madison Vly, Wildwood, MO 63005

Property at 1824 Topping Rd, Saint Louis, MO 63131, 5 beds, 4.5 baths

$2,495,000

5 beds4.5 baths7,174 sq ft

1824 Topping Rd, Saint Louis, MO 63131

Property at 25 Leaside Ct, Manchester, MO 63011, 5 beds, 3 baths

$519,900

5 beds3 baths3,178 sq ft

25 Leaside Ct, Manchester, MO 63011

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

$400,000

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

$1,489,966

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

$2,295,000

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

Based on information submitted to the MLS GRID as of Thu Nov 05 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 14 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 40 days and receive 1 offers. Popular neighborhoods include Village Green, Fairmount, Wildwood, and Woods Mill. This map is refreshed with the newest listings in Chesterfield every 15 minutes.

In the past month, 50 homes have been sold in Chesterfield. In addition to houses in Chesterfield, there were also 43 condos, 18 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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