Welcome to the Lake Chesterfield Subdivision page on WildwoodRealEstateSearch.com. Discover the serene lifestyle offered by this beautiful Wildwood, MO community, featuring a variety of stunning homes. With agent information conveniently located in the right sidebar, you can easily request more details or schedule a viewing, whether in person or virtually. Simply call or click to get in touch with our expert agents. Begin your journey to finding the perfect home in the Lake Chesterfield Subdivision today and experience lakeside living at its finest!

Total Results: 10
Total: 10

Subdivision: The Harbors at Lake Chesterfield

List Price: $539,900

Pending 5 bds 4 ba 2,886 sqft 2 Story MLS# 26050122 2 DOM

Welcome home to this spacious 5-bedroom, 3.5-bath home offering over 4,000 square feet of living space in the highly sought-after Harbors at Lake Chesterfield subdivision. Nestled on a private, park-like lot, this home truly must be seen to be appreciated. Designed for both everyday living and entertaining, the open, bright floor plan features a stunning two-story foyer with stylish barn doors leading into the living room, which flows seamlessly into the expansive family room with a cozy fireplace. Recessed lighting is found throughout the home, while the convenient split staircase provides easy access between levels.The kitchen is beautifully appointed with stainless steel appliances, granite countertops, a stone sink, and a walk-in pantry. A generous mudroom includes the main-floor laundry for added convenience. Step outside to enjoy the newer pure pine deck and patio, just two years old, creating the perfect setting for outdoor gatherings and backyard parties.The primary suite offers elegant coved and vaulted ceilings in both the bedroom and bath, creating a spacious and relaxing retreat. The finished walk-out lower level provides incredible flexibility with a fifth bedroom, full bath, family room, office or gaming area, and plenty of space for entertaining or accommodating out-of-town guests. Located in a premier community with a clubhouse, lake, tennis courts, and swimming pool, you’ll love the unbeatable location and outstanding neighborhood amenities. Spacious, private, and impeccably maintained—this is a home you won’t want to miss!

Subdivision: Harbors At Lake Chesterfield Add

List Price: $495,000

Pending 4 bds 3 ba 2,841 sqft 1.5 Story MLS# 26040886 2 DOM

From the soaring ceilings to the beautifully updated spaces, this stunning story-and-a-half is designed to impress. The spacious floor plan offers 4 bedrooms, 2.5 baths, and a sought-after main-floor primary suite. The heart of the home is the impressive kitchen, complete with granite countertops, stainless steel appliances, double ovens, gas cooktop, custom cabinetry, and a center island overlooking the vaulted great room. Elegant formal dining, hardwood flooring, and abundant natural light add warmth and character throughout. Upstairs offers a full bathroom and three generously sized bedrooms, while the private backyard provides a peaceful setting surrounded by mature trees. Combining space, style, and an unbeatable Wildwood location, this home is one you won't want to miss. As an added bonus, the roof was replaced in 2023, gutters and facia replaced in 2024, garage door in 2024, water heater in 2025 and the exterior was repainted in 2023.

Subdivision: Estates At Lake Chesterfield The

List Price: $495,000

Pending 4 bds 3 ba 2,468 sqft 2 Story MLS# 26048115 3 DOM

Welcome Home! Gorgeous two-story home in a highly desirable neighborhood in Wildwood. This well-maintained property offers a fenced backyard with an inviting patio with a stunning stone fireplace that is perfect for entertaining, along with stunning updated hardwood floors throughout the first level and beautifully updated bathrooms. The spacious primary suite features vaulted ceilings, and the updated kitchen provides a fresh, modern feel for everyday living and hosting. Three car garage and plenty of room for everyone. Enjoy access to exceptional community amenities including a pool, tennis court, pickleball, and clubhouse, all in a location served by great schools in the highly convented Rockwood School district.

Subdivision: Estates At Lake Chesterfield The

List Price: $524,850

Reduced $20,150 (was $545,000)
Active 4 bds 3 ba 2,132 sqft 2 Story MLS# 26047890 13 DOM

New Price: $524,850. Sunday Open House (08/09), 1-4 p.m. Welcome to this attractive 2-story home, located on a cul-de-sac, with 4 bedrooms, 2.5 bathrooms and partially completed lower level. Lots of natural light. Spacious backyard with large deck (22x19) ideal for gatherings or quiet evenings. Roof (03/2026), siding (02/2026). The 2-story foyer opens to the dining room with gleaming hardwood floor and built-ins. The family room features a wood-burning fireplace, built-in shelves, gleaming hardwood floor, bay window and ceiling fan. Opens to the spacious kitchen and breakfast area with custom cabinetry, gas stove, island/breakfast bar, built-in microwave, pantry and planning desk. Leads out to the deck. Main floor laundry room with countertop and cabinets. All 4 bedrooms on the second floor with 2 full bathrooms. The primary bedroom has a vaulted ceiling, walk-in closet and luxurious bathroom with double bowl vanity, tub and separate shower. The partially finished lower level offers a game area with pool table, entertaining space with built-in countertop/ cabinets and storage room. Attached 2-car garage. The deck will be stained prior to closing. Neighborhood amenities include: Clubhouse, pool, tennis/pickleball courts, lake, walking trails. Access to miles of beautiful Wildwood hiking/biking trails. Convenient to shops/restaurants. Minutes to Wildwood Towne Center. Rockwood school district.

Subdivision: Landings At Lake Chesterfield One

List Price: $525,000

Pending 4 bds 3 ba 3,111 sqft 2 Story MLS# 26043225 5 DOM

Enjoy exceptional space, beautiful updates, and an incredible backyard setting in this meticulously maintained two-story home located in the sought-after Landings at Lake Chesterfield. From the dramatic two-story entry and expansive main living areas to the spectacular composite deck overlooking the private backyard, every space has been thoughtfully designed for comfortable everyday living and effortless entertaining. An impressive two-story foyer with gleaming hardwood floors, soaring ceilings, and an open staircase creates a memorable first impression. The thoughtfully designed main level balances elegance and functionality with a formal dining room featuring a coffered ceiling and decorative wainscoting, as well as a private home office tucked behind French doors. The expansive family room is the heart of the home, where rich hardwood flooring, a stunning floor-to-ceiling brick wood-burning fireplace, and walls of windows frame peaceful, tree-lined views while filling the space with natural light. Flowing seamlessly into the adjoining breakfast room and kitchen, the open floor plan is ideal for gathering with family and friends. The spacious kitchen offers abundant custom cabinetry, expansive countertops, a custom tile backsplash, stainless steel appliances, a gas oven, walk-in pantry, planning desk, and an oversized center island with generous prep space and seating. Just beyond, the light-filled breakfast room is surrounded by windows and opens through a newer sliding glass door to the expansive composite deck, creating a seamless transition between indoor and outdoor living while showcasing beautiful views of the private backyard. Upstairs, the generously sized primary suite offers a peaceful retreat with a coffered ceiling, large walk-in closet, and an ensuite bath featuring dual vanities, a soaking tub, separate shower, and updated luxury flooring. Three additional bedrooms, each with generous closet space, share a spacious hall bath. The walk-out lower level offers endless possibilities for future expansion and already includes a bathroom rough-in, providing an exceptional opportunity to create additional living space tailored to your needs. Outdoor living is truly a highlight of this home. The composite deck, thoughtfully designed with both covered and open-air spaces, overlooks a beautifully landscaped, level backyard surrounded by mature trees for added privacy. Lush green space, established gardens, a fire pit, and plenty of room to relax, entertain, or play create an outdoor setting that’s as inviting as the home itself. Additional updates include a new roof (2024), composite deck (2020), A three-car garage, and main-floor laundry. Residents of The Landings at Lake Chesterfield enjoy exceptional neighborhood amenities, including a community pool, and playground. Conveniently located in the highly regarded Rockwood School District and just minutes from popular shopping, dining, parks, and major highways, this is a home you do not want to miss!

Subdivision: Harbors At Lake Chesterfield One

List Price: $499,900

Pending 4 bds 2 ba 1,797 sqft 1 Story MLS# 26041057 2 DOM

Welcome to 11 Windjammer Court, a beautifully maintained 4-bedroom, 2-bath ranch offering 1,797 square feet of comfortable living space in the heart of Wildwood. Nestled on a quiet cul-de-sac, this move-in ready home features a large, level backyard and access to outstanding neighborhood amenities, including pools, lakeside clubhouse, fishing, and pickleball courts. Major mechanical and exterior improvements have already been completed, allowing the next owner to simply move in and enjoy. Recent updates include a new roof, new siding, oversized 6-inch gutters, new HVAC system, updated kitchen, renovated hall bathroom, new front door, 75-gallon water heater, and updated windows and sliding glass door. Inside, you’ll find a bright, open floor plan with a soaring cathedral ceiling and a cozy fireplace in the great room. The updated kitchen features quartz countertops, stainless steel appliances, luxury vinyl plank flooring, and plenty of workspace for cooking and entertaining. The spacious primary suite includes a walk-in closet, and the convenient main-floor laundry makes everyday living easy. The unfinished lower level provides abundant storage and offers endless possibilities for future living space, whether you envision a family room, home gym, workshop, or recreation area. Step outside to the patio overlooking the spacious, level backyard—perfect for summer barbecues, entertaining friends, gardening, or simply relaxing. Located in the award-winning Rockwood School District and just minutes from bike paths, parks, shopping, dining, and major highways, this exceptional home offers the perfect combination of thoughtful updates, desirable amenities, and an unbeatable location. Move in and enjoy with confidence—the major updates have already been completed!

Subdivision: Harbors At Lake Chesterfield Add

List Price: $489,900

Reduced $20,000 (was $509,900)
Active Under Contract 4 bds 3 ba 1,753 sqft 1.5 Story MLS# 26038593 54 DOM

Thinking about relocating to Lake Chesterfield? Desirable one and a half story with a great floor plan offering a big kitchen and dining area, a welcoming family room, and a spacious primary main floor bedroom. Lots of special features including vaulted ceilings, a beautiful coffered ceiling in the formal dining room, six panel doors, and lots of the natural lighting. There are three nice sized bedrooms on the second level with a full bath. Plenty to do, enjoy access to lakes, pools, clubhouse, sport courts, and walking trails. Home has some updating needs but seems sound. HVAC has been updated within the last 5-7 years. Fence rear yard and backs to trees offering privacy. Bring your offer today.

Subdivision: Estates At Lake Chesterfield The

List Price: $539,900

Reduced $10,000 (was $549,900)
Pending 4 bds 3 ba 2,650 sqft 2 Story MLS# 26038621 24 DOM

THIS HOUSE IS GORGEOUS!! Corner lot, rear-entry 3 CAR GARAGE and perfect curb appeal! Enter this UPDATED BRIGHT OPEN floor plan to find: 2 sty foyer; separate dining & living room; family room w/gas fireplace, bay window; spacious kitchen w/ breakfast bar, custom cabinetry, granite countertops, stainless steel appliances w/induction stove and double oven, center island, additional countertop space, garden window, pantry, recessed lighting and eat-in area; half bath and laundry room w/utility sink, all on the main level. Upper level includes; primary bedroom suite - large bdroom w/vaulted ceiling, walk-in closet - full bath w/ceramic tile floor, tub/sep shower, linen closet, double vanity; 3 additional bedrooms w/overhead lighting; full bath w/dbl vanity. Beautiful flat fenced backyard w/deck. Additional updates include: wood flooring thruout main flr, 6 panel doors, newer baseboards, newer roof, hvac systems, water heater, professional landscaping + outdoor lighting, sprinkler and security systems, newer light fixtures and hardware throughout, exterior shutters and newer fence. Awesome 3 car garage updates include: new side-opening garage door openers, garage door tracks relocated vertically for additional clearance, new storage shelving, fully refinished drywall, ceiling, baseboards and paint. Neighborhood amenities include clubhouse, pools, tennis and basketball courts, lake, walking trail and excercise area. Rockwood Schools.

Subdivision: Harbors At Lake Chesterfield One

List Price: $465,000

Pending 3 bds 3 ba 2,222 sqft 2 Story MLS# 26031415 5 DOM

Welcome to 164 Crestmont Circle, a beautifully refreshed and loved two story home tucked into the heart of Lake Chesterfield. From the moment you step inside, the bright, freshly painted interior and gorgeous, light filled foyer create an immediate sense of warmth and welcome. Sunlight pours through the home, enhancing its effortless flow and making every room feel open, airy, and inviting. Designed for both comfort and connection, this 3 bedroom, 3 bath home offers easy living and gracious entertaining. The main level features a natural gathering space perfect for hosting family and friends, celebrating milestones, or enjoying cozy evenings at home by the wood burning fireplace. The kitchen and breakfast area open directly to the large, fully fenced, level backyard that is an ideal setting for fur babies, play, gardening, or weekend barbecues. It’s truly an outdoor extension of your living space. Upstairs, three spacious bedrooms provide room to unwind, including a peaceful primary suite with its own private bath featuring a soaking tub and separate shower. The finished lower level expands your options even further with a generous recreation area and a dedicated office which is perfect for working from home, relaxing, or creating a media or hobby space tailored to your lifestyle. The amenities in Wildwood make everyday living effortless, just minutes from shopping, dining, parks, and top rated Rockwood schools. As a resident of Lake Chesterfield, you’ll enjoy lakes, pools, a clubhouse, sport courts, and walking trails; this is an unbeatable lifestyle in a truly exceptional neighborhood. Warm, bright, and beautifully cared for, this home is ready to welcome you.

Subdivision: Estates At Lake Chesterfield The

List Price: $470,000

Reduced $15,000 (was $485,000)
Active 4 bds 3 ba 2,507 sqft 2 Story MLS# 26034346 64 DOM

Experience 16201 Surfview Ct, a residence refreshed with fresh interior paint and partial flooring replacement throughout. The living area includes a fireplace, stainless steel, complemented by a functional kitchen island for convenience. The primary bathroom provides practicality with double sinks and a separate tub and shower setup. An accessible patio with fenced in backyard. This residence blends recent updates with functional comfort—ready for you to enjoy. Included 100-Day Home Warranty with buyer activation

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