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!
Subdivision: Landings At Lake Chesterfield One
List Price: $525,000
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
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
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
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 Add
List Price: $559,000
Welcome to your own private retreat within the highly sought after Lake Chesterfield neighborhood in Wildwood. Perfectly positioned on a quiet cul-de-sac, this beautifully updated 4 bed, 3.5 bath, 2-story home offers over 3,300 square feet of thoughtfully designed living space, including a finished lower level, and combines everyday comfort with exceptional outdoor living. The backyard is truly the star of the show, featuring a custom 19,500-gallon gunite heated saltwater private inground pool with a stunning water fountain feature, expansive pool deck, outdoor kitchen, and fire pit—creating the ultimate setting for summer gatherings, weekend celebrations, or peaceful evenings under the stars. Inside, the beautifully appointed kitchen serves as the heart of the home, featuring granite countertops, a center island, stainless steel appliances, and a dry bar area where conversations naturally unfold. Gather around the cozy wood-burning fireplace on chilly evenings, host holiday dinners in the elegant formal dining room, or enjoy quiet conversations in the formal living room. A convenient main-floor laundry room adds ease to busy daily routines. Upstairs four spacious bedrooms provide comfortable retreats, while recent updates (2026)—including a stunning primary bath and additional remodeled full bath. Newly remodeled finished basement offers large rec room, additional sleeping area and new full bathroom. Additional improvements include fresh paint and new blinds throughout (2026) a new HVAC system; new pool chlorinator (2023), and luxury vinyl plank flooring across the main level (2022). Located in the award-winning Rockwood School District, this exceptional community offers three pools, fishing ponds, walking trails, a clubhouse, pickleball and tennis courts, basketball courts, and an active swim team. More than a home, this is a place where lifelong memories are waiting to be made.
Subdivision: Cove At Lake Chesterfield The
List Price: $445,000
Welcome to 16475 Cove Landing Ct. There's so much to love about this home’s cul-de-sac location in the sought-after Lake Chesterfield community. Residents of this popular neighborhood enjoy community clubhouse, multiple pools, tennis & pickle ball courts, sports court, walking trails and private lakes. Upon entering the home you will immediately notice the vaulted ceilings, open floor plan and so much natural light. This one owner ranch style home has been meticulously cared for and updated, and pride of ownership is evident. Front entry, living and dining rooms are the first areas that greet you. The expansive, updated kitchen opens to the notably large family room, which the owners had the builder expand when the home was built. This makes for such great living space and leads to the backyard and patio. The split bedroom floor plan provides a private primary bedroom suite with spacious bath and walk-in closet. Two additional bedrooms and full bath complete the main level. The finished lower level provides even more living space, with a substantial rec room, office, full bath, awesome walk-in closet, workshop area and so much storage. Fantastic location in the Rockwood School district, close to so many amenities!
Subdivision: The Cove At Lake Chesterfield
List Price: $425,000
Welcome to this beautiful 3 bedroom, 2 full bath ranch home in the Highly rated Rockwood school district in the sought after Lake Chesterfield subdivision. An updated Kitchen is the heart of the home with granite counter tops, custom cabinetry, stainless steel appliances, breakfast bar peninsula and breakfast room. Open floor plan, vaulted ceiling with skylights in the living room, dining room combo and wood flooring. Relax in the spacious primary bedroom suite with vaulted ceiling, updated primary full bath and walk-in closet. Second bedroom with adjacent additional updated full bath on the main level. Main floor laundry brings convenience and ease. The nicely finished lower level with additional bedroom, family room, office, storage room and walkout. Sip your morning coffee or unwind in evening star gazing on the deck off the main floor living area or on the lower level backyard patio. Enjoy the vast neighborhood amenities, 3 outdoor pools overlooking the stunning tree lined lake which allows non-motorized boats and is surrounded by a paved walking trail. Other features include clubhouse, fitness room, tennis courts, pickleball courts, basketball court, summer swim team and fishing ponds. Close proximity to shopping, restaurants, Rockwood reservations and the miles of trails in Wildwood.
Subdivision: Harbors At Lake Chesterfield One
List Price: $585,000
Welcome to this beautifully updated 2-story former display home, ideally situated on a quiet cul-de-sac within the award-winning Rockwood School District. With thoughtful updates throughout, this home offers a perfect blend of style, space, and everyday functionality. This spacious home features 4 bedrooms, 3.5 baths, and an additional sleeping room in the walkout basement, providing flexibility for guests, work-from-home needs, or additional living space. The main level showcases luxury vinyl plank flooring, a sunken living room filled with natural light, and a warm, inviting family room complete with a wood burning brick fireplace and wet bar—ideal for both relaxing and entertaining. The kitchen is a true standout, beautifully redesigned with quartz countertops, a large island with seating, high-end gas cooktop, and premium Thermador double wall ovens. It opens seamlessly to the breakfast room and hearth room, creating a natural gathering space enhanced by abundant light. A private dining room with French doors offers the perfect setting for more formal occasions, while main floor laundry adds everyday convenience. Upstairs, all bedrooms have been updated with fresh finishes and new carpet. The primary suite offers a true retreat with vaulted ceilings, double door entry, and a spacious en suite featuring a modern dual-faucet sink design, soaking tub, separate shower, linen storage, and multiple walk-in closets. One secondary bedroom is currently configured as a dedicated laundry space with sink, offering flexibility and easy conversion back to a bedroom if desired. The walkout lower level expands your living space with a large rec room, kitchenette, sleeping area, and a walk in climate-controlled wine cellar with an added humidor—perfect for entertaining or unwinding. Step outside to enjoy a beautifully landscaped lot with mature trees, an aggregate patio and walkway, and a charming pond feature that brings a soothing and unexpected element to the outdoor space. The expansive deck with dual access points creates an ideal setting for gatherings or quiet evenings. The 3-car garage provides ample storage and functionality. Located in the Harbors at Lake Chesterfield, residents enjoy access to a neighborhood pool, clubhouse, walking trails, multiple lakes, and many other perks. This established community remains a top choice for buyers seeking amenities, setting, and long-term value.
Subdivision: Harbors At Lake Chesterfield One
List Price: $465,000
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
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