Chesterfield Real Estate Search

Chesterfield Homes with a Pool for Sale

Our website features the best real estate search for homes with a pool properties available in Chesterfield and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in the Chesterfield real estate market? Sign up for a Chesterfield Real Estate Market Report to see what’s active, under contract, and sold!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Chesterfield Homes with a Pool for Sale

ACTIVE UNDER CONTRACT Status ⋅ Bruce Butler

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

ACTIVE Status ⋅ Marie Kutryb

This stunning story-and-a-half home offers 6 bedrooms, 4.5 baths, and more than 5,500 square feet of beautifully designed living space. Situated on a private lot with a secluded backyard, the property features a sparkling saltwater pool, abundant natural light, and thoughtful updates throughout. The main level showcases a dreamy kitchen including Custom cabinetry, solid surface countertops, walk-in pantry and stainless steel appliances. A luxurious primary suite complete with a spa-inspired bathroom and two spacious walk-in closets. The inviting great room features a gas fireplace and large windows that fill the home with natural light. rounds out the main floor. Upstairs, you'll find a massive loft area along with four generously sized bedrooms, including one bedroom with a private ensuite bath and two bedrooms connected by a Jack-and-Jill bathroom. The finished walk-out lower level is ideal for entertaining, offering a built-in bar, a sixth bedroom, and a full bath, providing excellent space for guests or multigenerational living. Recent Updates Include: Roof (2025) Siding (2026) New pool equipment (2023) Vent hood (2026) Garage doors (2021) Deck flooring, stairs, and railing (2026) With spacious living areas, extensive updates, and resort-style outdoor amenities, this home offers the perfect blend of luxury, comfort, and functionality.

220 Woodcliffe Place Dr, Chesterfield

ACTIVE Status ⋅ DJ Gudipati

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

ACTIVE UNDER CONTRACT Status ⋅ Loreli Escalante

Tucked away on 3 private acres in the heart of Chesterfield, this extraordinary estate offers a lifestyle that is becoming increasingly difficult to find. Surrounded by mature trees and overlooking a private lake, the setting feels peaceful, secluded, and worlds away from the everyday. Designed to bring the outdoors in, the home showcases soaring ceilings, dramatic walls of glass, exposed beams, and breathtaking views from nearly every room. The spacious floor plan offers over 4,600 square feet of living space with 4 bedrooms, 5 full baths, and 2 half baths, providing plenty of room for both everyday living and entertaining. The expansive primary suite is a true retreat featuring a luxurious bath, fireplace, and oversized walk in closet. Step outside and discover what makes this property truly special. Multiple decks built with Ironwood lumber that overlook the water and surrounding woods, creating the perfect place for morning coffee, quiet evenings, or gathering with family and friends. Enjoy summers by the pool, evenings around the fire, and direct access to the private lake from your own dock. The home is Topped off with an Echo Star roof that includes a warranty for labor and materials for 50 years framed by Copper gutters. If the power goes out the 60kw generator will provide uninterrupted power until public power is restored. Additional buildings include a chicken coop and shed Homes like this are rarely available. Offering timeless architecture, unmatched privacy, and a setting that simply cannot be replicated, this is more than a home. It is a retreat, a gathering place, and a chance to enjoy the beauty of nature without ever leaving Chesterfield.

4 Arrowhead Estates Ln, Chesterfield

ACTIVE Status ⋅ Megan Rowe

Back on market NO fault of Seller! Buyer plans changed. This exceptional villa in the gated Conway Meadows community offers the perfect blend of comfort, style, and easy living. Featuring 4 bedrooms and 3 full baths (TWO beds and 2 FULL baths on the main level), the home showcases an inviting open layout designed for both everyday living and entertaining. Rich hardwood flooring flows throughout much of the main level, while vaulted ceilings and a gas fireplace create a warm and welcoming focal point in the family room. The updated kitchen is beautifully appointed with quartz countertops, custom cabinetry, a built-in wall oven and microwave, and a spacious breakfast room with plenty of natural light. Nearby dining and living spaces provide flexibility for gatherings both large and small. Retreat to the main-level primary suite featuring a walk-in closet and a renovated bath complete with double vanities and an oversized walk-in shower. A second bedroom, full bath, and main-floor laundry room add convenience and functionality to the main level. Upstairs, you will find two additional spacious bedrooms, another full bath, and a versatile loft with wet bar—ideal for guests, hobbies, or additional entertaining space. Outdoor living shines with a private in-ground saltwater pool and hot tub surrounded by peaceful landscaping, creating your own backyard escape. Additional highlights include a whole-house generator, newer roof, central vacuum system, and an unbeatable location close to shopping, restaurants, parks, and major highways.

14300 Open Meadow Ct, Chesterfield

ACTIVE Status ⋅ Stephanie Duffy

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

ACTIVE UNDER CONTRACT Status ⋅ Kristi Monschein Desantis

An extraordinary Frank Lloyd Wright-inspired 7,000 sq ft custom estate set on 3+ private, level acres in sought-after Pacland Place, where architecture and nature exist in perfect harmony. The outdoor living is nothing short of exceptional, featuring an in-ground pool with a tranquil waterfall, a covered patio, a fenced yard, and an additional side retreat complete with an outdoor fireplace, pergola, and hot tub—designed for both relaxation and unforgettable entertaining. A grand entry foyer welcomes you with a custom ceiling, bow window, and an impressive wine room, setting the tone for the home’s refined design. The massive great room showcases a stone-surround wood-burning fireplace, custom vaulted ceiling, walk-up wet bar, and French doors leading to the patio, seamlessly connecting to the formal vaulted dining room. Both spaces are highlighted by walls of custom windows that frame the surrounding landscape and fill the home with natural light. A private study with French doors and built-ins offers a quiet retreat. The spectacular kitchen is a true showpiece, appointed with solid surface countertops, extensive millwork, 42-inch cherry cabinetry, center island, double ovens, gas cooktop, dual sinks, access to the deck, and an adjoining breakfast room. The spacious primary suite is a sanctuary of its own, featuring a custom ceiling, a wall of windows, and a walk-in closet with French doors. The luxurious ensuite includes a steam shower, window seat, custom shower with dual shower heads, rough-in for a soaking tub, and double vanities. Two additional bedrooms and 1.5 baths complete the main level. The expansive walk-out lower level is an entertainer’s dream, offering a large family room with a wood-burning fireplace, a one-of-a-kind sunken walk-behind full wet bar, an office or potential bedroom, an additional bedroom, and two full baths. Additional highlights include two laundry areas (main and lower levels), a 3-car side-entry garage with a safe room, circular driveway, zoned HVAC, and countless custom details throughout. A truly remarkable residence that celebrates distinctive design, architectural character, and one-of-a-kind craftsmanship.

16916 Pacland Ridge Dr, Chesterfield

ACTIVE UNDER CONTRACT Status ⋅ Catherine Shaw-Connely

An EXQUISITE EQUESTRIAN ESTATE nestled in the woods amongst 14+/- scenic rolling acres in Chesterfield along Kehrs Mill Road! Idyllic & rare, this extraordinary estate features a sprawling, custom designed 4,125 sq ft, 7 bedroom, 3 full & 1 half bath, pool, pool house, barn, 1 paddock, 1 pasture, and workshop! 2 story home w/impressive architectural detail, original wood flooring & abundant windows allowing expansive views of the lavish acreage! Perfect location for your dream home, a contemporary farmhouse, or even a country estate. Within the Rockwood School District with easy access to Hwy 40/64, shopping, dining, and Chesterfield Valley amenities. ALL buildings are being sold "as is", NO Seller's Disclosure available. DUPLICATE LISTING OF MLS#25026775.

1577 Kehrs Mill Rd, Chesterfield

Start Your Search