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$599,400
4 Beds ⋅ 3 Baths ⋅ 26051546 MLS ⋅ ACTIVE Status
Welcome to 165 Saddleford Drive, where beautifully updated spaces and a thoughtfully opened floor plan create a home designed for both everyday living and entertaining. At the heart of the home is the renovated chef’s kitchen, featuring an oversized center island, updated cabinetry, new appliances, and plenty of room to gather. The kitchen flows seamlessly into the surrounding living and dining spaces, creating the open, connected feel everyone wants. Updated flooring runs throughout the home, complemented by abundant natural light, beautiful millwork, and replaced windows. All three bathrooms have been updated, including the private ensuite in the spacious primary. The finished lower level adds even more living space, including an additional room and half bath—perfect for a home office, playroom, craft room, workout space, or whatever fits your lifestyle. Outside, enjoy front porch living on a cul-du-sac while the backyard offers plenty of space to relax, play, or entertain. Located in the Parkway School District with convenient access to Chesterfield Valley shopping and dining, Faust Park, and I-64/US-40. Major improvements add even more value, including furnace and AC replaced in 2023, range in 2025, and a new roof and garage door in 2026. Beautifully updated, exceptionally functional, and ready for its next chapter!

165 Saddleford Dr, Chesterfield
$424,900
3 Beds ⋅ 3 Baths ⋅ 25005438 MLS ⋅ ACTIVE Status
Fabulous 2-story villa in a sought-after Chesterfield location! Step through the charming gated fence into a beautifully landscaped courtyard and spacious covered porch. Inside, stylish wood floors flow throughout most of the main level. Elegant living and dining rooms flank the welcoming foyer. The spacious chef’s kitchen features abundant cabinetry, stylish countertops, stainless steel appliances and tile flooring. A convenient main-floor laundry room offers additional cabinetry and an exterior door leading to the patio. The inviting family room features a fireplace and atrium doors (2024) opening to the spacious patio, while a stylishly updated powder room (2024) completes the main level. Upstairs, retreat to the luxurious primary suite featuring a generous sleeping area, adjoining sitting room with built-in bookshelves, beautifully remodeled bath (2024) and spacious walk-in closet. Two additional generously sized bedrooms, an updated hall bath (2024) and linen closet complete the second floor. The lower level offers excellent potential for future finished living space while providing plenty of storage. Outdoors, enjoy the peaceful brick patio surrounded by a wood privacy fence—an inviting spot to relax or entertain. Additional updates include architectural shingle roof (2024), AC (2020) furnace (2021), hot water heater (2021), garage door and opener (2026)

1578 Milbridge Dr, Chesterfield
$569,900
5 Beds ⋅ 3 Baths ⋅ 26051896 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome to 1 Oakland Hills Drive, updated 2-story home tucked into the sought-after Four Seasons community of Chesterfield. Offering 5 bedrooms, 3 full baths and just over 2,900 square feet of thoughtfully designed living space, this home perfectly blends classic charm with the updates and functionality today’s buyers are looking for. Step inside to beautiful hardwood flooring and an inviting foyer that opens to a spacious living room with a wonderful view of the Four Seasons Golf Course and subdivision pool. The main level also features a separate dining room conveniently located just off the kitchen, making entertaining a breeze. The updated kitchen offers custom cabinetry, quartz countertops, backsplash, under cabinet lighting, stainless steel appliances and breakfast bar seating, while the adjoining eat-in area flows seamlessly into the comfortable family room. The family room features an updated fireplace and an open layout that creates an inviting space for everyday living and gathering. A generous bonus room adds even more versatility and can easily accommodate a playroom, home office, hobby space or guest area, with convenient access to the backyard and deck. Upstairs, you’ll find a spacious primary suite with private bath, along with four additional bedrooms and another full bath, providing plenty of room for family and guests. The finished lower level offers additional recreation space currently being used as a play area and home gym. Outside, enjoy the expansive fenced backyard, spacious deck and beautiful golf-course views—an ideal setting for relaxing, entertaining or simply enjoying the peaceful surroundings. Additional highlights include a 3-car attached garage, full basement, community pool and clubhouse (extra $80/ year for membership), all in an incredible Chesterfield location within the Parkway School District. Recent interior updates include kitchen, fresh paint throughout, working fireplace-gas, new HVAC (both units), new water heater, switches & outlets, sliding door for deck entry, all completed between 2025 & 2026. Exterior updates include a new roof, siding, gutters and deck, all completed in 2022 as well as low maintenance landscaping in 2025. With its generous living spaces, flexible floor plan and fantastic location, check this gem out today!

1 Oakland Hills Dr, Chesterfield
$395,000
3 Beds ⋅ 3 Baths ⋅ 26052042 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome to this beautifully maintained 3-bedroom, 3-bath single family residence located in the heart of Chesterfield, offering convenient access to Highway 64/40, an abundance of restaurants, shopping, entertainment, and area amenities. From the moment you enter, you’ll appreciate the inviting open feel and abundance of natural light. The spacious kitchen features crisp white cabinetry, newer granite countertops and backsplash, stainless steel appliances, and a convenient eat-in kitchen, perfect for casual meals or morning coffee. The bright and cheerful living room is filled with sunshine from the generous windows and sliding glass door, creating a warm and welcoming space for relaxing or entertaining. The elegant formal dining room provides the perfect setting for special gatherings. Newer carpeting adorns the staircase and upstairs three comfortable bedrooms offer plenty of space. The spacious primary suite features a private ensuite and walk-in closet, while two additional bedrooms share a full hall bath which provides flexibility for family or guests. The partially finished lower level offers additional living space along with laundry area and storage with built in shelving. Step outside to enjoy your own private, fenced-in patio, an ideal spot for morning coffee, evening relaxation, or outdoor entertaining. Updates include newer granite counter tops and backsplash, newer roof, soffits and gutters, newer hardwood flooring throughout, newer HVAC and new garage door opener and garage concrete pad! With its desirable Chesterfield location, thoughtful floor plan, abundant natural light, and generous living space, this condo offers the perfect combination of comfort, convenience, and low-maintenance living. Come see all this wonderful home has to offer!

16463 Cobbleskille Dr, Chesterfield
$649,900
4 Beds ⋅ 3 Baths ⋅ 26043195 MLS ⋅ ACTIVE Status
Welcome to a truly exceptional Chesterfield residence where timeless elegance meets modern comfort. Perfectly positioned on a beautifully landscaped Corner lot, this impressive home offers the space, style, and functionality today's buyers are searching for. From the moment you step into the welcoming foyer, you'll appreciate the generous living spaces, exceptional layout, and quality improvements throughout. Extensively updated, this impressive 4-bedroom, 3-bath home features a remodeled kitchen, beautifully renovated bathrooms, updated flooring, fresh paint, and an HVAC system replaced in 2022, offering peace of mind and move-in-ready convenience. Designed with entertaining in mind, the expansive floor plan offers multiple gathering spaces to suit every occasion. The oversized family room is a true centerpiece, featuring a cozy fireplace, abundant storage, and direct access to a private side patio. A charming hearth room shares the fireplace, creating an inviting atmosphere for relaxing evenings. The formal living room showcases beautiful wood flooring and flows seamlessly into the elegant dining room, complete with custom built-in cabinetry for added style and functionality. The spacious kitchen is a dream for home chefs, offering abundant counter space, two pantries, and easy access to the backyard through a sliding glass door. Step outside to your own private retreat featuring a fully fenced yard, expansive patio, mature landscaping, including custom landscape lighting that creates a stunning evening ambiance. Upstairs, you'll find the Primary suite and three generously sized secondary bedrooms along with a luxurious primary suite featuring a walk-in closet and a beautifully renovated spa-inspired bath. One secondary bedroom offers its own private balcony, the perfect place to enjoy morning coffee or peaceful evening breezes overlooking the beautifully landscaped yard. The partially finished lower level provides incredible flexibility with abundant storage and endless possibilities for a recreation room, home gym, media space, workshop, or future expansion. A convenient mud room adds everyday functionality to this already impressive home. Ideally located in the heart of Chesterfield, this exceptional property offers easy access to premier shopping, dining, parks, major highways, and award-winning Parkway schools. Combining the neighborhood's largest floor plan, extensive updates, outstanding outdoor living, and an unbeatable location, this is a rare opportunity to own a truly special home.

2156 Courtleigh Ln, Chesterfield