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105 Shady Valley Drive, Chesterfield, MO, 63017

A rare mid-century modern masterpiece on over an acre in River Bend Estates, this 1968 architectural jewel offers 4 bedrooms, 3.5 bathrooms, and 3,063 square feet of organic design, lovingly preserved by just three owners in nearly six decades. A stunning original wood front door leads into a dramatic entry foyer, opening to a sunlit floor plan anchored by a magnificent two-sided brick fireplace that warms both the formal living and family rooms. Complete with classic parquet wood floors, built-in MCM shelving, and massive windows framing treetop views, every corner honors its iconic heritage. The home flows naturally toward a sunlit breakfast room, which opens to a serene screened porch for seamless outdoor dining. Designed for ultimate flexibility, the layout features dual primary suites—one on the main level opening directly to the private outdoor grounds, and a second-level retreat with a dedicated sitting area and a balcony. Key infrastructure updates like a newer roof (2022) and high-efficiency HVAC provide peace of mind, leaving you free to customize the remaining spaces to your personal style. The flat acre+ lot backs to woods creating an exceptionally private space that features a sprawling brick patio made for entertaining. A partially finished basement ready for a gym or media room, main-level laundry, and an oversized two-car garage round out this amazing home. Located in the highly sought-after River Bend neighborhood where a vibrant community center with a pool (optional annual membership/fees apply) and year-round activities quickly make friends of neighbors, this home is as welcoming as it is historic.

Subdivision: River Bend Estates 1

List Price

$ 549,000

Status

Active Under Contract

Days on market

0

MLS#

26045473

Bedrooms

4

Full baths

4

Sq. Ft. Above

3,063

Subdivision

River Bend Estates 1

Municipality

Chesterfield

School District

Parkway C-2

County

St Louis

Property Type

Residential

Style

Modern

Type

Residential

Additional Information

Property Tax (2025)

$6,810

Recent Nearby Sales in 63017

Last 6 closed homes in this zip.

Address Bd/Ba SqFt List Sold Closed
2319 Wellington Estates Drive, Chesterfield, MO 63017 4/4 3,274 $795,000 $855,000
107.5% of ask
Sep 4, 2026
357 Cooperstown Drive, Chesterfield, MO 63017 4/3 2,524 $499,000 $475,000
95.2% of ask
Sep 4, 2026
14120 Baywood Villages Drive, Chesterfield, MO 63017 3/3 2,610 $549,900 $525,000
95.5% of ask
Sep 3, 2026
1506 Timber Point Court, Chesterfield, MO 63017 4/3 2,246 $650,000 $733,000
112.8% of ask
Sep 3, 2026
166 Southdown Drive, Chesterfield, MO 63017 5/4 2,486 $525,000 $522,000
99.4% of ask
Sep 3, 2026
113 High Valley Drive, Chesterfield, MO 63017 4/2 2,090 $529,900 $522,500
98.6% of ask
Sep 3, 2026

Price & Listing History

Listed for sale
Aug 16, 2026 at $549,000
Current status: Active Under Contract
As of Aug 18, 2026 · $549,000

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