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Back 142 Clubhouse Drive
Off Market

142 Clubhouse Drive

Winchester KY 40391

6
4
2
4351 sq. ft.
Single-Family
Last sold for $650,000
Timothy SaylorTimothy Saylor, last sold this property on 17 June 2026 after 59 days on market.

Overview

Welcome to a lifestyle most only dream about — a stunning six-bedroom, four-bathroom residence perched along the lush fairways of Southwind Golf Course, complete with a lifetime membership for as long as you call this home. That's right, your morning coffee comes with panoramic views of manicured greens, and your evenings end with sunsets on the back porch. Inside, elegant double crown molding and wainscoting greet you in the entryway, setting a tone of refined sophistication throughout. The main level boasts nine-foot ceilings, a cozy family room anchored by a handsome fireplace, and a kitchen dressed in granite countertops and stainless steel appliances. The charming octagon-ceiling breakfast nook adds a touch of architectural whimsy to your morning routine. Upstairs, the primary bedroom features a stunning trey ceiling, while a conveniently located second-floor laundry room keeps daily chores effortless. The finished basement operates as a completely separate living space, offering its own kitchen, fireplace, and full bathroom — ideal for flexible living arrangements. Additional basement storage and a storm shelter/safe room beneath the porch provide practical peace of mind. Outside, a wraparound deck invites you to soak in those gorgeous views from every angle. Dual heating and cooling systems, poured concrete basement walls, and an oversized two-car garage round out this exceptional package. Nearby attractions include Winchester Traveling Trail and George Rogers Clark High School. Schedule your private tour today and discover what it feels like to live where every day feels like a getaway.

Features

6 bedrooms
4 bathrooms
2 carspaces
2 garage spaces
4351 sq. ft. floor area
Single-Family

Estimated Value

Based on this property and similar 6 bedroom single-family properties sold in Winchester over the last 12 months, the estimated median property value of 142 Clubhouse Drive is $619.5k.

Median value
$619.5k
Estimated value range
$325k - $750k
Median days on market
46
Estimated value trend
59%
increase over the last 12 months
Average days on market is based on recent, comparable sales in Winchester. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 142 Clubhouse Drive

2026
Sold
$650,000
17 Jun 2026 by Timothy Saylor, of Threshold Real Estate Services
2003
Sold
$275,000
24 Jan 2003 by Brenda Stewart, of REMAX Creative Realty | Georgetown

Happy sellers in Winchester

82%
82% of sellers in Winchester reported that their sale price either exceeded or met their price expectations.

Winchester stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 21 reviews in Winchester over the last 12 months.

Local market activity for 6 bedroom single-family properties in Winchester

In the last 12 months, 7 six-bedroom single-family properties similar to 142 Clubhouse Drive, have been sold.

This represents a 300% decrease in six-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Winchester

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Melissa Brown

Sellers who recommend Melissa Brown have praised them for being responsive, local expert, clear communication, supportive, friendly, dedicated, and detail-oriented

  •   5   (152 reviews)
  •  6 Reviews in Winchester
  •  8 Sales in Winchester
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Whitney Ensor

Sellers who recommend Whitney Ensor have praised them for being local expert, clear communication, supportive, friendly, reliable, responsive, and attentive

  •   5   (43 reviews)
  •  3 Reviews in Winchester
  •  4 Sales in Winchester
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Terry Powell

Terry Powell is a recommended agent for Winchester.  They have 4 local sales and collected 3 local reviews across the last 12 months.

  •   5   (80 reviews)
  •  3 Reviews in Winchester
  •  4 Sales in Winchester
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Jessica Noto

Sellers who recommend Jessica Noto have praised them for being local expert, dedicated, responsive, clear communication, friendly, stress-free process, and trustworthy

  •   5   (45 reviews)
  •  3 Reviews in Winchester
  •  2 Sales in Winchester
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