414 Fairholme Way

Off Market

414 Fairholme Way

Winchester KY 40391

2418 sq. ft.

16117 sq. ft.

Single-Family

Last sold for $484,900

Morgan Withrow, last sold this property on 13 August 2026 after 88 days on market.

Overview

Step into a lifestyle where modern luxury and brand-new construction come together seamlessly. This home is perfectly positioned with golf course views and unforgettable sunset skies, this newly built home offers the kind of setting that turns ordinary evenings into your favorite part of the day—without sacrificing style, comfort, or convenience. Inside, soaring vaulted ceilings and a warm fireplace create an inviting centerpiece for the open-concept living space—designed for both effortless entertaining and cozy nights at home. The timeless kitchen is equal parts beautiful and functional, featuring quartz countertops, a spacious walk-in pantry, and a dedicated coffee bar nook ready to elevate your morning routine. Just beyond, a dedicated dining area creates the perfect backdrop for weeknight dinners, holiday gatherings, and lingering conversations with family and friends. The primary suite feels like a private retreat, offering a spa-inspired en-suite complete with a soaking tub, tiled walk-in shower, dual vanities, and an expansive custom closet designed with luxury in mind. A split-bedroom floor plan provides ideal privacy with three additional bedrooms and two full bathrooms, creating flexibility for guests, family, or a home office setup. Outdoor living provides a screened back patio made for slow mornings, relaxing evenings, and enjoying the peaceful views. Whether you're gardening, unwinding after a long day, or gathering on the front porch with friends as the sun sets over the golf course, this space was designed to be enjoyed. And the location? Exceptional. Nestled just minutes from charming downtown Winchester's local shops, restaurants, and small-town charm, with quick access to I-64 for an easy commute. Plus, the oversized tall garage offers incredible vertical storage opportunities for hobbies, equipment, and all of life's extras. A rare opportunity to enjoy the ease of new construction, elevated design, and a lifestyle centered around comfort, connection, and beautiful surroundings. This isn't just a home—it's your next chapter.

Features

4 bedrooms

3 bathrooms

2 carspaces

2 garage spaces

2418 sq. ft. floor area

16117 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Winchester over the last 12 months, the estimated median property value of 414 Fairholme Way is $347k.

Median value

$347k

Estimated value range

$109.9k - $1.37m

Median days on market

Estimated value trend

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 414 Fairholme Way

2026

Sold

$484,900

13 Aug 2026 by Morgan Withrow, of The Brokerage

2025

Sold

$39,500

05 Mar 2025 by Garnett Davis, of Tom Goebel & Company

Happy sellers in Winchester

88%

88% 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 16 reviews in Winchester over the last 12 months.

Local market activity for 4 bedroom single-family properties in Winchester

In the last 12 months, 94 four-bedroom single-family properties similar to 414 Fairholme Way, have been sold.

This represents a 14% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Winchester for a market analysis.

Melissa Brown

at Keller Williams Legacy Group

(161 reviews)

Get a market analysis

Whitney Ensor

at Ensor Real Estate, LLC

(49 reviews)

Get a market analysis

Terry Powell

at Freedom Realty & Property Management

(81 reviews)

Get a market analysis

Jessica Noto

at Century 21 Advantage Realty

(50 reviews)

Get a market analysis

Nearby agents

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

Melissa Brown

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

5 (161 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 (49 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 (81 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, clear communication, responsive, friendly, stress-free process, and trustworthy