377 Crescent Ave

Off Market

377 Crescent Ave

Winchester KY 40391

1533 sq. ft.

8276 sq. ft.

Single-Family

Last sold for $239,900

W Bill VanWinkle, last sold this property on 23 October 2026 after 134 days on market.

Overview

"Motivated sellers—bring your offers!" Step into this charming 3-bedroom, 2-bath home that's full of character and timeless appeal. From the beautiful hardwood floors to the inviting living spaces, this older home offers warmth and personality you simply don't find in newer construction. The spacious living room provides plenty of room to relax or entertain, while the separate dining room is perfect for family meals and special gatherings. The large kitchen offers abundant space for cooking, storage, and everyday living. Outside, you'll enjoy a fully fenced backyard that's ideal for children, pets, gardening, or outdoor entertaining. Sip your morning coffee on the welcoming covered front porch or unwind on the back deck overlooking the private yard. This home offers the perfect combination of classic charm, generous living space, and inviting outdoor areas. All this in a great location, just minutes from Lexington, the horse capital of the world, with beautiful Kentucky horse farms! And just 45 minutes from the famous Red River Gorge! This home is right in the center of it all, city life and the beautiful outdoors! Don't miss this wonderful opportunity to make this charming home your own!

Features

3 bedrooms

2 bathrooms

1533 sq. ft. floor area

8276 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Winchester over the last 12 months, the estimated median property value of 377 Crescent Ave is $263.25k.

Median value

$263.25k

Estimated value range

$39.6k - $880k

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 377 Crescent Ave

2026

Sold

$239,900

23 Oct 2026 by W Bill VanWinkle, of Joyce Marcum Realty

2024

Sold

$219,900

02 Feb 2024 by Lori Tolson, of United Real Estate Lexington

2020

Sold

$160,000

29 May 2020 by Richard Abney, of Realty World Adams & Associates

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 3 bedroom single-family properties in Winchester

In the last 12 months, 210 three-bedroom single-family properties similar to 377 Crescent Ave, have been sold.

This represents a 17% increase in three-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

(160 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

(49 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 (160 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

View profile

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

View profile

Jessica Noto

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