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Back 1105 Winding Way
Off Market

1105 Winding Way

Nashville-Davidson metropolitan government (balance) TN 37216

4
4
9
3800 sq. ft.
0.71 ac.
Single-Family
Last sold for $1,599,900
Robert DrimmerRobert Drimmer, last sold this property on 02 March 2026 after 46 days on market.

Overview

Absolutely breathtaking 1940s Tudor estate on one of East Nashville’s most beloved and picturesque streets, Winding Way. Set on nearly ¾ of an acre, this remarkable home feels like a true piece of neighborhood history—where timeless architecture, mature trees, and generations of memories come together. Inside, original hardwoods, exquisite moldings, oversized living spaces, and a glowing, fully functional fireplace immediately welcome you home. The thoughtfully renovated kitchen blends historic character with modern luxury, featuring a custom island, deVOL by Perrin & Rowe fixtures, Bosch, Bertazzoni, and Jenn-Air appliances, plus a stunning copper wet bar and butler’s pantry with an additional oven—perfect for gathering, celebrating, and entertaining. The main-level primary suite offers its own private sitting room, while upstairs you’ll find three spacious bedrooms and a newly added children’s bonus room. A massive unfinished basement provides incredible future potential, while the gated entry and three-car carport add both privacy and convenience. Directly across the street sits Jackson Park, and a private rear gate leads straight into Isaac Litton’s playground, making this a dream setting for families. Just steps to Mr. Aaron’s Bagels, Sip Coffee, Inglewood Library, and Riverside Village. Zoned for Dan Mills Elementary—this is a rare East Nashville legacy home where history and heart live side by side.

Features

4 bedrooms
4 bathrooms
9 carspaces
3 carport spaces
6 open car spaces
3800 sq. ft. floor area
0.71 ac. lot size
Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Nashville-Davidson metropolitan government (balance) over the last 12 months, the estimated median property value of 1105 Winding Way is $720k.

Median value
$720k
Estimated value range
$265k - $3.91m
Median days on market
21
Estimated value trend
-4%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Nashville-Davidson metropolitan government (balance). 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 1105 Winding Way

2026
Sold
$1,599,900
02 Mar 2026 by Robert Drimmer, of Compass Tennessee, LLC
2025
Sold
$1,454,000
02 Feb 2025 by Mike Geiger, of Benchmark Realty, LLC

Happy sellers in Nashville-Davidson metropolitan government (balance)

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We have insufficient information to provide an overview of customer satisfaction for Nashville-Davidson metropolitan government (balance). Viewing the agent profiles, reviews and sales for Nashville-Davidson metropolitan government (balance) can provide insights for this location.

Local market activity for 4 bedroom single-family properties in Nashville-Davidson metropolitan government (balance)

In the last 12 months, 64 four-bedroom single-family properties similar to 1105 Winding Way, have been sold.

This represents a 11% increase in four-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 Nashville-Davidson metropolitan government (balance)

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Brianna Morant

Brianna Morant is an award winning recommended agent for Nashville-Davidson metropolitan government (balance).  They have 11 local sales and collected 3 local reviews across the last 12 months.

  •   5   (8 reviews)
  •  3 Reviews in Nashville-Davidson metropolitan government (balance)
  •  11 Sales in Nashville-Davidson metropolitan government (balance)
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Sharon Wayman

Sharon Wayman is a recommended agent for Nashville-Davidson metropolitan government (balance).  They have 1 local sale and collected 1 local review across the last 12 months.

  •   4.8   (5 reviews)
  •  1 Review in Nashville-Davidson metropolitan government (balance)
  •  1 Sale in Nashville-Davidson metropolitan government (balance)
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Sydney Salati

Sydney Salati is a recommended agent for Nashville-Davidson metropolitan government (balance).  They have 1 local sale and collected 1 local review across the last 12 months.

  •   5   (8 reviews)
  •  1 Review in Nashville-Davidson metropolitan government (balance)
  •  1 Sale in Nashville-Davidson metropolitan government (balance)
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Jacqueline Beaudion

Jacqueline Beaudion is a recommended agent for Nashville-Davidson metropolitan government (balance).  They have collected 1 local review across the last 12 months.

  •   5   (8 reviews)
  •  1 Review in Nashville-Davidson metropolitan government (balance)
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