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.
Closed
$1,599,900
1105 Winding Way, Nashville, TN 37216
4beds
3,800sqft
Single Family Residence, Residential
Built in 1941
0.71 Acres Lot
$1,599,800 Zestimate®
$421/sqft
$6,036 Estimated rent
Home value
$1,599,800
$1.52M - $1.68M
$6,036/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
Robert Drimmer 609-462-6636,
Compass Tennessee, LLC
Bought with:
Robert Drimmer, 321053
Compass Tennessee, LLC
Source: RealTracs MLS as distributed by MLS GRID,MLS#: 3080501
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
- Main level bedrooms: 1
Bedroom 1
- Features: Suite
- Level: Suite
- Area: 528 Square Feet
- Dimensions: 24x22
Bedroom 2
- Area: 270 Square Feet
- Dimensions: 18x15
Bedroom 3
- Area: 192 Square Feet
- Dimensions: 16x12
Bedroom 4
- Features: Bath
- Level: Bath
- Area: 289 Square Feet
- Dimensions: 17x17
Primary bathroom
- Features: Primary Bedroom
- Level: Primary Bedroom
Den
- Features: Paneled
- Level: Paneled
- Area: 238 Square Feet
- Dimensions: 17x14
Dining room
- Features: Formal
- Level: Formal
- Area: 144 Square Feet
- Dimensions: 12x12
Kitchen
- Area: 234 Square Feet
- Dimensions: 18x13
Living room
- Features: Great Room
- Level: Great Room
- Area: 216 Square Feet
- Dimensions: 18x12
Other
- Features: Office
- Level: Office
- Area: 132 Square Feet
- Dimensions: 12x11
Recreation room
- Area: 200 Square Feet
- Dimensions: 20x10
Heating
- Central, Electric, Natural Gas
Cooling
- Central Air, Electric
Appliances
- Included: Electric Oven, Gas Range, Dishwasher, Disposal, Refrigerator
- Laundry: Electric Dryer Hookup, Washer Hookup
Features
- Bookcases, Built-in Features, Extra Closets, High Ceilings, Pantry, Walk-In Closet(s), Wet Bar, Kitchen Island
- Flooring: Wood, Marble, Tile
- Basement: Full,Unfinished
- Number of fireplaces: 1
- Fireplace features: Family Room, Gas
Interior area
- Total structure area: 3,800
- Total interior livable area: 3,800 sqft
- Finished area above ground: 3,800
Property
Parking
- Total spaces: 9
- Parking features: Detached, Concrete, Driveway
- Carport spaces: 3
- Uncovered spaces: 6
Features
- Levels: Two
- Stories: 2
- Patio & porch: Porch, Covered
Lot
- Size: 0.71 Acres
- Dimensions: 143 x 250
Details
- Parcel number: 06107027900
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Tudor
- Property subtype: Single Family Residence, Residential
Materials
- Brick
- Roof: Shingle
Condition
- New construction: No
- Year built: 1941
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Electricity Available, Natural Gas Available, Water Available
Community & HOA
Community
- Subdivision: Jackson Park
HOA
- Has HOA: No
Location
- Region: Nashville
Financial & listing details
- Price per square foot: $421/sqft
- Tax assessed value: $1,272,400
- Annual tax amount: $6,597
- Date on market: 1/13/2026
- Electric utility on property: Yes
Price history
| Date | Event | Price |
|---|---|---|
| 3/2/2026 | Sold | $1,599,900$421/sqft |
Source:  RealTracs MLS as distributed by MLS GRID #3080501 Report a problem | ||
| 1/22/2026 | Contingent | $1,599,900$421/sqft |
Source: RealTracs MLS as distributed by MLS GRID #3080501 Report a problem | ||
| 1/14/2026 | Listed for sale | $1,599,900+10%$421/sqft |
Source: RealTracs MLS as distributed by MLS GRID #3080501 Report a problem | ||
| 2/2/2025 | Sold | $1,454,000$383/sqft |
Source: RealTracs MLS as distributed by MLS GRID #2769343 Report a problem | ||
| 12/22/2024 | Contingent | $1,454,000$383/sqft |
Source: RealTracs MLS as distributed by MLS GRID #2769343 Report a problem | ||
| 12/14/2024 | Listed for sale | $1,454,000+34.6%$383/sqft |
Source: RealTracs MLS as distributed by MLS GRID #2769343 Report a problem | ||
| 4/18/2022 | Sold | $1,080,000-10%$284/sqft |
Source: Public Record Report a problem | ||
| 11/10/2021 | Listing removed | -- |
Source: RealTracs MLS as distributed by MLS GRID #2282313 Report a problem | ||
| 8/20/2021 | Listed for sale | $1,200,000+216.6%$316/sqft |
Source: RealTracs MLS as distributed by MLS GRID #2282313 Report a problem | ||
| 2/5/2014 | Sold | $379,000-5.2%$100/sqft |
Source: Public Record Report a problem | ||
| 10/20/2013 | Price change | $399,900-2.4%$105/sqft |
Source: RE/MAX Choice Properties #1492115 Report a problem | ||
| 9/11/2013 | Price change | $409,900-4.7%$108/sqft |
Source: RE/MAX Choice Properties #1471150 Report a problem | ||
| 7/27/2013 | Listed for sale | $429,900+133%$113/sqft |
Source: TheDailyClassifieds.Com #1471150 Report a problem | ||
| 4/3/1998 | Sold | $184,500$49/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $8,951 +35.7% | $318,100 +56.9% |
| 2024 | $6,597 | $202,750 |
| 2023 | $6,597 -37.1% | $202,750 -37.1% |
| 2022 | $10,496 -1% | $322,560 |
| 2021 | $10,606 +9.8% | $322,560 +41% |
| 2020 | $9,656 +33.8% | $228,760 |
| 2019 | $7,217 | $228,760 |
| 2018 | $7,217 | $228,760 |
| 2017 | $7,217 | $228,760 +96.1% |
| 2016 | $7,217 +37% | $116,640 |
| 2015 | $5,267 | $116,640 |
| 2014 | $5,267 | $116,640 |
| 2013 | -- | $116,640 -7.3% |
| 2012 | -- | $125,880 |
| 2011 | -- | $125,880 |
| 2010 | -- | $125,880 |
| 2009 | -- | $125,880 +31% |
| 2008 | -- | $96,080 |
| 2007 | -- | $96,080 |
| 2006 | -- | -- |
| 2005 | -- | -- |
| 2004 | -- | -- |
| 2003 | -- | -- |
| 2002 | -- | -- |
| 2001 | -- | -- |
| 2000 | -- | -- |
Find assessor info on the county website
Neighborhood: Jackson Park Community Club
Nearby homes
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Nearby schools
GreatSchools rating
- 8/10Dan Mills Elementary SchoolGrades: PK-5Distance: 0.7 mi
- 6/10Isaac Litton Middle SchoolGrades: 6-8Distance: 0.2 mi
- 3/10Stratford Comp High SchoolGrades: 6-12Distance: 2.1 mi
Schools provided by the listing agent
- Elementary: Dan Mills Elementary
- Middle: Isaac Litton Middle
- High: Stratford STEM Magnet School Upper Campus
Source: RealTracs MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$1,599,800
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Estimated market value
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