# 135 Windy City Rd, Jackson, TN 38305 > **TL;DR:** 5bd/5ba single family, $800,000 ($141/sqft), built 1999, 5,671 sqft. > Pool, Fireplace, Hardwood, 3-car garage. Est. $4,278/mo. Listed 3 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $800,000 | | Price/sqft | $141 | | Bedrooms | 5 | | Bathrooms | 4 full, 1 half | | Square Feet | 5,671 | | Year Built | 1999 | | Lot Size | 871,200 sqft (20.00 acres) | | Garage | 3-car | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 3 | ## Why This Home Stands Out - **Pool** - Porch, Patio - **Large Garage** - 3-car garage - **Hardwood Floors** - Hardwood flooring listed ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $4,045 | | Estimated Insurance | $233 | | **Total** | **$4,278** | ## Key Amenities - Pool - Fireplace - Hardwood - 3-car garage ## Property Highlights - Built in 1999 - 20.00 acre lot - Private pool - Fireplace ## Description ### Agent Description ONLINE AUCTION - November 12th at 11:00 am CT. Starting Bid $800k. Please contact the auction company for questions and visit target more details. Set on 20 beautiful acres just outside the city limits, this remarkable estate offers the peace and privacy of the countryside while keeping top-rated schools, shopping, dining, and everyday conveniences only minutes away. A long drive bordered by classic white fencing winds through the property and leads to an elegant Neoclassical home with timeless Southern character and subtle European influence. A circular drive creates an impressive arrival at the 5,153+/--square-foot residence. Inside, the home offers five bedrooms and four-and-a-half bathrooms. An impressive foyer is flanked by formal living and dining rooms, while hardwood floors extend throughout the main level. The den provides a comfortable gathering space centered around a vented gas-log fireplace, and the spacious primary suite is conveniently located on the main floor. The well-appointed kitchen features beveled-edge granite countertops, a gas cooktop, double ovens, built-in refrigerator, and a large breakfast area. Upstairs are four generously sized bedrooms, two full bathrooms, and a large bonus or playroom with convenient access from a second staircase. Much of what makes this property special, however, is found outdoors. A beautiful rear porch overlooks the landscaped grounds and recently added Gunite QuartzScape saltwater pool and hot tub, creating a private resort-like setting for relaxing and entertaining. Beyond the pool, picturesque cross-fenced pastures stretch across the property, making the estate particularly well suited for horses. A paved drive continues to an impressive 2,300+/--square-foot barn featuring three stalls, a hay loft, tack room, and abundant storage. While ideal for equestrian use, the barn also offers excellent possibilities for a hobbyist, collector, or additional entertaining space. From the white-fenced drive and rolling pastures to the stately residence, resort-style pool, and substantial barn, this is a rare opportunity to enjoy 20 acres of country living while remaining just minutes from town. Agents are welcome. Twelve percent buyer's premium. ## Location - **Address:** 135 Windy City Rd, Jackson, TN 38305 - **County:** Madison - **Coordinates:** 35.69733, -88.909015 - **Google Maps:** https://www.google.com/maps?q=35.69733,-88.909015 ## Virtual Tour & Media - **Video Tour:** https://www.youtube.com/watch?v=VjIBgGxBllc ## Listing Agent - **Name:** William Mclemore - **Brokerage:** TARGET AUCTION AND LAND CO INC - **Broker Phone:** 8004763939 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/135-Windy-City-Rd_Jackson_TN_38305_M90087-64621?f=listhub&s=NYSMLS&m=12017506&c=propsimple) ## Photos ![135 Windy City Rd - Photo 1](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f3527717099r.jpg) ![135 Windy City Rd - Photo 2](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f1506072860r.jpg) ![135 Windy City Rd - Photo 3](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f1125276096r.jpg) ![135 Windy City Rd - Photo 4](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f1384139070r.jpg) ![135 Windy City Rd - Photo 5](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f995881665r.jpg) ![135 Windy City Rd - Photo 6](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f812071729r.jpg) ![135 Windy City Rd - Photo 7](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f3108498583r.jpg) ![135 Windy City Rd - Photo 8](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f846740122r.jpg) ![135 Windy City Rd - Photo 9](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f3523088967r.jpg) ![135 Windy City Rd - Photo 10](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f976239371r.jpg) ![135 Windy City Rd - Photo 11](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2814209316r.jpg) ![135 Windy City Rd - Photo 12](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f3444709487r.jpg) ![135 Windy City Rd - Photo 13](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f3281336575r.jpg) ![135 Windy City Rd - Photo 14](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f3594590321r.jpg) ![135 Windy City Rd - Photo 15](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f1326469471r.jpg) ![135 Windy City Rd - Photo 16](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2222609912r.jpg) ![135 Windy City Rd - Photo 17](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2519835994r.jpg) ![135 Windy City Rd - Photo 18](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2953061194r.jpg) ![135 Windy City Rd - Photo 19](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f1297307510r.jpg) ![135 Windy City Rd - Photo 20](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f3588137989r.jpg) ![135 Windy City Rd - Photo 21](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f1561155r.jpg) ![135 Windy City Rd - Photo 22](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2491977148r.jpg) ![135 Windy City Rd - Photo 23](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2880331216r.jpg) ![135 Windy City Rd - Photo 24](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f1562723879r.jpg) ![135 Windy City Rd - Photo 25](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2357279153r.jpg) ![135 Windy City Rd - Photo 26](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f1482626116r.jpg) ![135 Windy City Rd - Photo 27](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f3905554194r.jpg) ![135 Windy City Rd - Photo 28](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2910790298r.jpg) ![135 Windy City Rd - Photo 29](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f1400569024r.jpg) ![135 Windy City Rd - Photo 30](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f826515400r.jpg) ![135 Windy City Rd - Photo 31](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f4096656165r.jpg) ![135 Windy City Rd - Photo 32](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2662671768r.jpg) ![135 Windy City Rd - Photo 33](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f1997536360r.jpg) ![135 Windy City Rd - Photo 34](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2277439176r.jpg) ![135 Windy City Rd - Photo 35](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f3125547469r.jpg) ![135 Windy City Rd - Photo 36](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2193576820r.jpg) ![135 Windy City Rd - Photo 37](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f3658719711r.jpg) ![135 Windy City Rd - Photo 38](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2014337633r.jpg) ![135 Windy City Rd - Photo 39](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f1848000119r.jpg) ![135 Windy City Rd - Photo 40](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2246882328r.jpg) ![135 Windy City Rd - Photo 41](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f553775934r.jpg) ![135 Windy City Rd - Photo 42](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f4046605267r.jpg) ![135 Windy City Rd - Photo 43](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f3694273651r.jpg) ![135 Windy City Rd - Photo 44](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f4074043756r.jpg) ![135 Windy City Rd - Photo 45](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2659203483r.jpg) ![135 Windy City Rd - Photo 46](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f1431529333r.jpg) ![135 Windy City Rd - Photo 47](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f170787174r.jpg) ![135 Windy City Rd - Photo 48](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f1794535810r.jpg) ![135 Windy City Rd - Photo 49](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f131389437r.jpg) ![135 Windy City Rd - Photo 50](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f852058878r.jpg) ![135 Windy City Rd - Photo 51](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f133224489r.jpg) ![135 Windy City Rd - Photo 52](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f666845366r.jpg) ![135 Windy City Rd - Photo 53](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f3983880829r.jpg) ![135 Windy City Rd - Photo 54](http://lh.rdcpix.com/15fd9e32a3895254c11bdf7262e188dbl-f2755752440r.jpg) --- **MLS#:** 12017506 | **Updated:** 2026-10-09 **Source:** listhub *Copyright © 2026 My State MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/135-windy-city-rd-jackson-tn-38305-12017506) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/135-windy-city-rd-jackson-tn-38305-12017506#listing", "url": "https://www.propertysimple.ai/listing/135-windy-city-rd-jackson-tn-38305-12017506", "name": "135 Windy City Rd, Jackson, TN 38305", "description": "ONLINE AUCTION - November 12th at 11:00 am CT. Starting Bid $800k. Please contact the auction company for questions and visit target more details. Set on 20 beautiful acres just outside the city limits, this remarkable estate offers the peace and privacy of the countryside while keeping top-rated schools, shopping, dining, and everyday conveniences only minutes away. A long drive bordered by classic white fencing winds through the property and leads to an elegant Neoclassical home with timeless Southern character and subtle European influence. A circular drive creates an impressive arrival at the 5,153+/--square-foot residence. Inside, the home offers five bedrooms and four-and-a-half bathrooms. An impressive foyer is flanked by formal living and dining rooms, while hardwood floors extend throughout the main level. The den provides a comfortable gathering space centered around a vented gas-log fireplace, and the spacious primary suite is conveniently located on the main floor. The well-appointed kitchen features beveled-edge granite countertops, a gas cooktop, double ovens, built-in refrigerator, and a large breakfast area. Upstairs are four generously sized bedrooms, two full bathrooms, and a large bonus or playroom with convenient access from a second staircase. Much of what makes this property special, however, is found outdoors. A beautiful rear porch overlooks the landscaped grounds and recently added Gunite QuartzScape saltwater pool and hot tub, creating a private resort-like setting for relaxing and entertaining. Beyond the pool, picturesque cross-fenced pastures stretch across the property, making the estate particularly well suited for horses. A paved drive continues to an impressive 2,300+/--square-foot barn featuring three stalls, a hay loft, tack room, and abundant storage. While ideal for equestrian use, the barn also offers excellent possibilities for a hobbyist, collector, or additional entertaining space. From the white-fenced drive and rolling pastures to the stately residence, resort-style pool, and substantial barn, this is a rare opportunity to enjoy 20 acres of country living while remaining just minutes from town. Agents are welcome. 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