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135 Windy City Rd
Jackson TN 38305 US

$800,000

Active Listing ID 12017506
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5 bed
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5,671 square feet
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5.00 Bath (4 Full , 1 Half)
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Lot: 20.00 Acres
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Other

$800,000

Active Listing ID 12017506
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135 Windy City Rd 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.

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Property Features

  • Facts
  • Lot Size: 20.00 Acres
  • Property Type: Residential
  • Property Sub-type: Other
  • Features
  • Full Bathrooms: 4
  • 1/2 Bathrooms: 1
  • Floor Covering: Tile, Hardwood, Carpet
  • Roof Type: Asphalt
  • Heating Fuels: Propane (Heating), Heat Pump (Heating)
  • Additional Features
  • Fireplace
  • Patio
  • Pool

Property

  • propertytype: Residential
  • propertysubtype: Other
  • listprice: 800000
  • unparsedaddress: 135 Windy City Rd
  • postalcity: Jackson
  • stateorprovince: TN
  • country: US
  • postalcode: 38305
  • bathroomsfull: 4
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 20
  • lotsizeunits: Acres
  • lotsizearea: 20
  • livingarea: 5671
  • livingareaunits: Square Feet
  • latitude: 35.69733
  • longitude: -88.909015
  • listagentfullname: William Mclemore
  • listagentemail: targetmsbroker@gmail.com
  • listagentkey: 3yd-NYSMLS-148985
  • listagentmlsid: 148985
  • listagentofficephone: 8004763939
  • listofficekey: 3yd-NYSMLS-9504
  • listofficemlsid: 9504
  • disclaimer: 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.
  • sourcesystemid: NYSMLS
  • yearbuilt: 1999
  • listingcontractdate: 2026-10-07
  • countyorparish: Madison
  • parcelnumber: 032 02700 000
  • constructionmaterials: Brick
  • flooring: Tile, Hardwood, Carpet
  • heating: Propane (Heating), Heat Pump (Heating)
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Driveway
  • roof: Asphalt
  • waterfrontyn: False
  • franchiseaffiliation: None
  • interiorfeatures: Walk-In Closet(s), Entrance Foyer, Master Downstairs
  • rooms: Bedroom 2, Bedroom 1, Bedroom 3, Bathroom 3, Bedroom 5, Bathroom 1, Bedroom 4, Bathroom 2, Bathroom 4, Bathroom 5, Laundry Room
  • otherstructures: Workshop
  • patioandporchfeatures: Porch, Patio
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • fencing: Fenced
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -88.90901, 35.69733
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"TARGET AUCTION AND LAND CO INC", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"targetmsbroker@gmail.com", "ListBrokerageCity":"GADSDEN", "ListBrokerageCountry":"US", "ListBrokerageEmail":null, "ListBrokerageLogoUrl":null, "ListBrokerageName":"TARGET AUCTION AND LAND CO INC", "ListBrokeragePhone":null, "ListBrokeragePostalCode":null, "ListBrokerageStateOrProvince":"AL", "ListBrokerageUnitNumber":"Suite A", "ListBrokerageUnparsedAddress":"216 S 4th St", "ListBrokerageWebsiteUrl":null, "ListOfficeAddress1":"Suite A 216 S 4th St", "ListOfficeAddress2":"Suite A", "ListOfficeBrokerMlsId":"9504", "ListOfficeCity":"GADSDEN", "ListOfficeCountry":"US", "ListOfficeEmail":null, "ListOfficePostalCode":"35901", "ListOfficeStateOrProvince":"AL", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential, Jackson, TN", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/135-Windy-City-Rd_Jackson_TN_38305_M90087-64621?f=listhub&s=NYSMLS&m=12017506&c=rexren", "MLSModificationTimestamp":"2026-10-09 19:56:56", "Neighborhoods":[], "PostalCode":null, "RoomCount":null, "StateOrProvince":null, "Taxes":[], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 10/9/2026 8:59:36 PM GMT
Source Updated Date: 10/13/2026 12:46:36 AM GMT

Courtesy of: William Mclemore, Target Auction Company, targetmsbroker@gmail.com

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.