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$2,450,000 - 135 Windy City Rd, Jackson

5
Bedrooms
Baths
5,153
SQ. Feet
20
Acres

Extraordinary 20-Acre Private Estate with Pool & Equestrian Facilities - County-Only Taxes. Experience the perfect blend of luxury, privacy, and functionality with this breathtaking 5,153-square-foot estate set on 20 pristine acres. Featuring 5 bedrooms, 4 full baths, and 1 half bath, this remarkable property offers refined living in a peaceful country setting—just minutes from shopping, schools, and restaurants. A private driveway leads to the home's impressive circular front drive, setting the tone for the elegance within. Step inside the grand stair foyer entrance, flanked by formal living and dining rooms designed for entertaining. Hardwood floors grace the main downstairs living areas, while the inviting den features a vented gas log fireplace that can easily be converted to wood-burning with a gas starter. The spacious eat-in kitchen is beautifully appointed with beveled-edge granite countertops, a gas cooktop, double ovens, built-in microwave, dishwasher, and built-in refrigerator. The large breakfast area includes a charming window seat with storage and overlooks the stunning, brand-new French gray gunite QuartzScape saltwater pool and hot tub—your own private outdoor retreat. Just off the kitchen, a beautiful covered porch provides the perfect transition to the pool area, creating an ideal space for outdoor dining, entertaining, or simply relaxing while enjoying the view. A convenient full bath is located just off the kitchen, ideal for pool guests. The oversized laundry room offers abundant storage along with a built-in office area for added functionality. Upstairs you'll find four generously sized bedrooms, two full baths, and a large playroom with a second staircase leading downstairs—perfect for flexible living. Bedrooms are comfortably carpeted, and a spacious third-floor attic provides outstanding storage or future expansion possibilities. Equestrian enthusiasts will appreciate the impressive 2,300-square-foot barn complete with three stalls, hay loft

Essential Information

  • MLS® #:
    3155364
  • Price:
    $2,450,000
  • Bedrooms:
    5
  • Bathrooms:
    3.50
  • Full Baths:
    3
  • Half Baths:
    1
  • Square Footage:
    5,153
  • Acres:
    20.00
  • Year Built:
    1999
  • Type:
    Residential
  • Sub-Type:
    Single Family Residence
  • Status:
    Active

Community Information

  • Address:
    135 Windy City Rd
  • Subdivision:
    none
  • City:
    Jackson
  • County:
    Madison County, TN
  • State:
    TN
  • Zip Code:
    38305

Amenities

  • Utilities:
    Cable Connected
  • Parking Spaces:
    3
  • # of Garages:
    3
  • Garages:
    Garage Door Opener, Garage Faces Side

Interior

  • Interior Features:
    Entrance Foyer, Extra Closets, High Ceilings, Pantry, Walk-In Closet(s), High Speed Internet
  • Appliances:
    Double Oven, Cooktop, Dishwasher, Disposal, Refrigerator
  • Heating:
    Central, Propane
  • Cooling:
    Ceiling Fan(s), Central Air
  • # of Stories:
    2

Exterior

  • Construction:
    Brick

School Information

  • Elementary:
    Pope School
  • Middle:
    Northeast Middle School
  • High:
    North Side High School

Additional Information

  • Date Listed:
    March 20th, 2026
  • Days on Market:
    11

Listing Details

  • Listing Office:
    Nest Realty Jackson

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Disclaimer: All information is believed to be accurate but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal.

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Listing information last updated on April 1st, 2026 at 4:54am CDT.