MIDDLE TENNESSEE REAL ESTATE MIDDLE TENNESSEE REAL ESTATE
135 Windy City Rd TN 38305 For Sale -
135 Windy City Rd TN 38305 For Sale - 1
135 Windy City Rd TN 38305 For Sale - 2
135 Windy City Rd TN 38305 For Sale - 3
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135 Windy City Rd, Jackson, TN 38305 For Sale

Single Family Residence

$2,450,000

  • Single Family Residence
  • Beds: 5
  • Baths: 4
  • 5,153 sq ft

Description

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

Property Details

  • Status : Active

  • Address : 135 Windy City Rd Jackson TN 38305

  • County : Madison County, TN

  • Property Type : Residential

  • Area : 5,153 sq. ft.

  • Year Built : 1999

  • Exterior Construction : Brick

  • Floors : Carpet,Wood,Tile

  • Heat : Central,Propane

  • HOA / Subdivision : none

  • Listing Provided by : Nest Realty Jackson

  • MLS Status : Active

  • Listing # : RTC3155364

  • Schools near 135 Windy City Rd, Jackson, TN 38305 :

  • Pope School, Northeast Middle School, North Side High School

Additional details

  • Heating : Yes

  • Parking Features : Garage Door Opener,Garage Faces Side

  • Lot Size Area : 20 Sq. Ft.

  • Building Area Total : 5153 Sq. Ft.

  • Lot Size Acres : 20 Acres

  • Living Area : 5153 Sq. Ft.

  • Office Phone : 7312656800

  • Number of Bedrooms : 5

  • Number of Bathrooms : 4

  • Full Bathrooms : 3

  • Half Bathrooms : 1

  • Possession : Close Of Escrow

  • Cooling : 1

  • Garage Spaces : 3

  • Patio and Porch Features : Porch,Covered

  • Levels : One

  • Basement : Crawl Space

  • Stories : 2

  • Utilities : Cable Connected

  • Parking Space : 3

  • Sewer : Septic Tank

Location 135 Windy City Rd, TN 38305

Directions to 135 Windy City Rd, TN 38305

From the intersection of McClellan Road and Pleasant Plains Road, take McClellan Road to Windy City Road. Turn left onto Windy City and the house will be the second driveway on the right.

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