135 Windy City Rd
Jackson, TN, 38305 $ 2,450,000
Bedrooms5 Baths3.1 Sq 5,153 Monthly Estimate*
$ 15,085
for $2,450,000 with 5 bedrooms and 3 full baths, 1 half bath. This 5,153 square foot home was built in 1999 on a lot size of 20.
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
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FeaturesGeneralLiving Area 5153
Sewer Septic Tank
Heating Central Propane
Cooling Ceiling Fan(s) Central Air
Utilities Cable Connected
Possession Close Of Escrow
Appliances Double Oven Cooktop Dishwasher Disposal Refrigerator
Garage Spaces 3
Patio/Porch Features Porch Covered
Construction Materials Brick
Year Built 1999
Stories Count 2
Levels One
Property Subtype Single Family Residence
County Madison County TN
New Construction N
Property Type Residential
Attached Garage N
Subdivision Name none
Garage Y/N Y
Full Baths 3
Status Active
Directions 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.
High School North Side High School
City Jackson
Senior Community Y/N N
Lot Size Units Acres
Elementary School Pope School
Property Attached Y/N N
Year Built Details Approximate
Tax Annual Amount 3443
Middle/Junior High School Northeast Middle School
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
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InteriorInterior Amenities Entrance Foyer Extra Closets High Ceilings Pantry Walk-In Closet(s) High Speed Internet
Basement Crawl Space
Flooring Carpet Wood Tile
Air Conditioning Y/N Y
Heating Y/N Y
Above Grade Finished Area 5153
Half Baths 1
Laundry Features Electric Dryer Hookup Washer Hookup
Total Bedrooms 5
Main Level Bedrooms 1
Below Grade Finished Area Unit Type Square Feet
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 4
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ExteriorParking Features Garage Door Opener Garage Faces Side
Water Source Well
Total Parking 3
Lot Size Area 20
Building Area Total 5153
Lot Size Acres 20
Lot Size Source Assessor
Waterfront Y/N N
Covered Spaces 3
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* Excluded FeaturesList ByNest Realty JacksonBroker
suzanne.dement@nestrealty.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $15,085
- Monthly Property Taxes
- $287
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Jackson, TN
Average List Price $341,917
Percent of Sale Price 86%
About Jackson, TN 68,951 Population
9% Since 2002
$ 40,768 Median Income
35.51 Median Age
27% Households with Children
Trends Information provided by ATTOM Data Solutions.
4313899 Elementary School
3486693 Middle School
North Side High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 3/23/2026 | $2,450,000 | -9.26% | Price Down |
| 3/20/2026 | $2,700,000 | | Listed Price |