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

Jackson, TN, 38305
$ 2,450,000
Bedrooms5 Baths3.1 Sq 5,153

Monthly Estimate*

$ 15,085

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Single Family Home for sale in Jackson, TN

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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Single Family Active

Price

$ 2,450,000

Bedrooms

5

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 3,443

Style

Lot Size

20

Year Built

1999

Town/City

Jackson

County/Region

Madison

MLS | Web ID

3155364

Features
General
Living 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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Interior
Interior 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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Exterior
Parking 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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Internal Only
Street Number 1 135
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* Excluded Features
List By
Nest Realty Jackson

Broker

suzanne.dement@nestrealty.com

Email

Affordability Calculator

$15,372
Per Month
98%
2%
0%
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.
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Nearby
4313899 Elementary School
3486693 Middle School
North Side High School High School
Pricing History
DatePricePrice ChangeDescription
3/23/2026$2,450,000 -9.26% Price Down
3/20/2026$2,700,000 Listed Price

Map


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135 Windy City Rd, Jackson, TN, 38305 is a Single Family Home for sale at $2,450,000 with 5,153 sqft and a lot size of 20. 135 Windy City Rd has 5 bedrooms, 3.1 baths, and was built in 1999. The property's zip code is 38305 which is in Jackson, TN