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$2,700,000
3 Days On Site

135 Windy City Road
Jackson, TN 38305

For Sale|Single Family Residence|Active
5
Beds
5
Total Baths
4
Full Baths
1
Partial Bath
5,153
SqFt
$524
/SqFt
1999
Built
Subdivision:
None
County:
Madison
Listing courtesy of Traci Carney of Nest Realty (731) 343-1478
Call Now: (731) 506-0999
Is this the listing for you? We can help make it yours.
(731) 506-0999
135 Windy City Road135 Windy City Road135 Windy City Road135 Windy City Road
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Monthly Payment (Est.)

$12,319
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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, and tack room. Three separate pasture areas with classic white vinyl fencing provide ample grazing space, with two pastures offering direct access from the barn for added convenience. Additional features include a two-car attached garage at the home and a separate one-car garage—ideal for golf cart storage or extra equipment. This exceptional estate delivers luxury living, equestrian amenities, and serene privacy—all with county-only taxes—creating a rare opportunity to enjoy the best of country living without sacrificing modern conveniences.

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Listing Snapshot
Price 
$2,700,000
Days On Site 
3 Days
Bedrooms 
5
Inside Area (SqFt) 
5,153 sqft
Total Baths 
5
Full Baths 
4
Partial Baths 
1
Lot Size 
20 Acres
Year Built 
1999
MLS® Number 
2600782
Status 
Active
Property Tax 
$3,443.21
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
Assessor
Friends & Family
Recent Activity
3 days agoListing first seen on site
3 days agoListing updated with changes from the MLS®
General Features
Acres 
20
Attached Garage 
Yes
Foundation 
Raised
Garage 
Yes
Garage Spaces 
3
Levels 
Two
Number Of Stories 
2
Parking 
Circular DrivewayGarage Door OpenerGarage Faces SideAttached
Parking Spaces 
4
Property Sub Type 
Single Family Residence
Sewer 
Septic Tank
Special Circumstances 
Standard
Utilities 
Cable AvailableElectricity ConnectedPhone AvailableSewer ConnectedWater ConnectedPropaneUnderground Utilities
Water Source 
PrivateWell
Interior Features
Appliances 
Bar FridgeDishwasherDisposalDouble OvenGas CooktopMicrowaveRefrigerator
Cooling 
Ceiling Fan(s)Central AirOther
Fireplace 
Yes
Fireplace Features 
Gas LogGas StarterWood Burning
Flooring 
CarpetHardwoodTile
Heating 
See Remarks
Interior 
BookcasesBreakfast BarCeiling Fan(s)Central VacuumCrown MoldingEat-in KitchenEntrance FoyerGranite CountersHigh CeilingsWalk-In Closet(s)
Laundry Features 
Main Level
Main Level Bedrooms 
1
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Exterior Features
Construction Details 
Brick
Exterior 
Rain GuttersOther
Fencing 
Barbed WireSplit RailVinylWood
Lot Features 
Pasture
Other Structures 
Barn(s)Stable(s)
Patio And Porch 
CoveredFront PorchRear Porch
Pool Features 
GuniteIn GroundOutdoor PoolPool/Spa ComboPrivateSalt Water
Private Pool 
Yes
Road Frontage 
County Road
Roof 
CompositionShingle
Community Features
Roads 
Asphalt
School District 
Jackson Madison Consolidated District
Schools
School District
Jackson Madison Consolidated District
Elementary School
Unknown
Middle School
Unknown
High School
Unknown
Listing courtesy of Traci Carney of Nest Realty (731) 343-1478



Listing information is provided by Participants of the Central West Tennessee Association of Realtors MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Copyright 2026, Central West Tennessee Association of Realtors MLS.
Last checked 2026-03-01 09:47 PM UTC

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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