
Agricultural Land with Home for Sale in Jackson, Tennessee
135 Windy City Rd, Jackson, TN 38305
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.
Location
- Street address
- 135 Windy City Rd
- County
- Madison County
- School district
- Jackson Madison Consolidated District
- Elevation
- 435 feet
Property details
- Acreage
- 20 acres
- MLS #
- CWTAR 2600782
- Posted
Property taxes
- Recent
- $3,443
Parcels
- 032 027.00
Details and features
Listing
- Type
- Residential
- Subtype
- Single Family Residence
Lot
- Features
- Pasture
Exterior
- Parking Spaces
- 4
- Parking
- Driveway, Garage, Open
- Fencing
- Barbed Wire
- Pool
- Porch
- Features
- Rain Gutters
Structure
- Stories
- 2
- Water
- Well
- Sewer
- Septic Tank
- Cooling
- Ceiling Fan(s), Central Air
- Materials
- Brick
- Roof
- Composition, Shingle
Interior
- Room Count
- 14
- Rooms
- Bathroom x 5, Bedroom x 5, Bonus Room, Den, Dining Room, Laundry Room
- Flooring
- Carpet, Hardwood, Tile
- Appliances
- Bar Fridge, Dishwasher, Disposal, Double Oven, Gas Cooktop, Microwave, Refrigerator
- Features
- Bookcases, Breakfast Bar, Ceiling Fan(s), Central Vacuum, Commode Room, Crown Molding, Eat-In Kitchen, Entrance Foyer, Granite Counters, High Ceilings, Primary Downstairs, Untextured Ceilings, Walk-In Closet(s)
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| Feb 26, 2026 | New listing | $2,700,000 | — | CWTAR |



































































































