Luxury homes for sale & real estate in Winchester, TN

26 homes

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Recommended

$1,150,000

5 beds4.5 baths3,516 sq ft

45 Hammock Dr, Winchester, TN 37398

2 garage spots • Community pool • Built 2025

Listing provided by REALTRACS as Distributed by MLS Grid

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Winchester, TN:
A custom built home is located in prestigious Fanning Bend Subdivision. You must see this spectacular fully furnished home on Tim’s Ford Lake. Lake views from breakfast area deck & patio areas Completed in 2022, this luxury lake home features over 6100 SF, 6BR/ 5.5 BA, open floor plan w/ seamless flow into Kit, LR & DR areas. LR high ceiling & rock fireplace. Large kitchen custom cabinets ice maker w/ Frigidaire Gallery appliances featuring induction cooktop butlers pantry & granite counters. an off kitchen pantry to store all your goodies Primary BR suite w/ vaulted ceilings, lavish yourself in the adjoining bath including soak tub, walkin granite shower &amp

$1,499,500

6 beds5.5 baths6,176 sq ft

61 Joy Cir, Winchester, TN 37398

Induction cooktop • Open floor plan • Custom cabinets

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Luxury Home for sale in Winchester, TN:
Lake Luxury Awaits in Fanning Bend! Discover the pinnacle of Tims Ford Lake living in this stunning, maintained 4 bedroom, 3 bath home located on one of the largest lots in Fanning Bend Subdivision. The heart of this home is the exceptional outdoor living space. Enjoy the screened back porch, unwinding in the hot tub, or host friends around the custom backyard firepit. Step inside to an open-concept floor plan designed for effortless entertaining. The kitchen boasts with an island, quartz countertops, and pantry. Enjoy cozy nights by the gas log fireplace in the spacious living room. One bedroom & full bath located on the main level. Upstairs the primary suite features an extra-large,

$1,175,000

4 beds3 baths2,583 sq ft

71 Fanning Bend Dr, Winchester, TN 37398

Screened back porch • Gas log fireplace • Outdoor living space

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Luxury Home for sale in Winchester, TN:
Lakefront Luxury Below Appraised Value! Enjoy exceptionally peaceful mornings and breathtaking evening views of Tim's Ford Lake from your own covered back porch! Nestled in a quiet neighborhood with a community dock. This stunning home offers the perfect blend of community, beauty, and value. An unbeatable opportunity!!

$899,900

4 beds3.5 baths3,738 sq ft

101 Cypress Point Dr, Winchester, TN 37398

Lakefront • Community dock • Quiet neighborhood

Listing provided by REALTRACS as Distributed by MLS Grid

ABOUT THIS HOME
Luxury Home for sale in Winchester, TN:
Tims Ford LAKEFRONT | PRIVATE DOCK | Year-Round Lake Views | STR-Eligible | Move-In Ready Retreat Experience lake living at its best with this beautifully maintained 3BR/2.5BA (with flex space for family room, office or 4th bedroom) home offering year-round water views from nearly every window and your own private boat dock. Spanning 2,256 square feet, this home combines comfort, functionality, and a relaxed lake lifestyle. Enjoy hardwood floors, an open kitchen and living area, and a large lakeside deck ideal for entertaining or soaking in the views. Situated on a private 0.8-acre lot in a quiet, established neighborhood, this property provides the perfect balance of privacy and convenien

$999,900

3 beds2.5 baths2,256 sq ft

995 Dripping Springs Rd, Winchester, TN 37398

Lakefront • Pickleball court • Private dock

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 86 Simmons Cir, Winchester, TN 37398, 4 beds, 5 baths

$1,550,000

4 beds5 baths4,080 sq ft

86 Simmons Cir, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 740 Bluff Dr, Winchester, TN 37398, 4 beds, 3 baths

$1,849,000

4 beds3 baths2,800 sq ft

740 Bluff Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 1000 N Vine St, Winchester, TN 37398, 4 beds, 2 baths

$1,600,000

4 beds2 baths2,164 sq ft

1000 N Vine St, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 169 Joy Cir, Winchester, TN 37398, 3 beds, 3.5 baths

$1,350,000

3 beds3.5 baths3,183 sq ft

169 Joy Cir, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 138 Kayak Way, Winchester, TN 37398, 4 beds, 4.5 baths

$949,900

4 beds4.5 baths3,040 sq ft

138 Kayak Way, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 494 Cascade Dr, Winchester, TN 37398, 4 beds, 3.5 baths

$899,000

4 beds3.5 baths3,361 sq ft

494 Cascade Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 106 Clearview Cir, Winchester, TN 37398, 3 beds, 3 baths

$873,500

3 beds3 baths2,395 sq ft

106 Clearview Cir, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 2124 Boswell Rd, Winchester, TN 37398, 4 beds, 3.5 baths

$1,250,000

4 beds3.5 baths6,803 sq ft

2124 Boswell Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 155 Cypress Point Dr, Winchester, TN 37398, 3 beds, 2.5 baths

$869,900

3 beds2.5 baths2,236 sq ft

155 Cypress Point Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 73 Cypress Point Dr, Winchester, TN 37398, 4 beds, 3.5 baths

$899,999

4 beds3.5 baths2,684 sq ft

73 Cypress Point Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 97 Shady Cove Ln, Winchester, TN 37398, 2 beds, 3.5 baths

$2,100,000

2 beds3.5 baths3,410 sq ft

97 Shady Cove Ln, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at FB 217 Plan, Bg1ew8 Winchester, TN 37398, 4 beds, 4.5 baths

$1,329,000

4 beds4.5 baths3,492 sq ft

FB 217 Plan, Bg1ew8 Winchester, TN 37398

Listing provided by Zillow

Property at 712 Fanning Bnd #217, Winchester, TN 37398, 4 beds, 4.5 baths

$1,329,000

4 beds4.5 baths3,492 sq ft

712 Fanning Bnd #217, Winchester, TN 37398

Listing provided by Zillow

Property at 86 Simmons Cir #175, Winchester, TN 37398, 4 beds, 5 baths

$1,550,000

4 beds5 baths4,089 sq ft

86 Simmons Cir #175, Winchester, TN 37398

Listing provided by Zillow

Property at 208 Loop Dr, Winchester, TN 37398, 4 beds, 3.5 baths

$1,239,900

4 beds3.5 baths2,906 sq ft

208 Loop Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 98 Whippoorwill Cove Rd, Winchester, TN 37398, 3 beds, 4 baths

$998,000

3 beds4 baths3,258 sq ft

98 Whippoorwill Cove Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 279 Hammock Dr, Winchester, TN 37398, 4 beds, 3.5 baths

$949,900

4 beds3.5 baths3,341 sq ft

279 Hammock Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 1657 Boswell Rd, Winchester, TN 37398, 6 beds, 7 baths

$3,800,000

6 beds7 baths8,002 sq ft

1657 Boswell Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 3819 Tullahoma Hwy, Winchester, TN 37398

$1,800,000

— beds— baths— sq ft

3819 Tullahoma Hwy, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at FB 175 Plan, Winchester, TN 37398, 4 beds, 5 baths

$1,550,000

4 beds5 baths4,089 sq ft

FB 175 Plan, Winchester, TN 37398

Listing provided by Zillow

Property at 0 Nor Nan Rd, Decherd, TN 37324

$2,033,500

— beds— baths— sq ft

0 Nor Nan Rd, Decherd, TN 37324

Listing provided by REALTRACS as Distributed by MLS Grid

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Luxury Homes for Sale in Winchester

There are currently 26 luxury homes for sale in Winchester at a median listing price of $414K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winchester stay on the market for 105 days. Popular neighborhoods include Franklin Hills. This map is refreshed with the newest listings in Winchester every 15 minutes.

In the past month, 16 homes have been sold in Winchester. In addition to houses in Winchester, there was also 1 condo, 8 townhouses, and 2 multi-family units for sale in Winchester last month. Find your dream home in Winchester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winchester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winchester. Our Winchester real estate stats and trends will give you more information about home buying and selling trends in Winchester. If you're looking to sell your home in the Winchester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winchester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Based on information submitted to the MLS GRID as of Mon Dec 01 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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