Luxury homes for sale & real estate in Winchester, TN

27 homes

Sort:

Recommended

NEW

ABOUT THIS HOME
Luxury Home for sale in Winchester, TN:
Experience the epitome of lakeside living in this magnificent 5-bedroom, 4-bathroom retreat nestled in the prestigious Fanning Bend community, crafted w excellence by Legacy South. Boasting panoramic views of the sparkling waters & surrounded by nature's tranquility, this home offers an unparalleled blend of luxury & serenity. Step inside to discover an open & airy floor plan, accentuated by expansive windows that frame the mesmerizing lake views. The main living area is ideal for both relaxation and entertainment, w a seamless flow between the living room, dining area, & chef's kitchen. Channel your inner chef in the gourmet kitchen, equipped with top-of-the-line Jen

$1,750,000

6 beds7 baths4,778 sq ft

959 Fanning Bend Dr, Winchester, TN 37398

Custom cabinetry • Quartz countertops • Lakeside living

Listing provided by REALTRACS as Distributed by MLS Grid

NEW

ABOUT THIS HOME
Luxury Home for sale in Winchester, TN:
Luxury living at Fanning Bend. This home blends casual lake life with elevated design. The sun-lit living area features wide-plank hardwoods, a stone fireplace, and a wall of windows that opens to the surrounding woods and lake. The kitchen stands out with natural wood cabinetry, designer lighting and backsplash, and a spacious island—perfect for gathering. Upstairs you’ll find a large bonus room and another covered balcony space overlooking the lake. A deeded boat slip comes with the home, and the community pool and walkable neighborhood keep the outdoors close. Inside, thoughtful touches like a herringbone-tiled mudroom and generous guest spaces make it as functional as it is

$1,329,000

4 beds4.5 baths3,492 sq ft

712 Fanning Bend Dr, Winchester, TN 37398

Large bonus room • Community pool • Deeded boat slip

Listing provided by REALTRACS as Distributed by MLS Grid

$1,150,000

5 beds4.5 baths3,596 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

Property at 101 Cypress Point Dr, Winchester, TN 37398, 4 beds, 3.5 baths

$899,900

4 beds3.5 baths3,738 sq ft

101 Cypress Point Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 995 Dripping Springs Rd, Winchester, TN 37398, 3 beds, 2.5 baths

$999,900

3 beds2.5 baths2,256 sq ft

995 Dripping Springs Rd, Winchester, TN 37398

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 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 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 1750 Awalt Dr, Winchester, TN 37398, 5 beds, 4.5 baths

$1,599,000

5 beds4.5 baths3,797 sq ft

1750 Awalt Dr, 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 405 Sharp Springs Rd, Winchester, TN 37398

$1,500,000

— beds— baths— sq ft

405 Sharp Springs 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

Viewing page 1 of 1

Luxury Homes for Sale in Winchester

There are currently 27 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.

More real estate resources for Winchester, TN

Neighborhoods

Franklin Hills homes for sale

Nearby Cities

Zip Codes

Nearby Cities with Luxury Homes

More to explore in Winchester, TN

Featured
Price

How to buy a house in Winchester, TN

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Tennessee

Based on information submitted to the MLS GRID as of Wed Dec 03 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.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.