Winchester, TN homes for sale & real estate

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431 Haddon Ln, Winchester, TN 37398
431 Haddon Ln, Winchester, TN 37398
431 Haddon Ln, Winchester, TN 37398
ABOUT THIS HOME
Winchester, TN Homes for Sale
Quaint country living with endless potential and just minutes from Tims Ford Lake! Escape the hustle and embrace the peace and privacy of country living on this beautiful 1.76-acre property, perfectly located just a short drive from town conveniences and the recreational paradise of Tims Ford Lake, all with no city taxes! This 3-bedroom, 2-bath home offers 1,176 SF of comfortable main-level living, complete with a brand-new HVAC system, a 2-car garage, and a full basement with exciting potential for expansion. The basement already features a wood stove and kitchenette area, making it an ideal space for a second living area, workshop, or guest suite. Outdoors, the property continues to imp

$310,000

3 beds2 baths1,776 sq ft

431 Haddon Ln, Winchester, TN 37398

1.76 acre lot • 2 garage spots • Car-dependent

Listing provided by REALTRACS as Distributed by MLS Grid

816 S High St, Winchester, TN 37398
816 S High St, Winchester, TN 37398
816 S High St, Winchester, TN 37398
ABOUT THIS HOME
Winchester, TN Homes for Sale
Cozy and updated , this home has front porch with a swing and a back porch to relax on. Freshly painted in a neutral color with gray LVP flooring through out, bedrooms have new carpet. New lighting and custom cabinets. Older home with a modern vibe. Also on the property is a metal garage building with wood built workshop attached . The garage work shop has power and water. This house has central heat and airwith gas pack and it has natural gas heat as a back up heat source.

$198,500

3 beds1 bath1,100 sq ft

816 S High St, Winchester, TN 37398

0.24 acre lot • 2 garage spots • Car-dependent

Listing provided by REALTRACS as Distributed by MLS Grid

715 N High St N, Winchester, TN 37398
715 N High St N, Winchester, TN 37398
715 N High St N, Winchester, TN 37398
ABOUT THIS HOME
Winchester, TN Homes for Sale
Vintage Home or a cozy retreat from the busy world either would be perfect with this beautiful space. Located in a neighborhood this charming older home exudes character and custom warmth. Original hardwood floors offer ventage charm. With three cozy bedrooms and two full bathrooms, it offers the perfect blend of vintage charm and modern conveniences, making it an ideal setting for families or anyone looking to settle into a welcoming community. The house is not just a structure; it’s a sanctuary where memories are made. As you approach the home, you’ll be greeted by its inviting façade. The classic architecture features a combination of old and new. Check out the lovely

$229,000

3 beds2 baths1,360 sq ft

715 N High St N, Winchester, TN 37398

6,534 sq ft lot • Car-dependent

Listing provided by REALTRACS as Distributed by MLS Grid

NEW CONSTRUCTION

712 Fanning Bend Dr, Winchester, TN 37398
712 Fanning Bend Dr, Winchester, TN 37398
712 Fanning Bend Dr, Winchester, TN 37398
ABOUT THIS HOME
Winchester, TN Homes for Sale
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

0.42 acre lot • $275 HOA • 2 garage spots

Listing provided by REALTRACS as Distributed by MLS Grid

1200 Little St, Winchester, TN 37398
1200 Little St, Winchester, TN 37398
1200 Little St, Winchester, TN 37398
ABOUT THIS HOME
Winchester, TN Homes for Sale
INVESTOR SPECTIAL - CASH ONLY!!! Looking to add to your portfolio? Or just looking to bring life back into a House? Bring your ideas and get creative!

$130,000

4 beds2 baths1,588 sq ft

1200 Little St, Winchester, TN 37398

0.54 acre lot • Car-dependent

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 317 1st Ave SW, Winchester, TN 37398, 4 beds, 2 baths

$225,000

4 beds2 baths2,776 sq ft

317 1st Ave SW, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 71 Windjammer Ct, Winchester, TN 37398, 4 beds, 3.5 baths

$799,000

4 beds3.5 baths3,017 sq ft

71 Windjammer Ct, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 285 Crimson Dr, Winchester, TN 37398, 3 beds, 2 baths

$324,000

3 beds2 baths1,761 sq ft

285 Crimson Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 146 Island Way, Winchester, TN 37398, 4 beds, 3 baths

$519,900

4 beds3 baths2,578 sq ft

146 Island Way, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 407 Girton St, Winchester, TN 37398, 3 beds, 2 baths

$349,900

3 beds2 baths1,575 sq ft

407 Girton St, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 0 Moorehead Ln, Winchester, TN 37398, 3 beds, 3.5 baths

$1,800,000

3 beds3.5 baths3,638 sq ft

0 Moorehead Ln, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 120 Pontoon Pl, Winchester, TN 37398, 3 beds, 2.5 baths

$699,900

3 beds2.5 baths2,317 sq ft

120 Pontoon Pl, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 362 Chase Cir, Winchester, TN 37398, 2 beds, 2 baths

$354,900

2 beds2 baths1,701 sq ft

362 Chase Cir, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 136 Bel Aire Dr, Winchester, TN 37398, 3 beds, 2 baths

$285,000

3 beds2 baths1,944 sq ft

136 Bel Aire Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 142 Dry Creek Ln, Winchester, TN 37398, 3 beds, 2 baths

$355,900

3 beds2 baths2,166 sq ft

142 Dry Creek Ln, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 58 Island Way, Winchester, TN 37398, 4 beds, 2.5 baths

$469,000

4 beds2.5 baths2,305 sq ft

58 Island Way, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 209 Franklin Park, Winchester, TN 37398, 3 beds, 2 baths

$335,000

3 beds2 baths2,053 sq ft

209 Franklin Park, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 159 Canoe Ct, Winchester, TN 37398, 4 beds, 2.5 baths

$489,900

4 beds2.5 baths2,232 sq ft

159 Canoe Ct, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 419 Strawberry Dr, Winchester, TN 37398, 3 beds, 2 baths

$301,000

3 beds2 baths1,460 sq ft

419 Strawberry Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 811 Cumberland Dr, Winchester, TN 37398, 3 beds, 2 baths

$269,900

3 beds2 baths1,418 sq ft

811 Cumberland Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 806 Pleasant View Dr, Winchester, TN 37398, 3 beds, 2 baths

$279,900

3 beds2 baths1,759 sq ft

806 Pleasant View Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 144 Wood Bluff Rd, Winchester, TN 37398, 4 beds, 3 baths

$439,000

4 beds3 baths2,528 sq ft

144 Wood Bluff Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 2301 Old Estill Springs Rd, Winchester, TN 37398

$1,050,000

— beds— baths— sq ft

2301 Old Estill Springs Rd, Winchester, TN 37398

Property at 147 Crimson Dr, Winchester, TN 37398, 3 beds, 2 baths

$369,900

3 beds2 baths1,773 sq ft

147 Crimson Dr, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 117 Raspberry Dr, Winchester, TN 37398, 3 beds, 2 baths

$299,000

3 beds2 baths1,489 sq ft

117 Raspberry 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

$1,099,000

3 beds4 baths3,258 sq ft

98 Whippoorwill Cove Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 215 S Porter St #215, Winchester, TN 37398, 3 beds, 2.5 baths

$279,900

3 beds2.5 baths1,575 sq ft

215 S Porter St #215, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 213 S Porter St #213, Winchester, TN 37398, 3 beds, 2.5 baths

$279,900

3 beds2.5 baths1,575 sq ft

213 S Porter St #213, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 211 Porter St #211, Winchester, TN 37398, 3 beds, 2.5 baths

$279,900

3 beds2.5 baths1,575 sq ft

211 Porter St #211, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 217 S Porter St S #217, Winchester, TN 37398, 3 beds, 2.5 baths

$279,900

3 beds2.5 baths1,575 sq ft

217 S Porter St S #217, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 512 River Watch Way, Winchester, TN 37398, 4 beds, 3.5 baths

$620,000

4 beds3.5 baths3,042 sq ft

512 River Watch Way, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 62 Modena Pl, Decherd, TN 37324, 3 beds, 2 baths

$265,000

3 beds2 baths1,268 sq ft

62 Modena Pl, Decherd, TN 37324

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 18 Shady Cove Ln, Winchester, TN 37398, 3 beds, 2 baths

$649,900

3 beds2 baths1,788 sq ft

18 Shady Cove Ln, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 407 Style St, Winchester, TN 37398, 5 beds, 2 baths

$285,000

5 beds2 baths2,148 sq ft

407 Style St, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 137 Favre Cir, Winchester, TN 37398, 4 beds, 3 baths

$399,900

4 beds3 baths2,255 sq ft

137 Favre Cir, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 341 Carol Cir, Winchester, TN 37398, 4 beds, 2.5 baths

$344,900

4 beds2.5 baths1,788 sq ft

341 Carol Cir, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 287 Sisk Rd, Winchester, TN 37398, 4 beds, 3 baths

$475,000

4 beds3 baths2,580 sq ft

287 Sisk Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 6685 Lynchburg Rd, Winchester, TN 37398, 3 beds, 2 baths

$705,000

3 beds2 baths2,282 sq ft

6685 Lynchburg Rd, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 592 River Watch Way, Winchester, TN 37398, 4 beds, 3 baths

$529,000

4 beds3 baths2,275 sq ft

592 River Watch Way, Winchester, TN 37398

Listing provided by REALTRACS as Distributed by MLS Grid

Property at 759 Bluff Dr, Winchester, TN 37398, 3 beds, 2.5 baths

$849,000

3 beds2.5 baths2,450 sq ft

759 Bluff Dr, 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

Viewing page 2 of 6

Average home prices near Winchester, TN

Cities

Tracy City homes for sale
$356,400
Huntland homes for sale
$264,450
Cowan homes for sale
$224,900
Flintville homes for sale
$245,000
Estill Springs homes for sale
$320,000
Hillsboro homes for sale
$674,900
Orme homes for sale
Manchester homes for sale
$339,950
Lynchburg, Moore County homes for sale
$493,448
Sewanee homes for sale
$699,000
Tullahoma homes for sale
$346,000
Decherd homes for sale
$297,000
Normandy homes for sale
Monteagle homes for sale
$255,000
Pelham homes for sale
$574,900

Zip Codes

Winchester, TN real estate trends

All Home Types trends in Winchester, TN

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$345,000

-29.6% YoY | Jun 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Jun 2025

Growth

% YoY

Winchester, TN

$345,000

-29.6%

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Based on information submitted to the MLS GRID as of Thu Jul 17 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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