252 Loop Dr, Winchester, TN 37398
Property image
Property image
OFF MARKET

$624,600

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 1,632 sqft (on 0.73 acres)

252 Loop Dr, Winchester, TN 37398

Est. Refi. Payment $3,815/mo*
Refinance Your Home
Currently Off Market - Sold Aug 19, 2019 for $365,000

Home Value

Trulia Estimate
$625K
Since last month
Decreased$4K (-0.6%)
Since last year
Decreased$22K (-3.3%)
Since last sale
Increased$260K (+71.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +100% in the last 10 years
MonthEstimated value
2026
September 2026$625K
September 2026$625K
August 2026$629K
July 2026$633K
June 2026$641K
May 2026$631K
April 2026$626K
March 2026$616K
February 2026$602K
January 2026$603K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
118 Hickory Hill Dr, Estill Springs, TN
0.44
Single-Family Home
$365,000
05/07/26
3
3
3,022
76 Waters Edge Dr, Estill Springs, TN
0.79
Single-Family Home
$399,900
12/29/25
3
2
1,843
1956 Old Estill Springs Rd, Winchester, TN
0.97
Single-Family Home
$295,000
04/30/26
3
1.5
1,668
38 Murray Lake Dr, Winchester, TN
1.29
Single-Family Home
$314,000
09/12/26
2
2
1,683
353 Waters Edge Dr, Estill Springs, TN
0.63
Single-Family Home
$1,350,000
06/25/26
3
2.5
3,266
461 Royal Oak Dr, Winchester, TN
1.28
Single-Family Home
$374,900
11/05/25
3
2
2,247
1896 Eastbrook Rd, Estill Springs, TN
1.30
Single-Family Home
$365,000
11/24/25
3
2
2,042
116 Elkins St, Estill Springs, TN
1.48
Single-Family Home
$320,000
02/27/26
3
2
1,714
100 Acree Ln, Estill Springs, TN
0.46
Single-Family Home
$2,075,000
09/23/26
4
4
2,200
215 Hill St, Estill Springs, TN
1.42
Single-Family Home
$300,000
09/30/26
3
2
1,846

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
272 Loop Dr, Winchester, TN 37398
0.02
$536,200
Studio
2
816
Off Market
232 Loop Dr, Winchester, TN 37398
0.02
$986,800
5
4.5
3,648
Off Market
208 Loop Dr, Winchester, TN 37398
0.05
$1,050,000
4
3.5
2,906
For Sale
292 Loop Dr, Winchester, TN 37398
0.06
$1,149,300
3
5
7,105
Off Market
326 Loop Dr, Winchester, TN 37398
0.09
$1,329,300
3
3
3,154
Off Market
326 Loop Dr #15, Winchester, TN 37398
0.09
$1,395,000
-
-
-
Off Market
160 Loop Dr, Winchester, TN 37398
0.09
$819,100
Studio
4
1,976
Off Market
Old estill spgs Rd, Winchester, TN 37398
0.11
-
-
-
-
Off Market
140 Loop Dr, Winchester, TN 37398
0.12
$693,000
3
2.5
2,100
Off Market
Old estill spgs Rd, Winchester, TN 37398
0.12
-
-
-
-
Off Market
356 Loop Dr, Winchester, TN 37398
0.13
$765,200
Studio
2
1,488
Off Market
120 Loop Dr, Winchester, TN 37398
0.14
$573,800
2
1
960
Off Market
Old estill spgs Rd, Winchester, TN 37398
0.15
-
-
-
-
Off Market
94 Loop Dr, Winchester, TN 37398
0.17
$1,017,700
5
3.5
2,844
Off Market
394 Loop Dr, Winchester, TN 37398
0.17
$642,600
Studio
2
1,300
Off Market
Old estill spgs Rd, Winchester, TN 37398
0.18
$234,400
-
-
-
Off Market
60 Loop Dr, Winchester, TN 37398
0.19
$804,800
Studio
3
1,333
Off Market
418 Loop Dr, Winchester, TN 37398
0.19
$1,261,000
3
2
1,569
Off Market
40 Loop Dr, Winchester, TN 37398
0.21
$586,700
4
2.5
2,158
Off Market
40 Loop Dr #2, Winchester, TN 37398
0.21
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 252 Loop Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1986
0.73 acre lot
1,632 sqft
$383/sqft

About this House

Enjoy open water views from this move-in ready cottage or from your spacious dock. This home is ready to be a weekend getaway or full time residence. This property has year-round water which can easily be enjoyed via the concrete driveway to the water. The home has a large room in the basement with a wood burning fireplace, perfect for chilly fall nights. This property is in close proximity to the amenities of Winchester and Tullahoma as well as only a quick boat ride to the new marina.
252 Loop Dr, Winchester, TN 37398 is a 2 bedroom, 2 bathroom, 1,632 sqft single-family home built in 1986. It last sold for $365,000 on Aug 19, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $624,600, with a rent estimate of $2,011/month.

Home Details for 252 Loop Dr

Interior Features

Interior Details
BasementWet Bar
Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: OtherFoundation Type: FootingPatio

Property Information

Year Built
Year Built: 1986Year Updated: 1986
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.73 acres

Price and Tax history

DateEventPrice
Aug 19, 2019
Source: RealTracs MLS as distributed by MLS GRID #2030025
Sold
$365,000
Apr 13, 2019
Source: Agent Provided
Listed For Sale
$385,000
Oct 31, 2018
Source: Agent Provided
ListingRemoved
$359,900
Aug 18, 2018
Source: Agent Provided
PriceChange
$359,900
Price decreased by 10%
Aug 9, 2018
Source: Agent Provided
PriceChange
$399,900
Price decreased by 7%

Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
191
6MoM

Around this home

What Locals Say about Winchester

At least 34 Trulia users voted on each feature.

  • 92 % Say yards are well-kept

  • 90 % Say car is needed

  • 85 % Say parking is easy

  • 82 % Say there's holiday spirit

  • 79 % Say it's dog friendly

  • 73 % Say it's quiet

  • 72 % Say people would walk alone at night

  • 61 % Say kids play outside

  • 59 % Say streets are well-lit

  • 54 % Say neighbors are friendly

  • 51 % Say they plan to stay for at least 5 years

  • 39 % Say there's wildlife

  • 33 % Say there are sidewalks

  • 27 % Say there are community events

  • 26 % Say it's walkable to restaurants

  • 15 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "It seems to be a very dog friendly neighborhood. I see people walking their dogs frequently. We don’t have sidewalks everywhere though."
    0
    Flag
  • Candiemae1987
    "Local shopping events, small businesses, close knit, craft sales, yard sales, trunk or treating, festivals. "
    0
    Flag
  • Ashley Leslie
    "Seasonal activities in the square or nearby. Great trick-or-treating neighborhoods. Friendly people. Tim’s Ford Lake is here! What more could you ask for. Small town vibes with everything you need close by."
    0
    Flag
  • Trulia User
    "It’s a lovely clean neighborhood with great schools! Nice parks and good roads. Perfect for families ! I love that it’s near the galleria yer feels like you’re in the countryside "
    1
    Flag
  • Trulia User
    "ppl walk dogs all the time, little traffic, courteous drivers and slow speeds, beautiful kept yards, "
    0
    Flag
  • Hnatusko.timothy
    "I’ve lived in the area for most my life and I love it...................... it’s a very pretty neighborhood"
    0
    Flag
  • Rachel.cole
    "There are a lot of retired couples in this neighborhood. It is a nice safe neighborhood. The draw back is not being able to find skilled workers who will show up when a repair needs to be done. "
    1
    Flag
  • Courtney H.
    "My neighborhood is next to Tim’s Ford State Park and Bear Trace Golf Course. The scenic beauty of Mother Nature and the vast array of wildlife during my commute make me never want to leave. "
    0
    Flag
  • Ashley Geiger
    "People are friendly and kind. I enjoy the slower pace of life here. The beauty of the outdoors are incredible. I want to raise my children here and grow old with my husband in a neighborhood like this. I love Tennessee period ."
    1
    Flag
  • Jimmydonnaanderson
    "Love Rural communities. Love living in the country . pets can run outside and grandkids can play with being told they are to loud "
    0
    Flag
  • Lindawilliamsnp
    "close to town, yet seems secluded. close to hospital. close to restaurants. city garbage pick up. city sewer/water."
    2
    Flag
  • Dannielle R.
    "It’s quite it a great community with lots to do and many small businesses that carry great local items. "
    3
    Flag
  • kell14
    "Franklin Hills Subdivision is considered one of the best places to live. Natural gas for heating/cooking/fireplace. City sewer/water/garbage and leaf pickup."
    5
    Flag
  • Michelle
    "Great quiet place to live but, yet close enough to three major cities (Huntsville, Al, Nashville, TN, Chattanooga, TN). All within an hours +/- drive."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 252 Loop Dr

  • What is 252 Loop Dr estimated to be worth?
    Trulia's estimated value for 252 Loop Dr in Winchester, TN is $624,600.
  • What is the price history for 252 Loop Dr?
    252 Loop Dr in Winchester, TN last sold for $365,000 in August 2019.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Winchester?
    Residents describe Winchester, TN as well-kept, easy to park in, and dog-friendly. Most residents say you need a car. See recently sold homes in Winchester, TN.
  • Does 252 Loop Dr have air conditioning?
    Yes, 252 Loop Dr in Winchester, TN has air conditioning.
  • Does 252 Loop Dr have laundry facilities?
    Yes, 252 Loop Dr in Winchester, TN has in-unit laundry.

Explore by feature - Pet Friendly

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Off Market Homes Near 252 Loop Dr

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