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

252 Loop Dr
Winchester, TN 37398

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

$626,200

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $3,590/mo*
Refinance Your Home

$626,200

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $3,590/mo*
Refinance Your Home
2 Beds
2 Baths
1,632 sqft
(on 0.73 acres)

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

Property Type
Single-Family Home
Year Built
1986
Lot Size
0.73 acres
Living Area
1,632 sqft
Price/Sqft
$384

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. It is currently off market. The Trulia Estimate is $626,200, with a rent estimate of $1,679/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 History for 252 Loop Dr

DatePriceEventSource
08/19/2019$365,000Sold
RealTracs MLS as distributed by MLS GRID #2030025
04/13/2019$385,000Listed For SaleAgent Provided
10/31/2018$359,900ListingRemovedAgent Provided
08/18/2018$359,900PriceChange
Agent Provided
08/09/2018$399,900PriceChange
Agent Provided
07/27/2018$429,900Listed For SaleAgent Provided
08/25/2014$274,900Sold
N/A
02/27/2014$299,000Listed For SaleAgent Provided

Market trends in Winchester

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$375K
$61.67KMoM
Sale-to-List Price
97.5%
0.1%MoM
Price per sq ft
$192
$11MoM
Available listings
195
3MoM
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Property Tax and Assessment

Year2025
Tax$1,930
Assessment$386,900
Home facts updated by county records

Comparable Sales for 252 Loop Dr

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
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
2245 Old Estill Springs Rd, Winchester, TN
0.74
Single-Family Home
$155,000
06/29/26
4
1
1,732
197 Murray Lake Dr, Winchester, TN
1.16
Single-Family Home
$439,900
12/02/25
3
3
2,528
235 Lakeview St, Estill Springs, TN
1.44
Single-Family Home
$285,000
10/30/25
3
2
1,700

Nearby homes

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Assigned Schools

These are the assigned schools for 252 Loop Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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Apartments for Rent

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Explore by feature - Pet Friendly

6 pet-friendly rentals in Winchester, TN

Explore by feature - Air Conditioning

7 rentals with air conditioning in Winchester, TN

Explore by feature - Washer/dryer

10 rentals with a washer/dryer in Winchester, TN

Homes for sale near 252 Loop Dr

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Off Market Homes Near 252 Loop Dr

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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 $626,200.
  • 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's the median sale price in Winchester?
    The median sale price in Winchester is $375K. That is up $61.67K from the prior month.
  • 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.