414 Pine Bluff Rd, Winchester, TN 37398
Property image
Property image
OFF MARKET

414 Pine Bluff Rd
Winchester, TN 37398

  • 3 Beds
  • 2 Baths
  • 1,408 sqft (on 3.52 acres)

$495,500

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $2,835/mo*
Refinance Your Home

$495,500

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $2,835/mo*
Refinance Your Home
3 Beds
2 Baths
1,408 sqft
(on 3.52 acres)

Home Value

Trulia Estimate
$496K
Since last month
Decreased$10K (-2%)
Since last year
Increased$7K (+1.3%)
Since last sale
Increased$271K (+120.4%)
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 +190% in the last 10 years
MonthEstimated value
2026
August 2026$496K
July 2026$506K
June 2026$501K
May 2026$484K
April 2026$484K
March 2026$480K
February 2026$471K
January 2026$450K
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
224 Pine Bluff Rd, Winchester, TN
0.23
Single-Family Home
$400,000
09/05/25
4
2.5
2,307
4137 Eastbrook Rd, Estill Springs, TN
0.78
Single-Family Home
$231,000
02/09/26
3
2
1,680
112 Pine Bluff Ct #14C, Winchester, TN
0.27
Single-Family Home
$575,000
07/20/26
3
3
2,500
74 Pine Bluff Rd, Winchester, TN
0.37
Single-Family Home
$462,500
07/30/26
3
2.5
2,308
90 Pine Bluff Rd, Winchester, TN
0.35
Single-Family Home
$476,000
06/24/26
3
2.5
2,773
3926 Old Tullahoma Rd, Winchester, TN
1.00
Single-Family Home
$210,000
06/05/26
3
2
1,300
91 Sunset Vw, Estill Springs, TN
0.80
Single-Family Home
$285,000
10/06/25
2
2.5
1,469
130 Phillips Dr, Winchester, TN
0.23
Single-Family Home
$1,450,000
10/24/25
3
4.5
4,193
55 Grider Rd, Winchester, TN
1.13
Single-Family Home
$295,000
12/18/25
3
2
1,404
111 Grider Rd, Winchester, TN
1.13
Single-Family Home
$235,000
07/02/26
3
2
1,825

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
49 W Paradise Dr #49, Winchester, TN 37398
0.09
-
-
-
-
Off Market
331 Pine Bluff Rd, Winchester, TN 37398
0.10
$367,000
4
2
1,500
Off Market
105 W Paradise Dr, Winchester, TN 37398
0.13
$799,900
4
3.5
4,100
For Sale
85 Phillips Dr, Winchester, TN 37398
0.17
$626,700
3
2
2,125
Off Market
242 Pine Bluff Rd, Winchester, TN 37398
0.21
$461,600
3
2.5
2,417
Off Market
224 Pine Bluff Rd, Winchester, TN 37398
0.23
$394,700
4
2.5
2,307
Off Market
130 Phillips Dr, Winchester, TN 37398
0.23
$1,450,000
3
4.5
4,193
Recently Sold
178 Pine Bluff Rd #10, Winchester, TN 37398
0.25
$492,800
3
2.5
2,536
Off Market
112 Pine Bluff Ct #14C, Winchester, TN 37398
0.27
$575,000
3
3
2,500
Recently Sold
90 Pine Bluff Ct #14B, Winchester, TN 37398
0.29
$644,900
3
2.5
2,729
For Sale
231 Phillips Dr, Winchester, TN 37398
0.30
$650,600
5
4
2,112
Off Market
90 Pine Bluff Rd, Winchester, TN 37398
0.35
$476,000
3
2.5
2,773
Recently Sold

Local Information

  • Map ViewExplore the area around 414 Pine Bluff Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1966
Lot Size
3.52 acres
Living Area
1,408 sqft
Price/Sqft
$352
Parking
Garage

About this House

Updated 3 bedroom, 2 bath home near Tims Ford Lake. Four boat ramps within a few miles. Aprx. 3.52 acres, 48x30 metal shop w/two 10 ft. roll up doors, detached garage/workshop, carports & single car attached garage w/finishable living area. Hardwood floors & tile, screened porch at rear of home. HVAC & new ductwork-2017.Tankless water heater. Convenient to Winchester & Tullahoma.
414 Pine Bluff Rd, Winchester, TN 37398 is a 3 bedroom, 2 bathroom, 1,408 sqft single-family home built in 1966. It last sold for $225,000 on Feb 2, 2021. It is currently off market. The Trulia Estimate is $495,500, with a rent estimate of $1,737/month.

Home Details for 414 Pine Bluff Rd

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood
Interior Details
Types of Rooms: Dining Room
Appliances & Utilities
DryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionExterior: BrickFoundation Type: Footing
Parking & Garage
GarageParking Spaces: 5Parking: Garage Attached, Garage Detached

Property Information

Year Built
Year Built: 1966Year Updated: 1978
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 3.52 acres

Price and Tax history

DateEventPrice
Feb 2, 2021
Source: RealTracs MLS as distributed by MLS GRID #2209910
Sold
$225,000
Jan 13, 2021
Source: RealTracs MLS as distributed by MLS GRID #2209910
Pending
$229,900
Dec 16, 2020
Source: N/A
Sold
$75,000
Nov 28, 2020
Source: Agent Provided
Listed For Sale
$229,900
May 7, 2018
Source: N/A
Sold
$197,500

Market trends in Winchester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
196
1MoM

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 414 Pine Bluff Rd

  • What is 414 Pine Bluff Rd estimated to be worth?
    Trulia's estimated value for 414 Pine Bluff Rd in Winchester, TN is $495,500.
  • What is the price history for 414 Pine Bluff Rd?
    414 Pine Bluff Rd in Winchester, TN last sold for $225,000 in February 2021.
  • 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 414 Pine Bluff Rd have air conditioning?
    Yes, 414 Pine Bluff Rd in Winchester, TN has air conditioning.
  • Does 414 Pine Bluff Rd have laundry facilities?
    Yes, 414 Pine Bluff Rd in Winchester, TN has in-unit laundry.

Explore by feature - Pet Friendly

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Explore by feature - Washer/dryer

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