665 Bailey Ln, Winchester, KY 40391
Property image
Property image
OFF MARKET

$288,200

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,428 sqft (on 5.56 acres)

665 Bailey Ln, Winchester, KY 40391

Est. Refi. Payment $1,707/mo*
Refinance Your Home
Currently Off Market - Sold May 1, 2017 for $119,000

Home Value

Trulia Estimate
$288K
Since last month
Increased$3K (+1.2%)
Since last year
Increased$1K (+0.4%)
Since last sale
Increased$171K (+143.4%)
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 +149% in the last 10 years
MonthEstimated value
2026
August 2026$290K
July 2026$286K
June 2026$293K
May 2026$289K
April 2026$290K
March 2026$292K
February 2026$282K
January 2026$278K
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
2317 Muddy Creek Rd, Winchester, KY
0.85
Single-Family Home
$150,000
10/27/25
2
1
1,046
165 Hilltop Dr, Winchester, KY
1.32
Single-Family Home
$282,900
01/02/26
3
2
1,454
2247 Muddy Creek Rd, Winchester, KY
0.91
Single-Family Home
$111,252
06/03/26
3
1
1,145
312 Buffalo Trce, Winchester, KY
1.50
Single-Family Home
$249,900
07/28/26
3
2
1,284
407 Pueblo Ct, Winchester, KY
1.48
Single-Family Home
$242,000
06/18/26
3
2
1,244
246 Geronimo Ct, Winchester, KY
1.53
Single-Family Home
$192,565
12/22/25
3
2
1,092
305 Geronimo Ct, Winchester, KY
1.58
Single-Family Home
$210,000
09/04/25
3
2
1,150
403 Pueblo Ct, Winchester, KY
1.50
Single-Family Home
$277,500
06/30/26
3
2
1,311
322 Buffalo Trce, Winchester, KY
1.54
Single-Family Home
$205,000
10/10/25
3
2
1,110
318 Buffalo Trce, Winchester, KY
1.53
Single-Family Home
$241,500
05/01/26
3
2
1,200

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
678 Bailey Ln, Winchester, KY 40391
0.08
-
-
-
-
Off Market
520 Bailey Ln, Winchester, KY 40391
0.34
$415,800
4
3
2,400
Off Market
495 Browning 545 Ln, Winchester, KY 40391
0.71
$367,700
3
2
1,472
Off Market
2317 Muddy Creek Rd, Winchester, KY 40391
0.85
$154,100
2
1
1,046
Off Market
2925 Irvine Rd, Winchester, KY 40391
0.86
-
3
2
1,680
Off Market
2247 Muddy Creek Rd, Winchester, KY 40391
0.91
$111,252
3
1
1,145
Recently Sold
2593 Irvine Rd, Winchester, KY 40391
1.04
$225,200
3
2
1,094
Off Market
2996/3056 Irvine Rd, Winchester, KY 40391
1.04
$425,000
-
-
-
For Sale
2996 Irvine Rd, Winchester, KY 40391
1.04
$175,000
-
-
-
For Sale
3056 Irvine Rd, Winchester, KY 40391
1.05
$250,000
-
-
-
For Sale
4040 Muddy Creek Rd, Winchester, KY 40391
1.09
$759,000
4
3.5
4,584
Recently Sold
2584 Irvine Rd, Winchester, KY 40391
1.13
$165,600
2
1
990
Off Market

Local Information

  • Map ViewExplore the area around 665 Bailey Ln.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1989
Lot Size
5.56 acres
Living Area
1,428 sqft
Price/Sqft
$202

About this House

5+ Acres of beautiful property! The one story manufactured home has 3 bedrooms and 2 baths! Open concept kitchen and family room with LOTS of natural light! Includes 30x32 barn that is ideal for horses and/or a small farm. Laminate and carpet throughout. 3 storage sheds: 1 metal, 1 wood and 1 workshop with separate electric and heat. Has ONDURA Roof: ONDURA is recognized by the United States Environmental Protection Agency (EPA) as an Environmentally Preferred Product/ will not rust or corrode. See attachments for more info. Call today to see this lovely piece of country paradise! Just one country song away from downtown Winchester!
665 Bailey Ln, Winchester, KY 40391 is a 3 bedroom, 2 bathroom, 1,428 sqft single-family home built in 1989. It last sold for $119,000 on May 1, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $288,200, with a rent estimate of $1,638/month.

Home Details for 665 Bailey Ln

Interior Features

Heating & Cooling
Heating: Heat PumpHeating Fuel: Heat Pump
Interior Details
Types of Rooms: Walk In ClosetCeiling Fan
Appliances & Utilities
DishwasherMicrowaveRefrigerator
Levels, Entrance, & Accessibility
Floors: Carpet, Laminate, Linoleum Vinyl

Exterior Features

Exterior Home Features
Roof: CompositionDeckExterior: OtherPatio

Property Information

Year Built
Year Built: 1989
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 5.56 acres

Price and Tax history

DateEventPrice
May 1, 2017
Source: Imagine MLS #1613107
Sold
$119,000
Feb 6, 2017
Source: Agent Provided
Pending
$119,900
Dec 12, 2016
Source: Agent Provided
PendingToActive
$119,900
Dec 2, 2016
Source: Agent Provided
Pending
$119,900
Aug 14, 2016
Source: Agent Provided
PriceChange
$119,900
Price decreased by 4%

Market trends in Winchester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$255K
$15.67KMoM
Sale-to-List Price
98.8%
0.3%MoM
Price per sq ft
$165
$9MoM
Available listings
161
3MoM

Around this home

What Locals Say about Winchester

At least 181 Trulia users voted on each feature.

  • 89 % Say car is needed

  • 87 % Say yards are well-kept

  • 85 % Say parking is easy

  • 77 % Say it's dog friendly

  • 73 % Say kids play outside

  • 68 % Say there's holiday spirit

  • 61 % Say there are sidewalks

  • 57 % Say it's quiet

  • 53 % Say neighbors are friendly

  • 53 % Say people would walk alone at night

  • 48 % Say they plan to stay for at least 5 years

  • 44 % Say there's wildlife

  • 39 % Say streets are well-lit

  • 26 % Say it's walkable to restaurants

  • 24 % Say it's walkable to grocery stores

  • 22 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Dustin Conner
    "Rock the block events pride events Christmas parades Halloween parades beer cheese festival concerts 4th of July events free ice cream cone day"
    0
    Flag
  • Jdhurley12
    "Seems safe so far. Halloween is very popular in this neighborhood. I would recommend others to live here."
    0
    Flag
  • Kimberly Sparks
    "I was raised here. It’s always been my home and I’m trying to make it my kids home as well. I’m just trying "
    0
    Flag
  • Ccharles
    "Where I live, there are lots of space for dogs to roam and run to get their energy out. Coyotes do inhabit the area so just be mindful when your dogs are outside. "
    2
    Flag
  • Clarissa R. C.
    "Beer cheese festival is the best and The brewery is awesome. Lumas is cool too. It’s a great place to live and feel safe "
    0
    Flag
  • Joyce S.
    "Great neighborhood for walking dogs. Plenty of room to walk and areas are easy to pick up waste. Neighbors are friendly for people and pets "
    8
    Flag
  • Joyce S.
    "Great neighborhood that looks out for each other and sits on the Golf Course. Very clean, quiet neighborhood"
    5
    Flag
  • Karen K.
    "Community yard sales, lots of children and the parents watch out for each other’s children. Schools are very good. "
    2
    Flag
  • Alishacorley23
    "downtown is kind of shady but I'm from here so I know alot of people. and its cute and historic thank you."
    4
    Flag
  • Garrison9908
    "We Have a neighborhood association with a dedicated group of families that live in the area and are personally involved and educated on issues surrounding them."
    0
    Flag
  • Awallace08
    "Quiet neighborhood close to schools and shopping. Low crime area, low traffic area, properties are kept cut and clean "
    1
    Flag
  • Barb H.
    "My neighborhood is an excellent place to call home. I always see people out walking their dogs. The neighbors are friendly. "
    0
    Flag
  • Garrison9908
    "My neighborhood is a neighborhood of avid boaters and fisherman who like to live near the Kentucky River. There are a few clubs that people gather together for as well as a couple of local restaurants that are hang outs. "
    0
    Flag
  • Garrison9908
    "I’ve lived in this neighborhood for over 30 years. It is a close knit community with individuals residing here that love nature, love the Kentucky River, and all things outdoors."
    0
    Flag
  • Bridgetgwyn27
    "I travel over 25 miles a day to the next county. Can be busy especially during the 5’ o’clock hour. "
    1
    Flag
  • StephanieD
    "This is a beautiful neighborhood. On the forth of July you can sit on your deck or porch and watch the most spectacular fire work shows. It is an easy picturesque drive to Hamburg or Richmond and a quick five minute jaunt if you need a gallon of milk. Everybody I met is polite and courteous and it is very dog friendly- I once had a neighbor on another street put water out for the dogs walking by his house to drink. I wouldn't want to live anywhere else."
    1
    Flag
  • Barbara.smith13
    "There’s a pit bull that lives on east broadway that has tried to kill my dog on more than 1 occasion. I called the cops the first They did Nothing bout the attack. Put the Pitt back in his lot hooked him bk up to the car chain he was attached too!!! "
    0
    Flag
  • Barbarataulbee
    "I live here. The neighbors a great. It’s also very dog and cat friendly. Every body helps each other that lives here. They also watch out for each other. There’s never any crime in out neighborhood. "
    0
    Flag
  • Barbarataulbee
    "They would love to live here cause people watch out for each other and their doggie. Dogs are very safe in our neighborhood. "
    0
    Flag
  • Shelby G.
    "lots of street dances, 3 festivals, many community events put on by the local churches. Christmas and homecoming parades are themed, downtown does a "trick or treat on main" which is also where the street dances and beer cheese festival are."
    0
    Flag
  • Townsend m.
    "you will see dogs and their owners walking all the time in colonial park. it is a very quiet neighborhood. everyone is very nice and sweet all the kids do fundraisers for school and everyone participates."
    4
    Flag
  • Dana B.
    "Some areas are great for walking or biking but a car is needed in most areas. The traffic and commute are generally worry free. "
    0
    Flag
  • Ragan
    "Many opportunities for community involvement. Very interstate accessible so a short trip to many major cities and a lot of outdoor recreation spots. "
    0
    Flag
  • Heatherbcass
    "I have lived in my current residence for 3 years and my neighbors are like family and we all have a babysitter anytime we need one!!"
    0
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  • Cristy J.
    "very safe and friendly area, no through traffic. walk to elementary and secondary school"
    0
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LGBTQ Local Legal Protections

Frequently asked questions about 665 Bailey Ln

  • What is 665 Bailey Ln estimated to be worth?
    Trulia's estimated value for 665 Bailey Ln in Winchester, KY is $288,200.
  • What is the price history for 665 Bailey Ln?
    665 Bailey Ln in Winchester, KY last sold for $119,000 in May 2017.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $255K. That is up $15.67K from the prior month.
  • How big is the lot at 665 Bailey Ln?
    The lot at 665 Bailey Ln in Winchester, KY is about 5.6 acres.

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