29 Hampton Ave, Winchester, KY 40391
Property image
Property image
SOLD
DEC 1, 2025

$386,400

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,820 sqft (on 0.29 acres)

29 Hampton Ave, Winchester, KY 40391

Est. Refi. Payment $2,385/mo*
Refinance Your Home
Currently Off Market - Sold Dec 1, 2025 for $385,000

Home Value

Trulia Estimate
$386K
Since last month
Decreased$6K (-1.6%)
Since last year
Increased$84K (+27.8%)
Since last sale
Increased$1K (+0.4%)
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 +142% in the last 10 years
MonthEstimated value
2026
September 2026$386K
August 2026$382K
July 2026$393K
June 2026$394K
May 2026$393K
April 2026$393K
March 2026$387K
February 2026$387K
January 2026$387K
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
27 Hampton Ave, Winchester, KY
0.02
Single-Family Home
$340,000
08/14/26
3
2
2,835
19 Snowfall Dr, Winchester, KY
0.25
Single-Family Home
$390,000
10/21/25
3
2
1,625
108 Milwood Dr, Winchester, KY
0.25
Single-Family Home
$255,580
09/02/26
3
2
1,955
103 Hampton Ave, Winchester, KY
0.08
Single-Family Home
$257,400
11/21/25
3
2.5
1,715
35 Mockingbird Valley Rd, Winchester, KY
0.20
Single-Family Home
$330,000
11/21/25
3
2.5
1,735
219 Hampton Ave, Winchester, KY
0.12
Single-Family Home
$340,000
10/10/25
4
2.5
2,929
213 Hood Ave, Winchester, KY
0.15
Single-Family Home
$354,000
12/19/25
4
2.5
2,244
118 Windridge Dr, Winchester, KY
0.42
Single-Family Home
$307,900
05/29/26
3
2
1,617
8 Village Dr, Winchester, KY
0.51
Single-Family Home
$285,000
01/26/26
3
2
1,979

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
27 Hampton Ave, Winchester, KY 40391
0.02
$340,000
3
2
2,835
Recently Sold
33 Hampton Ave, Winchester, KY 40391
0.04
$408,000
4
3
3,580
Off Market
118 Southern Ct, Winchester, KY 40391
0.07
$236,700
4
1.5
1,598
Off Market
17 Hampton Ave, Winchester, KY 40391
0.09
$444,000
4
2
3,181
Off Market
103 Hampton Ave, Winchester, KY 40391
0.08
$257,400
3
2.5
1,715
Recently Sold
115 Hampton Ave, Winchester, KY 40391
0.10
$322,200
4
2.5
3,042
Off Market
14 Western Ave, Winchester, KY 40391
0.13
$355,500
3
2
1,676
Off Market
511 Boone Ave, Winchester, KY 40391
0.13
$904,000
4
4.5
4,698
Off Market
213 Hood Ave, Winchester, KY 40391
0.15
$354,000
4
2.5
2,244
Recently Sold
121 Hampton Ave, Winchester, KY 40391
0.12
$346,600
3
2
2,248
Off Market
117 Southern Ct, Winchester, KY 40391
0.15
$250,000
3
1
1,175
Off Market
219 Hampton Ave, Winchester, KY 40391
0.12
$350,000
4
2.5
2,929
Off Market

Local Information

  • Map ViewExplore the area around 29 Hampton Ave.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1950
0.29 acre lot
1,820 sqft
$212/sqft
Garage

About this House

Classic brick story and half home with large open remodeled kitchen which leads to deck and secluded privacy fenced back yard. Hardwood throughout, updated tile baths, masonry FP's with remote gas logs plus an inviting glassed seasonal sun room. Large usable basement den merely needs ceiling completed. Newer tilt-in windows and all plumbing within home is now PVC and has a water filtering system. Walk to town, library or Country Club but return to the quiet privacy of this lovely mature tree shaded cul de sac. Minutes to I64, 75 and 18 minutes to Hamburg. Ask to see Addendum of current owners further updates. *Basement hanging mantel does not convey. Make an appointment to see this LOCATION very soon.
29 Hampton Ave, Winchester, KY 40391 is a 3 bedroom, 2 bathroom, 1,820 sqft single-family home built in 1950. It last sold for $385,000 on Dec 1, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $386,400, with a rent estimate of $1,715/month.

Home Details for 29 Hampton Ave

Interior Features

Interior Details
BasementNumber of Rooms: 10Types of Rooms: Walk In Closet, Dining Room, Family Room, Pantry, Sun RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1.5Floors: Tile, Hardwood
Appliances & Utilities
DishwasherDisposalRefrigerator
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: CompositionDeckExterior: Vinyl, BrickFoundation Type: Concrete BlockPatio
Parking & Garage
GarageParking Spaces: 3Parking: Garage Detached

Property Information

Year Built
Year Built: 1950
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Price & Status

Price
Price Per Sqft: $212/sqft

Lot Information

Lot Area: 0.29 acres

Price and Tax history

DateEventPrice
Dec 1, 2025
Source: N/A
Sold
$385,000
Jul 10, 2025
Source: N/A
PriceChange
$420,000
Price decreased by 3%
May 26, 2025
Source: N/A
Listed For Sale
$435,000
May 15, 2017
Source: Imagine MLS #1706745
Sold
$167,000
Apr 3, 2017
Source: Agent Provided
Pending
$172,000

Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$269K
$14.3KMoM
Sale-to-List Price
99.3%
0.5%MoM
Price per sq ft
$164
$0MoM
Available listings
157
5MoM

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
    Flag
  • Cristy J.
    "very safe and friendly area, no through traffic. walk to elementary and secondary school"
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 29 Hampton Ave

  • What is 29 Hampton Ave estimated to be worth?
    Trulia's estimated value for 29 Hampton Ave in Winchester, KY is $386,400.
  • What is the price history for 29 Hampton Ave?
    29 Hampton Ave in Winchester, KY last sold for $385,000 in December 2025.
  • 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 $269K. That is up $14.3K from the prior month.
  • Does 29 Hampton Ave have air conditioning?
    Yes, 29 Hampton Ave in Winchester, KY has air conditioning.
  • How big is the lot at 29 Hampton Ave?
    The lot at 29 Hampton Ave in Winchester, KY is about 0.29 acres (12,797 sq ft).

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