108 Caudill Dr, Winchester, KY 40391
OFF MARKET

108 Caudill Dr
Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,176 sqft (on 0.87 acres)

$271,300

Trulia Estimate
as of May 6, 2026
Est. Refi. Payment $1,593/mo*
Refinance Your Home

$271,300

Trulia Estimate
as of May 6, 2026
Est. Refi. Payment $1,593/mo*
Refinance Your Home
3 Beds
1 Bath
1,176 sqft
(on 0.87 acres)

Homes for sale near 108 Caudill Dr

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Apartments for Rent

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Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

This single-family home is located at 108 Caudill Dr, Winchester, KY. 108 Caudill Dr is in Winchester, KY and in ZIP code 40391. This property has 3 bedrooms, 1 bathroom and approximately 1,176 sqft of floor space. This property has a lot size of 0.87 acres.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 108 Caudill Dr

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionExterior: OtherFoundation Type: Concrete Block
Pool
Pool
Parking & Garage
GarageParking: Garage Attached, Off Street

Property Information

Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 0.87 acres

Price History for 108 Caudill Dr

DatePriceEventSource
03/31/1997$78,500Sold
Imagine MLS #702492
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Property Tax and Assessment

Year2024
Tax$1,107
Assessment$157,000
Home facts updated by county records

Comparable Sales for 108 Caudill Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
517 Hidden Hills Way, Winchester, KY
0.63
Single-Family Home
$183,000
07/30/25
3
2
1,120
33 Bon Haven Ave, Winchester, KY
1.04
Single-Family Home
$100,000
09/24/25
2
1
1,386
205 Arbor Ct, Winchester, KY
0.64
Single-Family Home
$186,000
05/14/25
3
2
1,188
55 Judy Ann Ct, Winchester, KY
0.74
Single-Family Home
$143,000
06/12/25
3
1.5
1,220
205 Beaumont Pl, Winchester, KY
0.68
Single-Family Home
$272,000
06/26/25
3
2
1,404
507 Hidden Hills Way, Winchester, KY
0.67
Single-Family Home
$190,000
07/15/25
3
2
1,120
514 Hidden Hills Way, Winchester, KY
0.66
Single-Family Home
$225,200
04/28/26
3
2
1,120
23 Meadowbrook Dr, Winchester, KY
0.71
Single-Family Home
$180,000
07/01/25
4
3
2,250
114 Bayberry Ln, Winchester, KY
0.72
Single-Family Home
$249,900
07/21/25
3
2
1,644
509 Hidden Hills Way, Winchester, KY
0.66
Single-Family Home
$214,000
05/19/25
3
2
1,402

Assigned Schools

These are the assigned schools for 108 Caudill 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 181 Trulia users voted on each feature.

  • 89 % Say car is needed

  • 87 % Say yards are well-kept

  • 85 % Say parking is easy

  • 78 % 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

Learn more about our methodology.
  • Jdhurley12
    "Seems safe so far. Halloween is very popular in this neighborhood. I would recommend others to live here."
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  • 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
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  • 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
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  • 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."
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  • 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. "
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  • 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. "
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  • 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."
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  • Bridgetgwyn27
    "I travel over 25 miles a day to the next county. Can be busy especially during the 5’ o’clock hour. "
    1
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  • 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."
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  • 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
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  • 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
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  • Barbarataulbee
    "They would love to live here cause people watch out for each other and their doggie. Dogs are very safe in our neighborhood. "
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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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Homes for rent near 108 Caudill Dr

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Off Market Homes Near 108 Caudill Dr

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Explore by feature

108 Caudill Dr, Winchester, KY 40391 is a 3 bedroom, 1 bathroom, 1,176 sqft single-family home. This property is not currently available for sale. 108 Caudill Dr was last sold on Mar 31, 1997 for $78,500. The current Trulia Estimate for 108 Caudill Dr is $271,300.