Pending

$285,000

108 Milwood Dr, Winchester, KY 40391

3beds

1,955sqft

$1,803/mo

Get pre-qualified

Single Family Residence

Built in 1965

10,454 Square Feet Lot

$283,500 Zestimate^®

$146/sqft

$-- HOA

What's special

Gas log fireplacePeaceful backyard settingWooded viewsFunctional floor planCozy denFenced backyard

Welcome to 108 Milwood Drive\! Nestled in one of Winchester's most desirable neighborhoods, this well\-maintained 3\-bedroom, 2\-bath ranch offers a functional floor plan and peaceful backyard setting\. The spacious living room features a gas log fireplace, while the primary suite includes a private en suite bath\. A cozy den opens to a wooden deck overlooking the fenced backyard and wooded views—perfect for relaxing or entertaining\. The semi\-finished walkout basement provides additional living space and a rear\-entry garage for added convenience\. Don't miss this opportunity to own a home that combines comfort, privacy, and a great location\!

25 days

1,281

73

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 3
Bathrooms: 2
Full bathrooms: 2

Primary bedroom

Level: First

Bedroom 2

Level: First

Bathroom 1

Level: First

Bathroom 2

Level: First

Bathroom 3

Level: First

Bonus room

Level: Lower

Den

Level: First

Kitchen

Level: First

Living room

Level: First

Utility room

Level: Lower

Heating

Forced Air, Natural Gas

Cooling

Attic Fan, Central Air, Heat Pump

Appliances

Included: Disposal, Dishwasher, Refrigerator, Range
Laundry: Electric Dryer Hookup, Washer Hookup, Lower Level

Features

Flooring: Carpet, Concrete, Hardwood, Tile, Vinyl
Doors: Storm Door(s)
Windows: Insulated Windows, Blinds
Basement: Concrete,Exterior Entry,Full,Interior Entry,Partially Finished,Walk-Out Access,Walk-Up Access
Number of fireplaces: 1
Fireplace features: Gas Log, Living Room

Interior area

Total structure area: 1,955
Total interior livable area: 1,955 sqft
Finished area above ground: 1,496
Finished area below ground: 459

Property

Parking

Total spaces: 1
Parking features: Attached Garage, Basement, Driveway, Garage Door Opener, Off Street, Garage Faces Rear
Garage spaces: 1
Has uncovered spaces: Yes

Features

Levels: One
Fencing: Chain Link
Has view: Yes
View description: Trees/Woods, Other

Lot

Size: 10,454 Square Feet
Features: Landscaped, Few Trees

Details

Additional structures: Workshop
Parcel number: 054200100500

Construction

Type & style

Home type: SingleFamily
Architectural style: Ranch
Property subtype: Single Family Residence

Materials

Brick Veneer
Foundation: Block
Roof: Composition

Condition

Year built: 1965

Utilities & green energy

Sewer: Public Sewer
Water: Public
Utilities for property: Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected

Community & HOA

Community

Subdivision: Milwood

HOA

Has HOA: No

Location

Region: Winchester

Financial & listing details

Price per square foot: $146/sqft
Tax assessed value: $159,600
Annual tax amount: $1,133
Date on market: 7/26/2026

Estimated market value

$283,500

$269,000 - $298,000

$1,689/mo

Price history

Date	Event	Price
7/28/2026	Pending sale	$285,000$146/sqft
Source: Imagine MLS #26019908 Report a problem
7/26/2026	Listed for sale	$285,000+96.6%$146/sqft
Source: Imagine MLS #26019908 Report a problem
9/21/2006	Sold	$145,000$74/sqft
Source: Imagine MLS #632134 Report a problem

Public tax history

Year	Property taxes	Tax assessment
2024	$1,133 -3.5%	$159,600
2023	$1,173	$159,600
2022	$1,173 +0.3%	$159,600
2021	$1,170 -1.2%	$159,600
2020	$1,184 +574.1%	$159,600
2019	$176	$159,600
2018	$176 -1.4%	$159,600
2017	$178 -0.6%	$159,600
2016	$179	$159,600
2015	$179 -0.7%	$159,600
2013	$180	$159,600
2011	--	$159,600
2010	--	$159,600