Pending

$299,900

8 Monroe Ave, Winchester, KY 40391

3beds

1,444sqft

$2,039/mo

Get pre-qualified

Single Family Residence

Built in 1999

6,534 Square Feet Lot

$292,300 Zestimate^®

$208/sqft

$-- HOA

What's special

New roofBathroom features bluetooth connectivityLarge fenced backyardBeautifully landscaped yard

Welcome to one of Winchester's best-kept secrets! This beautifully updated 3-bedroom home is truly move-in ready and packed with upgrades inside and out. From the moment you arrive, the beautifully landscaped yard sets the tone for what's waiting inside. Thoughtful updates throughout give the home a fresh, modern feel, while a new roof provides added peace of mind. Step outside and enjoy the large fenced backyard, offering plenty of room for entertaining, pets, play, or relaxing in your own private outdoor space. And it's the little extras that make this home stand out—even the bathroom features Bluetooth connectivity for an added touch of modern convenience! With upgrades around every corner and all the work already done, this is the kind of home you can simply move into and enjoy. Stylish, updated, and full of unexpected extras—this Winchester gem may not stay a secret for long!

15 days
566
51

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 3
Bathrooms: 2
Full bathrooms: 2

Primary bedroom

Level: First

Bedroom 2

Level: First

Bedroom 3

Level: First

Bathroom 1

Level: First

Bathroom 2

Level: First

Dining room

Level: First

Kitchen

Level: First

Utility room

Level: First

Heating

Heat Pump

Cooling

Heat Pump

Appliances

Included: Dishwasher, Microwave, Refrigerator, Range
Laundry: Electric Dryer Hookup, Washer Hookup

Features

Walk-In Closet(s), Ceiling Fan(s)
Flooring: Ceramic Tile
Doors: Storm Door(s)
Windows: Blinds, Screens
Basement: Crawl Space
Number of fireplaces: 1
Fireplace features: Living Room

Interior area

Total structure area: 1,444
Total interior livable area: 1,444 sqft
Finished area above ground: 1,444
Finished area below ground: 0

Property

Parking

Parking features: Driveway, Off Street
Has uncovered spaces: Yes

Features

Levels: One
Exterior features: Fire Pit
Fencing: Privacy

Lot

Size: 6,534 Square Feet
Features: Landscaped

Details

Additional structures: Shed(s)
Parcel number: 054100601301

Construction

Type & style

Home type: SingleFamily
Property subtype: Single Family Residence

Materials

Vinyl Siding
Foundation: Block
Roof: Dimensional Style

Condition

Year built: 1999

Utilities & green energy

Sewer: Public Sewer
Water: Public
Utilities for property: Cable Available, Electricity Connected, Sewer Connected, Water Connected

Community & HOA

HOA

Has HOA: No

Location

Region: Winchester

Financial & listing details

Price per square foot: $208/sqft
Tax assessed value: $108,300
Annual tax amount: $1,041
Date on market: 10/1/2026

Estimated market value

$292,300

$278,000 - $307,000

$1,615/mo

Price history

Date	Event	Price
10/13/2026	Pending sale	$299,900$208/sqft
Source: Imagine MLS #26027106 Report a problem
10/1/2026	Listed for sale	$299,900-6.3%$208/sqft
Source: Imagine MLS #26027106 Report a problem
9/17/2026	Listing removed	$319,900$222/sqft
Source: Imagine MLS #26014053 Report a problem
8/3/2026	Price change	$319,900-1.5%$222/sqft
Source: Imagine MLS #26014053 Report a problem
7/14/2026	Price change	$324,900-1.5%$225/sqft
Source: Imagine MLS #26014053 Report a problem
6/23/2026	Price change	$329,900-2.9%$228/sqft
Source: Imagine MLS #26014053 Report a problem
6/17/2026	Listed for sale	$339,900+1410.7%$235/sqft
Source: Imagine MLS #26014053 Report a problem
3/28/1991	Sold	$22,500$16/sqft
Source: Agent Provided Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$1,041 -3.9%	$108,300
2024	$1,083 +1.5%	$108,300
2023	$1,067	$108,300
2022	$1,067 +0.3%	$108,300
2021	$1,064 +56.7%	$108,300
2020	$679 +574.1%	$108,300
2019	$101	$108,300
2018	$101 -2.4%	$108,300
2017	$103 -1%	$108,300
2016	$104	$108,300
2015	$104 -1.3%	$108,300 +49.8%
2013	$106	$72,300 -30.3%
2011	--	$103,800
2010	--	$103,800