321 S Maple St, Winchester, KY 40391
Property image
Property image
OFF MARKET

$277,800

Trulia Estimate
  • 6 Beds
  • 4 Baths
  • 4,490 sqft (on 0.33 acres)

321 S Maple St, Winchester, KY 40391

Est. Refi. Payment $1,724/mo*
Refinance Your Home
Currently Off Market - Sold Oct 14, 2025 for $270,000

Home Value

Trulia Estimate
$278K
Since last month
Increased$2K (+0.7%)
Since last year
Decreased$19K (-6.4%)
Since last sale
Increased$9K (+3.1%)
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 +195% in the last 10 years
MonthEstimated value
2026
September 2026$279K
August 2026$278K
July 2026$277K
June 2026$278K
May 2026$277K
April 2026$277K
March 2026$272K
February 2026$272K
January 2026$272K
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
297 S Main St, Winchester, KY
0.14
Multi-Family Home
$325,000
04/09/26
6
4
3,544
21 Beckner St, Winchester, KY
0.36
Multi-Family Home
$280,000
08/26/26
6
4
3,090
23 1/2 Wheeler St, Winchester, KY
0.32
Multi-Family Home
$347,000
01/05/26
8
4
3,706
146 W Lexington Ave, Winchester, KY
0.24
Multi-Family Home
$267,000
03/24/26
8
3
3,393
101 S Burns Avenue #1,2,3,4, Winchester, KY
0.26
Multi-Family Home
$580,000
05/29/26
8
4
5,046
217 S Highland St, Winchester, KY
0.20
Multi-Family Home
$180,000
07/02/26
4
2
2,683
149 Winn Ave, Lexington, KY
0.81
Multi-Family Home
$277,000
03/25/26
12
4
4,010
144 Holly Ave, Winchester, KY
0.89
Multi-Family Home
$260,000
06/09/26
8
5
3,637

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
16 Boone Ave, Winchester, KY 40391
0.04
$346,600
4
3
3,646
Off Market
337 S Maple St, Winchester, KY 40391
0.05
$281,400
4
2
3,184
Off Market
286 S Main St, Winchester, KY 40391
0.10
$365,100
4
2.5
3,689
Off Market
113 W Main St, Winchester, KY 40391
0.07
$423,500
Studio
-
-
Off Market
134 Boone Ave, Winchester, KY 40391
0.07
$250,300
3
2
1,878
Off Market
402 S Maple St, Winchester, KY 40391
0.09
$445,400
4
2
3,864
Off Market
252 S Highland St, Winchester, KY 40391
0.15
$252,100
3
2
1,944
Off Market
297 S Main St, Winchester, KY 40391
0.14
$325,000
6
4
3,544
Recently Sold
408 S Maple St, Winchester, KY 40391
0.11
$342,200
5
3
3,372
Off Market
254 S Highland St, Winchester, KY 40391
0.16
$249,800
4
2
3,395
Off Market
312 S Main St, Winchester, KY 40391
0.16
$295,000
3
1.5
2,355
Off Market

Local Information

  • Map ViewExplore the area around 321 S Maple St.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Multi-Family
Built in 1900
0.33 acre lot
4,490 sqft
$62/sqft
Open Parking

About this House

This investment property sits in the quiet and desirable Thomson Addition surrounded by beautiful antique homes. The lot is 1/3 of an acre and includes plenty of parking for tenants with access from the alley behind the property. Inside there are 4 units, all with private access. Three units are currently rented with tenants who plan to stay and the upper front unit is vacant and available to show anytime. The occupied units require 48 hour notice to see inside, per lease terms. Recent improvements to the property include a new roof in 2024 and 2 new furnaces. Current Monthly rent income is $2,200/month and potential to have $3000 /month with unit #1 rented. Tenants pay utilities, with separate electric and gas meters for each unit.
321 S Maple St, Winchester, KY 40391 is a 6 bedroom, 4 bathroom, 4,490 sqft multi-family built in 1900. It last sold for $270,000 on Oct 14, 2025 (3% below the $279,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $277,800, with a rent estimate of $1,446/month.
Last check for updates: about 11 hours ago
Listed by Joshua Wood, (859) 749-6293
Freedom Realty & Property Management
Bought with: Holly L Goeing, (859) 983-1656, The Agency
Source: Imagine MLS, MLS#25501988

Home Details for 321 S Maple St

Interior Features

Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 4Number of Bathrooms (full): 4
Dimensions and Layout
Living Area: 4490 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Available, Natural Gas Available, Phone Available, Sewer Available, Water AvailableLaundry: Electric Dryer Hookup,Main Level,Washer Hookup,Upper Level
Heating & Cooling
Heating: Forced AirHas CoolingAir Conditioning: Central Air,Window Unit(s)Has HeatingHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Number of Stories: 3

Exterior Features

Exterior Home Features
Roof: Shingle
Parking & Garage
No Attached GarageHas Open ParkingParking Spaces: 6Parking: Gravel,On Site,Open

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: Residential IncomeProperty Subtype: QuadruplexStructure Type: QuadruplexArchitecture: Quadruplex
Building
Not a New ConstructionAttached To Another Structure
Property Information
Parcel Number: 054104601400

Price & Status

Price
List Price: $279,000
Status Change & Dates
Off Market Date: Thu Oct 02 2025Possession Timing: Close Of Escrow

Active Status

MLS Status: Closed

Location

Direction & Address
City: WinchesterCommunity: Thomson Addition
School Information
Elementary School: ShearerJr High / Middle School: Robert CampbellHigh School: GRCHigh School District: Clark County - 7

Building

Building Area
Building Area: 4490 Square Feet

Community

Number Of Vacant Units: 1

Lot Information

Lot Area: 0.33 acres

Miscellaneous

Mls Number: 25501988

Price and Tax history

DateEventPrice
Oct 14, 2025
Source: Imagine MLS #25501988
Sold
$270,000
Oct 2, 2025
Source: Imagine MLS #25501988
Contingent
$279,000
Sep 23, 2025
Source: Imagine MLS #25501988
Listed For Sale
$279,000

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
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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
    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
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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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LGBTQ Local Legal Protections

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Frequently asked questions about 321 S Maple St

  • What is 321 S Maple St estimated to be worth?
    Trulia's estimated value for 321 S Maple St in Winchester, KY is $277,800.
  • What is the price history for 321 S Maple St?
    321 S Maple St in Winchester, KY last sold for $270,000 in October 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 321 S Maple St have air conditioning?
    Yes, 321 S Maple St in Winchester, KY has air conditioning.
  • Does 321 S Maple St have laundry facilities?
    Yes, 321 S Maple St in Winchester, KY has laundry facilities.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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