175 Overlooking Dr, Winchester, KY 40391
Property image
Property image
SOLD
MAR 27, 2026

$363,800

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,080 sqft (on 0.91 acres)

175 Overlooking Dr, Winchester, KY 40391

Est. Refi. Payment $2,240/mo*
Refinance Your Home
Currently Off Market - Sold Mar 27, 2026 for $359,000

Home Value

Trulia Estimate
$364K
Since last month
Increased$700 (+0.2%)
Since last year
Increased$58K (+18.9%)
Since last sale
Increased$5K (+1.4%)
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 +131% in the last 10 years
MonthEstimated value
2026
September 2026$364K
August 2026$363K
July 2026$362K
June 2026$362K
May 2026$361K
April 2026$361K
March 2026$359K
February 2026$359K
January 2026$187K
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
222 Ashton Oak Way, Winchester, KY
0.96
Single-Family Home
$450,000
05/26/26
3
2.5
3,444
2509 Mount Sterling Rd, Winchester, KY
0.29
Single-Family Home
$730,000
08/10/26
4
3.5
4,346
104 Teakwood Ct, Winchester, KY
1.03
Single-Family Home
$320,000
11/21/25
4
2.5
1,970
137 Eastridge Dr, Winchester, KY
1.21
Single-Family Home
$272,500
09/18/26
3
2
1,420
424 Waycross Dr, Winchester, KY
1.20
Single-Family Home
$290,000
02/04/26
4
3
1,944
225 Plantations Dr, Winchester, KY
1.07
Single-Family Home
$325,000
09/14/26
3
2.5
3,868
158 Cabin Creek Hts, Winchester, KY
1.55
Single-Family Home
$274,000
09/18/26
3
2
1,721

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
2509 Mount Sterling Rd, Winchester, KY 40391
0.29
$730,000
4
3.5
4,346
Recently Sold
1896 Mount Sterling Rd, Winchester, KY 40391
0.43
$317,800
4
2.5
1,942
Off Market
359 Silverton Way, Winchester, KY 40391
0.91
$220,000
3
2
1,502
Recently Sold
357 Silverton Way, Winchester, KY 40391
0.92
$221,000
3
2
1,502
Recently Sold
215 Ashton Oak Way, Winchester, KY 40391
0.91
$346,300
2
2
1,676
Off Market
221 Ashton Oak Way, Winchester, KY 40391
0.91
$92,300
-
-
-
Off Market
218 Ashton Oak Way, Winchester, KY 40391
0.94
$410,900
3
2
1,931
Off Market
2395 Paris Rd, Winchester, KY 40391
0.95
$14,100,000
-
-
-
For Sale
128 Bay Hill Dr, Winchester, KY 40391
0.96
$168,000
3
2
1,289
Recently Sold
214 Ashton Oak Way, Winchester, KY 40391
0.95
$77,000
-
-
-
Recently Sold
222 Ashton Oak Way, Winchester, KY 40391
0.96
$450,000
3
2.5
3,444
Recently Sold

Local Information

  • Map ViewExplore the area around 175 Overlooking Dr.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1970
0.91 acre lot
2,080 sqft
$173/sqft
Garage

About this House

What's unique:Full partially finished basementLarge recreation roomFamily roomTwo cozy fireplacesView of the lakeOversized rear deck
Relax on your front porch and enjoy the view of the lake or have a barbecue on your oversized rear deck and enjoy the countryside views. This 3-bedroom, 2-bathroom home features Living Room, Dining Room, Family Room, has two cozy fireplaces for your entertainment. Home has a full partially finished basement with a large recreation room and plenty of space to add additional rooms if needed. To compliment the home there is a garage and storage building. Home has many recent improvements and is ready to move in condition.
175 Overlooking Dr, Winchester, KY 40391 is a 3 bedroom, 2 bathroom, 2,080 sqft single-family home built in 1970. It last sold for the $359,000 asking price on Mar 27, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $363,800, with a rent estimate of $1,991/month.
Last check for updates: about 11 hours ago
Listed by V. Keith Wilson, (859) 744-4111
Coldwell Banker McMahan
Bought with: Darrell Tackett, (859) 749-2796, Dream Maker Realty, LLC
Source: Imagine MLS, MLS#26003583

Home Details for 175 Overlooking Dr

Interior Features

Interior Details
Basement: Exterior Entry,Partial,Partially Finished,Sump Pump,Walk-Out Access,Walk-Up AccessNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bathroom 1, Den, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2080 Square Feet
Appliances & Utilities
Utilities: Electricity Connected, Sewer Not Available, Water ConnectedAppliances: Dishwasher, Microwave, Refrigerator, RangeDishwasherLaundry: Electric Dryer Hookup,Washer HookupMicrowaveRefrigerator
Heating & Cooling
Heating: Electric,Heat PumpHas CoolingAir Conditioning: Central Air,Ceiling Fan(s),Heat PumpHas HeatingHeating Fuel: Electric
Fireplace & Spa
Number of Fireplaces: 2Fireplace: Basement, Family Room, Gas LogHas a Fireplace
Windows, Doors, Floors & Walls
Window: Insulated Windows, ScreensDoor: Storm Door(s)Flooring: Carpet, Laminate, Other
Levels, Entrance, & Accessibility
Levels: OneFloors: Carpet, Laminate, Other
View
Has a ViewView: Farm, Lake

Exterior Features

Exterior Home Features
Roof: Dimensional Style ShingleFencing: NoneOther Structures: Shed(s)Foundation: BlockNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 1Parking: Attached Garage,Driveway,Garage Door Opener,Off Street,Garage Faces Front
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Farm & Range
Not Allowed to Raise Horses
Finished Area
Finished Area (above surface): 1500 Square FeetFinished Area (below surface): 580 Square Feet

Property Information

Year Built
Year Built: 1970
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: HouseArchitecture: Ranch
Building
Construction Materials: Brick VeneerNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 064100000300

Price & Status

Price
List Price: $359,000Price Per Sqft: $173/sqft
Status Change & Dates
Off Market Date: Fri Feb 27 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: Closed

Location

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

Building

Building Area
Building Area: 2080 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.91 acres

Miscellaneous

BasementMls Number: 26003583Water ViewWater View: LakeAbove Grade Unfinished Area: 1500

Price and Tax history

DateEventPrice
Mar 27, 2026
Source: Imagine MLS #26003583
Sold
$359,000
Feb 27, 2026
Source: Imagine MLS #26003583
Contingent
$359,000
Feb 27, 2026
Source: Imagine MLS #26003583
Listed For Sale
$359,000
Oct 15, 2025
Source: N/A
Sold
$185,000
Apr 19, 2019
Source: Imagine MLS #1905166
Sold
$175,000

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

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Frequently asked questions about 175 Overlooking Dr

  • What is 175 Overlooking Dr estimated to be worth?
    Trulia's estimated value for 175 Overlooking Dr in Winchester, KY is $363,800.
  • What is the price history for 175 Overlooking Dr?
    175 Overlooking Dr in Winchester, KY last sold for $359,000 in March 2026.
  • 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 175 Overlooking Dr have air conditioning?
    Yes, 175 Overlooking Dr in Winchester, KY has air conditioning.
  • Does 175 Overlooking Dr have laundry facilities?
    Yes, 175 Overlooking Dr in Winchester, KY has laundry facilities.

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