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

175 Overlooking Dr
Winchester, KY 40391

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

$359,000

Last Sold: Mar 27, 2026
$173/sqft

$359,000

Last Sold: Mar 27, 2026
$173/sqft
3 Beds
2 Baths
2,080 sqft
(on 0.91 acres)

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

Property Type
Single-Family Home
Year Built
1970
Lot Size
0.91 acres
Living Area
2,080 sqft
Price/Sqft
$173/sqft
Parking
Garage

About this House

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. It is currently off market. The Trulia Estimate is $362,300, with a rent estimate of $1,907/month.

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
Last check for updates: about 20 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

Price History for 175 Overlooking Dr

DatePriceEventSource
03/27/2026$359,000Sold
Imagine MLS #26003583
02/27/2026$359,000ContingentImagine MLS #26003583
02/27/2026$359,000Listed For SaleImagine MLS #26003583
10/15/2025$185,000Sold
N/A
04/19/2019$175,000Sold
Imagine MLS #1905166
03/18/2019$179,900PendingAgent Provided
03/15/2019$179,900Listed For SaleAgent Provided
06/24/2018$171,000Sold
N/A
05/19/2018$169,900PendingAgent Provided
05/11/2018$169,900Listed For SaleAgent Provided
02/17/1999$127,500Sold
Imagine MLS #9810619

Market trends in Winchester

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$239K
$7.67KMoM
Sale-to-List Price
99.1%
0.4%MoM
Price per sq ft
$156
$2MoM
Available listings
163
10MoM
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Property Tax and Assessment

Year2024
Tax$1,750
Assessment$175,000
Home facts updated by county records

Comparable Sales for 175 Overlooking Dr

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
208 Royal Oak Dr, Winchester, KY
1.06
Single-Family Home
$472,500
09/09/25
4
2.5
2,593
104 Teakwood Ct, Winchester, KY
1.03
Single-Family Home
$320,000
11/21/25
4
2.5
1,970
424 Waycross Dr, Winchester, KY
1.20
Single-Family Home
$290,000
02/04/26
4
3
1,944
115 Watercrest Cir, Winchester, KY
1.30
Single-Family Home
$243,500
07/16/26
4
3
2,112
274 Greenway Dr, Winchester, KY
1.79
Single-Family Home
$356,000
07/10/26
4
2
2,208
47 Watts Rd, Winchester, KY
1.50
Single-Family Home
$200,000
03/04/26
3
2
1,893
222 Bracken Ct, Winchester, KY
1.35
Single-Family Home
$263,500
04/10/26
3
2.5
1,456

Nearby homes

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Assigned Schools

These are the assigned schools for 175 Overlooking 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

  • 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
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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
    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
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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."
    0
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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
    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
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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
    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
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18 pet-friendly rentals in Winchester, KY

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Homes for sale near 175 Overlooking Dr

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Off Market Homes Near 175 Overlooking Dr

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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.