5000 Winchester Rd, Lexington, KY 40509
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OFF MARKET

5000 Winchester Rd
Lexington, KY 40509

  • 6 Beds
  • 5 Baths
  • 9,958 sqft (on 40 acres)

$1,787,200

Trulia Estimate
as of Aug 12, 2026
Est. Refi. Payment $10,420/mo*
Refinance Your Home

$1,787,200

Trulia Estimate
as of Aug 12, 2026
Est. Refi. Payment $10,420/mo*
Refinance Your Home
6 Beds
5 Baths
9,958 sqft
(on 40 acres)

Home Value

Trulia Estimate
$1.79M
Since last month
Decreased$110K (-5.8%)
Since last year
Decreased$35K (-1.9%)
Since last sale
Increased$292K (+19.5%)
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 +20% in the last 10 years
MonthEstimated value
2026
August 2026$1.79M
July 2026$1.84M
June 2026$1.9M
May 2026$1.82M
April 2026$1.87M
March 2026$1.87M
February 2026$1.8M
January 2026$1.81M
2025
2023

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
3274 N Cleveland Rd, Lexington, KY
1.10
Single-Family Home
$2,325,000
01/20/26
5
5
8,041
4027 Whitemark Ct, Lexington, KY
0.52
Single-Family Home
$499,000
07/27/26
4
3
2,940
4042 Longford Ct, Lexington, KY
0.57
Single-Family Home
$432,000
04/17/26
3
1.5
1,796
5654 Winchester Rd, Lexington, KY
1.10
Single-Family Home
$465,000
02/09/26
3
3
1,965
5666 Winchester Rd, Lexington, KY
1.12
Single-Family Home
$335,000
04/10/26
4
2
1,687
1788 Bahama Rd, Lexington, KY
2.34
Single-Family Home
$1,299,900
07/01/26
6
5
7,580
1813 Bahama Rd, Lexington, KY
2.22
Single-Family Home
$1,250,000
07/31/26
5
5
6,811
4039 Royster Rd, Lexington, KY
1.31
Single-Family Home
$350,000
03/24/26
4
2
1,798

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
4861 Winchester Rd, Lexington, KY 40509
0.23
$575,000
3
2
3,500
For Sale
3290 Haley Rd, Lexington, KY 40516
0.24
$327,500
3
2
1,440
Off Market
3260 Haley Rd, Lexington, KY 40516
0.26
$712,200
4
3
3,390
Off Market
2591 Eastpoint Dr, Lexington, KY 40516
0.45
$498,300
4
2.5
2,746
Off Market
4027 Whitemark Ct, Lexington, KY 40516
0.52
$499,000
4
3
2,940
Recently Sold
4042 Longford Ct, Lexington, KY 40516
0.57
$432,000
3
1.5
1,796
Recently Sold
4042 Whitemark Ct, Lexington, KY 40516
0.59
$575,000
3
2.5
2,930
For Sale
5388 Winchester Rd, Lexington, KY 40509
0.62
-
-
-
-
Off Market
5562 Winchester Rd, Lexington, KY 40509
0.91
-
-
-
-
Off Market
244 La Somme Dr, Lexington, KY 40509
0.94
$392,900
3
2.5
2,010
Off Market
5654 Winchester Rd, Lexington, KY 40509
1.10
$465,000
3
3
1,965
Recently Sold

Local Information

  • Map ViewExplore the area around 5000 Winchester Rd.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1938
Lot Size
40 acres
Living Area
9,958 sqft
Price/Sqft
$179
Parking
Garage

About this House

This is a one-of-a-kind home and property. Nicknamed The Fortress at 5000 due to the unbelievably sturdy, concrete construction of the main residence, this property is a very special offering.

Situated on 40+- acres of the most beautiful land in Kentucky you will find this 6-bedroom 5 bath mansion, it is as beautiful as it is unique. Built in 1938, using nearly all concrete construction for the infrastructure, the residence was built for strength, durability, and elegance.

The large formal Dining Room, Parlor, Study, Entry Foyer, and Family Dining Room are all graced by 12-foot ceilings with intricate plaster medallions...with rugs to match the medallion designs. The fireplaces on the first floor are surrounded by French-style marble mantles rescued from the demolition of the former Green Hills Mansion of Elmendorf Farm.

On the second floor, after ascending the gorgeous circular staircase, you will find 6 large ensuite bedrooms with 10 ft ceilings, a true rarity for the construction period of the residence. Located just behind the well-landscaped yard is a genuine brick Hemp Barn (50x100). The home consists of over 9,928 Sq, ft. and is awaiting its new owner's updating.
5000 Winchester Rd, Lexington, KY 40509 is a 6 bedroom, 5 bathroom, 9,958 sqft single-family home built in 1938. It last sold for the $1,495,000 asking price on Aug 25, 2023. It is currently off market. The Trulia Estimate is $1,787,200, with a rent estimate of $4,788/month.

Home Details for 5000 Winchester Rd

Interior Features

Interior Details
Number of Rooms: 3Types of Rooms: Den, Dining Room, Family Room
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 5Number of Bathrooms (full): 5
Dimensions and Layout
Living Area: 9958 Square Feet
Appliances & Utilities
Utilities: Electricity Connected, Natural Gas Connected, Water Connected
Heating & Cooling
Heating: Hot WaterHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Has a Fireplace
Windows, Doors, Floors & Walls
Flooring: Hardwood
Levels, Entrance, & Accessibility
Levels: TwoFloors: Hardwood
View
Has a ViewView: Farm

Exterior Features

Exterior Home Features
Fencing: WireOther Structures: Workshop
Parking & Garage
Has a GarageParking: Garage
Water & Sewer
Sewer: Septic Tank
Surface & Elevation
Topography: Gentle Sloping, Level
Finished Area
Finished Area (above surface): 9958 Square Feet

Property Information

Year Built
Year Built: 1938
Property Type / Style
Property Type: FarmProperty Subtype: FarmStructure Type: HouseArchitecture: Colonial
Building
Not a New Construction
Property Information
Usage of Home: Cattle, Horses, Pasture, ResidentialParcel Number: 20046300

Price & Status

Price
List Price: $1,495,000
Status Change & Dates
Off Market Date: Fri Jun 30 2023

Active Status

MLS Status: Closed

Location

Direction & Address
City: LexingtonCommunity: Rural
School Information
Elementary School: Dixie MagnetJr High / Middle School: CrawfordHigh School: Frederick DouglassHigh School District: Fayette County - 1

Building

Building Area
Building Area: 9958 Square Feet

Lot Information

Lot Area: 40 Acres

Miscellaneous

BasementMls Number: 23011787Above Grade Unfinished Area: 9958
Last check for updates: about 11 hours ago
Listed by John Scott Durbin, (859) 421-9453
Bluegrass Sotheby's International Realty
Bought with: Casey R Weesner, (859) 621-4222, Weesner Properties, Inc.
Source: Imagine MLS, MLS#23011787

Price and Tax history

DateEventPrice
Aug 25, 2023
Source: Imagine MLS #23011787
Sold
$1,495,000
Jul 13, 2023
Source: Imagine MLS #23011787
Pending
$1,495,000
Jun 30, 2023
Source: Imagine MLS #23011789
Contingent
$1,495,000
Jun 23, 2023
Source: Imagine MLS #23011787
Listed For Sale
$1,495,000
Apr 21, 2023
Source: Imagine MLS #22022644
ListingRemoved

Market trends in Lexington

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$336K
$4.83KMoM
Sale-to-List Price
99.7%
0.4%MoM
Price per sq ft
$196
$1MoM
Available listings
1048
104MoM
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Around this home

What Locals Say about Lexington

At least 1893 Trulia users voted on each feature.

  • 90 % Say there are sidewalks

  • 90 % Say it's dog friendly

  • 85 % Say car is needed

  • 82 % Say parking is easy

  • 77 % Say yards are well-kept

  • 72 % Say there's holiday spirit

  • 71 % Say kids play outside

  • 70 % Say streets are well-lit

  • 64 % Say people would walk alone at night

  • 61 % Say it's quiet

  • 52 % Say neighbors are friendly

  • 51 % Say they plan to stay for at least 5 years

  • 47 % Say it's walkable to restaurants

  • 46 % Say it's walkable to grocery stores

  • 42 % Say there's wildlife

  • 25 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Kathy Mccord
    "Schools are great"
    0
    Flag
  • 65sfvn4sj6
    "I grew up here in this neighborhood & it’s changed a lot. The crime in this area is bad but I love these older homes."
    0
    Flag
  • David Smith
    "Traffic lights are terrible and cause traffic also Lexington drivers are not the best. Getting around can be stressful and time consuming "
    0
    Flag
  • Xj6gtrh65v
    "Not sure of too many events close to this neighborhood that occur . We enjoy a few eating places close by us in this area of Pimlico Pkwy. A lot of dog walkers are friendly and most pick up after their dogs. Mostly a quiet residential area with many duplexes rented out….. "
    0
    Flag
  • Gllladysnash
    "Good place to raise a family good schools nice people great store opening I love the area that I live in it’s "
    1
    Flag
  • hayeskwyatt
    "I work in an office building on Harrodsburg Road in my commute takes less than 15 minutes. In the past, I used to work in Versailles and that commute only took 30 minutes."
    0
    Flag
  • Monica Graves
    "The neighborhood is on a bus line and it is surrounded by a community. Nice neighborhood is the access to Nicholasville Road in the shopping centers. Tates Creek Manor War is very convenient."
    0
    Flag
  • Kathy Bond
    "It’s an area where there are long time residents and also tenants. People seem to be friendly but as in all neighborhoods there are people who don’t always do the best thing for the area. No hoa so people can keep a boat or trailer in their year. The up side of no hoa "
    2
    Flag
  • Awillhoitm
    "Lots of sidewalks, decent schools zone. Main roads are loud, but relatively safe area. Decently easy commute for most jobs and stores."
    0
    Flag
  • Tiffany Rose
    "Other dog owners do not pick up after their dog and this is a reoccurring instance it’s not just like one person or two people"
    1
    Flag
  • Cassidy Sullivan
    "There’s a wonderful dog community here, people always walking them. Just beware the occasional pet parent that doesn’t pay attention to their dog or others around them. "
    0
    Flag
  • Jky859
    "It is Rural Lexington Ky and it is beautiful, quiet, and distance from neighbors. It is convenient because you are less than 15 minutes from groceries, restaurants, bars, and shopping."
    0
    Flag
  • Amy Whitmer
    "There’s Plenty of green space. There are lots of dogs being walked. People are generally respectful of picking up after their dogs. "
    0
    Flag
  • Bill Embry
    "My neighbor is safe, friendly and easy to get around. Good variety of grocery stores and everything you need within a mile."
    0
    Flag
  • Vanessalhuff
    "We have neighborhood get together on our green space a couple times a year with a food truck and once there was a band. "
    0
    Flag
  • Jorgebenito77
    "Traffic is terrible around the city. The city planning is absolutely terrible and the traffic lights are a joke"
    0
    Flag
  • Jackie Kopp
    "School events, festivals, horse racing, Great friendly place to raise a family. So many events. This is the largest small town I know. "
    0
    Flag
  • Jackie Kopp
    "Feels like a great place to raise a family. Safe for kids to walk around neighborhood. High school could be better"
    0
    Flag
  • Lalahd
    "I’ve lived here for 6 years and is a perfect location. Minutes from downtown Lexington and 20 minutes from Georgetown, Frankfort, or any other areas of the city. "
    1
    Flag
  • LaVonta Watkins
    "There are parks with walking paths and baggy stations for their dogs. The parks are equipped with various stations for various ages."
    1
    Flag
  • D8gp4wdwtv
    "I feel people in the community should come together and make things better as a whole instead of individual all as equal "
    5
    Flag
  • Jky859
    "Downtown has a lot of social events, parades, socials, and so forth. Local churches sponsor a lot of group activities for children and adults, live music and worship, and community projects. There are a lot of bars, restaurants, music venues, college campus culture and sports. "
    2
    Flag
  • Alex.cornett
    "Holidays, garage sales, mall, fire station, dogs, school sales, trick or treating, gardening, test test "
    0
    Flag
  • Trulia User
    "Just moved, and feel so invited. Everyone is kind. No cookie cutter feel like my old neighborhood. I made a good choice moving here "
    2
    Flag
  • Trulia User
    "The neighborhood does nothing together. most of the neighbors have owned their townhouse for a while and still don't speak to each other. "
    1
    Flag
  • Trulia User
    "Awesome neighborhood with great neighbors that truly care about their community. Been here for over 10 years and the neighborhood keeps getting better."
    0
    Flag
  • Trulia User
    "I am living here and is a great neighborhood it is safe, clean, and in a good shape. nowadays there a lot of houses that are being renovated. "
    1
    Flag
  • Trulia User
    "there's lots of other dogs in the neighborhood and friendly neighbors as well. it's an overall great neighborhood to live in with a lot of kind people. "
    0
    Flag
  • Trulia User
    "I don't know the neighborhood very well anymore ,it's been a while since I lived there, I just feel more comfortable moving back "
    2
    Flag
  • Trulia User
    "There are a ton of rental properties in this area and near the local high school. Traffic can be dense around school times. "
    0
    Flag
  • Trulia User
    "good school district, and trying to find a single family home. where I live is a 15 minute drive for me to get to work super convenient also I am close to other stores "
    0
    Flag
  • Trulia User
    "there is a park just up the street. It is a friendly neighborhood. with the oaks condos right next door. "
    0
    Flag
  • Trulia User
    "No where go and they hang out with life is short do not be inresponseable as parents communication is the key share location "
    0
    Flag
  • Trulia User
    "it's a safe place to raise your kids and walking or running is safe too. Driving is minimal and the traffic flows."
    1
    Flag
  • Trulia User
    "I live in the neighborhood for almost 7 years now and I do have a couple good neighbors. We do look at for each other. "
    3
    Flag
  • Trulia User
    "Family neighborhood. Nice to walk around. Have to lock doors though and can be noisy with cars. Great 4th of July parties. "
    0
    Flag
  • Trulia User
    "this neighborhood is so lovely. neighbors truly care for each other. you can sit on your porch to enjoy a quiet morning and see people walk their dogs, always waving hello. it has been a wonderful time living in this beautiful neighborhood. people care for their homes and for each other. "
    9
    Flag
  • Trulia User
    "Many older folks live here. Feel homey. Although there are neighborhoods that is a little bit run down like duplexes near by. They dont really bother you. I consider this area a safe place to live and raise a family:)"
    0
    Flag
  • Trulia User
    "friendly neighbors great community areas and play parks for kids event grocery stores Banks liquor stores gas station"
    0
    Flag
  • Trulia User
    "There is dog owners everywhere & there is also multiple dog parks. Everyone is respectful and most dog owners pick up after their dogs use the restroom. "
    3
    Flag

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Homes for sale near 5000 Winchester Rd

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Off Market Homes Near 5000 Winchester Rd

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Frequently asked questions about 5000 Winchester Rd

  • What is 5000 Winchester Rd estimated to be worth?
    Trulia's estimated value for 5000 Winchester Rd in Lexington, KY is $1,787,200.
  • What is the price history for 5000 Winchester Rd?
    5000 Winchester Rd in Lexington, KY last sold for $1,495,000 in August 2023.
  • Is Lexington a buyer's or seller's market?
    Lexington is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Lexington?
    The median sale price in Lexington is $332K. That is up $5K from the prior month.
  • How big is the lot at 5000 Winchester Rd?
    The lot at 5000 Winchester Rd in Lexington, KY is about 40 acres.
  • Does 5000 Winchester Rd have a garage?
    Yes, 5000 Winchester Rd in Lexington, KY has a garage.
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