5000 Winchester Rd, Lexington, KY 40509
OFF MARKET

5000 Winchester Rd
Lexington, KY 40509

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

$1,921,700

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $10,816/mo*
Refinance Your Home

$1,921,700

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $10,816/mo*
Refinance Your Home
6 Beds
5 Baths
9,958 sqft
(on 40 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from September 03, 2025

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

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 3 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 History for 5000 Winchester Rd

DatePriceEventSource
08/25/2023$1,495,000Sold
Imagine MLS #23011787
07/13/2023$1,495,000PendingImagine MLS #23011787
06/30/2023$1,495,000ContingentImagine MLS #23011789
06/23/2023$1,495,000Listed For SaleImagine MLS #23011787
04/21/2023ListingRemovedImagine MLS #22022644
12/07/2022$4,495,000PriceChange
Imagine MLS #22022644
10/13/2022$4,950,000Listed For SaleImagine MLS #22022644
Skip to last item
  • Results are loading
Skip to first item

Comparable Sales for 5000 Winchester Rd

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
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
1,600
2616 Cayman Heights Ln, Lexington, KY
2.08
Single-Family Home
$2,446,227
06/11/25
5
5.5
7,825
4039 Royster Rd, Lexington, KY
1.31
Single-Family Home
$350,000
03/24/26
4
2
1,798
3905 N Cleveland Rd, Lexington, KY
2.44
Single-Family Home
$1,600,000
03/31/26
4
5.5
6,216
3981 Winchester Rd, Lexington, KY
1.63
Single-Family Home
$468,000
03/06/26
3
2.5
3,255

Assigned Schools

These are the assigned schools for 5000 Winchester Rd.
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 Lexington

At least 1890 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

Learn more about our methodology.
  • 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 "
    0
    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
    "I've lived in this neighborhood before and it was quiet and very well maintained by the neighbors. "
    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
  • Trulia User
    "Families ride there bikes and walk in our neighborhood! Clean park down out street , close grocery stores Pharmacies, Doctors,Fire Department . Hospitals schools"
    0
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
  • Results are loading
Skip to first item

Homes for sale near 5000 Winchester Rd

Skip to last item
Skip to first item
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.

Homes for rent near 5000 Winchester Rd

Skip to last item
  • Results are loading
Skip to first item

Off Market Homes Near 5000 Winchester Rd

Skip to last item
Skip to first item

Explore by feature

5000 Winchester Rd, Lexington, KY 40509 is a 6 bedroom, 5 bathroom, 9,958 sqft single-family home built in 1938. This property is not currently available for sale. 5000 Winchester Rd was last sold on Aug 25, 2023 for $1,495,000 (0% higher than the asking price of $1,495,000). The current Trulia Estimate for 5000 Winchester Rd is $1,921,700.