Winchester, KY Homes

/101
$1,290,000 Pending
- 5 Beds
- 5 Baths
- 5,666 Sq Ft
3760 Old Boonesboro Rd, Winchester, KY 40391

Step through the striking red front doors and into a home where craftsmanship, character, and comfort come together. This beautifully maintained property sits on nearly 13 acres at the edge of Winchester, offering a peaceful retreat with the charm of a mid century floorplan and rich woodwork, tile, and hardwood floors throughout. The spacious kitchen and all three full baths feature high end

Josh Wood Freedom Realty & Property Management

3760 Old Boonesboro Rd, Winchester, KY 40391
/65
$380,000 Sold Jun 19, 2025

399 Stonecrest Rd, Winchester, KY 40391
- 3 Beds
- 4 Baths
- 4,572 Sq Ft
- Built 1976
Last Sold Summary
- 4% Below List Price
- $83/SF
- 3 Days On Market
Current Estimated Value $403,866

Last Listing Agent ROBIN TRIMBLE HomeFirst Real Estate

399 Stonecrest Rd, Winchester, KY 40391

/8
Est $240,319 Not Listed For Sale

109 Alabama St, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,359 Sq Ft
- Built 1930
109 Alabama St, Winchester, KY 40391

Last Sold Summary
- 6% Above List Price
- $167/SF
- 9 Days On Market
- Last Sold Price $227,000
- May 31, 2023
Last Listing Agent Andrew Fugitt Coldwell Banker McMahan

/55
$645,000
- 4 Beds
- 3.5 Baths
- 3,431 Sq Ft
7919 Mount Sterling Rd, Winchester, KY 40391

Don't let this stunning, 3,431sqft home featuring 4 bed rooms and 3 full baths, sitting on 3 acres, slip through your hands! Custom built brick home nestled in a serene, park like setting overlooking Stoner Creek. Step into to the dramatic two story entryway welcoming you with custom cabinetry and detailed finishes throughout. One of the most captivating features is the sunroom, overlooking the

Hannah Toole Coldwell Banker McMahan

7919 Mount Sterling Rd, Winchester, KY 40391
/114
$635,000 Sold Sep 30, 2025

315 The Woods Ln, Winchester, KY 40391
- 5 Beds
- 4.5 Baths
- 5,524 Sq Ft
- Built 1995
Last Sold Summary
- 2% Below List Price
- $115/SF
- 63 Days On Market
Current Estimated Value $624,817

Last Listing Agent Terri McGraw FC Tucker Bluegrass

315 The Woods Ln, Winchester, KY 40391

/23
Est $199,506 Not Listed For Sale

112 Georgia St, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,738 Sq Ft
- Built 1930
112 Georgia St, Winchester, KY 40391

Last Sold Summary
- 25% Above List Price
- $92/SF
- 8 Days On Market
- Last Sold Price $160,000
- Nov 07, 2023
Last Listing Agent Wayne Elkins RE/MAX

/42
$360,000
- 4 Beds
- 4.5 Baths
- 4,798 Sq Ft
502 W Lexington Ave, Winchester, KY 40391

Investment opportunity in the heart of Winchester! Brick Triplex featuring a main level, high visibility commercial space with Lexington Avenue frontage and two apartments on the upper level! Each apartment has two bedrooms, one bath. One unit has been recently remodeled, the other has potential for value add. The flexible commercial space contains 2 full and 1 half bath. Laundry hook-ups in all

Jason Townsend Kentucky Residential Real Estate, LLC

502 W Lexington Ave, Winchester, KY 40391
/30
$189,900 Sold Mar 16, 2026

357 E Washington St, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,328 Sq Ft
- Built 1940
Last Sold Summary
- 5% Below List Price
- $143/SF
- 26 Days On Market
Current Estimated Value $186,740

Last Listing Agent Dylan Justice GSP Homes

357 E Washington St, Winchester, KY 40391

/48
Est $247,455 Not Listed For Sale

104 Georgia St, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,758 Sq Ft
- Built 1930
104 Georgia St, Winchester, KY 40391

Last Sold Summary
- 1% Above List Price
- $139/SF
- 9 Days On Market
- Last Sold Price $245,000
- Dec 23, 2024
Last Listing Agent Libby VanMeter Marshall Lane Real Estate - Lexington

/59
$274,900
- 3 Beds
- 2 Baths
- 1,311 Sq Ft
403 Pueblo Ct, Winchester, KY 40391

Built in 2020, this well-maintained Craftsman-style ranch offers the benefits of newer construction without the wait or added cost. Located in Winchester, KY, this home combines comfort, functionality, and convenience in one clean package. Featuring 3 bedrooms and 2 full baths, the layout is designed for everyday living with an open feel and thoughtful flow throughout. The kitchen includes

Josh Wood Freedom Realty & Property Management

403 Pueblo Ct, Winchester, KY 40391
/33
$159,200 Sold Oct 09, 2025

646 Laura Dr, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,534 Sq Ft
- Built 1980
Last Sold Summary
- 6% Below List Price
- $104/SF
- 16 Days On Market
Current Estimated Value $230,218

Last Listing Agent Kimberly Brunson Hunter Real Estate

646 Laura Dr, Winchester, KY 40391

/44
Est $187,907 Not Listed For Sale

118 Alabama St, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,408 Sq Ft
- Built 1940
118 Alabama St, Winchester, KY 40391

Last Sold Summary
- 32% Above List Price
- $101/SF
- 1 Day On Market
- Last Sold Price $142,000
- Jul 18, 2024
Last Listing Agent Susan Moore Keller Williams Legacy Group

/19
$265,000
- 4 Beds
- 3 Baths
- 2,445 Sq Ft
130 E Broadway St, Winchester, KY 40391

Turnkey downtown triplex with tenants already in place. An excellent addition to any investor's portfolio. Two units have been recently updated, while the third features a long-term tenant with future value-add potential. Property includes two 1BD/1BA units and one 2BD/1BA unit. Tenants pay all utilities directly except water, which is on a RUB system, keeping operating costs low. Strong income

Sarah May Mayca Property Solutions

130 E Broadway St, Winchester, KY 40391
/32
$183,000 Sold Jul 30, 2025

517 Hidden Hills Way, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
- Built 2001
Last Sold Summary
- $163/SF
- 78 Days On Market
Current Estimated Value $207,489

Last Listing Agent Brenda Sipes Bridgewater Real Estate

517 Hidden Hills Way, Winchester, KY 40391

/28
Est $250,266 Not Listed For Sale

116 Alabama St, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,626 Sq Ft
- Built 1940
116 Alabama St, Winchester, KY 40391

Last Sold Summary
- 8% Above List Price
- $142/SF
- 95 Days On Market
- Last Sold Price $231,000
- Mar 14, 2024
Last Listing Agent Cheri Shaffer Keller Williams Commonwealth

/54
$719,900
- 3 Beds
- 3.5 Baths
- 3,388 Sq Ft
1480 Irvine Rd, Winchester, KY 40391

Beautifully remodeled farmhouse on 10 fenced acres! This 3 bedroom, 3.5 bath home with a fully finished basement offers the perfect blend of modern upgrades and country living. Inside, you'll find refinished hardwood floors and fresh paint throughout. The custom kitchen is designed to impress with new cabinetry, granite countertops, glass subway tile backsplash, double ovens, two dishwashers, and

Ivanna Barko National Real Estate

1480 Irvine Rd, Winchester, KY 40391
/61
$220,000 Sold Nov 10, 2025

313 Snowden Dr, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,232 Sq Ft
- Built 1960
Last Sold Summary
- 12% Below List Price
- $179/SF
- 51 Days On Market
Current Estimated Value $227,370

Last Listing Agent Josh Wood Freedom Realty & Property Management

313 Snowden Dr, Winchester, KY 40391

/27
Est $253,655 Not Listed For Sale

335 S Main St, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,968 Sq Ft
- Built 1920
335 S Main St, Winchester, KY 40391

Last Sold Summary
- 2% Above List Price
- $127/SF
- 41 Days On Market
- Last Sold Price $249,500
- Jul 19, 2024
Last Listing Agent Shari Frasure Keller Williams Commonwealth

/33
$209,900 Pending
- 3 Beds
- 1 Bath
- 1,050 Sq Ft
59 Holiday Rd, Winchester, KY 40391

Don't Wait - this home is priced to Sell! All one level brick ranch features 3 Bedrooms, 1-bath. Newer updates include interior paint and laminate flooring giving the home a clean modern feel. The living spaces are filled with natural light, making the home feel warm and inviting. Step out to a spacious deck and large backyard - great for entertaining or just enjoying the outdoor space. Need

Kathy Burton Coldwell Banker McMahan

59 Holiday Rd, Winchester, KY 40391
/32
$285,000 Sold Jul 03, 2025

602 Laura Dr, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,690 Sq Ft
- Built 1976
Last Sold Summary
- 11% Below List Price
- $169/SF
- 168 Days On Market
Current Estimated Value $287,110

Last Listing Agent Ryan O'Gara Real Broker, LLC

602 Laura Dr, Winchester, KY 40391

/35
Est $232,391 Not Listed For Sale

24 Hughes Ave, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
- Built 2024
24 Hughes Ave, Winchester, KY 40391

Last Sold Summary
- 22% Above List Price
- $158/SF
- 24 Days On Market
- Last Sold Price $189,900
- Jan 16, 2025
Last Listing Agent Nena Honaker Tom Goebel & Company

/2
$100,000
- Land
- 13,939 Sq Ft
- $312,500 per Acre
115 Duclair Dr, Winchester, KY 40391

Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

John Wilson Bluegrass Properties Group

115 Duclair Dr, Winchester, KY 40391
/17
$595,000 Sold Nov 17, 2025

304 Winterberry Dr, Winchester, KY 40391
- 7 Beds
- 4 Baths
- 4,386 Sq Ft
- Built 1999
Last Sold Summary
- 1% Below List Price
- $136/SF
- 10 Days On Market
Current Estimated Value $587,249

Last Listing Agent Beckie Moore Bluegrass Properties Group

304 Winterberry Dr, Winchester, KY 40391

/20
Est $199,596 Not Listed For Sale

38 Hughes Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
- Built 1940
38 Hughes Ave, Winchester, KY 40391

Last Sold Summary
- 21% Above List Price
- $123/SF
- 8 Days On Market
- Last Sold Price $165,000
- May 22, 2023
Last Listing Agent Destiny Darby Keller Williams Commonwealth

/23
$175,000
- 2 Beds
- 1 Bath
- 1,228 Sq Ft
220 Jackson St, Winchester, KY 40391

Welcome to 220 Jackson Street in Winchester, KY 40391 - a great opportunity to own a home full of character in a convenient location. Whether you're a first-time buyer, investor, or looking to downsize, this property offers both comfort and potential. Inside, you'll find a functional layout with inviting living spaces that make everyday living easy. The home provides a warm and welcoming feel,

Hunter Miller GSP Homes

220 Jackson St, Winchester, KY 40391
/2
$185,000 Sold Nov 28, 2025

23 Hillcrest Dr, Winchester, KY 40391
- 2 Beds
- 1 Bath
- 1,557 Sq Ft
- Built 1962
Last Sold Summary
- 12% Below List Price
- $119/SF
- 18 Days On Market
Current Estimated Value $198,967

Last Listing Agent Samantha Gray National Real Estate

23 Hillcrest Dr, Winchester, KY 40391

/41
Est $239,661 Not Listed For Sale

254 S Highland St, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 3,395 Sq Ft
- Built 1935
254 S Highland St, Winchester, KY 40391

Last Sold Summary
- 20% Above List Price
- $59/SF
- 10 Days On Market
- Last Sold Price $200,000
- Apr 30, 2024
Last Listing Agent Michelle Blackburn RE/MAX

/2
$110,000
- Land
- 14,810 Sq Ft
- $323,529 per Acre
230 Duclair Dr, Winchester, KY 40391

Looking for a place to build a Upscale homein Central Kentucky? The Reserve is what Winchester has been waiting for! The development has 38 large lots that overlook central KY bluegrass. This Luxury subdivision is going to be the place to built your Dream home.

John Wilson Bluegrass Properties Group

230 Duclair Dr, Winchester, KY 40391
/18
$246,500 Sold May 16, 2025

6278 Irvine Rd, Winchester, KY 40391
- 3 Beds
- 1.5 Baths
- 1,176 Sq Ft
- Built 1978
Last Sold Summary
- 7% Below List Price
- $210/SF
- 35 Days On Market
Current Estimated Value $271,143

Last Listing Agent Angela Yonts EXP Realty, LLC

6278 Irvine Rd, Winchester, KY 40391

/24
Est $195,618 Not Listed For Sale

54 Winn Ave, Winchester, KY 40391
- 5 Beds
- 2 Baths
- 1,530 Sq Ft
- Built 1940
54 Winn Ave, Winchester, KY 40391

Last Sold Summary
- 9% Above List Price
- $118/SF
- 90 Days On Market
- Last Sold Price $180,000
- Oct 01, 2024
Last Listing Agent Lukas Owens The Brokerage

/37
$1,575,000
- 37 Beds
- 19.5 Baths
- 26,124 Sq Ft
2 N Main St, Winchester, KY 40391

Major CAPEX in 2022 & 2024 — Facade transformation, fully restored and renovated.Current grossing $168,000 annual rent, with $4,000/month upside — beats the 1% rule! The Kerr Building, the largest downtown historical landmark, features structural repairs, new roofing, brick tuck-pointing, secure key-fob entrances, central HVAC, modern kitchens, updated baths, and new flooring. 18 LIHTC

Blanca Cheung Tsubaki Group, LLC

2 N Main St, Winchester, KY 40391
/22
$216,000 Sold Feb 27, 2026

521 Acadia Way, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 1,370 Sq Ft
- Built 2001
Last Sold Summary
- 2% Below List Price
- $158/SF
- 17 Days On Market
Current Estimated Value $221,677

Last Listing Agent Tyler I Back The Brokerage

521 Acadia Way, Winchester, KY 40391

/33
Est $249,308 Not Listed For Sale

144 E Broadway St, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,544 Sq Ft
- Built 1930
144 E Broadway St, Winchester, KY 40391

Last Sold Summary
- 22% Above List Price
- $81/SF
- 119 Days On Market
- Last Sold Price $205,000
- Jan 19, 2024
Last Listing Agent Thomas Harper Tom Harper and Associates

/16
$160,000
- 3 Beds
- 1 Bath
- 1,097 Sq Ft
220 E Washington St, Winchester, KY 40391

Investors take note, tenant occupied home, 3 bedrooms, 1 bathroom, one level living! Flippers, downsizing, or First-time buyers get ready! Wood style floors, covered front porch, back yard with patio...Do not miss an opportunity to add to your rental portfolio investment, start your real estate adventure, or make this home your own! Home is occupied 24-hour notice is required to show.

Whitney Ensor Ensor Real Estate, LLC

220 E Washington St, Winchester, KY 40391
/86
$515,000 Sold Apr 17, 2026

125 Casa Landa Way, Winchester, KY 40391
- 4 Beds
- 3.5 Baths
- 3,848 Sq Ft
- Built 1999
Last Sold Summary
- 6% Below List Price
- $134/SF
- 88 Days On Market
Current Estimated Value $526,775

Last Listing Agent Maggie Napier Napier Realtors

125 Casa Landa Way, Winchester, KY 40391

/22
Est $222,473 Not Listed For Sale

44 Buckner St, Winchester, KY 40391
- 3 Beds
- 1 Bath
- 1,309 Sq Ft
- Built 1935
44 Buckner St, Winchester, KY 40391

Last Sold Summary
- 18% Above List Price
- $144/SF
- 143 Days On Market
- Last Sold Price $188,000
- Mar 31, 2025
Last Listing Agent W Tyce McCullough Rector Hayden Realtors

/4
$625,000 New Construction
- 3 Beds
- 2.5 Baths
- 2,405 Sq Ft
424 Alexis Way, Winchester, KY 40391

Introducing the Castleton, a stunning home designed to impress in the sought-after Mallard Cove neighborhood. This exquisite floor plan features a side-turned garage and captivating curb appeal with double front entry doors. Inside, you'll find a thoughtfully designed split-bedroom layout with a spacious primary suite that includes a luxurious ensuite with a walk-in closet, double vanity, tile

Shane Underwood Keller Williams Commonwealth

424 Alexis Way, Winchester, KY 40391
/27
$269,000 Sold Apr 20, 2026

916 Stratton Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
- Built 1988
Last Sold Summary
- $192/SF
- 0 Days On Market
Current Estimated Value $262,927

Last Listing Agent Joshua Davis The Agency

916 Stratton Ln, Winchester, KY 40391

/17
Est $306,999 Not Listed For Sale

129 S Highland St, Winchester, KY 40391
- 6 Beds
- 4 Baths
- 3,608 Sq Ft
- Built 1940
129 S Highland St, Winchester, KY 40391

Last Sold Summary
- 14% Above List Price
- $75/SF
- 86 Days On Market
- Last Sold Price $269,000
- Jan 31, 2025
Last Listing Agent Joshua Lynch The Brokerage

/19
$235,000
- 3 Beds
- 2 Baths
- 1,502 Sq Ft
357 Silverton Way, Winchester, KY 40391

This updated home offers easy access to I-64 and downtown Winchester. See ceiling fans in every room, upstairs bonus room, modern lighting in the kitchen and bath, and new appliances, countertops, and backsplash. Enjoy a peaceful, quiet neighborhood and a relaxing rural view from the backyard. A clean, comfortable, move-in-ready home with thoughtful upgrades throughout.

Frank Mulder Tru Life Real Estate

357 Silverton Way, Winchester, KY 40391

Showing Results 441 - 480, Page 12 of 18

Kentucky Clark County Winchester

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Winchester, KY Homes

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