Winchester, KY Homes

/32
Est $363,113 Not Listed For Sale

505 Boone Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,044 Sq Ft
- Built 1942
505 Boone Ave, Winchester, KY 40391

Last Sold Summary
- 12% Above List Price
- $159/SF
- 1 Day On Market
Last Sold Price $324,900

Last Listing Agent Diane K Scott The Brokerage

/26
$215,000 Pending
- 2 Beds
- 1.5 Baths
- 1,120 Sq Ft
271 April Way, Winchester, KY 40391

This charming 2 - story townhouse is in a prime location.. Welcome to this beautifully maintained 2 bedroom, 1.5 bath townhouse offering the perfect blend of comfort, style and convenience. Spread over two spacious levels, this home features an inviting living area, a modern kitchen with ample cabinetry and a cozy dining space-perfect for every day living or entertaining guests. Upstairs,

Kimberly Fugate Keller Williams Commonwealth

271 April Way, Winchester, KY 40391
/2
$59,000 Sold Dec 16, 2025

1515 Sewell Shop Rd, Winchester, KY 40391
- Land
- 2.83 Acres
- $20,848 per Acre
Last Sold Summary
- 2% Below List Price
- 3 Days On Market
Last Listing Agent Zella Rosenthal Tom Goebel & Company

1515 Sewell Shop Rd, Winchester, KY 40391

/35
Est $341,102 Not Listed For Sale

121 Hampton Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,248 Sq Ft
- Built 1958
121 Hampton Ave, Winchester, KY 40391

Last Sold Summary
- 11% Above List Price
- $137/SF
- 60 Days On Market
Last Sold Price $307,500

Last Listing Agent Patrick Arvin Keller Williams Commonwealth

/37
$949,950 Pending
- 3 Beds
- 2.5 Baths
- 2,400 Sq Ft
700 Nick Ln, Winchester, KY 40391

🚨 BIG PRICE DROP ALERT! 🚨 Motivated sellers are ready to make a deal—this is your chance to snag an unbeatable offer! 💰🏡Step into country living with this amazing 120-acre working farm! You'll love the brand-new 3-bedroom, 2.5-bath home that features an open floor plan, perfect for hanging out with family or hosting friends. It's got all the modern touches, so you

Darrell Tackett Dream Maker Realty, LLC

700 Nick Ln, Winchester, KY 40391
/53
$439,000 Sold Dec 29, 2025

129 Lana Ln, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 2,844 Sq Ft
- Built 1968
Last Sold Summary
- 7% Below List Price
- $154/SF
- 110 Days On Market
Current Estimated Value $435,314

Last Listing Agent Jo Gawthrop Keller Williams Bluegrass Realty

129 Lana Ln, Winchester, KY 40391

/50
Est $445,737 Not Listed For Sale

33 Hampton Ave, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 3,580 Sq Ft
- Built 1958
33 Hampton Ave, Winchester, KY 40391

Last Sold Summary
- 17% Above List Price
- $106/SF
- 16 Days On Market
Last Sold Price $380,000

Last Listing Agent Robert Coburn Kentucky Realty Group, LLC

/27
$175,000
- 3 Beds
- 2 Baths
- 1,305 Sq Ft
6 Monroe Ave, Winchester, KY 40391

Charming Home in the Heart of Winchester! Welcome to 6 Monroe Ave - a 3-bedroom, 2-bath home full of character and modern touches. Step inside to find an inviting family room with an updated shiplap fireplace surround, perfect for cozy evenings. The kitchen is filled with natural light and features granite countertops, making it both stylish and functional. Recent updates include an HVAC system

Lindsey Bivens Berkshire Hathaway de Movellan Properties

6 Monroe Ave, Winchester, KY 40391
/37
$295,000 Sold Dec 27, 2025

115 College St, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,839 Sq Ft
- Built 1940
Last Sold Summary
- 2% Below List Price
- $160/SF
- 0 Days On Market
Current Estimated Value $290,133

Last Listing Agent Zova Rothchild Keller Williams Legacy Group

115 College St, Winchester, KY 40391

/27
Est $219,008 Not Listed For Sale

118 Southern Ct, Winchester, KY 40391
- 4 Beds
- 1.5 Baths
- 1,598 Sq Ft
- Built 1943
118 Southern Ct, Winchester, KY 40391

Last Sold Summary
- 10% Above List Price
- $125/SF
- 31 Days On Market
Last Sold Price $200,000

Last Listing Agent Susan Baldwin Threshold Real Estate Services

/53
$265,000 Pending
- 2 Beds
- 2 Baths
- 1,521 Sq Ft
174 Hidden Grove Ln, Winchester, KY 40391

Welcome home to your Kentucky River retreat! This freshly remodeled 2-bedroom, 2-bath charmer offers two inviting covered decks with beautiful river views, a fenced yard for pets or play and even a personal lift for easy access. Inside, enjoy warm, modern updates, with a bright open floor plan. All new flooring, kitchen, baths and much more! Perfect for full-time living or a peaceful getaway just

Kathryn Cheuvront Coldwell Banker McMahan

174 Hidden Grove Ln, Winchester, KY 40391
/21
$285,000 Sold Jul 29, 2025

219 Bartram Ct, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 1,696 Sq Ft
- Built 2004
Last Sold Summary
- 1% Below List Price
- $168/SF
- 8 Days On Market
Current Estimated Value $294,182

Last Listing Agent Nora Williams Keller Williams Commonwealth

219 Bartram Ct, Winchester, KY 40391

/46
Est $360,928 Not Listed For Sale

14 Western Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,676 Sq Ft
- Built 2023
14 Western Ave, Winchester, KY 40391

Last Sold Summary
- 11% Above List Price
- $194/SF
- 79 Days On Market
Last Sold Price $325,000

Last Listing Agent Dale Hatton Dream Maker Realty, LLC

/31
$204,900
- 3 Beds
- 1 Bath
- 1,290 Sq Ft
60 Hiawatha Trail, Winchester, KY 40391

Updated, affordable, and ready for you! This 3-bedroom, 1-bath home offers approximately 1,300 square feet of comfortable living space with tasteful updates that make it easy to move right in. The layout provides a welcoming feel with bright living areas and an updated kitchen and bath. Downstairs you have a possible 4th bedroom or office space. Conveniently located in Winchester close to

Christina Bucher Keller Williams Legacy Group

60 Hiawatha Trail, Winchester, KY 40391
/43
$354,000 Sold Jul 02, 2025

485 Mccullough Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 2,120 Sq Ft
- Built 1950
Last Sold Summary
- 21% Below List Price
- $167/SF
- 38 Days On Market
Current Estimated Value $375,803

Last Listing Agent Dale Hatton Dream Maker Realty, LLC

485 Mccullough Ln, Winchester, KY 40391

/18
Est $199,895 Not Listed For Sale

6 Western Ave, Winchester, KY 40391
- 2 Beds
- 2 Baths
- 2,109 Sq Ft
- Built 1950
6 Western Ave, Winchester, KY 40391

Last Sold Summary
- 48% Above List Price
- $64/SF
- 46 Days On Market
Last Sold Price $135,000

Last Listing Agent Steven G King CENTURY 21 Advantage Realty

/4
$64,900 Pending
- Land
- 0.52 Acre
- $124,808 per Acre
101 Royal Oak Dr, Winchester, KY 40391

A Unique Opportunity to Build your Dream Home in the Estate Section of Royal Oaks in Clark County. Situated on..52 acres of land and Conveniently located off Exit 96 on I-64, with close proximity to the Industrial Park, Shopping, Dining and downtown Winchester. Call listing agent for additional details and information on the few lots left to build on in this subdivision!

Melia Hord Keller Williams Legacy Group

101 Royal Oak Dr, Winchester, KY 40391
/78
$660,000 Sold Dec 10, 2025

420 Alexis Way, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,770 Sq Ft
- Built 2022
Last Sold Summary
- 5% Below List Price
- $238/SF
- 26 Days On Market
Current Estimated Value $666,607

Last Listing Agent Edwin Burden McCormick Realty Inc.

420 Alexis Way, Winchester, KY 40391

/37
Est $283,337 Not Listed For Sale

120 Milwood Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,853 Sq Ft
- Built 1965
120 Milwood Dr, Winchester, KY 40391

Last Sold Summary
- 23% Above List Price
- $124/SF
- 80 Days On Market
Last Sold Price $230,000

Last Listing Agent Michelle Blackburn RE/MAX

/4
$10,000
- Land
- 0.17 Acre
- $59,880 per Acre
117 4th St, Winchester, KY 40391

Discover the potential of this spacious 0.17-acre residential property nestled in a neighborhood community on clear and level vacant lot located in a Cul-de-sac of Lincoln Park Subdivision. This could be an investment opportunity as well, for ideal savvy investors looking to diversify your portfolio this property would be perfect for building a custom home, holding for future value, or develop

Anita McDermott Keller Williams Bluegrass Realty

117 4th St, Winchester, KY 40391
/49
$390,000 Sold Jun 30, 2025

1094 Ford Hampton Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,900 Sq Ft
- Built 1940
Last Sold Summary
- 2% Below List Price
- $205/SF
- 26 Days On Market
Current Estimated Value $392,989

Last Listing Agent Tom D. Thomas The Real Estate Co.

1094 Ford Hampton Rd, Winchester, KY 40391

/48
Est $252,842 Not Listed For Sale

132 Boone Ave, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 2,496 Sq Ft
- Built 1930
132 Boone Ave, Winchester, KY 40391

Last Sold Summary
- 63% Above List Price
- $62/SF
- 0 Days On Market
Last Sold Price $155,000

Last Listing Agent Jacob Jones Apex Realty Consultants

/7
$150,000
- Land
- 4.21 Acres
- $35,629 per Acre
1030 Craig Crossing Rd, Winchester, KY 40391

Lot # 14 contains 4.21 acres of gently rolling land with small stream perfect for your new home. This is a rare opportunity to own a piece of western Clark County real estate in the sought-after McClure Road area. Thoroughbred Estates is Winchester's newest upscale development containing 33 lots from 2 acres to nearly 7 acres. Lots are located just minutes from Winchester and Lexington.

Keith Wilson Coldwell Banker McMahan

1030 Craig Crossing Rd, Winchester, KY 40391
/21
$430,000 Sold Mar 09, 2026

870 Pilot View Rd, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,568 Sq Ft
- Built 2022
Last Sold Summary
- 2% Below List Price
- $274/SF
- 31 Days On Market
Current Estimated Value $434,200

Last Listing Agent Chelsea Morguson McCallie Real Estate

870 Pilot View Rd, Winchester, KY 40391

/39
Est $362,766 Not Listed For Sale

14 Euclid Ave, Winchester, KY 40391
- 5 Beds
- 3 Baths
- 3,660 Sq Ft
- Built 1940
14 Euclid Ave, Winchester, KY 40391

Last Sold Summary
- 20% Above List Price
- $83/SF
- 35 Days On Market
Last Sold Price $303,000

Last Listing Agent Nicole Seals Guide Realty, Inc.

/14
$159,900
- Land
- 2.66 Acres
- $60,113 per Acre
590 Craig Crossing, Winchester, KY 40391

Don't let this opportunity pass you by again. This prime lot in Thoroughbred Estates is back on the market due to Current owners change of plans. This lot is ready for your new home with a beautiful setting and located close to Winchester and Lexington in a new Luxury Subdivision. Watch the sun set each night from your rear deck or pool. Call today!!!

Keith Wilson Coldwell Banker McMahan

590 Craig Crossing, Winchester, KY 40391
/61
$545,000 Sold Jul 15, 2025

1063 Wades Mill Rd, Winchester, KY 40391
- 4 Beds
- 3.5 Baths
- 3,958 Sq Ft
- Built 2000
Last Sold Summary
- 11% Below List Price
- $138/SF
- 180 Days On Market
Current Estimated Value $566,088

Last Listing Agent Joseph Smallwood Christies International Real Estate Bluegrass

1063 Wades Mill Rd, Winchester, KY 40391

/32
Est $256,875 Not Listed For Sale

13 Euclid Ave, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,893 Sq Ft
- Built 1917
13 Euclid Ave, Winchester, KY 40391

Last Sold Summary
- 17% Above List Price
- $116/SF
- 75 Days On Market
Last Sold Price $219,000

Last Listing Agent Jim Woodrum RE/MAX

/2
$78,500
- Land
- 0.22 Acre
- $356,818 per Acre
Lot 3 Plantations Dr, Winchester, KY 40391

NOW SELLING SFH Buildable Lots of PHASE ONE: 12 Buildable Lots (minimum lot is 9600+ sqft) of PHASE ONE of Deerlawn's Development located at 2395 Paris Rd (Parent Listing). Earmarked as Winchester, Ky's most anticipated residential development consisting of an ambitious 274+-acre expansion formerly known as the well-established Royal Oaks/Plantation neighborhoods, Phase One has 12 lots ready for

Melia Hord Keller Williams Legacy Group

Lot 3 Plantations Dr, Winchester, KY 40391
/65
$290,000 Sold Jun 18, 2025

13 Robyn Dr, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,844 Sq Ft
- Built 1980
Last Sold Summary
- 2% Below List Price
- $157/SF
- 1 Day On Market
Current Estimated Value $302,277

Last Listing Agent Jason Townsend Kentucky Residential Real Estate, LLC

13 Robyn Dr, Winchester, KY 40391

/43
Est $332,840 Not Listed For Sale

201 Boone Ave, Winchester, KY 40391
- 4 Beds
- 2.5 Baths
- 2,513 Sq Ft
- Built 1909
201 Boone Ave, Winchester, KY 40391

Last Sold Summary
- 9% Above List Price
- $121/SF
- 50 Days On Market
Last Sold Price $304,500

Last Listing Agent Matt Metts LexHomes Real Estate

/34
$235,000 Pending
- 3 Beds
- 2 Baths
- 1,050 Sq Ft
12 Linden Ave, Winchester, KY 40391

Cute ranch with easy access to I-64 and downtown Winchester. Walk to the breweries, shopping and restaurants. 3 bedrooms with 2 full baths with 1 car detached garage with fenced in back yard.

Roni Porter RE/MAX Creative Realty

12 Linden Ave, Winchester, KY 40391
/29
$235,000 Sold Feb 09, 2026

142 Sturbridge Ln, Winchester, KY 40391
- 3 Beds
- 2 Baths
- 1,220 Sq Ft
- Built 2005
Last Sold Summary
- 6% Below List Price
- $193/SF
- 1 Day On Market
Current Estimated Value $240,688

Last Listing Agent Donna Mink Mink Realty

142 Sturbridge Ln, Winchester, KY 40391

/45
Est $429,829 Not Listed For Sale

142 College St, Winchester, KY 40391
- 4 Beds
- 3 Baths
- 3,012 Sq Ft
- Built 1940
142 College St, Winchester, KY 40391

Last Sold Summary
- 2% Above List Price
- $139/SF
- 87 Days On Market
Last Sold Price $420,000

Last Listing Agent Patrick Arvin Keller Williams Commonwealth

/3
$700,000 New Construction
- 3 Beds
- 2 Baths
- 2,400 Sq Ft
415 Alexis Way, Winchester, KY 40391

Introducing the Merango, a classic all-brick ranch home designed for both comfort and style. With stunning double front doors and a 2-car attached garage, this home offers incredible curb appeal and modern living. The spacious 3-bedroom, 2-bath layout features a split-bedroom design for added privacy, along with a dedicated study perfect for a home office. The open-concept kitchen is ideal for

Shane Underwood Keller Williams Commonwealth

415 Alexis Way, Winchester, KY 40391
/32
$360,000 Sold Aug 14, 2025

418 Skylark Dr, Winchester, KY 40391
- 5 Beds
- 2.5 Baths
- 2,746 Sq Ft
- Built 1990
Last Sold Summary
- 3% Above List Price
- $131/SF
- 12 Days On Market
Current Estimated Value $351,348

Last Listing Agent Kymberly McCreary Kentucky Land and Home

418 Skylark Dr, Winchester, KY 40391

/32
Est $215,951 Not Listed For Sale

8 Nunnelly Ct, Winchester, KY 40391
- 2 Beds
- 1.5 Baths
- 1,255 Sq Ft
- Built 1940
8 Nunnelly Ct, Winchester, KY 40391

Last Sold Summary
- 10% Above List Price
- $157/SF
- 33 Days On Market
Last Sold Price $197,000

Last Listing Agent Timothy Saylor Threshold Real Estate Services

/60
$279,950
- 4 Beds
- 3 Baths
- 2,112 Sq Ft
115 Watercrest Cir, Winchester, KY 40391

Stunning Home in One of the Area's Most Coveted Neighborhoods!Experience spacious living with 3 generous bedrooms and 2 full baths on the main level, designed for comfort and everyday convenience. The walkout basement offers even more space with a large bedroom and an additional full bath, ideal for guests, extended family, or a private retreat. What truly sets this home apart? The sellers are

Darrell Tackett Dream Maker Realty, LLC

115 Watercrest Cir, Winchester, KY 40391
/57
$775,000 Sold Mar 02, 2026

1700 Cabin Creek Rd, Winchester, KY 40391
- 3 Beds
- 2.5 Baths
- 2,695 Sq Ft
- Built 1994
Last Sold Summary
- $288/SF
- 33 Days On Market
Current Estimated Value $759,500

Last Listing Agent Alysia Niva Century 21 Advantage Realty - Georgetown

1700 Cabin Creek Rd, Winchester, KY 40391

/47
Est $341,323 Not Listed For Sale

113 S Burns Ave, Winchester, KY 40391
- 4 Beds
- 2 Baths
- 3,299 Sq Ft
- Built 1895
113 S Burns Ave, Winchester, KY 40391

Last Sold Summary
- 3% Above List Price
- $100/SF
- 1 Day On Market
Last Sold Price $329,900

Last Listing Agent Ginger Mccoy Kentucky Residential Real Estate, LLC

Showing Results 601 - 640, Page 16 of 18

Kentucky Clark County Winchester

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