Winchester, KY Homes

/91
Est $431,727 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,514 Sq Ft
2184 Cole Rd, Winchester, KY 40391

2184 Cole Rd, Winchester, KY 40391

/57
$630,000
- 3 Beds
- 2 Baths
- 2,053 Sq Ft
670 Lillies Ferry Rd, Winchester, KY 40391

Escape to this serene and private 12+ acre property, boasting a 3BR/2BA home sitting on a partially finished walkout basement, that provides ample space for a home office, playroom, or additional living area. This charming home has lots of recent upgrades, including a brand new HVAC system, ensuring a comfortable living space year-round. The exterior of the home has been upgraded with new

Jennifer Helton EXP Realty, LLC

670 Lillies Ferry Rd, Winchester, KY 40391
/31
$88,500 Sold Aug 08, 2025
- 1,144 Sq Ft
- $77/SF
- 28 Days On Market
- 3 Beds
- 1 Bath
- Built 1945
15 Sycamore St, Winchester, KY 40391

3 bedroom 1 bath house. Older home that needs some updates. This house is being sold online at www.goochsells.com. Selling as/is, must close within 30 days from close of auction. 10% Buyers Premium, 10% down night of sell. Rony Jo Ballou Auctioneer 859-595-6808

Rony Jo Ballou Power House Realty

15 Sycamore St, Winchester, KY 40391

/29
Est $147,380 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,005 Sq Ft
2277 Muddy Creek Rd, Winchester, KY 40391

2277 Muddy Creek Rd, Winchester, KY 40391

/30
$259,000
- 3 Beds
- 2 Baths
- 1,550 Sq Ft
312 Forest Ave, Winchester, KY 40391

Welcome home to this beautifully remodeled 3 bedroom, 2 bathroom brick ranch in a well-established neighborhood. Nearly everything is new, including the roof, plumbing, and kitchen appliances. You'll love the refinished hardwood floors and stylish fixtures throughout. The kitchen features gorgeous granite countertops and an island with bar seating. One bathroom offers a tiled shower with a

Michelle Blackburn RE/MAX Creative, Winchester

312 Forest Ave, Winchester, KY 40391
/32
$349,900 Sold Aug 01, 2025
- 2,111 Sq Ft
- $166/SF
- 2 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1998
275 Cross Brook Ct, Winchester, KY 40391

Tucked away on a quiet corner cul-de-sac, this 3-bedroom, 2.5-bath home offers space, style, and versatility. Inside, you'll find updated flooring, large bedrooms, and an open layout perfect for everyday living and entertaining. The oversized walk-in pantry and 2-car garage add function and storage, while the huge additional building out back sets this property apart—ideal for a workshop, home

Amanda Stewart Selling the South Realty

275 Cross Brook Ct, Winchester, KY 40391

/23
Est $254,256 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,487 Sq Ft
421 Jameson Way, Winchester, KY 40391

421 Jameson Way, Winchester, KY 40391

/42
$229,900
- 3 Beds
- 2 Baths
- 2,142 Sq Ft
363 S Main St, Winchester, KY 40391

* Inspection report provided with accepted offer. Seller has made several repairs since receiving the inspection. Welcome to 363 South Main Street in the heart of Winchester, Kentucky! This charming 3-bedroom, 2-bath home offers the perfect blend of timeless character and modern convenience. Built in 1940, the home exudes classic appeal with thoughtful updates that meet today's lifestyle.

Zachary Otis HomeLand Real Estate Inc

363 S Main St, Winchester, KY 40391
/53
$867,500 Sold Aug 01, 2025
- 4,698 Sq Ft
- $185/SF
- 318 Days On Market
- 4 Beds
- 4.5 Baths
- Built 1885
511 Boone Ave, Winchester, KY 40391

One of a kind opportunity to live in history and in luxury in one of Winchester's finest offerings. This majestic home spares no detail, offering charming details throughout like hardwood floors, high ceilings, large windows, crown moldings, and fireplaces throughout. As well, the gracious lot offers expansive views and privacy with its large patio seating area and beautiful swimming pool. Ripe

Greg Leveridge Block + Lot Real Estate

511 Boone Ave, Winchester, KY 40391

/54
Est $266,681 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,776 Sq Ft
427 Jameson Way, Winchester, KY 40391

427 Jameson Way, Winchester, KY 40391

/25
$309,000
- 3 Beds
- 2.5 Baths
- 1,800 Sq Ft
202 Dubuy Dr, Winchester, KY 40391

Welcome to this move-in ready 3-bedroom, 2.5-bath home built in 2022. With 1,745 sq. ft., a finished walk-out basement, and thoughtful upgrades, it's designed for comfort with a modern touch.The kitchen features upgraded high-gloss cabinetry, custom granite countertops, and stainless steel appliances. Inside, waterproof luxury vinyl plank (LVP) flooring runs throughout the whole home,

Donna Mink Mink Realty

202 Dubuy Dr, Winchester, KY 40391
/43
$129,900 Sold Jul 31, 2025
- 858 Sq Ft
- $151/SF
- 3 Days On Market
- 2 Beds
- 1 Bath
- Built 1959
44 Watts Rd, Winchester, KY 40391

Tucked away on a peaceful dead-end street with minimal traffic, this inviting 2-bedroom, 1-bath home offers comfort, convenience, and character. Step inside to find beautiful hardwood floors throughout, a spacious living room full of natural light, and a cozy eat-in kitchen perfect for casual meals and morning coffee.Enjoy the privacy of a fenced backyard—ideal for relaxing, gardening, or

Josh Wood Freedom Realty & Property Management

44 Watts Rd, Winchester, KY 40391

/45
Est $240,294 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,260 Sq Ft
334 Vanover Way, Winchester, KY 40391

334 Vanover Way, Winchester, KY 40391

/94
$895,000
- 4 Beds
- 3.5 Baths
- 4,584 Sq Ft
4040 Muddy Creek Rd, Winchester, KY 40391

A Farmhouse Retreat with Timeless Craftsmanship on 13.6 AcresNestled on 13.6 rolling acres in Clark County, this custom built farmhouse captivates with soaring tongue-and-groove ceilings, rich woodwork, and thoughtful craftsmanship that sets this home apart. Oversized doors, custom cabinetry, and detailed finishes showcase the quality throughout, while two wood-burning fireplaces with

Julie Wiggington RE/MAX Creative, Winchester

4040 Muddy Creek Rd, Winchester, KY 40391
/60
$182,000 Sold Jul 31, 2025
- 1,140 Sq Ft
- $160/SF
- 2 Days On Market
- 3 Beds
- 2 Baths
- Built 2024
265 Cunningham Ln, Winchester, KY 40391

Country Living at Its Finest Y'all! Pack the U-Haul and get excited because this nearly new single wide home is awaiting its new owners! It has a split bedroom floor plan, fully equipped kitchen and handy laundry/mud room that leads to the back yard. With 1.429 acres, you have room to roam all while being located only minutes from the Mountain Parkway.

Amanda Marcum Berkshire Hathaway HomeServices Foster Realtors

265 Cunningham Ln, Winchester, KY 40391

/25
Est $246,495 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,428 Sq Ft
325 Vanover Way, Winchester, KY 40391

325 Vanover Way, Winchester, KY 40391

/10
$100,000
- Land
- 3.91 Acres
- $25,575 per Acre
6345 Muddy Creek Rd, Winchester, KY 40391

Beautiful lot in Clark County with just under four acres. Owner/ Agent property. Deed restrictions apply

Chase Parrish Taylor Real Estate, LLC

6345 Muddy Creek Rd, Winchester, KY 40391
/92
$364,900 Sold Jul 31, 2025
- 2,520 Sq Ft
- $145/SF
- 209 Days On Market
- 4 Beds
- 2 Baths
- Built 1962
31 Mockingbird Valley Rd, Winchester, KY 40391

This stately, split-level brick home is situated in the beautiful and desirable Hampton Manor subdivision, right in the heart of Winchester. On the main level, gleaming hardwood floors extend throughout, including the newly renovated kitchen with new granite countertops, new cabinets, all new appliances, new faucet and a large island providing plenty of space to prepare family meals. Three

Josh Wood Freedom Realty & Property Management

31 Mockingbird Valley Rd, Winchester, KY 40391

/28
Est $215,437 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,144 Sq Ft
306 Geronimo Ct, Winchester, KY 40391

306 Geronimo Ct, Winchester, KY 40391

/11
$100,000
- Land
- 3.91 Acres
- $25,575 per Acre
6413 Muddy Creek Rd, Winchester, KY 40391

Beautiful lot in Clark County with just under four acres. Septic tank and utilities already on site. Buyer to confirm condition. Owner/ Agent property. Deed restrictions apply. Link to 3D model of lot:

Chase Parrish Taylor Real Estate, LLC

6413 Muddy Creek Rd, Winchester, KY 40391
/3
$220,000 Sold Jul 30, 2025
- 1,300 Sq Ft
- $169/SF
- 38 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2005
412 Paisley Ct, Winchester, KY 40391

Very nice 3 bedroom 2.1 bath townhome with walk out basement. Home was upgraded 2023 with new paint,carpet, granite countertops and stainless appliances. Only minutes from Winchester bypass.

John Wilson Bluegrass Properties Group

412 Paisley Ct, Winchester, KY 40391

/26
Est $202,842 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,028 Sq Ft
129 Buffalo Trace, Winchester, KY 40391

129 Buffalo Trace, Winchester, KY 40391

/63
$1,179,000
- 3 Beds
- 3.5 Baths
- 3,672 Sq Ft
2100 Irvine Rd Unit 40391, Winchester, KY 40391

This log cabin is located on gently rolling 28 acres very few miles from town, you will think you are on vacation in the sparking pool, tastefully landscaped, fireplace in the great room which leads into a in law quarters, large kitchen that has been wonderfully remodeled with extensive detail, master suite is located on first floor, mud room, 3 1/2 baths, loft/bedroom/full bath upstairs,

Mila Ensor Ensor Real Estate, LLC

2100 Irvine Rd Unit 40391, Winchester, KY 40391
/39
$549,000 Sold Jul 30, 2025
- 3,478 Sq Ft
- $158/SF
- 100 Days On Market
- 5 Beds
- 3.5 Baths
- Built 2020
154 Hawthorne Dr, Winchester, KY 40391

This outstanding 5 bedroom, 3.5 bathroom craftsman-style home boasts custom upgrades and modern finishes throughout. Built in 2020, no detail was spared during the construction of this beautiful residence, nestled on a dead end street in the heart of Earlymeade. The main level boasts an open floor plan with 9' ceilings, spacious living room with gas fireplace & built-ins, gourmet kitchen with

Jarran Thomas The Agency

154 Hawthorne Dr, Winchester, KY 40391

/14
Est $176,963 Not Listed For Sale
- 3 Beds
- 2 Baths
- 996 Sq Ft
117 Buffalo Trace, Winchester, KY 40391

117 Buffalo Trace, Winchester, KY 40391

/6
$450,000
550 E Broadway St, Winchester, KY 40391

Prime land located on the outskirts of Winchester ready for possible development. Parcel has frontage on both East Broadway and Washington Street. Land is currently zoned A-1. Utilities available. The future awaits!!!

Keith Wilson Coldwell Banker McMahan

550 E Broadway St, Winchester, KY 40391
/32
$183,000 Sold Jul 30, 2025
- 1,120 Sq Ft
- $163/SF
- 78 Days On Market
- 3 Beds
- 2 Baths
- Built 2001
517 Hidden Hills Way, Winchester, KY 40391

Enjoy the convenience of a prime location with this property. Mature trees provide shade and privacy, while the screened sunroom offers a relaxing space. You'll also appreciate the proximity to restaurants, shopping, the Bypass, and the Interstate, making commuting and errands a breeze. Inside this beautifully updated home you will find 3 bedrooms, 2 full bathrooms, fresh paint, new

Brenda Sipes Bridgewater Real Estate

517 Hidden Hills Way, Winchester, KY 40391

/22
Est $189,143 Not Listed For Sale
- 3 Beds
- 2 Baths
- 960 Sq Ft
113 Buffalo Trace, Winchester, KY 40391

113 Buffalo Trace, Winchester, KY 40391

/67
$1,500,000
- 1 Bed
- 1 Bath
- 1,650 Sq Ft
345 Boone Ridge Ln, Winchester, KY 40515

Rare is the opportunity to own land in the Iroquois Hunt Country with the bonus of one half mile of frontage on the most beautiful stream in the Bluegrass, Boone Creek! This easily accessible frontage is opposed on the other side with rock faced palisades and the most spectacular setting imaginable. The forested slopes leading to the creek are laced with hiking and riding trails. Then when you

Linda Willson Homes & Horse Farms Real Estate

345 Boone Ridge Ln, Winchester, KY 40515
/28
$359,900 Sold Jul 30, 2025
- 1,600 Sq Ft
- $225/SF
- 311 Days On Market
- 3 Beds
- 2 Baths
- Built 2024
210 Jett Dr, Winchester, KY 40391

Open House, Sunday, June 22, 2025, 1-3Don't miss out on this wonderful ranch floor plan, New Construction, 3 bedrooms, 2 baths, covered porch, great location, Call today.Size of home may vary from plan, spec home,all specifics have already been ordered. This information will follow within a few weeks and posted on line.

Mila Ensor Ensor Real Estate, LLC

210 Jett Dr, Winchester, KY 40391

/47
Est $592,938 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,020 Sq Ft
1305 Irvine Rd, Winchester, KY 40391

1305 Irvine Rd, Winchester, KY 40391

/20
$205,000
- 2 Beds
- 2.5 Baths
- 1,197 Sq Ft
111 Quail Ridge Rd, Winchester, KY 40391

Welcome Home - Comfortable Living or Smart Investment!Step into this inviting townhome, offering both spacious comfort and excellent investment potential. Featuring two bedrooms and two and a half bathrooms, this well-designed unit boasts a generous living area with a ventless fireplace, creating a warm, welcoming atmosphere.The home's layout connects the living room, dining area, and

Kim Dice EXP Realty, LLC

111 Quail Ridge Rd, Winchester, KY 40391
/21
$285,000 Sold Jul 29, 2025
- 1,696 Sq Ft
- $168/SF
- 8 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2004
219 Bartram Ct, Winchester, KY 40391

This charming residence features a desirable first-floor primary bedroom and a spacious kitchen complete with a breakfast bar—perfect for everyday living and entertaining. Enjoy peace of mind with a brand-new roof and updated systems throughout. Located in a sought-after neighborhood close to everything you need. Don't miss the opportunity to make this home yours—schedule your showing today!

Nora Williams Keller Williams Commonwealth

219 Bartram Ct, Winchester, KY 40391

/33
Est $275,764 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,885 Sq Ft
560 E Broadway St, Winchester, KY 40391

560 E Broadway St, Winchester, KY 40391

/39
$619,900
- 4 Beds
- 5 Baths
- 4,374 Sq Ft
600 Boone Ave, Winchester, KY 40391

Step into the timeless elegance of this stunning Southern antebellum-style home, where classic charm meets modern luxury. Boasting four spacious bedrooms and five beautifully appointed bathrooms, this grand residence offers an unparalleled level of sophistication and comfort. A breathtaking foyer and entryway welcome you with a sweeping staircase, and exquisite architectural details, setting the

Holly Goeing The Agency

600 Boone Ave, Winchester, KY 40391
/40
$240,000 Sold Jul 29, 2025
- 2,617 Sq Ft
- $92/SF
- 12 Days On Market
- 5 Beds
- 3 Baths
- Built 1980
400 Verna Dr, Winchester, KY 40391

Spacious Brick Ranch with Dual Master Suites & Investor Potential! This charming 5-bedroom, 3-bath brick ranch is nestled in a well-established neighborhood and offers a rare opportunity for customization and value-add. With some renovation projects already started, this home is ideal for an investor or handy homeowner ready to build instant equity.Enjoy the flexibility of two master

Melodie Lincavage RE/MAX Elite Realty

400 Verna Dr, Winchester, KY 40391

/99
Est $266,207 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,394 Sq Ft
514 E Broadway St, Winchester, KY 40391

514 E Broadway St, Winchester, KY 40391

/4
$140,000
- Land
- 3.94 Acres
- $35,533 per Acre
12569 Ironworks Rd, Winchester, KY 40391

Build your dream home in the stunning ESKIPPAKITHIKI OVERLOOKS! Looking for your next investment? This 3.940 acre parcel offers unlimited potential-whether you dream of building or simply holding land as it gows in value. Offering unparalleled views of a serene, natural setting. Perfect for a private retreat or family estate, this property invites you to design your ideal lifestyle surrounded

Kathryn Cheuvront Coldwell Banker McMahan

12569 Ironworks Rd, Winchester, KY 40391
/28
$234,500 Sold Jul 29, 2025
- 1,200 Sq Ft
- $195/SF
- 45 Days On Market
- 3 Beds
- 2 Baths
- Built 2004
108 Sturbridge Ln, Winchester, KY 40391

Gorgeous one story home located just off the Winchester Bypass. This lovely home has three bedrooms and two full baths with a two car attached garage and deck out back. Fenced in yard!!!! Don't miss out; this one will go FAST!!! NOTE: Property must be listed for 5 days before seller will look at any offers

Jason Szaks EXIT TOWN & COUNTRY REALTORS

108 Sturbridge Ln, Winchester, KY 40391

/25
Est $237,198 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,284 Sq Ft
19 Apache Trail, Winchester, KY 40391

19 Apache Trail, Winchester, KY 40391

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