Winchester, KY Homes

/2
$100,000
- Land
- 0.32 Acre
- $312,500 per Acre
111 Jacob Ct, 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

111 Jacob Ct, Winchester, KY 40391
/36
$345,000 Sold Jun 02, 2025
- 1,910 Sq Ft
- $181/SF
- 36 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1996
1173 Lafayette Blvd, Winchester, KY 40391

It's your lucky day! Due to no fault of the home, this great property is back on the market! Don't miss this lovely 3-bedroom, 2.5-bath ranch home in a family oriented neighborhood. Step inside to a formal dining room and a spacious living room featuring a vaulted ceiling and cozy gas log fireplace and hardwood floors. The eat-in kitchen boasts granite countertops, a pantry, and newer stainless

Janna Smith United Real Estate Bluegrass

1173 Lafayette Blvd, Winchester, KY 40391

/28
Est $250,963 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,626 Sq Ft
116 Alabama St, Winchester, KY 40391

116 Alabama St, Winchester, KY 40391

/2
$110,000
- Land
- 0.32 Acre
- $343,750 per Acre
115 Jacob Ct, 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 Jacob Ct, Winchester, KY 40391
/24
$215,000 Sold May 29, 2025
- 1,420 Sq Ft
- $151/SF
- 10 Days On Market
- 3 Beds
- 1 Bath
- Built 1973
13365 Ironworks Rd, Winchester, KY 40391

Charming and fully renovated, this 3-bedroom, 1-bathroom home offers the perfect blend of modern style and cozy comfort. With a fresh white exterior accented in black and a brand-new metal roof, it stands out with timeless curb appeal and lasting durability.Inside, every detail has been thoughtfully updated, from the sleek modern kitchen to the stylish lighting fixtures that brighten the

Joshua Davis The Agency

13365 Ironworks Rd, Winchester, KY 40391

/36
Est $195,842 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,092 Sq Ft
25 Hughes Ave, Winchester, KY 40391

25 Hughes Ave, Winchester, KY 40391

/2
$110,000
- Land
- 0.27 Acre
- $407,407 per Acre
125 Jacob Ct, 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

125 Jacob Ct, Winchester, KY 40391
/27
$274,900 Sold May 23, 2025
- 1,770 Sq Ft
- $155/SF
- 40 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1978
707 Terry Dr, Winchester, KY 40391

Welcome to 707 Terry Dr, Winchester, KY, a beautifully updated 3-bedroom, 2.5-bathroom home that blends modern comfort with a warm, inviting feel.Step inside to a spacious kitchen featuring custom cabinetry, updated appliances, and plenty of counter space perfect for everything from busy mornings to dinner with friends. The adjoining dining area with a cozy stone fireplace makes every

Kymberly McCreary EXP Realty, LLC

707 Terry Dr, Winchester, KY 40391

/27
Est $254,056 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,968 Sq Ft
335 S Main St, Winchester, KY 40391

335 S Main St, Winchester, KY 40391

/2
$110,000
- Land
- 0.32 Acre
- $343,750 per Acre
135 Jacob Ct, 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

135 Jacob Ct, Winchester, KY 40391
/48
$330,000 Sold May 23, 2025
- 2,090 Sq Ft
- $158/SF
- 35 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1970
113 Holiday Rd, Winchester, KY 40391

You must see this lovely brick home on a basement in Holiday Hills! If you like pickleball, disc golf, or anything else Wiseman Park has to offer, you will love this convenient location! 3 bedrooms, 2 and a half baths. Very practical kitchen featuring granite countertops and a brand new refrigerator. Plenty of room for entertaining with a beautiful deck just off the open concept kitchen / dining

Jason Townsend Kentucky Residential Real Estate, LLC

113 Holiday Rd, Winchester, KY 40391

/20
Est $194,965 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
38 Hughes Ave, Winchester, KY 40391

38 Hughes Ave, Winchester, KY 40391

/2
$110,000
- Land
- 0.47 Acre
- $234,043 per Acre
139 Jacob Ct, 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

139 Jacob Ct, Winchester, KY 40391
/40
$400,000 Sold May 23, 2025
- 2,432 Sq Ft
- $164/SF
- 26 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1995
109 Monet Blvd, Winchester, KY 40391

Gorgeous Two Story Charmer, Located In Highly Desirable Oak Hill Subdivision! This Spacious Home Offers 4 Bedrooms, 3 Baths, An Abundance of Space, Inviting Back Deck, Covered Front Porch, Screened In Sun Porch, Adjoining Large Detached Garage, Making For A Lovely Covered Walkway To & From. Entry Way To Mud Room And Separate Laundry, Lead To The Updated Kitchen Boasting With Ample Cabinetry,

Melissa Brown Keller Williams Legacy Group

109 Monet Blvd, Winchester, KY 40391

/12
Est $114,699 Not Listed For Sale
- 2 Beds
- 1 Bath
- 679 Sq Ft
46 Hughes Ave, Winchester, KY 40391

46 Hughes Ave, Winchester, KY 40391

/2
$110,000
- Land
- 0.59 Acre
- $186,441 per Acre
255 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

255 Duclair Dr, Winchester, KY 40391
/79
$849,900 Sold May 23, 2025
- 3,818 Sq Ft
- $223/SF
- 55 Days On Market
- 5 Beds
- 3.5 Baths
- Built 2001
3714 Wades Mill Rd, Winchester, KY 40391

Experience country living at FINEST in this immaculate 5-bedroom, 3.5-bath home on 11 acres, complete with two ponds and black plank fencing. The property includes an 864 SF horse barn with (2) 12x12 stalls, a tack area, and loft, along with a 1200 SF insulated equipment building. Inside, the 3800 SF home features soaring ceilings, large windows for panoramic views, and a great

Nora Williams Keller Williams Commonwealth

3714 Wades Mill Rd, Winchester, KY 40391

/41
Est $207,458 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 1,850 Sq Ft
15 Mackay Ave, Winchester, KY 40391

15 Mackay Ave, Winchester, KY 40391

/2
$100,000
- Land
- 1.1 Acres
- $90,909 per Acre
270 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

270 Duclair Dr, Winchester, KY 40391
/37
$149,900 Sold May 23, 2025
- 920 Sq Ft
- $163/SF
- 68 Days On Market
- 2 Beds
- 1 Bath
- Built 1950
502 N Maple St, Winchester, KY 40391

First Time Homebuyers, here is your opportunity to take advantage of Welcome Home Funds and make the move from renting to owning and investing in your future financial freedom! Check out this adorable 2 bedroom 1 bath home all on one level with an open kitchen and dining area. This home comes with plenty of storage in the 340 plus square foot metal building that has recently had electric added in

Christa Joynt Keller Williams Commonwealth

502 N Maple St, Winchester, KY 40391

/35
Est $302,870 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,769 Sq Ft
8 French Ave, Winchester, KY 40391

8 French Ave, Winchester, KY 40391

/2
$110,000
- Land
- 0.5 Acre
- $220,000 per Acre
260 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

260 Duclair Dr, Winchester, KY 40391
/37
$207,000 Sold May 23, 2025
- 1,120 Sq Ft
- $185/SF
- 41 Days On Market
- 3 Beds
- 2 Baths
- Built 1974
632 Laura Dr, Winchester, KY 40391

Discover the perfect blend of comfort and convenience in this charming 3-bedroom home, nestled in a sought-after neighborhood. Boasting a spacious fenced-in backyard, it's an ideal retreat for privacy and outdoor enjoyment. This gem offers a harmonious balance of community feel and personal sanctuary. Welcome to your dream home where memories await!'

Dale Hatton Dream Maker Realty, LLC

632 Laura Dr, Winchester, KY 40391

/71
Est $317,335 Not Listed For Sale
- 4 Beds
- 2 Baths
- 3,402 Sq Ft
16 French Ave, Winchester, KY 40391

16 French Ave, Winchester, KY 40391

/2
$110,000
- Land
- 0.32 Acre
- $343,750 per Acre
250 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

250 Duclair Dr, Winchester, KY 40391
/82
$275,000 Sold May 23, 2025
- 2,994 Sq Ft
- $92/SF
- 202 Days On Market
- 4 Beds
- 3 Baths
- Built 1920
111 S Burns Ave, Winchester, KY 40391

Reduced for quick sale!! Don't miss out on your opportunity to own a 100+ year old home located near historic downtown Winchester, KY. The detail and charm located within the walls of this 2 story craftsman are what many dream of. Tall ceilings, fireplaces, in almost evey room, beautiful original wood work is abundant as you enter from the quintessential front porch that's perfect for casual

Melodie Lincavage RE/MAX Elite Realty

111 S Burns Ave, Winchester, KY 40391

/41
Est $252,155 Not Listed For Sale
- 4 Beds
- 2 Baths
- 3,395 Sq Ft
254 S Highland St, Winchester, KY 40391

254 S Highland St, Winchester, KY 40391

/2
$110,000
- Land
- 0.34 Acre
- $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
/31
$194,000 Sold May 22, 2025
- 1,352 Sq Ft
- $143/SF
- 3 Days On Market
- 2 Beds
- 2.5 Baths
- Built 2004
429 Paisley Ct, Winchester, KY 40391

Excellent Townhome ready for you to move in! Great location, 2 Primary Bedrooms, 2 Full Bathrooms, and one 1/2 Bathroom! Fenced in yard, Spacious Deck, One Car attached Garage! Call today to schedule your showing!

Whitney Ensor Ensor Real Estate, LLC

429 Paisley Ct, Winchester, KY 40391

/70
Est $187,531 Not Listed For Sale
- 2 Beds
- 1 Bath
- 3,120 Sq Ft
107 Jefferson St, Winchester, KY 40391

107 Jefferson St, Winchester, KY 40391

/2
$110,000
- Land
- 0.38 Acre
- $289,474 per Acre
200 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

200 Duclair Dr, Winchester, KY 40391
/44
$225,000 Sold May 22, 2025
- 1,790 Sq Ft
- $126/SF
- 0 Days On Market
- 4 Beds
- 2 Baths
- Built 1979
308 Vaught Ct Unit A & B, Winchester, KY 40391

Investor's Dream! All-Brick Duplex Fully Rented & Priced Below Appraisal! This all-brick duplex is the perfect addition to your investment portfolio! Featuring a brand new roof, this property is fully occupied with great tenants already in place.Side A is a 2 bed 1 bath unit with fireplace.Side B is a 2 bed 1 bath unit on a basement.Washer dryer hook ups in both units.Located

Kim Buckner EXP Realty, LLC

308 Vaught Ct Unit A & B, Winchester, KY 40391

/33
Est $264,498 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,544 Sq Ft
144 E Broadway St, Winchester, KY 40391

144 E Broadway St, Winchester, KY 40391

/2
$150,000
- Land
- 2.11 Acres
- $71,090 per Acre
125 Knox Ct, 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

125 Knox Ct, Winchester, KY 40391
/35
$248,000 Sold May 22, 2025
- 1,773 Sq Ft
- $140/SF
- 20 Days On Market
- 3 Beds
- 2 Baths
- Built 1997
206 Moss Cir, Winchester, KY 40391

This 3 bedroom 2 bathroom home is located in the established Spring Hill Subdivision. Separate Utility/Mud room and one car garage. Two very spacious full bathrooms. Covered front porch creates nice space for relaxing. The rear patio overlooks a nice fenced in back yard with storage building. Roof shingles replaced in 2022.

David Baesler Kentucky Dreams Realty

206 Moss Cir, Winchester, KY 40391

/8
Est $155,728 Not Listed For Sale
- 2 Beds
- 1 Bath
- 984 Sq Ft
12 Buckner St, Winchester, KY 40391

12 Buckner St, Winchester, KY 40391

/2
$150,000
- Land
- 2.16 Acres
- $69,444 per Acre
120 Knox Ct, 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

120 Knox Ct, Winchester, KY 40391
/2
$366,363 Sold May 22, 2025
- 2,269 Sq Ft
- $161/SF
- 162 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2024
140 Gibson Way, Winchester, KY 40391

This Haywood Park is framed and at plumbing stage, is part of the Trend Collection by Ball Homes. It's a two story plan on a walk-out basement with plenty of room to grow! When you walk through the front door, you're greeted with a versatile flex space then down the hall opens up to the large living room and spacious kitchen. Cozy up next to the fireplace or sip your morning coffee outside on

Neshia Gaines Christies International Real Estate Bluegrass

140 Gibson Way, Winchester, KY 40391

/48
Est $333,536 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,068 Sq Ft
23 Boone Ave, Winchester, KY 40391

23 Boone Ave, Winchester, KY 40391

/2
$110,000
- Land
- 0.29 Acre
- $379,310 per Acre
160 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

160 Duclair Dr, Winchester, KY 40391

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