Winchester, KY Luxury Homes for Sale and Real Estate

Winchester, KY Luxury Homes for Sale and Real Estate

Sort:

26 Results

131 TEAL LN, WINCHESTER, KY 40391 - Image f1503217cda3184a8e91373357ea5aff/3567148342

New Listing

131 TEAL LNWINCHESTER, KY 40391

$617,000

3

4

4,848 SQ FT

Listing Broker: Power House Realty

MLS® #: 26028684

5825 COMBS FERRY RD, WINCHESTER, KY 40391 - Image 86688898d331b31e23b68a9258a4b52f/1178675044

New Listing

5825 COMBS FERRY RDWINCHESTER, KY 40391

$4,895,000

3

4

5,800 SQ FT

Listing Broker: Bluegrass Sotheby's International Realty

MLS® #: 26028325

5039 COMBS FERRY RD, WINCHESTER, KY 40391 - Image fffe998236776cac94c24b8aeac9917b/25834932

New Listing

Virtual Tour

5039 COMBS FERRY RDWINCHESTER, KY 40391

$2,299,000

5

4

8,389 SQ FT

Listing Broker: Bluegrass Sotheby's International Realty

MLS® #: 26028074

9930 MOUNT STERLING RD, WINCHESTER, KY 40391 - Image 80f157d9359dd1fc6c1f0e3d3c60a796/419071148

New Listing

9930 MOUNT STERLING RDWINCHESTER, KY 40391

$639,000

3

1

1,962 SQ FT

Listing Broker: Dream Maker Realty, Llc

MLS® #: 26027905

2100 IRVINE RD # 40391, WINCHESTER, KY 40391 - Image 6b7ff4ef4e70a1cc325d717b62331021/431971800

New Listing

2100 IRVINE RD # 40391WINCHESTER, KY 40391

$1,125,000

3

4

3,672 SQ FT

Listing Broker: United Real Estate Bluegrass

MLS® #: 26026878

330 SPENCER LN, WINCHESTER, KY 40391 - Image d82714b90c68d9bd25d97f519e34cbf8/293889642

3D Virtual Tour

330 SPENCER LNWINCHESTER, KY 40391

$769,900

3

3

2,200 SQ FT

Listing Broker: Keller Williams Legacy Group

MLS® #: 26026365

1255 THE RIDINGS RD, WINCHESTER, KY 40391 - Image c647521d75064dfbd14b740c6fefbdc5/3392977256

Pending

1255 THE RIDINGS RDWINCHESTER, KY 40391

$775,000

6

4

3,789 SQ FT

Listing Broker: United Real Estate Bluegrass

MLS® #: 26026145

4578 COMBS FERRY RD, WINCHESTER, KY 40391 - Image edc3f02d6850e60b2dbb61e794e9ddf3/25016024

4578 COMBS FERRY RDWINCHESTER, KY 40391

$1,500,000

3

2

1,860 SQ FT

Listing Broker: The Agency

MLS® #: 26025528

104 TEAL LN, WINCHESTER, KY 40391 - Image aff0fceeb433d4a607a1db48340ef91a/393073480

104 TEAL LNWINCHESTER, KY 40391

$629,000

5

4

5,011 SQ FT

Listing Broker: Remax Elite Realty

MLS® #: 26023607

1400 CRAIG XING, WINCHESTER, KY 40391 - Image f03591e99e8e1175cb71d171eb54b275/3927325663

1400 CRAIG XINGWINCHESTER, KY 40391

$1,400,000

4

4

5,613 SQ FT

Listing Broker: Coldwell Banker Mcmahan

MLS® #: 26023265

132 LANA LN, WINCHESTER, KY 40391 - Image 499ff81c11ec6b6ef08b7740df4911f2/557562499

Pending

132 LANA LNWINCHESTER, KY 40391

$699,000

4

5

4,255 SQ FT

Listing Broker: Napier Realtors

MLS® #: 26022150

217 WADES MILL RD, WINCHESTER, KY 40391 - Image a55bc4651f894ff05204022ead451c79/483933914

217 WADES MILL RDWINCHESTER, KY 40391

$785,000

5

3

4,676 SQ FT

Listing Broker: Remax Creative Realty

MLS® #: 26019610

2180 BIG STONER RD, WINCHESTER, KY 40391 - Image 56795036a65edcfc3c30372dcada03ef/2669708141

Virtual Tour

2180 BIG STONER RDWINCHESTER, KY 40391

$749,900

3

3

2,735 SQ FT

Listing Broker: Indigo & Co

MLS® #: 26017698

8897 ROCKWELL RD, LEXINGTON, KY 40516 - Image 4308d229d6147b3a575815e109c9ecda/79039617

Updated

8897 ROCKWELL RDLEXINGTON, KY 40516

$5,500,000

7

6

9,769 SQ FT

Listing Broker: Keller Williams Commonwealth

MLS® #: 26011667

3166 COLBY RD, WINCHESTER, KY 40391 - Image 24ba7559f08406f00d4f731549c54063/3012724531

Updated

3166 COLBY RDWINCHESTER, KY 40391

$1,595,000

3

3

4,518 SQ FT

Listing Broker: Coldwell Banker Mcmahan

MLS® #: 26011538

4664 LEXINGTON RD, WINCHESTER, KY 40391 - Image ffe742b87ee077ac4b6d344988f487f1/3267304897

4664 LEXINGTON RDWINCHESTER, KY 40391

$2,750,000

8

8

13,433 SQ FT

Listing Broker: Block + Lot Homes

MLS® #: 26009631

455 DAVIS LN, WINCHESTER, KY 40391 - Image bd625b7ce6d35cdd70e334593a70f0a3/1420866204

Updated

Virtual Tour

455 DAVIS LNWINCHESTER, KY 40391

$699,000

2

3

2,361 SQ FT

Listing Broker: Dream Maker Realty, Llc

MLS® #: 25507944

3049 IRONWORKS RD, WINCHESTER, KY 40391 - Image 1694085d224342be2370c0e74ea5928c/1701029849

Updated

3049 IRONWORKS RDWINCHESTER, KY 40391

$2,999,000

6

5

3,693 SQ FT

Listing Broker: Keller Williams Legacy Group

MLS® #: 25507353

425 ALEXIS WAY, WINCHESTER, KY 40391 - Image 03cbb1ee0e5167c1fe8ab5bdf8570d64/1108915092

425 ALEXIS WAYWINCHESTER, KY 40391

$785,000

4

3

2,476 SQ FT

Listing Broker: Keller Williams Commonwealth

MLS® #: 25000149

415 ALEXIS WAY, WINCHESTER, KY 40391 - Image a1b5383151f12df9fb9ae420d3796b76/2393398939

415 ALEXIS WAYWINCHESTER, KY 40391

$700,000

3

2

2,400 SQ FT

Listing Broker: Keller Williams Commonwealth

MLS® #: 24025582

106 BELLA SHAE WAY, WINCHESTER, KY 40391 - Image 3b5b20cdba41b905f97d2b932fc1ef5e/1662430465

106 BELLA SHAE WAYWINCHESTER, KY 40391

$645,000

4

3

2,526 SQ FT

Listing Broker: Keller Williams Commonwealth

MLS® #: 24025577

111 BELLA SHAE WAY, WINCHESTER, KY 40391 - Image 94eae85350b0bf22e06ece3a2ed909d3/1272912756

111 BELLA SHAE WAYWINCHESTER, KY 40391

$825,000

3

3

2,995 SQ FT

Listing Broker: Keller Williams Commonwealth

MLS® #: 24025579

422 ALEXIS WAY, WINCHESTER, KY 40391 - Image 412828dc81c33b23aae82687878ae975/734123531

422 ALEXIS WAYWINCHESTER, KY 40391

$635,000

4

3

2,537 SQ FT

Listing Broker: Keller Williams Commonwealth

MLS® #: 24025583

424 ALEXIS WAY, WINCHESTER, KY 40391 - Image 9ed700ba123928333e854fc8169e9601/1999324454

424 ALEXIS WAYWINCHESTER, KY 40391

$625,000

3

3

2,405 SQ FT

Listing Broker: Keller Williams Commonwealth

MLS® #: 24025584

Updated 3:54pm UTC- 8/27/2026

The data relating to real estate for sale on this website comes in part from the Internet Data Exchange (IDX) Program of ImagineMLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by IDX brokerage firms other than , are marked with the IDX logo or the IDX thumbnail logo and detailed information about them includes the name of the listing IDX brokers. Information deemed reliable but not guaranteed. Copyright © 2026 ImagineMLS. All Rights Reserved.