Newest Homes for Sale in Winchester, KY

• 

  

  

  /32

  $199,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  32 Jackson St, Winchester, KY 40391

  This beautiful home is located just minutes from historic downtown Winchester. It has 3 spacious bedrooms and 1 full bath. The home has a new roof. When you walk out back you will find an oversized garage. The huge backyard is all fenced in. Make an appointment to tour this one before it's gone.

  Dale Hatton Dream Maker Realty, LLC

  32 Jackson St, Winchester, KY 40391
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• 

  

  

  /4

  $389,900

  • 9 Beds
  • 6 Baths
  • 1,116 Sq Ft

  341 Carolina Ave, Winchester, KY 40391

  Exceptional investment opportunity! This fully occupied triplex is a turnkey addition to any investment portfolio, offering three spacious units, each with approximately 1,116 square feet, 3 bedrooms, and 1.5 bathrooms. With strong rental potential and separately metered utilities paid by the tenants, this property provides an excellent income-producing opportunity. Each unit features a

  Erin Lewis Christies International Real Estate Bluegrass

  341 Carolina Ave, Winchester, KY 40391
• 

  

  

  /19

  $189,000

  $20K PRICE DROP

  • Land
  • 41.69 Acres
  • $4,534 per Acre

  2697 Pine Ridge Rd, Winchester, KY 40391

  Escape to your own private retreat with this stunning 41.6± acre wooded tract nestled in the scenic countryside of Winchester, Kentucky. This expansive property offers a rare opportunity to own a secluded slice of nature, perfect for a private estate, recreational getaway, or hunting retreat. With rich with mature timber, this land presents a lot of natural beauty. A network of cleared trails and

  Derek Blankenship Keller Williams Commonwealth

  2697 Pine Ridge Rd, Winchester, KY 40391
• 

  

  

  /40

  $498,000

  Open House 9/13

  • 4 Beds
  • 2.5 Baths
  • 2,496 Sq Ft

  1780 Stoner Ephesus Rd, Winchester, KY 40391

  Discover the perfect blend of privacy, comfort, and country elegance on nearly 6 acres of beautiful Kentucky land. This stunning 4 bedroom, 2.5 bath home offers the lifestyle buyers dream of — complete with a sparkling inground pool, generous outdoor space, and thoughtful updates throughout. Set in a peaceful rural setting yet conveniently located just 8 minutes from the Winchester Bypass and 15

  Darrell Tackett Dream Maker Realty, LLC

  1780 Stoner Ephesus Rd, Winchester, KY 40391
• 

  

  

  /14

  $950,000

  • Land
  • 120 Acres
  • $7,917 per Acre

  345 Providence Ln, Winchester, KY 40391

  Rare opportunity to acquire approximately 120 acres of magnificent, rolling Bluegrass farmland in prime Clark County! This exceptionally versatile property features a ideal blend of cleared pasture and rich wooded land, making it perfectly suited for cattle, horses, recreational pursuits, or building your private dream estate.Equipped with a large pond, barn, and county water available at the

  Megan McCoy Keller Williams Legacy Group

  345 Providence Ln, Winchester, KY 40391
• 

  

  /12

  $495,000

  $34K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,054 Sq Ft

  443 Oxford Dr Unit 443,445,447,449, Winchester, KY 40391

  Don't miss this rare quadruplex opportunity in Winchester. Featuring four units (443, 445,447 and 449 Oxford Drive), this property is perfect for investors seeking multiple income streams in one location. Each unit offers a similar layout with approximately 1,054 ft, 2 bedrooms, and 1.5 baths. The photos shown are from one updated unit, and all units have comparable layouts—making this an ideal

  Tracey Goebel Tom Goebel & Company

  443 Oxford Dr Unit 443,445,447,449, Winchester, KY 40391
• 

  

  /27

  $380,000

  • 3 Beds
  • 2 Baths
  • 2,358 Sq Ft

  125 Amiens Blvd, Winchester, KY 40391

  Welcome to 125 Amiens Boulevard, where quality craftsmanship, thoughtful design, and everyday comfort come together in one exceptional home. Built by respected local builder Marcus Moore, this beautifully maintained all-brick ranch has been lovingly cared for and is truly move-in ready. From the moment you arrive, you'll appreciate the inviting curb appeal, spacious floor plan, and attention to

  Christina Hall ERA Select Real Estate

  125 Amiens Blvd, Winchester, KY 40391
• 

  

  /18

  $359,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,990 Sq Ft

  11 Stoney Brook Dr Unit 1, Winchester, KY 40391

  This three bedroom home has been updated, new painting interior and exterior, new flooring, new light fixtures, new bath vanities, new granite in kitchen plus much more. Owner/Broker

  Garry Milton Milton and Associates Real Estate

  11 Stoney Brook Dr Unit 1, Winchester, KY 40391
• 

  /2

  $195,000

  $2M PRICE DROP

  6699 Boonesboro Rd, Winchester, KY 40391

  READY TO BUILD OR HUNT? We have the perfect spot for you! Mostly wooded 8.35 acres, tract 2B, of green, treed, Bluegrass Heaven. Close proximity to I 75 and I 64 as well as Lexington, Richmond, and Winchester. Bring your own builder or we can help you find one!

  Jennifer Ray RE/MAX Elite Lexington

  6699 Boonesboro Rd, Winchester, KY 40391
• 

  

  /61

  $419,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,204 Sq Ft

  322 Calmes Blvd, Winchester, KY 40391

  Welcome to this superbly maintained home located in one of the area's most desirable neighborhoods. Offering 11 spacious rooms, this property delivers exceptional comfort, versatility, and charm. A beautiful front wrap around covered porch creates an inviting first impression, perfect for relaxing or greeting guests. The rear of the home features a covered back porch and an adjoining open deck,

  Darrell Tackett Dream Maker Realty, LLC

  322 Calmes Blvd, Winchester, KY 40391
• 

  

  /45

  $272,900

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  316 Buffalo Trace, Winchester, KY 40391

  Welcome home to this beautifully maintained 3 bedroom, 2 bath home offering comfort, style and fantastic outdoor living! The spacious two-car garage provides plenty of room for parking and storage, while the fully fenced backyard with a new privacy fence creates the perfect space to relax or entertain. Step outside to enjoy the inviting covered outdoor entertaining area, complete with lighting

  Emily Hacker-Todd CENTURY 21 Advantage Realty

  316 Buffalo Trace, Winchester, KY 40391
• 

  

  /55

  $410,000

  $5K PRICE INCREASE

  • 4 Beds
  • 2 Baths
  • 3,306 Sq Ft

  351 Boone Ave, Winchester, KY 40391

  Classic Williamsburg inspired home with charming dormers, timeless character, and an exceptional location that's a short walk to historic downtown Winchester. This spacious 4-bedroom , 2 bath home offers a flexible floor plan with 2 main-level bedrooms and a full bath, plus two additional bedrooms and a full bath upstairs. Enjoy elegant formal living and dining rooms, a large home office, and a

  Jim Woodrum RE/MAX Creative, Winchester

  351 Boone Ave, Winchester, KY 40391
• 

  

  /127

  $3,450,000

  • 2 Beds
  • 2.5 Baths
  • 2,725 Sq Ft

  510 - 612 Quisenberry Ln, Winchester, KY 40391

  Adjoining the banks of the Lower Howard's Creek in Clark County lies a very special 145.6± acre farm. With some of the oldest settlements in the county, this region near the Old Stone Church (or Old Providence Church) is immensely historic. Daniel Boone's first eleven surveys in Kentucky were conducted for the Bush family, early inhabitants of the area and farm. With gated stone entrances and

  Zach Davis Kirkpatrick & Company

  510 - 612 Quisenberry Ln, Winchester, KY 40391
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  /52

  $429,000

  Open Sun 1PM - 3PM $36K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,942 Sq Ft

  1024 Flanagan Station Rd, Winchester, KY 40391

  Nestled on 8.9 picturesque acres just off Boonesboro Road, this one-of-a-kind property offers the perfect blend of character, privacy, and endless potential. Whether you're dreaming of a horse farm, hobby farm, or simply room to roam, this beautiful property provides plenty of space for horses, livestock, gardening, or enjoying peaceful country living. Inside, you'll find a spacious open-concept

  Brooke Martin RO&CO Real Estate

  1024 Flanagan Station Rd, Winchester, KY 40391
• 

  

  /4

  $64,900

  • Land
  • 27,878 Sq Ft
  • $101,406 per Acre

  102 Royal Oak Dr, Winchester, KY 40391

  One of the Few Remaining Estate Homesites in Royal Oaks Estates! An exceptional opportunity awaits to build your custom dream home in the Estate Section of Royal Oaks, one of Clark County's most established and desirable communities. Situated on 0.64 acres, 102 Royal Oak Drive offers the space, setting, and flexibility to create a home tailored to your lifestyle while enjoying the beauty and

  

  Melia Hord

  MELIA Realty LLC

  102 Royal Oak Dr, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 9,600 Sq Ft
  • $356,171 per Acre

  235 Plantations Dr Unit LOT 4, Winchester, KY 40391

  Welcome to DEERLAWN at Royal Oaks—Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #4 is now available and ready for you to bring your own builder and create the home you've

  

  Melia Hord

  MELIA Realty LLC

  235 Plantations Dr Unit LOT 4, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 9,600 Sq Ft
  • $356,171 per Acre

  231 Plantations Dr Unit LOT 2, Winchester, KY 40391

  Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #2 is now available and ready for you to bring your own builder and create the home you've

  

  Melia Hord

  MELIA Realty LLC

  231 Plantations Dr Unit LOT 2, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 9,600 Sq Ft
  • $356,171 per Acre

  241 Plantations Dr Unit LOT 7, Winchester, KY 40391

  Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #7 is now available and ready for you to bring your own builder and create the home you've

  

  Melia Hord

  MELIA Realty LLC

  241 Plantations Dr Unit LOT 7, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 9,600 Sq Ft
  • $356,171 per Acre

  229 Plantations Dr Unit LOT 1, Winchester, KY 40391

  **Welcome to DEERLAWN at Royal Oaks—Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #1** is now available and ready for you to bring your own builder and create

  

  Melia Hord

  MELIA Realty LLC

  229 Plantations Dr Unit LOT 1, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 9,600 Sq Ft
  • $356,171 per Acre

  237 Plantations Dr Unit LOT 5, Winchester, KY 40391

  **Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #5** is now available and ready for you to bring your own builder and create

  

  Melia Hord

  MELIA Realty LLC

  237 Plantations Dr Unit LOT 5, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 9,600 Sq Ft
  • $356,171 per Acre

  233 Plantations Dr Unit LOT 3, Winchester, KY 40391

  Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community. Now offering the first 12 fully buildable homesites in Phase One, this is your opportunity to secure one of the very first lots in what is poised to become Winchester's premier new residential community. Lot #3 is now available and ready for you to bring your own builder and create the home you've

  

  Melia Hord

  MELIA Realty LLC

  233 Plantations Dr Unit LOT 3, Winchester, KY 40391
• 

  /2

  $78,500

  • Land
  • 9,600 Sq Ft
  • $356,171 per Acre

  239 Plantations Dr Unit LOT 6, Winchester, KY 40391

  **Welcome to DEERLAWN at Royal Oaks--Clark County's Newest Approved Single-Family Home Community.** Now offering the **first 12 fully buildable homesites** in **Phase One**, this is your opportunity to secure one of the very first lots in what is poised to become **Winchester's premier new residential community**. **Lot #6** is now available and ready for you to bring your own builder and create

  

  Melia Hord

  MELIA Realty LLC

  239 Plantations Dr Unit LOT 6, Winchester, KY 40391
• 

  

  /64

  $524,900

  • 3 Beds
  • 2.5 Baths
  • 2,514 Sq Ft

  275 Runnymeade Dr, Winchester, KY 40391

  OK! WOW!!! Location is yes, yes, yes! This house is located in a quiet residential neighborhood and in minutes you can be at the I-64 or I-75 interstate corridors. OK enough about location. This house is pristine! The owners have improved the property with new dimensional style roof shingles in 2025 along with new gutters. They have freshly painted the interior. They have added a new

  Craig Bridgewater Bridgewater Real Estate

  275 Runnymeade Dr, Winchester, KY 40391
• 

  

  /12

  $239,000

  $116K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,072 Sq Ft

  1128 Dale Dr, Winchester, KY 40391

  Duplex. Both units are being sold together. Great income-producing potential. Each side offers a nice sized vaulted Great room that opens to the kitchen, 2 bedrooms, 1.5 baths, a laundry room, and a 1-car garage. Nice private backyard for side with lots of trees. 1130 has a new HVAC. Selling As Is Inspections Welcome.

  Brian Hatfield Coldwell Banker McMahan

  1128 Dale Dr, Winchester, KY 40391
• 

  

  /37

  $259,000

  $37K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft

  33 Bon-Haven Ave, Winchester, KY 40391

  Welcome home to this beautifully renovated home in the desirable Bon Haven subdivision! From the moment you step inside, you'll appreciate the bright and inviting living room that flows seamlessly into the updated kitchen, creating a warm and functional space for everyday living. The main level features two spacious bedrooms and two full bathrooms, while the second floor offers a private third

  Erika Beatty Plum Tree Realty

  33 Bon-Haven Ave, Winchester, KY 40391
• 

  

  /64

  $420,000

  • 3 Beds
  • 2 Baths
  • 2,027 Sq Ft

  187 Hawthorne Dr, Winchester, KY 40391

  Welcome to 187 Hawthorne Drive, a beautifully maintained brick home in one of Winchester's most sought-after neighborhoods. Offering convenient one-level living, this 3-bedroom, 2-bath home features an inviting open floor plan that's perfect for everyday living and entertaining. The spacious living room is anchored by a cozy natural gas fireplace with gas logs, creating a warm and welcoming

  

  Christa Joynt

  Keller Williams Commonwealth

  187 Hawthorne Dr, Winchester, KY 40391
• 

  

  /46

  $749,900

  • 3 Beds
  • 2.5 Baths
  • 2,735 Sq Ft

  2180 Big Stoner Rd, Winchester, KY 40391

  Welcome to peaceful country living on 7.14 beautiful acres in Winchester! Built in 2022, this custom one-level home offers 3 bedrooms, 2.5 bathrooms, and 2,735 square feet of thoughtfully designed living space. The open floor plan features hardwood flooring, a spacious great room with a gas fireplace, and a stylish kitchen with a large island and ample cabinetry. The split-bedroom layout provides

  

  Ashley Barreto

  Indigo & Co

  2180 Big Stoner Rd, Winchester, KY 40391
• 

  

  /35

  $309,900

  $10K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 2,082 Sq Ft

  128 Cherokee Dr, Winchester, KY 40391

  Welcome to 128 Cherokee Drive, where space, versatility, and convenience come together! This all-brick split-foyer home offers 5 bedrooms, 2 full bathrooms, and over 2,000 square feet of comfortable living space, making it ideal for growing families, multi-generational living, or anyone needing extra room. The main level features a bright and inviting living room, while the finished lower level

  

  Tyler Hurst

  Oak & Acre

  128 Cherokee Dr, Winchester, KY 40391
• 

  

  /21

  $225,000

  • 3 Beds
  • 3.5 Baths
  • 1,892 Sq Ft

  128 Abbeywood Ct, Winchester, KY 40391

  This beautifully maintained 3 bedroom, 3.5 bath townhouse offers the perfect blend of comfort, convenience, and low-maintenance living. Ideally situated in a desirable location, this spacious home features a functional floor plan with generous living areas, well appointed bedrooms, and a bathroom for each bedroom, providing comfort and privacy for family and guests alike. Enjoy the benefits of

  Judd Hisel ERA Select Real Estate

  128 Abbeywood Ct, Winchester, KY 40391
• 

  

  /50

  $229,900

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  491 Hidden Hills Way, Winchester, KY 40391

  Welcome home to this charming 3-bedrooms, 2-bath ranch perfectly situated in the heart of Winchester! Offering the convenience of one-level living, this inviting 1200 sq ft home combines comfort, functionality, and an unbeatable location. Primary bedroom is en suite and offers plenty of closet space. Additional 2-bedrooms and 1-bath provide plenty of space. Enjoy easy access to schools, shopping,

  ROBIN TRIMBLE HomeFirst Real Estate

  491 Hidden Hills Way, Winchester, KY 40391
• 

  

  /65

  $364,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,269 Sq Ft

  15 Moundale Ave, Winchester, KY 40391

  Welcome to this beautifully maintained all-brick home nestled in one of Winchester's most established and desirable neighborhoods. Offering over 2,200 square feet of living space, this 3-bedroom, 2-bath home blends timeless character with thoughtful updates. The main level features a spacious family room with a cozy fireplace, custom cabinetry and new granite countertops in the kitchen, and a

  Josh Wood Freedom Realty & Property Management

  15 Moundale Ave, Winchester, KY 40391
• 

  

  /29

  $219,900

  • Land
  • 23.83 Acres
  • $9,228 per Acre

  3686 Crowe Ridge Rd, Winchester, KY 40391

  Discover the possibilities with this unique dual-property offering at 3686 & 3688 Crowe Ridge Road. Enjoy the peace and privacy of a beautiful country setting with room to spread out and endless potential. Whether you're looking for a primary residence with additional living space, an investment opportunity, or housing for extended family, this property offers versatility that's hard to find.

  Josh Wood Freedom Realty & Property Management

  3686 Crowe Ridge Rd, Winchester, KY 40391
• 

  

  /84

  $1,500,000

  • 4 Beds
  • 3 Baths
  • 7,172 Sq Ft

  351 Benton Rd, Winchester, KY 40391

  Welcome to a truly one-of-a-kind Kentucky estate where luxury, craftsmanship, and country living come together on 27 breathtaking acres in Clark County—just 10 minutes from the interstate for an easy commute while still enjoying complete privacy. Built with exceptional quality and thoughtfully designed by its original owner, this custom home offers over 7,000 square feet of living space with 4

  Darienne Hensley Keller Williams Legacy Group

  351 Benton Rd, Winchester, KY 40391
• 

  

  /41

  $225,000

  $10K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,609 Sq Ft

  120 Windsor Dr, Winchester, KY 40391

  Nestled in a well-established neighborhood filled with charm and character, this inviting all-brick home offers the warmth and comfort you've been looking for. Featuring 4 bedrooms and 1 bath, the thoughtfully designed layout includes a primary bedroom and second bedroom on the main floor, with two additional bedrooms upstairs, providing flexibility for family, guests, or a home office. Beautiful

  Cathie Witt-Pyle Keller Williams Commonwealth

  120 Windsor Dr, Winchester, KY 40391
• 

  

  /30

  $299,900

  $15K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,840 Sq Ft

  209 Connie Ln, Winchester, KY 40391

  Very motivated sellers, Get here first, make an offer on this 4 bedroom, 3 bath, 1 1/2 story home, 2 car garage, showroom fresh condition, vaulted ceiling, hardwood floors, tile, carpet, deck, nice back yard, call today to view.

  Mila Ensor Ensor Real Estate, LLC

  209 Connie Ln, Winchester, KY 40391
• 

  

  /4

  $159,000

  $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,472 Sq Ft

  13 Maryland Ave, Winchester, KY 40391

  Welcome Home! Located across the street from a park with walking trails and 2 dog runs, this home is ready for a new owner. Featuring 2 bedrooms on the first floor and an optional 3rd bedroom or bonus room in the partially finished attic space. The original hardwood floors are located throughout the home. VA assumable loan with a 2.99% interest rate - you can't beat that in today's market! Home

  Clay David Sutherland ERA Select Real Estate

  13 Maryland Ave, Winchester, KY 40391
• 

  

  /65

  $379,000

  Open Sun 2PM - 4PM $41K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,978 Sq Ft

  107 Hibiscus Ln, Winchester, KY 40391

  Welcome to 107 Hibiscus, where thoughtful updates, quality craftsmanship, and exceptional maintenance come together in this spacious 4-bedroom, 2.5-bath home. Offering a versatile floor plan with generous living spaces, this move-in-ready property has benefited from approximately nearly $70,000 in improvements over the past several years, providing peace of mind and modern finishes throughout.

  

  Christa Joynt

  Keller Williams Commonwealth

  107 Hibiscus Ln, Winchester, KY 40391
• 

  

  /31

  $89,900

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft

  308 Market St, Winchester, KY 40391

  Newly built and ready for its first owner, this 2-bedroom, 2-bathroom home in Quick Shop delivers the layout and finishes most buyers want without the price tag of new site-built construction. The main living area opens directly into the kitchen, giving the space a connected, airy feel that suits quiet evenings and gatherings alike. Down the hall, 2 bedrooms are sized for real furniture and real

  Hailey Blaylock Quick Shop MHC

  308 Market St, Winchester, KY 40391
• 

  

  /9

  $500,000

  $100K PRICE DROP

  • Land
  • 1.52 Acres
  • $328,947 per Acre

  1005 Early Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat-buyer to verify, zoned B-3. 1.52 acres located at I-64 exit 96, Right in front of the Hampton Inn, buyer to verify and satisfy themselves to all aspects and information on property. and inspections sold as is. Buyer to Check with all utilities companies to very water electric and gas availability and locations on all utilities.

  Whitney Ensor Ensor Real Estate, LLC

  1005 Early Dr, Winchester, KY 40391
• 

  

  /7

  $270,000

  $50K PRICE DROP

  • Land
  • 36,590 Sq Ft
  • $321,429 per Acre

  800 Interstate Dr, Winchester, KY 40391

  Visibility, Access, Utilities on site per seller/per plat buyer to verify, zoned B-3. .84 acres located and visible at I-64 exit 96, buyer to verify and satisfy themselves to all aspects and information on property and or inspections sold as is. Buyer to verify water, gas, and electric locations and availability.

  Whitney Ensor Ensor Real Estate, LLC

  800 Interstate Dr, Winchester, KY 40391

Showing Results 41 - 80, Page 2 of 6