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New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75, Lexington, Richmond, shopping, churches, hospital and schools, pictures to follow as home is being constructed. Contingency is buyers house having a successful closing on or before 8/31

3 Beds ⋅ 2 Baths ⋅ 26022825 MLS

New Construction, come view, great house plan, ranch on a crawl space, 3 bedrooms, 2 bath, you will love this inviting neighborhood, plan shown on line could vary, this is a spec home, all the colors have been decided, fixtures, flooring, brick, siding, cabinets, countertops have been ordered, restrictions apply, no HOA, buyer to verify sq ft of home and lot. This home is close to I-64, I-75, Lexington, Richmond, shopping, churches, hospital and schools, pictures to follow as home is being constructed. Contingency is buyers house having a successful closing on or before 8/31

206 Jett Dr, Winchester

$215,000

Welcome to 3 Nunnelly Ct, Winchester, KY This charming 3-bedroom, 2-bathroom home offers comfortable living with several important updates already in place. Featuring a newer HVAC system and newer roof, this home provides peace of mind for its next owner while offering plenty of opportunity to make the space your own. Inside, you'll find a bright, inviting layout with fresh, neutral finishes, updated flooring, and plenty of natural light. The spacious living area features a classic brick fireplace, creating a warm focal point for relaxing or entertaining. The updated kitchen offers new white cabinetry, stainless steel appliances, subway tile backsplash, ample counter space, and new granite countertops. Both bathrooms have been updated with clean, modern finishes, including attractive tile work and contemporary fixtures. The home's three bedrooms provide flexibility for family, guests, a home office, or additional living space. Outside, enjoy a covered front porch and established, tree-lined surroundings that provide a private and welcoming setting. The rear of the property offers additional outdoor space and a detached storage/outbuilding area. Conveniently located in Winchester, this home combines a comfortable residential setting with easy access to local shopping, dining, schools, and major roadways. Whether you're looking for a primary residence or an investment opportunity, this well-maintained home is worth a look!

3 Beds ⋅ 2 Baths ⋅ 26022771 MLS

Welcome to 3 Nunnelly Ct, Winchester, KY This charming 3-bedroom, 2-bathroom home offers comfortable living with several important updates already in place. Featuring a newer HVAC system and newer roof, this home provides peace of mind for its next owner while offering plenty of opportunity to make the space your own. Inside, you'll find a bright, inviting layout with fresh, neutral finishes, updated flooring, and plenty of natural light. The spacious living area features a classic brick fireplace, creating a warm focal point for relaxing or entertaining. The updated kitchen offers new white cabinetry, stainless steel appliances, subway tile backsplash, ample counter space, and new granite countertops. Both bathrooms have been updated with clean, modern finishes, including attractive tile work and contemporary fixtures. The home's three bedrooms provide flexibility for family, guests, a home office, or additional living space. Outside, enjoy a covered front porch and established, tree-lined surroundings that provide a private and welcoming setting. The rear of the property offers additional outdoor space and a detached storage/outbuilding area. Conveniently located in Winchester, this home combines a comfortable residential setting with easy access to local shopping, dining, schools, and major roadways. Whether you're looking for a primary residence or an investment opportunity, this well-maintained home is worth a look!

3 Nunnelly Ct, Winchester

$160,000

Lovely one story home located minutes from downtown Winchester with large detached garage ans shed! This home as three bedrooms and one bath with covered porch and walled patio outside. The garage is equipped with large ares for parking and storage and also has its own kitchen. Don't let this one pass by. Come see TODAY!!! Note: This is an auction property. Please call agent for more info Buyer to verify all information including schools

3 Beds ⋅ 1 Baths ⋅ 26022678 MLS

Lovely one story home located minutes from downtown Winchester with large detached garage ans shed! This home as three bedrooms and one bath with covered porch and walled patio outside. The garage is equipped with large ares for parking and storage and also has its own kitchen. Don't let this one pass by. Come see TODAY!!! Note: This is an auction property. Please call agent for more info Buyer to verify all information including schools

24 Spring St, Winchester

$78,500

Well priced and well located, 16 Denny Avenue is conveniently located near Eugene Gay Splash Park, downtown Winchester, shopping and schools. Home features 1152 sq ft with 3 bedrooms, 1 full bath, eat in kitchen and living room. Enclosed porch is located on front of house. Upgrades include laminate flooring, ductless heating and cooling and roof. Property has been tenant occupied and is sold as is. No repairs.

3 Beds ⋅ 1 Baths ⋅ 26022585 MLS

Well priced and well located, 16 Denny Avenue is conveniently located near Eugene Gay Splash Park, downtown Winchester, shopping and schools. Home features 1152 sq ft with 3 bedrooms, 1 full bath, eat in kitchen and living room. Enclosed porch is located on front of house. Upgrades include laminate flooring, ductless heating and cooling and roof. Property has been tenant occupied and is sold as is. No repairs.

16 Denny Ave, Winchester

$249,000

Welcome home to this spacious, low-maintenance townhome offering 3 levels of living space in a well established neighborhood. Thoughtfully maintained, a 3 year old roof, with recently replaced windows. This home offers plenty of room to spread out while keeping everyday living comfortable and convenient. The main level features a generously sized kitchen and family room with plenty of space for entertaining or gathering with family and friends. The lower level adds even more flexibility with a bonus room that could serve as a home office, recreation room, workout space, or additional living area. Upstairs you'll find 3 bedrooms, 2 full bathrooms, and ample closet space throughout. Outside, enjoy a large backyard backing to green space, along with the convenience of a rear-facing garage and a neighborhood walking trail. Ideally located with quick access to I-64 and approximately 20 minutes from Lexington's Hamburg area, this home combines space, updates, low-maintenance living, and a convenient location in one inviting package. Schedule your private showing today!

3 Beds ⋅ 3 Baths ⋅ 26022409 MLS

Welcome home to this spacious, low-maintenance townhome offering 3 levels of living space in a well established neighborhood. Thoughtfully maintained, a 3 year old roof, with recently replaced windows. This home offers plenty of room to spread out while keeping everyday living comfortable and convenient. The main level features a generously sized kitchen and family room with plenty of space for entertaining or gathering with family and friends. The lower level adds even more flexibility with a bonus room that could serve as a home office, recreation room, workout space, or additional living area. Upstairs you'll find 3 bedrooms, 2 full bathrooms, and ample closet space throughout. Outside, enjoy a large backyard backing to green space, along with the convenience of a rear-facing garage and a neighborhood walking trail. Ideally located with quick access to I-64 and approximately 20 minutes from Lexington's Hamburg area, this home combines space, updates, low-maintenance living, and a convenient location in one inviting package. Schedule your private showing today!

127 Bay Hill Dr, Winchester

$265,000

Welcome home to 15 Kittison Drive! Perfectly blending classic 1960s character with modern convenience, this Winchester residence offers comfort, space, and an unbeatable location just one mile from I-64. Inside, you'll find three spacious bedrooms and two full bathrooms designed for effortless daily living. The versatile, light-filled layout includes a large living room, a functional kitchen, and a cozy den perfect for movie nights or a home office. Outside, unwind in the private screened-in patio attached to an impressive, oversized barn-style two-car garage, which features massive bonus storage space above. Don't miss your chance to own a piece of Winchester charm—schedule your tour today and make Kittison Drive your next chapter!

3 Beds ⋅ 2 Baths ⋅ 26022208 MLS

Welcome home to 15 Kittison Drive! Perfectly blending classic 1960s character with modern convenience, this Winchester residence offers comfort, space, and an unbeatable location just one mile from I-64. Inside, you'll find three spacious bedrooms and two full bathrooms designed for effortless daily living. The versatile, light-filled layout includes a large living room, a functional kitchen, and a cozy den perfect for movie nights or a home office. Outside, unwind in the private screened-in patio attached to an impressive, oversized barn-style two-car garage, which features massive bonus storage space above. Don't miss your chance to own a piece of Winchester charm—schedule your tour today and make Kittison Drive your next chapter!

15 Kittison Dr, Winchester

$140,000

Property includes a detached secondary structure, a 600 sq. ft., 1-bedroom, 1-bath. This structure offers potential for investment use. Property and secondary structure are being sold as-is. Buyer and buyer's agent to independently verify square footage, zoning, permitted use, occupancy requirements, and suitability for buyer's intended purpose.

2 Beds ⋅ 1 Baths ⋅ 26022182 MLS

Property includes a detached secondary structure, a 600 sq. ft., 1-bedroom, 1-bath. This structure offers potential for investment use. Property and secondary structure are being sold as-is. Buyer and buyer's agent to independently verify square footage, zoning, permitted use, occupancy requirements, and suitability for buyer's intended purpose.

108 Franklin Ave, Winchester

$229,500

NEW roof, NEW kitchen appliances, NEW deck, and more! Welcome to 527 Hidden Hills Way! Located on a quiet cul-de-sac, this renovated one level home is ready for you to move right in. Vaulted ceilings give an open and airy feel, while fresh paint throughout offers a neutral palette for any design style. The spacious kitchen includes plenty of oak cabinetry, a separate pantry, stainless steel appliances, and easy access to the backyard. Hardwood flooring extends from the living room to the hallway, and new carpet has been installed in the bedrooms. The large primary bedroom includes an updated ensuite bathroom. The new deck overlooks the private backyard, and the covered front porch offers the perfect spot to enjoy views of your peaceful, low traffic street. Conveniently located just minutes from downtown Winchester, schools, shopping, dining, and easy access to I-64, this home provides the best of both convenience and small town charm. Schedule your showing today!

3 Beds ⋅ 2 Baths ⋅ 26022078 MLS

NEW roof, NEW kitchen appliances, NEW deck, and more! Welcome to 527 Hidden Hills Way! Located on a quiet cul-de-sac, this renovated one level home is ready for you to move right in. Vaulted ceilings give an open and airy feel, while fresh paint throughout offers a neutral palette for any design style. The spacious kitchen includes plenty of oak cabinetry, a separate pantry, stainless steel appliances, and easy access to the backyard. Hardwood flooring extends from the living room to the hallway, and new carpet has been installed in the bedrooms. The large primary bedroom includes an updated ensuite bathroom. The new deck overlooks the private backyard, and the covered front porch offers the perfect spot to enjoy views of your peaceful, low traffic street. Conveniently located just minutes from downtown Winchester, schools, shopping, dining, and easy access to I-64, this home provides the best of both convenience and small town charm. Schedule your showing today!

527 Hidden Hills Way, Winchester

$280,000

Come see this beautiful 13-acre property in the Historic Boonesborough area of Clark County, offering peaceful country living with the convenience of being just minutes from Winchester, Richmond, and Lexington. The property features a 2-bedroom, 1-bath home with 1,344 sq. ft., surrounded by beautiful acreage with plenty of room for animals, recreation, gardening, or simply enjoying the outdoors. The home has new plumbing, as well as new wiring. A brand-new 30x40 metal garage on a concrete slab provides excellent space for vehicles, equipment, storage, or hobbies. An additional workshop area next to the garage offers even more room for projects and workspace. With 13 beautiful acres, usable land, new outbuildings, and a convenient location, this property offers a great opportunity to enjoy country living while staying close to town. Schedule your showing today!

2 Beds ⋅ 1 Baths ⋅ 26022030 MLS

Come see this beautiful 13-acre property in the Historic Boonesborough area of Clark County, offering peaceful country living with the convenience of being just minutes from Winchester, Richmond, and Lexington. The property features a 2-bedroom, 1-bath home with 1,344 sq. ft., surrounded by beautiful acreage with plenty of room for animals, recreation, gardening, or simply enjoying the outdoors. The home has new plumbing, as well as new wiring. A brand-new 30x40 metal garage on a concrete slab provides excellent space for vehicles, equipment, storage, or hobbies. An additional workshop area next to the garage offers even more room for projects and workspace. With 13 beautiful acres, usable land, new outbuildings, and a convenient location, this property offers a great opportunity to enjoy country living while staying close to town. Schedule your showing today!

405 Nick Ln, Winchester

$204,900

Beautiful 3-bedroom, 1-bath home located at the end of a quiet, well established neighborhood within walking distance to downtown Winchester. This home features hardwood floors, a versatile in home office or bonus room, and several recent upgrades including a new stove, microwave, refrigerator, cabinets, and HVAC (1 year old). The property offers a backyard with a storage shed, providing convenient space for tools and outdoor equipment. Its desirable location combines privacy with easy access to local shops, dining, and downtown community events. Call today for your private showing. Owner/Agent

3 Beds ⋅ 1 Baths ⋅ 26021864 MLS

Beautiful 3-bedroom, 1-bath home located at the end of a quiet, well established neighborhood within walking distance to downtown Winchester. This home features hardwood floors, a versatile in home office or bonus room, and several recent upgrades including a new stove, microwave, refrigerator, cabinets, and HVAC (1 year old). The property offers a backyard with a storage shed, providing convenient space for tools and outdoor equipment. Its desirable location combines privacy with easy access to local shops, dining, and downtown community events. Call today for your private showing. Owner/Agent

38 Mackay Ave, Winchester

$544,900

Welcome to this beautifully maintained modern home located in the highly sought-after Royal Oaks Estates, perfectly positioned on the edge of Winchester with quick access to shopping, dining, and more. From the moment you step inside, you'll be captivated by the soaring vaulted ceilings in the central great room--an impressive space filled with natural light and designed for both comfort and entertaining. The gourmet kitchen is a chef's dream, offering ample counter space, modern appliances, and a casual dining nook. Just off the kitchen, you'll find a spacious formal dining area, a private home office, and a first-floor primary suite tucked away for peace and privacy. Upstairs, a second primary suite provides additional flexibility--ideal for guests or multi-generational living--along with three more generously sized bedrooms and a full bath. Step outside through elegant French doors to a beautifully landscaped patio and garden area that backs up to a tranquil greenspace--perfect for morning coffee or evening gatherings. The covered front porch offers another peaceful spot to relax and enjoy the neighborhood.

5 Beds ⋅ 4 Baths ⋅ 26021642 MLS

Welcome to this beautifully maintained modern home located in the highly sought-after Royal Oaks Estates, perfectly positioned on the edge of Winchester with quick access to shopping, dining, and more. From the moment you step inside, you'll be captivated by the soaring vaulted ceilings in the central great room--an impressive space filled with natural light and designed for both comfort and entertaining. The gourmet kitchen is a chef's dream, offering ample counter space, modern appliances, and a casual dining nook. Just off the kitchen, you'll find a spacious formal dining area, a private home office, and a first-floor primary suite tucked away for peace and privacy. Upstairs, a second primary suite provides additional flexibility--ideal for guests or multi-generational living--along with three more generously sized bedrooms and a full bath. Step outside through elegant French doors to a beautifully landscaped patio and garden area that backs up to a tranquil greenspace--perfect for morning coffee or evening gatherings. The covered front porch offers another peaceful spot to relax and enjoy the neighborhood.

130 Winterberry Cir, Winchester

$226,900

Motivated Seller, just lowered the jprice, This is great space for the price, walk into a great room with firepalce, hardwood floors, dining area leads to enclosed sunporch, master suite with full bath on first floor, nice kitchen , large back yard, 2 bedrooms up with fill bath, semi finished basement, 1 car garage, don't miss out on this townhome in a great location

3 Beds ⋅ 2 Baths ⋅ 26021639 MLS

Motivated Seller, just lowered the jprice, This is great space for the price, walk into a great room with firepalce, hardwood floors, dining area leads to enclosed sunporch, master suite with full bath on first floor, nice kitchen , large back yard, 2 bedrooms up with fill bath, semi finished basement, 1 car garage, don't miss out on this townhome in a great location

106 Quail Ridge Rd, Winchester

$199,900

606 College Street is such a cute Winchester home, with more space than you might expect and so many thoughtful improvements already completed. This 2-bedroom, 1-bath ranch offers 1,154 square feet, a bright kitchen with a breakfast bar and newer appliances, an open living and dining area, and a renovated bathroom. New LVP flooring, fresh paint, light fixtures, and new kitchen and bathroom faucets were all added in 2025. The living room fireplace and original trim add so much character, while the enclosed laundry and mudroom gives you useful extra space. Downstairs, the full unfinished walk-up basement offers more than 1,000 square feet for storage, hobbies, or future possibilities. Outside, you'll find a fenced backyard, detached one-car garage, storage shed, and welcoming front porch. The seller reports the roof and HVAC are both under six years old. A wonderful home with charm, practical space, and a great Winchester location!

2 Beds ⋅ 1 Baths ⋅ 26021605 MLS

606 College Street is such a cute Winchester home, with more space than you might expect and so many thoughtful improvements already completed. This 2-bedroom, 1-bath ranch offers 1,154 square feet, a bright kitchen with a breakfast bar and newer appliances, an open living and dining area, and a renovated bathroom. New LVP flooring, fresh paint, light fixtures, and new kitchen and bathroom faucets were all added in 2025. The living room fireplace and original trim add so much character, while the enclosed laundry and mudroom gives you useful extra space. Downstairs, the full unfinished walk-up basement offers more than 1,000 square feet for storage, hobbies, or future possibilities. Outside, you'll find a fenced backyard, detached one-car garage, storage shed, and welcoming front porch. The seller reports the roof and HVAC are both under six years old. A wonderful home with charm, practical space, and a great Winchester location!

606 College St, Winchester

$60,000

This 2 bedroom 2 bath home is perfect for an investor or a family looking for a nice home. All new flooring throughout. New bathroom sinks and commodes. The home backs up to the community park. It is located just minutes from Hamburg or the Winchester Bypass.

2 Beds ⋅ 2 Baths ⋅ 26020744 MLS

This 2 bedroom 2 bath home is perfect for an investor or a family looking for a nice home. All new flooring throughout. New bathroom sinks and commodes. The home backs up to the community park. It is located just minutes from Hamburg or the Winchester Bypass.

546 Constitution Dr, Winchester

$249,000

PRICED TO SELL! 5.5% assumable mortgage! Highly Motivated Seller! 59 Hillcrest Dr, Winchester, KY 40391 3 Beds | 2 Baths | ~2,066 Total Sq Ft | Full Basement | Large Lot Attention buyers, DIYers, and investors: Don't miss this incredible value! The seller is highly motivated and ready to entertain offers, making this attractive ranch home priced to sell immediately with the oppurtunity to unlock instant equity! Key Highlights: Potential Mother-in-Law Suite: The fully finished, remodeled lower level includes a full bath, separate living area, dedicated laundry, its own entrance, and a non-conforming 4th bedroom (or ideal home office/hobby room)—offering the perfect layout for a mother-in-law suite, guest quarters, or independent living space. New HVAC! Original Hardwood Floors: Character and potential await! Classic original hardwood flooring runs through the main level, begging to be refinished to showcase its natural warmth and beauty. Expansive Yard Space: Enjoy outdoor freedom on a huge lot! Featuring a spacious, fully fenced back yard with endless possibilities for play, pets, or entertaining. Versatile Layout: Upstairs main-level living area combined with a versatile basement setup to suit any household's needs. Walk out basement provides seperate entrances to each level. Location & Value: Nestled in an established neighborhood in winchester, moments from GRC, and quick access to Lexington and Richmond! Opportunities with this much space, flexible living arrangements, and upside don't last long—bring all reasonable offers! Agent is owner.

4 Beds ⋅ 2 Baths ⋅ 26020680 MLS

PRICED TO SELL! 5.5% assumable mortgage! Highly Motivated Seller! 59 Hillcrest Dr, Winchester, KY 40391 3 Beds | 2 Baths | ~2,066 Total Sq Ft | Full Basement | Large Lot Attention buyers, DIYers, and investors: Don't miss this incredible value! The seller is highly motivated and ready to entertain offers, making this attractive ranch home priced to sell immediately with the oppurtunity to unlock instant equity! Key Highlights: Potential Mother-in-Law Suite: The fully finished, remodeled lower level includes a full bath, separate living area, dedicated laundry, its own entrance, and a non-conforming 4th bedroom (or ideal home office/hobby room)—offering the perfect layout for a mother-in-law suite, guest quarters, or independent living space. New HVAC! Original Hardwood Floors: Character and potential await! Classic original hardwood flooring runs through the main level, begging to be refinished to showcase its natural warmth and beauty. Expansive Yard Space: Enjoy outdoor freedom on a huge lot! Featuring a spacious, fully fenced back yard with endless possibilities for play, pets, or entertaining. Versatile Layout: Upstairs main-level living area combined with a versatile basement setup to suit any household's needs. Walk out basement provides seperate entrances to each level. Location & Value: Nestled in an established neighborhood in winchester, moments from GRC, and quick access to Lexington and Richmond! Opportunities with this much space, flexible living arrangements, and upside don't last long—bring all reasonable offers! Agent is owner.

59 Hillcrest Dr, Winchester

$289,900

Wow! Pack your belongings and get ready to move! Your dream house just hit the market and It is going to go quick. Imagine sitting on the back deck , sipping your favorite beverage while your children and pets play safely in this large fenced in back yard. Or set up your home theatre in the spacious finished basement. This home has so much to offer, very spacious with the primary bed room and bathroom on the main floor, cathedral ceiling , covered front porch, large basement garage facing the rear of the home. Home is very convenient to downtown area and I-64. Dont drag your feet this one wont be on the market long.

4 Beds ⋅ 3 Baths ⋅ 26020651 MLS

Wow! Pack your belongings and get ready to move! Your dream house just hit the market and It is going to go quick. Imagine sitting on the back deck , sipping your favorite beverage while your children and pets play safely in this large fenced in back yard. Or set up your home theatre in the spacious finished basement. This home has so much to offer, very spacious with the primary bed room and bathroom on the main floor, cathedral ceiling , covered front porch, large basement garage facing the rear of the home. Home is very convenient to downtown area and I-64. Dont drag your feet this one wont be on the market long.

428 Waycross Dr, Winchester

$529,900

Welcome to this beautifully designed 3-bedroom, 2.5-bath ranch in the highly sought-after Earlymeade subdivision, where comfort, style, and exceptional efficiency come together. This spacious one-story home offers an open, inviting floor plan highlighted by a stunning floor-to-ceiling stone fireplace that anchors the expansive great room. The well-appointed kitchen features granite countertops, abundant workspace, and flows seamlessly into the living area—perfect for everyday living and entertaining. Throughout the home, you'll appreciate having no carpet, providing a clean, modern look that's both stylish and easy to maintain. What truly sets this home apart is its impressive investment in energy efficiency. Enjoy year-round comfort with a geothermal heating and cooling system, while solar panels paired with a Tesla battery backup help reduce energy costs and provide added peace of mind during power outages. Start your mornings on the covered front porch and relax in the evenings on the covered back porch, overlooking a beautiful greenspace with no rear neighbors directly behind you. Offering the perfect blend of quality construction, modern finishes, and cutting-edge energy-saving technology, this exceptional ranch is a rare opportunity in one of Winchesters most desirable neighborhoods.

4 Beds ⋅ 3 Baths ⋅ 26019672 MLS

Welcome to this beautifully designed 3-bedroom, 2.5-bath ranch in the highly sought-after Earlymeade subdivision, where comfort, style, and exceptional efficiency come together. This spacious one-story home offers an open, inviting floor plan highlighted by a stunning floor-to-ceiling stone fireplace that anchors the expansive great room. The well-appointed kitchen features granite countertops, abundant workspace, and flows seamlessly into the living area—perfect for everyday living and entertaining. Throughout the home, you'll appreciate having no carpet, providing a clean, modern look that's both stylish and easy to maintain. What truly sets this home apart is its impressive investment in energy efficiency. Enjoy year-round comfort with a geothermal heating and cooling system, while solar panels paired with a Tesla battery backup help reduce energy costs and provide added peace of mind during power outages. Start your mornings on the covered front porch and relax in the evenings on the covered back porch, overlooking a beautiful greenspace with no rear neighbors directly behind you. Offering the perfect blend of quality construction, modern finishes, and cutting-edge energy-saving technology, this exceptional ranch is a rare opportunity in one of Winchesters most desirable neighborhoods.

267 Runnymeade Dr, Winchester

$385,000

Welcome to this one-owner home offering the perfect combination of space, thoughtful updates, and country living! Built in 1996 and situated on 1.67 beautiful acres, this well-maintained 3-bedroom, 2-bath home features 1,344 square feet of comfortable living space with numerous improvements already completed for its next owner. Inside, you'll find updated interior paint, durable LifeProof laminate flooring, beautiful hardwood flooring, and replacement windows (house windows installed in 2021). Pride of ownership is evident throughout, and the home has never had indoor pets. One of the standout features is the impressive 896-square-foot attached garage. With insulated walls, an oversized 8-foot-tall by 18-foot-wide garage door, and a freshly painted interior (2026), this space offers endless possibilities. Whether you need room for oversized vehicles, a workshop, hobbies, or even future finished living space, this garage provides exceptional flexibility. Outside, enjoy the spacious 1.67-acre lot from the newer concrete front porch with handrails and thoughtful landscaping with plenty of shade trees or relax on the concrete back patio added in 2024. The detached 330-square-foot tool shed is equipped with water, electricity, and a 220-volt RV hookup, making it ideal for projects, storage, or RV owners. Major improvements include: • New HVAC system (2009) • Roof replaced (2015) • Vinyl siding and new concrete front porch with handrails (2016) • Garage door opener replaced (2018) • New garage door springs (2020) • Replacement house windows (2021; garage windows excluded) • Updated interior paint and LifeProof laminate flooring (2023) • HVAC professionally serviced (2023) • New concrete back patio (2024) • Garage interior repainted (2026) • Termite treatment maintained and updated • Updated most of the exterior hardware If you've been searching for a move-in-ready home with acreage, a massive insulated garage, an equipped workshop, and a long history of meticulous maintenance by its original owner, this property deserves a place at the top of your list. Schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ 26020495 MLS

Welcome to this one-owner home offering the perfect combination of space, thoughtful updates, and country living! Built in 1996 and situated on 1.67 beautiful acres, this well-maintained 3-bedroom, 2-bath home features 1,344 square feet of comfortable living space with numerous improvements already completed for its next owner. Inside, you'll find updated interior paint, durable LifeProof laminate flooring, beautiful hardwood flooring, and replacement windows (house windows installed in 2021). Pride of ownership is evident throughout, and the home has never had indoor pets. One of the standout features is the impressive 896-square-foot attached garage. With insulated walls, an oversized 8-foot-tall by 18-foot-wide garage door, and a freshly painted interior (2026), this space offers endless possibilities. Whether you need room for oversized vehicles, a workshop, hobbies, or even future finished living space, this garage provides exceptional flexibility. Outside, enjoy the spacious 1.67-acre lot from the newer concrete front porch with handrails and thoughtful landscaping with plenty of shade trees or relax on the concrete back patio added in 2024. The detached 330-square-foot tool shed is equipped with water, electricity, and a 220-volt RV hookup, making it ideal for projects, storage, or RV owners. Major improvements include: • New HVAC system (2009) • Roof replaced (2015) • Vinyl siding and new concrete front porch with handrails (2016) • Garage door opener replaced (2018) • New garage door springs (2020) • Replacement house windows (2021; garage windows excluded) • Updated interior paint and LifeProof laminate flooring (2023) • HVAC professionally serviced (2023) • New concrete back patio (2024) • Garage interior repainted (2026) • Termite treatment maintained and updated • Updated most of the exterior hardware If you've been searching for a move-in-ready home with acreage, a massive insulated garage, an equipped workshop, and a long history of meticulous maintenance by its original owner, this property deserves a place at the top of your list. Schedule your private showing today!

2725 Goshen Rd, Winchester

$475,000

Back on the market at no fault of the sellers. Beautiful all brick ranch home on 4.1 acres that has 3 bedrooms, 2 bathrooms, open concept floor plan, large stone fireplace with wood burning stove & blower. Kitchen has butcher block countertops, garbage disposal, pot filler, range hood, ample cabinets with large pantry cabinet & island. Large primary suite that includes a walk-in tiled shower, with 2 shower heads, has a place for soaking tub with easy access for hooking up, 2 vanities, toilet closet and large closet with lots of built-in shelving. Easy access to laundry room which is right off of the garage and connects to primary suite. Family room has bar sink and overlooks a beautiful view of the secluded wooded backyard and has 3 French doors and 2 atrium doors to access back deck. Home has Pella windows and doors that are triple lock and Bryant Smart Home Wi-Fi thermostat & MyQ garage door opener app opens and closes garage door from anywhere. Large 2 car garage with mechanical room. Only 5 minutes from Mountain Parkway and 45 minutes to Toyota in Georgetown. Schedule your showing today!

3 Beds ⋅ 2 Baths ⋅ 26020298 MLS

Back on the market at no fault of the sellers. Beautiful all brick ranch home on 4.1 acres that has 3 bedrooms, 2 bathrooms, open concept floor plan, large stone fireplace with wood burning stove & blower. Kitchen has butcher block countertops, garbage disposal, pot filler, range hood, ample cabinets with large pantry cabinet & island. Large primary suite that includes a walk-in tiled shower, with 2 shower heads, has a place for soaking tub with easy access for hooking up, 2 vanities, toilet closet and large closet with lots of built-in shelving. Easy access to laundry room which is right off of the garage and connects to primary suite. Family room has bar sink and overlooks a beautiful view of the secluded wooded backyard and has 3 French doors and 2 atrium doors to access back deck. Home has Pella windows and doors that are triple lock and Bryant Smart Home Wi-Fi thermostat & MyQ garage door opener app opens and closes garage door from anywhere. Large 2 car garage with mechanical room. Only 5 minutes from Mountain Parkway and 45 minutes to Toyota in Georgetown. Schedule your showing today!

625 Pine Ridge Rd, Winchester

$189,000

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.

3 Beds ⋅ 1 Baths ⋅ 26020135 MLS

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.

32 Jackson St, Winchester

$498,000

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 minutes from Mt. Sterling, this property delivers the best of both worlds: tranquility and accessibility. From the inviting living spaces to the expansive grounds ideal for relaxing, entertaining, or simply enjoying the view, this home is truly one of a kind. Opportunities like this don't come often — this one will move fast. Don't miss your chance. Call today to schedule your private showing.

4 Beds ⋅ 3 Baths ⋅ 26019848 MLS

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 minutes from Mt. Sterling, this property delivers the best of both worlds: tranquility and accessibility. From the inviting living spaces to the expansive grounds ideal for relaxing, entertaining, or simply enjoying the view, this home is truly one of a kind. Opportunities like this don't come often — this one will move fast. Don't miss your chance. Call today to schedule your private showing.

1780 Stoner-Ephesus Rd, Winchester

443 Oxford Unit 443,445,447,449, Winchester

$495,000

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 setup for consistent rental demand. The vacant property (449) can be viewed through scheduling via showing time and sentrikey box is on the back door, the other 3 units are occupied and can be viewed with 48 hours notice given to the tenants.

2 Beds ⋅ 2 Baths ⋅ 26019713 MLS

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 setup for consistent rental demand. The vacant property (449) can be viewed through scheduling via showing time and sentrikey box is on the back door, the other 3 units are occupied and can be viewed with 48 hours notice given to the tenants.

443 Oxford Unit 443,445,447,449, Winchester

$355,000

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

3 Beds ⋅ 2 Baths ⋅ 26019263 MLS

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

11 Stoney Brook Dr Unit 1, Winchester

$275,000

Enjoy peaceful country living on this beautiful 2+ acre property featuring a nearly new manufactured home and a spacious barn. Surrounded by scenic countryside views, this property offers plenty of privacy, comfort, and room to enjoy the outdoors. The well-kept home provides a cozy place to relax, while the large barn and open space give you plenty of options for storage, hobbies, gardening, animals, or recreation. Take in quiet mornings, beautiful sunsets, and the charm of wide-open spaces while still being close to nearby amenities. A great opportunity to own a slice of the country and make it your own.

3 Beds ⋅ 2 Baths ⋅ 26019157 MLS

Enjoy peaceful country living on this beautiful 2+ acre property featuring a nearly new manufactured home and a spacious barn. Surrounded by scenic countryside views, this property offers plenty of privacy, comfort, and room to enjoy the outdoors. The well-kept home provides a cozy place to relax, while the large barn and open space give you plenty of options for storage, hobbies, gardening, animals, or recreation. Take in quiet mornings, beautiful sunsets, and the charm of wide-open spaces while still being close to nearby amenities. A great opportunity to own a slice of the country and make it your own.

4305 Old Boonesboro Rd, Winchester

$389,000

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, ideal for outdoor dining, entertaining, or enjoying peaceful evenings. An outbuilding provides valuable additional storage or workspace. Convenience is unmatched—you're just a few minutes from shopping, restaurants, golf courses, and the bypass, making daily living effortless while still enjoying the tranquility of a well established community. This home truly has so much to offer and is a must see for buyers seeking comfort, location, and lifestyle.

3 Beds ⋅ 3 Baths ⋅ 26019133 MLS

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, ideal for outdoor dining, entertaining, or enjoying peaceful evenings. An outbuilding provides valuable additional storage or workspace. Convenience is unmatched—you're just a few minutes from shopping, restaurants, golf courses, and the bypass, making daily living effortless while still enjoying the tranquility of a well established community. This home truly has so much to offer and is a must see for buyers seeking comfort, location, and lifestyle.

322 Calmes Blvd, Winchester

$379,000

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 bright Florida room overlooking established flower gardens. The spacious eat-in kitchen features abundant cabinetry, a butler's pantry, and plenty of room for family gatherings and entertaining. Beautiful original hardwood floors flow throughout much of the home. The main level bathroom showcases distinctive brick flooring, adding unique character. Custom window treatments and ceiling fans throughout the home are included. You will love the abundant storage throughout the home! Four walk-in closets, including one oversized space that could be used as a nursery or dressing area. The unfinished basement offers endless possibilities for additional living space, a workshop, or recreation and inclues a storm shelter for added peace of mind. This home is just minutes from I-64, country clubs, schools, shopping, dining and everyday conveniences. Combining classic Williamsburg architecture, generous living spaces and original details, this is a rare opportunity to own a truly special home.

4 Beds ⋅ 2 Baths ⋅ 26017258 MLS

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 bright Florida room overlooking established flower gardens. The spacious eat-in kitchen features abundant cabinetry, a butler's pantry, and plenty of room for family gatherings and entertaining. Beautiful original hardwood floors flow throughout much of the home. The main level bathroom showcases distinctive brick flooring, adding unique character. Custom window treatments and ceiling fans throughout the home are included. You will love the abundant storage throughout the home! Four walk-in closets, including one oversized space that could be used as a nursery or dressing area. The unfinished basement offers endless possibilities for additional living space, a workshop, or recreation and inclues a storm shelter for added peace of mind. This home is just minutes from I-64, country clubs, schools, shopping, dining and everyday conveniences. Combining classic Williamsburg architecture, generous living spaces and original details, this is a rare opportunity to own a truly special home.

351 Boone Ave, Winchester

$419,000

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 kitchen that flows into a stunning vaulted-ceiling living room, where a floor-to-ceiling rock fireplace creates a warm and inviting focal point. Expansive windows fill the home with natural light while framing beautiful views of the surrounding acreage. The thoughtfully designed layout features 3 bedrooms and 2 full bathrooms, including a private second-floor primary suite that offers a peaceful retreat from the rest of the home. Just off the back of the home, the sunroom is the perfect place to enjoy your morning coffee or relax while taking in the sunset over your property. The basement offers over 1,350 square feet of unfinished space and is already plumbed for an additional full bathroom, providing endless possibilities for future expansion. Whether you envision additional bedrooms, a second living area, a game room, home gym, or the ultimate entertaining space, it's ready for your personal touch. If you've been searching for a property that offers acreage, character, and room to grow, this rare opportunity is one you won't want to miss. Schedule your private showing today!

3 Beds ⋅ 2 Baths ⋅ 26018911 MLS

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 kitchen that flows into a stunning vaulted-ceiling living room, where a floor-to-ceiling rock fireplace creates a warm and inviting focal point. Expansive windows fill the home with natural light while framing beautiful views of the surrounding acreage. The thoughtfully designed layout features 3 bedrooms and 2 full bathrooms, including a private second-floor primary suite that offers a peaceful retreat from the rest of the home. Just off the back of the home, the sunroom is the perfect place to enjoy your morning coffee or relax while taking in the sunset over your property. The basement offers over 1,350 square feet of unfinished space and is already plumbed for an additional full bathroom, providing endless possibilities for future expansion. Whether you envision additional bedrooms, a second living area, a game room, home gym, or the ultimate entertaining space, it's ready for your personal touch. If you've been searching for a property that offers acreage, character, and room to grow, this rare opportunity is one you won't want to miss. Schedule your private showing today!

1024 Flanagan Station Rd, Winchester

$229,900

*NEW ROOF!* Welcome home to this well-maintained 3-bedroom, 2-bath brick ranch offering easy one-level living in a convenient location close to shopping, dining, parks, and the community pool. The spacious open family room flows into the kitchen, featuring bamboo wood flooring, a large granite island, newer stainless steel appliances, and a gas range—perfect for everyday living and entertaining. Step outside and enjoy your own Aurora above-ground pool, just in time for summer fun! The partially fenced backyard also includes an oversized storage/tool shed, providing plenty of room for hobbies and extra storage. Enjoy peace of mind with major updates, including a newer HVAC system, water heater, Window World windows (approximately 5 years old), and a new roof with a 5-year warranty. As an added bonus, the seller is offering up to a $2,500 flooring allowance with an acceptable offer. Please include the flooring allowance in any written offer. Don't miss the opportunity to make this inviting home yours!

3 Beds ⋅ 2 Baths ⋅ 26018492 MLS

*NEW ROOF!* Welcome home to this well-maintained 3-bedroom, 2-bath brick ranch offering easy one-level living in a convenient location close to shopping, dining, parks, and the community pool. The spacious open family room flows into the kitchen, featuring bamboo wood flooring, a large granite island, newer stainless steel appliances, and a gas range—perfect for everyday living and entertaining. Step outside and enjoy your own Aurora above-ground pool, just in time for summer fun! The partially fenced backyard also includes an oversized storage/tool shed, providing plenty of room for hobbies and extra storage. Enjoy peace of mind with major updates, including a newer HVAC system, water heater, Window World windows (approximately 5 years old), and a new roof with a 5-year warranty. As an added bonus, the seller is offering up to a $2,500 flooring allowance with an acceptable offer. Please include the flooring allowance in any written offer. Don't miss the opportunity to make this inviting home yours!

528 Estes Dr, Winchester

$524,900

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 refrigerator, stove, microwave and a washer and dryer. The owners have meticulously maintained this house throughout. From the entrance foyer note the gleaming wood flooring and the fresh paint on the 9' foot ceiling walls, the vaulted great room and the crown molding. The split bedroom concept is great for guests or a home office. And above the garage is a bonus room measuring 420 sq ft. Entertaining or relaxing on the covered back patio that overlooks the beautiful Kentucky Bluegrass is a must. And bonus, the property is adjacent to a church property that is mowed for a walking path. Make an appointment to see this house today, it may be your new home.

3 Beds ⋅ 3 Baths ⋅ 26018460 MLS

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 refrigerator, stove, microwave and a washer and dryer. The owners have meticulously maintained this house throughout. From the entrance foyer note the gleaming wood flooring and the fresh paint on the 9' foot ceiling walls, the vaulted great room and the crown molding. The split bedroom concept is great for guests or a home office. And above the garage is a bonus room measuring 420 sq ft. Entertaining or relaxing on the covered back patio that overlooks the beautiful Kentucky Bluegrass is a must. And bonus, the property is adjacent to a church property that is mowed for a walking path. Make an appointment to see this house today, it may be your new home.

275 Runnymeade Dr, Winchester

$249,000

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 bedroom; perfect for a guest room, home office, or primary retreat. The unfinished 780-square-foot basement provides endless possibilities for additional living space, a recreation room, or extra storage. Located within walking distance of the popular Legacy Grove Park, you'll enjoy easy access to walking trails, green space, and outdoor recreation. Move-in ready and thoughtfully renovated, this home is ready for its next owner. SELLER IS OFFERING A CREDIT FOR A 2-1 RATE BUYDOWN WITH AN ACCEPTED OFFER. ASK LISTING AGENT FOR MORE INFO!

3 Beds ⋅ 2 Baths ⋅ 26018346 MLS

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 bedroom; perfect for a guest room, home office, or primary retreat. The unfinished 780-square-foot basement provides endless possibilities for additional living space, a recreation room, or extra storage. Located within walking distance of the popular Legacy Grove Park, you'll enjoy easy access to walking trails, green space, and outdoor recreation. Move-in ready and thoughtfully renovated, this home is ready for its next owner. SELLER IS OFFERING A CREDIT FOR A 2-1 RATE BUYDOWN WITH AN ACCEPTED OFFER. ASK LISTING AGENT FOR MORE INFO!

33 Bon-Haven Ave, Winchester