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Prime investment opportunity in Winchester! This 4-plex offers four unique 2-bedroom, 1-bath units, each approximately 900 sqft, with washer/dryer hookups and kitchen appliances included. Tenants enjoy a quiet neighborhood setting just steps from College Park, close to the Public Library and downtown. Alley access for parking makes it feel private and secluded. Units feature wide hallways, mudroom entries, and varied layouts. One unit was recently fully renovated with LVP flooring throughout, a stone fireplace, and a dishwasher, while others offer partially covered parking or extra storage space. A double storage shed is on-site as well. This property delivers steady income and long-term potential!

8 Beds ⋅ 4 Baths ⋅ 25500496 MLS

Prime investment opportunity in Winchester! This 4-plex offers four unique 2-bedroom, 1-bath units, each approximately 900 sqft, with washer/dryer hookups and kitchen appliances included. Tenants enjoy a quiet neighborhood setting just steps from College Park, close to the Public Library and downtown. Alley access for parking makes it feel private and secluded. Units feature wide hallways, mudroom entries, and varied layouts. One unit was recently fully renovated with LVP flooring throughout, a stone fireplace, and a dishwasher, while others offer partially covered parking or extra storage space. A double storage shed is on-site as well. This property delivers steady income and long-term potential!

23 1/2 Wheeler Ave, Winchester

$290,000

This beautiful 1.5-story home offers all the charm of downtown in a small town, with a library, park, and restaurants nearby. Plus, just minutes to Lexington when the city is calling your name. This home has been remodeled for modern living, featuring an open floor plan. There is plenty of room for entertaining with a beautiful, well-equipped kitchen and a large island open to both the dining space and the living room. The first floor features all the luxuries, including a primary suite with an ensuite bathroom and a large walk-in closet, a dedicated laundry/mud room, and a powder room. Upstairs, you'll find two spacious bedrooms and an additional bathroom. The entertaining doesn't have to stop inside, as there is also a covered patio and a large fenced-in backyard ready for play. There's so much to this charmer, including a covered parking spot and an unfinished basement for additional storage.

3 Beds ⋅ 3 Baths ⋅ 26004053 MLS

This beautiful 1.5-story home offers all the charm of downtown in a small town, with a library, park, and restaurants nearby. Plus, just minutes to Lexington when the city is calling your name. This home has been remodeled for modern living, featuring an open floor plan. There is plenty of room for entertaining with a beautiful, well-equipped kitchen and a large island open to both the dining space and the living room. The first floor features all the luxuries, including a primary suite with an ensuite bathroom and a large walk-in closet, a dedicated laundry/mud room, and a powder room. Upstairs, you'll find two spacious bedrooms and an additional bathroom. The entertaining doesn't have to stop inside, as there is also a covered patio and a large fenced-in backyard ready for play. There's so much to this charmer, including a covered parking spot and an unfinished basement for additional storage.

322 S Burns Ave, Winchester

$280,000

Outstanding opportunity for investors or owner-occupants! This beautifully updated duplex is located in Winchester's desirable Stuarts Addition and offers two spacious units, each featuring approximately 1,545 square feet with 3 bedrooms and 2 full bathrooms. Both units have been thoughtfully renovated and feature hardwood flooring throughout the main living areas with tile in the wet areas for style and durability. Major improvements include newer HVAC systems, roof, stainless steel appliances, windows, doors, vinyl siding, and fresh interior paint, providing true move-in-ready convenience and low-maintenance ownership. Ideally located within walking distance of College Park and historic downtown Winchester, this property also offers quick access to I-64, shopping, restaurants, schools, and everyday amenities. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other, this well-maintained duplex offers the perfect combination of modern updates, strong income potential, and an exceptional location.

6 Beds ⋅ 4 Baths ⋅ 26019498 MLS

Outstanding opportunity for investors or owner-occupants! This beautifully updated duplex is located in Winchester's desirable Stuarts Addition and offers two spacious units, each featuring approximately 1,545 square feet with 3 bedrooms and 2 full bathrooms. Both units have been thoughtfully renovated and feature hardwood flooring throughout the main living areas with tile in the wet areas for style and durability. Major improvements include newer HVAC systems, roof, stainless steel appliances, windows, doors, vinyl siding, and fresh interior paint, providing true move-in-ready convenience and low-maintenance ownership. Ideally located within walking distance of College Park and historic downtown Winchester, this property also offers quick access to I-64, shopping, restaurants, schools, and everyday amenities. Whether you're looking to expand your investment portfolio or live in one unit while generating rental income from the other, this well-maintained duplex offers the perfect combination of modern updates, strong income potential, and an exceptional location.

21 Beckner St, Winchester

$235,000

All on one level, large master bedroom, HVAC less than 2 years old and upgrades made in the last year. Enjoy a private backyard fenced with trees behind. The fence, vinyl siding and gutters were all professionally cleaned last summer. New lighting and minor upgrades made to master bath. Overhead storage added to garage. Sensi thermostat for wifi control of heating and air. New keyless entry on front door. This is a great home with great neighbors. Only moving for job relocation.

3 Beds ⋅ 2 Baths ⋅ 25508586 MLS

All on one level, large master bedroom, HVAC less than 2 years old and upgrades made in the last year. Enjoy a private backyard fenced with trees behind. The fence, vinyl siding and gutters were all professionally cleaned last summer. New lighting and minor upgrades made to master bath. Overhead storage added to garage. Sensi thermostat for wifi control of heating and air. New keyless entry on front door. This is a great home with great neighbors. Only moving for job relocation.

142 Sturbridge Ln, Winchester

$165,000

WOW! great price adjustment on this one!!! Great opportunity to own this well loved home in a very convenient location in growing community of Winchester. Expensive updates have been done recently- roof, siding, main level LVP flooring, water heater and main water line replacement are all taken care of! Lots of character and charm upon entry into the entry foyer with nice staircase, opening to large living room with a lovely mantel. Spacious dining room with built in corner cabinet flows into kitchen with plenty of cabinetry and counter space. Large laundry room with access to rear yard. A partial bath completes main level. Upstairs has two spacious bedrooms and a full bath. Lots of closet space including a cedar closet. . Large lot ( over a quarter of an acre)with trees and space for kids to roam and explore. Great location near public library, within walking distance of downtown and popular College Park Facility. Come see this one!

3 Beds ⋅ 2 Baths ⋅ 26003334 MLS

WOW! great price adjustment on this one!!! Great opportunity to own this well loved home in a very convenient location in growing community of Winchester. Expensive updates have been done recently- roof, siding, main level LVP flooring, water heater and main water line replacement are all taken care of! Lots of character and charm upon entry into the entry foyer with nice staircase, opening to large living room with a lovely mantel. Spacious dining room with built in corner cabinet flows into kitchen with plenty of cabinetry and counter space. Large laundry room with access to rear yard. A partial bath completes main level. Upstairs has two spacious bedrooms and a full bath. Lots of closet space including a cedar closet. . Large lot ( over a quarter of an acre)with trees and space for kids to roam and explore. Great location near public library, within walking distance of downtown and popular College Park Facility. Come see this one!

334 S Burns Ave, Winchester

$135,000

This one is on the market for someone who loves to make this nice frame home new again, lots of hardwood floors, nice size rooms, as per seller upstairs has some plumbing for a 2nd bathroom, metal roof, house will need new HVAC, newer nice windows, deck overlooking back yard, The Upstairs is not finished, please be careful walking on the upstairs floor, would be a nice second bedroom and/or den if finished, call today! (Buyer to verify the size of home and size of Lot) Take caution when walking on upstairs floor.

3 Beds ⋅ 1 Baths ⋅ 26020511 MLS

This one is on the market for someone who loves to make this nice frame home new again, lots of hardwood floors, nice size rooms, as per seller upstairs has some plumbing for a 2nd bathroom, metal roof, house will need new HVAC, newer nice windows, deck overlooking back yard, The Upstairs is not finished, please be careful walking on the upstairs floor, would be a nice second bedroom and/or den if finished, call today! (Buyer to verify the size of home and size of Lot) Take caution when walking on upstairs floor.

60 Fitch Ave, Winchester

$83,000

Investor special! This property has been fully gutted and is ready for your vision. Major groundwork has already begun, including new PEX plumbing lines installed for water service, updated framing, and electrical improvements underway. Designed to accommodate a 3-bedroom, 2-bath layout, this property offers a true blank slate for investors, flippers, or contractors looking to customize finishes and maximize value. With strong resale potential, the after-repair value (ARV) is projected to be in the ~$240,000 range based on comparable renovated homes in the area. Bring your plans and transform this property into a standout home or profitable investment. Owner/agent

3 Beds ⋅ 2 Baths ⋅ 26005996 MLS

Investor special! This property has been fully gutted and is ready for your vision. Major groundwork has already begun, including new PEX plumbing lines installed for water service, updated framing, and electrical improvements underway. Designed to accommodate a 3-bedroom, 2-bath layout, this property offers a true blank slate for investors, flippers, or contractors looking to customize finishes and maximize value. With strong resale potential, the after-repair value (ARV) is projected to be in the ~$240,000 range based on comparable renovated homes in the area. Bring your plans and transform this property into a standout home or profitable investment. Owner/agent

32 Hays St, Winchester

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