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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 well-designed two-story floor plan with a welcoming foyer, spacious living room, kitchen, utility area, and half bath on the main level. Upstairs, you'll find three generously sized bedrooms and a full bathroom, creating a comfortable layout that appeals to long-term tenants. Additional features include private decks, ceiling fans, window blinds, ample off-street parking, and generously sized yards. Conveniently maintained and fully leased, this multifamily property offers immediate cash flow with minimal owner responsibilities. Showings are available by appointment only with advance notice to accommodate the tenants.

9 Beds ⋅ 6 Baths ⋅ 26020069 MLS

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 well-designed two-story floor plan with a welcoming foyer, spacious living room, kitchen, utility area, and half bath on the main level. Upstairs, you'll find three generously sized bedrooms and a full bathroom, creating a comfortable layout that appeals to long-term tenants. Additional features include private decks, ceiling fans, window blinds, ample off-street parking, and generously sized yards. Conveniently maintained and fully leased, this multifamily property offers immediate cash flow with minimal owner responsibilities. Showings are available by appointment only with advance notice to accommodate the tenants.

341-345 Carolina Ave, Winchester

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

Investment opportunity in the heart of Winchester! Brick Triplex featuring a main level, high visibility commercial space with Lexington Avenue frontage and two apartments on the upper level! Each apartment has two bedrooms, one bath. One unit has been recently remodeled, the other has potential for value add. The flexible commercial space contains 3 half baths. Laundry hook-ups in all 3 units! Basement for extra storage room with freight elevator. Two new HVAC units and a new roof within the last 2 years! Approximately 16 parking spaces. All 3 units are currently occupied.

4 Beds ⋅ 5 Baths ⋅ 26010324 MLS

Investment opportunity in the heart of Winchester! Brick Triplex featuring a main level, high visibility commercial space with Lexington Avenue frontage and two apartments on the upper level! Each apartment has two bedrooms, one bath. One unit has been recently remodeled, the other has potential for value add. The flexible commercial space contains 3 half baths. Laundry hook-ups in all 3 units! Basement for extra storage room with freight elevator. Two new HVAC units and a new roof within the last 2 years! Approximately 16 parking spaces. All 3 units are currently occupied.

502 W Lexington Ave, Winchester

You won't want to miss adding this income-producing apartment complex to your portfolio. This property is comprised of 16 one-bedroom/one-bathroom apartments with 100% occupancy. Complex is conveniently located in downtown Winchester and only 20 minutes from Lexington via easy highway access. The building sits on a 0.34 acre lot with 20+ parking spaces. Property has several updates including roof replacement in 2022, new siding in 2023, and 6 of the AC units were replaced in the last three years. The main electrical service mast was replaced in 2023, and all 100-amp breakers were replaced in 2025. Most units have been updated with LVP flooring.

16 Beds ⋅ 16 Baths ⋅ 26007993 MLS

You won't want to miss adding this income-producing apartment complex to your portfolio. This property is comprised of 16 one-bedroom/one-bathroom apartments with 100% occupancy. Complex is conveniently located in downtown Winchester and only 20 minutes from Lexington via easy highway access. The building sits on a 0.34 acre lot with 20+ parking spaces. Property has several updates including roof replacement in 2022, new siding in 2023, and 6 of the AC units were replaced in the last three years. The main electrical service mast was replaced in 2023, and all 100-amp breakers were replaced in 2025. Most units have been updated with LVP flooring.

16 Linden Ave, Winchester

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.

4 Beds ⋅ 4 Baths ⋅ 26000922 MLS

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.

1128-1130 Dale Dr, Winchester

Turnkey downtown triplex with tenants already in place. An excellent addition to any investor's portfolio. Two units have been recently updated, while the third features a long-term tenant with future value-add potential. Property includes two 1BD/1BA units and one 2BD/1BA unit. Tenants pay all utilities directly except water, which is on a RUB system, keeping operating costs low. Strong income potential in a prime downtown location with continued upside. Selling as-is.

4 Beds ⋅ 3 Baths ⋅ 26004331 MLS

Turnkey downtown triplex with tenants already in place. An excellent addition to any investor's portfolio. Two units have been recently updated, while the third features a long-term tenant with future value-add potential. Property includes two 1BD/1BA units and one 2BD/1BA unit. Tenants pay all utilities directly except water, which is on a RUB system, keeping operating costs low. Strong income potential in a prime downtown location with continued upside. Selling as-is.

130 E Broadway St, Winchester