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$350,000
3 Beds ⋅ 3 Baths ⋅ 26024167 MLS
Attention Investors! This 3 plex in the heart of Winchester is a great investment. There are 3 apartments that are all currently rented out. The bottom floor has a huge living room, bathroom, and kitchen. The other two upstairs also have a living room, kitchen, bathroom, and bedroom. There is also a huge deck on the back for entertaining. Schedule an appointment to take a look before this one is gone.

135 E Broadway St, Winchester
$495,000
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
$340,000
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.

502 W Lexington Ave, Winchester
$1,200,000
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
$239,000
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
$455,000
8 Beds ⋅ 4 Baths ⋅ 26004961 MLS
Fully stabilized and 100% occupied, this is a quality investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8 bedrooms, 4 bathrooms, and approximately 5058 square feet, this property provides strong rental potential in a convenient location close to downtown shopping, dining, and local amenities. The units are clean, well-maintained, and ready for new tenants, making this an excellent option for investors seeking a solid income-producing property. Schedule your showing today before this opportunity is gone! Monthly Income of $3,860 ($46,320 Annually)

265 S Highland St, Winchester