Real Estate Investment Properties for Sale in Winchester, MA
Looking for investment property in Winchester, MA with high ROI ?
Explore a variety of short-term homes & houses in Winchester, MA. Invest wisely with VRBO & Winchester, MA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Winchester, MA
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
571 Washington StWinchester, MAStep into this charming 3-bedroom home that radiates warmth and character from the moment ... |
3 beds | 1 baths | 1,425 sq.ft. |
$959,000 |
Airbnb cash on cash: 0.01%
|
44 Amberwood DriveWinchester, MAPicture your family in this unique colonial, just one street over from the amazing Vinson-... |
3 beds | 3 baths | 3,002 sq.ft. |
$1,765,300 |
Airbnb cash on cash: -0.88%
|
20 Grove PlWinchester, MAFrom the moment you enter this European-style Victorian, youâll be charmed. The first le... |
5 beds | 4 baths | 3,294 sq.ft. |
$1,879,000 |
Airbnb cash on cash: -0.32%
|
200 Swanton St #432Winchester, MAThis beautifully maintained one-bedroom condo at Parkview offers exceptional value in Winc... |
1 beds | 1 baths | 606 sq.ft. |
$419,900 |
Airbnb cash on cash: 0.7%
|
89 Main StWinchester, MAWelcome to this charming Cape on a spacious corner lot in Winchester. The main level offer... |
3 beds | 3 baths | 2,648 sq.ft. |
$1,125,000 |
Airbnb cash on cash: -0.29%
|
200 Swanton St #T11Winchester, MAMove right into this immaculate, renovated walk-in condo with an oversized layout and a hi... |
1 beds | 1 baths | 634 sq.ft. |
$409,900 |
Airbnb cash on cash: 2.09%
|
Real Estate investment in Winchester, MA
There are 6 properties for sale in the city of Winchester . The median list price in Winchester is $1,042,000 and the average price per square foot is $539. In September 2025, the average monthly cash on cash return in Winchester is 1.00%. The average monthly rental income in Winchester is $3,692.