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 |
|---|---|---|---|
53 Winford WayWinchester, MAStunning new construction in highly sought-after Winchester! This thoughtfully designed ho... |
5 beds | 4 baths | 5,083 sq.ft. |
$2,799,000 |
Airbnb cash on cash: -0.74%
|
200 Swanton St unit: T28Winchester, MA1 bedroom condo in Winchester. This garden-level unit offers tranquil pond views and direc... |
1 beds | 1 baths | 634 sq.ft. |
$375,000 |
Airbnb cash on cash: -0.75%
|
200 Swanton St #228Winchester, MAThis one bed one bath, bright unit features an open layout with peaceful views overlooking... |
1 beds | 1 baths | 606 sq.ft. |
$375,000 |
Airbnb cash on cash: -0.93%
|
25 Myopia RoadWinchester, MAA timeless home of exceptional craftsmanship on the coveted slope of Myopia Hill, offering... |
4 beds | 4 baths | 4,847 sq.ft. |
$3,390,000 |
Airbnb cash on cash: -1.62%
|
40 Englewood RdWinchester, MANestled on a quiet, tree-lined street near the Fells, this charming Cape with classic dorm... |
4 beds | 2 baths | 1,841 sq.ft. |
$1,099,000 |
Airbnb cash on cash: -0.21%
|
Real Estate investment in Winchester, MA
There are 5 properties for sale in the city of Winchester . The median list price in Winchester is $434,990 and the average price per square foot is $192. In May 2026, the average monthly cash on cash return in Winchester is 1.00%. The average monthly rental income in Winchester is $3,304.