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: -0.27%
|
571 Washington StWinchester, MABest valued single family in Winchester with incredible fenced backyard and expansive pati... |
3 beds | 1 baths | 1,425 sq.ft. |
$898,000 |
Airbnb cash on cash: -0.36%
|
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. |
$1,869,000 |
Airbnb cash on cash: -0.52%
|
446 Highland AveWinchester, MACharming Spanish-style home in desirable Winchester! This unique property features a beaut... |
2 beds | 2 baths | 2,033 sq.ft. |
$999,000 |
Airbnb cash on cash: -0.64%
|
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: -0.64%
|
200 Swanton St #T11Winchester, MAOPEN HOUSES CANCELLED !Move right into this immaculate, renovated walk-in condo with an ov... |
1 beds | 1 baths | 634 sq.ft. |
$397,000 |
Airbnb cash on cash: 2.26%
|
Real Estate investment in Winchester, MA
There are 6 properties for sale in the city of Winchester . The median list price in Winchester is $1,062,000 and the average price per square foot is $421. In November 2025, the average monthly cash on cash return in Winchester is 1.00%. The average monthly rental income in Winchester is $3,084.