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, 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, you'll be charmed. The first leve... |
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%
|
200 Swanton St #T28Winchester, MABeautiful terrace-level 1-bedroom condo in Winchester! This garden-level unit offers tranq... |
1 beds | 1 baths | 634 sq.ft. |
$375,000 |
Airbnb cash on cash: 2.41%
|
32 Oak St.Winchester, MAPrime location near town center! This renovated 4-bed, 3-bath home is nestled in a private... |
4 beds | 3 baths | 2,652 sq.ft. |
$1,350,000 |
Airbnb cash on cash: 0.18%
|
200 Swanton St #228Winchester, MABeautifully maintained and freshly painted 1-bedroom condo at Parkview Condominiums in Win... |
1 beds | 1 baths | 606 sq.ft. |
$379,000 |
Airbnb cash on cash: 2.11%
|
35 Glen GrnWinchester, MAWelcome to this beautifully maintained Colonial in a highly desirable family neighborhood ... |
4 beds | 2 baths | 3,509 sq.ft. |
$1,899,000 |
Airbnb cash on cash: -0.57%
|
8 Buckman DrWinchester, MAMove-in ready home on Winchester's highly desirable West Side, set on a quiet street with ... |
5 beds | 6 baths | 4,773 sq.ft. |
$2,299,000 |
Airbnb cash on cash: -0.77%
|
49 Spruce StWinchester, MAFantastic opportunity to own in Winchester! This inviting home is move-in ready and offers... |
3 beds | 2 baths | 1,710 sq.ft. |
$815,000 |
Airbnb cash on cash: -0.1%
|
25 Myopia RdWinchester, MAA timeless home of exceptional craftsmanship on the coveted slope of Myopia Hill, offering... |
4 beds | 3 baths | 4,847 sq.ft. |
$3,390,000 |
Airbnb cash on cash: -1.43%
|
Real Estate investment in Winchester, MA
There are 11 properties for sale in the city of Winchester . The median list price in Winchester is $437,450 and the average price per square foot is $192. In March 2026, the average monthly cash on cash return in Winchester is 1.00%. The average monthly rental income in Winchester is $3,692.