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 |
|---|---|---|---|
84 Oak StWinchester, MAGreat opportunity to live in Winchester! Spacious bungalow in need of updating features e... |
4 beds | 2 baths | 2,083 sq.ft. |
$888,000 |
Airbnb cash on cash: 1.16%
|
200 Swanton St #T35Winchester, MAJust in time for the warm weather. Move right into this 2 bedroom, terrace level condo at... |
2 beds | 1 baths | 810 sq.ft. |
$400,000 |
Airbnb cash on cash: 0.46%
|
247 Washington St #11Winchester, MAThis spacious condo is just minutes away from downtown Winchester and its amenities includ... |
3 beds | 2 baths | 1,494 sq.ft. |
$729,000 |
Airbnb cash on cash: -0.11%
|
666 Main St #315Winchester, MALocation is everything! Located in Winchester Center, on Wedge Pond and walking distance t... |
2 beds | 2 baths | 1,025 sq.ft. |
$649,900 |
Airbnb cash on cash: -0.58%
|
53 Winford WayWinchester, MAStunning new construction in highly sought-after Winchester! This thoughtfully designed ho... |
5 beds | 4 baths | 5,083 sq.ft. |
$2,399,000 |
Airbnb cash on cash: 0.25%
|
276 High StWinchester, MAThis stunning, freshly painted, home is located in a picturesque and unique setting, eleva... |
5 beds | 3 baths | 5,006 sq.ft. |
$2,195,000 |
Airbnb cash on cash: -0.38%
|
1 Town WayWinchester, MA1 Town Way, Winchester, MA 01890 | Single Family Residential |
3 beds | 3 baths | 3,010 sq.ft. |
$1,799,000 |
Airbnb cash on cash: -1.15%
|
37 Mayflower RdWinchester, MA37 Mayflower Rd, Winchester, MA 01890 | Single Family Residential |
7 beds | 7 baths | 8,540 sq.ft. |
$3,179,000 |
Airbnb cash on cash: -1.07%
|
9 Albamont RdWinchester, MA9 Albamont Rd, Winchester, MA 01890 | Single Family Residential |
6 beds | 5 baths | 6,100 sq.ft. |
$3,200,000 |
Airbnb cash on cash: -1.07%
|
10 Dartmouth StWinchester, MA10 Dartmouth St, Winchester, MA 01890 | Single Family Residential |
5 beds | 2 baths | 4,028 sq.ft. |
$2,999,000 |
Airbnb cash on cash: -1%
|
63-65 Harvard StWinchester, MATwo-family homes in Winchester are limited, which is exactly why opportunities like this g... |
5 beds | 3 baths | 2,186 sq.ft. |
$1,150,000 |
Airbnb cash on cash: 1.21%
|
50 Middlesex St #50Winchester, MACompletely renovated from top to bottom, this brand-new 2-bedroom, 2-bath condo offers the... |
2 beds | 2 baths | 1,036 sq.ft. |
$799,000 |
Airbnb cash on cash: -0.34%
|
46 Clark StWinchester, MAWelcome to this meticulously renovated four-bedroom Colonial, ideally situated on a quiet ... |
4 beds | 1 baths | 1,777 sq.ft. |
$1,064,000 |
Airbnb cash on cash: 0.49%
|
42 Wildwood StWinchester, MA42 Wildwood St, Winchester, MA 01890 | Single Family Residential |
7 beds | 4 baths | 4,930 sq.ft. |
$2,299,000 |
Airbnb cash on cash: -0.62%
|
8 Oak StWinchester, MA8 Oak St, Winchester, MA 01890 | Single Family Residential |
5 beds | 2 baths | 2,391 sq.ft. |
$1,125,000 |
Airbnb cash on cash: 1.04%
|
8-10 Oak StWinchester, MA8-10 Oak St, Winchester, MA 01890 | Multi Family |
5 beds | 2 baths | 2,391 sq.ft. |
$1,125,000 |
Airbnb cash on cash: 1.04%
|
15 Clark StWinchester, MA15 Clark St, Winchester, MA 01890 | Single Family Residential |
3 beds | 1 baths | 1,340 sq.ft. |
$849,000 |
Airbnb cash on cash: 0.04%
|
241 Ridge StWinchester, MA241 Ridge St, Winchester, MA 01890 | Single Family Residential |
4 beds | 2 baths | 2,480 sq.ft. |
$1,599,000 |
Airbnb cash on cash: -0.65%
|
79 Grove StWinchester, MA79 Grove St, Winchester, MA 01890 | Single Family Residential |
5 beds | 3 baths | 3,210 sq.ft. |
$1,899,000 |
Airbnb cash on cash: -0.29%
|
257 Cross StWinchester, MA257 Cross St, Winchester, MA 01890 | Multi Family |
5 beds | 2 baths | 2,801 sq.ft. |
$1,099,000 |
Airbnb cash on cash: 1.12%
|
47 Water StWinchester, MA47 Water St, Winchester, MA 01890 | Single Family Residential |
3 beds | 1 baths | 1,356 sq.ft. |
$950,000 |
Airbnb cash on cash: -0.2%
|
258 Cross StWinchester, MA258 Cross St, Winchester, MA 01890 | Single Family Residential |
4 beds | 2 baths | 1,719 sq.ft. |
$999,900 |
Airbnb cash on cash: 0.29%
|
15 Clark St #15Winchester, MA15 Clark St #15, Winchester, MA 01890 | Townhouse |
3 beds | 1 baths | 1,340 sq.ft. |
$849,000 |
Airbnb cash on cash: 0.04%
|
666 Main #211Winchester, MA666 Main #211, Winchester, MA 01890 | Condo/Coop |
2 beds | 2 baths | 1,170 sq.ft. |
$700,000 |
Airbnb cash on cash: -0.92%
|
423 Washington StWinchester, MA423 Washington St, Winchester, MA 01890 | Single Family Residential |
4 beds | 3 baths | 2,690 sq.ft. |
$1,350,000 |
Airbnb cash on cash: -0.36%
|
14 Hillside AveWinchester, MA14 Hillside Ave, Winchester, MA 01890 | Single Family Residential |
4 beds | 4 baths | 3,881 sq.ft. |
$2,300,000 |
Airbnb cash on cash: -1.13%
|
9 Plymouth RdWinchester, MA9 Plymouth Rd, Winchester, MA 01890 | Single Family Residential |
5 beds | 3 baths | 4,071 sq.ft. |
$2,500,000 |
Airbnb cash on cash: -0.75%
|
150 Cambridge StWinchester, MA150 Cambridge St, Winchester, MA 01890 | Single Family Residential |
3 beds | 1 baths | 1,711 sq.ft. |
$1,099,000 |
Airbnb cash on cash: -0.47%
|
26 N GatewayWinchester, MA26 N Gateway, Winchester, MA 01890 | Single Family Residential |
4 beds | 3 baths | 3,210 sq.ft. |
$2,099,000 |
Airbnb cash on cash: -1.02%
|
200 Swanton #L8Winchester, MA200 Swanton #L8, Winchester, MA 01890 | Condo/Coop |
1 beds | 1 baths | 388 sq.ft. |
$288,750 |
Airbnb cash on cash: 0.34%
|
38 Robinhood RdWinchester, MA38 Robinhood Rd, Winchester, MA 01890 | Single Family Residential |
3 beds | 1 baths | 1,736 sq.ft. |
$1,175,000 |
Airbnb cash on cash: -0.58%
|
117 Highland AveWinchester, MA117 Highland Ave, Winchester, MA 01890 | Single Family Residential |
5 beds | 3 baths | 3,722 sq.ft. |
$1,675,000 |
Airbnb cash on cash: -0.03%
|
78 Bacon StWinchester, MA78 Bacon St, Winchester, MA 01890 | Single Family Residential |
5 beds | 3 baths | 5,230 sq.ft. |
$2,499,000 |
Airbnb cash on cash: -0.75%
|
10 Rangeley RdWinchester, MA10 Rangeley Rd, Winchester, MA 01890 | Single Family Residential |
5 beds | 4 baths | 5,406 sq.ft. |
$3,199,000 |
Airbnb cash on cash: -1.09%
|
7 Wainwright Rd #47Winchester, MA7 Wainwright Rd #47, Winchester, MA 01890 | Townhouse |
3 beds | 3 baths | 2,145 sq.ft. |
$1,299,000 |
Airbnb cash on cash: -1.62%
|
129 Washington St #129Winchester, MA129 Washington St #129, Winchester, MA 01890 | Townhouse |
3 beds | 3 baths | 2,420 sq.ft. |
$1,099,000 |
Airbnb cash on cash: -0.47%
|
18 Middlesex StWinchester, MA18 Middlesex St, Winchester, MA 01890 | Single Family Residential |
4 beds | 4 baths | 5,233 sq.ft. |
$2,795,000 |
Airbnb cash on cash: -1.32%
|
8 Priscilla LnWinchester, MA8 Priscilla Ln, Winchester, MA 01890 | Single Family Residential |
5 beds | 5 baths | 6,500 sq.ft. |
$3,149,000 |
Airbnb cash on cash: -1.06%
|
16 & 16A Glenwood AveWinchester, MA16 & 16A Glenwood Ave, Winchester, MA 01890 | Single Family Residential |
6 beds | 4 baths | 6,900 sq.ft. |
$1,899,000 |
Airbnb cash on cash: -0.29%
|
83 Church St #15Winchester, MA83 Church St #15, Winchester, MA 01890 | Condo/Coop |
2 beds | 1 baths | 1,365 sq.ft. |
$999,000 |
Airbnb cash on cash: -1.76%
|
Real Estate investment in Winchester, MA
There are 55 properties for sale in the city of Winchester . The median list price in Winchester is $1,386,670 and the average price per square foot is $579. In August 2026, the average monthly cash on cash return in Winchester is 1.00%. The average monthly rental income in Winchester is $3,639.