Real Estate Investment Properties for Sale in Winchester, NH
Looking for investment property in Winchester, NH with high ROI ?
Explore a variety of short-term homes & houses in Winchester, NH. Invest wisely with VRBO & Winchester, NH 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, NH
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
27 Headlands RdWinchester, NHStunning Waterfront! Like new Cape style post and beam beauty with direct waterfront on F... |
2 beds | 1 baths | 1,351 sq.ft. |
$725,000 |
Airbnb cash on cash: N/A
|
49 Forest Lake CirWinchester, NHKick back and relax at this stylish year-round lake area country cottage. Includes deed a... |
2 beds | 1 baths | 937 sq.ft. |
$350,000 |
Airbnb cash on cash: N/A
|
406 Back Ashuelot RoadWinchester, NHBecome a part of history! This amazing building was the center for education for generatio... |
7 beds | 5 baths | 5,607 sq.ft. |
$600,000 |
Airbnb cash on cash: N/A
|
259 Bolton RdWinchester, NHStunning & modern unique True Timber Frame home has it all with incredible CT River views ... |
3 beds | 2 baths | 3,472 sq.ft. |
$849,900 |
Airbnb cash on cash: N/A
|
240 Forest Lake RdWinchester, NHReal Country Living in an antique post & beam farmhouse on 11+ acres, COMPLETELY remod... |
4 beds | 2 baths | 2,200 sq.ft. |
$610,000 |
Airbnb cash on cash: N/A
|
130 Watson RoadWinchester, NHThis beautiful 3-bedroom home is set on 12 acres of designated wildlife habitat overlookin... |
3 beds | 2 baths | 2,145 sq.ft. |
$694,900 |
Airbnb cash on cash: N/A
|
159 Ashuelot Main StWinchester, NHMARKET ADJUSTMENT! Upgrade with this NEW, Classic and modern home close to all town servic... |
4 beds | 3 baths | 2,832 sq.ft. |
$559,900 |
Airbnb cash on cash: N/A
|
71 Parker StreetWinchester, NHNew Year, New Home! Come see this charming 3 bedroom, 1 bathroom home with a spacious yar... |
3 beds | 1 baths | 1,372 sq.ft. |
$239,000 |
Airbnb cash on cash: N/A
|
583 Burt Hill RdWinchester, NHWelcome to your move-in-ready sanctuary! This beautifully updated home perfectly blends mo... |
4 beds | 3 baths | 3,114 sq.ft. |
$549,900 |
Airbnb cash on cash: N/A
|
20 Bilo AveWinchester, NHUpdated and ready to love, this bright and sunny 3-bedroom, 1-bath home offers 1,145 squar... |
3 beds | 1 baths | 1,145 sq.ft. |
$295,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Winchester, NH
There are 13 properties for sale in the city of Winchester . The median list price in Winchester is $450,000 and the average price per square foot is $193. In February 2026, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $2,793.