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 RoadWinchester, NHStunning Waterfront! Like new Cape style post and beam beauty with direct waterfront on F... |
2 beds | 2 baths | 1,351 sq.ft. |
$735,000 |
Airbnb cash on cash: 0.03%
|
49 Forest Lake CircleWinchester, NHKick back and relax at this stylish year-round lake area country cottage. Includes deed a... |
2 beds | 1 baths | 937 sq.ft. |
$360,000 |
Airbnb cash on cash: 2.65%
|
398 Scofield Mountain RoadWinchester, NHOne of New England's most unique & premiere properties, a sprawling sanctuary set on over ... |
4 beds | 6 baths | 5,120 sq.ft. |
$5,200,000 |
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
|
63 Headlands RoadWinchester, NHRare expansive waterfront retreat on 2 private acres! Updated with modern comforts, this c... |
2 beds | 2 baths | 2,036 sq.ft. |
$720,000 |
Airbnb cash on cash: -0.22%
|
153 Back Ashuelot RoadWinchester, NH****Back on the market due to Buyers Financing****Welcome Homeâan incredible opportunity... |
3 beds | 4 baths | 2,688 sq.ft. |
$355,000 |
Airbnb cash on cash: N/A
|
12 Miner CourtWinchester, NHWelcome to 12 Miner Court - a delightful 3-bedroom, 1-bath home set on a .47-acre lot with... |
3 beds | 1 baths | 1,416 sq.ft. |
$279,000 |
Airbnb cash on cash: N/A
|
510 Old Westport RoadWinchester, NHMOTIVATED SELLERS!!!!! Welcome to this brand-new construction in the charming town of Winc... |
3 beds | 2 baths | 1,930 sq.ft. |
$549,900 |
Airbnb cash on cash: N/A
|
45 Forest Lake CircleWinchester, NHForest Lake Access! This is a charming recently renovated Ranch house. Sprawling 3/4 Bedro... |
4 beds | 2 baths | 1,500 sq.ft. |
$380,000 |
Airbnb cash on cash: N/A
|
111 Warwick RoadWinchester, NHWelcome to this THREE YEARS YOUNG, LIGHT-FILLED COLONIAL SPLIT that is sure to impress! ... |
4 beds | 2 baths | 2,656 sq.ft. |
$455,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Winchester, NH
There are 15 properties for sale in the city of Winchester . The median list price in Winchester is $357,500 and the average price per square foot is $163. In October 2025, the average monthly cash on cash return in Winchester is 6.00%. The average monthly rental income in Winchester is $2,875.