Airbnb Properties for Sale in Winchester, CT

Looking for a vacation rental investment in Winchester, CT with high ROI ?

Explore a range of newly added short-term rental homes in Winchester, CT. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Winchester, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
115 Moore Avenue Winchester, CT If you are looking for a mini estate look no further. This completely remodeled home has e...	3 beds \| 3 baths \| 2,240 sq.ft.	$449,900	Airbnb cash on cash: 6.83% Traditional cash on cash: 6.44% Airbnb Rental Income: $4795 Traditional Rental Income: $3642 Airbnb ROI: 6.83% Traditional ROI: 6.44%
Airbnb Properties for Sale in Other Cities of Connecticut
118 40 Acre Mountain Road Danbury , CT Stunning year-round views of Candlewood Lake set the stage for this contemporary Ranch sty...	3 beds \| 3 baths \| 2,755 sq.ft.	$685,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 4.46% Airbnb Rental Income: $6933 Traditional Rental Income: $4167 Airbnb ROI: 6.68% Traditional ROI: 4.46%
153 THOMPSON HILL RD Portland , CT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2 baths \| 1,704 sq.ft.	$451,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 3.54% Airbnb Rental Income: $3436 Traditional Rental Income: $2560 Airbnb ROI: 3.81% Traditional ROI: 3.54%
22 Boylston Street Milford , CT Welcome home to your quiet new home on Boylston Street! This charming three bedroom Cape p...	3 beds \| 2 baths \| 1,479 sq.ft.	$455,000	Airbnb cash on cash: 9.82% Traditional cash on cash: 5.42% Airbnb Rental Income: $6372 Traditional Rental Income: $3247 Airbnb ROI: 9.82% Traditional ROI: 5.42%
4 Ledgebrook Drive #4 Norwalk , CT Discover a perfect blend of style and sophistication in this chic unit, offering the essen...	2 beds \| 2 baths \| 1,173 sq.ft.	$399,000	Airbnb cash on cash: 5.35% Traditional cash on cash: 4.21% Airbnb Rental Income: $4409 Traditional Rental Income: $3059 Airbnb ROI: 5.35% Traditional ROI: 4.21%
45 Milford Point Road Milford , CT Stunningly unique waterfront contemporary on private sandy beach, turn key. From the Banks...	4 beds \| 4 baths \| 2,264 sq.ft.	$2,290,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 0.61% Airbnb Rental Income: $9687 Traditional Rental Income: $4898 Airbnb ROI: 2.02% Traditional ROI: 0.61%
33 Point Beach Drive Milford , CT Exquisite waterfront living directly on the water. You'll be astounded by the breathtaking...	3 beds \| 3 baths \| 2,308 sq.ft.	$999,900	Airbnb cash on cash: 3% Traditional cash on cash: 2.42% Airbnb Rental Income: $6372 Traditional Rental Income: $4574 Airbnb ROI: 3% Traditional ROI: 2.42%
86 Catalina Drive Coventry , CT Beautifully remodeled Cape oh so close to Coventry Lake! Welcome to Lake Life! Part of the...	3 beds \| 1 baths \| 1,373 sq.ft.	$299,900	Airbnb cash on cash: 9.57% Traditional cash on cash: 6.02% Airbnb Rental Income: $4334 Traditional Rental Income: $2420 Airbnb ROI: 9.57% Traditional ROI: 6.02%
16 Brookside Drive Easton , CT Welcome to 16 Brookside Drive situated on 3 acres located in the heart of Easton. FULLY FU...	3 beds \| 4 baths \| 2,937 sq.ft.	$749,999	Airbnb cash on cash: 3.4% Traditional cash on cash: 3.17% Airbnb Rental Income: $5517 Traditional Rental Income: $4244 Airbnb ROI: 3.4% Traditional ROI: 3.17%
69 Everett Street Stratford , CT Move in ready Colonial which features new/newer asphalt roof, maintenance free vinyl sidin...	3 beds \| 2 baths \| 1,443 sq.ft.	$399,900	Airbnb cash on cash: 7.85% Traditional cash on cash: 6.27% Airbnb Rental Income: $4868 Traditional Rental Income: $3276 Airbnb ROI: 7.85% Traditional ROI: 6.27%
2071 Middletown Avenue North Branford , CT Here's your chance to invest in a remarkable and rare opportunity: a beautifully renovated...	3 beds \| 3 baths \| 1,458 sq.ft.	$499,900	Airbnb cash on cash: 5.6% Traditional cash on cash: 4.95% Airbnb Rental Income: $4709 Traditional Rental Income: $3431 Airbnb ROI: 5.6% Traditional ROI: 4.95%
21 Karl Street Litchfield , CT Welcome to 21 Karl Street, a classic four-bedroom colonial that perfectly blends timeless ...	4 beds \| 2 baths \| 2,052 sq.ft.	$439,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 5.18% Airbnb Rental Income: $4073 Traditional Rental Income: $3161 Airbnb ROI: 5.28% Traditional ROI: 5.18%
10 South Street #88 Danbury , CT HIGHEST AND BEST TUESDAY, AUGUST 27, 2024 BY 5PM. Quiet, lovely Summit View condominium co...	2 beds \| 2 baths \| 1,340 sq.ft.	$399,900	Airbnb cash on cash: 4.48% Traditional cash on cash: 3.46% Airbnb Rental Income: $3762 Traditional Rental Income: $2563 Airbnb ROI: 4.48% Traditional ROI: 3.46%
352 Flanders Road Stonington , CT Exquisite 4-bedroom, 2-bath Cape Cod set on 2.60 secluded acres, offers a perfect balance ...	4 beds \| 2 baths \| 1,796 sq.ft.	$600,000	Airbnb cash on cash: 7.67% Traditional cash on cash: 3.88% Airbnb Rental Income: $6684 Traditional Rental Income: $3259 Airbnb ROI: 7.67% Traditional ROI: 3.88%
13 Woodhill Road #13 Milford , CT Welcome to an exquisite townhouse nestled in the highly sought-after Glenwood condominium ...	2 beds \| 2 baths \| 1,902 sq.ft.	$319,900	Airbnb cash on cash: 7.69% Traditional cash on cash: 6.83% Airbnb Rental Income: $4381 Traditional Rental Income: $3204 Airbnb ROI: 7.69% Traditional ROI: 6.83%
21 Chimney Drive Bethel , CT An adorable expanded split, 3 spacious Bedrooms including the master bath with skylight an...	3 beds \| 3 baths \| 2,076 sq.ft.	$575,000	Airbnb cash on cash: 6.59% Traditional cash on cash: 4.32% Airbnb Rental Income: $5999 Traditional Rental Income: $3590 Airbnb ROI: 6.59% Traditional ROI: 4.32%

Vacation Rentals in Winchester

There are 1 vacation rental properties available for sale in the city of Winchester . The median list price of Airbnb properties available for sale in Winchester is $374,450 and the average price per square foot is $155. The cash on cash return on vacation rentals in Winchester is 5.00%. The average monthly short term rental income in Winchester is $3,619.

Winchester, CT Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 1 Airbnb properties available for sale in Winchester.

In 2024, the best neighborhood to buy short term rental property is Winchester.

In December 2024, the average Airbnb occupancy rate in Winchester is 58%.

Airbnb data on vacation rentals in Winchester, CT is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winchester, CT market insights, guest information and booking details, seasonality trends and historical Winchester, CT Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Winchester, CT

115 Moore Avenue

Winchester, CT

3 beds | 3 baths | 2,240 sq.ft.

$449,900

Airbnb cash on cash: 6.83%

Traditional cash on cash: 6.44%

Airbnb Rental Income: $4795

Traditional Rental Income: $3642

Airbnb ROI: 6.83%

Traditional ROI: 6.44%

Airbnb Properties for Sale in Other Cities of Connecticut

Danbury , CT

3 beds | 3 baths | 2,755 sq.ft.

$685,000

Airbnb cash on cash: 6.68%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $6933

Traditional Rental Income: $4167

Airbnb ROI: 6.68%

Traditional ROI: 4.46%

Portland , CT

3 beds | 2 baths | 1,704 sq.ft.

$451,000

Airbnb cash on cash: 3.81%

Traditional cash on cash: 3.54%

Airbnb Rental Income: $3436

Traditional Rental Income: $2560

Airbnb ROI: 3.81%

Traditional ROI: 3.54%

Milford , CT

3 beds | 2 baths | 1,479 sq.ft.

$455,000

Airbnb cash on cash: 9.82%

Traditional cash on cash: 5.42%

Airbnb Rental Income: $6372

Traditional Rental Income: $3247

Airbnb ROI: 9.82%

Traditional ROI: 5.42%

Norwalk , CT

2 beds | 2 baths | 1,173 sq.ft.

$399,000

Airbnb cash on cash: 5.35%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $4409

Traditional Rental Income: $3059

Airbnb ROI: 5.35%

Traditional ROI: 4.21%

Milford , CT

4 beds | 4 baths | 2,264 sq.ft.

$2,290,000

Airbnb cash on cash: 2.02%

Traditional cash on cash: 0.61%

Airbnb Rental Income: $9687

Traditional Rental Income: $4898

Airbnb ROI: 2.02%

Traditional ROI: 0.61%

Milford , CT

3 beds | 3 baths | 2,308 sq.ft.

$999,900

Airbnb cash on cash: 3%

Traditional cash on cash: 2.42%

Airbnb Rental Income: $6372

Traditional Rental Income: $4574

Airbnb ROI: 3%

Traditional ROI: 2.42%

Coventry , CT

3 beds | 1 baths | 1,373 sq.ft.

$299,900

Airbnb cash on cash: 9.57%

Traditional cash on cash: 6.02%

Airbnb Rental Income: $4334

Traditional Rental Income: $2420

Airbnb ROI: 9.57%

Traditional ROI: 6.02%

Easton , CT

3 beds | 4 baths | 2,937 sq.ft.

$749,999

Airbnb cash on cash: 3.4%

Traditional cash on cash: 3.17%