Airbnb Properties for Sale in Windsor, CT

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

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

Airbnb For Sale in Windsor, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
281 MOUNTAIN ROAD Windsor, CT One floor living at Its best describes this ranch style home with fireplaced living room, ...	3 beds \| 2 baths \| 1,132 sq.ft.	$230,000	Airbnb cash on cash: 8.41% Traditional cash on cash: 6.82% Airbnb Rental Income: $3346 Traditional Rental Income: $2253 Airbnb ROI: 8.41% Traditional ROI: 6.82%
83 Corey Street Windsor, CT Spacious Cape Cod Home with 4 bedrooms, 2 full bathrooms. Completely renovated! Kitchen wi...	3 beds \| 2 baths \| 1,306 sq.ft.	$375,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 2.79% Airbnb Rental Income: $3346 Traditional Rental Income: $2170 Airbnb ROI: 4.01% Traditional ROI: 2.79%
25 Sunnyside Circle Windsor, CT Cozy 6 room Cape, with new pressured treated front entry; JUST MOVE IN- home is painted ne...	3 beds \| 2 baths \| 1,075 sq.ft.	$269,000	Airbnb cash on cash: 6.77% Traditional cash on cash: 6.56% Airbnb Rental Income: $3346 Traditional Rental Income: $2547 Airbnb ROI: 6.77% Traditional ROI: 6.56%
690 Bloomfield Avenue Windsor, CT Priced to Please! Ranch style 1 level living featuring over 1100 square feet of living spa...	3 beds \| 1 baths \| 1,110 sq.ft.	$249,900	Airbnb cash on cash: 7.51% Traditional cash on cash: 6.07% Airbnb Rental Income: $3346 Traditional Rental Income: $2259 Airbnb ROI: 7.51% Traditional ROI: 6.07%
Airbnb Properties for Sale in Other Cities of Connecticut
77 Hollenbeck Road Cornwall , CT Welcome to this charming home located in a quiet surrounding area with a set back driveway...	3 beds \| 3 baths \| 2,268 sq.ft.	$499,000	Airbnb cash on cash: 6.65% Traditional cash on cash: 6.17% Airbnb Rental Income: $5100 Traditional Rental Income: $3837 Airbnb ROI: 6.65% Traditional ROI: 6.17%
1658 Highland Avenue Waterbury , CT Welcome home to this 2 bedroom, 1 bath Raised Ranch! Main level features fully appointed k...	2 beds \| 1 baths \| 960 sq.ft.	$279,900	Airbnb cash on cash: 4.19% Traditional cash on cash: 4.06% Airbnb Rental Income: $2546 Traditional Rental Income: $1898 Airbnb ROI: 4.19% Traditional ROI: 4.06%
185 Greystone Road Plymouth , CT Welcome to 185 Greystone Rd, a beautifully updated home that blends comfort, style, and pr...	3 beds \| 2 baths \| 1,768 sq.ft.	$424,900	Airbnb cash on cash: 6.95% Traditional cash on cash: 5.33% Airbnb Rental Income: $4791 Traditional Rental Income: $3156 Airbnb ROI: 6.95% Traditional ROI: 5.33%
243 Sunshine Circle Bridgeport , CT COME SEE!! This beautiful starter 4 Bedroom 1.5 bath home, located on the north end of Bri...	4 beds \| 2 baths \| 1,920 sq.ft.	$385,000	Airbnb cash on cash: 7.63% Traditional cash on cash: 6.37% Airbnb Rental Income: $4777 Traditional Rental Income: $3339 Airbnb ROI: 7.63% Traditional ROI: 6.37%
10 David Street Waterford , CT Take a 3D Tour 24/7 or Enjoy a Video Walkthrough 24/7! Come explore 10 David St, Waterford...	3 beds \| 1 baths \| 1,202 sq.ft.	$315,000	Airbnb cash on cash: 7.18% Traditional cash on cash: 5.22% Airbnb Rental Income: $3583 Traditional Rental Income: $2217 Airbnb ROI: 7.18% Traditional ROI: 5.22%
163 Lake Road Warren , CT Listed on the CT Historic Register, the home was built 1851 by Milton & John Curtiss who e...	4 beds \| 3 baths \| 2,818 sq.ft.	$1,550,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 1.25% Airbnb Rental Income: $5960 Traditional Rental Income: $4027 Airbnb ROI: 1.77% Traditional ROI: 1.25%
16 Brookside Drive Easton , CT Welcome to 16 Brookside Drive situated on 3 acres located in the heart of Easton. Built in...	3 beds \| 4 baths \| 2,937 sq.ft.	$749,999	Airbnb cash on cash: 3.69% Traditional cash on cash: 3.17% Airbnb Rental Income: $5762 Traditional Rental Income: $4244 Airbnb ROI: 3.69% 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.	$389,900	Airbnb cash on cash: 9.04% Traditional cash on cash: 6.45% Airbnb Rental Income: $5292 Traditional Rental Income: $3276 Airbnb ROI: 9.04% Traditional ROI: 6.45%
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: 5.75% Traditional cash on cash: 4.95% Airbnb Rental Income: $4791 Traditional Rental Income: $3431 Airbnb ROI: 5.75% Traditional ROI: 4.95%
70 Cedar Hill Road Guilford , CT Experience the ultimate retreat in this stunning ranch home, nestled in Guilford Lakes Com...	4 beds \| 2 baths \| 1,814 sq.ft.	$450,000	Airbnb cash on cash: 6.12% Traditional cash on cash: 5.76% Airbnb Rental Income: $4510 Traditional Rental Income: $3418 Airbnb ROI: 6.12% Traditional ROI: 5.76%
116 Wellers Bridge Road Roxbury , CT Extra special and super sleek Mid-Century modern in a convenient Roxbury location. Cool ma...	3 beds \| 4 baths \| 3,236 sq.ft.	$1,195,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 2.94% Airbnb Rental Income: $7276 Traditional Rental Income: $4927 Airbnb ROI: 3.8% Traditional ROI: 2.94%
21 Holiday Point Road Sherman , CT [ONE OF A KIND] This house has it all. Located in the desired Atchison Cove private lake c...	4 beds \| 4 baths \| 4,854 sq.ft.	$1,250,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 2.01% Airbnb Rental Income: $7631 Traditional Rental Income: $4747 Airbnb ROI: 3.24% Traditional ROI: 2.01%
6 Bittersweet Drive Ledyard , CT Spectacular 4 BR, 3 full bath, Post & Beam style center chimney Cape Cod built in 1988 is ...	4 beds \| 3 baths \| 2,464 sq.ft.	$500,000	Airbnb cash on cash: 6.72% Traditional cash on cash: 6.11% Airbnb Rental Income: $5517 Traditional Rental Income: $4122 Airbnb ROI: 6.72% Traditional ROI: 6.11%
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: 7.95% Traditional cash on cash: 6.83% Airbnb Rental Income: $4476 Traditional Rental Income: $3204 Airbnb ROI: 7.95% Traditional ROI: 6.83%
25 Pleasant Street Ansonia , CT Originally built in 1890, it has since been remodeled. It is situated in a cul-de-sac. It ...	3 beds \| 2 baths \| 1,476 sq.ft.	$345,000	Airbnb cash on cash: 8.18% Traditional cash on cash: 6.06% Airbnb Rental Income: $4355 Traditional Rental Income: $2753 Airbnb ROI: 8.18% Traditional ROI: 6.06%

Vacation Rentals in Windsor

There are 4 vacation rental properties available for sale in the city of Windsor . The median list price of Airbnb properties available for sale in Windsor is $319,000 and the average price per square foot is $212. The cash on cash return on vacation rentals in Windsor is 5.00%. The average monthly short term rental income in Windsor is $3,346.

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

There are 4 Airbnb properties available for sale in Windsor.

In 2025, the best neighborhood to buy short term rental property is Windsor.

In January 2025, the average Airbnb occupancy rate in Windsor is 60%.

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

Your search for investment property begins and ends here

Airbnb For Sale in Windsor, CT

281 MOUNTAIN ROAD

Windsor, CT

3 beds | 2 baths | 1,132 sq.ft.

$230,000

Airbnb cash on cash: 8.41%

Traditional cash on cash: 6.82%

Airbnb Rental Income: $3346

Traditional Rental Income: $2253

Airbnb ROI: 8.41%

Traditional ROI: 6.82%

83 Corey Street

Windsor, CT

3 beds | 2 baths | 1,306 sq.ft.

$375,000

Airbnb cash on cash: 4.01%

Traditional cash on cash: 2.79%

Airbnb Rental Income: $3346

Traditional Rental Income: $2170

Airbnb ROI: 4.01%

Traditional ROI: 2.79%

25 Sunnyside Circle

Windsor, CT

3 beds | 2 baths | 1,075 sq.ft.

$269,000

Airbnb cash on cash: 6.77%

Traditional cash on cash: 6.56%

Airbnb Rental Income: $3346

Traditional Rental Income: $2547

Airbnb ROI: 6.77%

Traditional ROI: 6.56%

690 Bloomfield Avenue

Windsor, CT

3 beds | 1 baths | 1,110 sq.ft.

$249,900

Airbnb cash on cash: 7.51%

Traditional cash on cash: 6.07%

Airbnb Rental Income: $3346

Traditional Rental Income: $2259

Airbnb ROI: 7.51%

Traditional ROI: 6.07%

Airbnb Properties for Sale in Other Cities of Connecticut

Cornwall , CT

3 beds | 3 baths | 2,268 sq.ft.

$499,000

Airbnb cash on cash: 6.65%

Traditional cash on cash: 6.17%

Airbnb Rental Income: $5100

Traditional Rental Income: $3837

Airbnb ROI: 6.65%

Traditional ROI: 6.17%

Waterbury , CT

2 beds | 1 baths | 960 sq.ft.

$279,900

Airbnb cash on cash: 4.19%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $2546

Traditional Rental Income: $1898

Airbnb ROI: 4.19%

Traditional ROI: 4.06%

Plymouth , CT

3 beds | 2 baths | 1,768 sq.ft.

$424,900

Airbnb cash on cash: 6.95%

Traditional cash on cash: 5.33%

Airbnb Rental Income: $4791

Traditional Rental Income: $3156

Airbnb ROI: 6.95%

Traditional ROI: 5.33%

Bridgeport , CT

4 beds | 2 baths | 1,920 sq.ft.

$385,000

Airbnb cash on cash: 7.63%

Traditional cash on cash: 6.37%

Airbnb Rental Income: $4777

Traditional Rental Income: $3339

Airbnb ROI: 7.63%

Traditional ROI: 6.37%

Waterford , CT

3 beds | 1 baths | 1,202 sq.ft.