Real Estate Investment Properties for Sale in New Canaan, CT

Looking for investment property in New Canaan, CT with high ROI ?

Explore a variety of short-term homes & houses in New Canaan, CT. Invest wisely with VRBO & New Canaan, CT Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in New Canaan, CT

Search for Single Family Residential for Sale in New Canaan, Connecticut. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 18 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
60 East Avenue New Canaan, CT Charming in-town home with private yard and terrace. Bright open kitchen with attached liv...	3 beds \| 2 baths \| 2,352 sq.ft.	$1,149,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 1.5% Airbnb Rental Income: $3521 Traditional Rental Income: $3564 Airbnb ROI: 0.73% Traditional ROI: 1.5%
171 Proprietors Crossing New Canaan, CT Just renovated to perfection, this 5BR, 3.5BA classic Connecticut colonial with extra 1900...	5 beds \| 4 baths \| 5,748 sq.ft.	$2,675,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.32% Airbnb Rental Income: $null Traditional Rental Income: $7069 Airbnb ROI: N/A Traditional ROI: -0.32%
317 Park Street New Canaan, CT Luxury New Construction in the Heart of New Canaan! Experience the finest in modern liv...	5 beds \| 8 baths \| 6,624 sq.ft.	$3,750,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.18% Airbnb Rental Income: $null Traditional Rental Income: $10350 Airbnb ROI: N/A Traditional ROI: -0.18%
354 South Avenue New Canaan, CT Experience extraordinary living in this sophisticated, estate-style majestic brick townhou...	5 beds \| 8 baths \| 7,505 sq.ft.	$5,500,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.12% Airbnb Rental Income: $null Traditional Rental Income: $10376 Airbnb ROI: N/A Traditional ROI: -1.12%
31 Selleck Place New Canaan, CT Welcome to 31 Selleck Place -- a captivating vintage Colonial in a fabulous location (half...	4 beds \| 3 baths \| 2,076 sq.ft.	$1,550,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 0.26% Airbnb Rental Income: $3354 Traditional Rental Income: $4980 Airbnb ROI: -1.38% Traditional ROI: 0.26%
202 Weed Street New Canaan, CT A unique collaboration between past and present, 202 Weed Street is a 4,628 sq ft Colonial...	5 beds \| 4 baths \| 4,628 sq.ft.	$2,195,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.09% Airbnb Rental Income: $null Traditional Rental Income: $6648 Airbnb ROI: N/A Traditional ROI: 0.09%
216 White Oak Shade Road New Canaan, CT Experience the perfect blend of historic charm and modern living in this beautifully renov...	4 beds \| 4 baths \| 2,404 sq.ft.	$1,695,000	Airbnb cash on cash: -1.53% Traditional cash on cash: 0.08% Airbnb Rental Income: $3354 Traditional Rental Income: $5148 Airbnb ROI: -1.53% Traditional ROI: 0.08%
650 Laurel Road New Canaan, CT Through stone columns along a scenic approach is this first time on market custom-built fi...	5 beds \| 5 baths \| 6,144 sq.ft.	$2,850,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.48% Airbnb Rental Income: $null Traditional Rental Income: $9655 Airbnb ROI: N/A Traditional ROI: 0.48%
565 Oenoke Ridge New Canaan, CT Experience Architectural History: The Celebrated Celanese House. This is your chance to ...	4 beds \| 5 baths \| 4,927 sq.ft.	$4,400,000	Airbnb cash on cash: -2.52% Traditional cash on cash: -0.84% Airbnb Rental Income: $3354 Traditional Rental Income: $9454 Airbnb ROI: -2.52% Traditional ROI: -0.84%
63 Middle Ridge Road New Canaan, CT Expanded and fully renovated in 2005, this exceptional Colonial is located in the prestigi...	5 beds \| 6 baths \| 7,822 sq.ft.	$3,895,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.38% Airbnb Rental Income: $null Traditional Rental Income: $10042 Airbnb ROI: N/A Traditional ROI: -0.38%
25 Gower Street New Canaan, CT Luxury New Construction in the Heart of New Canaan! Coming Soon 2026! Experience the fin...	5 beds \| 8 baths \| 6,322 sq.ft.	$4,600,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.85% Airbnb Rental Income: $null Traditional Rental Income: $9830 Airbnb ROI: N/A Traditional ROI: -0.85%
51 Reeder Lane New Canaan, CT Situated on over two acres on one of New Canaan's most coveted cul-de-sacs, this five-bedr...	5 beds \| 4 baths \| 3,382 sq.ft.	$2,495,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.13% Airbnb Rental Income: $null Traditional Rental Income: $7037 Airbnb ROI: N/A Traditional ROI: -0.13%
104 Ramhorne Road New Canaan, CT Come delight in seeing an exceptional New Canaan residence designed with style, sophistica...	4 beds \| 6 baths \| 3,985 sq.ft.	$2,495,000	Airbnb cash on cash: -2.05% Traditional cash on cash: 1.33% Airbnb Rental Income: $3354 Traditional Rental Income: $10424 Airbnb ROI: -2.05% Traditional ROI: 1.33%
204 Parade Hill Road New Canaan, CT Historic Canaan Parish Gem! Originally built in 1775, this remarkable property began it's ...	4 beds \| 5 baths \| 3,260 sq.ft.	$2,595,000	Airbnb cash on cash: -2.09% Traditional cash on cash: 0.35% Airbnb Rental Income: $3354 Traditional Rental Income: $8483 Airbnb ROI: -2.09% Traditional ROI: 0.35%
234 Marvin Ridge Road New Canaan, CT Nestled on 1 beautifully landscaped acre, this charming 3 bed, 2 bath one level home is a ...	3 beds \| 2 baths \| 2,175 sq.ft.	$1,350,000	Airbnb cash on cash: -1.02% Traditional cash on cash: -0.1% Airbnb Rental Income: $3521 Traditional Rental Income: $3897 Airbnb ROI: -1.02% Traditional ROI: -0.1%
331 Dans Highway New Canaan, CT 1936 Vintage Colonial Home is sited high on over 6 acres of private land in the estate sec...	5 beds \| 5 baths \| 4,554 sq.ft.	$2,195,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.41% Airbnb Rental Income: $null Traditional Rental Income: $9336 Airbnb ROI: N/A Traditional ROI: 1.41%
139 Jelliff Mill Road New Canaan, CT Custom designed luxury home offering uncompromising quality and functionality throughout. ...	5 beds \| 8 baths \| 6,075 sq.ft.	$2,375,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.27% Airbnb Rental Income: $null Traditional Rental Income: $9786 Airbnb ROI: N/A Traditional ROI: 1.27%
12 Lincoln Drive New Canaan, CT HIGHEST AND BEST DUE BY SATURDAY DEC 6TH 5PM. Welcome to this inviting four-bedroom high r...	4 beds \| 2 baths \| 2,156 sq.ft.	$1,095,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 0.82% Airbnb Rental Income: $3354 Traditional Rental Income: $4116 Airbnb ROI: -0.66% Traditional ROI: 0.82%

Your search for investment property begins and ends here

Single Family Homes for Sale in New Canaan, CT

60 East Avenue

New Canaan, CT

3 beds | 2 baths | 2,352 sq.ft.

$1,149,000

Airbnb cash on cash: 0.73%

Traditional cash on cash: 1.5%

Airbnb Rental Income: $3521

Traditional Rental Income: $3564

Airbnb ROI: 0.73%

Traditional ROI: 1.5%

171 Proprietors Crossing

New Canaan, CT

5 beds | 4 baths | 5,748 sq.ft.

$2,675,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.32%

Airbnb Rental Income: $null

Traditional Rental Income: $7069

Airbnb ROI: N/A

Traditional ROI: -0.32%

317 Park Street

New Canaan, CT

5 beds | 8 baths | 6,624 sq.ft.

$3,750,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.18%

Airbnb Rental Income: $null

Traditional Rental Income: $10350

Airbnb ROI: N/A

Traditional ROI: -0.18%

354 South Avenue

New Canaan, CT

5 beds | 8 baths | 7,505 sq.ft.

$5,500,000

Airbnb cash on cash: N/A

Traditional cash on cash: -1.12%

Airbnb Rental Income: $null

Traditional Rental Income: $10376

Airbnb ROI: N/A

Traditional ROI: -1.12%

31 Selleck Place

New Canaan, CT

4 beds | 3 baths | 2,076 sq.ft.

$1,550,000

Airbnb cash on cash: -1.38%

Traditional cash on cash: 0.26%

Airbnb Rental Income: $3354

Traditional Rental Income: $4980

Airbnb ROI: -1.38%

Traditional ROI: 0.26%

202 Weed Street

New Canaan, CT

5 beds | 4 baths | 4,628 sq.ft.

$2,195,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.09%

Airbnb Rental Income: $null

Traditional Rental Income: $6648

Airbnb ROI: N/A

Traditional ROI: 0.09%

216 White Oak Shade Road

New Canaan, CT

4 beds | 4 baths | 2,404 sq.ft.

$1,695,000

Airbnb cash on cash: -1.53%

Traditional cash on cash: 0.08%

Airbnb Rental Income: $3354

Traditional Rental Income: $5148

Airbnb ROI: -1.53%

Traditional ROI: 0.08%

650 Laurel Road

New Canaan, CT

5 beds | 5 baths | 6,144 sq.ft.

$2,850,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.48%

Airbnb Rental Income: $null

Traditional Rental Income: $9655

Airbnb ROI: N/A