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.

Investment Property for Sale in New Canaan, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
160 Park Street unit: 102 #102 New Canaan, CT Experience the epitome of luxury living in this stunning and sophisticated 3Bd/3.5Bth cond...	3 beds \| 4 baths \| 2,402 sq.ft.	$3,100,000	Airbnb cash on cash: -1.92% Traditional cash on cash: -0.87% Airbnb Rental Income: $3521 Traditional Rental Income: $5765 Airbnb ROI: -1.92% Traditional ROI: -0.87%
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 \| 1,400 sq.ft.	$1,000,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 1.78% Airbnb Rental Income: $3521 Traditional Rental Income: $3564 Airbnb ROI: 0.9% Traditional ROI: 1.78%
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: 1.17% Airbnb Rental Income: $null Traditional Rental Income: $7069 Airbnb ROI: N/A Traditional ROI: 1.17%
317 Park Street New Canaan, CT Luxury New Construction in the Heart of New Canaan! Experience the finest in modern living...	5 beds \| 8 baths \| 6,624 sq.ft.	$3,750,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.99% Airbnb Rental Income: $null Traditional Rental Income: $10350 Airbnb ROI: N/A Traditional ROI: 0.99%
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: 0.13% Airbnb Rental Income: $null Traditional Rental Income: $10376 Airbnb ROI: N/A Traditional ROI: 0.13%
565 Oenoke Rdg New Canaan, CT Experience Architectural History: The Celebrated Celanese House. This is your chance to ow...	4 beds \| 4 baths \| 4,927 sq.ft.	$4,400,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 0.36% Airbnb Rental Income: $3354 Traditional Rental Income: $9454 Airbnb ROI: -1.32% Traditional ROI: 0.36%
25 Gower Street New Canaan, CT Luxury New Construction in the Heart of New Canaan! Coming Soon 2026! Experience the fines...	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%
15 Burtis Avenue unit: East Plaza 203 #East Plaza 203 New Canaan, CT In the heart of New Canaan, The Quartier presents 21 bespoke luxury residences that pairs ...	2 beds \| 3 baths \| 1,525 sq.ft.	$2,395,000	Airbnb cash on cash: -3.26% Traditional cash on cash: -1.94% Airbnb Rental Income: $1213 Traditional Rental Income: $3771 Airbnb ROI: -3.26% Traditional ROI: -1.94%
15 Burtis Avenue unit: West Penthouse B #West Penthouse B New Canaan, CT In the heart of New Canaan, The Quartier presents 21 bespoke luxury residences that pairs ...	3 beds \| 3 baths \| 2,494 sq.ft.	$4,495,000	Airbnb cash on cash: -2.88% Traditional cash on cash: -2.44% Airbnb Rental Income: $3521 Traditional Rental Income: $4578 Airbnb ROI: -2.88% Traditional ROI: -2.44%
15 Burtis Avenue unit: Townhome A #Townhome A New Canaan, CT In the heart of New Canaan, The Quartier presents 21 bespoke luxury residences that pairs ...	3 beds \| 3 baths \| 1,767 sq.ft.	$2,895,000	Airbnb cash on cash: -2.59% Traditional cash on cash: -2.07% Airbnb Rental Income: $3521 Traditional Rental Income: $4128 Airbnb ROI: -2.59% Traditional ROI: -2.07%
15 Burtis Avenue unit: Townhome D #Townhome D New Canaan, CT In the heart of New Canaan, The Quartier presents 21 bespoke luxury residences that pairs ...	2 beds \| 4 baths \| 2,174 sq.ft.	$3,195,000	Airbnb cash on cash: -3.38% Traditional cash on cash: -2.04% Airbnb Rental Income: $1213 Traditional Rental Income: $4795 Airbnb ROI: -3.38% Traditional ROI: -2.04%
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: 1.06% Airbnb Rental Income: $null Traditional Rental Income: $7037 Airbnb ROI: N/A Traditional ROI: 1.06%
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: -0.79% Traditional cash on cash: 2.58% Airbnb Rental Income: $3354 Traditional Rental Income: $10424 Airbnb ROI: -0.79% Traditional ROI: 2.58%
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: 2.09% Airbnb Rental Income: $null Traditional Rental Income: $9786 Airbnb ROI: N/A Traditional ROI: 2.09%
15 Burtis Avenue unit: Townhome B #Townhome B New Canaan, CT In the heart of New Canaan, The Quartier presents 21 bespoke luxury residences that pairs ...	3 beds \| 4 baths \| 3,261 sq.ft.	$6,095,000	Airbnb cash on cash: -3.08% Traditional cash on cash: -2.57% Airbnb Rental Income: $3521 Traditional Rental Income: $5670 Airbnb ROI: -3.08% Traditional ROI: -2.57%
47 Bank Street unit: 47 #47 New Canaan, CT Experience the perfect blend of luxury and convenience with this stunning Leefair Ranch co...	2 beds \| 4 baths \| 2,684 sq.ft.	$1,395,000	Airbnb cash on cash: -1.89% Traditional cash on cash: 1.37% Airbnb Rental Income: $1213 Traditional Rental Income: $5053 Airbnb ROI: -1.89% Traditional ROI: 1.37%
15 Burtis Avenue unit: East Penthouse A #East Penthouse A New Canaan, CT In the heart of New Canaan, The Quartier presents 21 bespoke luxury residences that pairs ...	3 beds \| 4 baths \| 2,938 sq.ft.	$5,995,000	Airbnb cash on cash: -2.99% Traditional cash on cash: -2.47% Airbnb Rental Income: $3521 Traditional Rental Income: $5663 Airbnb ROI: -2.99% Traditional ROI: -2.47%
42 Hillcrest Road New Canaan, CT A masterpiece of modern luxury, this 8,400 sq ft estate by Arena Development has been meti...	5 beds \| 8 baths \| 8,534 sq.ft.	$4,999,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.36% Airbnb Rental Income: $null Traditional Rental Income: $10056 Airbnb ROI: N/A Traditional ROI: 0.36%
295 Brushy Ridge Road New Canaan, CT Experience the perfect synergy of classic New England charm and forward-thinking design in...	5 beds \| 7 baths \| 6,705 sq.ft.	$3,695,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.23% Airbnb Rental Income: $null Traditional Rental Income: $10665 Airbnb ROI: N/A Traditional ROI: 1.23%

Real Estate investment in New-canaan, CT

There are 22 properties for sale in the city of New Canaan . The median list price in New Canaan is $2,895,000 and the average price per square foot is $720. In February 2026, the average monthly cash on cash return in New Canaan is 1.00%. The average monthly rental income in New Canaan is $6,648.

New-canaan, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 22 investment properties available for sale in New-canaan.

In 2026, the best neighborhood to buy investment property is New Canaan.

The ROI for Long-Term is higher than the Short-Term in New-canaan with average rental income of $6,648.

Your search for investment property begins and ends here

Investment Property for Sale in New Canaan, CT

160 Park Street unit: 102 #102

New Canaan, CT

3 beds | 4 baths | 2,402 sq.ft.

$3,100,000

Airbnb cash on cash: -1.92%

Traditional cash on cash: -0.87%

Airbnb Rental Income: $3521

Traditional Rental Income: $5765

Airbnb ROI: -1.92%

Traditional ROI: -0.87%

60 East Avenue

New Canaan, CT

3 beds | 2 baths | 1,400 sq.ft.

$1,000,000

Airbnb cash on cash: 0.9%

Traditional cash on cash: 1.78%

Airbnb Rental Income: $3521

Traditional Rental Income: $3564

Airbnb ROI: 0.9%

Traditional ROI: 1.78%

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: 1.17%

Airbnb Rental Income: $null

Traditional Rental Income: $7069

Airbnb ROI: N/A

Traditional ROI: 1.17%

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: 0.99%

Airbnb Rental Income: $null

Traditional Rental Income: $10350

Airbnb ROI: N/A

Traditional ROI: 0.99%

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: 0.13%

Airbnb Rental Income: $null

Traditional Rental Income: $10376

Airbnb ROI: N/A

Traditional ROI: 0.13%

565 Oenoke Rdg

New Canaan, CT

4 beds | 4 baths | 4,927 sq.ft.

$4,400,000

Airbnb cash on cash: -1.32%

Traditional cash on cash: 0.36%

Airbnb Rental Income: $3354

Traditional Rental Income: $9454

Airbnb ROI: -1.32%

Traditional ROI: 0.36%

25 Gower Street

New Canaan, CT

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%

15 Burtis Avenue unit: East Plaza 203 #East Plaza 203

New Canaan, CT

2 beds | 3 baths | 1,525 sq.ft.

$2,395,000

Airbnb cash on cash: -3.26%

Traditional cash on cash: -1.94%

Airbnb Rental Income: $1213

Traditional Rental Income: $3771

Airbnb ROI: -3.26%