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
55 New Norwalk Road New Canaan, CT Also known as 161 Forest St. which is the front entrance. Official address is 55 New Norwa...	5 beds \| 4 baths \| 1,900 sq.ft.	$1,250,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 2.04% Airbnb Rental Income: $4413 Traditional Rental Income: $4659 Airbnb ROI: 1.04% Traditional ROI: 2.04%
100 Harrison Avenue New Canaan, CT Versatile Gem: Walkable and with Income Potential - This light-filled Cape Cod offers a ra...	4 beds \| 3 baths \| 2,635 sq.ft.	$1,795,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 1.21% Airbnb Rental Income: $3363 Traditional Rental Income: $5186 Airbnb ROI: -0.34% Traditional ROI: 1.21%
302 Gramercy Park unit: 302 New Canaan, CT Welcome to Gramercy Park! Exquisite, boutique enclave of ten luxury residences nestled in ...	3 beds \| 4 baths \| 2,417 sq.ft.	$2,595,000	Airbnb cash on cash: -2.13% Traditional cash on cash: -0.55% Airbnb Rental Income: $2260 Traditional Rental Income: $5500 Airbnb ROI: -2.13% Traditional ROI: -0.55%
7 Kimberly Place New Canaan, CT Gracious and light-filled, this stunning 5200 sq ft. classic, located on coveted Kimberly ...	5 beds \| 5 baths \| 5,249 sq.ft.	$3,495,000	Airbnb cash on cash: -0.57% Traditional cash on cash: 1% Airbnb Rental Income: $4413 Traditional Rental Income: $8590 Airbnb ROI: -0.57% Traditional ROI: 1%
160 Park Street unit: 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: -2.29% Traditional cash on cash: -0.87% Airbnb Rental Income: $2260 Traditional Rental Income: $5765 Airbnb ROI: -2.29% Traditional ROI: -0.87%
41 Lake Wind Road New Canaan, CT Set on a beautifully scenic 2.35-acre lot on a tranquil circle near Laurel Reservoir, this...	5 beds \| 6 baths \| 6,313 sq.ft.	$2,395,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 3.37% Airbnb Rental Income: $4413 Traditional Rental Income: $12189 Airbnb ROI: -0.55% Traditional ROI: 3.37%
48 Green Meadow Lane New Canaan, CT Experience the pinnacle of New Canaan modernism at 48 Green Meadow, a 4,400+ sq ft archite...	5 beds \| 5 baths \| 4,454 sq.ft.	$2,995,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 1.98% Airbnb Rental Income: $4413 Traditional Rental Income: $11163 Airbnb ROI: -0.79% Traditional ROI: 1.98%
171 Proprietors Crossing New Canaan, CT Updated to perfection, this classic 5-bedroom Connecticut Colonial offers over 5,500 squar...	5 beds \| 4 baths \| 5,532 sq.ft.	$2,795,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 1.07% Airbnb Rental Income: $4413 Traditional Rental Income: $7069 Airbnb ROI: -0.31% Traditional ROI: 1.07%
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: -0.15% Traditional cash on cash: 1.4% Airbnb Rental Income: $4413 Traditional Rental Income: $6648 Airbnb ROI: -0.15% Traditional ROI: 1.4%
565 Oenoke Ridge New Canaan, CT Experience Architectural History: The Celebrated Celanese House. This is your chance to ow...	4 beds \| 5 baths \| 4,927 sq.ft.	$4,400,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 0.36% Airbnb Rental Income: $3363 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: -2.34% Traditional cash on cash: -0.85% Airbnb Rental Income: $4413 Traditional Rental Income: $9830 Airbnb ROI: -2.34% Traditional ROI: -0.85%
15 Burtis Avenue #East Penthouse C New Canaan, CT The Quartier reimagines timeless luxury through 21 bespoke residences. Experience the rare...	3 beds \| 4 baths \| 3,322 sq.ft.	$5,995,000	Airbnb cash on cash: -3.24% Traditional cash on cash: -2.53% Airbnb Rental Income: $2260 Traditional Rental Income: $5671 Airbnb ROI: -3.24% Traditional ROI: -2.53%
15 Burtis Avenue unit: 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: -3.27% Traditional cash on cash: -2.57% Airbnb Rental Income: $2260 Traditional Rental Income: $5670 Airbnb ROI: -3.27% Traditional ROI: -2.57%
98 Indian Waters Drive New Canaan, CT Completely and thoughtfully renovated, this exceptional New Canaan residence blends timele...	5 beds \| 8 baths \| 7,870 sq.ft.	$4,195,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 0.97% Airbnb Rental Income: $4413 Traditional Rental Income: $11135 Airbnb ROI: -0.99% Traditional ROI: 0.97%
15 Burtis Avenue #East Plaza 203 New Canaan, CT Sustainable Chic Meets Village Charm: The Ultimate New Canaan Flat. - Discover the perfect...	2 beds \| 3 baths \| 1,555 sq.ft.	$2,395,000	Airbnb cash on cash: -2.76% Traditional cash on cash: -1.68% Airbnb Rental Income: $1343 Traditional Rental Income: $3320 Airbnb ROI: -2.76% Traditional ROI: -1.68%
15 Burtis Avenue #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.	$2,995,000	Airbnb cash on cash: -2.56% Traditional cash on cash: -1.8% Airbnb Rental Income: $2260 Traditional Rental Income: $3791 Airbnb ROI: -2.56% Traditional ROI: -1.8%
15 Burtis Avenue #West Penthouse B New Canaan, CT The Pinnacle of Village Sophistication: The Penthouse at The Quartier. At the heart of dow...	3 beds \| 3 baths \| 2,494 sq.ft.	$4,495,000	Airbnb cash on cash: -2.75% Traditional cash on cash: -2.08% Airbnb Rental Income: $2260 Traditional Rental Income: $4476 Airbnb ROI: -2.75% Traditional ROI: -2.08%
15 Burtis Avenue #East Plaza 206 New Canaan, CT Effortless Luxury: The Modern Flat at The Quartier - timeless luxury through 21 bespoke re...	2 beds \| 3 baths \| 1,292 sq.ft.	$1,995,000	Airbnb cash on cash: -3.19% Traditional cash on cash: -1.63% Airbnb Rental Income: $1343 Traditional Rental Income: $3812 Airbnb ROI: -3.19% Traditional ROI: -1.63%
15 Burtis Avenue #Townhome C New Canaan, CT Elevated Modernity in the Heart of New Canaan - Nestled in the vibrant center of New Canaa...	2 beds \| 4 baths \| 2,507 sq.ft.	$4,200,000	Airbnb cash on cash: -3.55% Traditional cash on cash: -2.36% Airbnb Rental Income: $1343 Traditional Rental Income: $5542 Airbnb ROI: -3.55% Traditional ROI: -2.36%
792 N Wilton Road New Canaan, CT Exceptional 1998 colonial on 2.3 pristine, level acres with circular drive and rare 6-car ...	5 beds \| 5 baths \| 5,038 sq.ft.	$2,895,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.47% Airbnb Rental Income: $4413 Traditional Rental Income: $8976 Airbnb ROI: -0.58% Traditional ROI: 1.47%
143 Oenoke Ridge New Canaan, CT Experience the pinnacle of sophisticated living in this extraordinary estate by renowned b...	5 beds \| 8 baths \| 8,022 sq.ft.	$5,995,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 0.03% Airbnb Rental Income: $4413 Traditional Rental Income: $10463 Airbnb ROI: -1.23% Traditional ROI: 0.03%
374 Michigan Road New Canaan, CT Privately set on 3.2 picturesque acres, this distinguished 5-bedroom, 4.5-bath residence b...	5 beds \| 5 baths \| 5,674 sq.ft.	$2,795,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 1.77% Airbnb Rental Income: $4413 Traditional Rental Income: $9081 Airbnb ROI: -0.39% Traditional ROI: 1.77%
111 Heritage Hill Road #111 New Canaan, CT Fabulous corner-unit townhome in the heart of New Canaan. This bright and beautifully upda...	3 beds \| 3 baths \| 1,616 sq.ft.	$849,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 2.56% Airbnb Rental Income: $2260 Traditional Rental Income: $3604 Airbnb ROI: 0.14% Traditional ROI: 2.56%
47 Bank Street unit: 47 New Canaan, CT Experience the perfect blend of luxury and convenience with this stunning Leefair Ranch co...	2 beds \| 3 baths \| 2,285 sq.ft.	$1,499,000	Airbnb cash on cash: -1.22% Traditional cash on cash: 1.02% Airbnb Rental Income: $1343 Traditional Rental Income: $4054 Airbnb ROI: -1.22% Traditional ROI: 1.02%
26 Farm Road New Canaan, CT Storybook charm meets modern living in the heart of New Canaan! Ideally located just steps...	5 beds \| 5 baths \| 5,076 sq.ft.	$2,695,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 1.69% Airbnb Rental Income: $4413 Traditional Rental Income: $8748 Airbnb ROI: -0.41% Traditional ROI: 1.69%
533 Old Stamford Road New Canaan, CT Welcome to the Original Norman Dairy Farmhouse, where 1900s craftsmanship meets 21st-centu...	5 beds \| 4 baths \| 4,458 sq.ft.	$1,549,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 2.51% Airbnb Rental Income: $4413 Traditional Rental Income: $6327 Airbnb ROI: 0.54% Traditional ROI: 2.51%
736 Old Stamford Road New Canaan, CT Darien Beach rights and New Canaan Schools make this a very special offering! Storybook ch...	4 beds \| 4 baths \| 2,673 sq.ft.	$1,650,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 2.31% Airbnb Rental Income: $3363 Traditional Rental Income: $6440 Airbnb ROI: -0.19% Traditional ROI: 2.31%
30 Elm Place New Canaan, CT Modern Luxury Meets Classic Charm on Elm Place - Experience sophisticated living in this s...	5 beds \| 5 baths \| 5,116 sq.ft.	$3,895,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 0.69% Airbnb Rental Income: $4413 Traditional Rental Income: $8617 Airbnb ROI: -0.73% Traditional ROI: 0.69%
35 Danvers Lane New Canaan, CT An exceptional opportunity to own in the desirable South of the YMCA neighborhood featurin...	4 beds \| 5 baths \| 4,980 sq.ft.	$3,100,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 1.29% Airbnb Rental Income: $3363 Traditional Rental Income: $8976 Airbnb ROI: -0.92% Traditional ROI: 1.29%
39 Park Place #39 New Canaan, CT Rich in warmth and history, this enchanting antique gable-front home has been thoroughly u...	3 beds \| 3 baths \| 2,393 sq.ft.	$1,395,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 1.66% Airbnb Rental Income: $2260 Traditional Rental Income: $4328 Airbnb ROI: -0.37% Traditional ROI: 1.66%
60 Heritage Hill Road #Apt A New Canaan, CT Garage Unit Included. Located in the most desirable corner of the community and sitting hi...	1 beds \| 1 baths \| 798 sq.ft.	$469,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 2.83% Airbnb Rental Income: $1123 Traditional Rental Income: $2091 Airbnb ROI: -0.24% Traditional ROI: 2.83%
1541 Oenoke Ridge New Canaan, CT Welcome to 1541 Oenoke Ridge, a spectacular country retreat with unparalleled privacy and ...	5 beds \| 6 baths \| 5,687 sq.ft.	$2,995,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 1.92% Airbnb Rental Income: $4413 Traditional Rental Income: $10607 Airbnb ROI: -0.65% Traditional ROI: 1.92%
46 Wakeman Road New Canaan, CT Nestled on a quiet cul-de-sac on a private lane, 46 Wakeman Road is a quintessential Count...	4 beds \| 6 baths \| 6,950 sq.ft.	$2,995,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 1.75% Airbnb Rental Income: $3363 Traditional Rental Income: $10309 Airbnb ROI: -1.02% Traditional ROI: 1.75%
224 Marvin Ridge Road New Canaan, CT Hurry to see this New Canaan charmer! Custom designed and meticulously maintained by the s...	3 beds \| 3 baths \| 3,122 sq.ft.	$1,500,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 1.65% Airbnb Rental Income: $2260 Traditional Rental Income: $4971 Airbnb ROI: -0.7% Traditional ROI: 1.65%
15 Burtis Avenue #East Plaza 202 New Canaan, CT Sustainable Chic Meets Village Charm: The Ultimate New Canaan duplex - Discover the perfec...	2 beds \| 3 baths \| 1,641 sq.ft.	$2,850,000	Airbnb cash on cash: -2.82% Traditional cash on cash: -1.78% Airbnb Rental Income: $1343 Traditional Rental Income: $3681 Airbnb ROI: -2.82% Traditional ROI: -1.78%
15 Burtis Avenue #East Penthouse B New Canaan, CT The Quartier reimagines timeless luxury through 21 bespoke residences. Experience the rare...	3 beds \| 4 baths \| 3,292 sq.ft.	$5,595,000	Airbnb cash on cash: -2.82% Traditional cash on cash: -2.08% Airbnb Rental Income: $2260 Traditional Rental Income: $5557 Airbnb ROI: -2.82% Traditional ROI: -2.08%
15 Burtis Avenue #West Plaza 202 New Canaan, CT Effortless Luxury: The Modern Flat at The Quartier - timeless luxury through 21 bespoke re...	2 beds \| 3 baths \| 2,140 sq.ft.	$3,300,000	Airbnb cash on cash: -2.86% Traditional cash on cash: -1.64% Airbnb Rental Income: $1343 Traditional Rental Income: $4664 Airbnb ROI: -2.86% Traditional ROI: -1.64%

Real Estate investment in New-canaan, CT

There are 42 properties for sale in the city of New Canaan . The median list price in New Canaan is $2,795,000 and the average price per square foot is $761. In May 2026, the average monthly cash on cash return in New Canaan is 1.00%. The average monthly rental income in New Canaan is $5,670.

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

There are 42 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 $5,670.

Your search for investment property begins and ends here

Investment Property for Sale in New Canaan, CT

55 New Norwalk Road

New Canaan, CT

5 beds | 4 baths | 1,900 sq.ft.

$1,250,000

Airbnb cash on cash: 1.04%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $4413

Traditional Rental Income: $4659

Airbnb ROI: 1.04%

Traditional ROI: 2.04%

100 Harrison Avenue

New Canaan, CT

4 beds | 3 baths | 2,635 sq.ft.

$1,795,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 1.21%

Airbnb Rental Income: $3363

Traditional Rental Income: $5186

Airbnb ROI: -0.34%

Traditional ROI: 1.21%

302 Gramercy Park unit: 302

New Canaan, CT

3 beds | 4 baths | 2,417 sq.ft.

$2,595,000

Airbnb cash on cash: -2.13%

Traditional cash on cash: -0.55%

Airbnb Rental Income: $2260

Traditional Rental Income: $5500

Airbnb ROI: -2.13%

Traditional ROI: -0.55%

7 Kimberly Place

New Canaan, CT

5 beds | 5 baths | 5,249 sq.ft.

$3,495,000

Airbnb cash on cash: -0.57%

Traditional cash on cash: 1%

Airbnb Rental Income: $4413

Traditional Rental Income: $8590

Airbnb ROI: -0.57%

Traditional ROI: 1%

160 Park Street unit: 102

New Canaan, CT

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

$3,100,000

Airbnb cash on cash: -2.29%

Traditional cash on cash: -0.87%

Airbnb Rental Income: $2260

Traditional Rental Income: $5765

Airbnb ROI: -2.29%

Traditional ROI: -0.87%

41 Lake Wind Road

New Canaan, CT

5 beds | 6 baths | 6,313 sq.ft.

$2,395,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $4413

Traditional Rental Income: $12189

Airbnb ROI: -0.55%

Traditional ROI: 3.37%

48 Green Meadow Lane

New Canaan, CT

5 beds | 5 baths | 4,454 sq.ft.

$2,995,000

Airbnb cash on cash: -0.79%

Traditional cash on cash: 1.98%

Airbnb Rental Income: $4413

Traditional Rental Income: $11163

Airbnb ROI: -0.79%

Traditional ROI: 1.98%

171 Proprietors Crossing

New Canaan, CT

5 beds | 4 baths | 5,532 sq.ft.

$2,795,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 1.07%

Airbnb Rental Income: $4413

Traditional Rental Income: $7069

Airbnb ROI: -0.31%