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
2 Sleepy Hollow Road New Canaan, CT Discover this stunning five-bedroom contemporary on a premier quiet New Canaan cul-de-sac-...	5 beds \| 3 baths \| 5,658 sq.ft.	$2,195,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 0.94% Airbnb Rental Income: $5062 Traditional Rental Income: $5749 Airbnb ROI: 0.1% Traditional ROI: 0.94%
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.	$1,200,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 2.17% Airbnb Rental Income: $5062 Traditional Rental Income: $4659 Airbnb ROI: 1.61% Traditional ROI: 2.17%
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: 0.59% Traditional cash on cash: 1.21% Airbnb Rental Income: $5217 Traditional Rental Income: $5186 Airbnb ROI: 0.59% Traditional ROI: 1.21%
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: -0.4% Traditional cash on cash: 1% Airbnb Rental Income: $5062 Traditional Rental Income: $8590 Airbnb ROI: -0.4% Traditional ROI: 1%
160 Park Street #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: -2.21% Traditional cash on cash: -0.87% Airbnb Rental Income: $2539 Traditional Rental Income: $5765 Airbnb ROI: -2.21% 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: -0.31% Traditional cash on cash: 3.37% Airbnb Rental Income: $5062 Traditional Rental Income: $12189 Airbnb ROI: -0.31% Traditional ROI: 3.37%
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.	$2,650,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 1.19% Airbnb Rental Income: $5062 Traditional Rental Income: $7069 Airbnb ROI: -0.05% Traditional ROI: 1.19%
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: -2.21% Traditional cash on cash: -0.85% Airbnb Rental Income: $5062 Traditional Rental Income: $9830 Airbnb ROI: -2.21% 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: -3.2% Traditional cash on cash: -2.53% Airbnb Rental Income: $2539 Traditional Rental Income: $5671 Airbnb ROI: -3.2% Traditional ROI: -2.53%
15 Burtis Avenue #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: -3.23% Traditional cash on cash: -2.57% Airbnb Rental Income: $2539 Traditional Rental Income: $5670 Airbnb ROI: -3.23% Traditional ROI: -2.57%
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: -2.34% Traditional cash on cash: -1.68% Airbnb Rental Income: $2451 Traditional Rental Income: $3320 Airbnb ROI: -2.34% 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: -2.47% Traditional cash on cash: -1.8% Airbnb Rental Income: $2539 Traditional Rental Income: $3791 Airbnb ROI: -2.47% 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: -2.69% Traditional cash on cash: -2.08% Airbnb Rental Income: $2539 Traditional Rental Income: $4476 Airbnb ROI: -2.69% 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: -2.69% Traditional cash on cash: -1.63% Airbnb Rental Income: $2451 Traditional Rental Income: $3812 Airbnb ROI: -2.69% 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: -3.31% Traditional cash on cash: -2.36% Airbnb Rental Income: $2451 Traditional Rental Income: $5542 Airbnb ROI: -3.31% Traditional ROI: -2.36%
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: -1.13% Traditional cash on cash: 0.03% Airbnb Rental Income: $5062 Traditional Rental Income: $10463 Airbnb ROI: -1.13% Traditional ROI: 0.03%
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: 0.91% Traditional cash on cash: 2.51% Airbnb Rental Income: $5062 Traditional Rental Income: $6327 Airbnb ROI: 0.91% 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: 0.82% Traditional cash on cash: 2.31% Airbnb Rental Income: $5217 Traditional Rental Income: $6440 Airbnb ROI: 0.82% Traditional ROI: 2.31%
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: -2.47% Traditional cash on cash: -1.78% Airbnb Rental Income: $2451 Traditional Rental Income: $3681 Airbnb ROI: -2.47% 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: -2.78% Traditional cash on cash: -2.08% Airbnb Rental Income: $2539 Traditional Rental Income: $5557 Airbnb ROI: -2.78% 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: -2.56% Traditional cash on cash: -1.64% Airbnb Rental Income: $2451 Traditional Rental Income: $4664 Airbnb ROI: -2.56% Traditional ROI: -1.64%
24 Llewellyn Drive New Canaan, CT Modern Architectural Masterpiece - Nestled on 1.77 acres of lush, verdant grounds, this cu...	4 beds \| 5 baths \| 6,407 sq.ft.	$4,795,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 0.29% Airbnb Rental Income: $5217 Traditional Rental Income: $9210 Airbnb ROI: -0.85% Traditional ROI: 0.29%
45 Seminary Street New Canaan, CT IN TOWN LIVING! Gracefully set on a charming in-town street, this lovely 3-bedroom, 2.5-ba...	3 beds \| 3 baths \| 2,455 sq.ft.	$1,595,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 1.38% Airbnb Rental Income: $2539 Traditional Rental Income: $4723 Airbnb ROI: -0.51% Traditional ROI: 1.38%
32 E Hills Drive #32 New Canaan, CT Welcome home to this bright and beautifully updated 2-bedroom, 1.5-bath condo, perched at ...	2 beds \| 2 baths \| 864 sq.ft.	$555,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 2.96% Airbnb Rental Income: $2451 Traditional Rental Income: $2636 Airbnb ROI: 1.45% Traditional ROI: 2.96%
36 Richmond Hill Road New Canaan, CT Imagine an exquisite Federal-style townhouse born from an extraordinary collaboration betw...	3 beds \| 4 baths \| 3,802 sq.ft.	$2,995,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 0.3% Airbnb Rental Income: $2539 Traditional Rental Income: $5461 Airbnb ROI: -0.98% Traditional ROI: 0.3%
610 Cheese Spring Road New Canaan, CT Welcome to this stunning custom shingle-style residence set amid sweeping lawns, mature fl...	4 beds \| 7 baths \| 5,958 sq.ft.	$3,575,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 1.39% Airbnb Rental Income: $5217 Traditional Rental Income: $10498 Airbnb ROI: -0.52% Traditional ROI: 1.39%
42 Hoyt Street New Canaan, CT Nestled in the heart of downtown New Canaan, this charming and beautifully updated home of...	3 beds \| 3 baths \| 2,842 sq.ft.	$1,695,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 1.06% Airbnb Rental Income: $2539 Traditional Rental Income: $4435 Airbnb ROI: -0.53% Traditional ROI: 1.06%
25 Father Peters Lane New Canaan, CT Enchanting country estate located on a rare private lane. Sophistication Grace and Style a...	5 beds \| 6 baths \| 6,306 sq.ft.	$4,995,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 0.54% Airbnb Rental Income: $5062 Traditional Rental Income: $10787 Airbnb ROI: -0.92% Traditional ROI: 0.54%
60 Heritage Hill Road #A New Canaan, CT Located in one of the community's most desirable settings, this elevated end-unit one-bedr...	1 beds \| 1 baths \| 798 sq.ft.	$409,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 3.48% Airbnb Rental Income: $1082 Traditional Rental Income: $2130 Airbnb ROI: -0.22% Traditional ROI: 3.48%
21 Hickory Drive New Canaan, CT PLEASE PRESENT HIGHEST & BEST OFFERS BY 4:00PM MONDAY JUNE 8TH. Nestled on 1.67 beautiful ...	5 beds \| 4 baths \| 3,112 sq.ft.	$1,695,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 2.56% Airbnb Rental Income: $5062 Traditional Rental Income: $7012 Airbnb ROI: 0.66% Traditional ROI: 2.56%
36 Mortimer Street New Canaan, CT Charming in-town Colonial offering the perfect blend of character, comfort and convenience...	3 beds \| 3 baths \| 2,170 sq.ft.	$1,795,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 0.84% Airbnb Rental Income: $2539 Traditional Rental Income: $4446 Airbnb ROI: -0.67% Traditional ROI: 0.84%
124 Forest Street New Canaan, CT Experience luxury living at its finest with this exquisite brand-new masterpiece built by ...	4 beds \| 5 baths \| 3,553 sq.ft.	$2,950,000	Airbnb cash on cash: -1.65% Traditional cash on cash: -0.23% Airbnb Rental Income: $5217 Traditional Rental Income: $8030 Airbnb ROI: -1.65% Traditional ROI: -0.23%
218 Summer Street New Canaan, CT Nestled in the heart of downtown New Canaan, this charming and beautifully updated colonia...	3 beds \| 2 baths \| 2,256 sq.ft.	$1,325,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 1.09% Airbnb Rental Income: $2539 Traditional Rental Income: $3705 Airbnb ROI: -0.36% Traditional ROI: 1.09%
496 Trinity Pass Road New Canaan, CT This 4 bedroom,3.5 bath tastefully renovated vintage home has an open floor plan,walls and...	4 beds \| 4 baths \| 2,522 sq.ft.	$1,650,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 1.71% Airbnb Rental Income: $5217 Traditional Rental Income: $5528 Airbnb ROI: 0.81% Traditional ROI: 1.71%
126 Forest Street New Canaan, CT Experience luxury living at its finest with this exquisite brand-new masterpiece built by ...	4 beds \| 5 baths \| 3,553 sq.ft.	$2,950,000	Airbnb cash on cash: -1.65% Traditional cash on cash: -0.26% Airbnb Rental Income: $5217 Traditional Rental Income: $7946 Airbnb ROI: -1.65% Traditional ROI: -0.26%
16 Old Stamford Road New Canaan, CT Exceptionally crafted new construction by a highly regarded local builder, this home offer...	5 beds \| 5 baths \| 3,608 sq.ft.	$2,950,000	Airbnb cash on cash: -1.69% Traditional cash on cash: -0.22% Airbnb Rental Income: $5062 Traditional Rental Income: $8059 Airbnb ROI: -1.69% Traditional ROI: -0.22%
20 Richmond Hill Road #2 New Canaan, CT Experience elevated living in the heart of downtown New Canaan with this exquisite boutiqu...	4 beds \| 5 baths \| 2,954 sq.ft.	$2,498,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 0.05% Airbnb Rental Income: $5217 Traditional Rental Income: $7457 Airbnb ROI: -1.38% Traditional ROI: 0.05%
14 Richmond Hill Road #1 New Canaan, CT Experience elevated living in the heart of downtown New Canaan with this exquisite boutiqu...	4 beds \| 5 baths \| 3,351 sq.ft.	$2,695,000	Airbnb cash on cash: -1.51% Traditional cash on cash: 0.06% Airbnb Rental Income: $5217 Traditional Rental Income: $8070 Airbnb ROI: -1.51% Traditional ROI: 0.06%
760 Smith Ridge Road New Canaan, CT Featured in multiple publications and set along New Canaan's coveted Smith Ridge Road, thi...	4 beds \| 4 baths \| 6,556 sq.ft.	$3,595,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 0.01% Airbnb Rental Income: $5217 Traditional Rental Income: $6938 Airbnb ROI: -0.83% Traditional ROI: 0.01%
67 Dunning Road New Canaan, CT A Masterpiece of Colonial Elegance and Resort-Style Living on Dunning Road - Perfectly pos...	5 beds \| 7 baths \| 5,957 sq.ft.	$3,695,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 1.45% Airbnb Rental Income: $5062 Traditional Rental Income: $10707 Airbnb ROI: -0.5% Traditional ROI: 1.45%

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 $1,564,192 and the average price per square foot is $441. In June 2026, the average monthly cash on cash return in New Canaan is 1.00%. The average monthly rental income in New Canaan is $5,671.

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 $5,671.

Your search for investment property begins and ends here

Investment Property for Sale in New Canaan, CT

2 Sleepy Hollow Road

New Canaan, CT

5 beds | 3 baths | 5,658 sq.ft.

$2,195,000

Airbnb cash on cash: 0.1%

Traditional cash on cash: 0.94%

Airbnb Rental Income: $5062

Traditional Rental Income: $5749

Airbnb ROI: 0.1%

Traditional ROI: 0.94%

55 New Norwalk Road

New Canaan, CT

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

$1,200,000

Airbnb cash on cash: 1.61%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $5062

Traditional Rental Income: $4659

Airbnb ROI: 1.61%

Traditional ROI: 2.17%

100 Harrison Avenue

New Canaan, CT

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

$1,795,000

Airbnb cash on cash: 0.59%

Traditional cash on cash: 1.21%

Airbnb Rental Income: $5217

Traditional Rental Income: $5186

Airbnb ROI: 0.59%

Traditional ROI: 1.21%

7 Kimberly Place

New Canaan, CT

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

$3,495,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 1%

Airbnb Rental Income: $5062

Traditional Rental Income: $8590

Airbnb ROI: -0.4%

Traditional ROI: 1%

160 Park Street #102

New Canaan, CT

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

$3,100,000

Airbnb cash on cash: -2.21%

Traditional cash on cash: -0.87%

Airbnb Rental Income: $2539

Traditional Rental Income: $5765

Airbnb ROI: -2.21%

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: -0.31%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $5062

Traditional Rental Income: $12189

Airbnb ROI: -0.31%

Traditional ROI: 3.37%

171 Proprietors Crossing

New Canaan, CT

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

$2,650,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: 1.19%

Airbnb Rental Income: $5062

Traditional Rental Income: $7069

Airbnb ROI: -0.05%

Traditional ROI: 1.19%

25 Gower Street

New Canaan, CT

5 beds | 8 baths | 6,322 sq.ft.

$4,600,000

Airbnb cash on cash: -2.21%

Traditional cash on cash: -0.85%

Airbnb Rental Income: $5062

Traditional Rental Income: $9830

Airbnb ROI: -2.21%