Real Estate Investment Properties for Sale in Darien, CT

Looking for investment property in Darien, CT with high ROI ?

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

Condos for Sale in Darien, CT

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

Showing 1 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2 Settlers Trail #3 Darien, CT Discover the pinnacle of modern luxury in the heart of Darien. Exclusively designed for ad...	3 beds \| 3 baths \| 2,069 sq.ft.	$3,100,000	Airbnb cash on cash: -1.47% Traditional cash on cash: -0.57% Airbnb Rental Income: $2517 Traditional Rental Income: $4482 Airbnb ROI: -1.47% Traditional ROI: -0.57%
Other Investment Properties for Sale in Darien
13 Sunswyck Road Darien , CT Introducing 13 Sunswyck Rd, a distinguished custom residence set within Darien's prestigio...	5 beds \| 6 baths \| 6,151 sq.ft.	$5,250,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 0.47% Airbnb Rental Income: $5317 Traditional Rental Income: $10356 Airbnb ROI: -0.78% Traditional ROI: 0.47%
20 Marianne Road Darien , CT New construction from foundation up and ready for 2026! On a coveted Darien cul-de-sac, th...	5 beds \| 8 baths \| 6,535 sq.ft.	$4,199,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 0.17% Airbnb Rental Income: $5317 Traditional Rental Income: $5786 Airbnb ROI: -0.22% Traditional ROI: 0.17%
561 Middlesex Road Darien , CT Come see this freshly transformed home on a gorgeous, flat 2.64 acre lot in the heart of D...	4 beds \| 4 baths \| 3,411 sq.ft.	$2,999,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 0.63% Airbnb Rental Income: $1829 Traditional Rental Income: $6197 Airbnb ROI: -1.11% Traditional ROI: 0.63%
865 Hollow Tree Ridge Road Darien , CT Set on 7 acres, this exceptional estate offers a private, sophisticated retreat at the end...	5 beds \| 10 baths \| 10,197 sq.ft.	$13,000,000	Airbnb cash on cash: -2.79% Traditional cash on cash: -2.26% Airbnb Rental Income: $5317 Traditional Rental Income: $10583 Airbnb ROI: -2.79% Traditional ROI: -2.26%
15 Queens Lane Darien , CT Rarely do you find a property that has it all: a spacious move-in ready house with a pool,...	5 beds \| 5 baths \| 3,512 sq.ft.	$2,850,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 1.6% Airbnb Rental Income: $5317 Traditional Rental Income: $8841 Airbnb ROI: -0.14% Traditional ROI: 1.6%
7 Waverly Road Darien , CT LIVE THE PERPETUAL VACATION LIFE IN NOROTON BAY - Experience this chic, sun-drenched Beach...	4 beds \| 4 baths \| 3,560 sq.ft.	$3,795,000	Airbnb cash on cash: -1.46% Traditional cash on cash: 0.19% Airbnb Rental Income: $1829 Traditional Rental Income: $7140 Airbnb ROI: -1.46% Traditional ROI: 0.19%
8 Seagate Road Darien , CT Waterviews!! Welcome to 8 Seagate Road, a rare opportunity to live in one of Darien's most...	4 beds \| 3 baths \| 2,796 sq.ft.	$2,700,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 0.41% Airbnb Rental Income: $1829 Traditional Rental Income: $5212 Airbnb ROI: -1.13% Traditional ROI: 0.41%
518 Hoyt Street Darien , CT **Best and final offers provided to seller agent by Wed (6/3/26) at 5pm. Seller will have ...	5 beds \| 4 baths \| 3,680 sq.ft.	$1,999,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 1.67% Airbnb Rental Income: $5317 Traditional Rental Income: $6592 Airbnb ROI: 0.4% Traditional ROI: 1.67%
8 Glenwood Drive Darien , CT Set on a quiet cul-de-sac, this beautifully renovated 5-bedroom, 4-bath Colonial offers a ...	5 beds \| 4 baths \| 3,115 sq.ft.	$1,850,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 2.31% Airbnb Rental Income: $5317 Traditional Rental Income: $7078 Airbnb ROI: 0.66% Traditional ROI: 2.31%
26 Beach Drive Darien , CT Escape to your own private waterfront sanctuary at this hidden gem on Holly Pond, where re...	3 beds \| 2 baths \| 1,930 sq.ft.	$2,995,000	Airbnb cash on cash: -0.97% Traditional cash on cash: -0.22% Airbnb Rental Income: $2517 Traditional Rental Income: $3998 Airbnb ROI: -0.97% Traditional ROI: -0.22%
82 Arrowhead Way Darien , CT (Don't miss the spectacular waterfront video). On the water in the Tokeneke Association, S...	5 beds \| 6 baths \| 5,823 sq.ft.	$8,650,000	Airbnb cash on cash: -1.24% Traditional cash on cash: -0.36% Airbnb Rental Income: $5317 Traditional Rental Income: $11286 Airbnb ROI: -1.24% Traditional ROI: -0.36%

Your search for investment property begins and ends here

Condos for Sale in Darien, CT

2 Settlers Trail #3

Darien, CT

3 beds | 3 baths | 2,069 sq.ft.

$3,100,000

Airbnb cash on cash: -1.47%

Traditional cash on cash: -0.57%

Airbnb Rental Income: $2517

Traditional Rental Income: $4482

Airbnb ROI: -1.47%

Traditional ROI: -0.57%

Other Investment Properties for Sale in Darien

Darien , CT

5 beds | 6 baths | 6,151 sq.ft.

$5,250,000

Airbnb cash on cash: -0.78%

Traditional cash on cash: 0.47%

Airbnb Rental Income: $5317

Traditional Rental Income: $10356

Airbnb ROI: -0.78%

Traditional ROI: 0.47%

Darien , CT

5 beds | 8 baths | 6,535 sq.ft.

$4,199,000

Airbnb cash on cash: -0.22%

Traditional cash on cash: 0.17%

Airbnb Rental Income: $5317

Traditional Rental Income: $5786

Airbnb ROI: -0.22%

Traditional ROI: 0.17%

Darien , CT

4 beds | 4 baths | 3,411 sq.ft.

$2,999,000

Airbnb cash on cash: -1.11%

Traditional cash on cash: 0.63%

Airbnb Rental Income: $1829

Traditional Rental Income: $6197

Airbnb ROI: -1.11%

Traditional ROI: 0.63%

Darien , CT

5 beds | 10 baths | 10,197 sq.ft.

$13,000,000

Airbnb cash on cash: -2.79%

Traditional cash on cash: -2.26%

Airbnb Rental Income: $5317

Traditional Rental Income: $10583

Airbnb ROI: -2.79%

Traditional ROI: -2.26%

Darien , CT

5 beds | 5 baths | 3,512 sq.ft.

$2,850,000

Airbnb cash on cash: -0.14%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $5317

Traditional Rental Income: $8841

Airbnb ROI: -0.14%

Traditional ROI: 1.6%

Darien , CT

4 beds | 4 baths | 3,560 sq.ft.

$3,795,000

Airbnb cash on cash: -1.46%

Traditional cash on cash: 0.19%

Airbnb Rental Income: $1829

Traditional Rental Income: $7140

Airbnb ROI: -1.46%

Traditional ROI: 0.19%

Darien , CT

4 beds | 3 baths | 2,796 sq.ft.

$2,700,000

Airbnb cash on cash: -1.13%

Traditional cash on cash: 0.41%

Airbnb Rental Income: $1829

Traditional Rental Income: $5212

Airbnb ROI: -1.13%

Traditional ROI: 0.41%

Darien , CT

5 beds | 4 baths | 3,680 sq.ft.

$1,999,000

Airbnb cash on cash: 0.4%

Traditional cash on cash: 1.67%