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.

Investment Property for Sale in Darien, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
19 William Street Darien, CT Charming Renovated Home with Separate Income Potential - Minutes to Train & Shopping! Don'...	3 beds \| 2 baths \| 1,300 sq.ft.	$1,325,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 0.86% Airbnb Rental Income: $2242 Traditional Rental Income: $3403 Airbnb ROI: -0.54% Traditional ROI: 0.86%
17 Brushy Hill Road Darien, CT Perched high above the Goodwives River, this stunning Mid-Century Modern home offers sophi...	4 beds \| 5 baths \| 5,051 sq.ft.	$3,300,000	Airbnb cash on cash: -1.15% Traditional cash on cash: 1.51% Airbnb Rental Income: $2511 Traditional Rental Income: $10070 Airbnb ROI: -1.15% Traditional ROI: 1.51%
20 Marianne Road Darien, CT Nearly Complete - A Modern Colonial Haven in Darien. Tucked away on a private, level 1.2 a...	5 beds \| 8 baths \| 6,535 sq.ft.	$4,900,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 0.01% Airbnb Rental Income: $6134 Traditional Rental Income: $5786 Airbnb ROI: -0.18% Traditional ROI: 0.01%
128 West Avenue Darien, CT Move-In Ready Home with open concept living and an ideal location. Welcome to this beautif...	3 beds \| 3 baths \| 1,636 sq.ft.	$1,125,000	Airbnb cash on cash: -1.61% Traditional cash on cash: 0.59% Airbnb Rental Income: $2242 Traditional Rental Income: $3982 Airbnb ROI: -1.61% Traditional ROI: 0.59%
47 Hollow Tree Ridge Road Darien, CT PRICE ADJUSTMENT. Nathaniel B. Weed Gatehouse: A Rare Darien Gem. Discover a rare opportun...	7 beds \| 5 baths \| 3,461 sq.ft.	$1,750,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 2.05% Airbnb Rental Income: $6134 Traditional Rental Income: $8507 Airbnb ROI: -0.16% Traditional ROI: 2.05%
51 Hale Lane #51 Darien, CT Welcome to Middlesex Commons-Darien's most coveted condominium community! This stunning up...	1 beds \| 2 baths \| 900 sq.ft.	$649,900	Airbnb cash on cash: -2.85% Traditional cash on cash: -0.09% Airbnb Rental Income: $1472 Traditional Rental Income: $2709 Airbnb ROI: -2.85% Traditional ROI: -0.09%
41 Wakemore Street Darien, CT Opportunity knocks in Darien, CT! Located on a private road, across from Kensett (Luxury t...	2 beds \| 1 baths \| 724 sq.ft.	$775,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 0.14% Airbnb Rental Income: $2267 Traditional Rental Income: $2449 Airbnb ROI: -0.9% Traditional ROI: 0.14%
23 Maplewood Drive Darien, CT Located at the end of a quiet, tree lined street in the desirable, scenic Stephen Mather n...	5 beds \| 4 baths \| 3,506 sq.ft.	$2,500,000	Airbnb cash on cash: -1.05% Traditional cash on cash: -0.12% Airbnb Rental Income: $6134 Traditional Rental Income: $7073 Airbnb ROI: -1.05% Traditional ROI: -0.12%
261 Hollow Tree Ridge Road Darien, CT This charming 5-bedroom Cape Cod home, originally built in 1941 and extensively renovated,...	5 beds \| 6 baths \| 6,135 sq.ft.	$4,475,000	Airbnb cash on cash: -1.97% Traditional cash on cash: -0.58% Airbnb Rental Income: $6134 Traditional Rental Income: $10667 Airbnb ROI: -1.97% Traditional ROI: -0.58%
109 Stephen Mather Road Darien, CT This classic Colonial has character, charm and generous space. The formal Living Room has ...	5 beds \| 4 baths \| 4,817 sq.ft.	$3,149,500	Airbnb cash on cash: -1.48% Traditional cash on cash: -0.75% Airbnb Rental Income: $6134 Traditional Rental Income: $7048 Airbnb ROI: -1.48% Traditional ROI: -0.75%
11 Old Oak Road Darien, CT Nestled on a quiet cul-de-sac in the Boulder Ridge Association, 11 Old Oak Road is a timel...	5 beds \| 6 baths \| 8,938 sq.ft.	$3,895,000	Airbnb cash on cash: -1.81% Traditional cash on cash: -0.28% Airbnb Rental Income: $6134 Traditional Rental Income: $10438 Airbnb ROI: -1.81% Traditional ROI: -0.28%
19 Littlebrook Road Darien, CT Move right into this spacious home that just completed a remodel and is waiting for a new ...	4 beds \| 3 baths \| 2,156 sq.ft.	$1,499,000	Airbnb cash on cash: -1.83% Traditional cash on cash: 0.25% Airbnb Rental Income: $2511 Traditional Rental Income: $4805 Airbnb ROI: -1.83% Traditional ROI: 0.25%
561 Middlesex Road Darien, CT In the heart of Darien, where history lingers and owls whisper through the trees, stands a...	4 beds \| 4 baths \| 3,411 sq.ft.	$2,999,000	Airbnb cash on cash: -2.48% Traditional cash on cash: -0.94% Airbnb Rental Income: $2511 Traditional Rental Income: $6197 Airbnb ROI: -2.48% Traditional ROI: -0.94%

Real Estate investment in Darien, CT

There are 14 properties for sale in the city of Darien . The median list price in Darien is $2,425,000 and the average price per square foot is $647. In December 2025, the average monthly cash on cash return in Darien is N/A%. The average monthly rental income in Darien is $6,197.

Darien, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 14 investment properties available for sale in Darien.

In 2025, the best neighborhood to buy investment property is Darien.

The ROI for Long-Term is higher than the Short-Term in Darien with average rental income of $6,197.

Your search for investment property begins and ends here

Investment Property for Sale in Darien, CT

19 William Street

Darien, CT

3 beds | 2 baths | 1,300 sq.ft.

$1,325,000

Airbnb cash on cash: -0.54%

Traditional cash on cash: 0.86%

Airbnb Rental Income: $2242

Traditional Rental Income: $3403

Airbnb ROI: -0.54%

Traditional ROI: 0.86%

17 Brushy Hill Road

Darien, CT

4 beds | 5 baths | 5,051 sq.ft.

$3,300,000

Airbnb cash on cash: -1.15%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $2511

Traditional Rental Income: $10070

Airbnb ROI: -1.15%

Traditional ROI: 1.51%

20 Marianne Road

Darien, CT

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

$4,900,000

Airbnb cash on cash: -0.18%

Traditional cash on cash: 0.01%

Airbnb Rental Income: $6134

Traditional Rental Income: $5786

Airbnb ROI: -0.18%

Traditional ROI: 0.01%

128 West Avenue

Darien, CT

3 beds | 3 baths | 1,636 sq.ft.

$1,125,000

Airbnb cash on cash: -1.61%

Traditional cash on cash: 0.59%

Airbnb Rental Income: $2242

Traditional Rental Income: $3982

Airbnb ROI: -1.61%

Traditional ROI: 0.59%

47 Hollow Tree Ridge Road

Darien, CT

7 beds | 5 baths | 3,461 sq.ft.

$1,750,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: 2.05%

Airbnb Rental Income: $6134

Traditional Rental Income: $8507

Airbnb ROI: -0.16%

Traditional ROI: 2.05%

51 Hale Lane #51

Darien, CT

1 beds | 2 baths | 900 sq.ft.

$649,900

Airbnb cash on cash: -2.85%

Traditional cash on cash: -0.09%

Airbnb Rental Income: $1472

Traditional Rental Income: $2709

Airbnb ROI: -2.85%

Traditional ROI: -0.09%

41 Wakemore Street

Darien, CT

2 beds | 1 baths | 724 sq.ft.

$775,000

Airbnb cash on cash: -0.9%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $2267

Traditional Rental Income: $2449

Airbnb ROI: -0.9%

Traditional ROI: 0.14%

23 Maplewood Drive

Darien, CT

5 beds | 4 baths | 3,506 sq.ft.

$2,500,000

Airbnb cash on cash: -1.05%

Traditional cash on cash: -0.12%

Airbnb Rental Income: $6134

Traditional Rental Income: $7073

Airbnb ROI: -1.05%