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
489 Hoyt Street Darien, CT Watch video link below! Charming New England Farmhouse with golf course views. Perfect...	4 beds \| 3 baths \| 3,630 sq.ft.	$1,649,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 1.92% Airbnb Rental Income: $1917 Traditional Rental Income: $5503 Airbnb ROI: -0.75% Traditional ROI: 1.92%
694 Boston Post Road Darien, CT LOCATION! LOCATION! LOCATION! Renovated, Bright, Hardwood floors, Central AC, Mint conditi...	4 beds \| 2 baths \| 2,352 sq.ft.	$1,499,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 1.06% Airbnb Rental Income: $1917 Traditional Rental Income: $3944 Airbnb ROI: -0.76% Traditional ROI: 1.06%
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: -1.32% Traditional cash on cash: 1.51% Airbnb Rental Income: $1917 Traditional Rental Income: $10070 Airbnb ROI: -1.32% Traditional ROI: 1.51%
20 Marianne Road Darien, CT Dreaming of customizing your new home? Nestled on a private and flat 1.2 acres on a desira...	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: $6160 Traditional Rental Income: $5786 Airbnb ROI: -0.18% Traditional ROI: 0.01%
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: -0.15% Traditional cash on cash: 2.05% Airbnb Rental Income: $6160 Traditional Rental Income: $8507 Airbnb ROI: -0.15% Traditional ROI: 2.05%
14 Maple Street Darien, CT Well maintained colonial in prime location walking distance to Noroton Heights train stati...	4 beds \| 3 baths \| 2,659 sq.ft.	$1,395,000	Airbnb cash on cash: -2.12% Traditional cash on cash: 0.72% Airbnb Rental Income: $1917 Traditional Rental Income: $5083 Airbnb ROI: -2.12% Traditional ROI: 0.72%
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: -2.43% Traditional cash on cash: -0.09% Airbnb Rental Income: $1778 Traditional Rental Income: $2709 Airbnb ROI: -2.43% Traditional ROI: -0.09%
76 Deepwood Road Darien, CT Set on a full acre in one of Darien's most sought-after neighborhoods, this property prese...	5 beds \| 4 baths \| 3,897 sq.ft.	$2,350,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 0.14% Airbnb Rental Income: $6160 Traditional Rental Income: $7231 Airbnb ROI: -0.91% Traditional ROI: 0.14%
101 Long Neck Point Road Darien, CT Perched high on the bluff of Long Neck Point, this 6680sf custom-built brick estate offers...	5 beds \| 7 baths \| 6,689 sq.ft.	$9,250,000	Airbnb cash on cash: -2.57% Traditional cash on cash: -1.84% Airbnb Rental Income: $6160 Traditional Rental Income: $11200 Airbnb ROI: -2.57% Traditional ROI: -1.84%
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: -1.3% Traditional cash on cash: 0.14% Airbnb Rental Income: $1921 Traditional Rental Income: $2449 Airbnb ROI: -1.3% Traditional ROI: 0.14%
17 Lynn Court Darien, CT This is the one you've been waiting for! Spacious 4 BR, 3 BA home in coveted, friendly nei...	4 beds \| 3 baths \| 2,552 sq.ft.	$1,410,000	Airbnb cash on cash: -2.13% Traditional cash on cash: 0.82% Airbnb Rental Income: $1917 Traditional Rental Income: $5273 Airbnb ROI: -2.13% Traditional ROI: 0.82%
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: -1.04% Traditional cash on cash: -0.12% Airbnb Rental Income: $6160 Traditional Rental Income: $7073 Airbnb ROI: -1.04% 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: -1.96% Traditional cash on cash: -0.58% Airbnb Rental Income: $6160 Traditional Rental Income: $10667 Airbnb ROI: -1.96% 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: -1.47% Traditional cash on cash: -0.75% Airbnb Rental Income: $6160 Traditional Rental Income: $7048 Airbnb ROI: -1.47% Traditional ROI: -0.75%
49 Echo Drive North Darien, CT Welcome to this classic center hall Colonial, perfectly situated on one of the most sought...	3 beds \| 3 baths \| 2,023 sq.ft.	$1,595,000	Airbnb cash on cash: -2.11% Traditional cash on cash: -0.2% Airbnb Rental Income: $2156 Traditional Rental Income: $4440 Airbnb ROI: -2.11% Traditional ROI: -0.2%
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: -1.8% Traditional cash on cash: -0.28% Airbnb Rental Income: $6160 Traditional Rental Income: $10438 Airbnb ROI: -1.8% Traditional ROI: -0.28%
26 Birch Road Darien, CT Wonderful opportunity in one of Darien's most sought after neighborhoods; 4,000+ sqft of c...	4 beds \| 4 baths \| 4,155 sq.ft.	$2,700,000	Airbnb cash on cash: -2.61% Traditional cash on cash: -0.47% Airbnb Rental Income: $1917 Traditional Rental Income: $6770 Airbnb ROI: -2.61% Traditional ROI: -0.47%
20 Denhurst Place Darien, CT Welcome to 20 Denhurst Place - a lovingly maintained Colonial proudly owned by the same fa...	4 beds \| 3 baths \| 2,120 sq.ft.	$1,300,000	Airbnb cash on cash: -2.06% Traditional cash on cash: 0.42% Airbnb Rental Income: $1917 Traditional Rental Income: $4406 Airbnb ROI: -2.06% Traditional ROI: 0.42%

Real Estate investment in Darien, CT

There are 18 properties for sale in the city of Darien . The median list price in Darien is $2,050,000 and the average price per square foot is $526. In October 2025, the average monthly cash on cash return in Darien is N/A%. The average monthly rental income in Darien is $5,786.

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

There are 18 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 $5,786.

Your search for investment property begins and ends here

Investment Property for Sale in Darien, CT

489 Hoyt Street

Darien, CT

4 beds | 3 baths | 3,630 sq.ft.

$1,649,000

Airbnb cash on cash: -0.75%

Traditional cash on cash: 1.92%

Airbnb Rental Income: $1917

Traditional Rental Income: $5503

Airbnb ROI: -0.75%

Traditional ROI: 1.92%

694 Boston Post Road

Darien, CT

4 beds | 2 baths | 2,352 sq.ft.

$1,499,000

Airbnb cash on cash: -0.76%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $1917

Traditional Rental Income: $3944

Airbnb ROI: -0.76%

Traditional ROI: 1.06%

17 Brushy Hill Road

Darien, CT

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

$3,300,000

Airbnb cash on cash: -1.32%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $1917

Traditional Rental Income: $10070

Airbnb ROI: -1.32%

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: $6160

Traditional Rental Income: $5786

Airbnb ROI: -0.18%

Traditional ROI: 0.01%

47 Hollow Tree Ridge Road

Darien, CT

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

$1,750,000

Airbnb cash on cash: -0.15%

Traditional cash on cash: 2.05%

Airbnb Rental Income: $6160

Traditional Rental Income: $8507

Airbnb ROI: -0.15%

Traditional ROI: 2.05%

14 Maple Street

Darien, CT

4 beds | 3 baths | 2,659 sq.ft.

$1,395,000

Airbnb cash on cash: -2.12%

Traditional cash on cash: 0.72%

Airbnb Rental Income: $1917

Traditional Rental Income: $5083

Airbnb ROI: -2.12%

Traditional ROI: 0.72%

51 Hale Lane #51

Darien, CT

1 beds | 2 baths | 900 sq.ft.

$649,900

Airbnb cash on cash: -2.43%

Traditional cash on cash: -0.09%

Airbnb Rental Income: $1778

Traditional Rental Income: $2709

Airbnb ROI: -2.43%

Traditional ROI: -0.09%

76 Deepwood Road

Darien, CT

5 beds | 4 baths | 3,897 sq.ft.

$2,350,000

Airbnb cash on cash: -0.91%

Traditional cash on cash: 0.14%

Airbnb Rental Income: $6160

Traditional Rental Income: $7231

Airbnb ROI: -0.91%