Real Estate Investment Properties for Sale in Old Saybrook, CT

Looking for investment property in Old Saybrook, CT with high ROI ?

Explore a variety of short-term homes & houses in Old Saybrook, CT. Invest wisely with VRBO & Old Saybrook, 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 Old Saybrook, CT

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
25 Sheffield Street #7 Old Saybrook, CT Step into refined, effortless living in this beautifully appointed luxury condo featuring ...	2 beds \| 4 baths \| 2,151 sq.ft.	$940,000	Airbnb cash on cash: -1.46% Traditional cash on cash: 2.09% Airbnb Rental Income: $1330 Traditional Rental Income: $4021 Airbnb ROI: -1.46% Traditional ROI: 2.09%
61 Ingham Hill Road Old Saybrook, CT Step into the charm of this delightful 1920 year-round bungalow, just a stone's throw from...	1 beds \| 2 baths \| 1,205 sq.ft.	$449,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 3.12% Airbnb Rental Income: $988 Traditional Rental Income: $2132 Airbnb ROI: -0.45% Traditional ROI: 3.12%
129 Nehantic Trail Old Saybrook, CT MOVE-IN READY! Remodeled story book Cape Cod in the desirable Indian Town beach community ...	2 beds \| 2 baths \| 944 sq.ft.	$799,900	Airbnb cash on cash: -0.81% Traditional cash on cash: 0.83% Airbnb Rental Income: $1330 Traditional Rental Income: $2147 Airbnb ROI: -0.81% Traditional ROI: 0.83%
175 N Cove Road Old Saybrook, CT An exceptional offering in the heart of North Cove, this storied estate presents a rare co...	4 beds \| 5 baths \| 3,518 sq.ft.	$3,695,000	Airbnb cash on cash: -1.43% Traditional cash on cash: -0.13% Airbnb Rental Income: $2389 Traditional Rental Income: $6265 Airbnb ROI: -1.43% Traditional ROI: -0.13%
2 Old South Cove Road Old Saybrook, CT At Saybrook Point, life is defined by the water. Morning walks by the marina, kayaking on ...	3 beds \| 4 baths \| 2,472 sq.ft.	$1,589,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 1.35% Airbnb Rental Income: $2398 Traditional Rental Income: $5024 Airbnb ROI: -0.83% Traditional ROI: 1.35%
24 W Shore Drive Old Saybrook, CT Welcome to 24 W. Shore Dr., Old Saybrook, ideally located in one of Connecticut's most ren...	3 beds \| 1 baths \| 884 sq.ft.	$1,325,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 0.6% Airbnb Rental Income: $2398 Traditional Rental Income: $2640 Airbnb ROI: -0.07% Traditional ROI: 0.6%
446 Main Street #9 Old Saybrook, CT Nestled along the serene shores of North Cove, this exceptional 2,300+ square foot detache...	2 beds \| 3 baths \| 2,294 sq.ft.	$1,300,000	Airbnb cash on cash: -1.78% Traditional cash on cash: 1.31% Airbnb Rental Income: $1330 Traditional Rental Income: $4648 Airbnb ROI: -1.78% Traditional ROI: 1.31%
25 Sunset Road #7 Old Saybrook, CT Your chance to own in highly desirable Oyster River Landing-just steps from a private mari...	2 beds \| 3 baths \| 2,090 sq.ft.	$799,900	Airbnb cash on cash: -1.51% Traditional cash on cash: 2.4% Airbnb Rental Income: $1330 Traditional Rental Income: $3839 Airbnb ROI: -1.51% Traditional ROI: 2.4%
367 Main Street unit: 7 Old Saybrook, CT WOW! A free-standing condo in the highly sought-after Banbury Crossing community. This stu...	2 beds \| 2 baths \| 1,235 sq.ft.	$599,900	Airbnb cash on cash: -1.35% Traditional cash on cash: 2.38% Airbnb Rental Income: $1330 Traditional Rental Income: $3009 Airbnb ROI: -1.35% Traditional ROI: 2.38%
10 Edwards Road Old Saybrook, CT Charming 2 bedroom ranch set on a .20 acre lot in desirable Old Saybrook Cornfield Point B...	2 beds \| 1 baths \| 1,198 sq.ft.	$699,900	Airbnb cash on cash: -0.32% Traditional cash on cash: 2.11% Airbnb Rental Income: $1330 Traditional Rental Income: $2510 Airbnb ROI: -0.32% Traditional ROI: 2.11%
17 College Street Old Saybrook, CT Discover the perfect blend of comfort, style, and convenience in this beautifully remodele...	3 beds \| 3 baths \| 1,960 sq.ft.	$1,140,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 2.02% Airbnb Rental Income: $2398 Traditional Rental Income: $3910 Airbnb ROI: 0.04% Traditional ROI: 2.02%
18 Old South Cove Road Old Saybrook, CT Situated in Old Saybrook's most protected and prominent corridor, 18 Old South Cove Road p...	4 beds \| 3 baths \| 1,569 sq.ft.	$975,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 2.6% Airbnb Rental Income: $2389 Traditional Rental Income: $3791 Airbnb ROI: 0.41% Traditional ROI: 2.6%
185 Ingham Hill Road Old Saybrook, CT Set on a generous, professionally landscaped lot in one of Old Saybrook's most desirable l...	4 beds \| 3 baths \| 2,896 sq.ft.	$799,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 4.32% Airbnb Rental Income: $2389 Traditional Rental Income: $4552 Airbnb ROI: 0.63% Traditional ROI: 4.32%
3 Birch Street Old Saybrook, CT Seller is calling for Hightest and Best by Monday at 5:00pm Enjoy the ease of one-floor...	3 beds \| 2 baths \| 1,600 sq.ft.	$739,900	Airbnb cash on cash: 0.58% Traditional cash on cash: 2.38% Airbnb Rental Income: $2398 Traditional Rental Income: $3046 Airbnb ROI: 0.58% Traditional ROI: 2.38%
23 Meadowood Lane Old Saybrook, CT A lovely renovated ranch in the heart of "Meadowood", a desirable family friendly communit...	3 beds \| 2 baths \| 1,818 sq.ft.	$669,900	Airbnb cash on cash: 0.98% Traditional cash on cash: 3.92% Airbnb Rental Income: $2398 Traditional Rental Income: $3647 Airbnb ROI: 0.98% Traditional ROI: 3.92%
4 Sheffield Cove Road Old Saybrook, CT Coastal Living with Water Views Set on a private cul-de-sac overlooking South Cove, this 2...	3 beds \| 3 baths \| 2,821 sq.ft.	$1,595,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 1.36% Airbnb Rental Income: $2398 Traditional Rental Income: $4574 Airbnb ROI: -0.51% Traditional ROI: 1.36%
100 Dudley Avenue #H42 Old Saybrook, CT Coastal elegance meets low-maintenance living in this beautifully appointed townhouse-styl...	2 beds \| 3 baths \| 1,565 sq.ft.	$650,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 2.43% Airbnb Rental Income: $1330 Traditional Rental Income: $2613 Airbnb ROI: -0.37% Traditional ROI: 2.43%
3 Deerfield Road Old Saybrook, CT Exceptional Colonial! This stunning 1916 sq.ft. home is in the desirable Meadowood area, o...	4 beds \| 3 baths \| 1,916 sq.ft.	$699,900	Airbnb cash on cash: 0.82% Traditional cash on cash: 4.79% Airbnb Rental Income: $2389 Traditional Rental Income: $4391 Airbnb ROI: 0.82% Traditional ROI: 4.79%
71 Maple Avenue Old Saybrook, CT If you've been searching for the perfect location and effortless one level living in the i...	2 beds \| 2 baths \| 2,069 sq.ft.	$650,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 3.57% Airbnb Rental Income: $1330 Traditional Rental Income: $3391 Airbnb ROI: -0.5% Traditional ROI: 3.57%
21 Fenbrook Road Old Saybrook, CT Welcome to an exceptional year-round home located in one of Connecticut's most renowned be...	3 beds \| 3 baths \| 1,916 sq.ft.	$1,590,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 1.22% Airbnb Rental Income: $2398 Traditional Rental Income: $4017 Airbnb ROI: -0.27% Traditional ROI: 1.22%
14 Cedarwood Lane Old Saybrook, CT Welcome to your new shoreline home - a charming ranch-style retreat nestled in the heart o...	3 beds \| 2 baths \| 1,033 sq.ft.	$675,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 3.29% Airbnb Rental Income: $2398 Traditional Rental Income: $3186 Airbnb ROI: 1.1% Traditional ROI: 3.29%

Real Estate investment in Old-saybrook, CT

There are 24 properties for sale in the city of Old Saybrook . The median list price in Old Saybrook is $799,900 and the average price per square foot is $431. In May 2026, the average monthly cash on cash return in Old Saybrook is 2.00%. The average monthly rental income in Old Saybrook is $3,647.

Old-saybrook, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 24 investment properties available for sale in Old-saybrook.

In 2026, the best neighborhood to buy investment property is Old Saybrook.

The ROI for Short-Term is higher than the Long-Term in Old-saybrook with average rental income of $2,389.

Your search for investment property begins and ends here

Investment Property for Sale in Old Saybrook, CT

25 Sheffield Street #7

Old Saybrook, CT

2 beds | 4 baths | 2,151 sq.ft.

$940,000

Airbnb cash on cash: -1.46%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $1330

Traditional Rental Income: $4021

Airbnb ROI: -1.46%

Traditional ROI: 2.09%

61 Ingham Hill Road

Old Saybrook, CT

1 beds | 2 baths | 1,205 sq.ft.

$449,000

Airbnb cash on cash: -0.45%

Traditional cash on cash: 3.12%

Airbnb Rental Income: $988

Traditional Rental Income: $2132

Airbnb ROI: -0.45%

Traditional ROI: 3.12%

129 Nehantic Trail

Old Saybrook, CT

2 beds | 2 baths | 944 sq.ft.

$799,900

Airbnb cash on cash: -0.81%

Traditional cash on cash: 0.83%

Airbnb Rental Income: $1330

Traditional Rental Income: $2147

Airbnb ROI: -0.81%

Traditional ROI: 0.83%

175 N Cove Road

Old Saybrook, CT

4 beds | 5 baths | 3,518 sq.ft.

$3,695,000

Airbnb cash on cash: -1.43%

Traditional cash on cash: -0.13%

Airbnb Rental Income: $2389

Traditional Rental Income: $6265

Airbnb ROI: -1.43%

Traditional ROI: -0.13%

2 Old South Cove Road

Old Saybrook, CT

3 beds | 4 baths | 2,472 sq.ft.

$1,589,000

Airbnb cash on cash: -0.83%

Traditional cash on cash: 1.35%

Airbnb Rental Income: $2398

Traditional Rental Income: $5024

Airbnb ROI: -0.83%

Traditional ROI: 1.35%

24 W Shore Drive

Old Saybrook, CT

3 beds | 1 baths | 884 sq.ft.

$1,325,000

Airbnb cash on cash: -0.07%

Traditional cash on cash: 0.6%

Airbnb Rental Income: $2398

Traditional Rental Income: $2640

Airbnb ROI: -0.07%

Traditional ROI: 0.6%

446 Main Street #9

Old Saybrook, CT

2 beds | 3 baths | 2,294 sq.ft.

$1,300,000

Airbnb cash on cash: -1.78%

Traditional cash on cash: 1.31%

Airbnb Rental Income: $1330

Traditional Rental Income: $4648

Airbnb ROI: -1.78%

Traditional ROI: 1.31%

25 Sunset Road #7

Old Saybrook, CT

2 beds | 3 baths | 2,090 sq.ft.

$799,900

Airbnb cash on cash: -1.51%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $1330

Traditional Rental Income: $3839

Airbnb ROI: -1.51%