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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
372 Maple Avenue Old Saybrook, CT Most beach homes ask you to choose: location or amenities, space or style, primary home or...	3 beds \| 3 baths \| 3,389 sq.ft.	$2,550,000	Airbnb cash on cash: -1.16% Traditional cash on cash: -0.51% Airbnb Rental Income: $2832 Traditional Rental Income: $3713 Airbnb ROI: -1.16% Traditional ROI: -0.51%
23 Clinton Avenue Old Saybrook, CT Welcome to 23 Clinton Avenue, Old Saybrook - a stunning, fully renovated 3-bedroom, 2-bath...	3 beds \| 2 baths \| 1,510 sq.ft.	$924,900	Airbnb cash on cash: 0.98% Traditional cash on cash: 2.48% Airbnb Rental Income: $2832 Traditional Rental Income: $3461 Airbnb ROI: 0.98% Traditional ROI: 2.48%
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: 0.22% Traditional cash on cash: 0.6% Airbnb Rental Income: $2832 Traditional Rental Income: $2640 Airbnb ROI: 0.22% Traditional ROI: 0.6%
1780 Boston Post Road Old Saybrook, CT Commercial Mixed Use, cross-posted on MLS alternative # 24149460. 7.06 CAP r a t e ~ Prime...	4 beds \| 3 baths \| 2,236 sq.ft.	$850,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 4.28% Airbnb Rental Income: $3536 Traditional Rental Income: $4818 Airbnb ROI: 1.68% Traditional ROI: 4.28%
24 Church Street Old Saybrook, CT RARELY AVAILABLE NEW CONSTRUCTION IN NORTH COVE! This modern farmhouse-style Cape, built i...	3 beds \| 3 baths \| 2,560 sq.ft.	$1,450,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 1.5% Airbnb Rental Income: $2832 Traditional Rental Income: $4264 Airbnb ROI: -0.06% Traditional ROI: 1.5%
6 Parkman Place Old Saybrook, CT Nestled on a quiet cul-de-sac in the heart of the Connecticut River Shoreline, this stunni...	4 beds \| 3 baths \| 3,301 sq.ft.	$1,350,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 1.83% Airbnb Rental Income: $3536 Traditional Rental Income: $4436 Airbnb ROI: 0.49% Traditional ROI: 1.83%
25 Sunset Road unit: 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.	$825,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 1.45% Airbnb Rental Income: $1946 Traditional Rental Income: $3182 Airbnb ROI: -0.83% Traditional ROI: 1.45%
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: -0.43% Traditional cash on cash: 2.69% Airbnb Rental Income: $1946 Traditional Rental Income: $3182 Airbnb ROI: -0.43% Traditional ROI: 2.69%
21 Harvey Old Saybrook, CT It's time to own your beach home in the heart of Old Saybrook! This well-maintained mobile...	2 beds \| 1 baths \| 792 sq.ft.	$185,000	Airbnb cash on cash: 4.19% Traditional cash on cash: 9.39% Airbnb Rental Income: $1946 Traditional Rental Income: $2347 Airbnb ROI: 4.19% Traditional ROI: 9.39%
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: 0.46% Traditional cash on cash: 2.11% Airbnb Rental Income: $1946 Traditional Rental Income: $2510 Airbnb ROI: 0.46% 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.	$1,199,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 1.35% Airbnb Rental Income: $2832 Traditional Rental Income: $3325 Airbnb ROI: 0.31% Traditional ROI: 1.35%
41 Farview Avenue Old Saybrook, CT Coming Soon! You have been waiting for this location near Kavanagh (Trask) Park!! Charming...	4 beds \| 2 baths \| 1,400 sq.ft.	$659,900	Airbnb cash on cash: 2.54% Traditional cash on cash: 3.82% Airbnb Rental Income: $3536 Traditional Rental Income: $3546 Airbnb ROI: 2.54% Traditional ROI: 3.82%

Real Estate investment in Old-saybrook, CT

There are 14 properties for sale in the city of Old Saybrook . The median list price in Old Saybrook is $887,450 and the average price per square foot is $445. In March 2026, the average monthly cash on cash return in Old Saybrook is 2.00%. The average monthly rental income in Old Saybrook is $3,393.

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

There are 14 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 $2,832.

Your search for investment property begins and ends here

Investment Property for Sale in Old Saybrook, CT

372 Maple Avenue

Old Saybrook, CT

3 beds | 3 baths | 3,389 sq.ft.

$2,550,000

Airbnb cash on cash: -1.16%

Traditional cash on cash: -0.51%

Airbnb Rental Income: $2832

Traditional Rental Income: $3713

Airbnb ROI: -1.16%

Traditional ROI: -0.51%

23 Clinton Avenue

Old Saybrook, CT

3 beds | 2 baths | 1,510 sq.ft.

$924,900

Airbnb cash on cash: 0.98%

Traditional cash on cash: 2.48%

Airbnb Rental Income: $2832

Traditional Rental Income: $3461

Airbnb ROI: 0.98%

Traditional ROI: 2.48%

24 W Shore Drive

Old Saybrook, CT

3 beds | 1 baths | 884 sq.ft.

$1,325,000

Airbnb cash on cash: 0.22%

Traditional cash on cash: 0.6%

Airbnb Rental Income: $2832

Traditional Rental Income: $2640

Airbnb ROI: 0.22%

Traditional ROI: 0.6%

1780 Boston Post Road

Old Saybrook, CT

4 beds | 3 baths | 2,236 sq.ft.

$850,000

Airbnb cash on cash: 1.68%

Traditional cash on cash: 4.28%

Airbnb Rental Income: $3536

Traditional Rental Income: $4818

Airbnb ROI: 1.68%

Traditional ROI: 4.28%

24 Church Street

Old Saybrook, CT

3 beds | 3 baths | 2,560 sq.ft.

$1,450,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 1.5%

Airbnb Rental Income: $2832

Traditional Rental Income: $4264

Airbnb ROI: -0.06%

Traditional ROI: 1.5%

6 Parkman Place

Old Saybrook, CT

4 beds | 3 baths | 3,301 sq.ft.

$1,350,000

Airbnb cash on cash: 0.49%

Traditional cash on cash: 1.83%

Airbnb Rental Income: $3536

Traditional Rental Income: $4436

Airbnb ROI: 0.49%

Traditional ROI: 1.83%

25 Sunset Road unit: 7

Old Saybrook, CT

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

$825,000

Airbnb cash on cash: -0.83%

Traditional cash on cash: 1.45%

Airbnb Rental Income: $1946

Traditional Rental Income: $3182

Airbnb ROI: -0.83%

Traditional ROI: 1.45%

367 Main Street unit: 7

Old Saybrook, CT

2 beds | 2 baths | 1,235 sq.ft.

$599,900

Airbnb cash on cash: -0.43%

Traditional cash on cash: 2.69%

Airbnb Rental Income: $1946

Traditional Rental Income: $3182

Airbnb ROI: -0.43%