Real Estate Investment Properties for Sale in Chaplin, CT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
21 Linkkila Lane Chaplin, CT Private Country Retreat with In-Law Suite on Nearly 4 Acres. Welcome to 21 Linkkila Lane i...	5 beds \| 4 baths \| 2,760 sq.ft.	$599,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.84% Airbnb Rental Income: $null Traditional Rental Income: $4049 Airbnb ROI: N/A Traditional ROI: 4.84%
287 S Bear Hill Rd Chaplin, CT Set on 3.39 picturesque acres, this beautifully renovated property offers the perfect blen...	4 beds \| 2 baths \| 2,900 sq.ft.	$789,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.02% Airbnb Rental Income: $null Traditional Rental Income: $4788 Airbnb ROI: N/A Traditional ROI: 4.02%
13 Bates Rd Chaplin, CT Spacious farmhouse living at its best! This charming 5-bedroom, 2 full bath, and 1 half ba...	5 beds \| 2 baths \| 2,887 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.88% Airbnb Rental Income: $null Traditional Rental Income: $4174 Airbnb ROI: N/A Traditional ROI: 6.88%
Investment Properties for Sale in Other Cities of Connecticut
95 Audubon Street #339 New Haven , CT Rare find: a single level, 2 bedroom, 2 bathroom ~1400 sq.ft. unit located at a desirable ...	2 beds \| 2 baths \| 1,395 sq.ft.	$620,000	Airbnb cash on cash: -2.48% Traditional cash on cash: 0.13% Airbnb Rental Income: $1571 Traditional Rental Income: $2627 Airbnb ROI: -2.48% Traditional ROI: 0.13%
32 Nearwater Rd Norwalk , CT Located within the well-desired Pine Point Association, this splendidly renovated home off...	3 beds \| 2 baths \| 2,442 sq.ft.	$3,000,000	Airbnb cash on cash: -0.88% Traditional cash on cash: -0.72% Airbnb Rental Income: $3703 Traditional Rental Income: $3330 Airbnb ROI: -0.88% Traditional ROI: -0.72%
2 Elmwood Dr #2 Fairfield , CT Rare opportunity in sought-after Southport Green-just steps to Southport Village and Metro...	3 beds \| 3 baths \| 3,328 sq.ft.	$2,200,000	Airbnb cash on cash: -1.85% Traditional cash on cash: 0.19% Airbnb Rental Income: $2413 Traditional Rental Income: $5995 Airbnb ROI: -1.85% Traditional ROI: 0.19%
347 New London Tpke Stonington , CT Coming Soon! Rare opportunity to own a one-of-a-kind circa 1700 Antique Cape set on more t...	3 beds \| 3 baths \| 2,632 sq.ft.	$719,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 3.8% Airbnb Rental Income: $3011 Traditional Rental Income: $3713 Airbnb ROI: 1.72% Traditional ROI: 3.8%
461 Bank St #702 New London , CT This Waterview Unit Has Both Water Views And Panoramic City Views! Outdoor Balcony, Granit...	2 beds \| 1 baths \| 1,270 sq.ft.	$329,900	Airbnb cash on cash: -2.74% Traditional cash on cash: 0.91% Airbnb Rental Income: $1104 Traditional Rental Income: $1864 Airbnb ROI: -2.74% Traditional ROI: 0.91%
104 Parkway S New London , CT Looking for luxury, comfort, privacy, and CT's best private beaches? It is just a 5-minute...	5 beds \| 5 baths \| 3,696 sq.ft.	$720,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 9.92% Airbnb Rental Income: $3169 Traditional Rental Income: $8500 Airbnb ROI: 0.91% Traditional ROI: 9.92%
1150 Whitney Avenue #5 Hamden , CT PRICE REDUCED! Beautifully remodeled townhouse-style 1-bedroom condo offering the perfect ...	1 beds \| 1 baths \| 636 sq.ft.	$159,500	Airbnb cash on cash: -2.98% Traditional cash on cash: 4.94% Airbnb Rental Income: $652 Traditional Rental Income: $1561 Airbnb ROI: -2.98% Traditional ROI: 4.94%
52 Merrimac St Danbury , CT Location, location, location! Commuting super spot! Shopping and restaurants all moments...	2 beds \| 1 baths \| 1,075 sq.ft.	$399,999	Airbnb cash on cash: 1.38% Traditional cash on cash: 1.96% Airbnb Rental Income: $1741 Traditional Rental Income: $1479 Airbnb ROI: 1.38% Traditional ROI: 1.96%
100 Austin St New Britain , CT Perfect project here. This Colonial is in need of some love. With hardwood flooring, origi...	3 beds \| 1 baths \| 1,314 sq.ft.	$299,900	Airbnb cash on cash: -0.69% Traditional cash on cash: 3.68% Airbnb Rental Income: $889 Traditional Rental Income: $1785 Airbnb ROI: -0.69% Traditional ROI: 3.68%
215 Beach St #1B West Haven , CT Ideal location for anyone who wants to live overlooking the beach and Long Island Sound! T...	2 beds \| 1 baths \| 850 sq.ft.	$349,999	Airbnb cash on cash: -1.28% Traditional cash on cash: 2.14% Airbnb Rental Income: $1121 Traditional Rental Income: $1868 Airbnb ROI: -1.28% Traditional ROI: 2.14%
59 North Pl West Haven , CT Colonial home in a need of work located near shopping center and major routes of the city....	4 beds \| 2 baths \| 1,129 sq.ft.	$389,900	Airbnb cash on cash: 2.47% Traditional cash on cash: 5.05% Airbnb Rental Income: $2295 Traditional Rental Income: $2665 Airbnb ROI: 2.47% Traditional ROI: 5.05%
58 Briar Woods Trail Stamford , CT Tucked into a serene, nature-filled setting, this beautifully updated contemporary ranch o...	3 beds \| 5 baths \| 4,388 sq.ft.	$1,099,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 4.99% Airbnb Rental Income: $3107 Traditional Rental Income: $7773 Airbnb ROI: -0.26% Traditional ROI: 4.99%
174 Loper St Southington , CT If you're looking for a generously sized 3 bedroom home in Southington this is it! The 190...	3 beds \| 2 baths \| 1,908 sq.ft.	$439,900	Airbnb cash on cash: 0.38% Traditional cash on cash: 5.08% Airbnb Rental Income: $1634 Traditional Rental Income: $3108 Airbnb ROI: 0.38% Traditional ROI: 5.08%
29 Poverty Hollow Rd Newtown , CT Extraordinary Opportunity! Live in a "like new" renovated home in sought after Poverty Ho...	3 beds \| 2 baths \| 1,253 sq.ft.	$499,900	Airbnb cash on cash: 0.74% Traditional cash on cash: 2.88% Airbnb Rental Income: $1948 Traditional Rental Income: $2434 Airbnb ROI: 0.74% Traditional ROI: 2.88%

Real Estate investment in Chaplin, CT

There are 5 properties for sale in the city of Chaplin . The median list price in Chaplin is $524,450 and the average price per square foot is $201. In September 2026, the average monthly cash on cash return in Chaplin is 5.00%. The average monthly rental income in Chaplin is $4,112.

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

There are 5 investment properties available for sale in Chaplin.

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

The ROI for Long-Term is higher than the Short-Term in Chaplin with average rental income of $4,112.

Your search for investment property begins and ends here

Investment Property for Sale in Chaplin, CT

21 Linkkila Lane

Chaplin, CT

5 beds | 4 baths | 2,760 sq.ft.

$599,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.84%

Airbnb Rental Income: $null

Traditional Rental Income: $4049

Airbnb ROI: N/A

Traditional ROI: 4.84%

287 S Bear Hill Rd

Chaplin, CT

4 beds | 2 baths | 2,900 sq.ft.

$789,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.02%

Airbnb Rental Income: $null

Traditional Rental Income: $4788

Airbnb ROI: N/A

Traditional ROI: 4.02%

13 Bates Rd

Chaplin, CT

5 beds | 2 baths | 2,887 sq.ft.

$429,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.88%

Airbnb Rental Income: $null

Traditional Rental Income: $4174

Airbnb ROI: N/A

Traditional ROI: 6.88%

Investment Properties for Sale in Other Cities of Connecticut

New Haven , CT

2 beds | 2 baths | 1,395 sq.ft.

$620,000

Airbnb cash on cash: -2.48%

Traditional cash on cash: 0.13%

Airbnb Rental Income: $1571

Traditional Rental Income: $2627

Airbnb ROI: -2.48%

Traditional ROI: 0.13%

Norwalk , CT

3 beds | 2 baths | 2,442 sq.ft.

$3,000,000

Airbnb cash on cash: -0.88%

Traditional cash on cash: -0.72%

Airbnb Rental Income: $3703

Traditional Rental Income: $3330

Airbnb ROI: -0.88%

Traditional ROI: -0.72%

Fairfield , CT

3 beds | 3 baths | 3,328 sq.ft.

$2,200,000

Airbnb cash on cash: -1.85%

Traditional cash on cash: 0.19%

Airbnb Rental Income: $2413

Traditional Rental Income: $5995

Airbnb ROI: -1.85%

Traditional ROI: 0.19%

Stonington , CT

3 beds | 3 baths | 2,632 sq.ft.

$719,000

Airbnb cash on cash: 1.72%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $3011

Traditional Rental Income: $3713

Airbnb ROI: 1.72%

Traditional ROI: 3.8%

New London , CT

2 beds | 1 baths | 1,270 sq.ft.

$329,900

Airbnb cash on cash: -2.74%

Traditional cash on cash: 0.91%

Airbnb Rental Income: $1104

Traditional Rental Income: $1864

Airbnb ROI: -2.74%

Traditional ROI: 0.91%

New London , CT

5 beds | 5 baths | 3,696 sq.ft.

$720,000