Real Estate Investment Properties for Sale in Preston, CT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
70 SCHOOL HOUSE Preston, CT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	4 beds \| 3 baths \| 2,061 sq.ft.	$392,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 7.6% Airbnb Rental Income: $2257 Traditional Rental Income: $3697 Airbnb ROI: 2.14% Traditional ROI: 7.6%
42 Pierce Road Preston, CT Just come and relax in your own place at Strawberry Park, it has a lot to offer you, gated...	1 beds \| 1 baths \| 400 sq.ft.	$99,900	Airbnb cash on cash: 4.44% Traditional cash on cash: 9.88% Airbnb Rental Income: $1480 Traditional Rental Income: $1573 Airbnb ROI: 4.44% Traditional ROI: 9.88%
59 Harris Fuller Road Preston, CT Welcome to 59 Harris Fuller Rd in Preston, CT - a beautifully crafted home that blends tim...	3 beds \| 3 baths \| 3,231 sq.ft.	$624,900	Airbnb cash on cash: -1.67% Traditional cash on cash: 3.1% Airbnb Rental Income: $1354 Traditional Rental Income: $3725 Airbnb ROI: -1.67% Traditional ROI: 3.1%
381 Route 2 Preston, CT This 2 family has it all. Sits up on a small knoll far off the road but on 4.77 open flat ...	6 beds \| 2 baths \| 1,899 sq.ft.	$459,000	Airbnb cash on cash: 1.31% Traditional cash on cash: 4.4% Airbnb Rental Income: $2625 Traditional Rental Income: $3323 Airbnb ROI: 1.31% Traditional ROI: 4.4%
Investment Properties for Sale in Other Cities of Connecticut
23 Heaton Street Waterbury , CT Welcome to this inviting 3-bedroom, 3-bathroom home offering 1,716 sq ft of living space i...	3 beds \| 3 baths \| 1,716 sq.ft.	$399,995	Airbnb cash on cash: 0.1% Traditional cash on cash: 4.12% Airbnb Rental Income: $1673 Traditional Rental Income: $2715 Airbnb ROI: 0.1% Traditional ROI: 4.12%
2 Elmwood Drive #2 Fairfield , CT Rare offering in the coveted Southport Green complex, just steps from Southport Village an...	3 beds \| 4 baths \| 3,328 sq.ft.	$2,495,000	Airbnb cash on cash: -1.53% Traditional cash on cash: 0.29% Airbnb Rental Income: $2373 Traditional Rental Income: $5995 Airbnb ROI: -1.53% Traditional ROI: 0.29%
360 North Society Road Canterbury , CT INSTANT EQUITY when you finish this SPRAWLING Cape it COMPS out at $499,900!! OVERSIZED 2 ...	3 beds \| 2 baths \| 2,236 sq.ft.	$289,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.16% Airbnb Rental Income: $null Traditional Rental Income: $3171 Airbnb ROI: N/A Traditional ROI: 8.16%
15 Capewell Drive Bloomfield , CT Tucked away on a quiet tree-lined street, this beautifully reimagined ranch feels like a f...	3 beds \| 1 baths \| 1,279 sq.ft.	$329,990	Airbnb cash on cash: -0.46% Traditional cash on cash: 5.67% Airbnb Rental Income: $850 Traditional Rental Income: $2420 Airbnb ROI: -0.46% Traditional ROI: 5.67%
32 WILLINGTON AVENUE Stafford Springs , CT Completely renovated old-style Colonial that sits on1.72 private acres. Nestled in the woo...	3 beds \| 2 baths \| 1,047 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.4% Airbnb Rental Income: $null Traditional Rental Income: $2593 Airbnb ROI: N/A Traditional ROI: 5.4%
2 Currier Court #2 Cheshire , CT Currier Woods is located in a 160-unit community known for its mature trees, private windi...	2 beds \| 2 baths \| 1,362 sq.ft.	$319,900	Airbnb cash on cash: 1.62% Traditional cash on cash: 5.57% Airbnb Rental Income: $1889 Traditional Rental Income: $2572 Airbnb ROI: 1.62% Traditional ROI: 5.57%
153 THOMPSON HILL RD Portland , CT Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 2 baths \| 1,704 sq.ft.	$451,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.54% Airbnb Rental Income: $1906 Traditional Rental Income: $2560 Airbnb ROI: 0.79% Traditional ROI: 3.54%
180 East Rocks Road Norwalk , CT Welcome to 180 East Rocks Road in the desirable Cranbury neighborhood. Experience comfort ...	4 beds \| 3 baths \| 3,332 sq.ft.	$1,050,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 3.48% Airbnb Rental Income: $4407 Traditional Rental Income: $5637 Airbnb ROI: 1.28% Traditional ROI: 3.48%
114 Terrill Road Stratford , CT Welcome to this charming Paradise Green Ranch, perfectly situated within walking distance ...	3 beds \| 2 baths \| 1,922 sq.ft.	$424,900	Airbnb cash on cash: 1.68% Traditional cash on cash: 5.92% Airbnb Rental Income: $2272 Traditional Rental Income: $3394 Airbnb ROI: 1.68% Traditional ROI: 5.92%
23 Pemberwick Road Greenwich , CT This storybook Pemberwick Colonial is an ideal condo alternative and oodles of character f...	2 beds \| 2 baths \| 1,169 sq.ft.	$695,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 3.22% Airbnb Rental Income: $2158 Traditional Rental Income: $3272 Airbnb ROI: 0.65% Traditional ROI: 3.22%
109 Timber Trail Tolland , CT Welcome to 109 Timber Trail in Tolland! This beautiful 4-bedroom, 3-bath home combines tho...	4 beds \| 3 baths \| 2,884 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.66% Airbnb Rental Income: $null Traditional Rental Income: $4437 Airbnb ROI: N/A Traditional ROI: 8.66%

Real Estate investment in Preston, CT

There are 4 properties for sale in the city of Preston . The median list price in Preston is $425,500 and the average price per square foot is $224. In October 2025, the average monthly cash on cash return in Preston is 6.00%. The average monthly rental income in Preston is $3,510.

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

There are 4 investment properties available for sale in Preston.

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

The ROI for Long-Term is higher than the Short-Term in Preston with average rental income of $3,510.

Your search for investment property begins and ends here

Investment Property for Sale in Preston, CT

70 SCHOOL HOUSE

Preston, CT

4 beds | 3 baths | 2,061 sq.ft.

$392,000

Airbnb cash on cash: 2.14%

Traditional cash on cash: 7.6%

Airbnb Rental Income: $2257

Traditional Rental Income: $3697

Airbnb ROI: 2.14%

Traditional ROI: 7.6%

42 Pierce Road

Preston, CT

1 beds | 1 baths | 400 sq.ft.

$99,900

Airbnb cash on cash: 4.44%

Traditional cash on cash: 9.88%

Airbnb Rental Income: $1480

Traditional Rental Income: $1573

Airbnb ROI: 4.44%

Traditional ROI: 9.88%

59 Harris Fuller Road

Preston, CT

3 beds | 3 baths | 3,231 sq.ft.

$624,900

Airbnb cash on cash: -1.67%

Traditional cash on cash: 3.1%

Airbnb Rental Income: $1354

Traditional Rental Income: $3725

Airbnb ROI: -1.67%

Traditional ROI: 3.1%

381 Route 2

Preston, CT

6 beds | 2 baths | 1,899 sq.ft.

$459,000

Airbnb cash on cash: 1.31%

Traditional cash on cash: 4.4%

Airbnb Rental Income: $2625

Traditional Rental Income: $3323

Airbnb ROI: 1.31%

Traditional ROI: 4.4%

Investment Properties for Sale in Other Cities of Connecticut

Waterbury , CT

3 beds | 3 baths | 1,716 sq.ft.

$399,995

Airbnb cash on cash: 0.1%

Traditional cash on cash: 4.12%

Airbnb Rental Income: $1673

Traditional Rental Income: $2715

Airbnb ROI: 0.1%

Traditional ROI: 4.12%

Fairfield , CT

3 beds | 4 baths | 3,328 sq.ft.

$2,495,000

Airbnb cash on cash: -1.53%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $2373

Traditional Rental Income: $5995

Airbnb ROI: -1.53%

Traditional ROI: 0.29%

Canterbury , CT

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

$289,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.16%

Airbnb Rental Income: $null

Traditional Rental Income: $3171

Airbnb ROI: N/A

Traditional ROI: 8.16%

Bloomfield , CT

3 beds | 1 baths | 1,279 sq.ft.

$329,990

Airbnb cash on cash: -0.46%

Traditional cash on cash: 5.67%

Airbnb Rental Income: $850

Traditional Rental Income: $2420

Airbnb ROI: -0.46%

Traditional ROI: 5.67%

Stafford Springs , CT

3 beds | 2 baths | 1,047 sq.ft.