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: 2.35% Traditional cash on cash: 7.6% Airbnb Rental Income: $2347 Traditional Rental Income: $3697 Airbnb ROI: 2.35% 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.	$105,000	Airbnb cash on cash: -2.98% Traditional cash on cash: 8.73% Airbnb Rental Income: $682 Traditional Rental Income: $1573 Airbnb ROI: -2.98% Traditional ROI: 8.73%
57 Northwest Corner Rd Preston, CT 57 Northwest Corner Rd, Preston, CT 06365 \| Single Family Residential	9 beds \| 5 baths \| 9,784 sq.ft.	$6,500,000	Airbnb cash on cash: -2.81% Traditional cash on cash: -2.11% Airbnb Rental Income: $2670 Traditional Rental Income: $6249 Airbnb ROI: -2.81% Traditional ROI: -2.11%
11 Wheeler farm Rd Preston, CT 11 Wheeler farm Rd, Preston, CT 06365 \| Single Family Residential	4 beds \| 2 baths \| 2,285 sq.ft.	$765,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 1.23% Airbnb Rental Income: $2347 Traditional Rental Income: $3201 Airbnb ROI: -0.78% Traditional ROI: 1.23%
121 River Road Preston, CT New roof just completed at this ranch in Preston! Charming 3 BD, 2BA home set on just over...	3 beds \| 2 baths \| 1,296 sq.ft.	$355,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 5.75% Airbnb Rental Income: $1066 Traditional Rental Income: $2709 Airbnb ROI: -0.28% Traditional ROI: 5.75%
52 Middle Rd Preston, CT 52 Middle Rd, Preston, CT 06365 \| Single Family Residential	4 beds \| 2 baths \| 2,560 sq.ft.	$619,900	Airbnb cash on cash: -0.23% Traditional cash on cash: 2.18% Airbnb Rental Income: $2347 Traditional Rental Income: $3161 Airbnb ROI: -0.23% Traditional ROI: 2.18%
7 Maynard Hill Rd Preston, CT 7 Maynard Hill Rd, Preston, CT 06365 \| Single Family Residential	3 beds \| 2 baths \| 1,832 sq.ft.	$499,900	Airbnb cash on cash: -1.82% Traditional cash on cash: 2.63% Airbnb Rental Income: $1066 Traditional Rental Income: $2783 Airbnb ROI: -1.82% Traditional ROI: 2.63%
11 Tanglewood Drive Preston, CT Welcome to this beautifully designed 2,524-square-foot home at 11 Tanglewood Drive, perfec...	3 beds \| 3 baths \| 2,524 sq.ft.	$515,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 3.49% Airbnb Rental Income: $1066 Traditional Rental Income: $2770 Airbnb ROI: -0.81% Traditional ROI: 3.49%
43 Lynn Dr Preston, CT 43 Lynn Dr, Preston, CT 06365 \| Single Family Residential	4 beds \| 2 baths \| 2,085 sq.ft.	$489,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 3.59% Airbnb Rental Income: $2347 Traditional Rental Income: $3164 Airbnb ROI: 0.54% Traditional ROI: 3.59%
578 Route 165 Preston, CT Adorable three-bedroom, two-bath Cape set on just under one-acre in Preston offers an open...	3 beds \| 2 baths \| 1,498 sq.ft.	$399,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 5.67% Airbnb Rental Income: $1066 Traditional Rental Income: $3024 Airbnb ROI: -0.53% Traditional ROI: 5.67%
6 Branch Hill Road Preston, CT Take a 3D Tour or Enjoy a Video Walkthrough 24/7! Built in 2020, this one-owner 4 BR, 2.5 ...	4 beds \| 3 baths \| 2,114 sq.ft.	$575,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 5.04% Airbnb Rental Income: $2347 Traditional Rental Income: $4019 Airbnb ROI: 0.85% Traditional ROI: 5.04%

Real Estate investment in Preston, CT

There are 12 properties for sale in the city of Preston . The median list price in Preston is $399,900 and the average price per square foot is $266. In June 2026, the average monthly cash on cash return in Preston is 4.00%. The average monthly rental income in Preston is $3,093.

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

There are 12 investment properties available for sale in Preston.

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

The ROI for Short-Term is higher than the Long-Term in Preston with average rental income of $1,707.

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: 2.35%

Traditional cash on cash: 7.6%

Airbnb Rental Income: $2347

Traditional Rental Income: $3697

Airbnb ROI: 2.35%

Traditional ROI: 7.6%

42 Pierce Road

Preston, CT

1 beds | 1 baths | 400 sq.ft.

$105,000

Airbnb cash on cash: -2.98%

Traditional cash on cash: 8.73%

Airbnb Rental Income: $682

Traditional Rental Income: $1573

Airbnb ROI: -2.98%

Traditional ROI: 8.73%

57 Northwest Corner Rd

Preston, CT

9 beds | 5 baths | 9,784 sq.ft.

$6,500,000

Airbnb cash on cash: -2.81%

Traditional cash on cash: -2.11%

Airbnb Rental Income: $2670

Traditional Rental Income: $6249

Airbnb ROI: -2.81%

Traditional ROI: -2.11%

11 Wheeler farm Rd

Preston, CT

4 beds | 2 baths | 2,285 sq.ft.

$765,000

Airbnb cash on cash: -0.78%

Traditional cash on cash: 1.23%

Airbnb Rental Income: $2347

Traditional Rental Income: $3201

Airbnb ROI: -0.78%

Traditional ROI: 1.23%

121 River Road

Preston, CT

3 beds | 2 baths | 1,296 sq.ft.

$355,000

Airbnb cash on cash: -0.28%

Traditional cash on cash: 5.75%

Airbnb Rental Income: $1066

Traditional Rental Income: $2709

Airbnb ROI: -0.28%

Traditional ROI: 5.75%

52 Middle Rd

Preston, CT

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

$619,900

Airbnb cash on cash: -0.23%

Traditional cash on cash: 2.18%

Airbnb Rental Income: $2347

Traditional Rental Income: $3161

Airbnb ROI: -0.23%

Traditional ROI: 2.18%

7 Maynard Hill Rd

Preston, CT

3 beds | 2 baths | 1,832 sq.ft.

$499,900

Airbnb cash on cash: -1.82%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $1066

Traditional Rental Income: $2783

Airbnb ROI: -1.82%

Traditional ROI: 2.63%

11 Tanglewood Drive

Preston, CT

3 beds | 3 baths | 2,524 sq.ft.

$515,000

Airbnb cash on cash: -0.81%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $1066

Traditional Rental Income: $2770

Airbnb ROI: -0.81%