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
36 Krug Rd Preston, CT BRAND NEW ROOF! MOTIVATED SELLERS!!! If you are looking for tranquility - this is it! T...	4 beds \| 2 baths \| 2,180 sq.ft.	$474,413	Airbnb cash on cash: 2.24% Traditional cash on cash: 6.05% Airbnb Rental Income: $2462 Traditional Rental Income: $3558 Airbnb ROI: 2.24% Traditional ROI: 6.05%
42 Pierce Rd 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: -3.62% Traditional cash on cash: 8.73% Airbnb Rental Income: $604 Traditional Rental Income: $1573 Airbnb ROI: -3.62% 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: -2.75% Traditional cash on cash: -2.11% Airbnb Rental Income: $3080 Traditional Rental Income: $6249 Airbnb ROI: -2.75% Traditional ROI: -2.11%
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: 0.75% Traditional cash on cash: 3.59% Airbnb Rental Income: $2462 Traditional Rental Income: $3164 Airbnb ROI: 0.75% Traditional ROI: 3.59%
376 Route 165 Preston, CT 376 Route 165, Preston, CT 06365 \| Single Family Residential	2 beds \| 2 baths \| 1,500 sq.ft.	$515,000	Airbnb cash on cash: -1.2% Traditional cash on cash: 2.63% Airbnb Rental Income: $1447 Traditional Rental Income: $2860 Airbnb ROI: -1.2% Traditional ROI: 2.63%
86 School House Rd Preston, CT 86 School House Rd, Preston, CT 06365 \| Other	N/A beds \| N/A baths \| N/A	$299,900	Airbnb cash on cash: -1.8% Traditional cash on cash: -0.29% Airbnb Rental Income: $819 Traditional Rental Income: $956 Airbnb ROI: -1.8% Traditional ROI: -0.29%
10 Ricky Ln Preston, CT 10 Ricky Ln, Preston, CT 06365 \| Single Family Residential	4 beds \| 2 baths \| 2,357 sq.ft.	$615,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 1.73% Airbnb Rental Income: $2462 Traditional Rental Income: $3153 Airbnb ROI: -0.31% Traditional ROI: 1.73%
81 River Rd Preston, CT 81 River Rd, Preston, CT 06365 \| Single Family Residential	3 beds \| 1 baths \| 960 sq.ft.	$270,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 3.05% Airbnb Rental Income: $1797 Traditional Rental Income: $1662 Airbnb ROI: 1.66% Traditional ROI: 3.05%
76 Prodell Rd Preston, CT 76 Prodell Rd, Preston, CT 06365 \| Single Family Residential	2 beds \| 2 baths \| 1,612 sq.ft.	$369,900	Airbnb cash on cash: -0.49% Traditional cash on cash: 2.93% Airbnb Rental Income: $1447 Traditional Rental Income: $2221 Airbnb ROI: -0.49% Traditional ROI: 2.93%
83 Ross Rd Preston, CT 83 Ross Rd, Preston, CT 06365 \| Single Family Residential	3 beds \| 1 baths \| 3,318 sq.ft.	$389,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 1.18% Airbnb Rental Income: $1797 Traditional Rental Income: $1662 Airbnb ROI: 0.21% Traditional ROI: 1.18%
39 Pendleton Rd Preston, CT 39 Pendleton Rd, Preston, CT 06365 \| Single Family Residential	4 beds \| 2 baths \| 1,640 sq.ft.	$475,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 4.68% Airbnb Rental Income: $2462 Traditional Rental Income: $3558 Airbnb ROI: 0.86% Traditional ROI: 4.68%
36 Route 2A Preston, CT Take a 3D Tour OR Enjoy a Video Walkthrough 24/7! Cape-style home with full shed dormer se...	2 beds \| 2 baths \| 1,498 sq.ft.	$320,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 4.98% Airbnb Rental Income: $1447 Traditional Rental Income: $2265 Airbnb ROI: 0.83% Traditional ROI: 4.98%
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: 1.03% Traditional cash on cash: 5.04% Airbnb Rental Income: $2462 Traditional Rental Income: $4019 Airbnb ROI: 1.03% Traditional ROI: 5.04%
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: 0.46% Traditional cash on cash: 3.49% Airbnb Rental Income: $1797 Traditional Rental Income: $2770 Airbnb ROI: 0.46% Traditional ROI: 3.49%
153-A Route 12 Preston, CT Imagine waking up to sweeping water views and the gentle rhythm of Poquetanuck Cove right ...	1 beds \| 1 baths \| 1,321 sq.ft.	$499,000	Airbnb cash on cash: -1.49% Traditional cash on cash: 2.39% Airbnb Rental Income: $604 Traditional Rental Income: $2124 Airbnb ROI: -1.49% Traditional ROI: 2.39%

Real Estate investment in Preston, CT

There are 19 properties for sale in the city of Preston . The median list price in Preston is $399,450 and the average price per square foot is $266. In September 2026, the average monthly cash on cash return in Preston is 3.00%. The average monthly rental income in Preston is $2,487.

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

There are 19 investment properties available for sale in Preston.

In 2026, 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 $2,487.

Your search for investment property begins and ends here

Investment Property for Sale in Preston, CT

36 Krug Rd

Preston, CT

4 beds | 2 baths | 2,180 sq.ft.

$474,413

Airbnb cash on cash: 2.24%

Traditional cash on cash: 6.05%

Airbnb Rental Income: $2462

Traditional Rental Income: $3558

Airbnb ROI: 2.24%

Traditional ROI: 6.05%

42 Pierce Rd

Preston, CT

1 beds | 1 baths | 400 sq.ft.

$105,000

Airbnb cash on cash: -3.62%

Traditional cash on cash: 8.73%

Airbnb Rental Income: $604

Traditional Rental Income: $1573

Airbnb ROI: -3.62%

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: -2.75%

Traditional cash on cash: -2.11%

Airbnb Rental Income: $3080

Traditional Rental Income: $6249

Airbnb ROI: -2.75%

Traditional ROI: -2.11%

43 Lynn Dr

Preston, CT

4 beds | 2 baths | 2,085 sq.ft.

$489,000

Airbnb cash on cash: 0.75%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $2462

Traditional Rental Income: $3164

Airbnb ROI: 0.75%

Traditional ROI: 3.59%

376 Route 165

Preston, CT

2 beds | 2 baths | 1,500 sq.ft.

$515,000

Airbnb cash on cash: -1.2%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $1447

Traditional Rental Income: $2860

Airbnb ROI: -1.2%

Traditional ROI: 2.63%

86 School House Rd

Preston, CT

N/A beds | N/A baths | N/A

$299,900

Airbnb cash on cash: -1.8%

Traditional cash on cash: -0.29%

Airbnb Rental Income: $819

Traditional Rental Income: $956

Airbnb ROI: -1.8%

Traditional ROI: -0.29%

10 Ricky Ln

Preston, CT

4 beds | 2 baths | 2,357 sq.ft.

$615,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $2462

Traditional Rental Income: $3153

Airbnb ROI: -0.31%

Traditional ROI: 1.73%

81 River Rd

Preston, CT

3 beds | 1 baths | 960 sq.ft.

$270,000

Airbnb cash on cash: 1.66%

Traditional cash on cash: 3.05%

Airbnb Rental Income: $1797

Traditional Rental Income: $1662

Airbnb ROI: 1.66%