Real Estate Investment Properties for Sale in Redding, CT

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
299 Redding Rd Redding, CT Experience modern luxury in this beautifully renovated Colonial. A grand double-door entry...	4 beds \| 3 baths \| 4,234 sq.ft.	$979,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 5.11% Airbnb Rental Income: $3907 Traditional Rental Income: $6710 Airbnb ROI: 1.11% Traditional ROI: 5.11%
34 Fox Run Rd Redding, CT Updated Price Drop! This exceptional luxury home has just been completed and is ready to w...	5 beds \| 4 baths \| 7,833 sq.ft.	$1,550,000	Airbnb cash on cash: -1.58% Traditional cash on cash: 1.42% Airbnb Rental Income: $3818 Traditional Rental Income: $7310 Airbnb ROI: -1.58% Traditional ROI: 1.42%
71 Picketts Ridge Rd Redding, CT Tucked away like a storybook retreat, 71 Picketts Ridge is a charming and cozy ranch-style...	2 beds \| 1 baths \| 930 sq.ft.	$539,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 1.07% Airbnb Rental Income: $1522 Traditional Rental Income: $1811 Airbnb ROI: -0.38% Traditional ROI: 1.07%
7 Peaceable Street Redding, CT Step into a piece of Redding history with this charming circa 1850 cottage-style home, exh...	2 beds \| 2 baths \| 900 sq.ft.	$480,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 3.52% Airbnb Rental Income: $1522 Traditional Rental Income: $2741 Airbnb ROI: -0.18% Traditional ROI: 3.52%
Investment Properties for Sale in Other Cities of Connecticut
23 Heaton Street Waterbury , CT Beautiful 3-Bedroom Home Built in 2009 - Move-In Ready! Welcome to 23 Heaton Street, a wel...	3 beds \| 3 baths \| 1,716 sq.ft.	$374,995	Airbnb cash on cash: -0.35% Traditional cash on cash: 3.94% Airbnb Rental Income: $1673 Traditional Rental Income: $2715 Airbnb ROI: -0.35% Traditional ROI: 3.94%
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.	$2,399,000	Airbnb cash on cash: -1.79% Traditional cash on cash: 0.1% Airbnb Rental Income: $2373 Traditional Rental Income: $5995 Airbnb ROI: -1.79% Traditional ROI: 0.1%
23 Arcadia Ave Stratford , CT GORGEOUS NORTHEN PARADISE GREEN CAPE THAT WILL HIT ALL THE HIGH NOTES FOR YOUR BUYER! BRAN...	3 beds \| 2 baths \| 1,653 sq.ft.	$525,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 4.22% Airbnb Rental Income: $2065 Traditional Rental Income: $3241 Airbnb ROI: 0.73% Traditional ROI: 4.22%
360 N Society Road Canterbury , CT INSTANT EQUITY when you finish this SPRAWLING Cape it COMPS out $525,000 to $550,000! OVER...	3 beds \| 2 baths \| 2,236 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.03% Airbnb Rental Income: $null Traditional Rental Income: $3171 Airbnb ROI: N/A Traditional ROI: 9.03%
19 Clover Court New London , CT Investor Alert - Well maintained 3 bedroom colonial on a dead end street with paved drivew...	3 beds \| 1 baths \| 1,311 sq.ft.	$209,900	Airbnb cash on cash: 4.83% Traditional cash on cash: 7.84% Airbnb Rental Income: $2087 Traditional Rental Income: $2148 Airbnb ROI: 4.83% Traditional ROI: 7.84%
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.	$262,500	Airbnb cash on cash: 0.32% Traditional cash on cash: 4.33% Airbnb Rental Income: $1178 Traditional Rental Income: $1785 Airbnb ROI: 0.32% Traditional ROI: 4.33%
1 Broad Street #PHD2 Stamford , CT Luxury living at its finest. Park Tower 35th floor Penthouse Duplex boasting living room w...	3 beds \| 4 baths \| 3,341 sq.ft.	$2,000,000	Airbnb cash on cash: -3.84% Traditional cash on cash: -1.35% Airbnb Rental Income: $2038 Traditional Rental Income: $6132 Airbnb ROI: -3.84% Traditional ROI: -1.35%
286 Moose Hill Rd Monroe , CT Welcome to this well maintained ranch style home nestled away from nearby amenities, but c...	2 beds \| 1 baths \| 1,012 sq.ft.	$549,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 2.7% Airbnb Rental Income: $2198 Traditional Rental Income: $2727 Airbnb ROI: 0.59% Traditional ROI: 2.7%
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%
262 Great Plain Rd #17 Danbury , CT NEWLY REMODELED CABIN IN LAKE COMMUNITY. WALK TO BEACH. LARGE SHED FOR STORAGE. LAKE VIEWS...	2 beds \| 1 baths \| 578 sq.ft.	$239,000	Airbnb cash on cash: 3.18% Traditional cash on cash: 3.1% Airbnb Rental Income: $1708 Traditional Rental Income: $1218 Airbnb ROI: 3.18% Traditional ROI: 3.1%
619 Queen St Bridgeport , CT Here's your chance to own a highly sought-after rental property in Bridgeport's North End,...	3 beds \| 1 baths \| 864 sq.ft.	$359,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 3.88% Airbnb Rental Income: $1671 Traditional Rental Income: $2273 Airbnb ROI: 0.71% Traditional ROI: 3.88%

Real Estate investment in Redding, CT

There are 4 properties for sale in the city of Redding . The median list price in Redding is $427,000 and the average price per square foot is $221. In February 2026, the average monthly cash on cash return in Redding is 2.00%. The average monthly rental income in Redding is $4,726.

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

There are 4 investment properties available for sale in Redding.

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

The ROI for Short-Term is higher than the Long-Term in Redding with average rental income of $2,670.

Your search for investment property begins and ends here

Investment Property for Sale in Redding, CT

299 Redding Rd

Redding, CT

4 beds | 3 baths | 4,234 sq.ft.

$979,000

Airbnb cash on cash: 1.11%

Traditional cash on cash: 5.11%

Airbnb Rental Income: $3907

Traditional Rental Income: $6710

Airbnb ROI: 1.11%

Traditional ROI: 5.11%

34 Fox Run Rd

Redding, CT

5 beds | 4 baths | 7,833 sq.ft.

$1,550,000

Airbnb cash on cash: -1.58%

Traditional cash on cash: 1.42%

Airbnb Rental Income: $3818

Traditional Rental Income: $7310

Airbnb ROI: -1.58%

Traditional ROI: 1.42%

71 Picketts Ridge Rd

Redding, CT

2 beds | 1 baths | 930 sq.ft.

$539,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 1.07%

Airbnb Rental Income: $1522

Traditional Rental Income: $1811

Airbnb ROI: -0.38%

Traditional ROI: 1.07%

7 Peaceable Street

Redding, CT

2 beds | 2 baths | 900 sq.ft.

$480,000

Airbnb cash on cash: -0.18%

Traditional cash on cash: 3.52%

Airbnb Rental Income: $1522

Traditional Rental Income: $2741

Airbnb ROI: -0.18%

Traditional ROI: 3.52%

Investment Properties for Sale in Other Cities of Connecticut

Waterbury , CT

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

$374,995

Airbnb cash on cash: -0.35%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $1673

Traditional Rental Income: $2715

Airbnb ROI: -0.35%

Traditional ROI: 3.94%

Fairfield , CT

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

$2,399,000

Airbnb cash on cash: -1.79%

Traditional cash on cash: 0.1%

Airbnb Rental Income: $2373

Traditional Rental Income: $5995

Airbnb ROI: -1.79%

Traditional ROI: 0.1%

Stratford , CT

3 beds | 2 baths | 1,653 sq.ft.

$525,000

Airbnb cash on cash: 0.73%

Traditional cash on cash: 4.22%

Airbnb Rental Income: $2065

Traditional Rental Income: $3241

Airbnb ROI: 0.73%

Traditional ROI: 4.22%

Canterbury , CT

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

$275,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.03%

Airbnb Rental Income: $null

Traditional Rental Income: $3171

Airbnb ROI: N/A

Traditional ROI: 9.03%

New London , CT

3 beds | 1 baths | 1,311 sq.ft.