Real Estate Investment Properties for Sale in Woodbridge, CT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
15 Shady Lane Woodbridge, CT Welcome to this expansive, oversized ranch nestled on a large lot in a serene cul-de-sac. ...	3 beds \| 3 baths \| 3,425 sq.ft.	$630,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 3.79% Airbnb Rental Income: $2708 Traditional Rental Income: $3775 Airbnb ROI: 0.88% Traditional ROI: 3.79%
106 seymour Road Woodbridge, CT Introducing 106 Seymour Road, Woodbridge, CT: a luxurious 3,700 sq. ft. modern farmhouse t...	4 beds \| 5 baths \| 5,200 sq.ft.	$1,488,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 3.1% Airbnb Rental Income: $3717 Traditional Rental Income: $6199 Airbnb ROI: 0.72% Traditional ROI: 3.1%
16 Cleft Rock Road Woodbridge, CT Escape to the privacy of this 7.65-acre Stoddard Hill Estate, a haven for enjoying breatht...	4 beds \| 8 baths \| 8,909 sq.ft.	$2,850,000	Airbnb cash on cash: -2.07% Traditional cash on cash: -0.42% Airbnb Rental Income: $3717 Traditional Rental Income: $7256 Airbnb ROI: -2.07% Traditional ROI: -0.42%
1221 Racebrook Road Woodbridge, CT Discover the perfect blend of luxury and comfort in this spacious mid-century contemporary...	4 beds \| 5 baths \| 3,224 sq.ft.	$514,900	Airbnb cash on cash: 2.27% Traditional cash on cash: 9.67% Airbnb Rental Income: $3717 Traditional Rental Income: $6475 Airbnb ROI: 2.27% Traditional ROI: 9.67%
40 Old Quarry Road Woodbridge, CT Prepare to be enchanted by this idyllic Contemporary Colonial featuring 5364SF of elegance...	5 beds \| 5 baths \| 5,364 sq.ft.	$839,900	Airbnb cash on cash: 2.22% Traditional cash on cash: 6.85% Airbnb Rental Income: $5361 Traditional Rental Income: $7899 Airbnb ROI: 2.22% Traditional ROI: 6.85%
126 Pease Road Woodbridge, CT A majestic & stately brick colonial w 5 bedrooms, 5 full bathrooms, 1 half bathroom & appr...	5 beds \| 6 baths \| 5,965 sq.ft.	$1,238,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 3.25% Airbnb Rental Income: $5361 Traditional Rental Income: $7437 Airbnb ROI: 0.51% Traditional ROI: 3.25%
25 Hickory Road Woodbridge, CT Come home to this exceptional cape cod in Woodbridge's Stoddard Hill area. Beautiful prope...	5 beds \| 5 baths \| 6,070 sq.ft.	$729,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 6.28% Airbnb Rental Income: $5361 Traditional Rental Income: $6486 Airbnb ROI: 3.03% Traditional ROI: 6.28%
38 Wepawaug Road Woodbridge, CT Charming Woodbridge Home in Prime Location. Don't miss this rare opportunity to own a beau...	3 beds \| 2 baths \| 1,724 sq.ft.	$550,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 2.23% Airbnb Rental Income: $2708 Traditional Rental Income: $2843 Airbnb ROI: 0.72% Traditional ROI: 2.23%
38 Ox Bow Lane Woodbridge, CT Equestrian friendly, 3 bedrooms, 2.5 bath, well-built home on 5+ acres in Woodbridge, CT. ...	3 beds \| 3 baths \| 2,688 sq.ft.	$589,900	Airbnb cash on cash: 0.46% Traditional cash on cash: 3.64% Airbnb Rental Income: $2708 Traditional Rental Income: $3818 Airbnb ROI: 0.46% Traditional ROI: 3.64%
15 Park Lane Woodbridge, CT Welcome to this delightful ranch-style home in a serene neighborhood, offering a tranquil ...	3 beds \| 2 baths \| 1,380 sq.ft.	$499,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 2.57% Airbnb Rental Income: $2708 Traditional Rental Income: $2748 Airbnb ROI: 1.11% Traditional ROI: 2.57%
4 Ranch Road Woodbridge, CT One level living at its finest! Oversized ranch on 1.4 acres in near pristine condition. O...	4 beds \| 2 baths \| 2,138 sq.ft.	$639,900	Airbnb cash on cash: 1.59% Traditional cash on cash: 1.88% Airbnb Rental Income: $3717 Traditional Rental Income: $3084 Airbnb ROI: 1.59% Traditional ROI: 1.88%
9 Acorn Hill Road Woodbridge, CT Welcome to 9 Acorn Hill Road, Woodbridge, CT - a stunning new construction home offering 3...	4 beds \| 4 baths \| 3,437 sq.ft.	$1,149,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 1.11% Airbnb Rental Income: $3717 Traditional Rental Income: $4620 Airbnb ROI: -0.49% Traditional ROI: 1.11%
2 Hillcrest Drive #2 Woodbridge, CT You'll love living at the Regency at Woodbridge! Welcome to resort style living in this co...	3 beds \| 3 baths \| 2,486 sq.ft.	$799,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 1.45% Airbnb Rental Income: $2708 Traditional Rental Income: $3998 Airbnb ROI: -1.14% Traditional ROI: 1.45%
32 Manila Avenue Woodbridge, CT Welcome to 32 Manila Avenue, a unique single family setup on a quiet Woodbridge street, pe...	3 beds \| 2 baths \| 1,196 sq.ft.	$350,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 4.36% Airbnb Rental Income: $2708 Traditional Rental Income: $2551 Airbnb ROI: 2.89% Traditional ROI: 4.36%
18 Westward Road Woodbridge, CT Situated on a stately 2.24 acres, this beautiful Contemporary Cape, seamlessly blends mode...	5 beds \| 5 baths \| 6,298 sq.ft.	$1,199,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 2.59% Airbnb Rental Income: $5361 Traditional Rental Income: $6471 Airbnb ROI: 0.62% Traditional ROI: 2.59%
88 Maple Vale Drive Woodbridge, CT Beautifully updated unique split level with possible in- law set up. This massive split le...	5 beds \| 5 baths \| 3,426 sq.ft.	$749,900	Airbnb cash on cash: 2.86% Traditional cash on cash: 5.87% Airbnb Rental Income: $5361 Traditional Rental Income: $6384 Airbnb ROI: 2.86% Traditional ROI: 5.87%
5 Diana Drive Woodbridge, CT Welcome to 5 Diana Drive, an elegant Colonial-style home offering 3,629 square feet of liv...	5 beds \| 5 baths \| 3,629 sq.ft.	$749,900	Airbnb cash on cash: 2.86% Traditional cash on cash: 8.89% Airbnb Rental Income: $5361 Traditional Rental Income: $8493 Airbnb ROI: 2.86% Traditional ROI: 8.89%
9 Dillon Road Woodbridge, CT Discover the allure of Whispering Pines, a captivating 1930s estate nestled amidst the lus...	4 beds \| 3 baths \| 2,123 sq.ft.	$749,900	Airbnb cash on cash: 0.9% Traditional cash on cash: 2.81% Airbnb Rental Income: $3717 Traditional Rental Income: $4243 Airbnb ROI: 0.9% Traditional ROI: 2.81%
19 Meadowbrook Road Woodbridge, CT Looking for a place in Woodbridge to make your own? Beautiful, secluded, flat lot of 2.76 ...	4 beds \| 4 baths \| 2,715 sq.ft.	$530,000	Airbnb cash on cash: 2.56% Traditional cash on cash: 8.55% Airbnb Rental Income: $3717 Traditional Rental Income: $5874 Airbnb ROI: 2.56% Traditional ROI: 8.55%

Real Estate investment in Woodbridge, CT

There are 19 properties for sale in the city of Woodbridge . The median list price in Woodbridge is $749,900 and the average price per square foot is $200. In December 2024, the average monthly cash on cash return in Woodbridge is 3.00%. The average monthly rental income in Woodbridge is $5,874.

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

There are 19 investment properties available for sale in Woodbridge.

In 2024, the best neighborhood to buy investment property is Woodbridge.

The ROI for Long-Term is higher than the Short-Term in Woodbridge with average rental income of $5,874.

Your search for investment property begins and ends here

Investment Property for Sale in Woodbridge, CT

15 Shady Lane

Woodbridge, CT

3 beds | 3 baths | 3,425 sq.ft.

$630,000

Airbnb cash on cash: 0.88%

Traditional cash on cash: 3.79%

Airbnb Rental Income: $2708

Traditional Rental Income: $3775

Airbnb ROI: 0.88%

Traditional ROI: 3.79%

106 seymour Road

Woodbridge, CT

4 beds | 5 baths | 5,200 sq.ft.

$1,488,000

Airbnb cash on cash: 0.72%

Traditional cash on cash: 3.1%

Airbnb Rental Income: $3717

Traditional Rental Income: $6199

Airbnb ROI: 0.72%

Traditional ROI: 3.1%

16 Cleft Rock Road

Woodbridge, CT

4 beds | 8 baths | 8,909 sq.ft.

$2,850,000

Airbnb cash on cash: -2.07%

Traditional cash on cash: -0.42%

Airbnb Rental Income: $3717

Traditional Rental Income: $7256

Airbnb ROI: -2.07%

Traditional ROI: -0.42%

1221 Racebrook Road

Woodbridge, CT

4 beds | 5 baths | 3,224 sq.ft.

$514,900

Airbnb cash on cash: 2.27%

Traditional cash on cash: 9.67%

Airbnb Rental Income: $3717

Traditional Rental Income: $6475

Airbnb ROI: 2.27%

Traditional ROI: 9.67%

40 Old Quarry Road

Woodbridge, CT

5 beds | 5 baths | 5,364 sq.ft.

$839,900

Airbnb cash on cash: 2.22%

Traditional cash on cash: 6.85%

Airbnb Rental Income: $5361

Traditional Rental Income: $7899

Airbnb ROI: 2.22%

Traditional ROI: 6.85%

126 Pease Road

Woodbridge, CT

5 beds | 6 baths | 5,965 sq.ft.

$1,238,000

Airbnb cash on cash: 0.51%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $5361

Traditional Rental Income: $7437

Airbnb ROI: 0.51%

Traditional ROI: 3.25%

25 Hickory Road

Woodbridge, CT

5 beds | 5 baths | 6,070 sq.ft.

$729,000

Airbnb cash on cash: 3.03%

Traditional cash on cash: 6.28%

Airbnb Rental Income: $5361

Traditional Rental Income: $6486

Airbnb ROI: 3.03%

Traditional ROI: 6.28%

38 Wepawaug Road

Woodbridge, CT

3 beds | 2 baths | 1,724 sq.ft.

$550,000

Airbnb cash on cash: 0.72%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $2708

Traditional Rental Income: $2843

Airbnb ROI: 0.72%