Real Estate Investment Properties for Sale in Watertown, CT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
104 Northwest Drive Watertown, CT Custom Craftsmanship, Unparalleled Curbside Appeal, and Pride of ownership to a Majestic M...	4 beds \| 3 baths \| 2,880 sq.ft.	$615,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.07% Airbnb Rental Income: $null Traditional Rental Income: $4421 Airbnb ROI: N/A Traditional ROI: 5.07%
368 Hamilton Avenue Watertown, CT Set in the highly sought-after Taft area, this 3-bedroom, 2-bath Cape offers a spacious 1....	3 beds \| 2 baths \| 1,238 sq.ft.	$365,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 5.05% Airbnb Rental Income: $1991 Traditional Rental Income: $2673 Airbnb ROI: 1.54% Traditional ROI: 5.05%
56 Orient Street Watertown, CT Welcome to 56 Orient Street, a beautifully updated 4-bedroom, 2-full-bath home has over 1,...	4 beds \| 2 baths \| 996 sq.ft.	$379,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.98% Airbnb Rental Income: $null Traditional Rental Income: $2689 Airbnb ROI: N/A Traditional ROI: 4.98%
21 Lancaster Street Watertown, CT Welcome to 21 Lancaster Street in Watertown! This well-maintained 3-bedroom raised ranch o...	3 beds \| 2 baths \| 1,484 sq.ft.	$365,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 3.25% Airbnb Rental Income: $1991 Traditional Rental Income: $2125 Airbnb ROI: 1.34% Traditional ROI: 3.25%
555 Davis Street Watertown, CT Single Owner - Custom Built 3093sqft all Brick and Stone Colonial set on 6.11 estate like ...	3 beds \| 3 baths \| 3,893 sq.ft.	$800,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 2.66% Airbnb Rental Income: $1991 Traditional Rental Income: $3904 Airbnb ROI: -0.61% Traditional ROI: 2.66%
6 Burnham Street Watertown, CT Welcome to 6 Burnham St in Watertown, located in the section of town formerly known as Oak...	3 beds \| 2 baths \| 1,498 sq.ft.	$375,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 5.33% Airbnb Rental Income: $1991 Traditional Rental Income: $2845 Airbnb ROI: 1.42% Traditional ROI: 5.33%
4 Bayview Circle Watertown, CT Welcome to 4 Bayview Circle, Watertown, CT! This 3-bedroom, 2-bath Ranch offers approximat...	3 beds \| 2 baths \| 1,688 sq.ft.	$514,900	Airbnb cash on cash: 0.18% Traditional cash on cash: 3.27% Airbnb Rental Income: $1991 Traditional Rental Income: $2957 Airbnb ROI: 0.18% Traditional ROI: 3.27%
96 Neill Drive Watertown, CT WELCOME to 96 Neill Drive this Beautifully remodeled Colonial with Finished basement, loca...	5 beds \| 4 baths \| 4,400 sq.ft.	$599,900	Airbnb cash on cash: 2.06% Traditional cash on cash: 8.45% Airbnb Rental Income: $3643 Traditional Rental Income: $6425 Airbnb ROI: 2.06% Traditional ROI: 8.45%
27 Roberts Avenue Watertown, CT Rich in New England charm, this Colonial blends timeless character with inviting outdoor s...	4 beds \| 2 baths \| 1,620 sq.ft.	$459,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.19% Airbnb Rental Income: $null Traditional Rental Income: $3409 Airbnb ROI: N/A Traditional ROI: 5.19%
75 Turnberry Court #18 Watertown, CT Easy Living Begins at Turnberry Estates - a thoughtfully designed 55+ adult community offe...	3 beds \| 3 baths \| 2,339 sq.ft.	$610,700	Airbnb cash on cash: -0.71% Traditional cash on cash: 2.5% Airbnb Rental Income: $1991 Traditional Rental Income: $3297 Airbnb ROI: -0.71% Traditional ROI: 2.5%
71 Turnberry Court #17 Watertown, CT Easy Living Begins at Turnberry Estates - a thoughtfully designed 55+ adult community offe...	3 beds \| 3 baths \| 1,778 sq.ft.	$558,465	Airbnb cash on cash: -0.48% Traditional cash on cash: 3% Airbnb Rental Income: $1991 Traditional Rental Income: $3288 Airbnb ROI: -0.48% Traditional ROI: 3%
603 Sunnyside Avenue Watertown, CT Move-In Ready! Welcome home to this beautifully renovated 3-bedroom, 1.5-bath Ranch offeri...	3 beds \| 2 baths \| 1,382 sq.ft.	$375,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.93% Airbnb Rental Income: $1991 Traditional Rental Income: $2337 Airbnb ROI: 1.47% Traditional ROI: 3.93%
541 Middlebury Road Watertown, CT Discover comfort and space in this 2,500+ sq ft, 4-bedroom 3-1/2 bath Colonial situated on...	4 beds \| 3 baths \| 2,496 sq.ft.	$469,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.61% Airbnb Rental Income: $null Traditional Rental Income: $5084 Airbnb ROI: N/A Traditional ROI: 8.61%
82 Nova Scotia Hill Road Watertown, CT Story Book Setting and the house to match. Come see this beautiful home and you will not w...	5 beds \| 4 baths \| 2,890 sq.ft.	$665,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 7.13% Airbnb Rental Income: $3643 Traditional Rental Income: $6062 Airbnb ROI: 1.94% Traditional ROI: 7.13%
805 Main Street Watertown, CT Rare opportunity to acquire a well-maintained 28-unit multifamily portfolio spanning 8 bui...	7 beds \| 3 baths \| 2,688 sq.ft.	$3,668,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 0.2% Airbnb Rental Income: $3643 Traditional Rental Income: $4640 Airbnb ROI: -0.33% Traditional ROI: 0.2%
77 Westbury Park Road Watertown, CT Investors delight! A Prime, downtown located, aesthetically appealing, 1500 sf+, 2 family ...	4 beds \| 2 baths \| 1,568 sq.ft.	$379,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.92% Airbnb Rental Income: $null Traditional Rental Income: $3338 Airbnb ROI: N/A Traditional ROI: 6.92%
245 Cherry Avenue #O21 Watertown, CT Charming One- Bedroom Condominium with a Beautiful Tree-Lined View!! Welcome home to this ...	1 beds \| 1 baths \| 728 sq.ft.	$179,900	Airbnb cash on cash: -0.81% Traditional cash on cash: 4.34% Airbnb Rental Income: $1156 Traditional Rental Income: $1657 Airbnb ROI: -0.81% Traditional ROI: 4.34%
136 Bamford Avenue Watertown, CT Welcome to 136 Bamford Avenue, a great opportunity in Oakville! This three-bedroom, one-ba...	3 beds \| 1 baths \| 1,148 sq.ft.	$300,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 4.82% Airbnb Rental Income: $1991 Traditional Rental Income: $2273 Airbnb ROI: 1.98% Traditional ROI: 4.82%
57 Sunnyside Avenue Watertown, CT ATTENTION INVESTORS & OWNER-OCCUPANTS! This longtime-owned two-family in the Oakville sect...	4 beds \| 2 baths \| 2,808 sq.ft.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.02% Airbnb Rental Income: $null Traditional Rental Income: $3875 Airbnb ROI: N/A Traditional ROI: 9.02%
600 Thomaston Road Watertown, CT Make no mistake - this house is perfect for a handy person looking for a great opportunity...	3 beds \| 2 baths \| 2,304 sq.ft.	$364,900	Airbnb cash on cash: 1.07% Traditional cash on cash: 6.58% Airbnb Rental Income: $1991 Traditional Rental Income: $3357 Airbnb ROI: 1.07% Traditional ROI: 6.58%
19 Pythian Avenue Watertown, CT ASSUMABLE MORTGAGE 5.5%. Investor-ready three-unit multifamily offering strong cash-flow p...	8 beds \| 3 baths \| 2,180 sq.ft.	$435,000	Airbnb cash on cash: 4.61% Traditional cash on cash: 6.28% Airbnb Rental Income: $3643 Traditional Rental Income: $3526 Airbnb ROI: 4.61% Traditional ROI: 6.28%
114 Plainfield Drive Watertown, CT Well-maintained and move-in ready, this spacious split-level home offers a flexible layout...	4 beds \| 2 baths \| 2,044 sq.ft.	$384,999	Airbnb cash on cash: N/A Traditional cash on cash: 7.19% Airbnb Rental Income: $null Traditional Rental Income: $3586 Airbnb ROI: N/A Traditional ROI: 7.19%
145 Edge Road Watertown, CT Welcome to 145 Edge Road! This beautifully updated, move-in-ready raised ranch offers a br...	3 beds \| 2 baths \| 1,241 sq.ft.	$460,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 3.87% Airbnb Rental Income: $1991 Traditional Rental Income: $2778 Airbnb ROI: 0.83% Traditional ROI: 3.87%
70 Eastwood Hall Road Watertown, CT Located in Watertown's desirable Taft area with views of Watertown Golf Club, this 3 bedro...	3 beds \| 3 baths \| 2,128 sq.ft.	$615,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 3.87% Airbnb Rental Income: $1991 Traditional Rental Income: $3632 Airbnb ROI: 0.1% Traditional ROI: 3.87%
275 Davis Street Watertown, CT Welcome to 275 Davis Street, a well-cared-for 1945 two-story home in a convenient Oakville...	2 beds \| 1 baths \| 1,136 sq.ft.	$309,900	Airbnb cash on cash: 0.57% Traditional cash on cash: 4.4% Airbnb Rental Income: $1392 Traditional Rental Income: $2087 Airbnb ROI: 0.57% Traditional ROI: 4.4%
26 Shelter Hill Avenue Watertown, CT Opportunity knocks in sought-after Oakville! This move-in ready 3-bedroom ranch has the up...	3 beds \| 1 baths \| 1,080 sq.ft.	$310,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 4.32% Airbnb Rental Income: $1991 Traditional Rental Income: $2171 Airbnb ROI: 1.92% Traditional ROI: 4.32%
35 Hubbell Avenue Watertown, CT Two-family opportunity in the Oakville section of Watertown! 35 Hubbell Avenue offers two ...	4 beds \| 2 baths \| 1,596 sq.ft.	$339,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.75% Airbnb Rental Income: $null Traditional Rental Income: $3284 Airbnb ROI: N/A Traditional ROI: 7.75%
79 Turnberry Court #19 Watertown, CT Easy Living Begins at Turnberry Estates - a thoughtfully designed 55+ adult community offe...	3 beds \| 2 baths \| 1,821 sq.ft.	$590,480	Airbnb cash on cash: -0.63% Traditional cash on cash: 1.75% Airbnb Rental Income: $1991 Traditional Rental Income: $2781 Airbnb ROI: -0.63% Traditional ROI: 1.75%
174 Turnberry Court #34 Watertown, CT Easy Living Begins at Turnberry Estates - a thoughtfully designed 55+ adult community offe...	3 beds \| 2 baths \| 1,820 sq.ft.	$632,437	Airbnb cash on cash: -0.79% Traditional cash on cash: 1.85% Airbnb Rental Income: $1991 Traditional Rental Income: $3029 Airbnb ROI: -0.79% Traditional ROI: 1.85%
132 Turnberry Court #26 Watertown, CT Easy Living Begins at Turnberry Estates - a thoughtfully designed 55+ adult community offe...	3 beds \| 3 baths \| 1,820 sq.ft.	$645,820	Airbnb cash on cash: -0.84% Traditional cash on cash: 1.7% Airbnb Rental Income: $1991 Traditional Rental Income: $3000 Airbnb ROI: -0.84% Traditional ROI: 1.7%
45 Shelter Hill Avenue Watertown, CT 7 Room 3 bedroom 1.1 bath Colonial, conveniently located in the Oakville section of Watert...	3 beds \| 2 baths \| 1,203 sq.ft.	$250,000	Airbnb cash on cash: 2.91% Traditional cash on cash: 7.68% Airbnb Rental Income: $1991 Traditional Rental Income: $2597 Airbnb ROI: 2.91% Traditional ROI: 7.68%
170 Turnberry Court #33 Watertown, CT Easy Living Begins at Turnberry Estates - a thoughtfully designed 55+ adult community offe...	3 beds \| 2 baths \| 1,688 sq.ft.	$594,513	Airbnb cash on cash: -0.64% Traditional cash on cash: 1.59% Airbnb Rental Income: $1991 Traditional Rental Income: $2707 Airbnb ROI: -0.64% Traditional ROI: 1.59%

Real Estate investment in Watertown, CT

There are 42 properties for sale in the city of Watertown . The median list price in Watertown is $382,318 and the average price per square foot is $204. In November 2026, the average monthly cash on cash return in Watertown is 5.00%. The average monthly rental income in Watertown is $2,942.

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

There are 42 investment properties available for sale in Watertown.

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

The ROI for Long-Term is higher than the Short-Term in Watertown with average rental income of $2,942.

Your search for investment property begins and ends here

Investment Property for Sale in Watertown, CT

104 Northwest Drive

Watertown, CT

4 beds | 3 baths | 2,880 sq.ft.

$615,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.07%

Airbnb Rental Income: $null

Traditional Rental Income: $4421

Airbnb ROI: N/A

Traditional ROI: 5.07%

368 Hamilton Avenue

Watertown, CT

3 beds | 2 baths | 1,238 sq.ft.

$365,000

Airbnb cash on cash: 1.54%

Traditional cash on cash: 5.05%

Airbnb Rental Income: $1991

Traditional Rental Income: $2673

Airbnb ROI: 1.54%

Traditional ROI: 5.05%

56 Orient Street

Watertown, CT

4 beds | 2 baths | 996 sq.ft.

$379,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.98%

Airbnb Rental Income: $null

Traditional Rental Income: $2689

Airbnb ROI: N/A

Traditional ROI: 4.98%

21 Lancaster Street

Watertown, CT

3 beds | 2 baths | 1,484 sq.ft.

$365,000

Airbnb cash on cash: 1.34%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $1991

Traditional Rental Income: $2125

Airbnb ROI: 1.34%

Traditional ROI: 3.25%

555 Davis Street

Watertown, CT

3 beds | 3 baths | 3,893 sq.ft.

$800,000

Airbnb cash on cash: -0.61%

Traditional cash on cash: 2.66%

Airbnb Rental Income: $1991

Traditional Rental Income: $3904

Airbnb ROI: -0.61%

Traditional ROI: 2.66%

6 Burnham Street

Watertown, CT

3 beds | 2 baths | 1,498 sq.ft.

$375,000

Airbnb cash on cash: 1.42%

Traditional cash on cash: 5.33%

Airbnb Rental Income: $1991

Traditional Rental Income: $2845

Airbnb ROI: 1.42%

Traditional ROI: 5.33%

4 Bayview Circle

Watertown, CT

3 beds | 2 baths | 1,688 sq.ft.

$514,900

Airbnb cash on cash: 0.18%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $1991

Traditional Rental Income: $2957

Airbnb ROI: 0.18%

Traditional ROI: 3.27%

96 Neill Drive

Watertown, CT

5 beds | 4 baths | 4,400 sq.ft.

$599,900

Airbnb cash on cash: 2.06%

Traditional cash on cash: 8.45%

Airbnb Rental Income: $3643

Traditional Rental Income: $6425

Airbnb ROI: 2.06%