Real Estate Investment Properties for Sale in Westport, CT

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
32 Edgewater Hillside Westport, CT A breathtaking waterfront retreat where architecture, craftsmanship, and setting unite in ...	3 beds \| 4 baths \| 3,236 sq.ft.	$4,495,000	Airbnb cash on cash: -0.69% Traditional cash on cash: -0.14% Airbnb Rental Income: $4985 Traditional Rental Income: $6255 Airbnb ROI: -0.69% Traditional ROI: -0.14%
41 Richmondville Avenue #303 Westport, CT IMMEDIATE OCCUPANCY! Only 5 homes remain!! A third floor 1 bed+den with 2-baths at The Mil...	2 beds \| 2 baths \| 1,300 sq.ft.	$1,749,000	Airbnb cash on cash: -2.29% Traditional cash on cash: 0.36% Airbnb Rental Income: $2098 Traditional Rental Income: $5861 Airbnb ROI: -2.29% Traditional ROI: 0.36%
60 Wilton Road #2C Westport, CT Fully completed and ready for occupancy. Unit 2C is the ONLY 4 BEDROOM unit in the buildin...	4 beds \| 4 baths \| 3,460 sq.ft.	$3,699,000	Airbnb cash on cash: -2.45% Traditional cash on cash: -0.28% Airbnb Rental Income: $3149 Traditional Rental Income: $9885 Airbnb ROI: -2.45% Traditional ROI: -0.28%
260 Hillspoint Road Westport, CT Experience the unparalleled luxury of this exquisite Compo Beach seaside home,a masterpiec...	5 beds \| 8 baths \| 10,800 sq.ft.	$10,800,000	Airbnb cash on cash: -3.02% Traditional cash on cash: -2.35% Airbnb Rental Income: $1762 Traditional Rental Income: $7920 Airbnb ROI: -3.02% Traditional ROI: -2.35%
87 Red Coat Road Westport, CT MOST UNIQUE HOUSE IN WESTPORT LARGE LOG HOME ON THE RIVER THAT IS STOCKED WITH TROUT. INGR...	4 beds \| 4 baths \| 4,636 sq.ft.	$4,600,000	Airbnb cash on cash: -2.58% Traditional cash on cash: -1.38% Airbnb Rental Income: $3149 Traditional Rental Income: $7553 Airbnb ROI: -2.58% Traditional ROI: -1.38%
61 Edgewater Commons Lane Westport, CT WALK TO BEACH * WATER VIEWS * ROOM FOR A POOL This coastal gem sits on one of the largest ...	4 beds \| 4 baths \| 3,397 sq.ft.	$1,779,000	Airbnb cash on cash: -1.71% Traditional cash on cash: 1% Airbnb Rental Income: $3149 Traditional Rental Income: $6921 Airbnb ROI: -1.71% Traditional ROI: 1%
489 Main Street Westport, CT Single Family with legal accessory apartment. New 5 bedroom septic system- just installed ...	5 beds \| 4 baths \| 2,192 sq.ft.	$900,000	Airbnb cash on cash: -1.71% Traditional cash on cash: 3.82% Airbnb Rental Income: $1762 Traditional Rental Income: $5916 Airbnb ROI: -1.71% Traditional ROI: 3.82%
61 Clapboard Hill Road Westport, CT Located in prestigious Greens Farms, this European-inspired Colonial captures the timeless...	4 beds \| 4 baths \| 3,418 sq.ft.	$3,895,000	Airbnb cash on cash: -2.48% Traditional cash on cash: -0.49% Airbnb Rental Income: $3149 Traditional Rental Income: $9631 Airbnb ROI: -2.48% Traditional ROI: -0.49%
3 Laurel Lane Westport, CT Discover the epitome of elegance and sophistication on a quiet street, in a coveted area i...	4 beds \| 5 baths \| 4,204 sq.ft.	$3,785,000	Airbnb cash on cash: -2.47% Traditional cash on cash: -0.82% Airbnb Rental Income: $3149 Traditional Rental Income: $8220 Airbnb ROI: -2.47% Traditional ROI: -0.82%
41 Richmondville Avenue #Duplex 2 Westport, CT This impressive home has floor-to-ceiling windows, wood floors and a linear gas fireplace....	2 beds \| 3 baths \| 1,760 sq.ft.	$2,495,000	Airbnb cash on cash: -2.56% Traditional cash on cash: -1.4% Airbnb Rental Income: $2098 Traditional Rental Income: $4232 Airbnb ROI: -2.56% Traditional ROI: -1.4%
16 Burr School Road Westport, CT A masterful full renovation by acclaimed Coastal Luxury Homes, this extraordinary modern r...	5 beds \| 5 baths \| 5,056 sq.ft.	$3,395,000	Airbnb cash on cash: -2.76% Traditional cash on cash: -0.18% Airbnb Rental Income: $1762 Traditional Rental Income: $9392 Airbnb ROI: -2.76% Traditional ROI: -0.18%
10 Twin Falls Lane Westport, CT Beyond Beautiful - Welcome to 10 Twin Falls Lane, a striking property and home filled with...	4 beds \| 3 baths \| 4,231 sq.ft.	$2,249,000	Airbnb cash on cash: -2.01% Traditional cash on cash: -0.44% Airbnb Rental Income: $3149 Traditional Rental Income: $5716 Airbnb ROI: -2.01% Traditional ROI: -0.44%
26 Hitchcock Road Westport, CT Welcome to Brookside, the amazing new project by GreenDay and Co. Get ready to be captivat...	5 beds \| 5 baths \| 4,549 sq.ft.	$2,639,000	Airbnb cash on cash: -2.65% Traditional cash on cash: 0.45% Airbnb Rental Income: $1762 Traditional Rental Income: $8858 Airbnb ROI: -2.65% Traditional ROI: 0.45%
11 Old Hill Road Westport, CT Nestled in the heart of Westport's coveted Old Hill neighborhood, this home offers the cha...	4 beds \| 5 baths \| 3,935 sq.ft.	$2,527,000	Airbnb cash on cash: -2.13% Traditional cash on cash: 0.86% Airbnb Rental Income: $3149 Traditional Rental Income: $9457 Airbnb ROI: -2.13% Traditional ROI: 0.86%
11 Edgewater Hillside Westport, CT COMPO BEACH WATER VIEWS at this picture-perfect beach house. Edgewater Hillside is the bes...	4 beds \| 5 baths \| 4,693 sq.ft.	$3,899,000	Airbnb cash on cash: -2.49% Traditional cash on cash: -0.81% Airbnb Rental Income: $3149 Traditional Rental Income: $8502 Airbnb ROI: -2.49% Traditional ROI: -0.81%
17 Clover Lane Westport, CT SOPHISTICATED CONTEMPORARY RETREAT - CLOVER LANE Exciting opportunity to own a beautifully...	5 beds \| 4 baths \| 3,000 sq.ft.	$2,195,000	Airbnb cash on cash: -2.55% Traditional cash on cash: 0.18% Airbnb Rental Income: $1762 Traditional Rental Income: $6847 Airbnb ROI: -2.55% Traditional ROI: 0.18%
7 High Gate Road Westport, CT A Greens Farms Opportunity with Character and Possibility Set in the heart of sought-after...	4 beds \| 2 baths \| 1,704 sq.ft.	$899,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 1.31% Airbnb Rental Income: $3149 Traditional Rental Income: $3809 Airbnb ROI: -0.33% Traditional ROI: 1.31%
111 Sturges Highway Westport, CT Welcome to 111 Sturges Highway, the pinnacle of refined elegance and timeless design. A ci...	5 beds \| 8 baths \| 7,359 sq.ft.	$3,550,000	Airbnb cash on cash: -2.77% Traditional cash on cash: -0.01% Airbnb Rental Income: $1762 Traditional Rental Income: $10388 Airbnb ROI: -2.77% Traditional ROI: -0.01%
195 Hillspoint Road Westport, CT This pristine 3-bedroom, 2.5-bath waterfront home offers the ultimate coastal lifestyle wi...	3 beds \| 3 baths \| 2,549 sq.ft.	$2,499,000	Airbnb cash on cash: -1.46% Traditional cash on cash: -1.23% Airbnb Rental Income: $4985 Traditional Rental Income: $4508 Airbnb ROI: -1.46% Traditional ROI: -1.23%
1 Coastal Court Westport, CT Introducing 1 Coastal Court, a rare opportunity to own in Westport's only gated community,...	5 beds \| 7 baths \| 5,550 sq.ft.	$4,995,000	Airbnb cash on cash: -2.88% Traditional cash on cash: -0.95% Airbnb Rental Income: $1762 Traditional Rental Income: $10209 Airbnb ROI: -2.88% Traditional ROI: -0.95%
8 Canal Road Westport, CT Incredible opportunity to own a coastal retreat with sweeping water views of Saugatuck Har...	2 beds \| 3 baths \| 1,787 sq.ft.	$1,395,000	Airbnb cash on cash: -2% Traditional cash on cash: -0.06% Airbnb Rental Income: $2098 Traditional Rental Income: $4072 Airbnb ROI: -2% Traditional ROI: -0.06%
5 Minard Drive Westport, CT Set in the coveted Saugatuck Shores enclave, this 5BR/4BA Colonial offers timeless design ...	5 beds \| 4 baths \| 2,732 sq.ft.	$2,300,000	Airbnb cash on cash: -2.58% Traditional cash on cash: -0.62% Airbnb Rental Income: $1762 Traditional Rental Income: $5451 Airbnb ROI: -2.58% Traditional ROI: -0.62%
40 Maple Avenue North Westport, CT Prime location a few houses down from the Hunt Club three bedrooms with two additional bou...	3 beds \| 2 baths \| 3,171 sq.ft.	$1,699,900	Airbnb cash on cash: -0.68% Traditional cash on cash: -0.6% Airbnb Rental Income: $4985 Traditional Rental Income: $4095 Airbnb ROI: -0.68% Traditional ROI: -0.6%
33 Burnham Hill Westport, CT Beach Living Awaits at 33 Burnham Hill Road, Westport. Build or reimagine the home of your...	4 beds \| 2 baths \| 2,290 sq.ft.	$2,695,000	Airbnb cash on cash: -2.2% Traditional cash on cash: -1.52% Airbnb Rental Income: $3149 Traditional Rental Income: $4130 Airbnb ROI: -2.2% Traditional ROI: -1.52%
23 Bridge Street Westport, CT Nestled back on a .31 Acre site is an intriguing circa 1900 converted barn/carriage house....	4 beds \| 3 baths \| 3,054 sq.ft.	$899,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 2.36% Airbnb Rental Income: $3149 Traditional Rental Income: $4687 Airbnb ROI: -0.33% Traditional ROI: 2.36%
123 Greens Farms Road Westport, CT Classic Greens Farms Colonial - Timeless Elegance Meets Modern Comfort ~ Nestled in one of...	4 beds \| 5 baths \| 5,207 sq.ft.	$2,795,000	Airbnb cash on cash: -2.23% Traditional cash on cash: 0.27% Airbnb Rental Income: $3149 Traditional Rental Income: $8922 Airbnb ROI: -2.23% Traditional ROI: 0.27%
57 Partrick Road Westport, CT SELLERS WILL BE REVIEWING OFFERS ON MONDAY 11/10 AT 12:00 This gracious Colonial in the he...	4 beds \| 3 baths \| 3,337 sq.ft.	$1,500,000	Airbnb cash on cash: -1.45% Traditional cash on cash: 0.86% Airbnb Rental Income: $3149 Traditional Rental Income: $5649 Airbnb ROI: -1.45% Traditional ROI: 0.86%
116 Roseville Road Westport, CT Tucked away on a picturesque property with a peaceful pond and complete privacy, this cust...	5 beds \| 7 baths \| 5,771 sq.ft.	$3,950,000	Airbnb cash on cash: -2.81% Traditional cash on cash: -0.21% Airbnb Rental Income: $1762 Traditional Rental Income: $10788 Airbnb ROI: -2.81% Traditional ROI: -0.21%
41 Richmondville Avenue unit: Duplex 2 #Duplex 2 Westport, CT IMMEDIATE OCCUPANCY! Only TWO homes remain at The Mill Westport! This impressive home has ...	2 beds \| 3 baths \| 1,760 sq.ft.	$2,495,000	Airbnb cash on cash: -1.65% Traditional cash on cash: -0.53% Airbnb Rental Income: $2098 Traditional Rental Income: $4152 Airbnb ROI: -1.65% Traditional ROI: -0.53%
5 Willow Walk Westport, CT SELLER IS REQUESTING HIGHEST AND BEST OFFERS BE SUBMITTED BY SUNDAY, NOVEMBER 23RD AT 8PM....	4 beds \| 3 baths \| 4,237 sq.ft.	$1,899,000	Airbnb cash on cash: -1.8% Traditional cash on cash: -0.13% Airbnb Rental Income: $3149 Traditional Rental Income: $5387 Airbnb ROI: -1.8% Traditional ROI: -0.13%
4 Woods Grove Road Westport, CT HUGE OPPORTUNITY. PROPERTY TO BE SOLD AS-IS, WHERE IS WITH NO REPRESENTATIONS AS TO CONDIT...	4 beds \| 3 baths \| 2,133 sq.ft.	$999,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 1.66% Airbnb Rental Income: $3149 Traditional Rental Income: $4547 Airbnb ROI: -0.61% Traditional ROI: 1.66%
115 Valley Road Westport, CT Set in beautiful Greens Farms, this 3-level split home offers the kind of layout many peop...	3 beds \| 2 baths \| 1,656 sq.ft.	$825,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 1.41% Airbnb Rental Income: $4985 Traditional Rental Income: $3582 Airbnb ROI: 1.91% Traditional ROI: 1.41%

Real Estate investment in Westport, CT

There are 32 properties for sale in the city of Westport . The median list price in Westport is $2,497,000 and the average price per square foot is $676. In December 2025, the average monthly cash on cash return in Westport is N/A%. The average monthly rental income in Westport is $6,086.

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

There are 32 investment properties available for sale in Westport.

In 2025, the best neighborhood to buy investment property is Westport.

The ROI for Long-Term is higher than the Short-Term in Westport with average rental income of $6,086.

Your search for investment property begins and ends here

Investment Property for Sale in Westport, CT

32 Edgewater Hillside

Westport, CT

3 beds | 4 baths | 3,236 sq.ft.

$4,495,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: -0.14%

Airbnb Rental Income: $4985

Traditional Rental Income: $6255

Airbnb ROI: -0.69%

Traditional ROI: -0.14%

41 Richmondville Avenue #303

Westport, CT

2 beds | 2 baths | 1,300 sq.ft.

$1,749,000

Airbnb cash on cash: -2.29%

Traditional cash on cash: 0.36%

Airbnb Rental Income: $2098

Traditional Rental Income: $5861

Airbnb ROI: -2.29%

Traditional ROI: 0.36%

60 Wilton Road #2C

Westport, CT

4 beds | 4 baths | 3,460 sq.ft.

$3,699,000

Airbnb cash on cash: -2.45%

Traditional cash on cash: -0.28%

Airbnb Rental Income: $3149

Traditional Rental Income: $9885

Airbnb ROI: -2.45%

Traditional ROI: -0.28%

260 Hillspoint Road

Westport, CT

5 beds | 8 baths | 10,800 sq.ft.

$10,800,000

Airbnb cash on cash: -3.02%

Traditional cash on cash: -2.35%

Airbnb Rental Income: $1762

Traditional Rental Income: $7920

Airbnb ROI: -3.02%

Traditional ROI: -2.35%

87 Red Coat Road

Westport, CT

4 beds | 4 baths | 4,636 sq.ft.

$4,600,000

Airbnb cash on cash: -2.58%

Traditional cash on cash: -1.38%

Airbnb Rental Income: $3149

Traditional Rental Income: $7553

Airbnb ROI: -2.58%

Traditional ROI: -1.38%

61 Edgewater Commons Lane

Westport, CT

4 beds | 4 baths | 3,397 sq.ft.

$1,779,000

Airbnb cash on cash: -1.71%

Traditional cash on cash: 1%

Airbnb Rental Income: $3149

Traditional Rental Income: $6921

Airbnb ROI: -1.71%

Traditional ROI: 1%

489 Main Street

Westport, CT

5 beds | 4 baths | 2,192 sq.ft.

$900,000

Airbnb cash on cash: -1.71%

Traditional cash on cash: 3.82%

Airbnb Rental Income: $1762

Traditional Rental Income: $5916

Airbnb ROI: -1.71%

Traditional ROI: 3.82%

61 Clapboard Hill Road

Westport, CT

4 beds | 4 baths | 3,418 sq.ft.

$3,895,000

Airbnb cash on cash: -2.48%

Traditional cash on cash: -0.49%

Airbnb Rental Income: $3149

Traditional Rental Income: $9631

Airbnb ROI: -2.48%