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
40 Richmondville Ave Westport, CT Charming vintage cape located walking distance to town. 1st floor features living room wit...	6 beds \| 5 baths \| 3,700 sq.ft.	$2,395,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.47% Airbnb Rental Income: $null Traditional Rental Income: $8265 Airbnb ROI: N/A Traditional ROI: 2.47%
5 Lehn Farm Rd Westport, CT Come in and relax in this renovated gem, rebuilt in 2015! Rooms with a purpose yet open an...	3 beds \| 2 baths \| 1,352 sq.ft.	$1,299,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.21% Airbnb Rental Income: $null Traditional Rental Income: $3585 Airbnb ROI: N/A Traditional ROI: 1.21%
34 Woodside Avenue Westport, CT Steeped in history yet thoughtfully reimagined for modern living, this expanded and recent...	4 beds \| 5 baths \| 3,600 sq.ft.	$2,699,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.83% Airbnb Rental Income: $null Traditional Rental Income: $8600 Airbnb ROI: N/A Traditional ROI: 1.83%
159 Easton Rd Westport, CT Let this wonderful home become your familyâs next chapter! Nestled on 2 lush acres to in...	6 beds \| 6 baths \| 8,356 sq.ft.	$4,450,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.15% Airbnb Rental Income: $null Traditional Rental Income: $10139 Airbnb ROI: N/A Traditional ROI: 1.15%
53 Clinton Ave Westport, CT Built in 2005 by local property specialist- Able Construction, this East Coast traditional...	5 beds \| 5 baths \| 7,055 sq.ft.	$2,650,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.22% Airbnb Rental Income: $null Traditional Rental Income: $10789 Airbnb ROI: N/A Traditional ROI: 1.22%
279 Saugatuck Ave Westport, CT Spectacular direct waterfront estate offering unobstructed views of Long Island Sound. Mar...	5 beds \| 6 baths \| 9,546 sq.ft.	$14,900,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.48% Airbnb Rental Income: $null Traditional Rental Income: $9131 Airbnb ROI: N/A Traditional ROI: -2.48%
41 Richmondville Avenue #Duplex 1 Westport, CT A new opportunity to own in The Mill, now completely sold out, this is the first resale op...	2 beds \| 2 baths \| 1,450 sq.ft.	$1,999,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.68% Airbnb Rental Income: $null Traditional Rental Income: $3852 Airbnb ROI: N/A Traditional ROI: -0.68%
3 Keller Ln Westport, CT Cul de sac charmer! This sun-filled home has been loved by the same family for over 50 yea...	2 beds \| 1 baths \| 792 sq.ft.	$798,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.92% Airbnb Rental Income: $null Traditional Rental Income: $3151 Airbnb ROI: N/A Traditional ROI: 0.92%
24 Edgemarth Hill Rd Westport, CT Construction is underway atop this quiet cul de sac in coveted Greens Farms, Westport. 24 ...	6 beds \| 8 baths \| 8,417 sq.ft.	$6,995,826	Airbnb cash on cash: N/A Traditional cash on cash: -1.96% Airbnb Rental Income: $null Traditional Rental Income: $7767 Airbnb ROI: N/A Traditional ROI: -1.96%
36 E Main St Westport, CT In Town location. Convenient to Winslow Park, fabulous shopping and marvelous restaurants....	6 beds \| 6 baths \| 4,922 sq.ft.	$2,999,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.26% Airbnb Rental Income: $null Traditional Rental Income: $2518 Airbnb ROI: N/A Traditional ROI: -2.26%
61 Clapboard Hill Road Westport, CT Located in prestigious Greens Farms, this European-inspired Colonial offers a rare opportu...	4 beds \| 4 baths \| 3,418 sq.ft.	$3,795,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.1% Airbnb Rental Income: $null Traditional Rental Income: $9631 Airbnb ROI: N/A Traditional ROI: 1.1%
238 Hillspoint Rd Westport, CT Experience the pinnacle of waterfront living with this unique opportunity to custom design...	3 beds \| 3 baths \| 2,440 sq.ft.	$4,995,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.7% Airbnb Rental Income: $null Traditional Rental Income: $2123 Airbnb ROI: N/A Traditional ROI: -2.7%
3 Laurel Ln Westport, CT Welcome to this new construction project which is currently underway, with an expected com...	4 beds \| 5 baths \| 4,204 sq.ft.	$3,685,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.18% Airbnb Rental Income: $null Traditional Rental Income: $8220 Airbnb ROI: N/A Traditional ROI: 1.18%
6 Janson Dr Westport, CT PRESENT OFFERS BY NOON MONDAY, 8/4. Nestled on a quiet cul-de-sac just minutes from town, ...	6 beds \| 6 baths \| 7,499 sq.ft.	$4,250,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.98% Airbnb Rental Income: $null Traditional Rental Income: $4656 Airbnb ROI: N/A Traditional ROI: -1.98%
11 Beachside Cmn Westport, CT A true Westport icon, 11 Beachside Common is one of the most architecturally distinctive h...	8 beds \| 8 baths \| 12,946 sq.ft.	$22,825,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.61% Airbnb Rental Income: $null Traditional Rental Income: $11260 Airbnb ROI: N/A Traditional ROI: -2.61%
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: N/A Traditional cash on cash: 0.66% Airbnb Rental Income: $null Traditional Rental Income: $8502 Airbnb ROI: N/A Traditional ROI: 0.66%
56 Charcoal Hill Rd Westport, CT A rare offering, this remarkable Frazier Peters stone home is a masterful blend of histori...	5 beds \| 3 baths \| 3,072 sq.ft.	$2,790,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.04% Airbnb Rental Income: $null Traditional Rental Income: $5510 Airbnb ROI: N/A Traditional ROI: -1.04%
7 High Gate Rd Westport, CT A Greens Farms Opportunity with Character and Possibility Set in the heart of sought-after...	4 beds \| 3 baths \| 2,604 sq.ft.	$1,625,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.68% Airbnb Rental Income: $null Traditional Rental Income: $3809 Airbnb ROI: N/A Traditional ROI: -0.68%
1 Coastal Ct Westport, CT Introducing 1 Coastal Court, a rare opportunity to own in Westport's only gated community,...	5 beds \| 5 baths \| 5,550 sq.ft.	$4,995,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.95% Airbnb Rental Income: $null Traditional Rental Income: $10209 Airbnb ROI: N/A Traditional ROI: -0.95%
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: N/A Traditional cash on cash: 2.88% Airbnb Rental Income: $null Traditional Rental Income: $4547 Airbnb ROI: N/A Traditional ROI: 2.88%
25 Old Rd Westport, CT Set in Westport's sought-after Hunt Club neighborhood, this European-inspired Colonial off...	5 beds \| 4 baths \| 6,330 sq.ft.	$2,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.55% Airbnb Rental Income: $null Traditional Rental Income: $8552 Airbnb ROI: N/A Traditional ROI: 2.55%
25 Hermit Ln Westport, CT 25 Hermit Ln, Westport, CT 06880 \| Single Family Residential	6 beds \| 5 baths \| 9,454 sq.ft.	$2,795,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.06% Airbnb Rental Income: $null Traditional Rental Income: $8364 Airbnb ROI: N/A Traditional ROI: 0.06%
14 Owenoke Park Westport, CT 14 Owenoke Park, Westport, CT 06880 \| Single Family Residential	5 beds \| 5 baths \| 6,050 sq.ft.	$11,995,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.49% Airbnb Rental Income: $null Traditional Rental Income: $7345 Airbnb ROI: N/A Traditional ROI: -2.49%
2 Charcoal Lane Westport, CT Exceptional privacy meets modern luxury on over 2 secluded acres at the end of a quiet cul...	3 beds \| 3 baths \| 3,810 sq.ft.	$2,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.72% Airbnb Rental Income: $null Traditional Rental Income: $4557 Airbnb ROI: N/A Traditional ROI: 0.72%
11 Dogwood Ln Westport, CT 11 Dogwood Ln, Westport, CT 06880 \| Single Family Residential	6 beds \| 6 baths \| 9,100 sq.ft.	$10,650,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.24% Airbnb Rental Income: $null Traditional Rental Income: $8953 Airbnb ROI: N/A Traditional ROI: -2.24%
15 Gorham Ave Westport, CT 15 Gorham Ave, Westport, CT 06880 \| Other	N/A beds \| N/A baths \| N/A	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.04% Airbnb Rental Income: $null Traditional Rental Income: $1357 Airbnb ROI: N/A Traditional ROI: -2.04%
10 Mary Jane Ln Westport, CT 10 Mary Jane Ln, Westport, CT 06880 \| Single Family Residential	6 beds \| 6 baths \| 6,900 sq.ft.	$5,990,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.55% Airbnb Rental Income: $null Traditional Rental Income: $8953 Airbnb ROI: N/A Traditional ROI: -1.55%
55 Center Street Westport, CT Located in Westport's coveted Greens Farms neighborhood, this light-filled home is perfect...	5 beds \| 5 baths \| 4,922 sq.ft.	$2,850,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.52% Airbnb Rental Income: $null Traditional Rental Income: $8597 Airbnb ROI: N/A Traditional ROI: 1.52%
104 Harvest Commons #104 Westport, CT Beautifully updated with main level primary suite and abundant additional living space for...	2 beds \| 3 baths \| 2,161 sq.ft.	$1,449,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.01% Airbnb Rental Income: $null Traditional Rental Income: $3670 Airbnb ROI: N/A Traditional ROI: 1.01%
119 Kings Hwy N Westport, CT Build your dream house on this beautiful property close to town in the Old Hill section of...	2 beds \| 2 baths \| 1,400 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.16% Airbnb Rental Income: $null Traditional Rental Income: $3128 Airbnb ROI: N/A Traditional ROI: 1.16%
24 Blue Ribbon Drive Westport, CT PLEASE SUBMIT ALL OFFERS BY TUESDAY MAY 5TH AT NOON Classic charm meets modern comfort...	4 beds \| 4 baths \| 3,584 sq.ft.	$2,349,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.63% Airbnb Rental Income: $null Traditional Rental Income: $7071 Airbnb ROI: N/A Traditional ROI: 1.63%
21 Covlee Dr Westport, CT 21 Covlee Dr, Westport, CT 06880 \| Single Family Residential	4 beds \| 4 baths \| 4,444 sq.ft.	$6,375,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.14% Airbnb Rental Income: $null Traditional Rental Income: $5992 Airbnb ROI: N/A Traditional ROI: -2.14%
11 Wake Robin Rd Westport, CT Just completed and ready for immediate occupancy, this beautifully crafted new constructio...	5 beds \| 5 baths \| 7,583 sq.ft.	$4,799,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.85% Airbnb Rental Income: $null Traditional Rental Income: $10236 Airbnb ROI: N/A Traditional ROI: -0.85%
4 Charcoal Ln Westport, CT A rare offering indeed! Welcome to 4 Charcoal Lane, an unrivaled multi-generational estate...	5 beds \| 4 baths \| 6,015 sq.ft.	$3,450,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.09% Airbnb Rental Income: $null Traditional Rental Income: $8932 Airbnb ROI: N/A Traditional ROI: 1.09%
32 Whitney Glen #32 Westport, CT Whitney Glen, one of Westport's sought-after communities, is surrounded by mature trees & ...	1 beds \| 2 baths \| 949 sq.ft.	$459,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.76% Airbnb Rental Income: $null Traditional Rental Income: $2566 Airbnb ROI: N/A Traditional ROI: 3.76%
4 Cardinal Lane Westport, CT Welcome to 4 Cardinal Lane ~ a beautifully expanded and thoughtfully updated home set on t...	4 beds \| 4 baths \| 4,651 sq.ft.	$2,199,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.55% Airbnb Rental Income: $null Traditional Rental Income: $6769 Airbnb ROI: N/A Traditional ROI: 1.55%
10 Grist Mill Lane Westport, CT Welcome to 10 Grist Mill Lane, a move-in ready home set on a beautiful, level acre at the ...	3 beds \| 3 baths \| 2,138 sq.ft.	$1,689,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.12% Airbnb Rental Income: $null Traditional Rental Income: $4350 Airbnb ROI: N/A Traditional ROI: 1.12%
20 Cross Street #7 Westport, CT This beautiful condo/townhouse is located conveniently within a 5 min walk to downtown Wes...	2 beds \| 2 baths \| 1,182 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.76% Airbnb Rental Income: $null Traditional Rental Income: $2949 Airbnb ROI: N/A Traditional ROI: 1.76%
22 Dawn Dr Westport, CT Come walk this stunning 1.5 acre lot with me - totally private, tucked at the end of a cul...	4 beds \| 4 baths \| 4,000 sq.ft.	$4,995,700	Airbnb cash on cash: N/A Traditional cash on cash: 0.6% Airbnb Rental Income: $null Traditional Rental Income: $8412 Airbnb ROI: N/A Traditional ROI: 0.6%

Real Estate investment in Westport, CT

There are 76 properties for sale in the city of Westport . The median list price in Westport is $2,223,669 and the average price per square foot is $421. In August 2026, the average monthly cash on cash return in Westport is N/A%. The average monthly rental income in Westport is $4,682.

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

There are 76 investment properties available for sale in Westport.

The ROI for Short-Term is higher than the Long-Term in Westport with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Westport, CT

40 Richmondville Ave

Westport, CT

6 beds | 5 baths | 3,700 sq.ft.

$2,395,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.47%

Airbnb Rental Income: $null

Traditional Rental Income: $8265

Airbnb ROI: N/A

Traditional ROI: 2.47%

5 Lehn Farm Rd

Westport, CT

3 beds | 2 baths | 1,352 sq.ft.

$1,299,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.21%

Airbnb Rental Income: $null

Traditional Rental Income: $3585

Airbnb ROI: N/A

Traditional ROI: 1.21%

34 Woodside Avenue

Westport, CT

4 beds | 5 baths | 3,600 sq.ft.

$2,699,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.83%

Airbnb Rental Income: $null

Traditional Rental Income: $8600

Airbnb ROI: N/A

Traditional ROI: 1.83%

159 Easton Rd

Westport, CT

6 beds | 6 baths | 8,356 sq.ft.

$4,450,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.15%

Airbnb Rental Income: $null

Traditional Rental Income: $10139

Airbnb ROI: N/A

Traditional ROI: 1.15%

53 Clinton Ave

Westport, CT

5 beds | 5 baths | 7,055 sq.ft.

$2,650,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.22%

Airbnb Rental Income: $null

Traditional Rental Income: $10789

Airbnb ROI: N/A

Traditional ROI: 1.22%

279 Saugatuck Ave

Westport, CT

5 beds | 6 baths | 9,546 sq.ft.

$14,900,000

Airbnb cash on cash: N/A

Traditional cash on cash: -2.48%

Airbnb Rental Income: $null

Traditional Rental Income: $9131

Airbnb ROI: N/A

Traditional ROI: -2.48%

41 Richmondville Avenue #Duplex 1

Westport, CT

2 beds | 2 baths | 1,450 sq.ft.

$1,999,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.68%

Airbnb Rental Income: $null

Traditional Rental Income: $3852

Airbnb ROI: N/A

Traditional ROI: -0.68%

3 Keller Ln

Westport, CT

2 beds | 1 baths | 792 sq.ft.

$798,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.92%

Airbnb Rental Income: $null

Traditional Rental Income: $3151

Airbnb ROI: N/A