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
41 Richmondville Avenue #303 Westport, CT Showing daily by appointment. IMMEDIATE OCCUPANCY! Only 2 homes remain!! A third floor 1...	2 beds \| 2 baths \| 1,300 sq.ft.	$1,825,000	Airbnb cash on cash: -2.24% Traditional cash on cash: 0.3% Airbnb Rental Income: $2098 Traditional Rental Income: $5861 Airbnb ROI: -2.24% Traditional ROI: 0.3%
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%
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.	$950,000	Airbnb cash on cash: -1.79% Traditional cash on cash: 3.46% Airbnb Rental Income: $1762 Traditional Rental Income: $5916 Airbnb ROI: -1.79% Traditional ROI: 3.46%
61 Clapboard Hill Road Westport, CT Located in prestigious Greens Farms, this European-inspired Colonial captures the timeless...	4 beds \| 5 baths \| 3,500 sq.ft.	$3,899,000	Airbnb cash on cash: -2.49% Traditional cash on cash: -0.49% Airbnb Rental Income: $3149 Traditional Rental Income: $9631 Airbnb ROI: -2.49% 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 IMMEDIATE OCCUPANCY! Only TWO homes remain at The Mill Westport! This impressive home ha...	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.	$3,485,000	Airbnb cash on cash: -2.77% Traditional cash on cash: -0.26% Airbnb Rental Income: $1762 Traditional Rental Income: $9392 Airbnb ROI: -2.77% Traditional ROI: -0.26%
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 We're back! Can you believe it? So, we're excited to reintroduce this stunning home-nothin...	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 Beachside Common Westport, CT A true Westport icon, 11 Beachside Common is one of the most architecturally distinctive h...	5 beds \| 8 baths \| 14,038 sq.ft.	$5,950,000	Airbnb cash on cash: -2.92% Traditional cash on cash: -1.11% Airbnb Rental Income: $1762 Traditional Rental Income: $11260 Airbnb ROI: -2.92% Traditional ROI: -1.11%
4 Pin Oak Court Westport, CT Discover the possibilities with this 4-bedroom, 3 1/2 -bath Cape set on a flat and spaciou...	4 beds \| 4 baths \| 2,359 sq.ft.	$899,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 4.31% Airbnb Rental Income: $3149 Traditional Rental Income: $6338 Airbnb ROI: -0.36% Traditional ROI: 4.31%
18 Sherwood Drive Westport, CT This Nantucket-style turnkey retreat has been reimagined and extensively renovated to crea...	4 beds \| 2 baths \| 2,158 sq.ft.	$2,195,000	Airbnb cash on cash: -1.98% Traditional cash on cash: -1.15% Airbnb Rental Income: $3149 Traditional Rental Income: $4122 Airbnb ROI: -1.98% Traditional ROI: -1.15%
230 Saugatuck Avenue #U-6 Westport, CT Welcome to Indian River Green! Located in a private community of 20 Townhouse Style Units ...	2 beds \| 3 baths \| 1,200 sq.ft.	$734,900	Airbnb cash on cash: -1.99% Traditional cash on cash: 0.6% Airbnb Rental Income: $2098 Traditional Rental Income: $3335 Airbnb ROI: -1.99% Traditional ROI: 0.6%
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%
56 Charcoal Hill Road 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.	$2,495,000	Airbnb cash on cash: -2.62% Traditional cash on cash: -0.79% Airbnb Rental Income: $1762 Traditional Rental Income: $5510 Airbnb ROI: -2.62% Traditional ROI: -0.79%
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%
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%
4 Highland Road Westport, CT Be Home for the Holidays! Welcome to your timeless Colonial in sought-after Coleytown, whe...	4 beds \| 3 baths \| 2,556 sq.ft.	$1,495,000	Airbnb cash on cash: -1.44% Traditional cash on cash: 0.45% Airbnb Rental Income: $3149 Traditional Rental Income: $5070 Airbnb ROI: -1.44% Traditional ROI: 0.45%
118 Roseville Road Westport, CT A sexy modernist concrete retreat designed by Frank Lloyd Wright protege Francis Barry Byr...	3 beds \| 3 baths \| 4,243 sq.ft.	$3,100,000	Airbnb cash on cash: -1.79% Traditional cash on cash: -1.69% Airbnb Rental Income: $4985 Traditional Rental Income: $4228 Airbnb ROI: -1.79% Traditional ROI: -1.69%
22 Burritts Landing South Westport, CT Live the dream in this 4,800+ sq. ft. 5BR, 5BA home on 1 acre in one of Westport's most de...	5 beds \| 5 baths \| 4,740 sq.ft.	$3,590,000	Airbnb cash on cash: -2.86% Traditional cash on cash: -0.51% Airbnb Rental Income: $1762 Traditional Rental Income: $9102 Airbnb ROI: -2.86% Traditional ROI: -0.51%
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%
24 Tupelo Road Westport, CT Nestled on a quiet cul-de-sac, this private oasis is truly move-in ready! Set on over an a...	4 beds \| 3 baths \| 3,705 sq.ft.	$1,595,000	Airbnb cash on cash: -1.55% Traditional cash on cash: 0.79% Airbnb Rental Income: $3149 Traditional Rental Income: $5896 Airbnb ROI: -1.55% Traditional ROI: 0.79%
6 Sunny Acres Lane Westport, CT Welcome to "The Village" as this lovely neighborhood in Westport is known by long time hom...	4 beds \| 1 baths \| 1,196 sq.ft.	$700,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 1.69% Airbnb Rental Income: $3149 Traditional Rental Income: $3235 Airbnb ROI: 0.46% Traditional ROI: 1.69%
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%
2 Drumlin Road Westport, CT Welcome to 2 Drumlin Road, a rare single-story ranch nestled in the desirable Compo Beach ...	4 beds \| 2 baths \| 1,610 sq.ft.	$899,000	Airbnb cash on cash: -0.34% Traditional cash on cash: 1.82% Airbnb Rental Income: $3149 Traditional Rental Income: $4243 Airbnb ROI: -0.34% Traditional ROI: 1.82%
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.	$2,850,000	Airbnb cash on cash: -2.25% Traditional cash on cash: 0.21% Airbnb Rental Income: $3149 Traditional Rental Income: $8922 Airbnb ROI: -2.25% Traditional ROI: 0.21%

Real Estate investment in Westport, CT

There are 35 properties for sale in the city of Westport . The median list price in Westport is $2,495,000 and the average price per square foot is $656. In November 2025, the average monthly cash on cash return in Westport is N/A%. The average monthly rental income in Westport is $5,896.

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

There are 35 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 $5,896.

Your search for investment property begins and ends here

Investment Property for Sale in Westport, CT

41 Richmondville Avenue #303

Westport, CT

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

$1,825,000

Airbnb cash on cash: -2.24%

Traditional cash on cash: 0.3%

Airbnb Rental Income: $2098

Traditional Rental Income: $5861

Airbnb ROI: -2.24%

Traditional ROI: 0.3%

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%

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.

$950,000

Airbnb cash on cash: -1.79%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $1762

Traditional Rental Income: $5916

Airbnb ROI: -1.79%

Traditional ROI: 3.46%

61 Clapboard Hill Road

Westport, CT

4 beds | 5 baths | 3,500 sq.ft.

$3,899,000

Airbnb cash on cash: -2.49%

Traditional cash on cash: -0.49%

Airbnb Rental Income: $3149

Traditional Rental Income: $9631

Airbnb ROI: -2.49%

Traditional ROI: -0.49%

3 Laurel Lane

Westport, CT

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

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%