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
3 Nassau Road Westport, CT This stunning beach Colonial, built in 2022, masterfully blends comfort and style. Tucked ...	5 beds \| 5 baths \| 3,700 sq.ft.	$3,500,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 0.73% Airbnb Rental Income: $5401 Traditional Rental Income: $6562 Airbnb ROI: 0.04% Traditional ROI: 0.73%
60 Wilton Road #Penthouse 4B Westport, CT Nestled along the Saugatuck River comes a collection of twelve refined, private homes desi...	2 beds \| 3 baths \| 2,437 sq.ft.	$3,650,000	Airbnb cash on cash: -2.4% Traditional cash on cash: -1.67% Airbnb Rental Income: $3311 Traditional Rental Income: $5061 Airbnb ROI: -2.4% Traditional ROI: -1.67%
1 Crestwood Road Westport, CT TO BE BUILT. Home has never been more important. A place that can fit all needs at all tim...	5 beds \| 7 baths \| 5,700 sq.ft.	$2,899,000	Airbnb cash on cash: -1.56% Traditional cash on cash: 1.05% Airbnb Rental Income: $5401 Traditional Rental Income: $11349 Airbnb ROI: -1.56% Traditional ROI: 1.05%
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: -1.09% Traditional cash on cash: -0.28% Airbnb Rental Income: $8730 Traditional Rental Income: $9885 Airbnb ROI: -1.09% Traditional ROI: -0.28%
41 Richmondville Avenue #210 Westport, CT Welcome to this inviting 2-bedroom, 2.5 bathroom corner residence with historic details at...	2 beds \| 3 baths \| 1,630 sq.ft.	$2,195,000	Airbnb cash on cash: -2.81% Traditional cash on cash: -2.23% Airbnb Rental Income: $3311 Traditional Rental Income: $3762 Airbnb ROI: -2.81% Traditional ROI: -2.23%
443 Riverside Avenue Westport, CT 1830 home on Saugatuck River.	3 beds \| 4 baths \| 2,547 sq.ft.	$2,500,000	Airbnb cash on cash: -0.97% Traditional cash on cash: -0.95% Airbnb Rental Income: $6343 Traditional Rental Income: $5160 Airbnb ROI: -0.97% Traditional ROI: -0.95%
50 Compo Mill Cove Westport, CT Enjoy the Holidays at your WATERFRONT PARADISE! Tranquil location offers unrivaled access ...	5 beds \| 7 baths \| 3,955 sq.ft.	$12,250,000	Airbnb cash on cash: -2.78% Traditional cash on cash: -2.46% Airbnb Rental Income: $5401 Traditional Rental Income: $7986 Airbnb ROI: -2.78% Traditional ROI: -2.46%
41 Richmondville Avenue #PH West Westport, CT PH West features 3 beds den and private terrace. The corner living room spans 36+ ft w flo...	3 beds \| 3 baths \| 2,400 sq.ft.	$3,195,000	Airbnb cash on cash: -2.35% Traditional cash on cash: -2.64% Airbnb Rental Income: $6343 Traditional Rental Income: $4250 Airbnb ROI: -2.35% Traditional ROI: -2.64%
6 Pan Handle Lane Westport, CT This Custom Built Adirondack Estate boasts over 10,000 incredible square feet of living sp...	5 beds \| 9 baths \| 10,471 sq.ft.	$4,500,000	Airbnb cash on cash: -2.12% Traditional cash on cash: -1.25% Airbnb Rental Income: $5401 Traditional Rental Income: $7931 Airbnb ROI: -2.12% Traditional ROI: -1.25%
209 Compo Road South Westport, CT PRICE REDUCED!!!! Location, location, location! Walk to the train, Longshore Country Club ...	3 beds \| 1 baths \| 2,067 sq.ft.	$1,099,000	Airbnb cash on cash: 1.77% Traditional cash on cash: -0.45% Airbnb Rental Income: $6343 Traditional Rental Income: $2833 Airbnb ROI: 1.77% Traditional ROI: -0.45%
19 Bermuda Road Westport, CT Discover luxury living on Saugautuck Shores in this stunning contemporary home. Year round...	4 beds \| 6 baths \| 4,560 sq.ft.	$3,875,000	Airbnb cash on cash: -1.19% Traditional cash on cash: -0.36% Airbnb Rental Income: $8730 Traditional Rental Income: $10068 Airbnb ROI: -1.19% Traditional ROI: -0.36%
260 Hillspoint Road Westport, CT Experience the unparalleled luxury of this exquisite Compo Beach seaside home,a masterpiec...	5 beds \| 8 baths \| 8,188 sq.ft.	$13,500,000	Airbnb cash on cash: -2.8% Traditional cash on cash: -2.51% Airbnb Rental Income: $5401 Traditional Rental Income: $7920 Airbnb ROI: -2.8% Traditional ROI: -2.51%
5 Timber Lane Westport, CT Thrilled to present 5 Timber Lane - a stunning custom Colonial situated on 1.6 acres, offe...	5 beds \| 6 baths \| 5,273 sq.ft.	$3,999,000	Airbnb cash on cash: -2% Traditional cash on cash: -1.04% Airbnb Rental Income: $5401 Traditional Rental Income: $7839 Airbnb ROI: -2% Traditional ROI: -1.04%
4 Michele Lane Westport, CT Nestled in the prestigious Coleytown area of Westport, this custom-built Colonial sits on ...	5 beds \| 8 baths \| 9,240 sq.ft.	$3,599,000	Airbnb cash on cash: -1.87% Traditional cash on cash: -0.83% Airbnb Rental Income: $5401 Traditional Rental Income: $7790 Airbnb ROI: -1.87% Traditional ROI: -0.83%
6 Fraser Road Westport, CT Nestled on a quiet cul-de-sac and perfectly situated on two acres, sits this spectacular c...	5 beds \| 4 baths \| 7,420 sq.ft.	$3,695,000	Airbnb cash on cash: -1.9% Traditional cash on cash: -1.61% Airbnb Rental Income: $5401 Traditional Rental Income: $5308 Airbnb ROI: -1.9% Traditional ROI: -1.61%
24 Easton Road Westport, CT Fantastic opportunity to live in the highly sought-after Coleytown neighborhood in Westpor...	5 beds \| 5 baths \| 3,199 sq.ft.	$1,299,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 2.62% Airbnb Rental Income: $5401 Traditional Rental Income: $7038 Airbnb ROI: 0.36% Traditional ROI: 2.62%
38 Rices Lane Westport, CT Renovate or build your dream home on this spectacular one-of-a-kind property in coveted Ol...	5 beds \| 3 baths \| 2,696 sq.ft.	$1,899,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 1.04% Airbnb Rental Income: $5401 Traditional Rental Income: $7439 Airbnb ROI: -0.74% Traditional ROI: 1.04%
163 Cross Highway Westport, CT A Timeless Charmer! Picture yourself in this wonderful Antique Center-Hall Colonial Farmho...	3 beds \| 2 baths \| 2,304 sq.ft.	$1,595,000	Airbnb cash on cash: 0.25% Traditional cash on cash: -0.71% Airbnb Rental Income: $6343 Traditional Rental Income: $3678 Airbnb ROI: 0.25% Traditional ROI: -0.71%
54 Compo Mill Cove Westport, CT Direct waterfront! Discover the magic of one of Fairfield County's most special waterfront...	4 beds \| 5 baths \| 5,606 sq.ft.	$6,499,000	Airbnb cash on cash: -2.01% Traditional cash on cash: -2.08% Airbnb Rental Income: $8730 Traditional Rental Income: $6657 Airbnb ROI: -2.01% Traditional ROI: -2.08%
19 Long Lots Road Westport, CT $25,000 PRICE REDUCTION. Welcome to this beautifully remodeled center hall Colonial, ...	4 beds \| 4 baths \| 4,279 sq.ft.	$2,274,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 0.14% Airbnb Rental Income: $8730 Traditional Rental Income: $7001 Airbnb ROI: 0.18% Traditional ROI: 0.14%
12 Strathmore Lane #12 Westport, CT Welcome to this charming 1,519 square foot townhouse (End Unit) in the lovely Strathmore L...	2 beds \| 3 baths \| 1,519 sq.ft.	$579,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 1.89% Airbnb Rental Income: $3311 Traditional Rental Income: $3352 Airbnb ROI: 0.44% Traditional ROI: 1.89%
11 Marilane Westport, CT Experience a world of refined sophistication and casual elegance in this newly built home ...	5 beds \| 5 baths \| 8,118 sq.ft.	$3,400,000	Airbnb cash on cash: -1.79% Traditional cash on cash: -0.46% Airbnb Rental Income: $5401 Traditional Rental Income: $8514 Airbnb ROI: -1.79% Traditional ROI: -0.46%
12 Iron Gate Hill Westport, CT This remarkable Normandy manor is located in a private enclave of serene rolling lawns, gu...	5 beds \| 4 baths \| 4,667 sq.ft.	$2,500,000	Airbnb cash on cash: -1.31% Traditional cash on cash: -0.73% Airbnb Rental Income: $5401 Traditional Rental Income: $5674 Airbnb ROI: -1.31% Traditional ROI: -0.73%
88 Kings Highway South Westport, CT In the middle of the coveted Saugatuck neighborhood and among the notable homes in Westpor...	4 beds \| 4 baths \| 3,482 sq.ft.	$1,850,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 0.69% Airbnb Rental Income: $8730 Traditional Rental Income: $6656 Airbnb ROI: 0.94% Traditional ROI: 0.69%
1 Sturges Highway Westport, CT Timeless Colonial Estate: This exquisite five-bedroom, four full and two half-bath Colonia...	5 beds \| 6 baths \| 5,790 sq.ft.	$4,995,000	Airbnb cash on cash: -2.22% Traditional cash on cash: -1.4% Airbnb Rental Income: $5401 Traditional Rental Income: $8132 Airbnb ROI: -2.22% Traditional ROI: -1.4%
3 Viking Green Westport, CT As the sun dipped below the horizon, casting a warm glow over Red Coat, the For Sale sign ...	4 beds \| 4 baths \| 2,658 sq.ft.	$1,196,000	Airbnb cash on cash: 3.16% Traditional cash on cash: 2.47% Airbnb Rental Income: $8730 Traditional Rental Income: $6324 Airbnb ROI: 3.16% Traditional ROI: 2.47%
15 Sunrise Road Westport, CT Nearly complete 2024 roomy 5-7 bedroom farmhouse in desirable 'walk-to-everything' hip Sau...	5 beds \| 7 baths \| 5,407 sq.ft.	$2,975,000	Airbnb cash on cash: -1.6% Traditional cash on cash: -0.35% Airbnb Rental Income: $5401 Traditional Rental Income: $7769 Airbnb ROI: -1.6% Traditional ROI: -0.35%
36 Terra Nova Circle #36 Westport, CT Welcome home to this elegant and exquisite end-unit condo, nestled within one of Westport'...	3 beds \| 3 baths \| 3,691 sq.ft.	$1,575,000	Airbnb cash on cash: -0.55% Traditional cash on cash: -1% Airbnb Rental Income: $6343 Traditional Rental Income: $4437 Airbnb ROI: -0.55% Traditional ROI: -1%
249 Sturges Highway Westport, CT Relaxed, entertaining luxury with all the bells and whistles....Privacy, serenity and conv...	5 beds \| 9 baths \| 8,639 sq.ft.	$4,485,000	Airbnb cash on cash: -2.12% Traditional cash on cash: -1.27% Airbnb Rental Income: $5401 Traditional Rental Income: $7845 Airbnb ROI: -2.12% Traditional ROI: -1.27%
6 Hilly Field Lane Westport, CT Welcome to the most charming and delightful home in Old Hill! Beautiful 6 Hilly Field Lane...	4 beds \| 5 baths \| 2,950 sq.ft.	$2,265,000	Airbnb cash on cash: 0.2% Traditional cash on cash: -0.08% Airbnb Rental Income: $8730 Traditional Rental Income: $6498 Airbnb ROI: 0.2% Traditional ROI: -0.08%
3 Concord Lane Westport, CT Welcome to 3 Concord Lane! This unique and fabulous contemporary home is waiting for you! ...	2 beds \| 3 baths \| 1,769 sq.ft.	$1,299,000	Airbnb cash on cash: -1.08% Traditional cash on cash: -0.23% Airbnb Rental Income: $3311 Traditional Rental Income: $3592 Airbnb ROI: -1.08% Traditional ROI: -0.23%
24 Edgemarth Hill Road Westport, CT Construction is beginning on this stunning masterpiece by top Builder/Developer renowned f...	5 beds \| 7 baths \| 6,325 sq.ft.	$5,825,000	Airbnb cash on cash: -2.36% Traditional cash on cash: -1.72% Airbnb Rental Income: $5401 Traditional Rental Income: $7767 Airbnb ROI: -2.36% Traditional ROI: -1.72%
495 Main Street Westport, CT Nestled in the heart of Westport, 495 Main Street offers an amazing opportunity for those ...	3 beds \| 1 baths \| 1,674 sq.ft.	$850,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 0.39% Airbnb Rental Income: $6343 Traditional Rental Income: $2880 Airbnb ROI: 3.19% Traditional ROI: 0.39%
3 Mystic Lane Westport, CT This is the one! Welcome to 3 Mystic Lane, a home that exudes charm and many of the high-e...	4 beds \| 4 baths \| 2,913 sq.ft.	$1,499,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 0.48% Airbnb Rental Income: $8730 Traditional Rental Income: $5121 Airbnb ROI: 1.89% Traditional ROI: 0.48%
3 Clinton Avenue Westport, CT Welcome home to this vintage, 1930's walk-to-town Colonial that is perfectly finished with...	3 beds \| 2 baths \| 1,370 sq.ft.	$1,099,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 0.23% Airbnb Rental Income: $6343 Traditional Rental Income: $3527 Airbnb ROI: 1.77% Traditional ROI: 0.23%
65 Grove Point Westport, CT Welcome Home to Grove Point! Walk to the Beach! Ranch with Garage and Breezeway! Trex Deck...	3 beds \| 2 baths \| 1,722 sq.ft.	$899,900	Airbnb cash on cash: 2.81% Traditional cash on cash: 1.22% Airbnb Rental Income: $6343 Traditional Rental Income: $3758 Airbnb ROI: 2.81% Traditional ROI: 1.22%

Real Estate investment in Westport, CT

There are 36 properties for sale in the city of Westport . The median list price in Westport is $2,699,500 and the average price per square foot is $632. In December 2024, the average monthly cash on cash return in Westport is N/A%. The average monthly rental income in Westport is $6,609.

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

There are 36 investment properties available for sale in Westport.

In 2024, 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 $6,609.

Your search for investment property begins and ends here

Investment Property for Sale in Westport, CT

3 Nassau Road

Westport, CT

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

$3,500,000

Airbnb cash on cash: 0.04%

Traditional cash on cash: 0.73%

Airbnb Rental Income: $5401

Traditional Rental Income: $6562

Airbnb ROI: 0.04%

Traditional ROI: 0.73%

60 Wilton Road #Penthouse 4B

Westport, CT

2 beds | 3 baths | 2,437 sq.ft.

$3,650,000

Airbnb cash on cash: -2.4%

Traditional cash on cash: -1.67%

Airbnb Rental Income: $3311

Traditional Rental Income: $5061

Airbnb ROI: -2.4%

Traditional ROI: -1.67%

1 Crestwood Road

Westport, CT

5 beds | 7 baths | 5,700 sq.ft.

$2,899,000

Airbnb cash on cash: -1.56%

Traditional cash on cash: 1.05%

Airbnb Rental Income: $5401

Traditional Rental Income: $11349

Airbnb ROI: -1.56%

Traditional ROI: 1.05%

60 Wilton Road #2C

Westport, CT

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

$3,699,000

Airbnb cash on cash: -1.09%

Traditional cash on cash: -0.28%

Airbnb Rental Income: $8730

Traditional Rental Income: $9885

Airbnb ROI: -1.09%

Traditional ROI: -0.28%

41 Richmondville Avenue #210

Westport, CT

2 beds | 3 baths | 1,630 sq.ft.

$2,195,000

Airbnb cash on cash: -2.81%

Traditional cash on cash: -2.23%

Airbnb Rental Income: $3311

Traditional Rental Income: $3762

Airbnb ROI: -2.81%

Traditional ROI: -2.23%

443 Riverside Avenue

Westport, CT

3 beds | 4 baths | 2,547 sq.ft.

$2,500,000

Airbnb cash on cash: -0.97%

Traditional cash on cash: -0.95%

Airbnb Rental Income: $6343

Traditional Rental Income: $5160

Airbnb ROI: -0.97%

Traditional ROI: -0.95%

50 Compo Mill Cove

Westport, CT

5 beds | 7 baths | 3,955 sq.ft.

$12,250,000

Airbnb cash on cash: -2.78%

Traditional cash on cash: -2.46%

Airbnb Rental Income: $5401

Traditional Rental Income: $7986

Airbnb ROI: -2.78%

Traditional ROI: -2.46%

41 Richmondville Avenue #PH West

Westport, CT

3 beds | 3 baths | 2,400 sq.ft.

$3,195,000

Airbnb cash on cash: -2.35%

Traditional cash on cash: -2.64%

Airbnb Rental Income: $6343

Traditional Rental Income: $4250

Airbnb ROI: -2.35%