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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
143 Roseville RoadWestport, CTNestled in peaceful seclusion yet just moments to town's shops, restaurants and amenities,... |
4 beds | 5 baths | 4,100 sq.ft. |
$4,375,000 |
Airbnb cash on cash: -0.72%
|
60 Wilton Road #2CWestport, CTFully 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: -2.54%
|
41 Richmondville Avenue #Duplex 1Westport, CTA 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: -2.17%
|
61 Clapboard Hill RoadWestport, CTLocated in prestigious Greens Farms, this European-inspired Colonial offers a rare opportu... |
4 beds | 4 baths | 3,418 sq.ft. |
$3,850,000 |
Airbnb cash on cash: -1.03%
|
3 Laurel LaneWestport, CTWelcome to this new construction project which is currently underway, with an expected com... |
4 beds | 6 baths | 4,204 sq.ft. |
$3,685,000 |
Airbnb cash on cash: -0.6%
|
11 Edgewater HillsideWestport, CTCOMPO 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: -1.11%
|
1 Coastal CourtWestport, CTIntroducing 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: -2.29%
|
4 Woods Grove RoadWestport, CTHUGE 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: 0.27%
|
25 Old RoadWestport, CTSet in Westport's sought-after Hunt Club neighborhood, this European-inspired Colonial off... |
5 beds | 5 baths | 6,330 sq.ft. |
$2,200,000 |
Airbnb cash on cash: 0.15%
|
2 Charcoal LaneWestport, CTExceptional privacy meets modern luxury on over 2 secluded acres at the end of a quiet cul... |
3 beds | 3 baths | 3,810 sq.ft. |
$2,198,000 |
Airbnb cash on cash: -0.21%
|
13 Rockyfield RoadWestport, CTThe Legacy of Elegance: 1.12 Acres in the Heart of Westport. Some homes are built for a ma... |
5 beds | 6 baths | 7,409 sq.ft. |
$3,990,000 |
Airbnb cash on cash: -0.62%
|
7 Rowland PlaceWestport, CTCharming, Light-Filled, Beach Cottage In Saugatuck Shores; A few steps From The Water, Kit... |
2 beds | 1 baths | 948 sq.ft. |
$985,000 |
Airbnb cash on cash: 0.57%
|
55 Center StreetWestport, CTLocated 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: -0.22%
|
104 Harvest Commons #104Westport, CTBeautifully 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: -0.12%
|
119 Kings Highway NWestport, CTHouse and land are fully available. Build your dream house on this beautiful lot in the Ol... |
2 beds | 2 baths | 1,400 sq.ft. |
$1,250,000 |
Airbnb cash on cash: 0.08%
|
24 Blue Ribbon DriveWestport, 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: -0.64%
|
21 Covlee DrWestport, CT21 Covlee Dr, Westport, CT 06880 | Single Family Residential |
4 beds | 4 baths | 4,444 sq.ft. |
$6,875,000 |
Airbnb cash on cash: -2.81%
|
11 Wake Robin RoadWestport, CTJust completed and ready for immediate occupancy, this beautifully crafted new constructio... |
5 beds | 6 baths | 7,583 sq.ft. |
$4,799,000 |
Airbnb cash on cash: -2.26%
|
1 Greystone Farm LaneWestport, CTExperience the perfect harmony of sophisticated architecture and bucolic charm in this Col... |
5 beds | 6 baths | 5,182 sq.ft. |
$4,199,000 |
Airbnb cash on cash: -0.56%
|
19 E Horseshoe LaneWestport, CTLocated on a quiet cul de sac only one mile from Metro North Train Station/I95 and two mil... |
5 beds | 5 baths | 5,476 sq.ft. |
$3,190,000 |
Airbnb cash on cash: -0.44%
|
3 Stonewall LaneWestport, CTTucked away on a coveted Westport lane, 3 Stonewall Ln. offers an exceptional blend of sop... |
5 beds | 7 baths | 8,694 sq.ft. |
$4,000,000 |
Airbnb cash on cash: -0.69%
|
4 Charcoal LaneWestport, CTA rare offering indeed! Welcome to 4 Charcoal Lane, an unrivaled multi-generational estate... |
5 beds | 5 baths | 6,015 sq.ft. |
$3,450,000 |
Airbnb cash on cash: -0.46%
|
3 Cedar Pond RoadWestport, CTTucked away at the end of a long private drive, this exceptional property offers rare priv... |
4 beds | 4 baths | 3,046 sq.ft. |
$1,890,000 |
Airbnb cash on cash: -0.41%
|
30 Pequot TrailWestport, CTCoveted Old Hill neighborhood! This stone and shingle 10 room colonial is detailed with cu... |
5 beds | 4 baths | 3,156 sq.ft. |
$1,599,876 |
Airbnb cash on cash: 0.83%
|
32 Whitney Glen #32Westport, CTWhitney 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: 0.5%
|
4 Cardinal LaneWestport, CTWelcome 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: -0.73%
|
20 Cross Street #7Westport, CTThis 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: 0.72%
|
28 Ferry Lane EWestport, CTLooking for a sensational home just a short walk to the beach, Longshore, train, and resta... |
5 beds | 9 baths | 8,466 sq.ft. |
$6,250,000 |
Airbnb cash on cash: -1.01%
|
22 Dawn DriveWestport, CTCome walk this stunning 1.5 acre lot with me - totally private, tucked at the end of a cul... |
4 beds | 5 baths | 4,000 sq.ft. |
$4,995,700 |
Airbnb cash on cash: -0.76%
|
21 Dover RoadWestport, CTSpacious and impeccably maintained Colonial tucked away on a quiet cul-de-sac in one of We... |
5 beds | 5 baths | 6,356 sq.ft. |
$2,750,000 |
Airbnb cash on cash: -0.2%
|
47 Charcoal Hill RoadWestport, CTDesigned by renowned architect and builder Frazier Forman Peters, this stone estate is set... |
4 beds | 6 baths | 10,522 sq.ft. |
$10,500,000 |
Airbnb cash on cash: -1.36%
|
22 Evergreen AvenueWestport, CTIntroducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded r... |
5 beds | 5 baths | 5,103 sq.ft. |
$4,850,000 |
Airbnb cash on cash: -0.69%
|
34 Pequot TrailWestport, CTDiscover this serene setting in a sought after Old Hill neighborhood. Two thoughtful and b... |
5 beds | 4 baths | 3,782 sq.ft. |
$2,100,000 |
Airbnb cash on cash: 0.3%
|
31 Stonybrook RoadWestport, CTTucked behind a gated entry in Old Hill, this stunning 5 bedroom, 6.2 bath home offers a r... |
5 beds | 8 baths | 6,503 sq.ft. |
$5,750,000 |
Airbnb cash on cash: -1.02%
|
30 Saint Johns PlaceWestport, CTSaint John Place is the street people who know Westport quietly hope opens up. It almost n... |
5 beds | 4 baths | 3,999 sq.ft. |
$2,895,000 |
Airbnb cash on cash: -0.06%
|
Real Estate investment in Westport, CT
There are 37 properties for sale in the city of Westport . The median list price in Westport is $2,098,916 and the average price per square foot is $446. In June 2026, the average monthly cash on cash return in Westport is 1.00%. The average monthly rental income in Westport is $8,103.