Real Estate Investments for Sale in Fairfield, CT With High ROI

Are you looking for a vacation rental in Fairfield, CT? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.

Explore a variety of short-term homes & houses in Fairfield, CT. Invest wisely with VRBO & Fairfield, CT Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Fairfield, CT

Search for Single Family Residential for Sale in Fairfield, Connecticut. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 46 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
27 Hulls Highway Fairfield, CT Incredible opportunity to live in one of the most sought after locations of Southport, CT....	2 beds \| 1 baths \| 1,843 sq.ft.	$669,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 1.46% Airbnb Rental Income: $3677 Traditional Rental Income: $2353 Airbnb ROI: 2.29% Traditional ROI: 1.46%
198 Castle Avenue Fairfield, CT Remodeled between 2019 to 2024. The open floor plan includes a fully renovated kitchen wit...	2 beds \| 1 baths \| 676 sq.ft.	$465,000	Airbnb cash on cash: 4.52% Traditional cash on cash: 3.4% Airbnb Rental Income: $3677 Traditional Rental Income: $2389 Airbnb ROI: 4.52% Traditional ROI: 3.4%
2117 Fairfield Beach Road Fairfield, CT Welcome to Turning Point at Pine Creek, where the coastline bends to a point creating some...	4 beds \| 5 baths \| 4,000 sq.ft.	$4,400,000	Airbnb cash on cash: -2.48% Traditional cash on cash: -1.08% Airbnb Rental Income: $3552 Traditional Rental Income: $8480 Airbnb ROI: -2.48% Traditional ROI: -1.08%
65 Rena Place Fairfield, CT Welcome home to 65 Rena Place; where peace, charm, and convenience meet to make this space...	4 beds \| 2 baths \| 1,355 sq.ft.	$520,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 4.97% Airbnb Rental Income: $3552 Traditional Rental Income: $3524 Airbnb ROI: 3.42% Traditional ROI: 4.97%
2087 Fairfield Beach Road Fairfield, CT Every room with a view! This fabulous waterfront home offers you the perfect retreat at th...	4 beds \| 3 baths \| 2,748 sq.ft.	$2,150,000	Airbnb cash on cash: -0.89% Traditional cash on cash: 0.06% Airbnb Rental Income: $3552 Traditional Rental Income: $4664 Airbnb ROI: -0.89% Traditional ROI: 0.06%
171 Henderson Road Fairfield, CT LOCATION, LOCATION, LOCATION! Welcome home to this beautifully renovated, oversized coloni...	4 beds \| 5 baths \| 3,600 sq.ft.	$799,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 9.66% Airbnb Rental Income: $3552 Traditional Rental Income: $9035 Airbnb ROI: 1.24% Traditional ROI: 9.66%
161 Brion Drive Fairfield, CT Well maintained three bedroom split level home on the corner of a cul-de-sac. This home ha...	3 beds \| 2 baths \| 1,664 sq.ft.	$400,000	Airbnb cash on cash: 8.99% Traditional cash on cash: 7.53% Airbnb Rental Income: $5722 Traditional Rental Income: $4035 Airbnb ROI: 8.99% Traditional ROI: 7.53%
72 Alberta Street Fairfield, CT Welcome to the charming 72 Alberta Street, a delightful 3bedroom Cape Cod style home with ...	3 beds \| 3 baths \| 1,999 sq.ft.	$810,000	Airbnb cash on cash: 3.9% Traditional cash on cash: 3.56% Airbnb Rental Income: $5722 Traditional Rental Income: $4324 Airbnb ROI: 3.9% Traditional ROI: 3.56%
98 Alvin Street Fairfield, CT Charming 4 bedroom 2 full bath home located nearby shopping, downtown Fairfield amenities,...	4 beds \| 2 baths \| 1,326 sq.ft.	$599,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 4.27% Airbnb Rental Income: $3552 Traditional Rental Income: $3672 Airbnb ROI: 2.66% Traditional ROI: 4.27%
1895 Fairfield Beach Road Fairfield, CT Live your dream at the water's edge. The 'Tackle Box' is the perfect seaside retreat. The ...	3 beds \| 2 baths \| 1,572 sq.ft.	$1,995,000	Airbnb cash on cash: 0.34% Traditional cash on cash: -0.19% Airbnb Rental Income: $5722 Traditional Rental Income: $3589 Airbnb ROI: 0.34% Traditional ROI: -0.19%
54 2nd Street Fairfield, CT Modern convenience meets historic charm in this beautifully updated antique three-bedroom,...	3 beds \| 2 baths \| 1,407 sq.ft.	$475,000	Airbnb cash on cash: 7.72% Traditional cash on cash: 4.53% Airbnb Rental Income: $5722 Traditional Rental Income: $3161 Airbnb ROI: 7.72% Traditional ROI: 4.53%
1660 Black Rock Turnpike Fairfield, CT Build your investment portfolio with this beautifully remodeled Black Rock single-family c...	4 beds \| 2 baths \| 1,438 sq.ft.	$599,900	Airbnb cash on cash: 1.66% Traditional cash on cash: 3.19% Airbnb Rental Income: $3552 Traditional Rental Income: $3632 Airbnb ROI: 1.66% Traditional ROI: 3.19%
1410 South Pine Creek Road Fairfield, CT Magnificent private custom built in 2005 Federal Colonial with views of Long Island Sound ...	5 beds \| 7 baths \| 7,798 sq.ft.	$5,988,800	Airbnb cash on cash: -1.91% Traditional cash on cash: -1.27% Airbnb Rental Income: $8468 Traditional Rental Income: $10442 Airbnb ROI: -1.91% Traditional ROI: -1.27%
184 Sigwin Drive Fairfield, CT Move right into this beautifully remodeled home located in the heart of Fairfield's highly...	3 beds \| 2 baths \| 1,588 sq.ft.	$775,000	Airbnb cash on cash: 4.03% Traditional cash on cash: 3.41% Airbnb Rental Income: $5722 Traditional Rental Income: $4132 Airbnb ROI: 4.03% Traditional ROI: 3.41%
136 Henderson Road Fairfield, CT Unbeatable Fairfield Lifestyle! Walk to the train, town, award winning schools and great r...	4 beds \| 3 baths \| 2,607 sq.ft.	$799,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 3.7% Airbnb Rental Income: $3552 Traditional Rental Income: $5177 Airbnb ROI: 0.47% Traditional ROI: 3.7%
20 Saint Marc Lane Fairfield, CT Welcome to 20 Saint Marc Lane, a magnificent build set quietly on a cul-de-sac in the hear...	5 beds \| 5 baths \| 4,000 sq.ft.	$1,899,900	Airbnb cash on cash: 0.71% Traditional cash on cash: 1.54% Airbnb Rental Income: $8468 Traditional Rental Income: $8325 Airbnb ROI: 0.71% Traditional ROI: 1.54%
2470 North Benson Road Fairfield, CT Introducing a stunning and sophisticated new construction located in the highly sought-aft...	5 beds \| 5 baths \| 4,032 sq.ft.	$1,875,000	Airbnb cash on cash: 0.76% Traditional cash on cash: -1.23% Airbnb Rental Income: $8468 Traditional Rental Income: $3404 Airbnb ROI: 0.76% Traditional ROI: -1.23%
4200 Congress Street Fairfield, CT Welcome to this luxurious expanded ranch in the desirable Greenfield Hill neighborhood of ...	4 beds \| 5 baths \| 3,005 sq.ft.	$1,449,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 3.17% Airbnb Rental Income: $3552 Traditional Rental Income: $8578 Airbnb ROI: -1.14% Traditional ROI: 3.17%
194 Sasco River Lane Fairfield, CT SOUTHPORT - Superb opportunity to renovate this expansive 5000 square foot, 4/5 Bedroom, 3...	5 beds \| 4 baths \| 5,012 sq.ft.	$1,395,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 2.36% Airbnb Rental Income: $8468 Traditional Rental Income: $7204 Airbnb ROI: 2.1% Traditional ROI: 2.36%
139 High Meadow Road Fairfield, CT Don't miss this opportunity to own a stunning home in a prime Southport location! Nestled ...	4 beds \| 4 baths \| 3,610 sq.ft.	$1,499,900	Airbnb cash on cash: -1.21% Traditional cash on cash: 1.46% Airbnb Rental Income: $3552 Traditional Rental Income: $6489 Airbnb ROI: -1.21% Traditional ROI: 1.46%
342 Midlock Road Fairfield, CT Stately and gracious Greenfield Hill charmer on 2+ acres of manicured lawn with amazing de...	5 beds \| 9 baths \| 7,269 sq.ft.	$2,875,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 0.67% Airbnb Rental Income: $8468 Traditional Rental Income: $10244 Airbnb ROI: -0.59% Traditional ROI: 0.67%
366 Suburban Avenue Fairfield, CT The quintessential charm of this 1912 colonial invites you home. Nearly 1500 sq feet of li...	3 beds \| 2 baths \| 1,442 sq.ft.	$525,000	Airbnb cash on cash: 6.02% Traditional cash on cash: 3.63% Airbnb Rental Income: $5722 Traditional Rental Income: $3407 Airbnb ROI: 6.02% Traditional ROI: 3.63%
59 Sasco Hill Terrace Fairfield, CT Lovely Sasco Cape with Traditional Floor Plan sits on Sunny .22 acre! Redo or rebuild. New...	3 beds \| 2 baths \| 1,294 sq.ft.	$799,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 1.05% Airbnb Rental Income: $5722 Traditional Rental Income: $3199 Airbnb ROI: 2.9% Traditional ROI: 1.05%
167 Rakoczy Avenue Fairfield, CT Discover the potential of this spacious Fairfield home, offering an inviting layout that's...	4 beds \| 3 baths \| 2,380 sq.ft.	$699,900	Airbnb cash on cash: 0.98% Traditional cash on cash: 3.87% Airbnb Rental Income: $3552 Traditional Rental Income: $4657 Airbnb ROI: 0.98% Traditional ROI: 3.87%
8 Hazel Street Fairfield, CT Welcome to Fairfield! Cozy three bedroom cape with spacious office/den on second floor. Co...	3 beds \| 1 baths \| 1,152 sq.ft.	$489,000	Airbnb cash on cash: 6.69% Traditional cash on cash: 2.89% Airbnb Rental Income: $5722 Traditional Rental Income: $2844 Airbnb ROI: 6.69% Traditional ROI: 2.89%
1810 Fairfield Beach Road Fairfield, CT Welcome to 1810 Fairfield Beach Road, a breathtaking 4-bedroom colonial with panoramic wat...	4 beds \| 3 baths \| 2,412 sq.ft.	$2,149,000	Airbnb cash on cash: -1.79% Traditional cash on cash: -0.2% Airbnb Rental Income: $3552 Traditional Rental Income: $5948 Airbnb ROI: -1.79% Traditional ROI: -0.2%
898 Cross Highway Fairfield, CT Antique Perfection with Separate Guest House/Barn on pastoral acreage! Fully rebuilt in 20...	4 beds \| 5 baths \| 4,020 sq.ft.	$2,095,000	Airbnb cash on cash: -1.75% Traditional cash on cash: 1.41% Airbnb Rental Income: $3552 Traditional Rental Income: $8926 Airbnb ROI: -1.75% Traditional ROI: 1.41%
79 Mayweed Road Fairfield, CT It's finally here! Rare and coveted opportunity to be on a cul-de-sac in the heart of the ...	4 beds \| 5 baths \| 4,109 sq.ft.	$1,400,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 3.34% Airbnb Rental Income: $3552 Traditional Rental Income: $8510 Airbnb ROI: -1.07% Traditional ROI: 3.34%
34 Bennett Street Fairfield, CT Welcome to this charming Cape Cod-style home located in the highly sought-after Stratfield...	3 beds \| 2 baths \| 1,434 sq.ft.	$465,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 5.36% Airbnb Rental Income: $5722 Traditional Rental Income: $3783 Airbnb ROI: 7.19% Traditional ROI: 5.36%
183 Pepperidge Circle Fairfield, CT The vibe and efficiency of the mid-century split is poised for a comeback. Why you ask? A ...	3 beds \| 2 baths \| 1,980 sq.ft.	$585,000	Airbnb cash on cash: 5.09% Traditional cash on cash: 4.61% Airbnb Rental Income: $5722 Traditional Rental Income: $4319 Airbnb ROI: 5.09% Traditional ROI: 4.61%
207 Riverview Circle Fairfield, CT Welcome to 207 Riverview Circle located in the sought-after Riverfield section of Fairfiel...	4 beds \| 3 baths \| 2,870 sq.ft.	$799,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 5.04% Airbnb Rental Income: $3552 Traditional Rental Income: $6172 Airbnb ROI: 0.47% Traditional ROI: 5.04%
311 Berwick Avenue Fairfield, CT Welcome to 311 Berwick Ave! This thoughtfully designed Colonial home features 6 rooms, inc...	3 beds \| 3 baths \| 1,993 sq.ft.	$599,900	Airbnb cash on cash: 4.89% Traditional cash on cash: 3.82% Airbnb Rental Income: $5722 Traditional Rental Income: $3980 Airbnb ROI: 4.89% Traditional ROI: 3.82%
451 Burroughs Road Fairfield, CT Exquisite Contemporary Ranch that has been extensively renovated throughout offers a gener...	4 beds \| 3 baths \| 2,142 sq.ft.	$699,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 3.89% Airbnb Rental Income: $3552 Traditional Rental Income: $4669 Airbnb ROI: 0.98% Traditional ROI: 3.89%
67 Old Elm Road Fairfield, CT Nestled on a quiet and very desirable cul-de-sac in a sought after neighborhood, this spec...	4 beds \| 2 baths \| 1,476 sq.ft.	$595,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 3.37% Airbnb Rental Income: $3552 Traditional Rental Income: $3703 Airbnb ROI: 1.7% Traditional ROI: 3.37%
104 Carroll Road Fairfield, CT Welcome to this inviting 3-bedroom, 3-full-bath home, where possibilities abound. Featurin...	3 beds \| 3 baths \| 2,128 sq.ft.	$699,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 3.48% Airbnb Rental Income: $5722 Traditional Rental Income: $4398 Airbnb ROI: 3.76% Traditional ROI: 3.48%
1240 Westport Turnpike Fairfield, CT 5,000+ sq ft with 4 full floors of living space! Get away from it all and still be close t...	3 beds \| 6 baths \| 3,638 sq.ft.	$1,749,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 2.08% Airbnb Rental Income: $5722 Traditional Rental Income: $8551 Airbnb ROI: -0.37% Traditional ROI: 2.08%
885 Duck Farm Road Fairfield, CT Not one but two. Renowned architect, Jack Franzen and builder, Frank Dooley, applied their...	5 beds \| 4 baths \| 3,482 sq.ft.	$1,450,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 2.07% Airbnb Rental Income: $8468 Traditional Rental Income: $7103 Airbnb ROI: 1.9% Traditional ROI: 2.07%
658 Hoydens Hill Road Fairfield, CT Antique lover's dream...If you love authentic features and appreciate excellent craftsmans...	5 beds \| 7 baths \| 5,730 sq.ft.	$1,850,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 2.75% Airbnb Rental Income: $8468 Traditional Rental Income: $10203 Airbnb ROI: 0.81% Traditional ROI: 2.75%
1018 High Street Fairfield, CT This charming Colonial in the University area is picture-perfect and move-in ready! Corner...	4 beds \| 3 baths \| 2,414 sq.ft.	$1,100,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 1.88% Airbnb Rental Income: $3552 Traditional Rental Income: $5222 Airbnb ROI: -0.51% Traditional ROI: 1.88%
570 Warner Hill Road Fairfield, CT Welcome HOME to 570 Warner Hill Road....A captivating blend of modern elegance & cozy char...	4 beds \| 4 baths \| 4,912 sq.ft.	$2,450,000	Airbnb cash on cash: -1.95% Traditional cash on cash: -0.19% Airbnb Rental Income: $3552 Traditional Rental Income: $6775 Airbnb ROI: -1.95% Traditional ROI: -0.19%

Your search for investment property begins and ends here

Single Family Homes for Sale in Fairfield, CT

27 Hulls Highway

Fairfield, CT

2 beds | 1 baths | 1,843 sq.ft.

$669,000

Airbnb cash on cash: 2.29%

Traditional cash on cash: 1.46%

Airbnb Rental Income: $3677

Traditional Rental Income: $2353

Airbnb ROI: 2.29%

Traditional ROI: 1.46%

198 Castle Avenue

Fairfield, CT

2 beds | 1 baths | 676 sq.ft.

$465,000

Airbnb cash on cash: 4.52%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $3677

Traditional Rental Income: $2389

Airbnb ROI: 4.52%

Traditional ROI: 3.4%

2117 Fairfield Beach Road

Fairfield, CT

4 beds | 5 baths | 4,000 sq.ft.

$4,400,000

Airbnb cash on cash: -2.48%

Traditional cash on cash: -1.08%

Airbnb Rental Income: $3552

Traditional Rental Income: $8480

Airbnb ROI: -2.48%

Traditional ROI: -1.08%

65 Rena Place

Fairfield, CT

4 beds | 2 baths | 1,355 sq.ft.

$520,000

Airbnb cash on cash: 3.42%

Traditional cash on cash: 4.97%

Airbnb Rental Income: $3552

Traditional Rental Income: $3524

Airbnb ROI: 3.42%

Traditional ROI: 4.97%

2087 Fairfield Beach Road

Fairfield, CT

4 beds | 3 baths | 2,748 sq.ft.

$2,150,000

Airbnb cash on cash: -0.89%

Traditional cash on cash: 0.06%

Airbnb Rental Income: $3552

Traditional Rental Income: $4664

Airbnb ROI: -0.89%

Traditional ROI: 0.06%

171 Henderson Road

Fairfield, CT

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

$799,000

Airbnb cash on cash: 1.24%

Traditional cash on cash: 9.66%

Airbnb Rental Income: $3552

Traditional Rental Income: $9035

Airbnb ROI: 1.24%

Traditional ROI: 9.66%

161 Brion Drive

Fairfield, CT

3 beds | 2 baths | 1,664 sq.ft.

$400,000

Airbnb cash on cash: 8.99%

Traditional cash on cash: 7.53%

Airbnb Rental Income: $5722

Traditional Rental Income: $4035

Airbnb ROI: 8.99%

Traditional ROI: 7.53%

72 Alberta Street

Fairfield, CT

3 beds | 3 baths | 1,999 sq.ft.

$810,000

Airbnb cash on cash: 3.9%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $5722

Traditional Rental Income: $4324

Airbnb ROI: 3.9%