Real Estate Investment Properties for Sale in Fairfield, CT

Looking for investment property in Fairfield, CT with high ROI ?

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.

Investment Property for Sale in Fairfield, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2 Elmwood Drive #2 Fairfield, CT Rare offering in the coveted Southport Green complex, just steps from Southport Village an...	3 beds \| 4 baths \| 3,328 sq.ft.	$2,495,000	Airbnb cash on cash: -1.53% Traditional cash on cash: 0.29% Airbnb Rental Income: $2373 Traditional Rental Income: $5995 Airbnb ROI: -1.53% Traditional ROI: 0.29%
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: -2.37% Traditional cash on cash: -1.54% Airbnb Rental Income: $4099 Traditional Rental Income: $6605 Airbnb ROI: -2.37% Traditional ROI: -1.54%
1008 Fairfield Beach Road Fairfield, CT Welcome to the pinnacle of luxury coastal living at 1008 Fairfield Beach Road- where moder...	5 beds \| 5 baths \| 4,100 sq.ft.	$3,900,000	Airbnb cash on cash: -2.68% Traditional cash on cash: -0.56% Airbnb Rental Income: $2322 Traditional Rental Income: $9381 Airbnb ROI: -2.68% Traditional ROI: -0.56%
76 Hilary Circle #76 Fairfield, CT A rare end-unit townhome offering exceptional space, privacy, and a thoughtfully designed ...	3 beds \| 4 baths \| 3,229 sq.ft.	$999,000	Airbnb cash on cash: -1.64% Traditional cash on cash: 3.22% Airbnb Rental Income: $2373 Traditional Rental Income: $6309 Airbnb ROI: -1.64% Traditional ROI: 3.22%
309 Hunyadi Avenue Fairfield, CT Welcome to 309 Hunyadi Avenue, a beautifully designed 5-bedroom, 6-bath new construction C...	5 beds \| 6 baths \| 4,239 sq.ft.	$1,950,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 3.8% Airbnb Rental Income: $2322 Traditional Rental Income: $9471 Airbnb ROI: -0.47% Traditional ROI: 3.8%
1410 South Pine Creek Road Fairfield, CT Imagine starting each day with breathtaking sunrises over the water, the salty breeze on y...	5 beds \| 7 baths \| 5,198 sq.ft.	$5,500,000	Airbnb cash on cash: -2.81% Traditional cash on cash: -1.6% Airbnb Rental Income: $2322 Traditional Rental Income: $7931 Airbnb ROI: -2.81% Traditional ROI: -1.6%
2107 North Benson Road Fairfield, CT Welcome to 2107 North Benson, a rare Fairfield gem offering a perfect blend of versatility...	4 beds \| 5 baths \| 3,957 sq.ft.	$1,000,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 6.6% Airbnb Rental Income: $4099 Traditional Rental Income: $9146 Airbnb ROI: 0.24% Traditional ROI: 6.6%
706 Judd Street Fairfield, CT NEW Custom built home boasting sophisticated & unique design in the coveted University are...	5 beds \| 6 baths \| 4,150 sq.ft.	$1,800,000	Airbnb cash on cash: -2.14% Traditional cash on cash: 2.86% Airbnb Rental Income: $2322 Traditional Rental Income: $10111 Airbnb ROI: -2.14% Traditional ROI: 2.86%
3853 Congress Street Fairfield, CT Sprawling ten room ranch style residence offering 3 acres on a prime estate street in Gree...	4 beds \| 6 baths \| 4,906 sq.ft.	$1,395,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 5.17% Airbnb Rental Income: $4099 Traditional Rental Income: $10847 Airbnb ROI: -0.71% Traditional ROI: 5.17%
478 Crestwood Road Fairfield, CT Classic Colonial in Prime University Area Location. This 1937 Colonial offers four finishe...	5 beds \| 3 baths \| 3,469 sq.ft.	$1,495,000	Airbnb cash on cash: -1.94% Traditional cash on cash: 0.97% Airbnb Rental Income: $2322 Traditional Rental Income: $5781 Airbnb ROI: -1.94% Traditional ROI: 0.97%
35 Millard Street Fairfield, CT A Rare Opportunity in the Beach Area- Set on an oversized .42-acre lot at the end of a qui...	4 beds \| 5 baths \| 3,985 sq.ft.	$2,599,000	Airbnb cash on cash: -1.83% Traditional cash on cash: 0.47% Airbnb Rental Income: $4099 Traditional Rental Income: $8787 Airbnb ROI: -1.83% Traditional ROI: 0.47%
972 South Pine Creek Road #972 Fairfield, CT Nestled in a serene, beautifully landscaped community, this gracious townhouse at Pine Rid...	2 beds \| 3 baths \| 2,184 sq.ft.	$999,999	Airbnb cash on cash: -1.59% Traditional cash on cash: 0.44% Airbnb Rental Income: $2828 Traditional Rental Income: $4058 Airbnb ROI: -1.59% Traditional ROI: 0.44%
2015 Redding Road Fairfield, CT Majestically sited on 2 private acres of professionally landscaped grounds, this exception...	5 beds \| 6 baths \| 5,965 sq.ft.	$2,995,000	Airbnb cash on cash: -2.54% Traditional cash on cash: 0.46% Airbnb Rental Income: $2322 Traditional Rental Income: $10084 Airbnb ROI: -2.54% Traditional ROI: 0.46%
20 Ermine Street Fairfield, CT Endless opportunities await at this property-whether a buyer envisions their ideal home, a...	4 beds \| 2 baths \| 1,925 sq.ft.	$1,800,000	Airbnb cash on cash: -1.26% Traditional cash on cash: -0.72% Airbnb Rental Income: $4099 Traditional Rental Income: $4115 Airbnb ROI: -1.26% Traditional ROI: -0.72%
153 Pease Avenue Fairfield, CT Newly Renovated Colonial in Prime Southport Location. Beautifully updated colonial offerin...	4 beds \| 3 baths \| 3,597 sq.ft.	$1,495,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 0.52% Airbnb Rental Income: $4099 Traditional Rental Income: $5159 Airbnb ROI: -0.87% Traditional ROI: 0.52%
893 Church Hill Road Fairfield, CT MAKE THIS HOME For the HOLIDAYS! Sellers are motivated Make an offer! This home is ready f...	4 beds \| 2 baths \| 2,210 sq.ft.	$729,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 2.76% Airbnb Rental Income: $4099 Traditional Rental Income: $4092 Airbnb ROI: 1.49% Traditional ROI: 2.76%
115 Mayfair Road Fairfield, CT Welcome to 115 Mayfair Road This stunning 4-bedroom, 3-bath home has been fully renovated,...	4 beds \| 3 baths \| 2,012 sq.ft.	$1,179,999	Airbnb cash on cash: -0.27% Traditional cash on cash: 0.88% Airbnb Rental Income: $4099 Traditional Rental Income: $4495 Airbnb ROI: -0.27% Traditional ROI: 0.88%
221 Hunyadi Avenue Fairfield, CT Beautifully maintained brick two-family in Fairfield's sought-after Holland Hill neighborh...	4 beds \| 2 baths \| 2,376 sq.ft.	$775,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 2.31% Airbnb Rental Income: $4099 Traditional Rental Income: $4016 Airbnb ROI: 1.21% Traditional ROI: 2.31%
162 Country Road #162 Fairfield, CT Located in the highly desirable University area of Fairfield, this meticulously maintained...	4 beds \| 3 baths \| 2,516 sq.ft.	$825,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 2.57% Airbnb Rental Income: $4099 Traditional Rental Income: $4472 Airbnb ROI: 0.95% Traditional ROI: 2.57%
210 Pansy Road Fairfield, CT Welcome to 210 Pansy Road, a stunning new construction in Fairfield, CT offering nearly 4,...	5 beds \| 4 baths \| 3,780 sq.ft.	$1,949,000	Airbnb cash on cash: -2.22% Traditional cash on cash: 0.49% Airbnb Rental Income: $2322 Traditional Rental Income: $6644 Airbnb ROI: -2.22% Traditional ROI: 0.49%
22 Brett Road Fairfield, CT Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Sceni...	5 beds \| 6 baths \| 5,000 sq.ft.	$3,750,000	Airbnb cash on cash: -2.66% Traditional cash on cash: -0.3% Airbnb Rental Income: $2322 Traditional Rental Income: $9948 Airbnb ROI: -2.66% Traditional ROI: -0.3%
419 Valley Road Fairfield, CT Luxurious, like new construction home located in the desirable Stratfield Village neighbor...	4 beds \| 5 baths \| 3,224 sq.ft.	$1,589,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 2.37% Airbnb Rental Income: $4099 Traditional Rental Income: $8216 Airbnb ROI: -1.01% Traditional ROI: 2.37%
947 Galloping Hill Road Fairfield, CT Welcome to 947 Galloping Hill Road. This true mid-century modern home was designed by the ...	4 beds \| 4 baths \| 4,024 sq.ft.	$1,299,999	Airbnb cash on cash: -0.54% Traditional cash on cash: 2.49% Airbnb Rental Income: $4099 Traditional Rental Income: $6880 Airbnb ROI: -0.54% Traditional ROI: 2.49%
80 Gilbert Highway Fairfield, CT Through a pillared entrance sited privately from the road discover a tremendous opportunit...	4 beds \| 3 baths \| 1,664 sq.ft.	$799,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 2.62% Airbnb Rental Income: $4099 Traditional Rental Income: $4374 Airbnb ROI: 1.08% Traditional ROI: 2.62%
357 Harvester Road Fairfield, CT Now offered at $678,900! PRICE REFRESH! Welcome to this cheerful North Stratfield ranch, o...	3 beds \| 2 baths \| 1,572 sq.ft.	$678,900	Airbnb cash on cash: -0.45% Traditional cash on cash: 2.46% Airbnb Rental Income: $2373 Traditional Rental Income: $3627 Airbnb ROI: -0.45% Traditional ROI: 2.46%
122 Colony Street Fairfield, CT Yes, I am 100 years old and still standing. Yes, I need lots of love and appreciation. Bui...	3 beds \| 1 baths \| 1,217 sq.ft.	$300,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 6.94% Airbnb Rental Income: $2373 Traditional Rental Income: $2931 Airbnb ROI: 2.89% Traditional ROI: 6.94%
41 Pepperbush Lane Fairfield, CT Endless possibilities await in this 3-bedroom, 2.5-bath home located in a highly desirable...	3 beds \| 3 baths \| 2,045 sq.ft.	$750,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 2.77% Airbnb Rental Income: $2373 Traditional Rental Income: $4214 Airbnb ROI: -0.7% Traditional ROI: 2.77%
137 Millard Street Fairfield, CT This exceptional coastal residence offers a rare blend of timeless design and modern finis...	4 beds \| 4 baths \| 3,000 sq.ft.	$1,999,999	Airbnb cash on cash: -1.44% Traditional cash on cash: 0.12% Airbnb Rental Income: $4099 Traditional Rental Income: $6129 Airbnb ROI: -1.44% Traditional ROI: 0.12%
11 Judges Hollow Road Fairfield, CT Eight minutes from downtown Westport, escape to 11 Judges Hollow-a 1930's rustic hunting c...	2 beds \| 2 baths \| 1,135 sq.ft.	$950,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 0.31% Airbnb Rental Income: $2828 Traditional Rental Income: $3137 Airbnb ROI: -0.78% Traditional ROI: 0.31%
360 Duck Farm Road Fairfield, CT Cast one's eyes upon this special setting and you're instantly reminded of Mark Twain's qu...	5 beds \| 7 baths \| 4,700 sq.ft.	$2,299,000	Airbnb cash on cash: -2.36% Traditional cash on cash: 1.51% Airbnb Rental Income: $2322 Traditional Rental Income: $9997 Airbnb ROI: -2.36% Traditional ROI: 1.51%
232 Church Hill Road Fairfield, CT Welcome to this classic and charming brick Cape Cod, a warm and inviting home. Set on a le...	3 beds \| 2 baths \| 2,384 sq.ft.	$729,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 2.6% Airbnb Rental Income: $2373 Traditional Rental Income: $3982 Airbnb ROI: -0.63% Traditional ROI: 2.6%
279 Knapps Highway Fairfield, CT Welcome to this charming 4 bedroom Cape set on a deep, level lot in a convenient Fairfield...	4 beds \| 1 baths \| 1,086 sq.ft.	$525,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 2.97% Airbnb Rental Income: $4099 Traditional Rental Income: $3083 Airbnb ROI: 3.26% Traditional ROI: 2.97%
8 Nelson Place Fairfield, CT This exceptional opportunity presents itself in the Stratford neighborhood of Fairfield, n...	3 beds \| 2 baths \| 2,509 sq.ft.	$699,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 3.73% Airbnb Rental Income: $2373 Traditional Rental Income: $4560 Airbnb ROI: -0.52% Traditional ROI: 3.73%

Real Estate investment in Fairfield, CT

There are 39 properties for sale in the city of Fairfield . The median list price in Fairfield is $1,495,000 and the average price per square foot is $478. In December 2025, the average monthly cash on cash return in Fairfield is 2.00%. The average monthly rental income in Fairfield is $5,443.

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

There are 39 investment properties available for sale in Fairfield.

In 2025, the best neighborhood to buy investment property is Fairfield.

The ROI for Long-Term is higher than the Short-Term in Fairfield with average rental income of $5,443.

Your search for investment property begins and ends here

Investment Property for Sale in Fairfield, CT

2 Elmwood Drive #2

Fairfield, CT

3 beds | 4 baths | 3,328 sq.ft.

$2,495,000

Airbnb cash on cash: -1.53%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $2373

Traditional Rental Income: $5995

Airbnb ROI: -1.53%

Traditional ROI: 0.29%

2117 Fairfield Beach Road

Fairfield, CT

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

$4,400,000

Airbnb cash on cash: -2.37%

Traditional cash on cash: -1.54%

Airbnb Rental Income: $4099

Traditional Rental Income: $6605

Airbnb ROI: -2.37%

Traditional ROI: -1.54%

1008 Fairfield Beach Road

Fairfield, CT

5 beds | 5 baths | 4,100 sq.ft.

$3,900,000

Airbnb cash on cash: -2.68%

Traditional cash on cash: -0.56%

Airbnb Rental Income: $2322

Traditional Rental Income: $9381

Airbnb ROI: -2.68%

Traditional ROI: -0.56%

76 Hilary Circle #76

Fairfield, CT

3 beds | 4 baths | 3,229 sq.ft.

$999,000

Airbnb cash on cash: -1.64%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $2373

Traditional Rental Income: $6309

Airbnb ROI: -1.64%

Traditional ROI: 3.22%

309 Hunyadi Avenue

Fairfield, CT

5 beds | 6 baths | 4,239 sq.ft.

$1,950,000

Airbnb cash on cash: -0.47%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $2322

Traditional Rental Income: $9471

Airbnb ROI: -0.47%

Traditional ROI: 3.8%

1410 South Pine Creek Road

Fairfield, CT

5 beds | 7 baths | 5,198 sq.ft.

$5,500,000

Airbnb cash on cash: -2.81%

Traditional cash on cash: -1.6%

Airbnb Rental Income: $2322

Traditional Rental Income: $7931

Airbnb ROI: -2.81%

Traditional ROI: -1.6%

2107 North Benson Road

Fairfield, CT

4 beds | 5 baths | 3,957 sq.ft.

$1,000,000

Airbnb cash on cash: 0.24%

Traditional cash on cash: 6.6%

Airbnb Rental Income: $4099

Traditional Rental Income: $9146

Airbnb ROI: 0.24%

Traditional ROI: 6.6%

706 Judd Street

Fairfield, CT

5 beds | 6 baths | 4,150 sq.ft.

$1,800,000

Airbnb cash on cash: -2.14%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $2322

Traditional Rental Income: $10111

Airbnb ROI: -2.14%