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.

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 48 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
125 Vesper Street Fairfield, CT OPEN HOUSES CANCELLED. Nestled on a charming tree-lined street, this sun-filled 3-bedroom ...	3 beds \| 2 baths \| 1,896 sq.ft.	$625,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 4.14% Airbnb Rental Income: $2373 Traditional Rental Income: $3753 Airbnb ROI: 0.77% Traditional ROI: 4.14%
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%
91 Henderson Road Fairfield, CT Welcome to one of Fairfield's more "walkable" streets, located just steps from the vibrant...	3 beds \| 3 baths \| 1,662 sq.ft.	$799,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 3.42% Airbnb Rental Income: $2373 Traditional Rental Income: $4093 Airbnb ROI: 0.32% Traditional ROI: 3.42%
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%
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: 1.54% Traditional cash on cash: 7.53% Airbnb Rental Income: $2373 Traditional Rental Income: $4035 Airbnb ROI: 1.54% Traditional ROI: 7.53%
450 Penfield Road Fairfield, CT New Construction in coveted BEACH AREA! This 4,000 sqft custom Colonial blends coastal cha...	5 beds \| 5 baths \| 4,000 sq.ft.	$3,100,000	Airbnb cash on cash: -0.89% Traditional cash on cash: -0.15% Airbnb Rental Income: $2322 Traditional Rental Income: $3859 Airbnb ROI: -0.89% Traditional ROI: -0.15%
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%
72 Lloyd Drive Fairfield, CT Absolutely stunning new construction-an elegantly crafted 5-BDR, 4.5-BTH residence that bl...	5 beds \| 5 baths \| 4,038 sq.ft.	$1,625,000	Airbnb cash on cash: -2.04% Traditional cash on cash: -1.08% Airbnb Rental Income: $2322 Traditional Rental Income: $3187 Airbnb ROI: -2.04% Traditional ROI: -1.08%
261 High Street Fairfield, CT Beautifully updated home ready for its new owners. Featuring a bright open concept floor p...	3 beds \| 2 baths \| 1,560 sq.ft.	$624,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 2.88% Airbnb Rental Income: $2373 Traditional Rental Income: $3593 Airbnb ROI: -0.22% Traditional ROI: 2.88%
60 Meadowbrook Road Fairfield, CT Coastal Charm Meets Modern Luxury in Fairfield, CT Looking for that perfect mix of classic...	3 beds \| 2 baths \| 1,001 sq.ft.	$650,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 1.99% Airbnb Rental Income: $2373 Traditional Rental Income: $3196 Airbnb ROI: -0.33% Traditional ROI: 1.99%
706 Judd Street Fairfield, CT Custom New Construction home boasting sophisticated & timeless design in the coveted Unive...	5 beds \| 6 baths \| 4,150 sq.ft.	$1,849,000	Airbnb cash on cash: -2.17% Traditional cash on cash: 2.7% Airbnb Rental Income: $2322 Traditional Rental Income: $10111 Airbnb ROI: -2.17% Traditional ROI: 2.7%
260 Range Road Fairfield, CT Located on a quiet cul-de-sac in one of Southport's premier family neighborhoods, this ele...	4 beds \| 4 baths \| 4,950 sq.ft.	$1,900,000	Airbnb cash on cash: -1.37% Traditional cash on cash: 0.66% Airbnb Rental Income: $4099 Traditional Rental Income: $6807 Airbnb ROI: -1.37% Traditional ROI: 0.66%
11 Twin Brooks Lane Fairfield, CT Opportunity Knocks for this perfect opportunity for renovation or expansion in prime Locat...	3 beds \| 3 baths \| 1,586 sq.ft.	$699,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 4.18% Airbnb Rental Income: $2373 Traditional Rental Income: $4858 Airbnb ROI: -0.52% Traditional ROI: 4.18%
17 Benson Place Fairfield, CT Experience luxury coastal living in this stunning 4-5 bedroom, 5 bath masterpiece nestled ...	5 beds \| 5 baths \| 3,086 sq.ft.	$2,299,000	Airbnb cash on cash: -2.36% Traditional cash on cash: 0.49% Airbnb Rental Income: $2322 Traditional Rental Income: $7814 Airbnb ROI: -2.36% Traditional ROI: 0.49%
68 Hawthorne Drive Fairfield, CT Welcome to this charming ranch-style home nestled on a spacious 1/2-acre lot in the highly...	3 beds \| 3 baths \| 2,800 sq.ft.	$829,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 3.26% Airbnb Rental Income: $2373 Traditional Rental Income: $5028 Airbnb ROI: -0.93% Traditional ROI: 3.26%
750 Burr Street Fairfield, CT Lions Gate: No need to move to the south of France as this extraordinary residence is righ...	5 beds \| 8 baths \| 6,414 sq.ft.	$3,300,000	Airbnb cash on cash: -2.59% Traditional cash on cash: 0.45% Airbnb Rental Income: $2322 Traditional Rental Income: $11048 Airbnb ROI: -2.59% Traditional ROI: 0.45%
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%
3657 Park Avenue Fairfield, CT Back on the market as of August 22,2025.This Ranch has over $720,000 spent transforming th...	3 beds \| 3 baths \| 3,208 sq.ft.	$999,999	Airbnb cash on cash: -1.31% Traditional cash on cash: 1.94% Airbnb Rental Income: $2373 Traditional Rental Income: $4812 Airbnb ROI: -1.31% Traditional ROI: 1.94%
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%
2821 Congress Street Fairfield, CT Located in the heart of Greenfield Hill, "Upper Meadow Farm" is a rare blend of timeless c...	5 beds \| 5 baths \| 3,703 sq.ft.	$2,650,000	Airbnb cash on cash: -2.46% Traditional cash on cash: 0.43% Airbnb Rental Income: $2322 Traditional Rental Income: $8841 Airbnb ROI: -2.46% Traditional ROI: 0.43%
155 MOODY Avenue Fairfield, CT WELCOME HOME! Step inside and feel the warmth of family life in the eat-in kitchen, where ...	3 beds \| 2 baths \| 1,510 sq.ft.	$520,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 3.97% Airbnb Rental Income: $2373 Traditional Rental Income: $3538 Airbnb ROI: 0.37% Traditional ROI: 3.97%
1477 Mill Plain Road Fairfield, CT *HIGHEST AND BEST OFFER SUBMISSION BY FRIDAY 8/22 12:00 PM Welcome to 1477 Mill Plain Ro...	4 beds \| 3 baths \| 2,550 sq.ft.	$1,299,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 1.19% Airbnb Rental Income: $4099 Traditional Rental Income: $5308 Airbnb ROI: -0.53% Traditional ROI: 1.19%
164 Tanglewood Lane Fairfield, CT This charming property located on a cul de sac in desired Greenfield Hills offers a fantas...	4 beds \| 3 baths \| 2,170 sq.ft.	$899,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 2.29% Airbnb Rental Income: $4099 Traditional Rental Income: $4630 Airbnb ROI: 0.62% Traditional ROI: 2.29%
647 Bronson Road Fairfield, CT First Time on the Market - A Southport Treasure with Endless Possibilities For the first ...	4 beds \| 3 baths \| 2,644 sq.ft.	$1,000,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 2.6% Airbnb Rental Income: $4099 Traditional Rental Income: $5422 Airbnb ROI: 0.24% Traditional ROI: 2.6%
260 Birch Road Fairfield, CT Experience Coastal Luxury in this Brand New Custom Colonial just steps away from the sooth...	4 beds \| 3 baths \| 3,157 sq.ft.	$2,349,000	Airbnb cash on cash: -1.69% Traditional cash on cash: -0.83% Airbnb Rental Income: $4099 Traditional Rental Income: $5100 Airbnb ROI: -1.69% Traditional ROI: -0.83%
73 Old Dam Road Fairfield, CT Set in one of Fairfield's most beloved waterfront communities, 73 Old Dam Rd is the perfec...	4 beds \| 3 baths \| 2,234 sq.ft.	$1,725,000	Airbnb cash on cash: -1.17% Traditional cash on cash: -0.22% Airbnb Rental Income: $4099 Traditional Rental Income: $4760 Airbnb ROI: -1.17% Traditional ROI: -0.22%
121 Longdean Road Fairfield, CT 2 bedroom 1 bathroom ranch located on a quiet cul-de-sac in the Sasco Hill area of Fairfie...	2 beds \| 1 baths \| 1,072 sq.ft.	$700,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 0.55% Airbnb Rental Income: $2828 Traditional Rental Income: $2490 Airbnb ROI: 0.05% Traditional ROI: 0.55%
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%
2180 Cross Highway Fairfield, CT Discover the ease of one-level living at 2180 Cross Highway, perfectly situated in a conve...	3 beds \| 2 baths \| 1,914 sq.ft.	$950,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 1.01% Airbnb Rental Income: $2373 Traditional Rental Income: $3752 Airbnb ROI: -1.21% Traditional ROI: 1.01%
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.	$2,000,000	Airbnb cash on cash: -1.44% Traditional cash on cash: -0.97% Airbnb Rental Income: $4099 Traditional Rental Income: $4115 Airbnb ROI: -1.44% Traditional ROI: -0.97%
109 Green Acre Lane Fairfield, CT Stunning Ranch on nearly a 1/2 acre in a coveted University neighborhood on park like grou...	3 beds \| 3 baths \| 1,980 sq.ft.	$864,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 2.21% Airbnb Rental Income: $2373 Traditional Rental Income: $4387 Airbnb ROI: -1.02% Traditional ROI: 2.21%
153 Pease Avenue Fairfield, CT Newly Renovated Colonial in Prime Southport Location. Beautifully updated colonial offerin...	4 beds \| 3 baths \| 3,597 sq.ft.	$1,545,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 0.4% Airbnb Rental Income: $4099 Traditional Rental Income: $5159 Airbnb ROI: -0.95% Traditional ROI: 0.4%
893 Church Hill Road Fairfield, CT After 54 years of cherished memories, this home is ready for you to make it your own! In S...	4 beds \| 2 baths \| 2,210 sq.ft.	$899,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 1.65% Airbnb Rental Income: $4099 Traditional Rental Income: $4092 Airbnb ROI: 0.62% Traditional ROI: 1.65%

Your search for investment property begins and ends here

Single Family Homes for Sale in Fairfield, CT

125 Vesper Street

Fairfield, CT

3 beds | 2 baths | 1,896 sq.ft.

$625,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $2373

Traditional Rental Income: $3753

Airbnb ROI: 0.77%

Traditional ROI: 4.14%

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%

91 Henderson Road

Fairfield, CT

3 beds | 3 baths | 1,662 sq.ft.

$799,000

Airbnb cash on cash: 0.32%

Traditional cash on cash: 3.42%

Airbnb Rental Income: $2373

Traditional Rental Income: $4093

Airbnb ROI: 0.32%

Traditional ROI: 3.42%

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%

161 Brion Drive

Fairfield, CT

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

$400,000

Airbnb cash on cash: 1.54%

Traditional cash on cash: 7.53%

Airbnb Rental Income: $2373

Traditional Rental Income: $4035

Airbnb ROI: 1.54%

Traditional ROI: 7.53%

450 Penfield Road

Fairfield, CT

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

$3,100,000

Airbnb cash on cash: -0.89%

Traditional cash on cash: -0.15%

Airbnb Rental Income: $2322

Traditional Rental Income: $3859

Airbnb ROI: -0.89%

Traditional ROI: -0.15%

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%

72 Lloyd Drive

Fairfield, CT

5 beds | 5 baths | 4,038 sq.ft.

$1,625,000

Airbnb cash on cash: -2.04%

Traditional cash on cash: -1.08%

Airbnb Rental Income: $2322

Traditional Rental Income: $3187

Airbnb ROI: -2.04%