Real Estate Investment Properties for Sale in Guilford, CT

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

Explore a variety of short-term homes & houses in Guilford, CT. Invest wisely with VRBO & Guilford, 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 Guilford, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
181 Wilderwood Drive Guilford, CT Privately sited on 2.38 acres along a quiet cul-de-sac, this charming Cape offers a rare o...	4 beds \| 2 baths \| 1,426 sq.ft.	$575,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 3.28% Airbnb Rental Income: $2764 Traditional Rental Income: $3099 Airbnb ROI: 1.45% Traditional ROI: 3.28%
1640 Little Meadow Road Guilford, CT Historic Charm, Modern Living - On 3+ Acres in Guilford If you've been searching for somet...	5 beds \| 3 baths \| 2,879 sq.ft.	$1,100,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 2.78% Airbnb Rental Income: $4578 Traditional Rental Income: $4901 Airbnb ROI: 1.54% Traditional ROI: 2.78%
66 High Street #17 Guilford, CT Welcome to a truly exceptional living experience at The Residences at 66 High Street! This...	3 beds \| 3 baths \| 3,348 sq.ft.	$2,990,000	Airbnb cash on cash: -2.18% Traditional cash on cash: -1.51% Airbnb Rental Income: $2478 Traditional Rental Income: $3760 Airbnb ROI: -2.18% Traditional ROI: -1.51%
874 Nut Plains Road lot: 2 - Style A Guilford, CT Introducing an exquisite gem nestled just a couple miles from our charming Town Green - th...	3 beds \| 3 baths \| 2,568 sq.ft.	$889,900	Airbnb cash on cash: -0.98% Traditional cash on cash: 1.16% Airbnb Rental Income: $2478 Traditional Rental Income: $3648 Airbnb ROI: -0.98% Traditional ROI: 1.16%
1607 Great Hill Road Guilford, CT Own your own little oasis! Set back in the woods of guilford on 3.5 acres you have a ton o...	4 beds \| 5 baths \| 3,220 sq.ft.	$999,999	Airbnb cash on cash: 0.35% Traditional cash on cash: 7.02% Airbnb Rental Income: $2764 Traditional Rental Income: $8321 Airbnb ROI: 0.35% Traditional ROI: 7.02%
7 Caleb Court Guilford, CT Absolutely stunning 5+ bedroom light-filled home offers the perfect blend of elegance & mo...	5 beds \| 5 baths \| 5,310 sq.ft.	$1,395,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 1.88% Airbnb Rental Income: $4578 Traditional Rental Income: $5572 Airbnb ROI: 0.38% Traditional ROI: 1.88%
51 Pearl Street Guilford, CT Rare opportunity in Guilford! This home is currently used as a multifamily but can revert ...	4 beds \| 4 baths \| 2,392 sq.ft.	$1,195,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 3.03% Airbnb Rental Income: $2764 Traditional Rental Income: $5390 Airbnb ROI: 0.08% Traditional ROI: 3.03%
76 Sachem Head Road Guilford, CT Welcome to your private coastal sanctuary in the prestigious Sachem Head area of Guilford....	4 beds \| 5 baths \| 5,620 sq.ft.	$2,799,999	Airbnb cash on cash: -1.19% Traditional cash on cash: 1.4% Airbnb Rental Income: $2764 Traditional Rental Income: $8848 Airbnb ROI: -1.19% Traditional ROI: 1.4%
294 Church Street Guilford, CT Mixed-use property (convertible to full commercial or multi unit with town permits) 2,005 ...	3 beds \| 2 baths \| 1,672 sq.ft.	$712,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 2.21% Airbnb Rental Income: $2478 Traditional Rental Income: $2920 Airbnb ROI: 0.63% Traditional ROI: 2.21%
876 Nut Plains Road Guilford, CT Custom Built Farmhouse Style Colonial perched on high with professional landscaped lot. Hi...	4 beds \| 3 baths \| 2,648 sq.ft.	$1,000,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 1.34% Airbnb Rental Income: $2764 Traditional Rental Income: $4247 Airbnb ROI: -0.96% Traditional ROI: 1.34%
148 Highwoods Drive Guilford, CT Welcome to 148 Highwoods Drive in Guilford-a beautifully maintained 4-bedroom, 2-bath home...	4 beds \| 2 baths \| 2,236 sq.ft.	$615,000	Airbnb cash on cash: 1.24% Traditional cash on cash: 3.58% Airbnb Rental Income: $2764 Traditional Rental Income: $3457 Airbnb ROI: 1.24% Traditional ROI: 3.58%
1800 Moose Hill Road Guilford, CT Where gardens flourish and privacy surrounds you, this Moose Hill retreat offers a lifesty...	3 beds \| 3 baths \| 3,939 sq.ft.	$995,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 1.59% Airbnb Rental Income: $2478 Traditional Rental Income: $3927 Airbnb ROI: -0.63% Traditional ROI: 1.59%
737 Leetes Island Road Guilford, CT Welcome to 737 Leetes Island Road, a stone's throw from Shell Beach, one of Guilford's mos...	3 beds \| 2 baths \| 1,344 sq.ft.	$519,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 4.11% Airbnb Rental Income: $2478 Traditional Rental Income: $3205 Airbnb ROI: 1.37% Traditional ROI: 4.11%
539A Boston Street Guilford, CT Brand NEW CONSTRUCTION. Move in Ready! This modern, luxurious 3284sf, 4-bedroom, 3.5-bathr...	4 beds \| 4 baths \| 3,284 sq.ft.	$1,650,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 3.05% Airbnb Rental Income: $2764 Traditional Rental Income: $6510 Airbnb ROI: 0.18% Traditional ROI: 3.05%
48 State Street Guilford, CT The Nathaniel Hall House (c. 1770) offers the perfect canvas for restoration to a prestigi...	4 beds \| 4 baths \| 3,402 sq.ft.	$1,000,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.91% Airbnb Rental Income: $2764 Traditional Rental Income: $6228 Airbnb ROI: -0.51% Traditional ROI: 3.91%
217 Stonehedge Lane Guilford, CT WELCOME to 217 Stonehedge Lane, a beautifully updated retreat set on nearly an acre where ...	4 beds \| 3 baths \| 1,954 sq.ft.	$699,900	Airbnb cash on cash: 0.75% Traditional cash on cash: 3.24% Airbnb Rental Income: $2764 Traditional Rental Income: $3744 Airbnb ROI: 0.75% Traditional ROI: 3.24%
446 Whitfield Street #C Guilford, CT A rare opportunity to own one of downtown Guilford's most iconic residences, often referre...	1 beds \| 2 baths \| 1,672 sq.ft.	$699,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 2.24% Airbnb Rental Income: $1282 Traditional Rental Income: $2901 Airbnb ROI: -0.86% Traditional ROI: 2.24%
31 River Colony Guilford, CT Welcome to 31 River Colony, a cozy and inviting first-floor ranch-style condo with one bed...	1 beds \| 1 baths \| 605 sq.ft.	$259,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 6.47% Airbnb Rental Income: $1282 Traditional Rental Income: $2144 Airbnb ROI: 1.29% Traditional ROI: 6.47%
83 Jacobs Lane Guilford, CT Nestled high on a quiet, highly private 2-acre hilltop lot, 83 Jacobs Lane offers a rare b...	3 beds \| 4 baths \| 3,031 sq.ft.	$1,000,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 5.01% Airbnb Rental Income: $2478 Traditional Rental Income: $6679 Airbnb ROI: -0.15% Traditional ROI: 5.01%
208 Boston Street Guilford, CT Shoreline charm meets unlimited potential at 208 Boston Street. This quintessential New En...	3 beds \| 3 baths \| 2,052 sq.ft.	$649,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 4.34% Airbnb Rental Income: $2478 Traditional Rental Income: $4149 Airbnb ROI: 0.58% Traditional ROI: 4.34%
51 Wimler Lane Guilford, CT Welcome to Waystone Farm, an award-winning, energy-efficient gentleman's farm and potentia...	4 beds \| 4 baths \| 2,762 sq.ft.	$1,825,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 1.22% Airbnb Rental Income: $2764 Traditional Rental Income: $5279 Airbnb ROI: -0.64% Traditional ROI: 1.22%
86 State Street Guilford, CT Incredibly Rare Opportunity in the Heart of Guilford! Located just moments from the Guilfo...	2 beds \| 2 baths \| 1,525 sq.ft.	$465,000	Airbnb cash on cash: -1.05% Traditional cash on cash: 4.12% Airbnb Rental Income: $1464 Traditional Rental Income: $3281 Airbnb ROI: -1.05% Traditional ROI: 4.12%
33 Church Street Guilford, CT The George W. Seward House - Circa 1888 A rare opportunity to own a piece of Guilford hist...	7 beds \| 4 baths \| 3,833 sq.ft.	$1,185,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 3.74% Airbnb Rental Income: $4578 Traditional Rental Income: $6492 Airbnb ROI: 1.14% Traditional ROI: 3.74%
57 Faulkner Drive Guilford, CT Custom built with exceptional craftsmanship and attention to detail, this stunning coastal...	3 beds \| 3 baths \| 2,891 sq.ft.	$3,300,000	Airbnb cash on cash: -0.94% Traditional cash on cash: -0.08% Airbnb Rental Income: $2478 Traditional Rental Income: $4527 Airbnb ROI: -0.94% Traditional ROI: -0.08%
620 Colonial Road Guilford, CT This is not simply waterfront living. This is a waterfront lifestyle unlike any other. Tuc...	4 beds \| 5 baths \| 5,475 sq.ft.	$7,500,000	Airbnb cash on cash: -1.58% Traditional cash on cash: -0.55% Airbnb Rental Income: $2764 Traditional Rental Income: $9264 Airbnb ROI: -1.58% Traditional ROI: -0.55%
216 Bluff View Drive Guilford, CT Bluff Head Estates! Picture your perfect summer evening: pool lights glowing, a warm breez...	4 beds \| 3 baths \| 3,410 sq.ft.	$825,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 3.48% Airbnb Rental Income: $2764 Traditional Rental Income: $4748 Airbnb ROI: 0.06% Traditional ROI: 3.48%

Real Estate investment in Guilford, CT

There are 36 properties for sale in the city of Guilford . The median list price in Guilford is $969,000 and the average price per square foot is $346. In June 2026, the average monthly cash on cash return in Guilford is 3.00%. The average monthly rental income in Guilford is $4,482.

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

There are 36 investment properties available for sale in Guilford.

In 2026, the best neighborhood to buy investment property is Guilford.

The ROI for Short-Term is higher than the Long-Term in Guilford with average rental income of $2,764.

Your search for investment property begins and ends here

Investment Property for Sale in Guilford, CT

181 Wilderwood Drive

Guilford, CT

4 beds | 2 baths | 1,426 sq.ft.

$575,000

Airbnb cash on cash: 1.45%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $2764

Traditional Rental Income: $3099

Airbnb ROI: 1.45%

Traditional ROI: 3.28%

1640 Little Meadow Road

Guilford, CT

5 beds | 3 baths | 2,879 sq.ft.

$1,100,000

Airbnb cash on cash: 1.54%

Traditional cash on cash: 2.78%

Airbnb Rental Income: $4578

Traditional Rental Income: $4901

Airbnb ROI: 1.54%

Traditional ROI: 2.78%

66 High Street #17

Guilford, CT

3 beds | 3 baths | 3,348 sq.ft.

$2,990,000

Airbnb cash on cash: -2.18%

Traditional cash on cash: -1.51%

Airbnb Rental Income: $2478

Traditional Rental Income: $3760

Airbnb ROI: -2.18%

Traditional ROI: -1.51%

874 Nut Plains Road lot: 2 - Style A

Guilford, CT

3 beds | 3 baths | 2,568 sq.ft.

$889,900

Airbnb cash on cash: -0.98%

Traditional cash on cash: 1.16%

Airbnb Rental Income: $2478

Traditional Rental Income: $3648

Airbnb ROI: -0.98%

Traditional ROI: 1.16%

1607 Great Hill Road

Guilford, CT

4 beds | 5 baths | 3,220 sq.ft.

$999,999

Airbnb cash on cash: 0.35%

Traditional cash on cash: 7.02%

Airbnb Rental Income: $2764

Traditional Rental Income: $8321

Airbnb ROI: 0.35%

Traditional ROI: 7.02%

7 Caleb Court

Guilford, CT

5 beds | 5 baths | 5,310 sq.ft.

$1,395,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: 1.88%

Airbnb Rental Income: $4578

Traditional Rental Income: $5572

Airbnb ROI: 0.38%

Traditional ROI: 1.88%

51 Pearl Street

Guilford, CT

4 beds | 4 baths | 2,392 sq.ft.

$1,195,000

Airbnb cash on cash: 0.08%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $2764

Traditional Rental Income: $5390

Airbnb ROI: 0.08%

Traditional ROI: 3.03%

76 Sachem Head Road

Guilford, CT

4 beds | 5 baths | 5,620 sq.ft.

$2,799,999

Airbnb cash on cash: -1.19%

Traditional cash on cash: 1.4%

Airbnb Rental Income: $2764

Traditional Rental Income: $8848

Airbnb ROI: -1.19%