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
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: -1.76% Traditional cash on cash: 1.16% Airbnb Rental Income: $1694 Traditional Rental Income: $3648 Airbnb ROI: -1.76% 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.	$1,149,900	Airbnb cash on cash: 0.07% Traditional cash on cash: 5.98% Airbnb Rental Income: $2624 Traditional Rental Income: $8321 Airbnb ROI: 0.07% Traditional ROI: 5.98%
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.	$1,500,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 1.68% Airbnb Rental Income: $4041 Traditional Rental Income: $5572 Airbnb ROI: -0.04% Traditional ROI: 1.68%
154 Wilburs Lane Guilford, CT Welcome to 154 Wilbur Ln, a truly distinctive property that sets itself apart from the res...	5 beds \| 2 baths \| 3,629 sq.ft.	$640,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 3.83% Airbnb Rental Income: $4041 Traditional Rental Income: $4015 Airbnb ROI: 2.43% Traditional ROI: 3.83%
448 Lake Drive Guilford, CT A Rare Opportunity on Lake Quonnipaug Experience waterfront living at its finest with this...	4 beds \| 4 baths \| 3,504 sq.ft.	$1,395,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 3.38% Airbnb Rental Income: $2624 Traditional Rental Income: $7047 Airbnb ROI: -0.52% Traditional ROI: 3.38%
51 Andrews Road Guilford, CT Exceptional Contemporary Direct Waterfront Estate. Located in Guilford, CT, on a private c...	4 beds \| 4 baths \| 5,640 sq.ft.	$5,000,000	Airbnb cash on cash: -1.83% Traditional cash on cash: -0.66% Airbnb Rental Income: $2624 Traditional Rental Income: $7444 Airbnb ROI: -1.83% Traditional ROI: -0.66%
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: -0.02% Traditional cash on cash: 3.03% Airbnb Rental Income: $2624 Traditional Rental Income: $5390 Airbnb ROI: -0.02% Traditional ROI: 3.03%
294 Church Street Guilford, CT Mixed-use zoning (convertible to full commercial or multi unit with town permits) 2,005 sq...	3 beds \| 2 baths \| 1,672 sq.ft.	$712,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 2.21% Airbnb Rental Income: $1694 Traditional Rental Income: $2920 Airbnb ROI: -0.35% Traditional ROI: 2.21%
409 Boston Street Guilford, CT Rare opportunity in desirable Guilford. This 9 room, 3-bedroom, 2-bath Raised Ranch sits o...	4 beds \| 2 baths \| 1,236 sq.ft.	$300,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 7.61% Airbnb Rental Income: $2624 Traditional Rental Income: $3276 Airbnb ROI: 3.08% Traditional ROI: 7.61%
19 Polpis Lane #19 Guilford, CT Private Pet friendly End unit newly refreshed! Ranch style offers Cathedral Ceiling Living...	1 beds \| 1 baths \| 839 sq.ft.	$225,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 2.7% Airbnb Rental Income: $1115 Traditional Rental Income: $1501 Airbnb ROI: -0.87% Traditional ROI: 2.7%
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: -1.08% Traditional cash on cash: 1.34% Airbnb Rental Income: $2624 Traditional Rental Income: $4247 Airbnb ROI: -1.08% Traditional ROI: 1.34%
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: -1.33% Traditional cash on cash: 1.59% Airbnb Rental Income: $1694 Traditional Rental Income: $3927 Airbnb ROI: -1.33% Traditional ROI: 1.59%
401 Three Corners Road Guilford, CT Just minutes to downtown Guilford, this striking 4 bedroom contemporary offers exceptional...	3 beds \| 3 baths \| 2,806 sq.ft.	$899,900	Airbnb cash on cash: -0.92% Traditional cash on cash: 3.13% Airbnb Rental Income: $1694 Traditional Rental Income: $4619 Airbnb ROI: -0.92% Traditional ROI: 3.13%
106 Sconset Lane Guilford, CT Welcome to easy, one-floor living in a home that has been lovingly cared for inside and ou...	2 beds \| 2 baths \| 1,940 sq.ft.	$624,900	Airbnb cash on cash: -1.83% Traditional cash on cash: 1.97% Airbnb Rental Income: $895 Traditional Rental Income: $2771 Airbnb ROI: -1.83% Traditional ROI: 1.97%
66 High Street #47 Guilford, CT The Residences at 66 High Street provide a unique offering. An enclave of luxury condomini...	2 beds \| 2 baths \| 2,033 sq.ft.	$1,275,000	Airbnb cash on cash: -2.36% Traditional cash on cash: 0.87% Airbnb Rental Income: $895 Traditional Rental Income: $4385 Airbnb ROI: -2.36% Traditional ROI: 0.87%
274 Church Street #3D Guilford, CT Looking to live close to downtown Guilford, with all the ease of condo life? Look no furth...	2 beds \| 2 baths \| 1,180 sq.ft.	$299,900	Airbnb cash on cash: -0.6% Traditional cash on cash: 5.28% Airbnb Rental Income: $895 Traditional Rental Income: $2217 Airbnb ROI: -0.6% Traditional ROI: 5.28%
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.	$549,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 3.83% Airbnb Rental Income: $1694 Traditional Rental Income: $3205 Airbnb ROI: -0.03% Traditional ROI: 3.83%
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.	$1,700,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 2.93% Airbnb Rental Income: $2624 Traditional Rental Income: $6510 Airbnb ROI: 0.07% Traditional ROI: 2.93%
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: -0.63% Traditional cash on cash: 3.91% Airbnb Rental Income: $2624 Traditional Rental Income: $6228 Airbnb ROI: -0.63% Traditional ROI: 3.91%
110 Edgewood Drive Guilford, CT Meticulously maintained with attention to detail this builder's own home is not to be miss...	3 beds \| 2 baths \| 2,191 sq.ft.	$625,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 3.29% Airbnb Rental Income: $1694 Traditional Rental Income: $3335 Airbnb ROI: -0.33% Traditional ROI: 3.29%
200 Whitfield Street Guilford, CT Possibly the most admired of the historic homes closeby to the storied Guilford Town Green...	4 beds \| 4 baths \| 3,754 sq.ft.	$2,175,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 0.98% Airbnb Rental Income: $2624 Traditional Rental Income: $6415 Airbnb ROI: -1.21% Traditional ROI: 0.98%
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.	$779,000	Airbnb cash on cash: -1.06% Traditional cash on cash: -0.06% Airbnb Rental Income: $1115 Traditional Rental Income: $1472 Airbnb ROI: -1.06% Traditional ROI: -0.06%

Real Estate investment in Guilford, CT

There are 32 properties for sale in the city of Guilford . The median list price in Guilford is $899,900 and the average price per square foot is $353. In May 2026, the average monthly cash on cash return in Guilford is 3.00%. The average monthly rental income in Guilford is $4,015.

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

There are 32 investment properties available for sale in Guilford.

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

The ROI for Long-Term is higher than the Short-Term in Guilford with average rental income of $4,015.

Your search for investment property begins and ends here

Investment Property for Sale in Guilford, CT

874 Nut Plains Road lot: 2 - Style A

Guilford, CT

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

$889,900

Airbnb cash on cash: -1.76%

Traditional cash on cash: 1.16%

Airbnb Rental Income: $1694

Traditional Rental Income: $3648

Airbnb ROI: -1.76%

Traditional ROI: 1.16%

1607 Great Hill Road

Guilford, CT

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

$1,149,900

Airbnb cash on cash: 0.07%

Traditional cash on cash: 5.98%

Airbnb Rental Income: $2624

Traditional Rental Income: $8321

Airbnb ROI: 0.07%

Traditional ROI: 5.98%

7 Caleb Court

Guilford, CT

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

$1,500,000

Airbnb cash on cash: -0.04%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $4041

Traditional Rental Income: $5572

Airbnb ROI: -0.04%

Traditional ROI: 1.68%

154 Wilburs Lane

Guilford, CT

5 beds | 2 baths | 3,629 sq.ft.

$640,000

Airbnb cash on cash: 2.43%

Traditional cash on cash: 3.83%

Airbnb Rental Income: $4041

Traditional Rental Income: $4015

Airbnb ROI: 2.43%

Traditional ROI: 3.83%

448 Lake Drive

Guilford, CT

4 beds | 4 baths | 3,504 sq.ft.

$1,395,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $2624

Traditional Rental Income: $7047

Airbnb ROI: -0.52%

Traditional ROI: 3.38%

51 Andrews Road

Guilford, CT

4 beds | 4 baths | 5,640 sq.ft.

$5,000,000

Airbnb cash on cash: -1.83%

Traditional cash on cash: -0.66%

Airbnb Rental Income: $2624

Traditional Rental Income: $7444

Airbnb ROI: -1.83%

Traditional ROI: -0.66%

51 Pearl Street

Guilford, CT

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

$1,195,000

Airbnb cash on cash: -0.02%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $2624

Traditional Rental Income: $5390

Airbnb ROI: -0.02%

Traditional ROI: 3.03%

294 Church Street

Guilford, CT

3 beds | 2 baths | 1,672 sq.ft.

$712,000

Airbnb cash on cash: -0.35%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $1694

Traditional Rental Income: $2920

Airbnb ROI: -0.35%