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
330 Foxwood Road Guilford, CT Set on a serene .92-acre lot in one of Guilford's most desirable neighborhoods, this impec...	3 beds \| 3 baths \| 2,220 sq.ft.	$795,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 3.68% Airbnb Rental Income: $2506 Traditional Rental Income: $4309 Airbnb ROI: 0.42% Traditional ROI: 3.68%
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: -0.95% Traditional cash on cash: 1.16% Airbnb Rental Income: $2506 Traditional Rental Income: $3648 Airbnb ROI: -0.95% Traditional ROI: 1.16%
195 Tanner Marsh Road Guilford, CT Masterfully crafted NEW CONSTRUCTION meticulously designed with unparalleled attention to ...	4 beds \| 4 baths \| 3,030 sq.ft.	$1,385,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 0.6% Airbnb Rental Income: $3191 Traditional Rental Income: $4893 Airbnb ROI: -1.28% Traditional ROI: 0.6%
0 Tamarack Lane #Lot 23 Guilford, CT Last two homesites available in desirable Long Hill Estates. This is your chance to own NE...	3 beds \| 3 baths \| 2,075 sq.ft.	$689,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 2.17% Airbnb Rental Income: $2506 Traditional Rental Income: $3499 Airbnb ROI: -0.31% Traditional ROI: 2.17%
0 Tamarack Lane #Lot 19 Guilford, CT Last two homesites in desirable Long Hill Estates. This is your chance to own new construc...	3 beds \| 3 baths \| 1,708 sq.ft.	$664,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 2.21% Airbnb Rental Income: $2506 Traditional Rental Income: $3395 Airbnb ROI: -0.21% Traditional ROI: 2.21%
55 Harbor View Road Guilford, CT Charming Waterfront Community Opportunity - Bring Your Vision! Welcome to 55 Harbor View R...	3 beds \| 3 baths \| 1,772 sq.ft.	$729,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 3.16% Airbnb Rental Income: $2506 Traditional Rental Income: $4394 Airbnb ROI: -0.51% Traditional ROI: 3.16%
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.	$665,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 3.2% Airbnb Rental Income: $3633 Traditional Rental Income: $4015 Airbnb ROI: 1.3% Traditional ROI: 3.2%
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: -1.3% Traditional cash on cash: 2.23% Airbnb Rental Income: $3191 Traditional Rental Income: $7047 Airbnb ROI: -1.3% Traditional ROI: 2.23%
599 Goose Lane Guilford, CT Newly painted throughout! Discover the perfect blend of comfort and convenience in this su...	3 beds \| 2 baths \| 1,300 sq.ft.	$539,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 2.18% Airbnb Rental Income: $2506 Traditional Rental Income: $2762 Airbnb ROI: 0.46% Traditional ROI: 2.18%
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.	$1,225,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 1.52% Airbnb Rental Income: $3191 Traditional Rental Income: $5390 Airbnb ROI: -1.04% Traditional ROI: 1.52%
76 Sachem Head Road Guilford, CT Resort-like gated estate perched high above Sachem Head Road overlooking a saltwater tidal...	4 beds \| 5 baths \| 5,620 sq.ft.	$2,950,000	Airbnb cash on cash: -2.26% Traditional cash on cash: 0.07% Airbnb Rental Income: $3191 Traditional Rental Income: $8848 Airbnb ROI: -2.26% Traditional ROI: 0.07%
120 North Fair Street #2C Guilford, CT Downtown Guilford ranch living like you HAVE NEVER SEEN! This 2,500+ sq ft condo is stunni...	2 beds \| 3 baths \| 2,524 sq.ft.	$1,300,000	Airbnb cash on cash: -3.49% Traditional cash on cash: -0.49% Airbnb Rental Income: $1070 Traditional Rental Income: $4326 Airbnb ROI: -3.49% Traditional ROI: -0.49%
288 Jefferson Drive Guilford, CT Welcome to 288 Jefferson Drive! A charming, custom-built ranch style home located on a spa...	2 beds \| 2 baths \| 2,597 sq.ft.	$615,000	Airbnb cash on cash: -2.06% Traditional cash on cash: 1.72% Airbnb Rental Income: $1070 Traditional Rental Income: $2876 Airbnb ROI: -2.06% Traditional ROI: 1.72%
214 Nortontown Road Guilford, CT Welcome to your private sanctuary in the historic town of Guilford. A timeless country est...	5 beds \| 5 baths \| 4,829 sq.ft.	$1,245,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 4.01% Airbnb Rental Income: $3633 Traditional Rental Income: $8354 Airbnb ROI: -0.76% Traditional ROI: 4.01%
52 Fair Street Guilford, CT Built in 1770, this gracious house has been a prominent presence on Fair Street since it w...	5 beds \| 3 baths \| 2,744 sq.ft.	$1,450,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 0.34% Airbnb Rental Income: $3633 Traditional Rental Income: $4774 Airbnb ROI: -1.09% Traditional ROI: 0.34%
75 Hart Road Guilford, CT Situated on over 2 acres of private, wooded, park-like grounds, this spacious Split Level ...	3 beds \| 3 baths \| 1,725 sq.ft.	$474,900	Airbnb cash on cash: 0.94% Traditional cash on cash: 4.26% Airbnb Rental Income: $2506 Traditional Rental Income: $3372 Airbnb ROI: 0.94% Traditional ROI: 4.26%
26 Water Street Guilford, CT LOCATION! LOCATION! LOCATION! Welcome to this beautifully fully remodeled two-family home ...	4 beds \| 2 baths \| 1,804 sq.ft.	$799,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 1.94% Airbnb Rental Income: $3191 Traditional Rental Income: $3863 Airbnb ROI: 0.07% Traditional ROI: 1.94%

Real Estate investment in Guilford, CT

There are 23 properties for sale in the city of Guilford . The median list price in Guilford is $775,000 and the average price per square foot is $298. In December 2025, the average monthly cash on cash return in Guilford is 2.00%. The average monthly rental income in Guilford is $3,939.

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

There are 23 investment properties available for sale in Guilford.

In 2025, 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 $3,939.

Your search for investment property begins and ends here

Investment Property for Sale in Guilford, CT

330 Foxwood Road

Guilford, CT

3 beds | 3 baths | 2,220 sq.ft.

$795,000

Airbnb cash on cash: 0.42%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $2506

Traditional Rental Income: $4309

Airbnb ROI: 0.42%

Traditional ROI: 3.68%

874 Nut Plains Road #Lot 2 - Style A

Guilford, CT

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

$889,900

Airbnb cash on cash: -0.95%

Traditional cash on cash: 1.16%

Airbnb Rental Income: $2506

Traditional Rental Income: $3648

Airbnb ROI: -0.95%

Traditional ROI: 1.16%

195 Tanner Marsh Road

Guilford, CT

4 beds | 4 baths | 3,030 sq.ft.

$1,385,000

Airbnb cash on cash: -1.28%

Traditional cash on cash: 0.6%

Airbnb Rental Income: $3191

Traditional Rental Income: $4893

Airbnb ROI: -1.28%

Traditional ROI: 0.6%

0 Tamarack Lane #Lot 23

Guilford, CT

3 beds | 3 baths | 2,075 sq.ft.

$689,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $2506

Traditional Rental Income: $3499

Airbnb ROI: -0.31%

Traditional ROI: 2.17%

0 Tamarack Lane #Lot 19

Guilford, CT

3 beds | 3 baths | 1,708 sq.ft.

$664,000

Airbnb cash on cash: -0.21%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $2506

Traditional Rental Income: $3395

Airbnb ROI: -0.21%

Traditional ROI: 2.21%

55 Harbor View Road

Guilford, CT

3 beds | 3 baths | 1,772 sq.ft.

$729,000

Airbnb cash on cash: -0.51%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $2506

Traditional Rental Income: $4394

Airbnb ROI: -0.51%

Traditional ROI: 3.16%

154 Wilburs Lane

Guilford, CT

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

$665,000

Airbnb cash on cash: 1.3%

Traditional cash on cash: 3.2%

Airbnb Rental Income: $3633

Traditional Rental Income: $4015

Airbnb ROI: 1.3%

Traditional ROI: 3.2%

448 Lake Drive

Guilford, CT

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

$1,395,000

Airbnb cash on cash: -1.3%

Traditional cash on cash: 2.23%

Airbnb Rental Income: $3191

Traditional Rental Income: $7047

Airbnb ROI: -1.3%