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
1640 Little Meadow Road Guilford, CT Coming soon..... Historic Charm, Modern Living - On 3+ Acres in Guilford If you've been se...	5 beds \| 3 baths \| 2,879 sq.ft.	$1,100,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 2.78% Airbnb Rental Income: $4833 Traditional Rental Income: $4901 Airbnb ROI: 1.75% Traditional ROI: 2.78%
405 Whitfield St #2 Guilford, CT Welcome to Eagleview, a brand new community of 12 Luxury Townhomes, located along the Gui...	6 beds \| 4 baths \| 6,216 sq.ft.	$3,995,000	Airbnb cash on cash: -2.27% Traditional cash on cash: -2.16% Airbnb Rental Income: $4833 Traditional Rental Income: $4239 Airbnb ROI: -2.27% Traditional ROI: -2.16%
66 High St #17 Guilford, CT Welcome to a truly exceptional living experience at The Residences at 66 High Street! This...	3 beds \| 2 baths \| 3,348 sq.ft.	$2,990,000	Airbnb cash on cash: -2.17% Traditional cash on cash: -1.51% Airbnb Rental Income: $2543 Traditional Rental Income: $3760 Airbnb ROI: -2.17% Traditional ROI: -1.51%
1500 Durham Road Guilford, CT Welcome to the Treehouse, a thoughtfully updated Mid-Century Modern home set high above 2....	4 beds \| 3 baths \| 2,414 sq.ft.	$635,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 3.28% Airbnb Rental Income: $3286 Traditional Rental Income: $3287 Airbnb ROI: 2.03% Traditional ROI: 3.28%
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: -0.91% Traditional cash on cash: 1.16% Airbnb Rental Income: $2543 Traditional Rental Income: $3648 Airbnb ROI: -0.91% 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.	$949,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 7.45% Airbnb Rental Income: $3286 Traditional Rental Income: $8321 Airbnb ROI: 0.92% Traditional ROI: 7.45%
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: 0.54% Traditional cash on cash: 1.88% Airbnb Rental Income: $4833 Traditional Rental Income: $5572 Airbnb ROI: 0.54% Traditional ROI: 1.88%
51 Pearl St 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.	$1,075,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 3.48% Airbnb Rental Income: $3286 Traditional Rental Income: $5390 Airbnb ROI: 0.64% Traditional ROI: 3.48%
66 High St #38 Guilford, CT This stunning luxury condominium seamlessly blends sophistication and comfort. Completely ...	3 beds \| 3 baths \| 2,983 sq.ft.	$2,995,000	Airbnb cash on cash: -3.19% Traditional cash on cash: -2.07% Airbnb Rental Income: $2543 Traditional Rental Income: $5040 Airbnb ROI: -3.19% Traditional ROI: -2.07%
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: -1.02% Traditional cash on cash: 1.4% Airbnb Rental Income: $3286 Traditional Rental Income: $8848 Airbnb ROI: -1.02% Traditional ROI: 1.4%
35 village Cir #35 Guilford, CT 35 village Cir #35, Guilford, CT 06437 \| Condo/Coop	2 beds \| 2 baths \| 2,625 sq.ft.	$889,900	Airbnb cash on cash: -2.28% Traditional cash on cash: -0.26% Airbnb Rental Income: $1716 Traditional Rental Income: $2917 Airbnb ROI: -2.28% Traditional ROI: -0.26%
294 Church St Guilford, CT Mixed-use property (convertible to full commercial or multi unit with town permits) 2,005 ...	3 beds \| 1 baths \| 1,672 sq.ft.	$711,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 2.21% Airbnb Rental Income: $2543 Traditional Rental Income: $2920 Airbnb ROI: 0.72% Traditional ROI: 2.21%
147 Boston St Guilford, CT 147 Boston St, Guilford, CT 06437 \| Single Family Residential	4 beds \| 2 baths \| 2,966 sq.ft.	$1,399,000	Airbnb cash on cash: -1.24% Traditional cash on cash: -0.41% Airbnb Rental Income: $3286 Traditional Rental Income: $3626 Airbnb ROI: -1.24% Traditional ROI: -0.41%
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: 0.72% Traditional cash on cash: 2.7% Airbnb Rental Income: $1522 Traditional Rental Income: $1501 Airbnb ROI: 0.72% Traditional ROI: 2.7%
2 Village Cir #2 Guilford, CT 2 Village Cir #2, Guilford, CT 06437 \| Condo/Coop	2 beds \| 2 baths \| 2,318 sq.ft.	$909,000	Airbnb cash on cash: -2.3% Traditional cash on cash: 0.05% Airbnb Rental Income: $1716 Traditional Rental Income: $3230 Airbnb ROI: -2.3% Traditional ROI: 0.05%
12 Village Cir #12 Guilford, CT 12 Village Cir #12, Guilford, CT 06437 \| Condo/Coop	2 beds \| 2 baths \| 2,197 sq.ft.	$889,900	Airbnb cash on cash: -2.28% Traditional cash on cash: 0.13% Airbnb Rental Income: $1716 Traditional Rental Income: $3236 Airbnb ROI: -2.28% Traditional ROI: 0.13%
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: -0.49% Traditional cash on cash: 1.34% Airbnb Rental Income: $3286 Traditional Rental Income: $4247 Airbnb ROI: -0.49% Traditional ROI: 1.34%
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: 1.48% Traditional cash on cash: 4.11% Airbnb Rental Income: $2543 Traditional Rental Income: $3205 Airbnb ROI: 1.48% Traditional ROI: 4.11%
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: -0.93% Traditional cash on cash: 0.98% Airbnb Rental Income: $3286 Traditional Rental Income: $6415 Airbnb ROI: -0.93% Traditional ROI: 0.98%
446 Whitfield St #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: -1.3% Traditional cash on cash: 1.49% Airbnb Rental Income: $1522 Traditional Rental Income: $2901 Airbnb ROI: -1.3% Traditional ROI: 1.49%
28 Walden Hill Road Guilford, CT A true once in a lifetime opportunity! As you wind through picturesque Sachem's Head onto ...	5 beds \| 7 baths \| 5,185 sq.ft.	$3,750,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 1.34% Airbnb Rental Income: $4833 Traditional Rental Income: $10898 Airbnb ROI: -0.69% Traditional ROI: 1.34%
168 Union Street Guilford, CT Rarely does a home of this caliber, offering both historical soul and "down-to-the-studs" ...	4 beds \| 3 baths \| 2,226 sq.ft.	$969,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 3.57% Airbnb Rental Income: $3286 Traditional Rental Income: $4934 Airbnb ROI: 0.92% Traditional ROI: 3.57%
51 Wimler Lane Guilford, CT Welcome to Waystone Farm, an award-winning, energy-efficient 8+ acre mini-estate and poten...	4 beds \| 4 baths \| 2,762 sq.ft.	$1,825,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 1.22% Airbnb Rental Income: $3286 Traditional Rental Income: $5279 Airbnb ROI: -0.39% 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: -0.57% Traditional cash on cash: 4.12% Airbnb Rental Income: $1716 Traditional Rental Income: $3281 Airbnb ROI: -0.57% Traditional ROI: 4.12%
33 Church St Guilford, CT The George W. Seward House - Circa 1888 A rare opportunity to own a piece of Guilford hist...	6 beds \| 3 baths \| 3,833 sq.ft.	$1,185,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 3.74% Airbnb Rental Income: $4833 Traditional Rental Income: $6492 Airbnb ROI: 1.33% 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: -0.92% Traditional cash on cash: -0.08% Airbnb Rental Income: $2543 Traditional Rental Income: $4527 Airbnb ROI: -0.92% 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: -1.52% Traditional cash on cash: -0.55% Airbnb Rental Income: $3286 Traditional Rental Income: $9264 Airbnb ROI: -1.52% Traditional ROI: -0.55%
20 Granite Road #20 Guilford, CT Bright and sunny second-floor ranch unit in desirable Walden III's parklike setting. This ...	1 beds \| 1 baths \| 874 sq.ft.	$250,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 4.28% Airbnb Rental Income: $1522 Traditional Rental Income: $1630 Airbnb ROI: 1.94% Traditional ROI: 4.28%
59 Hoadley Creek Circle Guilford, CT Welcome to 59 Hoadley Creek Circle, a beautifully updated Cape-style home set on nearly an...	3 beds \| 2 baths \| 1,198 sq.ft.	$587,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 3.38% Airbnb Rental Income: $2543 Traditional Rental Income: $3242 Airbnb ROI: 0.99% Traditional ROI: 3.38%
539-A Boston Street Guilford, CT Brand NEW CONSTRUCTION. Move in Ready! This modern, luxurious 4-bedroom, 3.5-bathroom home...	4 beds \| 4 baths \| 3,284 sq.ft.	$1,599,000	Airbnb cash on cash: -1.48% Traditional cash on cash: 1.2% Airbnb Rental Income: $3286 Traditional Rental Income: $6518 Airbnb ROI: -1.48% Traditional ROI: 1.2%
94 Mohawk Trail #94 Guilford, CT Tucked away in the serene and highly sought-after Quonnipaug Hills community, 94 Mohawk Tr...	1 beds \| 1 baths \| 839 sq.ft.	$209,900	Airbnb cash on cash: 2.67% Traditional cash on cash: 5.57% Airbnb Rental Income: $1522 Traditional Rental Income: $1657 Airbnb ROI: 2.67% Traditional ROI: 5.57%

Real Estate investment in Guilford, CT

There are 42 properties for sale in the city of Guilford . The median list price in Guilford is $825,000 and the average price per square foot is $335. In August 2026, the average monthly cash on cash return in Guilford is 3.00%. The average monthly rental income in Guilford is $3,679.

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

There are 42 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 $3,679.

Your search for investment property begins and ends here

Investment Property for Sale in Guilford, CT

1640 Little Meadow Road

Guilford, CT

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

$1,100,000

Airbnb cash on cash: 1.75%

Traditional cash on cash: 2.78%

Airbnb Rental Income: $4833

Traditional Rental Income: $4901

Airbnb ROI: 1.75%

Traditional ROI: 2.78%

405 Whitfield St #2

Guilford, CT

6 beds | 4 baths | 6,216 sq.ft.

$3,995,000

Airbnb cash on cash: -2.27%

Traditional cash on cash: -2.16%

Airbnb Rental Income: $4833

Traditional Rental Income: $4239

Airbnb ROI: -2.27%

Traditional ROI: -2.16%

66 High St #17

Guilford, CT

3 beds | 2 baths | 3,348 sq.ft.

$2,990,000

Airbnb cash on cash: -2.17%

Traditional cash on cash: -1.51%

Airbnb Rental Income: $2543

Traditional Rental Income: $3760

Airbnb ROI: -2.17%

Traditional ROI: -1.51%

1500 Durham Road

Guilford, CT

4 beds | 3 baths | 2,414 sq.ft.

$635,000

Airbnb cash on cash: 2.03%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $3286

Traditional Rental Income: $3287

Airbnb ROI: 2.03%

Traditional ROI: 3.28%

874 Nut Plains Road lot: 2 - Style A

Guilford, CT

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

$889,900

Airbnb cash on cash: -0.91%

Traditional cash on cash: 1.16%

Airbnb Rental Income: $2543

Traditional Rental Income: $3648

Airbnb ROI: -0.91%

Traditional ROI: 1.16%

1607 Great Hill Road

Guilford, CT

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

$949,000

Airbnb cash on cash: 0.92%

Traditional cash on cash: 7.45%

Airbnb Rental Income: $3286

Traditional Rental Income: $8321

Airbnb ROI: 0.92%

Traditional ROI: 7.45%

7 Caleb Court

Guilford, CT

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

$1,395,000

Airbnb cash on cash: 0.54%

Traditional cash on cash: 1.88%

Airbnb Rental Income: $4833

Traditional Rental Income: $5572

Airbnb ROI: 0.54%

Traditional ROI: 1.88%

51 Pearl St

Guilford, CT

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

$1,075,000

Airbnb cash on cash: 0.64%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $3286

Traditional Rental Income: $5390

Airbnb ROI: 0.64%