Real Estate Investment Properties for Sale in Glen Head, NY

Looking for investment property in Glen Head, NY with high ROI ?

Explore a variety of short-term homes & houses in Glen Head, NY. Invest wisely with VRBO & Glen Head, NY 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 Glen Head, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
167 Brookville Rd Glen Head, NY This grand, gated estate blends timeless elegance with modern convenience, showcasing meti...	5 beds \| 6 baths \| 5,377 sq.ft.	$5,200,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.56% Airbnb Rental Income: $null Traditional Rental Income: $6737 Airbnb ROI: N/A Traditional ROI: -0.56%
30 Sheppard Street Glen Head, NY Welcome Home to This All Updated Ranch in Glen Head, Hardwood Floors, Formal Living Room w...	3 beds \| 2 baths \| 930 sq.ft.	$769,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 2.29% Airbnb Rental Income: $2872 Traditional Rental Income: $3381 Airbnb ROI: 0.65% Traditional ROI: 2.29%
8 Vista Ln Glen Head, NY For the Discerning Client who seeks only the Finest....Welcome to 8 Vista Lane in Brookvil...	5 beds \| 7 baths \| 7,000 sq.ft.	$5,300,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.37% Airbnb Rental Income: $null Traditional Rental Income: $8936 Airbnb ROI: N/A Traditional ROI: -1.37%
42 Smith Street Glen Head, NY Welcome to this beautifully renovated Expanded Cape in the heart of Glen Head. Featuring 3...	3 beds \| 3 baths \| 1,075 sq.ft.	$849,990	Airbnb cash on cash: 0.32% Traditional cash on cash: 2.25% Airbnb Rental Income: $2872 Traditional Rental Income: $3735 Airbnb ROI: 0.32% Traditional ROI: 2.25%
40 Cedar Lane N Glen Head, NY Southern-facing, spacious, light-filled, and private townhouse featuring sleek black hardw...	2 beds \| 4 baths \| 2,500 sq.ft.	$899,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 2.63% Airbnb Rental Income: $1780 Traditional Rental Income: $4350 Airbnb ROI: -1.02% Traditional ROI: 2.63%
30 Roslyn Drive Glen Head, NY Welcome to 30 Roslyn Drive in Glen Head. Nestled in a quiet neighborhood on a quarter-acre...	5 beds \| 4 baths \| 3,280 sq.ft.	$1,895,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.75% Airbnb Rental Income: $null Traditional Rental Income: $6286 Airbnb ROI: N/A Traditional ROI: 1.75%
13 Prospect Street Glen Head, NY Situated in Glen Head, this inviting 2-bedroom, 1-bath home features a cozy floor plan fil...	2 beds \| 1 baths \| 948 sq.ft.	$650,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 2.45% Airbnb Rental Income: $1780 Traditional Rental Income: $3072 Airbnb ROI: -0.48% Traditional ROI: 2.45%
32 The Glen unit: 32 #32 Glen Head, NY Bright and beautifully updated residence in The Knolls gated community. Features include a...	3 beds \| 4 baths \| N/A	$999,000	Airbnb cash on cash: -1.66% Traditional cash on cash: 1.83% Airbnb Rental Income: $2872 Traditional Rental Income: $5443 Airbnb ROI: -1.66% Traditional ROI: 1.83%
11 Glenwood Rd Glen Head, NY Discover the options with this home! Enjoy the traditional layout OR explore the options f...	4 beds \| 2 baths \| 1,628 sq.ft.	$899,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 2.36% Airbnb Rental Income: $3725 Traditional Rental Income: $4005 Airbnb ROI: 1.05% Traditional ROI: 2.36%
33 Scudders Lane Glen Head, NY Fully renovated in 2019, this stylish 3-bedroom, 2.5-bath home offers a true open layout w...	3 beds \| 3 baths \| 2,500 sq.ft.	$1,348,000	Airbnb cash on cash: -0.46% Traditional cash on cash: 1.45% Airbnb Rental Income: $2872 Traditional Rental Income: $4598 Airbnb ROI: -0.46% Traditional ROI: 1.45%
18 Knoll Lane Glen Head, NY Welcome to luxury living in Glen Head. This meticulously maintained colonial spans nearly ...	5 beds \| 4 baths \| 2,957 sq.ft.	$1,599,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.6% Airbnb Rental Income: $null Traditional Rental Income: $5994 Airbnb ROI: N/A Traditional ROI: 1.6%
2177 Cedar Swamp Rd Glen Head, NY Discover this private 2-acre estate nestled in the prestigious Brookville Village, located...	5 beds \| 4 baths \| 3,009 sq.ft.	$1,899,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.06% Airbnb Rental Income: $null Traditional Rental Income: $6453 Airbnb ROI: N/A Traditional ROI: 1.06%
22 Brookville Rd Glen Head, NY 22 Brookville Rd, Glen Head, NY 11545 \| Single Family Residential	6 beds \| 3 baths \| 3,818 sq.ft.	$2,099,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.22% Airbnb Rental Income: $null Traditional Rental Income: $4944 Airbnb ROI: N/A Traditional ROI: -0.22%
20 Knollwood Rd Glen Head, NY 20 Knollwood Rd, Glen Head, NY 11545 \| Single Family Residential	6 beds \| 7 baths \| 7,314 sq.ft.	$5,995,999	Airbnb cash on cash: N/A Traditional cash on cash: -1.24% Airbnb Rental Income: $null Traditional Rental Income: $8302 Airbnb ROI: N/A Traditional ROI: -1.24%
2T Coolidge Ave Glen Head, NY Beautifully maintained Center Hall Colonial in the heart of Glen Head. This home features ...	4 beds \| 3 baths \| 2,982 sq.ft.	$1,599,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 0.75% Airbnb Rental Income: $3725 Traditional Rental Income: $4789 Airbnb ROI: -0.51% Traditional ROI: 0.75%
2340 Cedar Swamp Rd Glen Head, NY 2340 Cedar Swamp Rd, Glen Head, NY 11545 \| Single Family Residential	N/A beds \| N/A baths \| 0 sq.ft.	$15,000,000	Airbnb cash on cash: -2.71% Traditional cash on cash: -2.58% Airbnb Rental Income: $443 Traditional Rental Income: $1901 Airbnb ROI: -2.71% Traditional ROI: -2.58%
2 Terry Ct Glen Head, NY 2 Terry Ct, Glen Head, NY 11545 \| Single Family Residential	3 beds \| 2 baths \| 2,164 sq.ft.	$1,389,000	Airbnb cash on cash: -1.08% Traditional cash on cash: -0.14% Airbnb Rental Income: $2872 Traditional Rental Income: $3417 Airbnb ROI: -1.08% Traditional ROI: -0.14%
20 Rolling Dr Glen Head, NY 20 Rolling Dr, Glen Head, NY 11545 \| Single Family Residential	6 beds \| 6 baths \| 5,972 sq.ft.	$2,999,999	Airbnb cash on cash: N/A Traditional cash on cash: 0.17% Airbnb Rental Income: $null Traditional Rental Income: $8103 Airbnb ROI: N/A Traditional ROI: 0.17%
30 Wood Acres Rd Glen Head, NY 30 Wood Acres Rd, Glen Head, NY 11545 \| Single Family Residential	6 beds \| 7 baths \| 8,000 sq.ft.	$8,750,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.7% Airbnb Rental Income: $null Traditional Rental Income: $8353 Airbnb ROI: N/A Traditional ROI: -1.7%

Real Estate investment in Glen-head, NY

There are 37 properties for sale in the city of Glen Head . The median list price in Glen Head is $2,099,000 and the average price per square foot is $630. In February 2026, the average monthly cash on cash return in Glen Head is N/A%. The average monthly rental income in Glen Head is $4,867.

Glen-head, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 37 investment properties available for sale in Glen-head.

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

The ROI for Long-Term is higher than the Short-Term in Glen-head with average rental income of $4,867.

Your search for investment property begins and ends here

Investment Property for Sale in Glen Head, NY

167 Brookville Rd

Glen Head, NY

5 beds | 6 baths | 5,377 sq.ft.

$5,200,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.56%

Airbnb Rental Income: $null

Traditional Rental Income: $6737

Airbnb ROI: N/A

Traditional ROI: -0.56%

30 Sheppard Street

Glen Head, NY

3 beds | 2 baths | 930 sq.ft.

$769,000

Airbnb cash on cash: 0.65%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $2872

Traditional Rental Income: $3381

Airbnb ROI: 0.65%

Traditional ROI: 2.29%

8 Vista Ln

Glen Head, NY

5 beds | 7 baths | 7,000 sq.ft.

$5,300,000

Airbnb cash on cash: N/A

Traditional cash on cash: -1.37%

Airbnb Rental Income: $null

Traditional Rental Income: $8936

Airbnb ROI: N/A

Traditional ROI: -1.37%

42 Smith Street

Glen Head, NY

3 beds | 3 baths | 1,075 sq.ft.

$849,990

Airbnb cash on cash: 0.32%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $2872

Traditional Rental Income: $3735

Airbnb ROI: 0.32%

Traditional ROI: 2.25%

40 Cedar Lane N

Glen Head, NY

2 beds | 4 baths | 2,500 sq.ft.

$899,000

Airbnb cash on cash: -1.02%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $1780

Traditional Rental Income: $4350

Airbnb ROI: -1.02%

Traditional ROI: 2.63%

30 Roslyn Drive

Glen Head, NY

5 beds | 4 baths | 3,280 sq.ft.

$1,895,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.75%

Airbnb Rental Income: $null

Traditional Rental Income: $6286

Airbnb ROI: N/A

Traditional ROI: 1.75%

13 Prospect Street

Glen Head, NY

2 beds | 1 baths | 948 sq.ft.

$650,000

Airbnb cash on cash: -0.48%

Traditional cash on cash: 2.45%

Airbnb Rental Income: $1780

Traditional Rental Income: $3072

Airbnb ROI: -0.48%

Traditional ROI: 2.45%

32 The Glen unit: 32 #32

Glen Head, NY

3 beds | 4 baths | N/A

$999,000

Airbnb cash on cash: -1.66%

Traditional cash on cash: 1.83%

Airbnb Rental Income: $2872

Traditional Rental Income: $5443

Airbnb ROI: -1.66%