Real Estate Investment Properties for Sale in Chappaqua, NY

Looking for investment property in Chappaqua, NY with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1008 King Street Chappaqua, NY Builders wanted for Large building Lot, Plans Designs are included for a 2828 Sq Ft reside...	1 beds \| 2 baths \| 1,052 sq.ft.	$675,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 2.76% Airbnb Rental Income: $3427 Traditional Rental Income: $3307 Airbnb ROI: 1.75% Traditional ROI: 2.76%
17 Colony Row Chappaqua, NY This exceptional 4 (lives like 5/6) bedroom Colonial blends sophistication, elegance, and ...	4 beds \| 6 baths \| 5,680 sq.ft.	$2,495,000	Airbnb cash on cash: -3.07% Traditional cash on cash: -1.9% Airbnb Rental Income: $1975 Traditional Rental Income: $4166 Airbnb ROI: -3.07% Traditional ROI: -1.9%
94 Orchard Ridge Road Chappaqua, NY This beautifully updated colonial in Chappaqua village offers the perfect combination of v...	3 beds \| 3 baths \| 2,134 sq.ft.	$1,199,999	Airbnb cash on cash: 1.92% Traditional cash on cash: 1.5% Airbnb Rental Income: $6453 Traditional Rental Income: $4726 Airbnb ROI: 1.92% Traditional ROI: 1.5%
256 Quaker Road Chappaqua, NY Just completed! In-town location ready to move in. This state of the art offering, by este...	3 beds \| 4 baths \| 4,389 sq.ft.	$1,950,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 0.33% Airbnb Rental Income: $6453 Traditional Rental Income: $3749 Airbnb ROI: 1.13% Traditional ROI: 0.33%
70 Cowdin Lane Chappaqua, NY Welcome to 70 Cowdin Lane! Nestled at the end of a highly sought after private lane in the...	4 beds \| 4 baths \| 5,309 sq.ft.	$2,050,000	Airbnb cash on cash: -2.8% Traditional cash on cash: 0.31% Airbnb Rental Income: $1975 Traditional Rental Income: $7367 Airbnb ROI: -2.8% Traditional ROI: 0.31%
34 Pebblebrook Way Chappaqua, NY The only triple mint move-in condition house in Chappaqua schools. Nestled within 1.65 a...	5 beds \| 5 baths \| 4,482 sq.ft.	$2,499,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.35% Airbnb Rental Income: $null Traditional Rental Income: $7458 Airbnb ROI: N/A Traditional ROI: 0.35%
129 Bayberry Close Chappaqua, NY FULLY AVAILABLE! Clean and bright two-bedroom townhome tucked away in the sought after Old...	2 beds \| 3 baths \| 1,653 sq.ft.	$765,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 2.81% Airbnb Rental Income: $4868 Traditional Rental Income: $4088 Airbnb ROI: 2.5% Traditional ROI: 2.81%
140 S Bedford Road Chappaqua, NY Modern Colonial, nestled on a private 1.23 acre lot in the Chappaqua School District. This...	4 beds \| 3 baths \| 3,631 sq.ft.	$1,599,000	Airbnb cash on cash: -1.95% Traditional cash on cash: -0.47% Airbnb Rental Income: $1975 Traditional Rental Income: $3649 Airbnb ROI: -1.95% Traditional ROI: -0.47%
72 Carolyn Place Chappaqua, NY Elegant and sophisticated, shingle style Colonial sited on 3.46 acres of level, idyllic, p...	4 beds \| 8 baths \| 8,291 sq.ft.	$3,499,000	Airbnb cash on cash: -2.6% Traditional cash on cash: -1.77% Airbnb Rental Income: $1975 Traditional Rental Income: $4166 Airbnb ROI: -2.6% Traditional ROI: -1.77%
6 Sabina Road Chappaqua, NY Set on a generous acre, this charming 3-bedroom home with an additional office/den exudes ...	3 beds \| 2 baths \| 2,428 sq.ft.	$939,800	Airbnb cash on cash: 2.7% Traditional cash on cash: 1.37% Airbnb Rental Income: $6453 Traditional Rental Income: $4023 Airbnb ROI: 2.7% Traditional ROI: 1.37%
10 High Point Circle Chappaqua, NY Discover unparalleled privacy and a serene lifestyle in this secluded 4/5 bedroom, 3 1/2 b...	4 beds \| 4 baths \| 3,792 sq.ft.	$1,749,000	Airbnb cash on cash: -2.18% Traditional cash on cash: 0.82% Airbnb Rental Income: $1975 Traditional Rental Income: $6326 Airbnb ROI: -2.18% Traditional ROI: 0.82%
140 Deer Run Chappaqua, NY This turnkey first floor unit in Old Farm Lake is beyond appealing with its beautifully re...	1 beds \| 1 baths \| 837 sq.ft.	$439,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 2.81% Airbnb Rental Income: $3427 Traditional Rental Income: $2910 Airbnb ROI: 2.21% Traditional ROI: 2.81%
66 Hilltop Drive Chappaqua, NY This distinguished, sun-filled colonial is gracefully set on a meticulously landscaped acr...	4 beds \| 5 baths \| 5,395 sq.ft.	$2,199,999	Airbnb cash on cash: -2.52% Traditional cash on cash: 0.33% Airbnb Rental Income: $1975 Traditional Rental Income: $7286 Airbnb ROI: -2.52% Traditional ROI: 0.33%
9 Killington Street Chappaqua, NY Discover the timeless beauty of midcentury modern design with this extraordinary home in a...	3 beds \| 3 baths \| 2,625 sq.ft.	$1,325,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 0.38% Airbnb Rental Income: $6453 Traditional Rental Income: $4639 Airbnb ROI: 0.82% Traditional ROI: 0.38%
100 Castle Road Chappaqua, NY Prime Chappaqua Location Walk to Town & Train! This beautifully maintained 3-bedroom Col...	3 beds \| 3 baths \| 1,570 sq.ft.	$1,199,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 0.4% Airbnb Rental Income: $6453 Traditional Rental Income: $3133 Airbnb ROI: 2.25% Traditional ROI: 0.4%
129 Millwood Road Chappaqua, NY Discover your perfect oasis in this meticulously cared-for 4-bedroom Dutch Colonial, situa...	4 beds \| 4 baths \| 2,700 sq.ft.	$899,000	Airbnb cash on cash: -1.36% Traditional cash on cash: 1.42% Airbnb Rental Income: $1975 Traditional Rental Income: $3777 Airbnb ROI: -1.36% Traditional ROI: 1.42%
3 High Point Circle Chappaqua, NY Welcome to 3 High Point Circle! This delightful home features 4 spacious bedrooms + 3.5 ba...	4 beds \| 4 baths \| 3,421 sq.ft.	$1,375,000	Airbnb cash on cash: -1.99% Traditional cash on cash: 1.76% Airbnb Rental Income: $1975 Traditional Rental Income: $6251 Airbnb ROI: -1.99% Traditional ROI: 1.76%
15 Gedney Way Chappaqua, NY Presenting a classic and meticulously maintained Bradley-built, 3,610 sq ft, 4/5-bedroom C...	4 beds \| 4 baths \| 3,610 sq.ft.	$1,799,000	Airbnb cash on cash: -2.75% Traditional cash on cash: 0.1% Airbnb Rental Income: $1975 Traditional Rental Income: $6206 Airbnb ROI: -2.75% Traditional ROI: 0.1%
51 Granite Court Chappaqua, NY Sophisticated and Stunning Chappaqua Estate! Sure to please the most discerning buyer, thi...	5 beds \| 5 baths \| 5,836 sq.ft.	$2,995,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.79% Airbnb Rental Income: $null Traditional Rental Income: $7462 Airbnb ROI: N/A Traditional ROI: 0.79%
2 Timberland Pass Chappaqua, NY With a pool and tennis courts a short walk away, you will feel like you are at a vacation ...	3 beds \| 3 baths \| 1,586 sq.ft.	$799,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 1.48% Airbnb Rental Income: $6453 Traditional Rental Income: $3680 Airbnb ROI: 3.5% Traditional ROI: 1.48%

Real Estate investment in Chappaqua, NY

There are 20 properties for sale in the city of Chappaqua . The median list price in Chappaqua is $1,487,000 and the average price per square foot is $422. In November 2024, the average monthly cash on cash return in Chappaqua is 1.00%. The average monthly rental income in Chappaqua is $4,166.

Chappaqua, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 20 investment properties available for sale in Chappaqua.

In 2024, the best neighborhood to buy investment property is Chappaqua.

The ROI for Short-Term is higher than the Long-Term in Chappaqua with average rental income of $2,701.

Your search for investment property begins and ends here

Investment Property for Sale in Chappaqua, NY

1008 King Street

Chappaqua, NY

1 beds | 2 baths | 1,052 sq.ft.

$675,000

Airbnb cash on cash: 1.75%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $3427

Traditional Rental Income: $3307

Airbnb ROI: 1.75%

Traditional ROI: 2.76%

17 Colony Row

Chappaqua, NY

4 beds | 6 baths | 5,680 sq.ft.

$2,495,000

Airbnb cash on cash: -3.07%

Traditional cash on cash: -1.9%

Airbnb Rental Income: $1975

Traditional Rental Income: $4166

Airbnb ROI: -3.07%

Traditional ROI: -1.9%

94 Orchard Ridge Road

Chappaqua, NY

3 beds | 3 baths | 2,134 sq.ft.

$1,199,999

Airbnb cash on cash: 1.92%

Traditional cash on cash: 1.5%

Airbnb Rental Income: $6453

Traditional Rental Income: $4726

Airbnb ROI: 1.92%

Traditional ROI: 1.5%

256 Quaker Road

Chappaqua, NY

3 beds | 4 baths | 4,389 sq.ft.

$1,950,000

Airbnb cash on cash: 1.13%

Traditional cash on cash: 0.33%

Airbnb Rental Income: $6453

Traditional Rental Income: $3749

Airbnb ROI: 1.13%

Traditional ROI: 0.33%

70 Cowdin Lane

Chappaqua, NY

4 beds | 4 baths | 5,309 sq.ft.

$2,050,000

Airbnb cash on cash: -2.8%

Traditional cash on cash: 0.31%

Airbnb Rental Income: $1975

Traditional Rental Income: $7367

Airbnb ROI: -2.8%

Traditional ROI: 0.31%

34 Pebblebrook Way

Chappaqua, NY

5 beds | 5 baths | 4,482 sq.ft.

$2,499,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.35%

Airbnb Rental Income: $null

Traditional Rental Income: $7458

Airbnb ROI: N/A

Traditional ROI: 0.35%

129 Bayberry Close

Chappaqua, NY

2 beds | 3 baths | 1,653 sq.ft.

$765,000

Airbnb cash on cash: 2.5%

Traditional cash on cash: 2.81%

Airbnb Rental Income: $4868

Traditional Rental Income: $4088

Airbnb ROI: 2.5%

Traditional ROI: 2.81%

140 S Bedford Road

Chappaqua, NY

4 beds | 3 baths | 3,631 sq.ft.

$1,599,000

Airbnb cash on cash: -1.95%

Traditional cash on cash: -0.47%

Airbnb Rental Income: $1975

Traditional Rental Income: $3649

Airbnb ROI: -1.95%