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: 2.98% Traditional cash on cash: 2.09% Airbnb Rental Income: $4359 Traditional Rental Income: $2885 Airbnb ROI: 2.98% Traditional ROI: 2.09%
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: 0.03% Traditional cash on cash: -1.9% Airbnb Rental Income: $10586 Traditional Rental Income: $4166 Airbnb ROI: 0.03% Traditional ROI: -1.9%
7 Deer Run Chappaqua, NY Step into luxury - in this fully renovated condo in Chappaqua at Old Farm Lake developmen...	2 beds \| 2 baths \| 1,549 sq.ft.	$750,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 1.73% Airbnb Rental Income: $3420 Traditional Rental Income: $3307 Airbnb ROI: 0.8% Traditional ROI: 1.73%
4 TIMBERLAND PASS Chappaqua, NY This home is located in sought after Apple Hill Farm community in Chappaqua NY. This home ...	2 beds \| 3 baths \| 1,566 sq.ft.	$595,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 2.2% Airbnb Rental Income: $3420 Traditional Rental Income: $3650 Airbnb ROI: 0.42% Traditional ROI: 2.2%
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: 1.38% Airbnb Rental Income: $6453 Traditional Rental Income: $4586 Airbnb ROI: 1.92% Traditional ROI: 1.38%
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%
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: 2.88% Traditional cash on cash: 0.16% Airbnb Rental Income: $10586 Traditional Rental Income: $4587 Airbnb ROI: 2.88% Traditional ROI: 0.16%
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: -0.39% Traditional cash on cash: -0.92% Airbnb Rental Income: $10586 Traditional Rental Income: $6931 Airbnb ROI: -0.39% Traditional ROI: -0.92%
30 Lori Lane Chappaqua, NY Move right in! Enjoy easy living in this updated, sun-filled home located in a quiet neigh...	4 beds \| 3 baths \| 2,288 sq.ft.	$1,200,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 2.53% Airbnb Rental Income: $10586 Traditional Rental Income: $5869 Airbnb ROI: 5.01% Traditional ROI: 2.53%
54 Spring Road Chappaqua, NY Set on a quiet street just a few minutes from Chappaqua town center, this charming colonia...	3 beds \| 4 baths \| 2,482 sq.ft.	$1,175,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 0.44% Airbnb Rental Income: $6453 Traditional Rental Income: $3645 Airbnb ROI: 1.85% Traditional ROI: 0.44%
100 Castle Road Chappaqua, NY Prime Chappaqua Location SCHEDULED INSTALLATION ! ENSUITE A MUST SEE! Walk to Town & Tra...	3 beds \| 3 baths \| 1,755 sq.ft.	$1,099,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 1.2% Airbnb Rental Income: $6453 Traditional Rental Income: $3823 Airbnb ROI: 2.54% Traditional ROI: 1.2%
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: 3.62% Traditional cash on cash: 1.76% Airbnb Rental Income: $10586 Traditional Rental Income: $6251 Airbnb ROI: 3.62% 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: 1.55% Traditional cash on cash: 0.1% Airbnb Rental Income: $10586 Traditional Rental Income: $6206 Airbnb ROI: 1.55% Traditional ROI: 0.1%
40 Aldridge Road Chappaqua, NY Move right in to this beautiful home perfectly situated on a tranquil cul-de-sac, offering...	4 beds \| 4 baths \| 3,541 sq.ft.	$1,755,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 1.31% Airbnb Rental Income: $10586 Traditional Rental Income: $6176 Airbnb ROI: 2.82% Traditional ROI: 1.31%
105 Rambling Brook Road #R Chappaqua, NY Situated in the highly sought-after Old Farm Lake complex, this bright 2-bedroom condo boa...	2 beds \| 3 baths \| 1,244 sq.ft.	$749,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 1.84% Airbnb Rental Income: $3420 Traditional Rental Income: $3393 Airbnb ROI: 0.79% Traditional ROI: 1.84%
20 Lawrence Frm Crswy Chappaqua, NY Discover this beautifully updated and turnkey Contemporary home, ideally situated on a pri...	4 beds \| 3 baths \| 4,085 sq.ft.	$1,599,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 0.28% Airbnb Rental Income: $10586 Traditional Rental Income: $4864 Airbnb ROI: 2.81% Traditional ROI: 0.28%
33 Chatham Road Chappaqua, NY Beautifully renovated home 3 bedroom 2.5 bath on 1.3 acres in Chappaqua Ridge community. ...	3 beds \| 3 baths \| 2,100 sq.ft.	$999,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 1.98% Airbnb Rental Income: $6453 Traditional Rental Income: $4521 Airbnb ROI: 2.7% Traditional ROI: 1.98%
12 Pines Lane Chappaqua, NY Delightful 1940s expanded ranch sits on a lovely 1/2 acre parcel in a super convenient loc...	3 beds \| 2 baths \| 2,249 sq.ft.	$795,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 1.64% Airbnb Rental Income: $6453 Traditional Rental Income: $3809 Airbnb ROI: 3.5% Traditional ROI: 1.64%
4 Timberland Pass #4 Chappaqua, NY This home is located in Apple Hill Farm community in Chappaqua NY. This End unit Townhome ...	2 beds \| 3 baths \| 1,550 sq.ft.	$595,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 1.75% Airbnb Rental Income: $3420 Traditional Rental Income: $3539 Airbnb ROI: 0.17% Traditional ROI: 1.75%
105 Rambling Brook Road Chappaqua, NY Situated in the highly sought-after Old Farm Lake complex, this bright 2-bedroom condo boa...	2 beds \| 3 baths \| 1,296 sq.ft.	$749,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 2.03% Airbnb Rental Income: $3420 Traditional Rental Income: $3525 Airbnb ROI: 0.79% Traditional ROI: 2.03%

Real Estate investment in Chappaqua, NY

There are 20 properties for sale in the city of Chappaqua . The median list price in Chappaqua is $1,187,500 and the average price per square foot is $409. In January 2025, the average monthly cash on cash return in Chappaqua is 2.00%. The average monthly rental income in Chappaqua is $4,344.

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

There are 20 investment properties available for sale in Chappaqua.

In 2025, 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 $6,453.

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: 2.98%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $4359

Traditional Rental Income: $2885

Airbnb ROI: 2.98%

Traditional ROI: 2.09%

17 Colony Row

Chappaqua, NY

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

$2,495,000

Airbnb cash on cash: 0.03%

Traditional cash on cash: -1.9%

Airbnb Rental Income: $10586

Traditional Rental Income: $4166

Airbnb ROI: 0.03%

Traditional ROI: -1.9%

7 Deer Run

Chappaqua, NY

2 beds | 2 baths | 1,549 sq.ft.

$750,000

Airbnb cash on cash: 0.8%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $3420

Traditional Rental Income: $3307

Airbnb ROI: 0.8%

Traditional ROI: 1.73%

4 TIMBERLAND PASS

Chappaqua, NY

2 beds | 3 baths | 1,566 sq.ft.

$595,000

Airbnb cash on cash: 0.42%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $3420

Traditional Rental Income: $3650

Airbnb ROI: 0.42%

Traditional ROI: 2.2%

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: 1.38%

Airbnb Rental Income: $6453

Traditional Rental Income: $4586

Airbnb ROI: 1.92%

Traditional ROI: 1.38%

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%

140 S Bedford Road

Chappaqua, NY

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

$1,599,000

Airbnb cash on cash: 2.88%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $10586

Traditional Rental Income: $4587

Airbnb ROI: 2.88%

Traditional ROI: 0.16%

72 Carolyn Place

Chappaqua, NY

4 beds | 8 baths | 8,291 sq.ft.

$3,499,000

Airbnb cash on cash: -0.39%

Traditional cash on cash: -0.92%

Airbnb Rental Income: $10586

Traditional Rental Income: $6931

Airbnb ROI: -0.39%