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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
249 Mill River RdChappaqua, NYNOW Easy to Show Welcome to this beautifully maintained raised ranch offering the perfect ... |
4 beds | 2 baths | 2,100 sq.ft. |
$849,999 |
Airbnb cash on cash: -0.57%
|
80 Bischoff AvenueChappaqua, NYExperience the best of convenient living in this stylishly updated 3-bedroom home, perfect... |
3 beds | 3 baths | 1,299 sq.ft. |
$685,000 |
Airbnb cash on cash: 0.25%
|
58 Maple AveChappaqua, NY
|
2 beds | 1 baths | 711 sq.ft. |
$549,000 |
Airbnb cash on cash: -0.41%
|
406 Bedford RdChappaqua, NYWelcome home to this pristine and wonderfully updated 4 bdrm Colonial bordered by a gorgeo... |
4 beds | 3 baths | 2,913 sq.ft. |
$1,800,000 |
Airbnb cash on cash: -0.67%
|
40 Hamilton DrChappaqua, NYBe the first to live in this custom new construction home that offers a lifestyle of unpar... |
4 beds | 4 baths | 5,918 sq.ft. |
$2,649,000 |
Airbnb cash on cash: -1%
|
2 Timberland PassChappaqua, NYWelcome to Apple Hill Farm, sitting on highly desirable, 37+ Wooded Acres. Where calm meet... |
3 beds | 2 baths | 1,586 sq.ft. |
$839,999 |
Airbnb cash on cash: -0.64%
|
73 S Bedford RdChappaqua, NYWelcome home to this well-maintained residence in the heart of vibrant Chappaqua! This 4 b... |
4 beds | 2 baths | 1,584 sq.ft. |
$809,000 |
Airbnb cash on cash: -0.15%
|
20 Bessel LnChappaqua, NY20 Bessel Ln, Chappaqua, NY 10514 | Single Family Residential |
6 beds | 5 baths | 8,200 sq.ft. |
$2,990,000 |
Airbnb cash on cash: -1.36%
|
26 Wallace WayChappaqua, NYWelcome to 26 Wallace Way - a standout residence in the coveted, sold-out Chappaqua Crossi... |
2 beds | 4 baths | 2,945 sq.ft. |
$1,780,000 |
Airbnb cash on cash: -2.69%
|
150 Old Farm Rd NChappaqua, NY150 Old Farm Rd N, Chappaqua, NY 10514 | Single Family Residential |
5 beds | 5 baths | 7,608 sq.ft. |
$4,500,000 |
Airbnb cash on cash: -1.82%
|
65 S Bedford RdChappaqua, NY65 S Bedford Rd, Chappaqua, NY 10514 | Other |
N/A beds | N/A baths | N/A |
$639,000 |
Airbnb cash on cash: -1.67%
|
816 Hardscrabble RoadChappaqua, NYJust north of NYC, this move-in ready CHAPPAQUA home delivers effortless, elevated living-... |
3 beds | 3 baths | 2,444 sq.ft. |
$1,299,000 |
Airbnb cash on cash: -0.72%
|
368 N Greeley AvenueChappaqua, NYWelcome to Chestnut Oaks, a sought-after condominium community just moments from downtown ... |
1 beds | 2 baths | 1,207 sq.ft. |
$510,000 |
Airbnb cash on cash: -1.29%
|
25 Cabin Ridge RoadChappaqua, NYEscape to your own private retreat on 3.44 acres of wooded land, where rustic charm meets ... |
3 beds | 4 baths | 2,708 sq.ft. |
$1,199,000 |
Airbnb cash on cash: -1.08%
|
52-54 Orchard Ridge RoadChappaqua, NYRare opportunity to own two side-by-side residences on a beautifully landscaped 0.45-acre ... |
7 beds | 3 baths | N/A |
$1,595,000 |
Airbnb cash on cash: -0.11%
|
134 Bayberry CloseChappaqua, NYWelcome to 134 Bayberry Close in the sought-after Old Farm Lake community, in the heart of... |
2 beds | 3 baths | 1,818 sq.ft. |
$725,000 |
Airbnb cash on cash: -0.34%
|
676 Hardscrabble RdChappaqua, NYRenovated and Reimagined Colonial on Spectacular Park-Like Grounds, this exceptional resid... |
3 beds | 2 baths | 2,420 sq.ft. |
$1,495,000 |
Airbnb cash on cash: -1.04%
|
220 Mill River RdChappaqua, NY220 Mill River Rd, Chappaqua, NY 10514 | Single Family Residential |
3 beds | 1 baths | 1,538 sq.ft. |
$790,000 |
Airbnb cash on cash: 0.18%
|
131 Douglas RdChappaqua, NY131 Douglas Rd, Chappaqua, NY 10514 | Single Family Residential |
3 beds | 3 baths | 2,690 sq.ft. |
$1,590,000 |
Airbnb cash on cash: -1.27%
|
312 Quaker RdChappaqua, NY312 Quaker Rd, Chappaqua, NY 10514 | Single Family Residential |
3 beds | 2 baths | 2,451 sq.ft. |
$1,550,000 |
Airbnb cash on cash: -1.23%
|
9 Oak Hill RdChappaqua, NY9 Oak Hill Rd, Chappaqua, NY 10514 | Single Family Residential |
4 beds | 3 baths | 2,406 sq.ft. |
$1,299,000 |
Airbnb cash on cash: -1.07%
|
4 Old House LnChappaqua, NY4 Old House Ln, Chappaqua, NY 10514 | Single Family Residential |
4 beds | 3 baths | 3,124 sq.ft. |
$1,998,999 |
Airbnb cash on cash: -1.65%
|
2 Turner DrChappaqua, NY2 Turner Dr, Chappaqua, NY 10514 | Single Family Residential |
5 beds | 3 baths | 2,715 sq.ft. |
$1,100,000 |
Airbnb cash on cash: 0.95%
|
309 N Greeley Ave #5CChappaqua, NY309 N Greeley Ave #5C, Chappaqua, NY 10514 | Condo/Coop |
2 beds | 1 baths | 1,200 sq.ft. |
$579,000 |
Airbnb cash on cash: -1.26%
|
17 Lila LnChappaqua, NY17 Lila Ln, Chappaqua, NY 10514 | Condo/Coop |
3 beds | 2 baths | 2,576 sq.ft. |
$1,590,000 |
Airbnb cash on cash: -1.79%
|
33 Greenbriar DrChappaqua, NY33 Greenbriar Dr, Chappaqua, NY 10514 | Single Family Residential |
3 beds | 4 baths | 6,115 sq.ft. |
$2,249,000 |
Airbnb cash on cash: -1.69%
|
39 Barnes LnChappaqua, NY39 Barnes Ln, Chappaqua, NY 10514 | Single Family Residential |
4 beds | 5 baths | 4,589 sq.ft. |
$2,995,000 |
Airbnb cash on cash: -2%
|
767 King StChappaqua, NY767 King St, Chappaqua, NY | Other |
N/A beds | N/A baths | N/A |
$1,665,000 |
Airbnb cash on cash: -2.31%
|
42 Hollow Oak RdChappaqua, NY42 Hollow Oak Rd, Chappaqua, NY 10514 | Single Family Residential |
3 beds | 2 baths | 2,380 sq.ft. |
$950,000 |
Airbnb cash on cash: -0.3%
|
27 Mill River RdChappaqua, NY27 Mill River Rd, Chappaqua, NY 10514 | Single Family Residential |
3 beds | 1 baths | 1,414 sq.ft. |
$749,000 |
Airbnb cash on cash: 0.34%
|
10 Paula PlChappaqua, NY10 Paula Pl, Chappaqua, NY 10514 | Single Family Residential |
4 beds | 2 baths | 2,464 sq.ft. |
$679,000 |
Airbnb cash on cash: 0.42%
|
10 Deborah LnChappaqua, NY10 Deborah Ln, Chappaqua, NY 10514 | Single Family Residential |
3 beds | 3 baths | 2,821 sq.ft. |
$1,399,000 |
Airbnb cash on cash: -1.07%
|
24 Trails EndChappaqua, NY24 Trails End, Chappaqua, NY 10514 | Single Family Residential |
6 beds | 7 baths | 9,247 sq.ft. |
$5,750,000 |
Airbnb cash on cash: -2.01%
|
53 W Orchard RdChappaqua, NY53 W Orchard Rd, Chappaqua, NY 10514 | Single Family Residential |
4 beds | 3 baths | 3,581 sq.ft. |
$1,725,000 |
Airbnb cash on cash: -1.48%
|
767 King StChappaqua, NY767 King St, Chappaqua, NY 10514 | Other |
N/A beds | N/A baths | N/A |
$1,665,000 |
Airbnb cash on cash: -2.31%
|
Real Estate investment in Chappaqua, NY
There are 34 properties for sale in the city of Chappaqua . The median list price in Chappaqua is $899,462 and the average price per square foot is $291. In October 2026, the average monthly cash on cash return in Chappaqua is 1.00%. The average monthly rental income in Chappaqua is $4,696.