The most expensive neighborhoods in Poughkeepsie
Homebuyers and sellers are navigating a slow and expensive housing market, with rising prices and stagnant demand keeping many on the sidelines. This comes amid rising economic uncertainty and growing wealth concentration. But luxury homes—multimillion-dollar estates, sleek penthouses, and one-of-a-kind custom builds—are still selling, even as most buyers pull back.
Most people can't afford high-end homes, although they're still fun to dream about. So, to highlight where luxury real estate is commanding the highest prices, Redfin analyzed the most expensive neighborhoods in the Poughkeepsie metro area—and showcased a few of the area's standout listings (when possible).
Note: Redfin's analysis focused on metro areas, meaning some neighborhoods fell within smaller nearby cities. Listings and data were gathered on October 15, 2025.
#1. West Fishkill (Beacon, NY)
Median sale price: $547,450 | Median days on market: 54 days16 Alder Way, Wappingers Falls, NY 12590
- List price: $795,000
- Beds: 4 | Baths: 2.5 | Square feet: 2,538
- See 16 Alder Way, Wappingers Falls, NY 12590 on Redfin.com
21 Lamplight St, Beacon, NY 12508
- List price: $399,000
- Beds: 2 | Baths: 2 | Square feet: 1,275
- See 21 Lamplight St, Beacon, NY 12508 on Redfin.com
29 Lamplight St, Beacon, NY 12508
- List price: $380,000
- Beds: 2 | Baths: 1.5 | Square feet: 1,137
- See 29 Lamplight St, Beacon, NY 12508 on Redfin.com
8 Cedardale Loop, Wappingers Falls, NY 12590
- List price: $799,997
- Beds: 4 | Baths: 2.5 | Square feet: 3,507
- See 8 Cedardale Loop, Wappingers Falls, NY 12590 on Redfin.com
#2. Highland Mills (Woodbury, NY)
Median sale price: $522,500 | Median days on market: 35 days1 Grant Ct, Highland Mills, NY 10930
- List price: $649,888
- Beds: 4 | Baths: 3 | Square feet: 2,456
- See 1 Grant Ct, Highland Mills, NY 10930 on Redfin.com
2 Hallock Ct, Highland Mills, NY 10930
- List price: $749,000
- Beds: 4 | Baths: 2.5 | Square feet: 3,040
- See 2 Hallock Ct, Highland Mills, NY 10930 on Redfin.com
33 Sutherland Dr, Highland Mills, NY 10930
- List price: $739,900
- Beds: 4 | Baths: 2.5 | Square feet: 2,434
- See 33 Sutherland Dr, Highland Mills, NY 10930 on Redfin.com
381 Route 32, Central Valley, NY 10917
- List price: $625,000
- Beds: 5 | Baths: 3.5 | Square feet: 1,952
- See 381 Route 32, Central Valley, NY 10917 on Redfin.com
#3. Knapps Corner (Wappinger, NY)
Median sale price: $470,000 | Median days on market: 25 days10 Lori St, Poughkeepsie, NY 12603
- List price: $430,000
- Beds: 4 | Baths: 1.5 | Square feet: 1,525
- See 10 Lori St, Poughkeepsie, NY 12603 on Redfin.com
35 Wildwood Dr, Poughkeepsie, NY 12603
- List price: $555,000
- Beds: 3 | Baths: 2 | Square feet: 1,700
- See 35 Wildwood Dr, Poughkeepsie, NY 12603 on Redfin.com
43 Briarcliff Ave, Poughkeepsie, NY 12603
- List price: $490,000
- Beds: 3 | Baths: 1.5 | Square feet: 2,529
- See 43 Briarcliff Ave, Poughkeepsie, NY 12603 on Redfin.com
608 Vassar Rd, Poughkeepsie, NY 12603
- List price: $519,999
- Beds: 4 | Baths: 3 | Square feet: not available
- See 608 Vassar Rd, Poughkeepsie, NY 12603 on Redfin.com
#4. College Hill (Poughkeepsie, NY)
Median sale price: $326,250 | Median days on market: 46 days108 Winnikee Ave, Poughkeepsie, NY 12601
- List price: $700,000
- Beds: 9 | Baths: 3 | Square feet: 3,588
- See 108 Winnikee Ave, Poughkeepsie, NY 12601 on Redfin.com
11 Howard St, Poughkeepsie, NY 12601
- List price: $195,000
- Beds: 4 | Baths: 1.5 | Square feet: 1,248
- See 11 Howard St, Poughkeepsie, NY 12601 on Redfin.com
15 Thompson St, Poughkeepsie, NY 12601
- List price: $360,000
- Beds: 3 | Baths: 2 | Square feet: 3,145
- See 15 Thompson St, Poughkeepsie, NY 12601 on Redfin.com
34 Smith St, Poughkeepsie, NY 12601
- List price: $365,000
- Beds: 3 | Baths: 2 | Square feet: 2,200
- See 34 Smith St, Poughkeepsie, NY 12601 on Redfin.com
#5. East End Historic District (Newburgh, NY)
Median sale price: $320,000 | Median days on market: 60 days12 Liberty St, Newburgh, NY 12550
- List price: $499,000
- Beds: 4 | Baths: 3 | Square feet: 3,650
- See 12 Liberty St, Newburgh, NY 12550 on Redfin.com
172 Chambers St, Newburgh, NY 12550
- List price: $399,000
- Beds: 7 | Baths: 3 | Square feet: 2,508
- See 172 Chambers St, Newburgh, NY 12550 on Redfin.com
37 Lutheran St, Newburgh, NY 12550
- List price: $300,000
- Beds: 4 | Baths: 2 | Square feet: 1,666
- See 37 Lutheran St, Newburgh, NY 12550 on Redfin.com
66 Benkard Ave, Newburgh, NY 12550
- List price: $369,900
- Beds: 4 | Baths: 2 | Square feet: 1,350
- See 66 Benkard Ave, Newburgh, NY 12550 on Redfin.com
