The Most Expensive Neighborhoods in Poughkeepsie

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The most expensive neighborhoods in Poughkeepsie

Homebuyers and sellers are navigating a slow and expensive housing market, with rising prices and stagnant demand on the sidelines. This comes amid rising and growing . But luxury homes—multimillion-dollar estates, sleek penthouses, and one-of-a-kind custom builds—are , 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 days

16 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

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

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

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

#2. Highland Mills (Woodbury, NY)

Median sale price: $522,500 | Median days on market: 35 days

1 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

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

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

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

#3. Knapps Corner (Wappinger, NY)

Median sale price: $470,000 | Median days on market: 25 days

10 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

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

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

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

#4. College Hill (Poughkeepsie, NY)

Median sale price: $326,250 | Median days on market: 46 days

108 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

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

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

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