- 6 bds
- 2 ba
- -- sqft
LISTING BY: MS REALTY GROUP USA, INC
55 days on Zillow
Chester NY Luxury Homes
74 results
- 68 Conklingtown Road #1&2, Chester, NY 10918
- 50 Hambletonian Avenue, Chester, NY 10918
- 3 bds
- 2 ba
- 1,583 sqft
LISTING BY: HOWARD HANNA RAND REALTYPrice cut: $29,900 (8/26)
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- 7 Lakeview Drive, Chester, NY 10918
- 4 bds
- 3 ba
- 2,098 sqft
LISTING BY: HOWARD HANNA RAND REALTYWoodburning fireplaces
- 3318 State Route 94, Chester, NY 10918
- 3 bds
- 2 ba
- 2,138 sqft
LISTING BY: HOWARD HANNA RAND REALTYExpansive primary suite
- 11 Chandler Drive, Chester, NY 10918
- 3 bds
- 3 ba
- 1,908 sqft
LISTING BY: COLDWELL BANKER REALTYPrice cut: $30,000 (8/21)
- 19 Meadow Avenue, Chester, NY 10918
- 2 bds
- 2 ba
- 1,910 sqft
LISTING BY: RE/MAX TOWN & COUNTRYOn Market Sep 19
- 24 Walnut Street, Chester, NY 10918
- 4 bds
- 3 ba
- 2,698 sqft
LISTING BY: KELLER WILLIAMS VILLAGE SQ RLTPrice cut: $14,000 (9/11)
- 5 N Hudson Street, Chester, NY 10918
- 3 bds
- 2 ba
- 2,688 sqft
LISTING BY: KELLER WILLIAMS REALTYPeaceful setting
- 264 Bull Mill Road, Chester, NY 10918
- 3 bds
- 3 ba
- 1,848 sqft
LISTING BY: KELLER WILLIAMS REALTYOn Market Sep 16
- 21 Trotting Drive, Chester, NY 10918
- 3 bds
- 2 ba
- 1,624 sqft
LISTING BY: KELLER WILLIAMS REALTYFully renovated kitchen
- Price cut: $14,000 (8/31)
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- Private loft
- 63 Hubshop Road, Chester, NY 10918
- 4 bds
- 3 ba
- 2,060 sqft
LISTING BY: KELLER WILLIAMS REALTY26 days on Zillow
- 8 Townsend Place, Chester, NY 10918
- 4 bds
- 2 ba
- 1,832 sqft
LISTING BY: HOWARD HANNA RAND REALTYShowcase 
- 66 Whitetail Run, Chester, NY 10918
- 3 bds
- 2 ba
- 1,500 sqft
LISTING BY: HOWARD HANNA RAND REALTYAttached one-car garage
- 1367 Kings Highway, Chester, NY 10918
- 3 bds
- 2 ba
- 1,728 sqft
LISTING BY: GREENE REALTY GROUPOriginal exposed hand-hewn beams
- 6 Old Dominion Road, Blooming Grove, NY 10914
- 4 bds
- 2 ba
- 2,116 sqft
LISTING BY: RE/MAX PRIME PROPERTIESFarmhouse character
- Scenic surroundings
- 4704 Whispering Hills, Chester, NY 10918
- 3 bds
- 3 ba
- 1,331 sqft
LISTING BY: SAHAGIAN REALTY LLCCozy fireplace
- 7 Hambletonian Avenue, Chester, NY 10918
- 2 bds
- 1 ba
- 1,026 sqft
LISTING BY: HOMESMART HOMES & ESTATESWood burning fireplace
- 2921 Whispering Hills, Chester, NY 10918
- 3 bds
- 3 ba
- 1,331 sqft
LISTING BY: ARC REALTY 1 IN SALESCentral air
- 260 Gibson Hill Road, Chester, NY 10918
- 3 bds
- 2 ba
- 1,644 sqft
LISTING BY: KELLER WILLIAMS REALTYPeaceful setting
- 3211 Whispering Hills, Chester, NY 10918
- 3 bds
- 2 ba
- 1,316 sqft
LISTING BY: RE/MAX BENCHMARK REALTY GROUP9 days on Zillow
- 3409 Whispering Hills, Chester, NY 10918
- 3 bds
- 3 ba
- 1,331 sqft
LISTING BY: HOWARD HANNA RAND REALTY25 days on Zillow
- 2522 Whispering Hills, Chester, NY 10918
- 3 bds
- 3 ba
- 1,331 sqft
LISTING BY: HOWARD HANNA RAND REALTYPrice cut: $10,000 (9/9)
- 241 Meadow Avenue, Chester, NY 10918
- 4 bds
- 2 ba
- 1,560 sqft
LISTING BY: KELLER WILLIAMS REALTY64 days on Zillow
- 151 Main Street, Chester, NY 10918
- 4 bds
- 1 ba
- 1,504 sqft
LISTING BY: HUDSON VALLEY GRIFFITHPrice cut: $26,000 (8/27)
- 2124 Whispering Hills, Chester, NY 10918
- 2 bds
- 1 ba
- 1,084 sqft
LISTING BY: HOWARD HANNA RAND REALTYShowcase 
- 552 Pine Hill Road, Chester, NY 10918
- 5.7 acres lot
LISTING BY: EREALTY ADVISORS, INCPeaceful private setting
- 1005 Whispering Hills, Chester, NY 10918
- 2 bds
- 2 ba
- 1,053 sqft
LISTING BY: CENTURY 21 FULL SERVICE REALTYCentral air conditioning
- 4008 Whispering Hills Drive, Chester, NY 10918
- 2 bds
- 2 ba
- 1,072 sqft
LISTING BY: HOWARD HANNA RAND REALTYCentral air
- 166 Bull Mill Road, Chester, NY 10918
- 2 bds
- 1 ba
- 1,004 sqft
LISTING BY: KELLER WILLIAMS VALLEY REALTYPrice cut: $51,000 (9/10)
- 2113 Whispering Hills, Chester, NY 10918
- 2 bds
- 1 ba
- 1,084 sqft
LISTING BY: KELLER WILLIAMS REALTYPrice cut: $20,000 (8/26)
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Based on information submitted to the MLS GRID as of 2026-09-14 14:48:13 PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. [Click here for more information](/mls-disclaimers/#778)
