Price cut: $15,000 (9/21)
Homes for Sale Under $500K in Orange County NY
560 results
- 72 Waterstone Road, Greenwood Lake, NY 10925
- 3 bds
- 2 ba
- 1,418 sqft
LISTING BY: RIVER REALTY SERVICES, INC.Hardwood flooring throughout
Loading...
- 113 days on Zillow
- 1836 State Route 52 Road, Walden, NY 12586
- 3 bds
- 3 ba
- 1,940 sqft
LISTING BY: CENTURY 21 E & M WILLIAMS RLTYSpacious parking area
- 50 Scott Drive, Middletown, NY 10941
- 4 bds
- 2 ba
- 1,796 sqft
LISTING BY: KW HUDSON VALLEY UNITEDExpansive backyard
- 38 Valley Avenue, Walden, NY 12586
- 4 bds
- 2 ba
- 1,440 sqft
LISTING BY: KELLER WILLIAMS REALTY7 days on Zillow
- 3 Magnolia Lane, Warwick, NY 10990
- 2 bds
- 3 ba
- 1,662 sqft
LISTING BY: KW HUDSON VALLEY UNITEDOn Market Oct 01
- 39 California Avenue, Middletown, NY 10940
- 4 bds
- 1 ba
- 1,204 sqft
LISTING BY: DALTON WADE REAL ESTATE GROUPPrice cut: $20,000 (9/22)
- 60 Higgins Trail, Monroe, NY 10950
- 2 bds
- 1 ba
- 1,200 sqft
LISTING BY: EXIT REALTY CONNECTIONS93 days on Zillow
- 555 State Route 416, Montgomery, NY 12549
- 4 bds
- 2 ba
- 1,734 sqft
LISTING BY: COLDWELL BANKER REALTYPrice cut: $20,000 (9/14)
- 51 S Shore Drive, Middletown, NY 10940
- 1 bd
- 1 ba
- 360 sqft
LISTING BY: EREALTY ADVISORS, INCBrand-new oversized deck
Loading...
- 129 Dubois Street, Pine Bush, NY 12566
- 3 bds
- 2 ba
- 1,680 sqft
LISTING BY: KELLER WILLIAMS REALTY11 days on Zillow
- Open: Sat 11am-1pm (9/26)
- 23 Pike Court, Monroe, NY 10950
- 3 bds
- 2 ba
- 2,460 sqft
LISTING BY: RE/MAX BENCHMARK REALTY GROUP56 days on Zillow
- 105 Vails Gate Heights Drive, New Windsor, NY 12553
- 3 bds
- 2 ba
- 1,887 sqft
LISTING BY: HOWARD HANNA RAND REALTYShowcase 
- Charming ranch
- Fresh well-cared-for appeal
- 241 Garden Street, New Windsor, NY 12553
- 3 bds
- 3 ba
- 1,812 sqft
LISTING BY: KW HUDSON VALLEY UNITEDOpen: Sun 1-3pm (10/4)
- 132 Sycamore Drive, Middletown, NY 10940
- 2 bds
- 2 ba
- 1,342 sqft
LISTING BY: CURASI REALTY, INC.3 days on Zillow
- 158 High Meadows Road, Walden, NY 12586
- 3 bds
- 3 ba
- 2,893 sqft
LISTING BY: KELLER WILLIAMS REALTY45 days on Zillow
- 57 Keats Drive, New Windsor, NY 12553
- 3 bds
- 2 ba
- 1,704 sqft
LISTING BY: RE/MAX BENCHMARK REALTY GROUPModern updates throughout
- Plenty of outdoor space
- 19 Railroad Avenue, Walden, NY 12586
- 2 bds
- 1 ba
- 1,168 sqft
LISTING BY: KELLER WILLIAMS REALTYOpen: Sat 12-2pm (9/26)
- 2301 Barclay Manor #23A, Newburgh, NY 12550
- 1 bd
- 1 ba
- 515 sqft
LISTING BY: KW HUDSON VALLEY UNITEDComfortable bedroom
- 63 Hubshop Road, Chester, NY 10918
- 4 bds
- 3 ba
- 2,060 sqft
LISTING BY: KELLER WILLIAMS REALTY37 days on Zillow
- 22 days on Zillow
- 4 Ram Road, Salisbury Mills, NY 12577
- 3 bds
- 2 ba
- 1,342 sqft
LISTING BY: HOWARD HANNA RAND REALTYOpen: Sat 12-2pm (9/26)
- 11 Gardner Avenue, Middletown, NY 10940
- 3 bds
- 3 ba
- 1,676 sqft
LISTING BY: KW HUDSON VALLEY UNITEDEnclosed backyard
- 104 Canal Drive, Godeffroy, NY 12729
- 3 bds
- 2 ba
- 1,596 sqft
LISTING BY: HOMES BY YARA REALTY GROUP LLCPrice cut: $13,010 (9/3)
- Washer and dryer closet
- 25 Sylvan Trail, Monroe, NY 10950
- 3 bds
- 1 ba
- 960 sqft
LISTING BY: HOWARD HANNA RAND REALTYShowcase 
- 276 Temple Hill Road #207, New Windsor, NY 12553
- 3 bds
- 2 ba
- 1,512 sqft
LISTING BY: RE/MAX BENCHMARK REALTY GROUPWasher and dryer
- Cozy fireplace
- Open: Sat 1-3pm (9/26)
- 68 Kennel Road, Cuddebackville, NY 12729
- 3 bds
- 2 ba
- 1,536 sqft
LISTING BY: KW HUDSON VALLEY UNITEDPrice cut: $13,000 (9/14)
- 45 Brola Road, Middletown, NY 10940
- 3 bds
- 3 ba
- 1,966 sqft
LISTING BY: KELLER WILLIAMS REALTYCozy wood-burning fireplace
- 10 Andre Drive, Highland Mills, NY 10930
- 4 bds
- 2 ba
- 1,884 sqft
LISTING BY: OPULENCE REALTY GROUPOpen: Sat 11am-3pm (9/26)
- 31 Mt Hope Avenue, Otisville, NY 10963
- 3 bds
- 2 ba
- 1,695 sqft
LISTING BY: CRONIN & COMPANY REAL ESTATEPrice cut: $15,000 (9/9)
- 83 Center Street, Highland Falls, NY 10928
- 2 bds
- 1 ba
- 816 sqft
LISTING BY: RE/MAX BENCHMARK REALTY GROUPFull unfinished walk-out basement
- 11 Kevin Court, Montgomery, NY 12549
- 4 bds
- 3 ba
- 2,288 sqft
LISTING BY: HUDSON VALLEY GRIFFITHNewer roof
- 368 Old Dutch Hollow Road, Greenwood Lake, NY 10925
- 2 bds
- 1 ba
- 1,184 sqft
LISTING BY: RE/MAX TOWN & COUNTRYDistinctive architectural details
to get email alerts when listings hit the market.
IDX information © 2026 by the Hudson Valley Catskill Region MLS. All Rights Reserved. The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS. Information is deemed reliable but is not guaranteed accurate by the MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of 2026-09-25 23:58:10 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)
