- 3 bds
- 3 ba
- 2,128 sqft
LISTING BY: HOWARD HANNA RAND REALTY
Homes for Sale Under $500K in Middletown NY
124 results
- 5 Pilgrim Corners Road, Middletown, NY 10940
Showcase - 200 Mt Orange Road, Middletown, NY 10940
- 4 bds
- 4 ba
- 3,432 sqft
LISTING BY: HUDSON VALLEY GRIFFITH15 days on Zillow
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- 721 Goshen Turnpike, Circleville, NY 10919
- 3 bds
- 2 ba
- 1,451 sqft
LISTING BY: RE/MAX BENCHMARK REALTY GROUPOriginal details
- 542 Dosen Road, Middletown, NY 10940
- 2 bds
- 1 ba
- 826 sqft
LISTING BY: KELLER WILLIAMS REALTYDetached garage
- 4 Thistle Lane, Middletown, NY 10940
- 4 bds
- 3 ba
- 2,848 sqft
LISTING BY: HOWARD HANNA RAND REALTYShowcase 
- 5 Oak Ridge Road, Middletown, NY 10940
- 4 bds
- 3 ba
- 2,392 sqft
LISTING BY: REDFIN REAL ESTATE2 hours ago
- 4 Francis Drive, Middletown, NY 10940
- 4 bds
- 2 ba
- 2,188 sqft
LISTING BY: KELLER WILLIAMS REALTYOn Market Oct 15
- 311 Howells Road, Middletown, NY 10940
- 3 bds
- 1 ba
- 1,188 sqft
LISTING BY: HOWARD HANNA RAND REALTYOpen: Thu 4-6pm (10/15)
- 13 S Shore Drive, Middletown, NY 10940
- 4 bds
- 3 ba
- 2,544 sqft
LISTING BY: HOWARD HANNA RAND REALTYOpen: Sat 12-2pm (10/17)
- 21 Old Timers Road, Middletown, NY 10940
- 3 bds
- 2 ba
- 1,440 sqft
LISTING BY: HOWARD HANNA RAND REALTYFinished lower level
- 21 Willow Place, Middletown, NY 10940
- 3 bds
- 1 ba
- 1,032 sqft
LISTING BY: EREALTY ADVISORS, INC23 hours ago
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- 56 Scott Drive, Middletown, NY 10941
- 3 bds
- 2 ba
- 1,732 sqft
LISTING BY: KELLER WILLIAMS REALTYOn Market Oct 16
- 34 Chaucer Court, Middletown, NY 10941
- 3 bds
- 2 ba
- 1,428 sqft
LISTING BY: DIAMOND QUALITY REAL ESTATE5 days on Zillow
- 122 Castle High Road, Middletown, NY 10940
- 3 bds
- 1 ba
- 1,830 sqft
LISTING BY: CURASI REALTY, INC.Price cut: $24,001 (10/7)
- 23 days on Zillow
- 159 Wawayanda Avenue, Middletown, NY 10940
- 3 bds
- 2 ba
- 1,352 sqft
LISTING BY: CRONIN & COMPANY REAL ESTATEThree generously sized bedrooms
- 13 Birch Street, Middletown, NY 10940
- 2 bds
- 1 ba
- 432 sqft
LISTING BY: PICTURE IT SOLD, LLCPrice cut: $10,000 (9/15)
- 79 Stern Scenic Drive, Middletown, NY 10940
- 3 bds
- 2 ba
- 1,500 sqft
LISTING BY: EXIT REALTY CONNECTIONSModern touches
- Start survey
Help others discover what makes this area unique.
Fill out a short survey to help others know what it's like to live here. - 197 Deer Court Dr, Middletown, NY 10940
- 2 bds
- 3 ba
- 1,473 sqft
LISTING BY: STATEWIDE PROPERTIES LLC, Vitaly Isaacs. Listing provided by My State MLSOpen: Sun 1-3pm (10/25)
- 65 Maureen Drive, Middletown, NY 10940
- 3 bds
- 3 ba
- 2,200 sqft
LISTING BY: CRONIN & COMPANY REAL ESTATEPrivate backyard oasis
- 243 Howells Turnpike, Middletown, NY 10940
- 2 bds
- 1 ba
- 960 sqft
LISTING BY: HOMESMART HOMES & ESTATES19 days on Zillow
- Open: Sat 11am-1pm (10/17)
- 32 Abraham Joseph Cir #32, Middletown, NY 10940
- 3 bds
- 2 ba
- 1,232 sqft
LISTING BY: ELLIOTT AND POMEROY INC, Mary Hovanec. Listing provided by NY State MLS4 days on Zillow
- 50 Scott Drive, Middletown, NY 10941
- 4 bds
- 2 ba
- 1,796 sqft
LISTING BY: KW HUDSON VALLEY UNITEDExpansive backyard
- 25 Church Street, Howells, NY 10932
- 4 bds
- 2 ba
- 1,723 sqft
LISTING BY: REAL ESTATE CIRCUIT INCPrice cut: $20,000 (9/17)
- Beautiful outdoor space
- 30 Chestnut Avenue, Middletown, NY 10940
- 3 bds
- 2 ba
- 1,316 sqft
LISTING BY: CORCORAN BAER & MCINTOSHPrice cut: $10,000 (9/17)
- 45 Brola Road, Middletown, NY 10940
- 3 bds
- 3 ba
- 1,966 sqft
LISTING BY: KELLER WILLIAMS REALTYCozy wood-burning fireplace
- 960 Mt Hope Road, Middletown, NY 10940
- 4 bds
- 1 ba
- 1,306 sqft
LISTING BY: HANSON REAL ESTATE PARTNERSNewer roof
- 2195 Route 302, Circleville, NY 10919
- 2 bds
- 1 ba
- 1,058 sqft
LISTING BY: DIMATTEO REALTY LLCPrice cut: $14,000 (10/12)
- 6-8 Forest Avenue, Middletown, NY 10940
- 3 bds
- 3 ba
- 1,252 sqft
LISTING BY: HUDSON PREMIUM REALTYFlexible living spaces
- 13 Old Anvil Lane, Middletown, NY 10940
- 3 bds
- 3 ba
- 1,692 sqft
LISTING BY: HOWARD HANNA RAND REALTY34 days on Zillow
- 32 Tarbell Road, Bloomingburg, NY 12721
- 2 bds
- 1 ba
- 1,131 sqft
LISTING BY: KW HUDSON VALLEY UNITEDPrice cut: $14,901 (10/8)
- 15 Randall Heights, Middletown, NY 10940
- 3 bds
- 3 ba
- 1,976 sqft
LISTING BY: KW HUDSON VALLEY UNITEDNice level backyard
- 1040 Route 211 W, Middletown, NY 10940
- 3 bds
- 2 ba
- 960 sqft
LISTING BY: KELLER WILLIAMS REALTY13 days on Zillow
- 12 Westminster Drive, Middletown, NY 10940
- 4 bds
- 3 ba
- 1,848 sqft
LISTING BY: CENTURY 21 FULL SERVICE REALTYPrivate driveway
- 14 Columbia Avenue, Middletown, NY 10940
- 3 bds
- 1 ba
- 954 sqft
LISTING BY: KW HUDSON VALLEY UNITED6 days on Zillow
- 5 days on Zillow
- 11 Gardner Avenue, Middletown, NY 10940
- 3 bds
- 3 ba
- 1,676 sqft
LISTING BY: KW HUDSON VALLEY UNITEDEnclosed backyard
- 7 Allan Park Mews, Middletown, NY 10940
- 3 bds
- 2 ba
- 1,650 sqft
LISTING BY: CENTURY 21 FULL SERVICE REALTYOpen: Sun 12-2pm (10/18)
- 21 Fair Avenue, Middletown, NY 10940
- 2 bds
- 2 ba
- 1,360 sqft
LISTING BY: HOMESMART HOMES & ESTATES4 days on Zillow
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Based on information submitted to the MLS GRID as of 2026-10-14 12:48:21 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)
