Orange County, NY Homes

/24
$679,900 Pending
- 5 Beds
- 2.5 Baths
- 3,538 Sq Ft
74 Red Maple Way, New Windsor, NY 12553

Welcome to 74 Red Maple Way at Windsor Woods, one of New Windsor’s premier cul-de-sac communities. At this stuning home elegance, comfort, and modern sophistication come together to create more than just a house—it’s a lifestyle. Step inside and you’ll be greeted by soaring ceilings, gleaming hardwood floors, and natural light pouring through oversized windows. The open-concept design flows

Randolph Rogers

eXp Realty

(845) 712-4003

74 Red Maple Way, New Windsor, NY 12553
/17
$2,500 Per Month
- 3 Beds
- 1.5 Baths
- 1,428 Sq Ft
- House for Rent
10 Chaucer Ct, Middletown, NY 10941

Located in the desirable Pine Bush School District, this well-maintained rental is ready for immediate occupancy! This spacious home offers three bedrooms and 1.5 bathrooms with a functional layout perfect for comfortable living.The first level features tile flooring throughout, a beautifully updated galley kitchen, a designated dining area, and a large living room filled with natural light.

Hazel Cello

Keller Williams Hudson Valley

(329) 209-8776

10 Chaucer Ct, Middletown, NY 10941
$285,000 Sold Oct 01, 2025

512 Riley Rd, New Windsor, NY 12553
- 3 Beds
- 1 Bath
- 960 Sq Ft
- Built 1973
Last Sold Summary
- 3% Below List Price
- $297/SF
- 66 Days On Market
Current Estimated Value $309,853

Last Listing Agent Arafat Ibrahim AI Realty Brokerage LLC

512 Riley Rd, New Windsor, NY 12553

Est $581,475 Not Listed For Sale

2 Strasser Place, Campbell Hall, NY 10916
- 2 Beds
- 2.5 Baths
- 2,752 Sq Ft
- Built 2018
2 Strasser Place, Campbell Hall, NY 10916

Last Sold Summary
- 8% Above List Price
- $195/SF
- 48 Days On Market
- Last Sold Price $538,000
- Aug 03, 2024
Last Listing Agent Frank Muccari Cronin & Company Real Estate

/48
$1,680,000
- 6 Beds
- 4.5 Baths
- 5,450 Sq Ft
395 Sarah Wells Trail, Goshen, NY 10924

Welcome to Twin Oaks – A Masterfully Restored Hudson Valley Estate.Nestled along one of the most scenic and desirable roads in the Hudson Valley, Twin Oaks is a truly exceptional residence, offering a rare blend of historic grandeur and modern refinement. Set on a tranquil, park-like 8.2-acre estate at the edge of the charming Village of Goshen, this stately French Second Empire Late

Joseph Paoli

Howard Hanna Rand Realty

(845) 400-8382

395 Sarah Wells Trail, Goshen, NY 10924
/50
Starting at $2,400 Per Month
- 1 - 2 Beds
1200 Regency Ct, Middletown, NY 10940

The Regency Club offers spacious living and dining areas, and modern kitchens in one bedroom with den and two bedroom floor plans. Apartments boast 9 ft. ceilings, ceramic tiles in the bathrooms and kitchens and a full appliance package. Residents enjoy the clubhouse, outdoor pool, state-of-the-art fitness center, and expansive club room as well as the outdoor tennis court and playground. The

The Regency Club

(845) 415-6883

1200 Regency Ct, Middletown, NY 10940
/26
$1,031,840 Sold Dec 22, 2025

20 Aurora Terrace, Tuxedo Park, NY 10987
- 4 Beds
- 3.5 Baths
- 2,936 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $351/SF
- 16 Days On Market
Lennar Tuxedo Reserve - Classic at West Terrace

20 Aurora Terrace, Tuxedo Park, NY 10987

Not Listed For Sale

69 Jessup Switch Rd, Goshen, NY 10924
- 2 Beds
- 1 Bath
- 1,148 Sq Ft
- Built 1880
69 Jessup Switch Rd, Goshen, NY 10924

Last Sold Summary
- $235/SF
- 220 Days On Market
- Last Sold Price $270,000
- Apr 17, 2023
Last Listing Agent Julianna Green BHG Real Estate Green Team

/36
$449,900 Pending
- 3 Beds
- 2 Baths
- 1,744 Sq Ft
11 5th Ave, Newburgh, NY 12550

You know the exhale. The one that happens somewhere past the Tappan Zee, when the skyline finally disappears from your rearview and the river gets wider and the trees get taller and your jaw — quietly, without you noticing — stops clenching. That exhale has a home now. Open the door and the house greets you the way old friends do — low-lit, warm, unhurried. Beamed ceilings run overhead like

Brian Caplicki

Keller Williams Hudson Valley

(845) 583-1443

11 5th Ave, Newburgh, NY 12550
/24
$2,450 Per Month
- 1 Bed
- 1 Bath
- 850 Sq Ft
- Apartment for Rent
28 Haines Ln Unit A, Walden, NY 12586

Discover this unique & stunning new apartment in Montgomery w/garage! Nestled in a serene neighborhood w/breathtaking mountain views, this newly built, apartment offers a tranquil retreat.Located just 14.7 miles from the Metro North Beacon train station, 4 miles from Interstate 84,& 8.3 miles from NYS Route 87, it provides convenient access to major routes. Situated atop a peaceful cul-de-sac,

Richard Baxter

Keller Williams Realty

(329) 777-6024

28 Haines Ln Unit A, Walden, NY 12586
$217,500 Sold Oct 28, 2025

59 Orchard Trail, Monroe, NY 10950
- 2 Beds
- 1 Bath
- 850 Sq Ft
- Built 1940
Last Sold Summary
- 9% Below List Price
- $256/SF
- 180 Days On Market
Current Estimated Value $225,714

Last Listing Agent Michelle Ayala BHHS Hudson Valley Properties

59 Orchard Trail, Monroe, NY 10950

Est $241,191 Not Listed For Sale

1 Lexington Hill Unit 8, Harriman, NY 10926
- 2 Beds
- 2 Baths
- 960 Sq Ft
- Built 1985
1 Lexington Hill Unit 8, Harriman, NY 10926

Last Sold Summary
- 3% Above List Price
- $245/SF
- 17 Days On Market
- Last Sold Price $235,000
- Aug 20, 2024
Last Listing Agent Kamal Khan Charles Rutenberg Realty, Inc.

/19
$285,000
- 2 Beds
- 1 Bath
- 1,020 Sq Ft
59 Country Club Dr, Florida, NY 10921

Welcome to this inviting home in the charming Village of Florida. Newly updated flooring and a freshly painted living room create a bright, refreshed atmosphere that’s ready to enjoy from day one.Set within a desirable community, residents have access to an impressive array of amenities designed for both relaxation and recreation, including a pool, hot tub, clubhouse, fitness center, sauna,

Luanne McGann

Century 21 Full Service Realty

(845) 614-9302

59 Country Club Dr, Florida, NY 10921
/46
Starting at $1,720 Per Month
- 1 - 2 Beds
2 Underhill Rd, Middletown, NY 10940

Living at Sutton Hill located in Middletown, NY, provides you with the peaceful, pastoral setting of the Catskill's and the Pocono's, and only an hour away from New York City.Convenient to the Metro North RR, near Orange Regional Medical center - schools, shopping and entertainment, all at your fingertips.Relax and enjoy our great amenities: Fitness Center, Pool, Playground,

Sutton Hill Apartments

(845) 415-7703

2 Underhill Rd, Middletown, NY 10940
$447,000 Sold Jul 21, 2025

14 Old Dominion Rd, Blooming Grove, NY 10914
- 3 Beds
- 2 Baths
- 2,142 Sq Ft
- Built 1920
Last Sold Summary
- 10% Below List Price
- $209/SF
- 279 Days On Market
Current Estimated Value $492,940

Last Listing Agent Kelly Beary Keller Williams Realty

14 Old Dominion Rd, Blooming Grove, NY 10914

Est $541,894 Not Listed For Sale

5 Highland Terrace, Newburgh, NY 12550
- 5 Beds
- 3 Baths
- 3,152 Sq Ft
- Built 1887
5 Highland Terrace, Newburgh, NY 12550

Last Sold Summary
- 13% Above List Price
- $152/SF
- 54 Days On Market
- Last Sold Price $480,000
- Aug 29, 2023
Last Listing Agent Alicia Goldman Christie's Int. Real Estate

/30
$449,900 Pending
- 3 Beds
- 2.5 Baths
- 1,714 Sq Ft
1 High St, Port Jervis, NY 12771

Charming new construction A-Frame with Modern Comforts. Welcome home to this stunning 3-bedroom, 2.5-bath A-frame residence, where cozy character meets modern convenience. Designed with an open-concept layout, the main level features a bright and airy living and dining room combination, highlighted by a warm fireplace that creates the perfect gathering space. The well-appointed kitchen with

Chris Ogden

Realty Promotions Inc

(845) 851-0574

1 High St, Port Jervis, NY 12771
/21
$2,250 Per Month
- 2 Beds
- 1 Bath
- 935 Sq Ft
- Apartment for Rent
306 Bluestone Ct Unit 216, Maybrook, NY 12543

Beautiful Corner Unit – 2 Bedroom, 1 Bath – Exclusive 55+ Community Don’t miss this rare chance to lease a never corner unit in a modern, one-year-old building at Bluestone Parc’s sought-after 55+ active adult community. This bright residence features 10-foot ceilings, an open layout, and a stylish kitchen with quartz countertops, an oversized peninsula, and quality appliances. Oversized windows

Ewa Kusmierek

eXp Realty

(845) 460-1639

306 Bluestone Ct Unit 216, Maybrook, NY 12543
$170,000 Sold Jun 27, 2025

156 School House Rd, Middletown, NY 10940
- 3 Beds
- 1 Bath
- 924 Sq Ft
- Built 1970
Last Sold Summary
- $184/SF
- 62 Days On Market
Last Listing Agent Tracy McNamara Keller Williams Realty

156 School House Rd, Middletown, NY 10940

Not Listed For Sale

348 Liberty St, Newburgh, NY 12550
- 13 Beds
- 7 Baths
- 5,200 Sq Ft
- Built 1900
348 Liberty St, Newburgh, NY 12550

Last Sold Summary
- $120/SF
- 236 Days On Market
- Last Sold Price $625,000
- Jun 05, 2023
Last Listing Agent Aryeh Moster Keller Williams Hudson Valley

/47
$570,000 Pending
- 4 Beds
- 3.5 Baths
- 2,072 Sq Ft
572 Greenville Turnpike, Middletown, NY 10940

Set back from the road, where life feels just a little more private and peaceful, there is a home that invites you to slow down... and stay awhile. Follow the charming brick path as it leads you to the front porch and into a space that immediately feels warm, welcoming, and filled with light. This move-in ready, Colonial home, offers a layout that simply makes sense for the way you want to live

Brian Caplicki

Keller Williams Hudson Valley

(329) 210-1675

572 Greenville Turnpike, Middletown, NY 10940
/35
Starting at $1,895 Per Month
- 1 - 2 Beds
2201 Vails Gate Heights Dr, New Windsor Township, NY 12553

Welcome to Mountainview VillageMountain View Village is a serene and inviting community nestled on 10 acres of beautifully landscaped grounds with stunning mountain views. Located just minutes from the vibrant Newburgh waterfront, Stewart National Airport, and the world-renowned Woodbury Commons Premium Outlets, Mountainview Village offers the perfect blend of peaceful living and

Mountainview Village

(845) 614-9382

2201 Vails Gate Heights Dr, New Windsor Township, NY 12553
$405,000 Sold Aug 19, 2025

6 Park Hill Dr, New Windsor, NY 12553
- 3 Beds
- 1 Bath
- 1,100 Sq Ft
- Built 1958
Last Sold Summary
- 8% Above List Price
- $368/SF
- 16 Days On Market
Current Estimated Value $412,223

Last Listing Agent Federico Prada RE/MAX Benchmark Realty Group

6 Park Hill Dr, New Windsor, NY 12553

Est $771,524 Not Listed For Sale

147 Elise Dr, Middletown, NY 10941
- 5 Beds
- 3.5 Baths
- 2,960 Sq Ft
- Built 2024
147 Elise Dr, Middletown, NY 10941

Last Sold Summary
- 1% Above List Price
- $258/SF
- 24 Days On Market
- Last Sold Price $763,846
- Aug 22, 2024
Last Listing Agent Juan Bautista Serhant LLC

/48
$1,499,900 Pending
- 4 Beds
- 4.5 Baths
- 4,620 Sq Ft
24 Heritage Ct, Tuxedo Park, NY 10987

In a market full of beautiful houses, this Hamilton Estates colonial stands apart for one simple reason. It delivers a way of living that feels complete the moment you arrive. This is not a home you have to imagine yourself growing into. It already meets you where you are. From the full length front porch that encourages slower mornings and easy conversations, to the light filled interior that

Brian Caplicki

Keller Williams Hudson Valley

(845) 458-8995

24 Heritage Ct, Tuxedo Park, NY 10987
/22
$2,300 Per Month
- 2 Beds
- 1 Bath
- 984 Sq Ft
- Condo for Rent
1 Ruth Ct, Middletown, NY 10940

Welcome to this beautifully updated and spacious first floor corner condo in Middletown, NY. This well-maintained home offers comfortable one level living with a large living room, two generously sized bedrooms, and one full bath. The modern walk-through kitchen features new stainless steel appliances and an adjacent dining area. Wall A/C units in the living room and both bedrooms provide

Kathy White

Exit Realty Connections

(329) 209-8678

1 Ruth Ct, Middletown, NY 10940
$375,000 Sold Nov 11, 2025

520 Shore Dr, New Windsor, NY 12553
- 3 Beds
- 1 Bath
- 960 Sq Ft
- Built 1948
Last Sold Summary
- 6% Below List Price
- $391/SF
- 78 Days On Market
Current Estimated Value $377,416

Last Listing Agent Matthew O'Hare Coldwell Banker Realty

520 Shore Dr, New Windsor, NY 12553

Est $800,592 Not Listed For Sale

2 Howard Ct, Goshen, NY 10924
- 4 Beds
- 3.5 Baths
- 3,352 Sq Ft
- Built 2012
2 Howard Ct, Goshen, NY 10924

Last Sold Summary
- 10% Above List Price
- $216/SF
- 68 Days On Market
- Last Sold Price $725,000
- Jan 02, 2025
Last Listing Agent Jason Dillon eXp Realty

/32
$1,700,000
- 5 Beds
- 9 Baths
- 7,794 Sq Ft
3 Bristol Dr, Middletown, NY 10941

PRICE REDUCTION FOR FASTER SALE...OWNER RELOCATING.....HURRY UP....WILL NOT LAST.............................Welcome to 3 Bristol Road, a rare brick colonial estate set on 1.4 private acres, offering nearly 8,000 Sqft of living space plus a spectacular 3,200-square-foot indoor pool pavilion designed for year-round enjoyment.Built in 2002, this 6-bedroom, 8.55-bathroom residence features

Mohamed Elgoarany

All American Realty Management

(329) 215-0309

3 Bristol Dr, Middletown, NY 10941
/15
Starting at $783 Per Month
- 1 Bed
5 N Main St, Monroe, NY 10950

Our Monroe apartments offer a comfortable yet stylish lifestyle right in the heart of the community. With a wide range of amenities and an efficient room plan, each airy one-bedroom apartment provides the perfect solution for comfortable senior living.Known for its heritage as the birthplace of Velveeta and Liederkranz cheeses, Monroe is the host each year of a popular Cheese Festival

Monroe Commons

(845) 604-9364

5 N Main St, Monroe, NY 10950
$482,500 Sold Oct 06, 2025

39 Brookline Ave, Middletown, NY 10940
- 3 Beds
- 2.5 Baths
- 1,872 Sq Ft
- Built 2005
Last Sold Summary
- 2% Below List Price
- $258/SF
- 26 Days On Market
Current Estimated Value $478,512

Last Listing Agent Andrea Rose Keller Williams Hudson Valley

39 Brookline Ave, Middletown, NY 10940

Est $572,275 Not Listed For Sale

426 Maple Hill Dr, Cornwall, NY 12518
- 4 Beds
- 3.5 Baths
- 2,671 Sq Ft
- Built 1965
426 Maple Hill Dr, Cornwall, NY 12518

Last Sold Summary
- 4% Above List Price
- $206/SF
- 229 Days On Market
- Last Sold Price $550,000
- Feb 20, 2025
Last Listing Agent Christina Wilger RE/MAX Benchmark Realty Group

/50
$568,000
- 7 Beds
- 4.5 Baths
- 3,592 Sq Ft
104-108 Highland Ave, Middletown, NY 10940

Historic Elegance Meets Modern-Day Convenience in this circa 1860 home in the heart of Middletown, NY. Pristinely positioned back from the road, set on just shy of an acre, this historic gem offers 3500+ square feet of timeless character and space. From the moment you enter, soaring ceilings, rich hardwood floors, built-ins and detailed crown molding set the tone. The expansive dining room,

JoAnn Maxwell

Howard Hanna Rand Realty

(329) 210-1132

104-108 Highland Ave, Middletown, NY 10940
/20
$2,000 Per Month
- 1 Bed
- 1 Bath
- Apartment for Rent
514 Grand Ave, Newburgh, NY 12550

Charming 1 Bedroom Victorian Apartment with Hudson River Views in Balmville Bright and quaint, larger one bedroom, one bath apartment in a beautiful 1800s Victorian multi family home. Enjoy stunning Hudson River and bridge views along the entire east side and peaceful sunrises. Features include hardwood floors, a small kitchen, dining room, large living room. This end unit is in a quiet setting

Jodi Gillespie

GILLESPIE REAL ESTATE LLC

(845) 668-6985

514 Grand Ave, Newburgh, NY 12550
$472,000 Sold Dec 30, 2025

87 Barr Ln, Monroe, NY 10950
- 3 Beds
- 2.5 Baths
- 1,671 Sq Ft
- Built 2004
Last Sold Summary
- 2% Above List Price
- $282/SF
- 26 Days On Market
Current Estimated Value $485,045

Last Listing Agent Robert Mahling Howard Hanna Rand Realty

87 Barr Ln, Monroe, NY 10950

Not Listed For Sale

19 Ethel Dr, Cornwall, NY 12518
- 5 Beds
- 3.5 Baths
- 5,082 Sq Ft
- Built 1992
19 Ethel Dr, Cornwall, NY 12518

Last Sold Summary
- $323/SF
- 198 Days On Market
- Last Sold Price $1,640,000
- May 10, 2023
Last Listing Agent Alicia Goldman Christie's Int. Real Estate

/22
$134,900 Pending
- 1 Bed
- 1 Bath
- 960 Sq Ft
10 Oakwood Terrace Unit 110, New Windsor, NY 12553

Top floor, Spacious and sun-filled 1-bedroom, 1-bath end unit co-op offering 960 square feet of comfortable living. Located in a well-maintained complex, this corner unit features a private balcony, ideal for relaxing or entertaining. Enjoy access to a community pool and beautifully landscaped grounds, all within a quiet neighborhood setting. A commuter’s dream just minutes from both I-84 and

RoseMarie Christner

Stepping Stone Realty

(845) 316-0718

10 Oakwood Terrace Unit 110, New Windsor, NY 12553
/35
Starting at $1,775 Per Month
- 1 - 2 Beds
507 Sherwood Dr N, Middletown, NY 10941

Sherwood Forest Garden Apartments, located in Middletown, NY, consists of six garden apartment-style buildings spread over 18 lushly landscaped acres. Your rent includes Heat/AC, Hot Water, Cooking Gas, and Trash. In addition, there is an outdoor pool, with an adjacent fitness center, BBQ Grills and Unassigned Parking. ALL are available, without charge, to residents of the property. Ground level

Sherwood Forest Garden Apartments

(845) 415-6404

507 Sherwood Dr N, Middletown, NY 10941
$485,000 Sold Sep 05, 2025

45 W Main St, Washingtonville, NY 10992
- 4 Beds
- 2 Baths
- 2,020 Sq Ft
- Built 1930
Last Sold Summary
- 2% Below List Price
- $240/SF
- 99 Days On Market
Current Estimated Value $508,146

Last Listing Agent Jacqueline Manzolillo-Blais Keller Williams Realty

45 W Main St, Washingtonville, NY 10992

Not Listed For Sale

6 Rivercrest Rd, Fort Montgomery, NY 10922
- 3 Beds
- 2 Baths
- 1,721 Sq Ft
- Built 1971
6 Rivercrest Rd, Fort Montgomery, NY 10922

Last Sold Summary
- $210/SF
- 44 Days On Market
- Last Sold Price $361,000
- Apr 28, 2023
Last Listing Agent Vincent Breit Keller Williams Hudson Valley

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