Vintage homes for sale & real estate in Orange County, NY

439 homes

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ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Discover a prime investment opportunity in the heart of Newburgh’s exciting revitalization at 119 Chambers Street. This well-maintained three-family property offers both solid rental income and future growth potential in one of the Hudson Valley’s most promising markets. With a desirable location directly across from a park and just minutes from Newburgh’s renowned waterfront, this property appeals to both investors and owner-occupants alike. The building consists of two spacious 2-bedroom, 1-bath units and one 3-bedroom, 1-bath unit, providing flexible living arrangements for tenants or extended family. One of the units is currently vacant, creating an outstanding opportu

$465,564

7 beds3 baths2,397 sq ft

119 Chambers St, Newburgh, NY 12550

Strong cash flow • Across from park • Prime location

Listing by Your Move Matters LLC

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Attached brick Legal three family in need of interior repair. Brand new heating system on all three floors. New electric panels, all individualized. Perfect for buyers looking to capitalize on a wonderful investment opportunity. Plenty of original details. Completely vacant. Motivated seller.

$399,900

6 beds3 baths2,573 sq ft

298 Liberty St #3, Newburgh, NY 12550

Electric panels • Original details • Heating system

Listing by Douglas Elliman Real Estate

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Welcome to Your Upstate NY Retreat. This clean modernized studio home comes with a sprawling 1.2 acres and a giant shed (for some upstate toys). The home was renovated and furnished with all stainless-steel appliances as well as hardwood flooring and concrete countertops. Home is ready for You located in the center of Orange County NY and only minutes from Woodbury Commons Shopping, Lego Land, Hudson Valley Resorts casino, Storm King Art Center, West Point, NY Stewart International Airport, Motorcyclopedia Museum, Purple Heart Museum, Hudson River Waterfront, George Washingtons Headquarters. .. .or go 5 miles up the road where You can Hike, Fish, Hunt, Horseback ride, Ski and Snowmobile at

$240,000

1 bed1 bath520 sq ft

2323 State Route 207, Campbell Hall, NY 10916

Hardwood flooring • 1.2 acres • Giant shed

Listing by Keller Williams Realty

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Nestled on 1.3 acres of private property not far from the village of Monroe, this home features a oversized living room with rustic stone fireplace with pellet insert! Large eat in kitchen with doors to private deck! To the right of the kitchen is the dining room with stone fireplace. To the right of the entry there is a bright large room that can be used as a possible mother/daughter, full bath and a bedroom, possible hook up for washer dryer or a utility sink. On the second level there are 5 bedrooms, original hardwood flooring - master has wall to wall walk in closet. Full bath off the hallway! There is recessed lighting in the living room, kitchen, hallway and other various rooms thr

$425,000

5 beds2 baths2,950 sq ft

116 Ludlum Rd, Monroe, NY 10950

Private deck • 1.3 acre lot • Garage

Listing by Keller Williams Hudson Valley

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Absolutely Stunning Second Empire Victorian with beautiful Hudson River Views! Just 60 miles from NYC, this 1884 architectural treasure (on the National Register of Historic Places) is remarkably original, yet has the modern upgrades that make it a pleasure to live in today. Whether you are enjoying the Hudson River views, the surrounding historic homes, or the historically rich details inside the home, there is beauty to take in everywhere you look. It was designed by architect Elkanah Shaw (whose family also produced all of the millwork for the home) for one of Newburgh's economic leaders of the day (see the last listing photo) - and as director of the Edison Electric Illuminating Company

$999,000

9 beds4 baths5,406 sq ft

168 Grand St, Newburgh, NY 12550

7 fireplaces • 200a electric system • Hudson river views

Listing by Hanson Real Estate Partners

Property at 20 Benton Ave, Middletown, NY 10940, 3 beds, 2 baths

$324,999

3 beds2 baths1,504 sq ft

20 Benton Ave, Middletown, NY 10940

Listing by Keller Williams Realty

Property at 2444 State Route 52, Pine Bush, NY 12566, 3 beds, 2 baths

$375,000

3 beds2 baths1,100 sq ft

2444 State Route 52, Pine Bush, NY 12566

Listing by Real Estate Circuit Inc

Property at 33 Mailler Ave, Cornwall, NY 12518, 3 beds, 2 baths

$429,000

3 beds2 baths1,165 sq ft

33 Mailler Ave, Cornwall, NY 12518

Listing by Capital Estate Realty LLC

Property at 17 Hillside Rd, Greenwood Lake, NY 10925, 3 beds, 1 bath

$499,000

3 beds1 bath2,136 sq ft

17 Hillside Rd, Greenwood Lake, NY 10925

Listing by Wansor Realty

Property at 23 City Ter Unit A, Newburgh, NY 12550, 5 beds, 2 baths

$299,888

5 beds2 baths1,952 sq ft

23 City Ter Unit A, Newburgh, NY 12550

Listing by John J Lease REALTORS Inc

Property at 180 Ann St, Newburgh, NY 12550, 7 beds, 2 baths

$154,900

7 beds2 baths1,596 sq ft

180 Ann St, Newburgh, NY 12550

Listing by River Realty Services, Inc.

Property at 20 N Main St, Monroe, NY 10950, 3 beds

$500,000

3 beds— baths1,272 sq ft

20 N Main St, Monroe, NY 10950

Listing by Master Realty Group Inc.

Property at 77 Prospect St, Newburgh, NY 12550, 3 beds, 2 baths

$435,000

3 beds2 baths1,242 sq ft

77 Prospect St, Newburgh, NY 12550

Listing by Christie's Int. Real Estate

Property at 11 Queen St, New Windsor, NY 12553, 5 beds, 3 baths

$469,999

5 beds3 baths2,400 sq ft

11 Queen St, New Windsor, NY 12553

Listing by HomeSmart Homes & Estates

Property at 46 Woodland Rd, Monroe, NY 10950, 4 beds, 3.5 baths

$839,000

4 beds3.5 baths3,235 sq ft

46 Woodland Rd, Monroe, NY 10950

Listing by Empire Fine Homes

Property at 9 Genung St, Middletown, NY 10940, 3 beds, 2 baths

$299,999

3 beds2 baths1,240 sq ft

9 Genung St, Middletown, NY 10940

Listing by Keller Williams Hudson Valley

Property at 6 Brooks Ave, Monroe, NY 10950, 3 beds, 1 bath

$415,000

3 beds1 bath1,056 sq ft

6 Brooks Ave, Monroe, NY 10950

Listing by eRealty Advisors, Inc

Property at 27 Windermere Ave, Greenwood Lake, NY 10925, 3 beds, 2 baths

$599,000

3 beds2 baths1,600 sq ft

27 Windermere Ave, Greenwood Lake, NY 10925

Listing by ARC Realty 1 in Sales

Property at 311 Tower Ave, Maybrook, NY 12543, 2 beds, 1 bath

$157,000

2 beds1 bath714 sq ft

311 Tower Ave, Maybrook, NY 12543

Listing by Keller Williams Realty

Property at 23 Rabbit Hill Rd, Monroe, NY 10950, 4 beds, 3 baths

$799,000

4 beds3 baths1,716 sq ft

23 Rabbit Hill Rd, Monroe, NY 10950

Listing by Howard Hanna Rand Realty

Property at 11 Russell St, Cornwall, NY 12518, 3 beds, 1 bath

$375,000

3 beds1 bath1,116 sq ft

11 Russell St, Cornwall, NY 12518

Listing by Smitchger Realty

Property at 99 Walnut St, Walden, NY 12586, 5 beds, 2.5 baths

$489,999

5 beds2.5 baths3,024 sq ft

99 Walnut St, Walden, NY 12586

Listing by Terrie OConnor

Property at 6 Erin Ct, Cornwall, NY 12518, 3 beds, 1 bath

$460,000

3 beds1 bath1,380 sq ft

6 Erin Ct, Cornwall, NY 12518

Listing by River Realty Services, Inc.

Property at 145 S Main St, Florida, NY 10921, 3 beds, 1 bath

$460,000

3 beds1 bath1,284 sq ft

145 S Main St, Florida, NY 10921

Listing by Keller Williams Realty

Property at 177 Grand St, Newburgh, NY 12550, 5 beds, 3 baths

$779,000

5 beds3 baths3,576 sq ft

177 Grand St, Newburgh, NY 12550

Listing by Houlihan Lawrence Inc.

Property at 52 Benkard Ave, Newburgh, NY 12550, 6 beds, 3 baths

$399,900

6 beds3 baths2,400 sq ft

52 Benkard Ave, Newburgh, NY 12550

Listing by Douglas Elliman Real Estate

Property at 685 South St, Newburgh, NY 12550, 3 beds, 2 baths

$330,000

3 beds2 baths1,700 sq ft

685 South St, Newburgh, NY 12550

Listing by Redfin Real Estate

Property at 6 Deer Trl N, Greenwood Lake, NY 10925, 1 bed, 1 bath

$385,000

1 bed1 bath726 sq ft

6 Deer Trl N, Greenwood Lake, NY 10925

Listing by RE/MAX Benchmark Realty Group

Property at 44 Cedar Ave, New Windsor, NY 12553, 4 beds, 2 baths

$400,000

4 beds2 baths1,680 sq ft

44 Cedar Ave, New Windsor, NY 12553

Listing by RE/MAX Town & Country

Property at 27 Interlochen Pkwy, Monroe, NY 10950, 3 beds, 1 bath

$376,000

3 beds1 bath702 sq ft

27 Interlochen Pkwy, Monroe, NY 10950

Listing by Flag Realty Group

Property at 65 Carson Ave, Newburgh, NY 12550, 3 beds, 3 baths

$425,000

3 beds3 baths1,500 sq ft

65 Carson Ave, Newburgh, NY 12550

Listing by Compass Greater NY, LLC

Property at 4 Catherine St, Port Jervis, NY 12771, 4 beds, 2 baths

$275,000

4 beds2 baths2,138 sq ft

4 Catherine St, Port Jervis, NY 12771

Listing by Mid Hudson Realty & Associates

Property at 75 Deer Trl N, Greenwood Lake, NY 10925, 2 beds, 1 bath

$135,000

2 beds1 bath556 sq ft

75 Deer Trl N, Greenwood Lake, NY 10925

Listing by Capri Jet Realty Corp

Property at 526 State Route 42, Sparrow Bush, NY 12780, 3 beds, 1 bath

$389,900

3 beds1 bath1,296 sq ft

526 State Route 42, Sparrow Bush, NY 12780

Listing by Keller Williams Hudson Valley

Property at 3 Birch St, Middletown, NY 10940, 2 beds, 1 bath

$85,000

2 beds1 bath600 sq ft

3 Birch St, Middletown, NY 10940

Listing by Capri Jet Realty Corp

Property at 252 Schunnemunk Rd, Monroe, NY 10950, 2 beds, 1.5 baths

$699,000

2 beds1.5 baths1,006 sq ft

252 Schunnemunk Rd, Monroe, NY 10950

Listing by eRealty Advisors, Inc

Property at 76 Benkard Ave, Newburgh, NY 12550, 4 beds, 2 baths

$349,900

4 beds2 baths2,000 sq ft

76 Benkard Ave, Newburgh, NY 12550

Listing by Douglas Elliman Real Estate

Property at 37-39 Main St, Chester, NY 10918, 4 beds, 4 baths

$1,498,888

4 beds4 baths7,308 sq ft

37-39 Main St, Chester, NY 10918

Listing by eXp Realty

Property at 83 William St, Newburgh, NY 12550, 7 beds, 3 baths

$375,000

7 beds3 baths2,838 sq ft

83 William St, Newburgh, NY 12550

Listing by ReAttached

Property at 81 William St, Newburgh, NY 12550, 5 beds, 3 baths

$375,000

5 beds3 baths2,838 sq ft

81 William St, Newburgh, NY 12550

Listing by ReAttached

Property at 66 Benkard Ave, Newburgh, NY 12550, 4 beds, 2 baths

$339,900

4 beds2 baths1,350 sq ft

66 Benkard Ave, Newburgh, NY 12550

Listing by Douglas Elliman Real Estate

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Based on information submitted to the MLS GRID as of Tue Dec 02 2025. 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.

Vintage Homes for Sale in Orange County

There are currently 439 vintage homes for sale in Orange County at a median listing price of $499K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Orange County stay on the market for 62 days and receive 3 offers. This map is refreshed with the newest listings in Orange County every 15 minutes.

In the past month, 267 homes have been sold in Orange County. In addition to houses in Orange County, there were also 128 condos, 3 townhouses, and 119 multi-family units for sale in Orange County last month. Find your dream home in Orange County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Orange County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Orange County. If you're looking to sell your home in the Orange County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Orange County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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