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:
Welcome Home! This City of Newburgh colonial home is a unique find, featuring a driveway and a one-car garage. Upon entering this lovely home, you will find a living room with a gas fireplace, a formal dining room with chair rail detail. The kitchen has white cabinets, double wall oven, stainless steel refrigerator and beautiful copper backsplash and copper hood vent. In the mud room, you will find a pantry with ceiling wood beam detail. Right off the mud room is the half bath with a washer and dryer and more wood beam detail. The second floor you will find 3 bedrooms and a full bath. The 3rd bedroom has steps that lead to a finished attic that could be used as a playroom, storage space or

$379,000

3 beds1.5 baths1,668 sq ft

310 Carpenter Ave, Newburgh, NY 12550

Double wall oven • Finished attic • Work room

Listing by HomeSmart Homes & Estates

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Discover a beautifully renovated 2-family home in the vibrant and growing City of Newburgh, offering both an excellent investment opportunity and a potential owner-occupant lifestyle. This property has been thoughtfully updated from top to bottom, blending modern conveniences with the character of its historic setting. The larger unit is a spacious duplex featuring 3 bedrooms and 1.5 baths, perfect for tenants seeking ample living space. The layout includes a bright and inviting living area, updated kitchen with new appliances, and tastefully renovated baths. Ceramic tile floors add both durability and style, making this unit low-maintenance and highly desirable. The second unit is a charmi

$319,913

4 beds3 baths1,008 sq ft

42 Hasbrouck St, Newburgh, NY 12550

Separate entrance • Updated bath • Spacious duplex

Listing by Your Move Matters LLC

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Discover a beautifully renovated 2-family home in the vibrant and growing City of Newburgh, offering both an excellent investment opportunity and a potential owner-occupant lifestyle. This property has been thoughtfully updated from top to bottom, blending modern conveniences with the character of its historic setting. The larger unit is a spacious duplex featuring 3 bedrooms and 1.5 baths, perfect for tenants seeking ample living space. The layout includes a bright and inviting living area, updated kitchen with new appliances, and tastefully renovated baths. Ceramic tile floors add both durability and style, making this unit low-maintenance and highly desirable. The second unit is a charmi

$329,923

4 beds3 baths1,188 sq ft

28 Hasbrouck St, Newburgh, NY 12550

Separate entrance • Updated bath • Spacious duplex

Listing by Your Move Matters LLC

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
A Truly Unique Opportunity – Live, Work, or Both! Welcome to a property that perfectly blends charm, function, and versatility. This special offering is not only a wonderful place to call home but also provides incredible potential to operate your own business—all in a convenient, easily accessible location. Currently configured as a single-family residence with mixed-use potential, this property gives you the flexibility to live on-site and run your business, or convert it entirely into a commercial space. The home offers 1,088 sq. ft. of living space and features one—or potentially two—bedrooms, a full bathroom, and a formal dining room. The warm, inviting family r

$399,900

1 bed1 bath1,088 sq ft

727 Route 17m, Middletown, NY 10940

Formal dining room • Vaulted ceiling • Large enclosed porch

Listing by Cronin & Company Real Estate

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Welcome to 16 Fay Avenue — a spacious and turnkey 4-bedroom, 2-full bath home that was completely renovated 2020. Major updates include a new roof (2020), new heating system (2020), new water heater (2020), new deck (2020) new kitchen (2020), and bathroom (2020) offering modern comfort and peace of mind for years to come. The home features a permitted finished basement with its own private entrance, perfect for an in-law suite, a guest space, or extended living arrangements. This flexible layout is ideal for multigenerational living, work-from-home options, or additional recreational space. Additional spacious bonus room off the Garage great for a game room and/or 5th bedroom. This ho

$510,000

4 beds2 baths2,319 sq ft

16 Faye Ave, New Windsor, NY 12553

New kitchen • New bathroom • New water heater

Listing by Century 21 Realty Center

Property at 441 Scotchtown Collabar Rd, Middletown, NY 10941, 4 beds, 3 baths

$1,100,000

4 beds3 baths2,787 sq ft

441 Scotchtown Collabar Rd, Middletown, NY 10941

Listing by Ellis Sotheby's Intl Realty

Property at 19 Lewis St, Otisville, NY 10963, 2 beds, 1 bath

$299,000

2 beds1 bath814 sq ft

19 Lewis St, Otisville, NY 10963

Listing by Keller Williams Hudson Valley

Property at 5 New St, Port Jervis, NY 12771, 5 beds, 2 baths

$249,000

5 beds2 baths2,396 sq ft

5 New St, Port Jervis, NY 12771

Listing by Keller Williams Hudson Valley

Property at 122 Route 17k, Newburgh, NY 12550, 4 beds, 2 baths

$650,000

4 beds2 baths2,000 sq ft

122 Route 17k, Newburgh, NY 12550

Listing by Christie's Int. Real Estate

Property at 8 Haight Rd, Monroe, NY 10950, 3 beds, 1 bath

$379,000

3 beds1 bath1,164 sq ft

8 Haight Rd, Monroe, NY 10950

Listing by Absolute Real Estate of NY Inc

Property at 40 Flemming Dr, Newburgh, NY 12550, 3 beds, 1.5 baths

$259,900

3 beds1.5 baths1,000 sq ft

40 Flemming Dr, Newburgh, NY 12550

Listing by RE/MAX Benchmark Realty Group

Property at 6 Center St, Port Jervis, NY 12771, 3 beds, 1 bath

$175,000

3 beds1 bath1,412 sq ft

6 Center St, Port Jervis, NY 12771

Listing by Keller Williams Hudson Valley

Property at 7 Brook Dr, Monroe, NY 10950, 3 beds, 1 bath

$399,000

3 beds1 bath864 sq ft

7 Brook Dr, Monroe, NY 10950

Listing by Sage Realty Center LLC

Property at 24 Washington Ave, Port Jervis, NY 12771, 4 beds, 2 baths

$199,000

4 beds2 baths1,886 sq ft

24 Washington Ave, Port Jervis, NY 12771

Listing by Keller Williams Hudson Valley

Property at 1513 State Route 17a, Warwick, NY 10990, 2 beds, 2 baths

$550,000

2 beds2 baths1,859 sq ft

1513 State Route 17a, Warwick, NY 10990

Listing by RE/MAX Benchmark Realty Group

Property at 212 Cheechunk Rd, Goshen, NY 10924, 7 beds, 4.5 baths

$1,750,000

7 beds4.5 baths3,000 sq ft

212 Cheechunk Rd, Goshen, NY 10924

Listing by RE/MAX Benchmark Realty Group

Property at 144 Dubois St, Newburgh, NY 12550, 3 beds, 2 baths

$357,000

3 beds2 baths1,869 sq ft

144 Dubois St, Newburgh, NY 12550

Listing by eXp Realty

Property at 4 Plains Rd, Walden, NY 12586, 3 beds, 1.5 baths

$549,900

3 beds1.5 baths2,048 sq ft

4 Plains Rd, Walden, NY 12586

Listing by 1st Independent Realty Grp

Property at 96 Bellvale Lakes Rd, Warwick, NY 10990, 5 beds, 6 baths

$1,999,999

5 beds6 baths6,414 sq ft

96 Bellvale Lakes Rd, Warwick, NY 10990

Listing by R2M Realty Inc

Property at 46 Quaker Hill Rd, Monroe, NY 10950, 3 beds, 2 baths

$499,000

3 beds2 baths1,400 sq ft

46 Quaker Hill Rd, Monroe, NY 10950

Listing by eXp Realty

Property at 1 Pinecrest, Warwick, NY 10990, 3 beds, 2 baths

$469,900

3 beds2 baths1,288 sq ft

1 Pinecrest, Warwick, NY 10990

Listing by Exit Realty Connections

Property at 89 Liberty St, Newburgh, NY 12550, 1 bed

$599,000

1 bed— baths4,800 sq ft

89 Liberty St, Newburgh, NY 12550

Listing by Richmont Realty

Property at 46 Neversink Dr, Port Jervis, NY 12771, 2 beds, 1.5 baths

$399,999

2 beds1.5 baths1,037 sq ft

46 Neversink Dr, Port Jervis, NY 12771

Listing by eXp Realty

Property at 60 Union St, Montgomery, NY 12549, 3 beds, 2.5 baths

$465,000

3 beds2.5 baths1,980 sq ft

60 Union St, Montgomery, NY 12549

Listing by Redfin Real Estate

Property at 180 Shoddy Hollow Rd, Otisville, NY 10963, 3 beds, 2 baths

$449,000

3 beds2 baths1,824 sq ft

180 Shoddy Hollow Rd, Otisville, NY 10963

Listing by Howard Hanna Rand Realty

Property at 70 Main St, Chester, NY 10918, 4 beds, 2.5 baths

$475,000

4 beds2.5 baths1,357 sq ft

70 Main St, Chester, NY 10918

Listing by Keller Williams Hudson Valley

Property at 19 Oakland Valley Rd, Cuddebackville, NY 12729, 5 beds, 1.5 baths

$289,900

5 beds1.5 baths3,312 sq ft

19 Oakland Valley Rd, Cuddebackville, NY 12729

Listing by eXp Realty

Property at 20 Prospect Ave, Goshen, NY 10924, 4 beds, 3 baths

$539,000

4 beds3 baths2,732 sq ft

20 Prospect Ave, Goshen, NY 10924

Listing by Ethos Realty LLC

Property at 5 Berkley Ter, Monroe, NY 10950, 4 beds, 2 baths

$530,000

4 beds2 baths1,322 sq ft

5 Berkley Ter, Monroe, NY 10950

Listing by Century 21 Realty Center

Property at 10 Oakwood Ter #65, New Windsor, NY 12553, 1 bed, 1 bath

$139,000

1 bed1 bath750 sq ft

10 Oakwood Ter #65, New Windsor, NY 12553

Listing by Keller Williams Realty

Property at 8 Hill Rd, Goshen, NY 10924, 3 beds, 1 bath

$350,000

3 beds1 bath924 sq ft

8 Hill Rd, Goshen, NY 10924

Listing by Keller Williams Hudson Valley

Property at 120 Jersey Ave, Port Jervis, NY 12771, 4 beds, 2.5 baths

$450,000

4 beds2.5 baths3,294 sq ft

120 Jersey Ave, Port Jervis, NY 12771

Listing by Modern Realty and Management

Property at 43 Prospect Hill Rd, Cuddebackville, NY 12729, 4 beds, 1 bath

$379,000

4 beds1 bath2,148 sq ft

43 Prospect Hill Rd, Cuddebackville, NY 12729

Listing by Keller Williams Hudson Valley

Property at 20 Oakwood Trl N, Monroe, NY 10950, 2 beds, 1 bath

$200,000

2 beds1 bath550 sq ft

20 Oakwood Trl N, Monroe, NY 10950

Listing by Coldwell Banker Realty

Property at 106 Maple Ave, Monroe, NY 10950, 3 beds, 2 baths

$599,999

3 beds2 baths1,755 sq ft

106 Maple Ave, Monroe, NY 10950

Listing by Terrie OConnor

Property at 1 Second St, Walden, NY 12586, 3 beds, 1.5 baths

$384,999

3 beds1.5 baths1,188 sq ft

1 Second St, Walden, NY 12586

Listing by Keller Williams Realty

Property at 11 Merriewold Ln N, Monroe, NY 10950, 5 beds, 2 baths

$869,000

5 beds2 baths1,900 sq ft

11 Merriewold Ln N, Monroe, NY 10950

Listing by eRealty Advisors, Inc

Property at 22 City Ter, Newburgh, NY 12550, 6 beds, 4 baths

$80,000

6 beds4 baths1,891 sq ft

22 City Ter, Newburgh, NY 12550

Listing by Keller Williams Realty

Property at 12 Kiernan Gln, Cuddebackville, NY 12729, 2 beds, 1 bath

$675,000

2 beds1 bath1,088 sq ft

12 Kiernan Gln, Cuddebackville, NY 12729

Listing by Skipping Stones Realty

Property at 10 Prospect St, Unionville, NY 10988, 3 beds, 1 bath

$235,000

3 beds1 bath1,876 sq ft

10 Prospect St, Unionville, NY 10988

Listing by Howard Hanna Rand Realty

Property at 189 E Main St, Port Jervis, NY 12771, 3 beds, 1 bath

$170,000

3 beds1 bath1,407 sq ft

189 E Main St, Port Jervis, NY 12771

Listing by EXP Realty

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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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