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

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LISTED BY REDFIN

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Welcome to 12 Circle Drive, Tuxedo, NY 10987, a rare opportunity to customize a classic 3-bedroom, 2-bath Colonial set on a peaceful, partially wooded lot in one of the Hudson Valley’s most historic and picturesque communities. This 1200 sq ft property has been gutted down to the studs offering a clean and solid foundation for your vision with no hidden surprises behind the walls. A major bonus is the dry full-height concrete basement, providing excellent additional space for storage, utilities, or future finishing. All the groundwork has already been completed for you—a full set of architect-designed building plans is included for an addition to bring the property to 1700sq ft,

$349,000

3 beds2 baths1,200 sq ft

12 Circle Dr, Tuxedo Park, NY 10987

1,040 sq ft lot • Built 1890 • Listed 21 days

Listing by Redfin Real Estate

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Thoughtfully renovated and designed for comfortable, everyday living, this home offers modern updates and a spacious backyard in a highly convenient location. Just minutes from I-84, Route 9W and Newburgh Beacon Bridge, Mount Saint Mary College, you’ll enjoy quick access to the cities popular restaurants, the Hudson River waterfront, local shopping, and public transportation. Only 60 miles from NYC, it’s an excellent choice for commuters or those seeking a relaxed weekend retreat. Inside, hardwood floors, recessed lighting, and a fully updated kitchen with granite countertops create a warm and welcoming atmosphere. A newly renovated upstairs bathroom adds to the home’s fun

$399,000

3 beds1.5 baths1,299 sq ft

171 West St, Newburgh, NY 12550

Spacious backyard • Modern updates • Full basement

Listing by HomeSmart Homes & Estates

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Welcome home! This charming 3-bedroom, 1-bath property offers solid updates and so much room to make it your own. Recent improvements—including a new roof, new furnace, and new well pump—give you a great head start. The spacious yard is perfect for outdoor enjoyment, and the detached garage with a workshop area is ideal for projects, storage, or hobbies. Located close to schools and shopping with easy commuter access, this home offers comfort, convenience, and a wonderful opportunity for your next chapter.

$365,000

3 beds1 bath1,418 sq ft

647 S Drury Ln, Montgomery, NY 12549

Spacious yard • New furnace • New well pump

Listing by Keller Williams Hudson Valley

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Attention Investors, Developers, and Savvy buyers! This Rare Triplex Opportunity offers the perfect blend of location, potential, and value—where the most challenging, costly, and time-consuming phases of renovation are already COMPLETE. This triplex has been completely gutted to the studs—no demo work needed giving the new owner a headstart. It boasts a substantial list of new, foundational, and high-cost upgrades: New windows have been installed, Brick pointing, Structural Framing Improvements, Roof Repairs Completed, Balconies and Staircase Repairs and New Rear Porch Addition. Located just 4 minutes from major highway, 2 minutes from St. Lukes Hospital and 12 minutes from the

$315,000

5 beds3 baths2,240 sq ft

157 Johnston St, Newburgh, NY 12550

2,400 sq ft lot • Built 1900 • Listed 7 days

Listing by Keller Williams Hudson Valley

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Discover this cozy Cape Cod nestled in a quiet, well-kept neighborhood in the Town of Newburgh. This inviting home features a bright and functional kitchen with granite countertops and stainless steel appliances, perfect for everyday cooking or hosting. Warm wood floors flow throughout, adding charm and comfort to the space. Enjoy the convenience of being just minutes from schools, shopping, restaurants, and major highways, making commuting and daily errands a breeze. Whether you’re a first-time buyer or looking to downsize, this home offers the ideal blend of comfort, location, and value. Welcome to easy living at 17 Brookside Ave.

$449,990

3 beds2 baths1,460 sq ft

17 Brookside Ave, Newburgh, NY 12550

Bright kitchen • Wood floors • Granite countertops

Listing by HomeSmart Homes & Estates

Property at 36 Wintergreen Ave, Newburgh, NY 12550, 3 beds, 1.5 baths

$385,000

3 beds1.5 baths1,080 sq ft

36 Wintergreen Ave, Newburgh, NY 12550

Listing by RE/MAX Benchmark Realty Group

Property at 27-29 W Conkling Ave, Middletown, NY 10940, 3 beds, 1.5 baths

$409,999

3 beds1.5 baths1,560 sq ft

27-29 W Conkling Ave, Middletown, NY 10940

Listing by Keller Williams Realty

Property at 28 Spring St, Middletown, NY 10940, 4 beds, 2 baths

$329,000

4 beds2 baths1,696 sq ft

28 Spring St, Middletown, NY 10940

Listing by Howard Hanna Rand Realty

Property at 72 Jersey Ave, Unionville, NY 10988, 2 beds, 2.5 baths

$399,000

2 beds2.5 baths1,206 sq ft

72 Jersey Ave, Unionville, NY 10988

Listing by Keller Williams Realty

Property at 10 Wheeler Ave, Warwick, NY 10990, 4 beds, 1.5 baths

$475,000

4 beds1.5 baths2,001 sq ft

10 Wheeler Ave, Warwick, NY 10990

Listing by eRealty Advisors, Inc

Property at 443 Rye Hill Rd, Monroe, NY 10950, 5 beds, 2.5 baths

$499,000

5 beds2.5 baths2,456 sq ft

443 Rye Hill Rd, Monroe, NY 10950

Listing by MK Realty Inc

Property at 18 Oakland Ave, Chester, NY 10918, 2 beds, 1 bath

$369,900

2 beds1 bath1,084 sq ft

18 Oakland Ave, Chester, NY 10918

Listing by Keller Williams Realty

Property at 5 Stoll St, Port Jervis, NY 12771, 4 beds, 2 baths

$299,000

4 beds2 baths2,354 sq ft

5 Stoll St, Port Jervis, NY 12771

Listing by Avion

Property at 2768 State Route 207, Campbell Hall, NY 10916, 4 beds, 1.5 baths

$465,000

4 beds1.5 baths2,460 sq ft

2768 State Route 207, Campbell Hall, NY 10916

Listing by BHHS Hudson Valley Properties

Property at 135 N Orange, Port Jervis, NY 12771, 3 beds, 3 baths

$399,000

3 beds3 baths1,936 sq ft

135 N Orange, Port Jervis, NY 12771

Listing by Homes By Yara Realty Group LLC

Property at 33 Clark St, Newburgh, NY 12550, 4 beds, 1 bath

$150,000

4 beds1 bath1,120 sq ft

33 Clark St, Newburgh, NY 12550

Listing by Epique Realty

Property at 190 W Main St, Port Jervis, NY 12771, 3 beds, 2 baths

$244,000

3 beds2 baths2,025 sq ft

190 W Main St, Port Jervis, NY 12771

Listing by Krumpfer Realty Group, LLC

Property at 154 3rd St, Newburgh, NY 12550, 8 beds, 4 baths

$675,000

8 beds4 baths2,955 sq ft

154 3rd St, Newburgh, NY 12550

Listing by Keller Williams Hudson Valley

Property at 105 Carson Ave, Newburgh, NY 12550, 3 beds, 1.5 baths

$250,000

3 beds1.5 baths1,535 sq ft

105 Carson Ave, Newburgh, NY 12550

Listing by eXp Realty

Property at 252 Round Hill Rd, Florida, NY 10921, 3 beds, 2 baths

$599,000

3 beds2 baths2,180 sq ft

252 Round Hill Rd, Florida, NY 10921

Listing by HomeSmart Homes & Estates

Property at 25 Pine St, Port Jervis, NY 12771, 3 beds, 2 baths

$314,999

3 beds2 baths1,629 sq ft

25 Pine St, Port Jervis, NY 12771

Listing by Century 21 Geba Realty

Property at 78 Commonwealth Ave, Middletown, NY 10940, 3 beds, 2.5 baths

$558,000

3 beds2.5 baths2,108 sq ft

78 Commonwealth Ave, Middletown, NY 10940

Listing by Keller Williams Hudson Valley

Property at 1433 Route 208, Washingtonville, NY 10992, 6 beds, 3.5 baths

$849,000

6 beds3.5 baths3,684 sq ft

1433 Route 208, Washingtonville, NY 10992

Listing by Priority Management

Property at 36 Bert Crawford Rd, Middletown, NY 10940, 2 beds, 1 bath

$319,900

2 beds1 bath836 sq ft

36 Bert Crawford Rd, Middletown, NY 10940

Listing by Keller Williams Realty

Property at 25 Teneyck Ave, Greenwood Lake, NY 10925, 5 beds, 3 baths

$799,999

5 beds3 baths— sq ft

25 Teneyck Ave, Greenwood Lake, NY 10925

Listing by Keller Williams Rlty Integrity

Property at 179 Reservoir Rd, Middletown, NY 10940, 3 beds, 2 baths

$620,000

3 beds2 baths3,080 sq ft

179 Reservoir Rd, Middletown, NY 10940

Listing by Keller Williams Hudson Valley

Property at 22 Sylvan Trl, Monroe, NY 10950, 3 beds, 1 bath

$259,900

3 beds1 bath784 sq ft

22 Sylvan Trl, Monroe, NY 10950

Listing by P R O Links Realty Inc

Property at 55 Old Little Britain Rd, Newburgh, NY 12550, 3 beds, 1 bath

$349,900

3 beds1 bath1,470 sq ft

55 Old Little Britain Rd, Newburgh, NY 12550

Listing by Frank Tangredi Realty Company

Property at 44 Linden Ave, Greenwood Lake, NY 10925, 3 beds, 3 baths

$747,000

3 beds3 baths1,792 sq ft

44 Linden Ave, Greenwood Lake, NY 10925

Listing by Keller Williams Realty

Property at 86 Gardnertown Rd, Newburgh, NY 12550, 3 beds, 1 bath

$399,000

3 beds1 bath1,582 sq ft

86 Gardnertown Rd, Newburgh, NY 12550

Listing by Keller Williams Realty Partner

Property at 114 Dupont Ave, Newburgh, NY 12550, 2 beds, 1 bath

$275,000

2 beds1 bath1,122 sq ft

114 Dupont Ave, Newburgh, NY 12550

Listing by RE/MAX Benchmark Realty Group

Property at 24 Woodlands Ter, Greenwood Lake, NY 10925, 3 beds, 2 baths

$559,000

3 beds2 baths1,305 sq ft

24 Woodlands Ter, Greenwood Lake, NY 10925

Listing by Howard Hanna Rand Realty

Property at 24 Patricia Ln, Washingtonville, NY 10992, 3 beds, 2 baths

$450,000

3 beds2 baths1,334 sq ft

24 Patricia Ln, Washingtonville, NY 10992

Listing by Keller Williams Realty

Property at 10 Rumsey St, Port Jervis, NY 12771, 3 beds, 1 bath

$200,000

3 beds1 bath1,396 sq ft

10 Rumsey St, Port Jervis, NY 12771

Listing by Orange West Realty

Property at 111 Sycamore Dr, New Windsor, NY 12553, 4 beds, 4.5 baths

$575,000

4 beds4.5 baths3,589 sq ft

111 Sycamore Dr, New Windsor, NY 12553

Listing by eXp Realty

Property at 651 Lakes Rd, Monroe, NY 10950, 4 beds, 2 baths

$874,900

4 beds2 baths2,466 sq ft

651 Lakes Rd, Monroe, NY 10950

Listing by Howard Hanna Rand Realty

Property at 39 Susan Dr, Newburgh, NY 12550, 2 beds, 1.5 baths

$839,000

2 beds1.5 baths1,304 sq ft

39 Susan Dr, Newburgh, NY 12550

Listing by BHHS Hudson Valley Properties

Property at 807 Abbey Ave, Maybrook, NY 12543, 4 beds, 2 baths

$374,900

4 beds2 baths1,750 sq ft

807 Abbey Ave, Maybrook, NY 12543

Listing by Curasi Realty, Inc.

Property at 128 William St, Newburgh, NY 12550, 5 beds, 2 baths

$300,000

5 beds2 baths1,950 sq ft

128 William St, Newburgh, NY 12550

Listing by RE/MAX Benchmark Realty Group

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

$279,900

3 beds1 bath844 sq ft

17 Fourth Rd, Greenwood Lake, NY 10925

Listing by Howard Hanna Rand Realty

Property at 168 Fostertown Rd, Newburgh, NY 12550, 6 beds, 3 baths

$649,999

6 beds3 baths3,120 sq ft

168 Fostertown Rd, Newburgh, NY 12550

Listing by HomeSmart Homes & Estates

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Based on information submitted to the MLS GRID as of Mon Dec 01 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 441 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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