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

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ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
This tastefully renovated Cape offers modern updates with timeless character in a convenient neighborhood and ready for its next owner(s). Modern updates to the kitchen in April 2020, include stylish cabinets, granite countertops, tiled floor, subway backsplash, and stainless-steel appliances. The main level showcases hardwood floors throughout the living room, dining room, bedroom, an updated powder room and a quaint screened in porch where you can enjoy nature and your favorite beverage. Upstairs, you’ll find two spacious bedrooms, hardwood floors, both with walk in closets, along with a beautifully updated full bathroom (2021). Additional updates include a new water heater (2021),

$385,000

3 beds1.5 baths1,080 sq ft

36 Wintergreen Ave, Newburgh, NY 12550

0.52 acre lot • Garage • Built 1940

Listing by RE/MAX Benchmark Realty Group

NEW 54 MINS AGO

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
ONE FLOOR LIVING! Perfect starter home or for retirement. Welcome to Maybrook! This home has hardwood flooring throughout, a laundry area on the first floor and a shed for extra storage. It is close to major highways, shops, restaurants and the train. Come take a look-it might be just what you are looking for.

$199,900

2 beds1 bath768 sq ft

304 Clark Pl, Maybrook, NY 12543

Hardwood flooring • Close to restaurants • Laundry area

Listing by Curasi Realty, Inc.

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Discover a rare mid-century contemporary set on just under an acre in Middletown. With more than 3,500 square feet, this 5 bedroom, 2 bath home offers incredible space, soaring ceilings, and floor-to-ceiling windows that fill every corner with natural light. The open, airy layout highlights the home’s architectural character, creating the perfect canvas for a modern makeover. The full basement adds even more potential for living space, storage, or a creative studio. Sitting on a . 98-acre lot, the property provides privacy while still keeping you close to local shops, dining, and conveniences. This unique home needs work but the bones, scale, and style are all here. Bring your vision

$350,000

5 beds2.5 baths3,581 sq ft

57 Overhill Rd, Middletown, NY 10940

0.98 acre lot • 2 garage spots • Built 1955

Listing by eXp Realty

NEW 12 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
A cozy porch, a quaint yard, and room to grow! Welcome to this adorable two-bedroom ranch home in the heart of Otisville—packed with character and waiting for someone to bring their vision to life. The enclosed front porch invites you in with its cozy appeal, offering the perfect spot to enjoy a morning coffee! Inside, the home offers a traditional layout and great bones, ready for renovation and updating to suit your style. A standout feature is the full walk-up attic, currently unfinished, offering exceptional potential for future living space or generous storage. Outside, the property includes a quaint, manageable, fenced-in yard—ideal for gardening, relaxing, or creating you

$229,900

2 beds1 bath1,224 sq ft

18 Seybolt Ave, Otisville, NY 10963

Quaint yard • Full walk-up attic • Cozy porch

Listing by RE/MAX Benchmark Realty Group

NEW 15 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Elegant Colonial Retreat comes fully Renovated and Move in Ready! Welcome home to this beautifully renovated Colonial style gem featuring 4 spacious bedroom and 2.5 baths offering a nice blend of Charm, Comfort and modern luxury. This home offers a sunlit eat in kitchen with beautiful countertops, stainless steel appliances, and seamless flow to enclosed sun porch overlooking a large backyard complete with an inground fenced in pool, so ideal for entertaining and quiet relaxation. Enjoy a nice private primary suite, along with three additional bedrooms, including one with a large walk in storage closet. The walkable attic provides plenty of extra storage for seasonal items or future expans

$619,000

4 beds2.5 baths2,540 sq ft

10 Glen Ln, Newburgh, NY 12550

Fully renovated • Large backyard • Enclosed sun porch

Listing by Weichert Realtors Heritage Pro

Property at 5091 Route 9W, Newburgh, NY 12550, 4 beds, 2.5 baths

$748,000

4 beds2.5 baths3,933 sq ft

5091 Route 9W, Newburgh, NY 12550

Listing by Weichert Realtors

Property at 171 Chambers St, Newburgh, NY 12550, 5 beds, 4 baths

$574,000

5 beds4 baths2,800 sq ft

171 Chambers St, Newburgh, NY 12550

Listing by RE/MAX Town & Country

Property at 48 Main St, Sparrow Bush, NY 12780, 3 beds, 2 baths

$375,000

3 beds2 baths2,000 sq ft

48 Main St, Sparrow Bush, NY 12780

Listing by Orange West Realty

Property at 256 Round Hill Rd, Florida, NY 10921, 5 beds, 1 bath

$550,000

5 beds1 bath1,925 sq ft

256 Round Hill Rd, Florida, NY 10921

Listing by Keller Williams Realty

Property at 35 Carpenter Ave, Newburgh, NY 12550, 2 beds, 2.5 baths

$240,000

2 beds2.5 baths1,852 sq ft

35 Carpenter Ave, Newburgh, NY 12550

Listing by River Realty Services, Inc.

Property at 193 Schutt Rd, Middletown, NY 10940, 3 beds, 1 bath

$249,900

3 beds1 bath900 sq ft

193 Schutt Rd, Middletown, NY 10940

Listing by HomeSmart Homes & Estates

Property at 17 Perry Rd, Cornwall, NY 12518, 3 beds, 2 baths

$460,000

3 beds2 baths1,418 sq ft

17 Perry Rd, Cornwall, NY 12518

Listing by Compass Greater NY, LLC

Property at 8 Forest Ln, Greenwood Lake, NY 10925, 2 beds, 1 bath

$350,000

2 beds1 bath738 sq ft

8 Forest Ln, Greenwood Lake, NY 10925

Listing by eRealty Advisors, Inc

Property at 143 Plains Rd, Walden, NY 12586, 3 beds, 1.5 baths

$409,000

3 beds1.5 baths1,092 sq ft

143 Plains Rd, Walden, NY 12586

Listing by Curasi Realty, Inc.

Property at 14 Kingston Ave, Port Jervis, NY 12771, 3 beds, 1 bath

$259,000

3 beds1 bath1,632 sq ft

14 Kingston Ave, Port Jervis, NY 12771

Listing by RE/MAX Benchmark Realty Group

Property at 128 W Main St, Middletown, NY 10940, 8 beds, 6 baths

$625,000

8 beds6 baths3,240 sq ft

128 W Main St, Middletown, NY 10940

Listing by Keller Williams Hudson Valley

Property at 15 Clark St, Newburgh, NY 12550, 5 beds, 3 baths

$549,000

5 beds3 baths1,688 sq ft

15 Clark St, Newburgh, NY 12550

Listing by Mimi Realty USA, Inc

Property at 11 Oakland Ct, Warwick, NY 10990, 4 beds, 1.5 baths

$699,000

4 beds1.5 baths2,040 sq ft

11 Oakland Ct, Warwick, NY 10990

Listing by Joseph Baratta Company Realty

Property at 9 Deer Trl S, Greenwood Lake, NY 10925, 1 bed, 1 bath

$229,000

1 bed1 bath720 sq ft

9 Deer Trl S, Greenwood Lake, NY 10925

Listing by Howard Hanna Rand Realty

Property at 25 E Broome St, Port Jervis, NY 12771, 4 beds, 1 bath

$215,000

4 beds1 bath2,272 sq ft

25 E Broome St, Port Jervis, NY 12771

Listing by Prominent Properties Sotheby's

Property at 49 Main St, Sparrow Bush, NY 12780, 3 beds, 1 bath

$249,900

3 beds1 bath1,584 sq ft

49 Main St, Sparrow Bush, NY 12780

Listing by eXp Realty

Property at 51 Wileman Ave, Walden, NY 12586, 4 beds, 2 baths

$250,000

4 beds2 baths2,016 sq ft

51 Wileman Ave, Walden, NY 12586

Listing by Ethos Realty LLC

Property at 440 Mt Orange Rd, Middletown, NY 10940, 1 bed, 1 bath

$131,250

1 bed1 bath654 sq ft

440 Mt Orange Rd, Middletown, NY 10940

Listing by Prime Partner Realty

Property at 13 S Miller St, Newburgh, NY 12550, 3 beds, 2 baths

$269,999

3 beds2 baths1,708 sq ft

13 S Miller St, Newburgh, NY 12550

Listing by Hudson Valley Home Connection

Property at 37 Pressler Rd, Wallkill, NY 12589, 3 beds, 3 baths

$425,000

3 beds3 baths2,454 sq ft

37 Pressler Rd, Wallkill, NY 12589

Listing by Tactical Realty LLC

Property at 10 Royce Ave, Middletown, NY 10940, 3 beds, 1.5 baths

$330,000

3 beds1.5 baths1,470 sq ft

10 Royce Ave, Middletown, NY 10940

Listing by eXp Realty

Property at 460 County Highway 1, Warwick, NY 10990, 1 bed, 2 baths

$399,900

1 bed2 baths1,200 sq ft

460 County Highway 1, Warwick, NY 10990

Listing by eXp Realty

Property at 164 Van Keuren Ave, Pine Bush, NY 12566, 4 beds, 2 baths

$360,000

4 beds2 baths1,996 sq ft

164 Van Keuren Ave, Pine Bush, NY 12566

Listing by Divine Realty NY, LLC

Property at 11 Sunset Dr, New Windsor, NY 12553, 3 beds, 2 baths

$424,900

3 beds2 baths1,595 sq ft

11 Sunset Dr, New Windsor, NY 12553

Listing by Sams Realty

Property at 71 Commonwealth Ave, Middletown, NY 10940, 3 beds, 1 bath

$360,000

3 beds1 bath1,344 sq ft

71 Commonwealth Ave, Middletown, NY 10940

Listing by Keller Williams Hudson Valley

Property at 44 Lake Shore Rd, Greenwood Lake, NY 10925, 2 beds, 1 bath

$550,000

2 beds1 bath986 sq ft

44 Lake Shore Rd, Greenwood Lake, NY 10925

Listing by Compass Greater NY, LLC

Property at 6 Willow St, Newburgh, NY 12550, 3 beds, 1.5 baths

$350,000

3 beds1.5 baths1,428 sq ft

6 Willow St, Newburgh, NY 12550

Listing by RE/MAX Town & Country

Property at 3 Garden Dr, New Windsor, NY 12553, 3 beds, 2 baths

$495,000

3 beds2 baths1,790 sq ft

3 Garden Dr, New Windsor, NY 12553

Listing by Howard Hanna Rand Realty

Property at 65 Monhagen Ave, Middletown, NY 10940, 3 beds, 2.5 baths

$350,000

3 beds2.5 baths930 sq ft

65 Monhagen Ave, Middletown, NY 10940

Listing by Keller Williams Hudson Valley

Property at 180 Union Ave, New Windsor, NY 12553, 3 beds, 1 bath

$429,999

3 beds1 bath1,200 sq ft

180 Union Ave, New Windsor, NY 12553

Listing by Magic Of Great Neck Realty Inc

Property at 56 Indian Trl, Greenwood Lake, NY 10925, 2 beds, 1 bath

$349,999

2 beds1 bath777 sq ft

56 Indian Trl, Greenwood Lake, NY 10925

Listing by Coldwell Banker M&D Good Life

Property at 68 Henry Ave, Newburgh, NY 12550, 5 beds, 2 baths

$265,000

5 beds2 baths2,280 sq ft

68 Henry Ave, Newburgh, NY 12550

Listing by Keller Williams Hudson Valley

Property at 747 Oakland Valley Rd, Cuddebackville, NY 12729, 4 beds, 2 baths

$299,000

4 beds2 baths1,352 sq ft

747 Oakland Valley Rd, Cuddebackville, NY 12729

Listing by Keller Williams Hudson Valley

Property at 89 Maple Brook Rd, Tuxedo Park, NY 10987, 3 beds, 2 baths

$570,000

3 beds2 baths1,441 sq ft

89 Maple Brook Rd, Tuxedo Park, NY 10987

Listing by Howard Hanna Rand Realty

Property at 77 Jessup Switch Rd, Florida, NY 10921, 6 beds, 2 baths

$325,000

6 beds2 baths2,371 sq ft

77 Jessup Switch Rd, Florida, NY 10921

Listing by MS Realty Group USA, Inc

Property at 17 Pine Hill Rd, Highland Mills, NY 10930, 2 beds, 1 bath

$625,000

2 beds1 bath1,224 sq ft

17 Pine Hill Rd, Highland Mills, NY 10930

Listing by Preferred Properties Real Esta

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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 438 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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