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:
Renamor is a spectacular estate blending history, grandeur and modern sustainability in a truly unique way. It is situated on the largest piece of property ever to be sold in historic Tuxedo Park, 151 acres! The fact that it’s now on the market for the first time in over 30 years makes it even more enticing for a discerning buyer seeking a one-of-a-kind property. Built circa 1928 in the romantic French Provincial style, Renamor stands apart from other Gilded Age homes in the region for its timeless charm and rustic elegance popularized in post-World War I America architecture. With its distinct hip roof, classic clay tiles, dormer windows, stone and stucco facade and period ironwork i

$29,500,000

19 beds21 baths22,400 sq ft

120 Ridge Rd, Tuxedo Park, NY 10987

Historic tuxedo park • Spa pool house • Lake access

Listing by Ellis Sotheby's Intl Realty

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Welcome to 19 Oakland Valley Road in Cuddebackville, a Hudson Valley property brimming with potential. This fixer-upper is the perfect opportunity for buyers looking to create their dream home, investment property, or weekend retreat. Set on a spacious lot, it offers plenty of room for outdoor living, gardening, and recreation. Inside, you’ll find a generous layout with 5 bedrooms 1 bathroom, a living area filled with natural light, and a kitchen ready for your personal touch. With vision and updates, this home can be transformed into a modern, stylish residence while maintaining its country charm. Outdoors, the expansive yard provides endless possibilities—whether for entertain

$289,900

5 beds1.5 baths3,312 sq ft

19 Oakland Valley Rd, Cuddebackville, NY 12729

Close to schools • Expansive yard • Spacious lot

Listing by eXp Realty

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
This stunning, fully renovated home blends modern luxury with lakeside tranquility. Inside, discover a designer gourmet kitchen featuring quartz countertops, custom walnut shelving, white shaker cabinets, a SMEG retro refrigerator, sleek new backsplash, stainless steel appliances including a Bosch dishwasher and a convection oven with air fryer and a stylish new oven hood. The open concept layout seamlessly connects the kitchen, dining, and living areas, creating a space ideal for both daily living and entertaining. The first floor offers two spacious bedrooms, a modern tiled bathroom, and a laundry area equipped with a GE Profile washer and dryer. The primary suite features generous closet

$600,000

2 beds2 baths1,935 sq ft

2 Erica Ln, Greenwood Lake, NY 10925

0.27 acre lot • Garage • Built 1940

Listing by Howard Hanna Rand Realty

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
2 Family completely renovated with basement and first floor making up a 2 bedroom 2 bath unit and the second and third floors laid out as a 5 bedroom 2 bath unit with access to the back yard. Close to restaurants, cafes, Colleges, Hospitals, Newburgh-Beacon Ferry, parks. A great investor opportunity.

$344,000

7 beds4 baths2,112 sq ft

82 Lander St, Newburgh, NY 12550

Completely renovated • Investor opportunity • 2,500 sq ft lot

Listing by Renaissance Realty Cons Group

ABOUT THIS HOME
Vintage Home for sale in Orange County, NY:
Greenwood Lake!! Wonderful opportunity to own a spacious house in this picturesque lake village located about an hour from NYC! Great potential! 3 bedrooms, 2. 5 bathrooms, large kitchen area with a slider to a private patio. Large living room with fireplace and a den. This house is located in Indian Park Community where residents can enjoy a private beach, the lake and a clubhouse. Bus to NYC at the park entrance. Sold as is where is, however seller will install new septic tank.

$442,000

3 beds2.5 baths2,022 sq ft

62 Deer Trl S, Greenwood Lake, NY 10925

Large kitchen area • Private beach • Private patio

Listing by HomeSmart Homes & Estates

Property at 132 Ridge Rd, Highland Mills, NY 10930, 3 beds, 1.5 baths

$465,000

3 beds1.5 baths1,751 sq ft

132 Ridge Rd, Highland Mills, NY 10930

Listing by MS Realty Group USA, Inc

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 168 Grand St, Newburgh, NY 12550, 9 beds, 4 baths

$999,000

9 beds4 baths5,406 sq ft

168 Grand St, Newburgh, NY 12550

Listing by Hanson Real Estate Partners

Property at 17 Schneider Ave, Highland Falls, NY 10928, 3 beds, 1 bath

$336,000

3 beds1 bath1,163 sq ft

17 Schneider Ave, Highland Falls, NY 10928

Listing by eRealty Advisors, Inc

Property at 84 Pine Hill Rd, Chester, NY 10918, 3 beds, 1 bath

$425,000

3 beds1 bath1,266 sq ft

84 Pine Hill Rd, Chester, NY 10918

Listing by eRealty Advisors, Inc

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 137 North St, Newburgh, NY 12550, 3 beds, 1.5 baths

$295,000

3 beds1.5 baths1,120 sq ft

137 North St, Newburgh, NY 12550

Listing by K Fortuna Lighthouse Realty

Property at 1-3 Amdurer Rd, Westtown, NY 10998, 1 bed, 1 bath

$325,000

1 bed1 bath864 sq ft

1-3 Amdurer Rd, Westtown, NY 10998

Listing by HomeSmart Homes & Estates

Property at 64 Homestead Ln, Otisville, NY 10963, 3 beds, 2 baths

$499,880

3 beds2 baths2,576 sq ft

64 Homestead Ln, Otisville, NY 10963

Listing by Keller Williams Hudson Valley

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 98 Overlook Pl, Newburgh, NY 12550, 8 beds, 3 baths

$370,000

8 beds3 baths2,724 sq ft

98 Overlook Pl, Newburgh, NY 12550

Listing by Renaissance Realty Cons Group

Property at 57 S Lander St, Newburgh, NY 12550, 4 beds, 2 baths

$349,000

4 beds2 baths— sq ft

57 S Lander St, Newburgh, NY 12550

Listing by Exit Realty Connections

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 55 Peenpack Trl, Huguenot, NY 12746, 2 beds, 1.5 baths

$289,900

2 beds1.5 baths1,210 sq ft

55 Peenpack Trl, Huguenot, NY 12746

Listing by HomeSmart Homes & Estates

Property at 117 Renwick St, Newburgh, NY 12550, 3 beds, 1 bath

$200,000

3 beds1 bath1,440 sq ft

117 Renwick St, Newburgh, NY 12550

Listing by RE/MAX Benchmark Realty Group

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 96 Galloway Rd, Warwick, NY 10990, 3 beds, 2 baths

$599,900

3 beds2 baths1,664 sq ft

96 Galloway Rd, Warwick, NY 10990

Listing by BHG Real Estate Green Team

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 37 Edward St, Newburgh, NY 12550, 5 beds, 3 baths

$359,000

5 beds3 baths2,016 sq ft

37 Edward St, Newburgh, NY 12550

Listing by Renaissance Realty Cons Group

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 10 Howe St, Warwick, NY 10990, 3 beds, 1 bath

$449,900

3 beds1 bath1,398 sq ft

10 Howe St, Warwick, NY 10990

Listing by Keller Williams Realty

Property at 106 Station Rd, New Windsor, NY 12553, 4 beds, 5 baths

$1,100,000

4 beds5 baths3,000 sq ft

106 Station Rd, New Windsor, NY 12553

Listing by Houlihan Lawrence

Property at 9 Higgins Trl, Monroe, NY 10950, 2 beds, 1 bath

$165,000

2 beds1 bath588 sq ft

9 Higgins Trl, Monroe, NY 10950

Listing by Keller Williams 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 211 N Miller St, Newburgh, NY 12550, 5 beds, 3 baths

$225,000

5 beds3 baths2,097 sq ft

211 N Miller St, Newburgh, NY 12550

Listing by I Realty LLC

Property at 29 W Lake Rd, Warwick, NY 10990, 3 beds, 2.5 baths

$750,000

3 beds2.5 baths1,732 sq ft

29 W Lake Rd, Warwick, NY 10990

Listing by Howard Hanna Rand Realty

Property at 5 Mills Ave, Middletown, NY 10940, 3 beds, 1.5 baths

$359,999

3 beds1.5 baths1,160 sq ft

5 Mills Ave, Middletown, NY 10940

Listing by Keller Williams Realty

Property at 100 N Orange St, Port Jervis, NY 12771, 4 beds, 2 baths

$389,000

4 beds2 baths1,831 sq ft

100 N Orange St, Port Jervis, NY 12771

Listing by Orange West 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 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 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 7 Center St, Port Jervis, NY 12771, 6 beds, 2 baths

$275,000

6 beds2 baths2,228 sq ft

7 Center St, Port Jervis, NY 12771

Listing by Keller Williams Hudson Valley

Property at 157 Arcadia Rd, Goshen, NY 10924, 10 beds, 5.5 baths

$2,495,000

10 beds5.5 baths6,090 sq ft

157 Arcadia Rd, Goshen, NY 10924

Listing by Iron Valley RE Tri-State

Property at 101 Overlook Pl, Newburgh, NY 12550, 8 beds, 3 baths

$321,000

8 beds3 baths— sq ft

101 Overlook Pl, Newburgh, NY 12550

Listing by Renaissance Realty Cons Group

Property at 120 W Main St, Port Jervis, NY 12771, 3 beds, 2 baths

$375,000

3 beds2 baths1,890 sq ft

120 W Main St, Port Jervis, NY 12771

Listing by Keller Williams Realty

Property at 580 Jersey Ave, Greenwood Lake, NY 10925, 4 beds, 2.5 baths

$860,000

4 beds2.5 baths2,746 sq ft

580 Jersey Ave, Greenwood Lake, NY 10925

Listing by Ridge & Valley RE Corp

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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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