Vintage homes for sale & real estate in Woodbury, NY

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ABOUT THIS HOME
Vintage Home for sale in Woodbury, NY:
Welcome to 17 Pine Hill! Escape to this stunning ranch-style home situated on a serene 1.3-acre property! As you step inside, you'll be greeted by the warmth of the living room, complete with a cozy fireplace and inviting ambiance. Enjoy meals in the charming dinette, which opens up to a picturesque deck perfect for taking in the surroundings. The heart of the home is the spacious open-concept kitchen, featuring granite countertops, a large island, and cathedral ceilings that add to the sense of grandeur. The adjacent family room boasts an abundance of windows, cathedral ceilings, and a fireplace, creating a bright and airy atmosphere filled with natural light. Throughout the main living a

$625,000

2 beds1 bath1,224 sq ft

17 Pine Hill Rd, Highland Mills, NY 10930

Hardwood flooring • Open-concept kitchen • 3-car garage

Listing by Preferred Properties Real Esta

ABOUT THIS HOME
Vintage Home for sale in Woodbury, NY:
Charming Cape in Highland Mills – A Gardener’s Paradise with Modern Upgrades! Nestled in the scenic mountains of Highland Mills, this enchanting “Little Yellow House” sits proudly on a corner lot, offering the perfect blend of character, comfort, and modern convenience. Boasting 4 bedrooms and 1 bath, this Cape-style home is a true retreat for gardeners, entertainers, and families alike. Step outside to your private oasis: a lush, landscaped garden featuring cherry, peach, and Japanese pine trees, vibrant perennial floral beds framed with hydrangeas, peonies, and roses, and even a small vegetable garden for homegrown delights. A charming front patio welcomes morning

$447,000

4 beds1 bath1,225 sq ft

2 Cedar Rd, Highland Mills, NY 10930

8,970 sq ft lot • Built 1955 • Listed 32 days

Listing by Z Wisdom Realty Inc.

ABOUT THIS HOME
Vintage Home for sale in Woodbury, NY:
Discover the charm of this country-style house in Central Valley, situated in the historic village area. You'll be close to shopping, restaurants, Woodbury Commons, and the Monroe-Woodbury School District. This two-story colonial features a freshly painted interior with cozy accents, a beautiful staircase, an enclosed front porch, and an updated kitchen. Enjoy the spacious rear yard deck overlooking a babbling brook, a large second-floor bathroom, and a central hot air heating system. This delightful home is move-in ready and offers convenient access to all you need.

$369,000

2 beds1 bath1,500 sq ft

72 Smith Clove Rd, Central Valley, NY 10917

Country-style house • Babbling brook • Updated kitchen

Listing by eRealty Advisors, Inc

ABOUT THIS HOME
Vintage Home for sale in Woodbury, NY:
Welcome to 132 Ridge Road, a charming colonial located in the center of Highland Mills. Bright living areas, a formal dining room, and a comfortable eat-in kitchen combine to create a home with 3 bedrooms and 1.5 bathrooms that combines comfort and character. It's ideal for weekend barbecues or peaceful mornings with coffee on the porch because it's situated on a large lot with lots of greenery. This house, which is close to Woodbury Commons, provides the perfect mix of convenience and tranquil living. Come see it and fall in love!

$465,000

3 beds1.5 baths1,751 sq ft

132 Ridge Rd, Highland Mills, NY 10930

Formal dining room • Lots of greenery • Large lot

Listing by MS Realty Group USA, Inc

ABOUT THIS HOME
Vintage Home for sale in Woodbury, NY:
Seize this incredible opportunity to own a charming property that’s priced to sell!! Bathed in natural sunlight, this delightful home offers a warm and inviting atmosphere, perfect for creating lasting memories. Whether you're looking to invest or fulfill your dream of homeownership, this prime location balances comfort and potential seamlessly. Act fast—this gem won’t last long!

$310,000

3 beds1 bath1,088 sq ft

172 County Route 105, Highland Mills, NY 10930

0.32 acre lot • Built 1940 • Listed 164 days

Listing by Flag Realty Group

Property at 24 Jill Rd, Highland Mills, NY 10930, 6 beds, 3.5 baths

$1,950,000

6 beds3.5 baths6,576 sq ft

24 Jill Rd, Highland Mills, NY 10930

Listing by Howard Hanna Rand Realty

Property at 241 Smith Clove Rd, Highland Mills, NY 10930, 2 beds, 1 bath

$400,000

2 beds1 bath1,000 sq ft

241 Smith Clove Rd, Highland Mills, NY 10930

Listing by HomeSmart Homes & Estates

Property at 93 Weygant Hl, Highland Mills, NY 10930, 3 beds, 2 baths

$459,999

3 beds2 baths1,512 sq ft

93 Weygant Hl, Highland Mills, NY 10930

Listing by RE/MAX Benchmark Realty Group

Property at 24 Laura Ln, Central Valley, NY 10917, 4 beds, 1 bath

$799,000

4 beds1 bath1,400 sq ft

24 Laura Ln, Central Valley, NY 10917

Listing by Artisan Realty

Property at Undisclosed address, Highland Mills, NY 10930, 14 beds, 6.5 baths

$14,000,000

14 beds6.5 baths10,041 sq ft

Undisclosed address, Highland Mills, NY 10930

Listing by Keller Williams Hudson Valley

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ABOUT THIS HOME
Vintage Home for sale in Woodbury, NY:
Spacious Home on 2 Acres! Set back from the road for added privacy, this 3,684 sq ft home offers 6 bedrooms, 3.5 baths, and a fenced-in backyard with patio. The main level features a kitchen, dinette, living room, laundry closet, 2 bedrooms, and 1.5 baths. Upstairs includes 4 more bedrooms, 2 full baths, which includes the large primary suite with walk-in closet and private bath. The full unfinished basement provides great potential. Solar panels add energy efficiency. While some minor maintenance is needed, the home’s size, layout, and setting offer endless possibilities to make it your own.

$849,000

6 beds3.5 baths3,684 sq ft

1433 Route 208, Washingtonville, NY 10992

2 acres • Fenced-in backyard • Solar panels

Listing by Priority Management

ABOUT THIS HOME
Vintage Home for sale in Woodbury, NY:
Welcome to this beautiful 3-bedroom, 2 full-bathroom colonial situated on 1.2 acres of private land. This home features numerous recent improvements such as new windows (2018), back roof (2015) and a forced air/central air system (2013). The home has also been painted recently. Enter through the quiet, enclosed sunroom or the enclosed side entrance. The foyer opens to a first-floor bedroom, a full bathroom with a tub and a laundry room. From there, flow into the inviting living room and dining area highlighted by natural wood beams, hardwood floors and a closet. The spacious kitchen offers stainless steel appliances and a sliding glass door leading to the backyard. Upstairs you'll find two

$699,900

3 beds2 baths1,888 sq ft

161 Wayne Ave, Stony Point, NY 10980

Enclosed sunroom • Recent improvements • Forced air system

Listing by Biagini Realty

OPEN DEC 7, 12PM TO 1:30PM

ABOUT THIS HOME
Vintage Home for sale in Woodbury, NY:
Don't miss out on this STUNNING RENOVATED GEM at 459 Clove Rd, Monroe! - 3 spacious bedrooms - Living room & dining room - Cozy fireplace - 1.5 bathrooms - 1.5 acres of PRIVATE, secluded bliss - Upgraded & renovated to perfection Come see it before it's GONE! Schedule a showing today and make this beauty yours!

$650,000

3 beds1.5 baths1,665 sq ft

459 Clove Rd, Monroe, NY 10950

1.5 acre lot • Built 1950 • Listed 19 days

Listing by eRealty Advisors, Inc

ABOUT THIS HOME
Vintage Home for sale in Woodbury, NY:
Come take a look on this beautiful property!

$415,000

3 beds1 bath1,080 sq ft

8 Mid Oaks St, Monroe, NY 10950

0.23 acre lot • Built 1960 • Listed 20 days

Listing by eRealty Advisors, Inc

ABOUT THIS HOME
Vintage Home for sale in Woodbury, NY:
Location, location, location! Great opportunity to own this fully renovated Single Family house in the heart of Monroe!! Schedule your appointment before it's gone!

$259,900

3 beds1 bath784 sq ft

22 Sylvan Trl, Monroe, NY 10950

Fully renovated • 6,000 sq ft lot • Built 1946

Listing by P R O Links Realty Inc

ABOUT THIS HOME
Vintage Home for sale in Woodbury, NY:
Looking for a family compound? Nestled on 5.2 acres in the Town of Monroe! Built in 1935, This Stone 4 Bedroom, 2.5 Bathroom Cape Cod might be for you! Formal living room with stone fireplace, formal dining room, Family room with stone fireplace, Hardwood flooring throughout, and 3 season sun room. Spacious kitchen with plenty of counter & cabinet space. Walk out your rear door & enjoy your morning coffee taking in the mountain views. Upper level consists of 4 bedrooms & full bath. Lower level with rec room. In addition to the main house is a 2 bedroom 1 bath Stone ranch guest house. Need room for storage or a workshop? There is a massive 4 bay Garage/Barn that would be pe

$695,000

4 beds2.5 baths2,732 sq ft

158 Harriman Heights Rd, Monroe, NY 10950

Hardwood flooring • 3 season sun room • Rec room

Listing by River Realty Services, Inc.

Property at 469 Hillside Rd, Monroe, NY 10950, 4 beds, 2 baths

$520,000

4 beds2 baths1,730 sq ft

469 Hillside Rd, Monroe, NY 10950

Listing by MK Realty Inc

Property at 5 Tappan Dr, Monroe, NY 10950, 5 beds, 2 baths

$867,000

5 beds2 baths2,000 sq ft

5 Tappan Dr, Monroe, NY 10950

Listing by eRealty Advisors, Inc

Property at 157 Stage Rd, Monroe, NY 10950, 2 beds, 1.5 baths

$499,900

2 beds1.5 baths1,120 sq ft

157 Stage Rd, Monroe, NY 10950

Listing by Weichert Realtors

Property at 12 Mid Oaks Dr, Monroe, NY 10950, 3 beds, 2 baths

$485,500

3 beds2 baths1,472 sq ft

12 Mid Oaks Dr, Monroe, NY 10950

Listing by Century 21 Realty Center

Property at 85 Duelk Ave, Monroe, NY 10950, 3 beds, 1 bath

$769,000

3 beds1 bath960 sq ft

85 Duelk Ave, Monroe, NY 10950

Listing by MS Realty Group USA, Inc

Property at 34 Laurel Trl, Monroe, NY 10950, 3 beds, 1 bath

$223,500

3 beds1 bath960 sq ft

34 Laurel Trl, Monroe, NY 10950

Listing by Q Home Sales

Property at 65 Hawxhurst Rd, Monroe, NY 10950, 5 beds, 1.5 baths

$639,000

5 beds1.5 baths2,600 sq ft

65 Hawxhurst Rd, Monroe, NY 10950

Listing by Keller Williams Realty

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 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 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 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 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 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

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 Woodbury

There are currently 10 vintage homes for sale in Woodbury at a median listing price of $625K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Woodbury stay on the market for 79 days and receive 2 offers. Popular neighborhoods include Central Valley, and Highland Mills. This map is refreshed with the newest listings in Woodbury every 15 minutes.

In the past month, 12 homes have been sold in Woodbury. In addition to houses in Woodbury, there was also 1 condo, 2 townhouses, and 2 multi-family units for sale in Woodbury last month. Find your dream home in Woodbury 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 Woodbury are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Woodbury. Our Woodbury real estate stats and trends will give you more information about home buying and selling trends in Woodbury. If you're looking to sell your home in the Woodbury area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Woodbury with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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