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$620,000
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Property Description
HUGE PRICE REDUCTION- Located in the desirable Monroe-Woodbury School District, this classic 2,220 sq ft colonial offers a rare combination of space, comfort, and future potential. Set on a gentle hill in a picturesque, sidewalk-lined neighborhood, the property features four spacious bedrooms, two bathrooms, and a well-balanced layout that includes a formal dining room, a living room, and a separate family room. The home sits on an unfinished basement, offering excellent storage or the opportunity to create additional living space. There is also room to expand out the back, making this a property with true long-term flexibility. A cozy pellet stove insert brings warmth and character to the main living space, while the kitchen opens to a bright, window-lined breakfast nook-ideal for casual dining and enjoying peaceful backyard views. A screened-in back deck provides a shaded outdoor retreat, leading to a beautifully maintained, heated inground swimming pool-perfect for summer afternoons or quiet night swims under the stars. Enjoy charming views of the town below from the front steps, a peaceful reminder of the home's elevated setting. Additional features include municipal utilities, pull-down access to attic storage, and a two-car garage. The location offers the convenience of walkable access to grocery stores and houses of worship, all within a well-established neighborhood. This is a home with character, comfort, and space to grow-an excellent opportunity in a prime location.
Full Property Details
Full Property Details for 33 Winchester Dr
General
- Price: $620,000
- Taxes: $17,059
- Status: Active
- Type: Single Family
- Source: Long_Island
- MLS ID: 847804
- Updated: 3/16/2026
- Added to Site: 336 day(s) ago
Interior
- Number of Rooms: 13
- Interior Features: Eat-in Kitchen, Formal Dining, Washer/Dryer Hookup
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Pellet Stove
- Appliances: Dishwasher, Range, Refrigerator
- Flooring: Hardwood
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 5
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Electric Heat, In-Ground, Outdoor Pool
Exterior
- Porch/Patio/Deck: Covered, Deck, Porch, Screened
Parking
- Garage: Yes
- Garage Spaces: 2
Location
- County: Orange County
School Information
- High School District: Monroe-Woodbury
- Elementary School: Pine Tree Elementary School
- Middle School: Monroe-Woodbury Middle School
- High School: Monroe-Woodbury High School
Heating & Cooling
- Cooling Type: None
- Heating Type: Oil
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Natural Gas Available
Structural Information
- Architectural Style: Colonial
- Detached/Attached: Detached
- Construction: Frame, Vinyl Siding
- Basement: Yes
- Basement Desc.: Full Basement, Unfinished, Walk-Out Access
- Sq. Ft. Source: Public Records
- Year Built: 1977
Lot Features
- Property View: Neighborhood
- Lot Size (Acres): 0.4591
- Lot Size (Sq. Ft.): 20,000
Financial Considerations
- Taxes Include: Trash
- Tax Amount: $17,059.27
Disclosures and Reports
- Special Conditions: None
- Property ID: 334001-227-000-0004-015.000-0000
- Block: 4
- Lot Number: 15
Listed by Howard Hanna Rand Realty
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Schools
Schools serving 33 Winchester Dr
School District:Monroe-Woodbury Central School District
| Name | Grades | Distance |
|---|---|---|
Monroe Woodbury Middle School 199 Dunderberg Rd, Woodbury, NY 10917 | 6-8 | 2.2 mi |
Monroe Woodbury High School 155 Dunderberg Rd, Woodbury, NY 10917 | 9-12 | 2.3 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 33 Winchester Dr
Date
Details
Price
Change
Source
3/16/2026
Price Reduced
$620,000
-4.6%
MLS
1/14/2026
Price Reduced
$649,900
-1.53%
MLS
11/09/2025
Price Reduced
$660,000
-1.48%
MLS
8/26/2025
Price Reduced
$669,900
-3.6%
MLS
6/08/2025
Price Reduced
$694,900
-4.14%
MLS
5/01/2025
Listed
$724,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 33 Winchester Dr
Year
Property Taxes
Change
Tax Assessment
Change
2021
-100%
$72,100
—
2016
$11,743
-23%
$72,100
—
2020
$15,273
2%
$72,100
—
2018
$14,965
2%
$72,100
—
2017
$14,677
—
$72,100
—
2016
$14,677
—
$72,100
—
2015
$14,735
4%
$72,100
—
2015
$14,230
4%
$72,100
—
2013
$13,723
—
$72,100
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 33 Winchester Dr
33 Winchester Drive, Monroe, NY 10950 (MLS# 847804) is a Single Family property with 5 bedrooms and 2 full bathrooms. 33 Winchester Drive is currently listed for $620,000 and was received on May 01, 2025. Want to learn more about 33 Winchester Drive? Do you have questions about finding other Single Family real estate for sale in Monroe? You can browse all Monroe real estate or contact a Coldwell Banker agent to request more information.
