5 Winthrop Drive
Rye Brook, NY 10573
6 Beds
5 Baths
5,672 sqft (on 1.07 acres)
6 Beds
5 Baths
5,672 sqft
(on 1.07 acres)
Local Information
- Map ViewExplore the area around 5 Winthrop Drive.
- Schools1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Description
A rare & exceptional 6 bedroom, 5 bath colonial home nestled in the coveted Pine Ridge section of Rye Brook. This unique residence is situated on over a 1-acre lush flat property which provides an unparalleled level of luxury & privacy. Step inside this elegant home to discover a stunning array of modern features. The center of the home is the impressive custom kitchen w/ heated floors designed by Georgio with Quartzite countertops, custom cabinetry and high end appliances. The wall of glass doors from the kitchen leads to the blue stone patio for the ultimate entertaining flow. The show-stopping family room impresses with soaring ceilings & designer finishes. A first floor guest bedroom provides the comfort for various lifestyle needs. Don't miss the inviting office that actually makes you want to work! Upstairs you will find the primary bedroom which is a private sanctuary w/ high ceilings, large closets & an unparalleled new custom bathroom. 4 addl bedrooms & 2 full baths give you all the space you need. The beautiful gunite pool creates a resort-like atmosphere for outdoor entertaining. Featuring a rare three-car garage, large mudroom, formal living room, large dining room, PLUS bonus room for recreation, this home effortlessly combines elegance with modern functionality. Situated on a quiet street close to the park, this property offers a once-in-a-lifetime opportunity for refined living. Don't miss the chance to experience the epitome of luxury and style in this exclusive home. Additional Information: ParkingFeatures:3 Car Attached,
5 Winthrop Drive, Rye Brook, NY 10573 is a 6 bedroom, 5 bathroom, 5,672 sqft single-family home built in 1900. It last sold for $2,570,000 on Jun 7, 2024 (7% below the $2,775,000 asking price). It is currently off market. The Trulia Estimate is $3,066,700, with a rent estimate of $14,572/month.
Home Highlights
Parking
3 Parking Spaces
Outdoor
Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 5 Winthrop Drive
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Interior Details Basement: Crawl SpaceNumber of Rooms: 15 |
Beds & Baths Number of Bedrooms: 6Number of Bathrooms: 5Number of Bathrooms (full): 5 |
Dimensions and Layout Living Area: 5672 Square Feet |
Appliances & Utilities Utilities: Trash Collection PublicAppliances: Gas Water Heater |
Heating & Cooling Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace |
Levels, Entrance, & Accessibility Stories: 2Levels: Two |
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Parking & Garage No CarportParking Spaces: 3Parking: Attached |
Pool Pool: In GroundPool |
Frontage Responsible for Road Maintenance: Public Maintained Road |
Water & Sewer Sewer: Public Sewer |
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Year Built Year Built: 1900Year Renovated: 2022 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Colonial |
Building Construction Materials: Brick, ClapboardNot Attached Property |
Property Information Condition: ActualParcel Number: 48051350000004200100470000000 |
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Price List Price: $2,775,000 |
Status Change & Dates Off Market Date: Fri Mar 29 2024 |
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MLS Status: Sold |
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Direction & Address City: Rye Brook |
School Information Elementary School: Bruno M Ponterio Ridge Street SchooJr High / Middle School: Blind Brook-Rye Middle SchoolHigh School: Blind Brook High SchoolHigh School District: Blind Brook-Rye |
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Building Area Building Area: 5672 Square Feet |
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Community Features: ParkNot Senior Community |
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No HOA |
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Lot Area: 1.0722 Acres |
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Listing Agreement Type: Exclusive Right To SellListing Terms: Cash |
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BasementMls Number: H6289442Attic: WalkupAttribution Contact: (914) 727-0169Showing AttendedShowing Requirements: Lockbox |
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HOA Amenities: Park |
Last check for updates: about 14 hours ago
Listed by Kori Sassower, (914) 727-0169
Compass Greater NY, LLC, (914) 223-7623
Bought with: Kori Sassower, (914) 727-0169, Compass Greater NY, LLC, (914) 223-7623
Source: OneKey® MLS as distributed by MLS GRID, MLS#H6289442
Price History for 5 Winthrop Drive
| Date | Price | Event | Source |
|---|---|---|---|
| 06/07/2024 | $2,570,000 | Sold | OneKey® MLS as distributed by MLS GRID #H6289442 |
| 03/29/2024 | $2,775,000 | Pending | OneKey® MLS as distributed by MLS GRID #H6289442 |
| 02/26/2024 | $2,775,000 | Listed For Sale | OneKey® MLS as distributed by MLS GRID #H6289442 |
| 06/28/2013 | $1,800,000 | Sold | OneKey® MLS as distributed by MLS GRID #H3305355 |
| 03/19/2013 | $1,675,000 | ListingRemoved | Agent Provided |
| 02/28/2013 | $1,675,000 | Listed For Sale | Agent Provided |
| 11/23/2004 | $1,600,000 | Sold | N/A |
| 05/17/1996 | $655,000 | Sold | N/A |
Market trends in Rye Brook
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
18
2MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $2,505,700 |
Home facts updated by county records
Comparable Sales for 5 Winthrop Drive
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.17 | Single-Family Home | $3,020,000 | 07/29/25 | 6 | 5.5 | 5,890 | |
0.34 | Single-Family Home | $2,455,000 | 07/14/25 | 5 | 4.5 | 3,412 | |
0.39 | Single-Family Home | $3,450,000 | 06/26/26 | 5 | 6 | 5,590 | |
0.36 | Single-Family Home | $1,190,000 | 06/15/26 | 4 | 4.5 | 5,616 | |
0.53 | Single-Family Home | $2,975,000 | 12/22/25 | 5 | 5.5 | 5,091 | |
0.17 | Single-Family Home | $2,170,000 | 04/09/26 | 4 | 3.5 | 3,185 | |
0.17 | Single-Family Home | $2,020,000 | 07/29/25 | 3 | 3.5 | 4,451 | |
0.35 | Single-Family Home | $1,200,000 | 10/23/25 | 6 | 7 | 5,590 | |
0.35 | Single-Family Home | $2,250,000 | 04/07/26 | 5 | 3.5 | 3,297 |
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Assigned Schools
These are the assigned schools for 5 Winthrop Drive.
- Blind Brook High School
- 9-12
- Public
- 402 Students
10/10GreatSchools RatingParent Rating AverageThe high school has been great for our daughters growth and development.Parent Review3y ago - Bruno M Ponterio Ridge Street School
- K-5
- Public
- 598 Students
10/10GreatSchools RatingParent Rating AverageThe Principal is terrible. Inconsiderate and unapologetic and takes no accountability. I paid for my children to attend this school and they couldn’t provide my children with the correct accommodations for them to succeed the way I knew they could, simply because we didn’t live in district. She decided 3 days before the school year was over to hold a meeting and tell me my youngest would be held back with no choice. I refused to pay because I was well aware my child needed accommodations that they failed to provide. They just blamed my child for their lack of and decided she wasn’t moving forward. I’m happy to say I put my children in the Port Chester district and they were beyond amazing from the second my children and I stepped foot in that school. The principals and teachers all worked together with me and my children and they are both thriving. With the right accommodations in place and really getting to know your children makes a world of a difference. As every and any professional in a school environment should know every child learns different and some children need a little extra help. Bruno M Ponterio Ridge School should be ashamed of themselves for failing a student that is succeeding in all the right ways with the right school that cared enough to really understand my children.Parent Review1y ago - Blind Brook Rye Middle School
- 6-8
- Public
- 287 Students
10/10GreatSchools RatingParent Rating AverageGreat school, Nationally ranked, moved here for the school. Not disappointed. The kids are pushed by the school. After middle school, the High School pushes just as hard, Excellence is expected. These kids are EXPECTED to get into Ivy League Schools, all other school are "fallback schools" I HAVE HEARD THIS WITH MY OWN EARS from several parentsParent Review12y ago 
Check out schools near 5 Winthrop Drive.
What Locals Say about Rye Brook
At least 100 Trulia users voted on each feature.
84 % Say it's dog friendly
80 % Say people would walk alone at night
78 % Say yards are well-kept
76 % Say car is needed
75 % Say parking is easy
72 % Say there's holiday spirit
70 % Say there are sidewalks
68 % Say it's quiet
67 % Say it's walkable to restaurants
65 % Say they plan to stay for at least 5 years
65 % Say streets are well-lit
61 % Say it's walkable to grocery stores
57 % Say kids play outside
53 % Say neighbors are friendly
46 % Say there's wildlife
37 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
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Based on information submitted to the MLS GRID as of 2026-07-11 11:13:24 PDT 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. Some IDX listings have been excluded from this website. Click here for more information