55 Hillside Road, Rye, NY 10580
OFF MARKET

55 Hillside Road
Rye, NY 10580

  • 6 Beds
  • 5.5 Baths
  • 4,834 sqft (on 1.50 acres)

$4,652,900

Trulia Estimate
as of May 31, 2026
Est. Refi. Payment $28,744/mo*
Refinance Your Home

$4,652,900

Trulia Estimate
as of May 31, 2026
Est. Refi. Payment $28,744/mo*
Refinance Your Home
6 Beds
5.5 Baths
4,834 sqft
(on 1.50 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Unparalleled elegance in this 6-bedroom brick Georgian Colonial, reminiscent of an English estate on rare 1.5 private & picturesque property. A long private drive bordered by flowering shrubs, beautiful circular entrance w/ artistically landscaped medallion. Unique front-to-back reception rooms, center hall layout, high ceilings throughout.
Magnificent inground pool & hot tub surrounded by gracious terrace, putting green/sand trap, tennis backboard/basketball court. Sq ftge does NOT include additional 875 legal sq ft in basement.
With its prime location, residents enjoy easy access to the station and a short stroll to the quaint village of Rye with its charming shops and restaurants. Experience the epitome of luxury living in this exquisite Georgian Colonial, where every detail is designed for comfort and sophistication. Inclusions galore and Furniture can also be purchased. Additional Information: Amenities:Marble Bath,Storage,ParkingFeatures:2 Car Detached,
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from July 11, 2025

Home Highlights

Parking
2 Parking Spaces
Outdoor
Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 55 Hillside Road

Interior Features

Interior Details
Basement: Finished,FullNumber of Rooms: 15
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4834 Square Feet
Appliances & Utilities
Utilities: Trash Collection PublicAppliances: Stainless Steel Appliance(s), Gas Water Heater, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer, Wine RefrigeratorDishwasherDisposalDryerLaundry: InsideMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace
Windows, Doors, Floors & Walls
Window: Drapes, Blinds, Storm Window(s), Oversized WindowsFlooring: Hardwood, Carpet
Levels, Entrance, & Accessibility
Stories: 3Levels: Three Or MoreFloors: Hardwood, Carpet
Security
Security: Security System

Exterior Features

Exterior Home Features
Patio / Porch: TerraceExterior: Basketball Court, Courtyard, Awning(s), Basketball Hoop, Gas Grill, Speakers
Parking & Garage
No CarportParking Spaces: 2Parking: Detached
Pool
Pool: In GroundPool
Frontage
Responsible for Road Maintenance: Public Maintained Road
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 182

Property Information

Year Built
Year Built: 1922
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Colonial
Building
Building: Awning(s)Construction Materials: BrickNot Attached Property
Property Information
Condition: ActualIncluded in Sale: Fireplace Equip, Flat Screen TV Bracket, Light Fixtures, Oven/Range, PlaysetParcel Number: 1400139015000010000025

Price & Status

Price
List Price: $4,895,000
Status Change & Dates
Off Market Date: Thu Feb 06 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: Rye
School Information
Elementary School: MidlandJr High / Middle School: Rye Middle SchoolHigh School: Rye High SchoolHigh School District: Rye City

Building

Building Area
Building Area: 4834 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 1.5 Acres

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: H6320645Attic: Full, WalkupAttribution Contact: 914 9670059Showing AttendedShowing Requirements: Call Listing Agent
Last check for updates: about 4 hours ago
Listed by Michele Flood, (914) 420-6468
Coldwell Banker Realty, (914) 967-0059
Bought with: Julia K. Bieber, (917) 734-2941, Compass Greater NY, LLC, (914) 353-5570
Source: OneKey® MLS as distributed by MLS GRID, MLS#H6320645

Price History for 55 Hillside Road

DatePriceEventSource
05/05/2025$4,400,000Sold
OneKey® MLS as distributed by MLS GRID #H6320645
02/13/2025$4,895,000PendingOneKey® MLS as distributed by MLS GRID #H6320645
02/07/2025$4,895,000ListingRemovedOneKey® MLS as distributed by MLS GRID #H6320645
01/25/2025$4,895,000PriceChange
OneKey® MLS as distributed by MLS GRID #H6320645
12/12/2024$5,400,000PriceChange
OneKey® MLS as distributed by MLS GRID #H6320645
09/19/2024$5,875,000PriceChange
OneKey® MLS as distributed by MLS GRID #H6320645
08/08/2024$6,100,000Listed For SaleOneKey® MLS as distributed by MLS GRID #H6320645
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Property Tax and Assessment

Year2025
Tax
Assessment$67,200
Home facts updated by county records

Comparable Sales for 55 Hillside Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
18 Lakeside Drive, Rye, NY
0.43
Single-Family Home
$3,450,000
05/29/26
5
4.5
4,612
325 Highland Road, Rye, NY
0.56
Single-Family Home
$3,950,000
09/23/25
4
5
4,687
1 Polly Pk Road, RYE, NY
0.37
Single-Family Home
$2,100,000
09/26/25
5
5.5
5,789
472 Purchase Street, Rye, NY
0.65
Single-Family Home
$2,856,651
07/17/25
6
4.5
5,243
14 Lakeside Drive, Rye, NY
0.53
Single-Family Home
$2,400,000
04/07/26
5
8
6,629
23 Mohawk Street, Rye, NY
0.32
Single-Family Home
$2,210,000
07/11/25
6
4
3,285

Nearby homes

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Assigned Schools

These are the assigned schools for 55 Hillside Road.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Rye

At least 150 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there's holiday spirit

  • 81 % Say people would walk alone at night

  • 81 % Say kids play outside

  • 81 % Say yards are well-kept

  • 77 % Say car is needed

  • 77 % Say parking is easy

  • 72 % Say it's quiet

  • 71 % Say streets are well-lit

  • 69 % Say it's walkable to restaurants

  • 66 % Say there's wildlife

  • 64 % Say they plan to stay for at least 5 years

  • 62 % Say there are sidewalks

  • 57 % Say neighbors are friendly

  • 56 % Say there are community events

  • 44 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Zjstempel
    "There are a lot of good public parks and nice sidewalks to walk on. also a lot of people own their own dogs"
    0
    Flag
  • Dbenzanava
    "Dogs owners would like it very much. There are special Dog bakeries & pet shops catering to your pet. "
    0
    Flag
  • Brianrollins1959
    "When we walk our dog.There is always someone else walking their dog.Every one usually picks up after their dog "
    0
    Flag
  • Brianrollins1959
    "I get on 287 in the AM . It’s a 15 minute ride to White Plains. But when l come home at 12:30pm . Every body is stressed out. And driving on my bumper. I have to watch because they almost running into me "
    3
    Flag
  • Felix Vazquez Jr
    "They send helpful information in the mailbox which allows us to find events that are happening in the town"
    2
    Flag
  • Trulia User
    "Very kid friendly - just note it’s not the Rye school system. Nice walking area around the Neightborhood"
    1
    Flag
  • Patricia I.
    "Halloween window displays on Puchase street by the school children. Christmas street fair on Purchase st."
    1
    Flag
  • Nickalvarez4
    "7 minutes to metro north. Good parking at train station. Trains on schedule. 37 min train ride in to Grand Central."
    0
    Flag
  • Ltifdle
    "Right now my commute is down the staircase. Otherwise very convenient to all highways (i287, hutch, i95) and trains to city."
    0
    Flag
  • Ltifdle
    "Homes have large yards where it’s safe for children to play. Stores and restaurants are conveniently nearby. Easy access to major roadways and trains to city."
    0
    Flag
  • Cleary.aileen
    "I live here and it’s really a great place to live , lots of great things go on here and great community spirit "
    1
    Flag
  • Rosemary
    "Green community lots of parks great schools. Nice main avenue luxury shopping. Bistro restaurants. Some Catholic Church around. "
    0
    Flag
  • Heatherosemusic
    "Grew up here with my grandma and I love it. It’s the quintessential suburbs with proximity to Manhattan, a quaint village, great schools, a beach, an amusement park and so much more. The ideal neighborhood to raise a family. "
    6
    Flag
  • Manonbartels2008
    "Short and easy, fast commute. Plenty of trains, on time and easy access. Parking at station is hard due to permit wait list."
    1
    Flag
  • Fernando
    "I love Rye. It is a very quiet and peaceful neighborhood. the place is nice with good restaurants. "
    1
    Flag
  • Trulia User
    "Rye has Metro North station with direct access to city. Also there are 2 major highways with 4 exits in Rye."
    1
    Flag
  • Dan K.
    "Extremely safe and well kept place to live and be! Definitely a higher price point than even other parts of Westchester, but it is what it promotes itself to be. "
    1
    Flag
  • Ltifdle
    "Wonderful neighborhood to raise a family. Can walk to the club for all types of sports year-round. Many choices for great schools. Close to town, doctors, worship."
    0
    Flag
  • Michael C.
    "Extremely beautiful every season. Very quiet, family friendly to a fault. Winding roads assure privacy and security. "
    3
    Flag
  • Lriddle
    "My neighborhood is convenient to Westchester county, greenwich / Stamford by car and or nyc by train."
    0
    Flag
  • John J.
    "It’s a pretty dog friendly neighborhood. Town park with great dog community few blocks away. Few places in town have water bowls out front. I’m guessing every 3rd house has dog. "
    2
    Flag
  • Lriddle
    "Storybook Main Street with shops and restaurants. Very convenient commuting to work opportunities in Westchester, Connecticut and nyc."
    0
    Flag
  • Cchidiya
    "everything is convenient and easily accessible even by foot. it's a beautiful neighborhood. people are friendly, restaurants are organic, shopping is amazing. there is always free parking everywhere."
    0
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  • Contessa1313
    "Best of all possible areas for schools, trains, buses, walking, bicyling, water sports, gardening,etc."
    0
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Homes for sale near 55 Hillside Road

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Off Market Homes Near 55 Hillside Road

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Based on information submitted to the MLS GRID as of 2026-02-06 15:18:24 PST. 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

Homes for rent near 55 Hillside Road

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55 Hillside Road, Rye, NY 10580 is a 6 bedroom, 6 bathroom, 4,834 sqft single-family home built in 1922. This property is not currently available for sale. 55 Hillside Road was last sold on May 5, 2025 for $4,400,000 (10% lower than the asking price of $4,895,000). The current Trulia Estimate for 55 Hillside Road is $4,652,900.