55 Hillside Road, Rye, NY 10580
OFF MARKET

$4,859,000

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

55 Hillside Road, Rye, NY 10580

Est. Refi. Payment $31,489/mo*
Refinance Your Home
Currently Off Market - Sold May 5, 2025 for $4,400,000

Home Value

Trulia Estimate
$4.86M
Since last month
Increased$94K (+2%)
Since last year
Increased$369K (+8.2%)
Since last sale
Increased$459K (+10.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +21% in the last 10 years
MonthEstimated value
2026
August 2026$4.86M
August 2026$4.84M
July 2026$4.77M
June 2026$4.72M
May 2026$4.64M
April 2026$4.65M
March 2026$4.67M
February 2026$4.52M
January 2026$4.59M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
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
19 Onondaga Street, Rye, NY
0.35
Single-Family Home
$3,900,000
08/24/26
5
5
3,784
40 Mendota Avenue, Rye, NY
0.41
Single-Family Home
$3,200,000
07/06/26
6
5.5
3,902
81 Wappanocca Avenue, Rye, NY
0.25
Single-Family Home
$3,175,000
08/28/26
4
3
3,735
14 Lakeside Drive, Rye, NY
0.53
Single-Family Home
$2,400,000
04/07/26
5
8
6,629
1 Oneida Street, Rye, NY
0.37
Single-Family Home
$2,906,024
06/15/26
4
4.5
3,608

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
100 Evergreen Avenue, Rye, NY 10580
0.07
$5,217,200
5
5.5
5,804
Off Market
17 Hillside Road, Rye, NY 10580
0.07
$4,218,900
6
5.5
5,315
Off Market
50 Ridge Street, Rye, NY 10580
0.13
$6,590,100
7
7.5
8,231
Off Market
10 Evergreen Avenue, Rye, NY 10580
0.12
$3,919,800
5
5.5
4,642
Off Market
61 Grandview Avenue, Rye, NY 10580
0.13
$3,967,100
5
4.5
4,738
Off Market
335 Purchase Street, Rye, NY 10580
0.19
$4,069,300
6
4.5
5,038
Off Market
2 Cope Circle, Rye, NY 10580
0.20
$3,010,000
5
4
3,661
Off Market
145 Wappanocca Avenue, Rye, NY 10580
0.19
$3,547,300
5
5
4,345
Off Market
106 Wappanocca Avenue, Rye, NY 10580
0.21
$1,469,200
3
2
1,596
Off Market
55 Meadow Place, Rye, NY 10580
0.22
$2,103,800
6
3.5
2,308
Off Market
94 Wappanocca Avenue, Rye, NY 10580
0.23
$1,931,000
4
2.5
2,947
Off Market

Local Information

  • Map ViewExplore the area around 55 Hillside Road.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1922
1.5 acre lot
4,834 sqft
$1,005/sqft
2 Parking Spaces

About this House

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,
55 Hillside Road, Rye, NY 10580 is a 6 bedroom, 6 bathroom, 4,834 sqft single-family home built in 1922. It last sold for $4,400,000 on May 5, 2025 (10% below the $4,895,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,859,000.
Last check for updates: about 7 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

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

Price and Tax history

DateEventPrice
May 5, 2025
Source: OneKey® MLS as distributed by MLS GRID #H6320645
Sold
$4,400,000
Feb 13, 2025
Source: OneKey® MLS as distributed by MLS GRID #H6320645
Pending
$4,895,000
Feb 7, 2025
Source: OneKey® MLS as distributed by MLS GRID #H6320645
ListingRemoved
$4,895,000
Jan 25, 2025
Source: OneKey® MLS as distributed by MLS GRID #H6320645
PriceChange
$4,895,000
Price decreased by 9%
Dec 12, 2024
Source: OneKey® MLS as distributed by MLS GRID #H6320645
PriceChange
$5,400,000
Price decreased by 8%

Market trends in Rye

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.44M
Sale-to-List Price
105.3%
Price per sq ft
$743
Available listings
39
2MoM

Around this home

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
    Flag
  • Contessa1313
    "Best of all possible areas for schools, trains, buses, walking, bicyling, water sports, gardening,etc."
    0
    Flag

LGBTQ Local Legal Protections

Based on information submitted to the MLS GRID as of 2026-09-05 15:28:31 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

Frequently asked questions about 55 Hillside Road

  • What is 55 Hillside Road estimated to be worth?
    Trulia's estimated value for 55 Hillside Road in Rye, NY is $4,859,000.
  • What is the price history for 55 Hillside Road?
    55 Hillside Road in Rye, NY last sold for $4,400,000 in May 2025.
  • Is Rye a buyer's or seller's market?
    Rye is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Rye?
    The median sale price in Rye is $2.44M.
  • Does 55 Hillside Road have air conditioning?
    Yes, 55 Hillside Road in Rye, NY has air conditioning.
  • Does 55 Hillside Road have a pool?
    Yes, 55 Hillside Road in Rye, NY has a pool.

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