77 Hillside Rd, Rye, NY 10580
Property image
Property image
OFF MARKET

77 Hillside Rd
Rye, NY 10580

  • 5 Beds
  • 4.5 Baths
  • 5,695 sqft (on 0.85 acres)

$5,026,600

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $32,095/mo*
Refinance Your Home

$5,026,600

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $32,095/mo*
Refinance Your Home
5 Beds
4.5 Baths
5,695 sqft
(on 0.85 acres)

Home Value

Trulia Estimate
$5.03M
Since last month
Increased$64K (+1.3%)
Since last year
Increased$427K (+9.1%)
Since last sale
Increased$1M (+34.8%)
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 +54% in the last 10 years
MonthEstimated value
2026
August 2026$5.12M
July 2026$5.06M
June 2026$4.95M
May 2026$4.87M
April 2026$4.61M
March 2026$4.68M
February 2026$4.74M
January 2026$4.58M
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
0.47
Single-Family Home
$3,450,000
05/29/26
5
4.5
4,612
1 Polly Pk Road, RYE, NY
0.42
Single-Family Home
$2,100,000
09/26/25
5
5.5
5,789
325 Highland Road, Rye, NY
0.61
Single-Family Home
$3,950,000
09/23/25
4
5
4,687
10 Highland Park Pl, Rye, NY
0.37
Single-Family Home
$2,500,000
05/08/26
4
4.5
2,977
14 Lakeside Drive, Rye, NY
0.57
Single-Family Home
$2,400,000
04/07/26
5
8
6,629
1 Oneida Street, Rye, NY
0.40
Single-Family Home
$2,906,024
06/15/26
4
4.5
3,608
95 Dogwood Lane, Rye, NY
0.49
Single-Family Home
$2,702,000
12/08/25
5
2.5
2,949
365 Grace Church Street, Rye, NY
0.88
Single-Family Home
$4,300,000
08/14/26
5
5.5
6,282
40 Mendota Avenue, Rye, NY
0.41
Single-Family Home
$3,200,000
07/06/26
6
5.5
3,902
96 Mendota Avenue, Rye, NY
0.31
Single-Family Home
$1,750,000
02/02/26
5
3.5
3,223

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
55 Hillside Road, Rye, NY 10580
0.05
$4,864,600
6
5.5
4,834
Off Market
61 Grandview Avenue, Rye, NY 10580
0.11
$3,953,600
5
4.5
4,738
Off Market
10 Evergreen Avenue, Rye, NY 10580
0.11
$3,909,500
5
5.5
4,642
Off Market
100 Evergreen Avenue, Rye, NY 10580
0.09
$5,224,700
5
5.5
5,804
Off Market
2 Cope Circle, Rye, NY 10580
0.15
$3,053,200
5
4
3,661
Off Market
17 Hillside Road, Rye, NY 10580
0.12
$4,194,300
6
5.5
5,315
Off Market
50 Ridge Street, Rye, NY 10580
0.18
$6,599,500
7
7.5
8,231
Off Market
106 Wappanocca Avenue, Rye, NY 10580
0.22
$1,474,800
3
2
1,596
Off Market
216 Purchase Street #1F, Rye, NY 10580
0.24
$725,000
2
2
1,266
Recently Sold
216 Purchase Street #S, Rye, NY 10580
0.24
$767,100
3
2
1,400
Off Market
216 Purchase Street #A, Rye, NY 10580
0.24
$678,900
2
2
1,100
Off Market
216 Purchase Street #P, Rye, NY 10580
0.24
$1,615,000
3
2.5
2,010
Recently Sold

Local Information

  • Map ViewExplore the area around 77 Hillside Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1884
Lot Size
0.85 acres
Living Area
5,695 sqft
Price/Sqft
$883

About this House

Retreat, grace, character, sanctuary are words to capture the essence of this admired Rye home. It is set on nearly an acre with a 54' pool & restored carriage house which provides an escape for an office, entertainment, fitness and wellness, or a retreat for extended stay guests. This architecturally significant, fully restored & expanded grand 1884 home has long been admired by passersby. Located in one of Rye s most admired neighborhoods, it offers an easy walk to town & train, with Whole Foods & other shops around the corner. The idyllic drive shaded by two old maples draws you in to the front entrance. The classic porch with all original details, is a favorite hang-out for early morning coffee. Situated on one of the highest points in Rye, there is often a gentle breeze even when it s hot & sultry in town. The back garden oasis is an unexpected & welcoming surprise, a touch of East Hampton in Rye. The pool with large pergola, vegetable garden, & stunning landscaping that would take decades to cultivate, adorn the yard. Outdoor dinners in this tranquil setting are simply magical, enhanced by vibrant sunsets from this elevated perch. A home like this does not come to market often. The owners have stewarded this magnificent home for three decades & have been rewarded with priceless memories.
77 Hillside Rd, Rye, NY 10580 is a 5 bedroom, 5 bathroom, 5,695 sqft single-family home built in 1884. It last sold for $3,800,000 on Aug 15, 2020. It is currently off market. The Trulia Estimate is $5,026,600, with a rent estimate of $24,523/month.

Home Details for 77 Hillside Rd

Property Information

Year Built
Year Built: 1884
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Interior Features

Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Exterior: Wood

Community

Units in Building: 1

Lot Information

Lot Area: 0.85 acres

Price and Tax history

DateEventPrice
Aug 15, 2020
Source: OneKey® MLS as distributed by MLS GRID #H6052324
Sold
$3,800,000
Jul 27, 2020
Source: Agent Provided
Pending
$3,795,000
Jul 16, 2020
Source: Agent Provided
Listed For Sale
$3,795,000

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

Frequently asked questions about 77 Hillside Rd

  • What is 77 Hillside Rd estimated to be worth?
    Trulia's estimated value for 77 Hillside Rd in Rye, NY is $5,026,600.
  • What is the price history for 77 Hillside Rd?
    77 Hillside Rd in Rye, NY last sold for $3,800,000 in August 2020.
  • 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.
  • How big is the lot at 77 Hillside Rd?
    The lot at 77 Hillside Rd in Rye, NY is about 0.85 acres (37,026 sq ft).

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Off Market Homes Near 77 Hillside Rd

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