77 Hillside Rd, Rye, NY 10580
OFF MARKET

77 Hillside Rd
Rye, NY 10580

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

$4,888,600

Trulia Estimate
as of May 26, 2026
Est. Refi. Payment $30,399/mo*
Refinance Your Home

$4,888,600

Trulia Estimate
as of May 26, 2026
Est. Refi. Payment $30,399/mo*
Refinance Your Home
5 Beds
4.5 Baths
5,695 sqft
(on 0.85 acres)

Local Information

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

Description

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.
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.

Home Highlights

Parking
No Info
Outdoor
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HOA
None
Price/Sqft
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Listed
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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 History for 77 Hillside Rd

DatePriceEventSource
08/15/2020$3,800,000Sold
OneKey® MLS as distributed by MLS GRID #H6052324
07/27/2020$3,795,000PendingAgent Provided
07/16/2020$3,795,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax
Assessment$51,000
Home facts updated by county records

Comparable Sales for 77 Hillside Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
15 Hillside Rd, Rye, NY
0.15
Single-Family Home
$1,100,000
07/08/25
6
5
4,593
1 Polly Pk Road, RYE, NY
0.42
Single-Family Home
$2,100,000
09/26/25
5
5.5
5,789
472 Purchase Street, Rye, NY
0.70
Single-Family Home
$2,856,651
07/17/25
6
4.5
5,243
325 Highland Road, Rye, NY
0.61
Single-Family Home
$3,950,000
09/23/25
4
5
4,687
109 Grace Church St, Rye, NY
0.76
Single-Family Home
$4,995,000
08/22/25
5
6
5,800
6 Club Rd, Rye, NY
0.66
Single-Family Home
$3,500,000
06/09/25
4
4
3,502
14 Lakeside Drive, Rye, NY
0.57
Single-Family Home
$2,400,000
04/07/26
5
8
6,629
95 Dogwood Lane, Rye, NY
0.49
Single-Family Home
$2,702,000
12/08/25
5
2.5
2,949
96 Mendota Avenue, Rye, NY
0.31
Single-Family Home
$1,750,000
02/02/26
5
3.5
3,223
26 Mohawk Street, Rye, NY
0.32
Single-Family Home
$2,425,000
07/10/25
4
3.5
3,250

Nearby homes

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Assigned Schools

These are the assigned schools for 77 Hillside Rd.
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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
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  • 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
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77 Hillside Rd, Rye, NY 10580 is a 5 bedroom, 5 bathroom, 5,695 sqft single-family home built in 1884. This property is not currently available for sale. 77 Hillside Rd was last sold on Aug 15, 2020 for $3,800,000. The current Trulia Estimate for 77 Hillside Rd is $4,888,600.