20 Hillside Rd, Rye, NY 10580
OFF MARKET

20 Hillside Rd
Rye, NY 10580

  • 8 Beds
  • 2 Baths
  • 3,898 sqft (on 0.41 acres)

$1,737,300

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $11,105/mo*
Refinance Your Home

$1,737,300

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $11,105/mo*
Refinance Your Home
8 Beds
2 Baths
3,898 sqft
(on 0.41 acres)

Home Value

Trulia Estimate
$1.74M
Since last month
Increased$44K (+2.6%)
Since last year
Decreased$22K (-1.2%)
Since last sale
Increased$2M (+674.4%)
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 +23% in the last 10 years
MonthEstimated value
2026
August 2026$1.74M
July 2026$1.76M
June 2026$1.7M
May 2026$1.63M
April 2026$1.61M
March 2026$2.25M
February 2026$2.08M
January 2026$2.13M
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
236 Purchase St, Rye, NY
0.12
Multi-Family Home
$1,630,000
03/30/26
5
3
3,307
96 Inwood Avenue, Port Chester, NY
0.51
Multi-Family Home
$875,000
07/23/26
5
2
3,445
260 Purchase St, Rye, NY
0.06
Multi-Family Home
$850,000
12/22/25
2
1
1,797
27 Westview Avenue, Rye Brook, NY
0.67
Multi-Family Home
$990,000
06/23/26
5
2
3,374
97 Inwood Avenue, Port Chester, NY
0.53
Multi-Family Home
$950,000
08/29/25
6
3
3,780
130 Spring Street, Port Chester, NY
0.79
Multi-Family Home
$1,045,000
04/24/26
6
2
3,648
244 SOUTH RIDGE Street, Port Chester, NY
0.61
Multi-Family Home
$960,000
12/24/25
6
3
2,925
72 Orchard Avenue, Rye, NY
0.77
Multi-Family Home
$1,150,000
08/20/25
5
2
2,634
19 Westview Avenue, Rye Brook, NY
0.56
Multi-Family Home
$925,000
09/19/25
5
4
2,419
33 Alto Avenue, Port Chester, NY
1.02
Multi-Family Home
$950,000
12/02/25
4
2
3,631

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
17 Hillside Road, Rye, NY 10580
0.05
$4,213,600
6
5.5
5,315
Off Market
145 Wappanocca Avenue, Rye, NY 10580
0.09
$3,543,700
5
5
4,345
Off Market
55 Hillside Road, Rye, NY 10580
0.10
$4,766,100
6
5.5
4,834
Off Market
335 Purchase Street, Rye, NY 10580
0.12
$4,094,500
6
4.5
5,038
Off Market
55 Meadow Place, Rye, NY 10580
0.12
$2,135,900
6
3.5
2,308
Off Market
10 Evergreen Avenue, Rye, NY 10580
0.11
$3,900,400
5
5.5
4,642
Off Market
106 Wappanocca Avenue, Rye, NY 10580
0.12
$1,485,800
3
2
1,596
Off Market
48 Meadow Place, Rye, NY 10580
0.14
$1,908,400
4
2.5
1,903
Off Market
61 Grandview Avenue, Rye, NY 10580
0.14
$3,970,000
5
4.5
4,738
Off Market
94 Wappanocca Avenue, Rye, NY 10580
0.15
$1,957,500
4
2.5
2,947
Off Market
19 Highland Park Place, Rye, NY 10580
0.15
$2,222,300
4
2.5
2,746
Off Market
50 Ridge Street, Rye, NY 10580
0.15
$6,464,600
7
7.5
8,231
Off Market

Local Information

  • Map ViewExplore the area around 20 Hillside Rd.
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Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1980
Lot Size
0.41 acres
Living Area
3,898 sqft
Price/Sqft
$446

About this House

This multi-family home is located at 20 Hillside Rd, Rye, NY. 20 Hillside Rd is in Rye, NY and in ZIP code 10580. This property has 8 bedrooms, 2 bathrooms and approximately 3,898 sqft of floor space. This property has a lot size of 0.41 acres and was built in 1980.
20 Hillside Rd, Rye, NY 10580 is a 8 bedroom, 2 bathroom, 3,898 sqft multi-family built in 1980. It last sold for $225,000 on Apr 14, 1997. It is currently off market. The Trulia Estimate is $1,737,300, with a rent estimate of $3,660/month.

Home Details for 20 Hillside Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1980
Property Type / Style
Property Type: Multi FamilyArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Wood

Community

Units in Building: 2

Lot Information

Lot Area: 0.41 acres

Price and Tax history

DateEventPrice
Apr 14, 1997
Source: N/A
Sold
$225,000
Jan 19, 1995
Source: N/A
Sold
$50,000

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
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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
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Off Market Homes Near 20 Hillside Rd

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Frequently asked questions about 20 Hillside Rd

  • What is 20 Hillside Rd estimated to be worth?
    Trulia's estimated value for 20 Hillside Rd in Rye, NY is $1,737,300.
  • What is the price history for 20 Hillside Rd?
    20 Hillside Rd in Rye, NY last sold for $225,000 in April 1997.
  • 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.