29 Highland Rd, Rye, NY 10580
OFF MARKET

29 Highland Rd
Rye, NY 10580

  • 5 Beds
  • 5 Baths
  • 4,458 sqft (on 0.66 acres)

$3,171,000

Trulia Estimate
as of Aug 1, 2026
Est. Refi. Payment $20,059/mo*
Refinance Your Home

$3,171,000

Trulia Estimate
as of Aug 1, 2026
Est. Refi. Payment $20,059/mo*
Refinance Your Home
5 Beds
5 Baths
4,458 sqft
(on 0.66 acres)

Local Information

  • Map ViewExplore the area around 29 Highland Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1939
Lot Size
0.66 acres
Living Area
4,458 sqft
Price/Sqft
$711
Parking
Garage

About this House

Walk though the door of this inviting, mint condition five bedroom, five bath English country home in Park Ridge, where elegance and comfort are in perfect harmony. Tucked in a private setting, yet so conveniently located just a short drive to downtown Rye and Harrison. Gracious formal rooms, beautiful gourmet kitchen and many recent updates including a new home office addition, make this home truly the best of all worlds. A must see t fully appreciate.
29 Highland Rd, Rye, NY 10580 is a 5 bedroom, 5 bathroom, 4,458 sqft single-family home built in 1939. It last sold for $2,100,000 on Jul 9, 2009. It is currently off market. The Trulia Estimate is $3,171,000, with a rent estimate of $17,034/month.

Home Details for 29 Highland Rd

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1939
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Wood
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.66 acres

Price History for 29 Highland Rd

DatePriceEventSource
07/09/2009$2,100,000Sold
N/A
03/02/2009$2,350,000PriceChange
Agent Provided
12/13/2008$2,450,000Listed For SaleAgent Provided

Market trends in Rye

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
41
6MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$34,200
Home facts updated by county records

Comparable Sales for 29 Highland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
9 Highland Rd, Rye, NY
0.17
Single-Family Home
$2,000,000
12/26/25
3
3.5
3,507
35 Seville Avenue, Rye, NY
0.27
Single-Family Home
$3,587,500
01/09/26
5
5.5
4,283
570 North Street, Harrison, NY
0.27
Single-Family Home
$2,812,500
10/20/25
6
6
4,824
205 Polly Pk Road, Rye, NY
0.45
Single-Family Home
$3,325,000
07/31/26
5
4.5
5,887
655 North Street, Rye, NY
0.36
Single-Family Home
$1,950,000
03/25/26
7
6
6,430
16 Seville Avenue, Rye, NY
0.42
Single-Family Home
$3,249,000
08/13/25
6
5
5,549
20 Devonshire Drive, White Plains, NY
0.62
Single-Family Home
$1,300,000
11/13/25
4
3.5
4,381
38 Stratford Road, Harrison, NY
0.57
Single-Family Home
$2,550,000
08/06/25
6
5.5
6,166
2 Park Drive S, Rye, NY
0.47
Single-Family Home
$4,250,000
06/22/26
6
7
6,719
455 Rosedale Avenue, White Plains, NY
0.80
Single-Family Home
$2,340,000
02/06/26
4
4.5
3,773

Nearby homes

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Assigned Schools

These are the assigned schools for 29 Highland Rd.
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
    Flag
  • Contessa1313
    "Best of all possible areas for schools, trains, buses, walking, bicyling, water sports, gardening,etc."
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 29 Highland Rd

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Off Market Homes Near 29 Highland Rd

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