169 Milton Road, Rye, NY 10580
OFF MARKET

$7,497,900

Trulia Estimate
  • 7 Beds
  • 6.5 Baths
  • 7,297 sqft (on 1 acre)

169 Milton Road, Rye, NY 10580

Est. Refi. Payment $50,196/mo*
Refinance Your Home
Currently Off Market - Sold Nov 13, 2025 for $6,995,000

Home Value

Trulia Estimate
$7.5M
Since last month
Increased$61K (+0.8%)
Since last year
Increased$411K (+5.8%)
Since last sale
Increased$516K (+7.4%)
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 +53% in the last 10 years
MonthEstimated value
2026
September 2026$7.51M
August 2026$7.45M
July 2026$7.37M
June 2026$7.28M
May 2026$7.21M
March 2026$7.18M
February 2026$7.06M
January 2026$7.09M
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
11 Billington Court, Rye, NY
0.04
Single-Family Home
$4,450,000
12/19/25
6
4.5
4,973
44 Grace Church Street, Rye, NY
0.49
Single-Family Home
$6,495,000
06/02/26
8
6
8,209
4 Martin Road, Rye, NY
0.45
Single-Family Home
$5,250,000
08/28/26
5
3.5
5,156
15 Davis Avenue, Rye, NY
0.57
Single-Family Home
$4,500,000
07/08/26
6
4.5
5,214
83 Orchard Avenue, Rye, NY
0.52
Single-Family Home
$3,395,000
09/15/26
5
5.5
5,400
4 Clark Lane, Rye, NY
0.35
Single-Family Home
$3,670,800
08/18/26
5
3.5
4,334
4 Boulder Road, Rye, NY
0.47
Single-Family Home
$3,751,000
06/18/26
5
4.5
4,820
81 Apawamis Avenue, Rye, NY
0.24
Single-Family Home
$3,750,000
08/11/26
4
2.5
2,800

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
11 Billington Court, Rye, NY 10580
0.04
$4,450,000
6
4.5
4,973
Recently Sold
211 Midland Avenue, Rye, NY 10580
0.13
$2,865,400
4
4
3,047
Off Market
1 Billington Court, Rye, NY 10580
0.13
$4,251,200
5
4.5
5,124
Off Market
2 Platt Lane, Rye, NY 10580
0.16
$3,560,200
5
4
4,214
Off Market
3 Lea Place, Rye, NY 10580
0.19
$2,795,000
4
3
3,034
For Sale
71 Apawamis Avenue, Rye, NY 10580
0.23
$2,943,800
4
2.5
2,597
Off Market
9 Hillcrest Lane, Rye, NY 10580
0.23
$2,682,700
4
3
2,628
Off Market
81 Apawamis Avenue, Rye, NY 10580
0.24
$3,750,000
4
2.5
2,800
Recently Sold
66 Milton Road #B-32, Rye, NY 10580
0.28
$422,200
1
1
700
Off Market
66 Milton Road #C21, Rye, NY 10580
0.28
$616,900
2
1
900
Off Market
66 Milton Road #J-41, Rye, NY 10580
0.28
$353,100
1
1
800
Off Market

Local Information

  • Map ViewExplore the area around 169 Milton Road.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1884
1 acre lot
7,297 sqft
$1,028/sqft
Garage

About this House

Welcome to 169 Milton Road, a once-in-a-lifetime opportunity to own one of Rye’s most iconic properties once known as the sea captain's house. This home offers an unparalleled lifestyle in a sought after, walk-to-all location. The elegant 7-bedroom home is set on a sprawling one-acre lot, offering both historical charm and modern sophistication. The property underwent a significant transformation in 2016 to create outdoor living space designed by renowned Sean Jancski Landscape Architects. The outdoor resort space features a stunning 20x44 swimming pool, a luxurious hot tub, and a meticulously designed entertainment area with two handsome fireplaces, a built-in BBQ, bar, and pergola. Enjoy the tranquil sound of fountains amid lush new plantings, all enhanced by state-of-the-art outdoor lighting and sound systems. In 2021, the original four-car garage was reimagined into a versatile two-car garage with an adjoining pool house. This sanctuary includes a lounge area with a built-in bar and fireplace, a full bath, and flexible space for fitness pursuits—perfect for retreating and relaxing in a resort-like setting and great for guest. Inside, the home exudes elegance with its high ceilings, built-in cabinetry, and beautifully scaled rooms, ideal for both grand entertaining and intimate gatherings. The sophisticated dining area features a charming fireplace, complemented by a butler's pantry for seamless hosting. The kitchen boasts modern upgrades while maintaining its classic appeal. Additional enhancements include new flooring throughout, updated bathrooms, and essential infrastructure upgrades such as new A/C units, a new boiler, and a new roof. The exterior has been refreshed with new paint, shutters, and shingles, ensuring this home is as striking outside as it is within.
This residence offers a harmonious blend of retreat and convenience, situated in the heart of Rye less than minutes to the vibrant, quaint town of Rye, schools and beach. Walk to all schools, nursery schools, town, train and beach.
169 Milton Road, Rye, NY 10580 is a 7 bedroom, 7 bathroom, 7,297 sqft single-family home built in 1884. It last sold for the $6,999,000 asking price on Nov 13, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $7,497,900.
Last check for updates: about 7 hours ago
Listed by Kimberly H. Arenas, (914) 262-6329
Compass Greater NY, LLC, (914) 353-5570
Bought with: Non Member-MLS, (000) 000-0000, Buyer Representation Office, (000) 000-0000
Source: OneKey® MLS as distributed by MLS GRID, MLS#821114

Home Details for 169 Milton Road

Interior Features

Interior Details
Basement: PartialNumber of Rooms: 14
Beds & Baths
Number of Bedrooms: 7Number of Bathrooms: 7Number of Bathrooms (full): 6Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 7297 Square Feet
Appliances & Utilities
Utilities: Natural Gas Connected, Sewer Connected, Trash Collection Public, Water ConnectedAppliances: Dishwasher, Dryer, Freezer, Oven, Refrigerator, Washer, Wine RefrigeratorDishwasherDryerRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,Hydro AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 5Has a FireplaceHas a Spa

Exterior Features

Exterior Home Features
Has a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageParking Spaces: 2Parking: Garage
Pool
Pool
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 5

Property Information

Year Built
Year Built: 1884
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Victorian
Building
Not Attached Property
Property Information
Parcel Number: 1400146015000010000009

Price & Status

Price
List Price: $6,999,000
Status Change & Dates
Off Market Date: Mon Apr 14 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: 7297 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 1 Acres

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: 821114Attic: PartialAttribution Contact: 914-353-5570Showing AttendedShowing Requirements: Appointment Only

Price and Tax history

DateEventPrice
Nov 13, 2025
Source: N/A
Sold
$6,995,000
May 19, 2025
Source: OneKey® MLS as distributed by MLS GRID #821114
Sold
$6,929,000
Apr 14, 2025
Source: OneKey® MLS as distributed by MLS GRID #821114
Pending
$6,999,000
Apr 9, 2025
Source: OneKey® MLS as distributed by MLS GRID #821114
Listed For Sale
$6,999,000
Aug 4, 2014
Source: OneKey® MLS as distributed by MLS GRID #H4401915
Sold
$4,840,000

Market trends in Rye

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.43M
$54.17KMoM
Sale-to-List Price
—
Price per sq ft
$774
$32MoM
Available listings
32
9MoM

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 2026-09-24 13:08:15 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 169 Milton Road

  • What is 169 Milton Road estimated to be worth?
    Trulia's estimated value for 169 Milton Road in Rye, NY is $7,497,900.
  • What is the price history for 169 Milton Road?
    169 Milton Road in Rye, NY last sold for $6,995,000 in November 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 $2.43M. That is up $54.17K from the prior month.
  • Does 169 Milton Road have air conditioning?
    Yes, 169 Milton Road in Rye, NY has air conditioning.
  • Does 169 Milton Road have a pool?
    Yes, 169 Milton Road in Rye, NY has a pool.

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