5 Flagler Drive, Rye, NY 10580
OFF MARKET

$3,676,900

Trulia Estimate
  • 5 Beds
  • 7.5 Baths
  • 6,339 sqft (on 1.18 acres)

5 Flagler Drive, Rye, NY 10580

Est. Refi. Payment $23,847/mo*
Refinance Your Home
Currently Off Market - Sold Aug 23, 2024 for $2,675,000

Home Value

Trulia Estimate
$3.68M
Since last month
Decreased$7K (-0.2%)
Since last year
Increased$475K (+14.8%)
Since last sale
Increased$1M (+37.5%)
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 +21% in the last 10 years
MonthEstimated value
2026
August 2026$3.68M
August 2026$3.67M
July 2026$3.68M
June 2026$3.65M
May 2026$3.61M
April 2026$3.41M
March 2026$3.43M
February 2026$3.45M
January 2026$3.4M
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
14 Lakeside Drive, Rye, NY
0.22
Single-Family Home
$2,400,000
04/07/26
5
8
6,629
1 Polly Pk Road, RYE, NY
0.27
Single-Family Home
$2,100,000
09/26/25
5
5.5
5,789
18 Lakeside Drive, Rye, NY
0.18
Single-Family Home
$3,450,000
05/29/26
5
4.5
4,612
325 Highland Road, Rye, NY
0.21
Single-Family Home
$3,950,000
09/23/25
4
5
4,687
73 Park Drive S, Rye, NY
0.40
Single-Family Home
$7,200,000
11/10/25
6
7
8,585
527 Purchase Street, Rye, NY
0.33
Single-Family Home
$2,050,000
06/03/26
4
4.5
3,895
95 Dogwood Lane, Rye, NY
0.43
Single-Family Home
$2,702,000
12/08/25
5
2.5
2,949
1 Oneida Street, Rye, NY
0.46
Single-Family Home
$2,906,024
06/15/26
4
4.5
3,608

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
7 Stonegate Lane, Rye, NY 10580
0.13
$3,468,300
4
5.5
6,069
Off Market
18 Lakeside Drive, Rye, NY 10580
0.18
$3,450,000
5
4.5
4,612
Recently Sold
14 Lakeside Drive, Rye, NY 10580
0.22
$2,400,000
5
8
6,629
Recently Sold
58 BROOKRIDGE Court, Rye Brook, NY 10573
0.24
$980,400
3
2.5
1,896
Off Market
3 Highland Ridge Lane, Rye, NY 10580
0.22
$1,921,200
3
2.5
2,177
Off Market
325 Highland Road, Rye, NY 10580
0.21
$4,244,500
4
5
4,687
Off Market
33 Mount Holly Drive, Rye, NY 10580
0.23
$3,472,600
5
4.5
5,178
Off Market
335 Purchase Street, Rye, NY 10580
0.26
$4,069,300
6
4.5
5,038
Off Market
27 Brookridge Court, Rye Brook, NY 10573
0.27
$830,600
2
2.5
1,892
Off Market
25 Brookridge Court, Rye Brook, NY 10573
0.27
$837,300
2
2.5
1,692
Off Market
233 Highland Road, Rye, NY 10580
0.24
$3,295,000
6
5.5
5,725
For Sale

Local Information

  • Map ViewExplore the area around 5 Flagler Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1984
1.18 acre lot
6,339 sqft
$580/sqft
Open Parking

About this House

Prepare to be enchanted by this extraordinary 6339 sq ft Contemporary Colonial Flagler Estates Manor with a heated free-form Shoreline pool! Designed to blend the elegant traditionalism of a French Country Chateau with the best of striking modern interior luxury style, this breathtaking home is one-of-a-kind. Set on a gorgeous 1.18 acre property replete with lush specimen trees and perennial landscaping, the majestic exterior of this gracious residence is anchored by the grand cobbled brick forecourt and gardens, continuing up the stone steps to the covered front portico and entryway. Step into the dramatic skylit double-height Entry Foyer and enjoy the direct sightlines through to the spectacular Great Room with its soaring cathedral ceiling, 2-story stone fireplace and 2 dramatic walls of windows overlooking the rear patio, garden and pool. The light and airy interiors were designed to maximize modern open-plan living with generous proportions and intelligent layout, ideal for providing fantastic interior space for large-scale parties and entertaining! The oversized Chef’s kitchen features a large island and bright Breakfast Room overlooking the pool and patio. Adjacent is the Formal Dining Room and the cozy Family Room/Library with walls of built-ins, wood-burning fireplace and sliding glass doors to outside. The serene Primary Suite is conveniently situated on the first floor in its own private wing with attached Sitting Room w. fireplace and wetbar, plus His Primary Bathroom with Walk-in Closet and a separate Hers Primary Bathroom with Walk-in Closet. Additional First Floor amenities include a First Floor Bedroom/Study with ensuite Bathroom, a Powder Room and Laundry. The grand staircase leading to the The 2nd floor features an airy walkway overlooking the Entry Foyer and Great Room, 3 light and bright upper Bedrooms, each with ensuite Bathroom, 2 with fireplaces, and striking views over the front and rear gardens. The finished Basement offers so much fabulous useable space: currently there is a Playroom/Rec Room, Lounge/Gaming area, Movie Theater, Full Bathroom, Wine Room, cedar closet, multiple large storage/utility rooms, and access to the spacious attached 3-car garage. The rear property offers a magnificent oasis of privacy and tranquility with a beautiful free-form Shoreline pool and hot tub set in a stone & brick patio with built-in barbeque, multiple shaded seating areas and upper lawn area – perfect for endless summers entertaining family and friends with glorious pool parties, BBQs, proms and engagements, sports and outdoor fun. This private yet accessible location offers easy access to the fabulous restaurants, shopping and amenities of downtown Rye, Harrison & Greenwich, just steps from Westchester Country Club and an easy drive to all the magnificent clubs, beaches and parks of the Long Island Sound, and all just a quick 35 minutes by train from Manhattan. (Note: photos with furniture are virtually staged). Additional Information: Amenities:Dressing Area,Marble Bath,Steam Shower,ParkingFeatures:3 Car Attached,
5 Flagler Drive, Rye, NY 10580 is a 5 bedroom, 8 bathroom, 6,339 sqft single-family home built in 1984. It last sold for $2,675,000 on Aug 23, 2024 (3% below the $2,750,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,676,900.
Last check for updates: about 5 hours ago
Listed by Fiona M. Dogan, (914) 414-5147
Julia B Fee Sothebys Int. Rlty, (914) 967-4600
Caroline Howard, (914) 806-0331
Julia B Fee Sothebys Int. Rlty, (914) 967-4600
Bought with: Francine Klingenstein, (914) 772-4203, Julia B Fee Sothebys Int. Rlty, (914) 967-4600
Source: OneKey® MLS as distributed by MLS GRID, MLS#H6309330

Home Details for 5 Flagler Drive

Interior Features

Interior Details
Basement: Finished,Full,Walk-Out AccessNumber of Rooms: 9
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 8Number of Bathrooms (full): 7Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 6339 Square Feet
Appliances & Utilities
Utilities: Trash Collection PublicAppliances: Tankless Water Heater
Heating & Cooling
Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 5Has a Fireplace
Windows, Doors, Floors & Walls
Window: Floor to Ceiling Windows, Oversized Windows, Skylight(s), Wall of WindowsFlooring: Hardwood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Hardwood
Security
Security: Security System

Exterior Features

Exterior Home Features
Patio / Porch: PatioExterior: Courtyard
Parking & Garage
No CarportHas Open ParkingParking Spaces: 3Parking: Attached,Driveway
Pool
Pool: In GroundPool
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 1984Year Renovated: 2024
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Colonial,Contemporary,Estate
Building
Construction Materials: BrickNot Attached Property
Property Information
Condition: ActualParcel Number: 2801000545000000000061

Price & Status

Price
List Price: $2,750,000
Status Change & Dates
Off Market Date: Thu Jun 27 2024

Active Status

MLS Status: Sold

Location

Direction & Address
City: Rye
School Information
Elementary School: PurchaseJr High / Middle School: Louis M Klein Middle SchoolHigh School: Harrison High SchoolHigh School District: Harrison

Building

Building Area
Building Area: 6339 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 1.18 Acres

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: H6309330Attic: Partially Finished, PartialAttribution Contact: (914) 967-4600Showing Requirements: Lockbox

Price and Tax history

DateEventPrice
Aug 23, 2024
Source: OneKey® MLS as distributed by MLS GRID #H6309330
Sold
$2,675,000
Jun 27, 2024
Source: OneKey® MLS as distributed by MLS GRID #H6309330
Pending
$2,750,000
Jun 6, 2024
Source: OneKey® MLS as distributed by MLS GRID #H6309330
Listed For Sale
$2,750,000

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

Based on information submitted to the MLS GRID as of 2026-09-10 14:38:06 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 5 Flagler Drive

  • What is 5 Flagler Drive estimated to be worth?
    Trulia's estimated value for 5 Flagler Drive in Rye, NY is $3,676,900.
  • What is the price history for 5 Flagler Drive?
    5 Flagler Drive in Rye, NY last sold for $2,675,000 in August 2024.
  • 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.
  • Does 5 Flagler Drive have air conditioning?
    Yes, 5 Flagler Drive in Rye, NY has air conditioning.
  • Does 5 Flagler Drive have a pool?
    Yes, 5 Flagler Drive in Rye, NY has a pool.

Explore by feature - Pet Friendly

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Off Market Homes Near 5 Flagler Drive

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