5 Flagler Drive, Rye, NY 10580
OFF MARKET

5 Flagler Drive
Rye, NY 10580

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

$3,676,500

Trulia Estimate
as of Jun 10, 2026
Est. Refi. Payment $23,090/mo*
Refinance Your Home

$3,676,500

Trulia Estimate
as of Jun 10, 2026
Est. Refi. Payment $23,090/mo*
Refinance Your Home
5 Beds
7.5 Baths
6,339 sqft
(on 1.18 acres)

Local Information

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

Description

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,
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. This description is from December 07, 2024

Home Highlights

Parking
Open Parking
Outdoor
Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

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
Last check for updates: about 8 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

Price History for 5 Flagler Drive

DatePriceEventSource
08/23/2024$2,675,000Sold
OneKey® MLS as distributed by MLS GRID #H6309330
06/27/2024$2,750,000PendingOneKey® MLS as distributed by MLS GRID #H6309330
06/06/2024$2,750,000Listed For SaleOneKey® MLS as distributed by MLS GRID #H6309330

Market trends in Rye

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
59
14MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$24,000
Home facts updated by county records

Homeowner tools

Estimated monthly rent$17,316/mo
List your home for rent

Comparable Sales for 5 Flagler Drive

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
472 Purchase Street, Rye, NY
0.25
Single-Family Home
$2,856,651
07/17/25
6
4.5
5,243
8 Pheasant Drive, Rye, NY
0.32
Single-Family Home
$2,410,000
06/27/25
4
3
4,358
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
526 Purchase Street, Rye, NY
0.35
Single-Family Home
$2,188,300
08/15/25
5
4.5
3,024

Nearby homes

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Assigned Schools

These are the assigned schools for 5 Flagler Drive.
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
    Flag

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Off Market Homes Near 5 Flagler Drive

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Based on information submitted to the MLS GRID as of 2026-02-06 15:18:24 PST. 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
5 Flagler Drive, Rye, NY 10580 is a 5 bedroom, 8 bathroom, 6,339 sqft single-family home built in 1984. This property is not currently available for sale. 5 Flagler Drive was last sold on Aug 23, 2024 for $2,675,000 (3% lower than the asking price of $2,750,000). The current Trulia Estimate for 5 Flagler Drive is $3,676,500.