14 Lakeside Drive, Rye, NY 10580
SOLD
APR 7, 2026

14 Lakeside Drive
Rye, NY 10580

  • 5 Beds
  • 8 Baths
  • 6,629 sqft (on 1 acre)

$2,400,000

Last Sold: Apr 7, 2026
13% below list $2.75M
$362/sqft
Est. Refi. Payment $15,112/mo*
Refinance Your Home

$2,400,000

Last Sold: Apr 7, 2026
13% below list $2.75M
$362/sqft
Est. Refi. Payment $15,112/mo*
Refinance Your Home
5 Beds
8 Baths
6,629 sqft
(on 1 acre)

Local Information

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

Description

Located in Rye’s sought-after Flagler Estates neighborhood, 14 Lakeside Drive boasts an exceptional layout, first floor primary suite and resort-like pool, set on one full acre. Spanning almost 6,700 sq. ft., this stately colonial offers 5 bedrooms, 7 full bathrooms (2 half baths) and an open floor-plan that is perfectly suited for today’s buyer.

The first floor features a double height foyer, elegant formal entertaining rooms and a large family room with a fireplace overlooking the newly refinished pool and patio. The open kitchen is ideally located with access to the family room and formal dining room, and provides a large island, breakfast bar and informal dining area, with sliding doors leading out to the pool and patio.

The expansive first-floor primary suite has two large bathrooms, multiple walk-in closets and a dressing room, providing a private retreat. An additional in-law/au pair suite on the main level offers flexibility for guests or extended family, and a spacious home office is perfect for today’s “work from home” lifestyle.

The second floor provides three bedrooms (a second primary suite as well as two additional bedrooms) all with ample closet space and ensuite bathrooms.

The fully finished lower level includes a family room with a fireplace, an exercise room with a full bath, a bar room with dining area and a powder room, an enormous playroom, extensive storage, and an additional room with an ensuite full bathroom. The lower level also provides access to an attached three car garage.

For those seeking space, functionality, and a fantastic neighborhood, 14 Lakeside is not to be missed!
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 April 07, 2026

Home Highlights

Parking
Garage
Outdoor
Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
$362/sqft
Listed
180+ days ago

Home Details for 14 Lakeside Drive

Interior Features

Interior Details
Basement: FinishedNumber of Rooms: 15
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 9Number of Bathrooms (full): 7Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 6629 Square Feet
Appliances & Utilities
Utilities: Electricity Connected, Natural Gas ConnectedAppliances: Dishwasher, Dryer, Freezer, Gas Cooktop, Refrigerator, Stainless Steel Appliance(s), Washer, Gas Water HeaterDishwasherDryerLaundry: Washer/Dryer Hookup,Laundry RoomRefrigeratorWasher
Heating & Cooling
Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 3Fireplace: Basement, Family Room, Living RoomHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Floor to Ceiling Windows, Oversized Windows, Skylight(s), Wall of Windows
Levels, Entrance, & Accessibility
Levels: Three Or More

Exterior Features

Exterior Home Features
Patio / Porch: PatioExterior: Garden, Juliet BalconyGardenHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageParking Spaces: 3Parking: Garage
Pool
Pool: Electric Heat, In Ground, Pool/Spa ComboPool
Water & Sewer
Sewer: Public Sewer
Farm & Range
Not Allowed to Raise Horses

Days on Market

Cumulative Days on Market: 283

Property Information

Year Built
Year Built: 1984
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Colonial
Building
Construction Materials: StuccoNot Attached Property
Property Information
Not Included in Sale: See remarksParcel Number: 2801000545000000000096

Price & Status

Price
List Price: $2,750,000Price Per Sqft: $362/sqft
Status Change & Dates
Off Market Date: Mon Nov 24 2025

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: 6629 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: 823716Attic: Pull StairsAttribution Contact: 914-353-5570Showing Requirements: Appointment Only
Last check for updates: about 3 hours ago
Listed by Michael P. McCooey, (917) 968-9737
Compass Greater NY, LLC, (914) 353-5570
Elizabeth Higgins, (617) 571-9438
Compass Greater NY, LLC, (914) 353-5570
Bought with: Michael P. McCooey, (917) 968-9737, Compass Greater NY, LLC, (914) 353-5570
Co-Buyer's Agent: Elizabeth Higgins, (617) 571-9438, Compass Greater NY, LLC, (914) 353-5570
Source: OneKey® MLS as distributed by MLS GRID, MLS#823716

Price History for 14 Lakeside Drive

DatePriceEventSource
04/07/2026$2,400,000Sold
OneKey® MLS as distributed by MLS GRID #823716
11/24/2025$2,750,000PendingOneKey® MLS as distributed by MLS GRID #823716
06/10/2025$2,750,000PriceChange
OneKey® MLS as distributed by MLS GRID #823716
02/14/2025$2,950,000Listed For SaleOneKey® MLS as distributed by MLS GRID #823716

Market trends in Rye

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
47
12MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$25,750
Home facts updated by county records

Homeowner tools

Estimated monthly rent$7,973/mo
List your home for rent

Comparable Sales for 14 Lakeside Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
18 Lakeside Drive, Rye, NY
0.10
Single-Family Home
$3,450,000
05/29/26
5
4.5
4,612
1 Polly Pk Road, RYE, NY
0.49
Single-Family Home
$2,100,000
09/26/25
5
5.5
5,789
472 Purchase Street, Rye, NY
0.32
Single-Family Home
$2,856,651
07/17/25
6
4.5
5,243
8 Pheasant Drive, Rye, NY
0.24
Single-Family Home
$2,410,000
06/27/25
4
3
4,358
325 Highland Road, Rye, NY
0.37
Single-Family Home
$3,950,000
09/23/25
4
5
4,687
527 Purchase Street, Rye, NY
0.28
Single-Family Home
$2,050,000
06/03/26
4
4.5
3,895
526 Purchase Street, Rye, NY
0.32
Single-Family Home
$2,188,300
08/15/25
5
4.5
3,024
73 Park Drive S, Rye, NY
0.42
Single-Family Home
$7,200,000
11/10/25
6
7
8,585

Nearby homes

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Assigned Schools

These are the assigned schools for 14 Lakeside 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
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Off Market Homes Near 14 Lakeside 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
14 Lakeside Drive, Rye, NY 10580 is a 5 bedroom, 9 bathroom, 6,629 sqft single-family home built in 1984. This property is not currently available for sale. 14 Lakeside Drive was last sold on Apr 7, 2026 for $2,400,000 (13% lower than the asking price of $2,750,000). The current Trulia Estimate for 14 Lakeside Drive is $2,429,100.