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!
Pending
$2,750,000
14 Lakeside Drive, Rye, NY 10580
5beds
6,629sqft
Single Family Residence, Residential
Built in 1984
1 Acres Lot
$-- Zestimate®
$415/sqft
$-- HOA
What's special
- 408 days |
- 132 |
- 0 |
Zillow last checked: 7 hours ago
Listing updated: November 24, 2025 at 11:01pm
Listing by:
Compass Greater NY, LLC 914-353-5570,
Michael P. McCooey 917-968-9737,
Elizabeth Higgins 617-571-9438,
Compass Greater NY, LLC
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 823716
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 9
- Full bathrooms: 7
- 1/2 bathrooms: 2
Other
- Description: Double Height Foyer, Living Room w/ Fireplace, Powder Room,Office, Family Room w/ Fireplace Overlooking Pool, Eat in Kitchen w/ Sliding Glass Doors to Patio, Master Bedroom w/ Dressing Room and Two Full Baths, Guest Room, Full Bath, Laundry
- Level: First
Other
- Description: Bedroom w/ Full Bath, Bedroom w/ Full Bath, Bedroom w/ Full Bath
- Level: Second
Other
- Description: Family Room w/ Fireplace, Excercise Room w/ Full Bath, Bar Room w/ Powder Room, Play Room, Storage, Door to Three Car Garage
- Level: Lower
Heating
- Forced Air
Cooling
- Central Air
Appliances
- Included: Dishwasher, Dryer, Freezer, Gas Cooktop, Refrigerator, Stainless Steel Appliance(s), Washer, Gas Water Heater
- Laundry: Washer/Dryer Hookup, Laundry Room
Features
- First Floor Bedroom, First Floor Full Bath, Breakfast Bar, Cathedral Ceiling(s), Central Vacuum, Eat-in Kitchen, Formal Dining, His and Hers Closets, In-Law Floorplan, Primary Bathroom, Master Downstairs, Open Floorplan, Pantry, Storage
- Windows: Floor to Ceiling Windows, Oversized Windows, Skylight(s), Wall of Windows
- Basement: Finished
- Attic: Pull Stairs
- Number of fireplaces: 3
- Fireplace features: Basement, Family Room, Living Room
Interior area
- Total structure area: 6,629
- Total interior livable area: 6,629 sqft
Property
Parking
- Total spaces: 3
- Parking features: Garage
- Garage spaces: 3
Features
- Levels: Three Or More
- Patio & porch: Patio
- Exterior features: Garden, Juliet Balcony
- Has private pool: Yes
- Pool features: Electric Heat, In Ground, Pool/Spa Combo
- Has spa: Yes
Lot
- Size: 1 Acres
Details
- Parcel number: 2801000545000000000096
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence, Residential
Materials
- Stucco
Condition
- Year built: 1984
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Electricity Connected, Natural Gas Connected
Community & HOA
HOA
- Has HOA: No
Location
- Region: Rye
Financial & listing details
- Price per square foot: $415/sqft
- Tax assessed value: $24,650
- Annual tax amount: $40,278
- Date on market: 2/14/2025
- Cumulative days on market: 403 days
- Listing agreement: Exclusive Right To Sell
- Exclusions: See remarks
- Electric utility on property: Yes
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 11/24/2025 | Pending sale | $2,750,000$415/sqft |
Source:  OneKey® MLS as distributed by MLS GRID #823716 Report a problem | ||
| 6/10/2025 | Price change | $2,750,000-6.8%$415/sqft |
Source: OneKey® MLS as distributed by MLS GRID #823716 Report a problem | ||
| 2/14/2025 | Listed for sale | $2,950,000$445/sqft |
Source: OneKey® MLS as distributed by MLS GRID #823716 Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $24,650 |
| 2023 | -- | $24,650 |
| 2022 | -- | $24,650 |
| 2021 | -- | $24,650 |
| 2020 | -- | $24,650 |
| 2019 | -- | $24,650 -9.4% |
| 2018 | -- | $27,200 |
| 2017 | -- | $27,200 -10.5% |
| 2016 | -- | $30,400 |
| 2015 | -- | $30,400 |
| 2014 | -- | $30,400 |
| 2013 | -- | $30,400 |
| 2012 | -- | $30,400 |
| 2011 | -- | $30,400 -21.5% |
| 2010 | -- | $38,750 |
| 2009 | -- | $38,750 |
| 2008 | -- | $38,750 -15.8% |
| 2007 | -- | $46,000 |
| 2006 | -- | $46,000 -10.2% |
| 2004 | -- | $51,210 |
| 2003 | -- | $51,210 |
| 2002 | -- | $51,210 |
| 2001 | -- | $51,210 |
| 2000 | -- | $51,210 |
| 1999 | -- | $51,210 |
Find assessor info on the county website
BuyAbility℠ payment
Estimated monthly payment
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Boost your down payment with 6% savings match
Earn up to a 6% match & get a competitive APY with a *. Zillow has partnered with to help get you home faster.
Learn more*Terms apply. Match provided by Foyer. Account offered by Pacific West Bank, Member FDIC.Climate risks
Neighborhood: 10580
Nearby schools
GreatSchools rating
- 7/10Purchase SchoolGrades: K-5Distance: 2.9 mi
- 7/10Louis M Klein Middle SchoolGrades: 6-8Distance: 2.2 mi
- 8/10Harrison High SchoolGrades: 9-12Distance: 2.9 mi
Schools provided by the listing agent
- Elementary: Purchase
- Middle: Louis M Klein Middle School
- High: Harrison High School
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Local experts in 10580
- New York
- Westchester County
- Rye
- 10580
- 14 Lakeside Drive
Nearby cities
Nearby zip codes
Other Rye Topics
