Nestled in the heart of the coveted Lawrence Farms East neighborhood, 14 Annandale Road is a rare offering that seamlessly blends timeless sophistication with modern comfort on one of Chappaqua’s most desirable streets.
Set on beautifully manicured, park-like grounds, this classic four-bedroom residence exudes understated elegance from the moment you arrive. A gracious approach leads to a sun-drenched interior where refined millwork, wide-plank hardwood floors, and thoughtfully curated finishes create a warm yet elevated living experience.
Designed for both everyday living and effortless entertaining, the home features expansive formal and informal spaces, including a stunning living room with fireplace, an inviting great room with custom built-ins and a refined, custom bar, and a beautifully appointed chef’s kitchen featuring a Wolf range and separate Sub-Zero refrigerator and freezer, flowing seamlessly into bright dining areas. French doors open to an exceptional stone terrace—perfect for al fresco dining and gatherings—overlooking sweeping lawns and lush, mature landscaping.
Upstairs, the serene primary suite offers a private retreat with a spa-like bath and tranquil views, while three additional bedrooms provide comfort and versatility. A collection of flexible spaces—including a home office, bonus rooms, and lounge areas—allow for effortless adaptation to today’s lifestyle, whether for work, wellness, or recreation.
The grounds are equally impressive, offering expansive flat lawns, privacy, and room for play or future enhancements. Ideally located, the home is just a short walk to Chappaqua Crossing—home to Whole Foods, Life Time Fitness, and a variety of dining and lifestyle amenities—and minutes to downtown Chappaqua and Metro North.
A true blend of location, scale, and style—14 Annandale Road represents the very best of Lawrence Farms East living.
For sale
$2,599,000
14 Annandale Road, Chappaqua, NY 10514
4beds
3,523sqft
Single Family Residence, Residential
Built in 1939
1.3 Acres Lot
$-- Zestimate®
$738/sqft
$-- HOA
What's special
- 4 days |
- 1,617 |
- 93 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listing by:
Compass Greater NY, LLC 914-238-0676,
Sari J. Shaw 917-597-7394,
Christine Parke Anderson 214-929-6537,
Compass Greater NY, LLC
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 995181
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Heating
- Has Heating (Unspecified Type)
Cooling
- Central Air
Appliances
- Included: Dishwasher, Dryer, Freezer, Gas Cooktop, Gas Range, Microwave, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Gas Water Heater, Wine Refrigerator
- Laundry: Laundry Room
Features
- Beamed Ceilings, Breakfast Bar, Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Chandelier, Chefs Kitchen, Crown Molding, Double Vanity, Eat-in Kitchen, Entertainment Cabinets, Entrance Foyer, Formal Dining, High Speed Internet, His and Hers Closets, Kitchen Island, Marble Counters, Natural Woodwork, Open Floorplan, Open Kitchen, Original Details, Primary Bathroom, Recessed Lighting, Speakers, Storage, Walk Through Kitchen, Wired for Sound
- Flooring: Hardwood
- Basement: Full
- Attic: Pull Stairs
- Number of fireplaces: 2
- Fireplace features: Wood Burning
Interior area
- Total structure area: 3,523
- Total interior livable area: 3,523 sqft
Video & virtual tour
Property
Parking
- Total spaces: 3
- Parking features: Detached
- Garage spaces: 3
Features
- Patio & porch: Patio
- Exterior features: Basketball Hoop, Fire Pit, Garden, Gas Grill, Lighting, Rain Gutters
Lot
- Size: 1.3 Acres
- Features: Back Yard, Front Yard, Garden, Landscaped, Level, Near School, Near Shops
Details
- Parcel number: 3600093009000020000018
- Special conditions: None
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence, Residential
Materials
- Wood Siding
Condition
- Year built: 1939
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Cable Connected, Electricity Connected, Natural Gas Connected, Phone Connected, Propane, Trash Collection Public, Water Connected
Community & HOA
Community
- Security: Security System
HOA
- Has HOA: No
Location
- Region: Chappaqua
Financial & listing details
- Price per square foot: $738/sqft
- Tax assessed value: $241,750
- Annual tax amount: $40,423
- Date on market: 5/8/2026
- Listing agreement: Exclusive Right To Sell
- Exclusions: selected light fixtures
- Electric utility on property: Yes
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/8/2026 | Listed for sale | $2,599,000+66.1%$738/sqft |
Source:  OneKey® MLS as distributed by MLS GRID #995181 Report a problem | ||
| 6/1/2006 | Sold | $1,565,000+106.6%$444/sqft |
Source: Public Record Report a problem | ||
| 6/24/1996 | Sold | $757,500$215/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $241,750 |
| 2024 | -- | $241,750 |
| 2023 | -- | $241,750 |
| 2022 | -- | $241,750 |
| 2021 | -- | $241,750 |
| 2020 | -- | $241,750 |
| 2019 | -- | $241,750 |
| 2018 | -- | $241,750 |
| 2017 | -- | $241,750 +1.7% |
| 2016 | -- | $237,745 |
| 2015 | -- | $237,745 |
| 2014 | -- | $237,745 |
| 2013 | -- | $237,745 +13.2% |
| 2012 | -- | $210,000 +3.4% |
| 2011 | -- | $203,100 |
| 2010 | -- | $203,100 |
| 2009 | -- | $203,100 |
| 2008 | -- | $203,100 |
| 2007 | -- | $203,100 |
| 2006 | -- | $203,100 |
| 2005 | -- | $203,100 |
| 2004 | -- | $203,100 |
| 2003 | -- | $203,100 |
| 2002 | -- | $203,100 |
| 2001 | -- | $203,100 |
| 2000 | -- | $203,100 |
| 1999 | -- | $203,100 |
Find assessor info on the county website
Monthly 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.
Climate risks
Neighborhood: 10514
Nearby schools
GreatSchools rating
- 8/10Roaring Brook SchoolGrades: K-4Distance: 1.6 mi
- 8/10Robert E Bell SchoolGrades: 5-8Distance: 1.9 mi
- 10/10Horace Greeley High SchoolGrades: 9-12Distance: 0.4 mi
Schools provided by the listing agent
- Elementary: Douglas G Grafflin School
- Middle: Robert E Bell School
- High: Horace Greeley 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.
A local agent can set up tours, give advice and negotiate with sellers.
- New York
- Westchester County
- Chappaqua
- 10514
- 14 Annandale Road
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