Set on 1.04 level acres of beautifully landscaped property with vibrant perennial gardens and mature plantings, this impeccably renovated four-bedroom, three-and-a-half-bathroom Center Hall Colonial offers 4,199 square feet of thoughtfully designed living space in one of Chappaqua’s most sought-after neighborhoods. A gracious foyer with a classic sweeping staircase welcomes you into the home. Just off the entry, you’ll find a private office—perfect for working from home—as well as a stylish powder room. The expansive Great Room combines living and dining into one open, light-filled space, featuring a wood-burning fireplace and French doors that open to a large stone patio ideal for hosting family gatherings or enjoying tranquil afternoons outdoors. The sunny family room is perfect for everyday living, with its cozy fireplace, custom built-ins, and triple exposures overlooking the lush, level yard. Additionally, a discreet, retractable movie screen and projector descend at the touch of button, purpose built for shared family movie nights. The beautifully renovated dine-in kitchen is both warm and functional, with a walnut-topped island, casual dining area, stylish butler’s pantry and generous walk-in pantry. A charming garden room opens directly to the yard, providing another connection between indoor and outdoor spaces. The main level is completed by a play area, mudroom, and convenient laundry with double washers and dryers designed with busy households in mind. The attached two-car garage features an additional half bay for bikes, sports gear, or extra storage, with its own driveway access for added convenience. Upstairs, the tranquil primary suite is a retreat in itself, with custom built-ins, separate his and hers closets, and a luxurious spa bath. Two additional bedrooms and a full hall bath are accessed via the main staircase, while the fourth bedroom, another full bath, and a generous bonus/multipurpose room are reached by a second staircase or through Bedroom 3. The bonus space—perfect for a teen hangout, homework zone, or home gym—includes a balcony overlooking the parklike backyard. Located just minutes from the Chappaqua Swim and Tennis Club and only a seven-minute drive to the charming Village of Chappaqua—with its train station, shops, restaurants, library, and top-rated schools—this exceptional home blends timeless architecture, modern convenience, and family-friendly living in an unbeatable setting. A true Chappaqua gem!
Sold for $2,315,000 on 07/14/25
$2,315,000
55 Deepwood Drive, Chappaqua, NY 10514
4beds
4,199sqft
Single Family Residence, Residential
Built in 1927
1.04 Acres Lot
$2,316,700 Zestimate®
$551/sqft
$7,900 Estimated rent
What's special
Zillow last checked: 7 hours ago
Listing updated: July 14, 2025 at 12:38pm
Listed by:
Avital Soldatenko 914-329-6964,
Houlihan Lawrence Inc. 914-723-8877
Bought with:
Cindy Schwall, 10301200750
Houlihan Lawrence Inc.
Source: OneKey® MLS,MLS#: 851223

Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Other
- Description: Foyer, Pwr Rm, Office w/blt-ins, Main Stair, Great Rm w/WBF/Fr Doors to Patio, Fam Rm w/WBF/blt-ins/projector, Custom EIK w/ss appl/dining area, Butler's Pantry, Garden Rm, WIPantry, Back stair, Play Area/Mud Rm, 2 car Garage, Storage Rm
- Level: First
Other
- Description: Primary Suite w/blt-ins/His & Hers closets, Luxury Bath w/separate tub and shower, Linen CL, BR 2, Hall Bath, BR 3, CL for BR 3 in hall, CL, Back stair, Hall Bath, BR 4, Bonus/Multipurpose Rm with balcony overlooking yard
- Level: Second
Heating
- Oil, Steam
Cooling
- Central Air
Appliances
- Included: Dishwasher, Exhaust Fan, Freezer, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Oil Water Heater
Features
- Built-in Features, Chefs Kitchen, Crown Molding, Eat-in Kitchen, Entertainment Cabinets, Entrance Foyer, His and Hers Closets, Kitchen Island, Primary Bathroom, Original Details, Pantry, Recessed Lighting, Smart Thermostat, Soaking Tub, Speakers, Stone Counters, Storage
- Flooring: Hardwood
- Attic: Pull Stairs,Scuttle
- Number of fireplaces: 2
- Fireplace features: Wood Burning
Interior area
- Total structure area: 4,199
- Total interior livable area: 4,199 sqft
Property
Parking
- Total spaces: 2
- Parking features: Attached, Driveway
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Patio & porch: Patio
- Exterior features: Awning(s), Basketball Hoop, Mailbox, Playground
- Fencing: Electric
Lot
- Size: 1.04 Acres
Details
- Parcel number: 3600092017000010000034
- Special conditions: None
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence, Residential
Condition
- Year built: 1927
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: See Remarks
Community & neighborhood
Security
- Security features: Security System
Location
- Region: Chappaqua
Other
Other facts
- Listing agreement: Exclusive Right To Sell