369 Sleepy Hollow Rd

Briarcliff Manor, NY 10510

$2,150,000
Last Sold Price
5
Beds
3,981 Sq. Ft.
$540 / Sq. Ft.
3,981
Sq. Ft.
$540
per Sq. Ft.
Closed 11/7/25
Closed 11/7/25

Description

Like a masterly crafted engaging jewel this grand 1927 Colonial farmhouse reveals delightful surprises at every turn. After nearly a century of stately gracious living the property has been luxuriously updated for the 21st century while preserving its timeless charm and refined architectural details. Whether hosting holiday gatherings, summer soirees or more intimate moments this sumptuous Colonial transforms every day into a special occasion. The heart of the house features an enormous gourmet kitchen...Like a masterly crafted engaging jewel this grand 1927 Colonial farmhouse reveals delightful surprises at every turn. After nearly a century of stately gracious living the property has been luxuriously updated for the 21st century while preserving its timeless charm and refined architectural details. Whether hosting holiday gatherings, summer soirees or more intimate moments this sumptuous Colonial transforms every day into a special occasion. The heart of the house features an enormous gourmet kitchen designed with space for everyone to gather. Stunning from top to bottom with tin ceiling, Venetian tile flooring, reclaimed barn wood center island and top-shelf appliances from Wolf, Sub-Zero and Bosch. A traditional front-corner dining room accommodates a more formal setting. The front-facing living room with built-ins adjoins a spectacular wood-paneled screened porch with soaring beamed ceiling, ceiling fan, massive stone fireplace and beautiful stone flooring creating a perfect three-season retreat. The inviting family room picture window with sidelights and built-in window bench captures warm afternoon light. French pocket doors separate the formal front rooms from the entry hall with its wide straight staircase ascending to the upper levels. Like a sanctuary perched above it all the sumptuous primary suite begins with a two-story windowed entry with French door to a private balcony. The loft-like sleeping chamber warmed by a cozy gas fireplace, glows with golden afternoon and soft sunset light. A dedicated dressing room houses stacked LG washer/dryer, while the spa-like ensuite bath boasts a standalone clawfoot soaking tub and steam shower with bench, in-wall jets and a handheld. Two comfortable upstairs bedrooms share an updated hall bath. A third upstairs bedroom enjoys its own dressing room and a private ensuite bath featuring a steam shower. One main-level bedroom accesses the main-level full bath. A welcoming main-level mudroom with beamed ceiling and clerestory windows offers lockers, benches, a wash basin plus built-ins for pets. Amusements continue downstairs in an entertaining stone-lined game room with comfortable lounge area, set atop radiant-heated Venetian stone tiling. A private wine cellar adjoins for the perfect pairing. Additional lower-level amenities include a home office with convenient door to the motor court, an exercise room/dance studio with mirrored wall, full bath with shower and a complete laundry room featuring Miele washer and dryer. The resort-style outdoor living spaces showcase a movie-star worthy in-ground gunite pool with electronic cover, diving board, waterfall, and elegant bluestone coping surrounded by stone decking. A separate spa for ultimate relaxation and rejuvenation is smartly positioned just outside the uber cool pool house featuring French door entry, round clerestory window, soaring wood-paneled ceiling with recessed lighting and fan, a striking stone accent wall with in-laid wood-burning fireplace, stone flooring, half bath and outdoor shower. Cater to a crowd from the separate deluxe summer kitchen cabana outfitted with full-size refrigerator, Bosch dishwasher, stainless steel sink, Sub-Zero wine fridge, built-in ice maker and glass-front display cabinetry and an outdoor Wolf gas grill with separate burner set in a stone countertop. Swing away lazy afternoons with cool drinks in hand, listening to music from the indoor/outdoor audio system on the grand stately front porch. Sway through the stunning, professionally landscaped grounds with mature and established landscaping, specimen plantings and thoughtful stone pathways creating a park-like setting enhanced by exterior landscape lighting and a patriotic flagpole. Other notable characteristics include a stone lined bocce court, an automatic backup generator, perimeter fencing and a 2-car detached garage with electric heater and attic storage fronted by a gated, cobblestone motor court. One-of-a-kind.
  1. Listed by Stacy Levey • William Raveis-New York, LLC
    P: (914)-238-0505 C: (914)-400-3962 stacy.levey@raveis.com
  2. Listed by Jan Pierre Chavez • Coldwell Banker Realty
    P: (914)-967-0059 C: (914)-815-4718 jp.chavez@cbrealty.com

Property Details for 369 Sleepy Hollow Road

City/Township
Ossining
Architectural Style
Colonial, Farmhouse
Garage Spaces
2.00
Waterfront
No
Section Area
Long Hill Rd
LISTING UPDATED: 11/07/2025 04:00 PM

Property Details for 369 Sleepy Hollow Road

StatusClosed
MLS #904715
Days on Market13
Taxes$48,671 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family
Year Built1927
Lot Size1.05 AC / 45,738 SF
CountyWestchester County

Location

Add your commute

Building Information for 369 Sleepy Hollow Road

Stories-Year Built1927Building Size-Lot Size1.05 AC / 45,738 SF

Payment Calculator

$14,680 per month

30 year fixed, 6.28% Interest

Principal and Interest

$10,624

Property Taxes

$4,056

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 369 Sleepy Hollow Road

Summary
Location and General Information
  • Senior Community YN: No
  • Property Attached: No
  • Structure Type: false
  • Levels: Three Or More
  • Property Condition: Actual
  • State Or Province: NY
  • Water Access YN: No
School Information
  • School District: Briarcliff Manor
  • Elementary School District: Briarcliff Manor
  • Elementary School: Todd Elementary School
  • Middle Or Junior School District: Briarcliff Manor
  • Middle Or Junior School: Briarcliff Middle School
  • High School District: Briarcliff Manor
  • High School: Briarcliff High School
Rental
Rental
  • Lease Considered: No
Unit Information
Unit Information
  • Building Units Total: 1
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 4201-105-006-00000-000-0017-000-0-1
  • Additional Fees: No
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, Balcony, Beamed Ceilings, Bedroom, Built-in Features, Cabana, Ceiling Fan(s), Chefs Kitchen, Colonial, Covered, Crown Molding, Diving Board, Eat in Kitchen, Entrance Foyer, Farmhouse, Fenced, Fire Sprinkler System, First Floor Full Bath, Formal Dining, Full, Garage(s), Garden, Gas, Hardwood Floors As Seen, High Speed Internet, In Basement, In Ground, Kitchen Island, Lighting, Living Room, Multiple Locations, Natural Woodwork, Original Details, Outdoor Kitchen, Outdoor Pool, Oversized Windows, Patio, Pool Cover, Pool House, Porch, Primary Bathroom, Public, Recessed Lighting, Screened, Security Lights, Security System, Shutters, Smart Thermostat, Smoke Detector(s), Soaking Tub, Sound System, Speakers, Stone Counters, Terrace, Tile, Video Cameras, Walk In Closet, Well, Wet Bar, Wired for Sound, Wood Burning
  • Interior Features: First Floor Bedroom, First Floor Full Bath, Beamed Ceilings, Built-in Features, Ceiling Fan(s), Chefs Kitchen, Crown Molding, Eat-in Kitchen, Entrance Foyer, Formal Dining, High Speed Internet, Kitchen Island, Natural Woodwork, Original Details, Primary Bathroom, Recessed Lighting, Smart Thermostat, Soaking Tub, Sound System, Speakers, Stone Counters, Walk-In Closet(s), Wet Bar, Wired for Sound
  • Appliances: Convection Oven, Dishwasher, Dryer, Exhaust Fan, Freezer, Gas Cooktop, Microwave, Refrigerator, Washer, Indirect Water Heater, Wine Refrigerator
  • Total Rooms: 12
  • Basement: Finished, Full, Walk-Out Access
  • Attic Description: None
  • Fireplace: Yes
  • Fireplaces Total: 4
  • Fireplace Features: Bedroom, Gas, Living Room, Wood Burning
  • Location Amenities: Walk Out Basement, Exposure West, Balcony, Fenced, Fenced Yard, Hardwood Floors As Seen, 1st Fl Master Bedroom, Chef's Kitchen, Eat in Kitchen, Entry Foyer, Foyer, Formal Dining Room, High Speed Internet, Island Kitchen, Original Details, Soacking Tub, Walk In Closet, Wetbar, Garden, Brownstone, Patio, Porch, Terrace, In Ground Pool, Pool Outdoor, Security System, Oversized Windows
  • Laundry Features: In Basement, Multiple Locations
  • Security Features: Fire Sprinkler System,Security Lights,Security System,Smoke Detector(s),Video Cameras
  • Spa: Yes
  • Window Features: Oversized Windows,Shutters
  • Flooring: Hardwood, Tile
  • Exclusions: Dining Room Chandelier, SONOS equipment, TVs.
  • Living Area: 3,981.00
  • Foundation Details: Stone
  • Basement: Yes
Exterior Features
  • Exterior Features: Balcony, Garden, Lighting, Speakers
  • Exterior Property Features: Balcony, Garden, Lighting, Speakers, Diving Board, In Ground, Outdoor Pool, Pool Cover, Covered, Patio, Porch, Screened, Terrace, Fenced, Full, Oversized Windows, Shutters, Back Yard, Corner Lot, Front Yard, Landscaped, Level, Near Golf Course, Sprinklers In Front, Sprinklers In Rear, Stone/Brick Wall
  • Elevation Certificate: No
  • Fencing: Fenced,Full
  • Patio And Porch Features: Covered,Patio,Porch,Screened,Terrace
  • Construction Materials: Frame
  • Road Frontage Type: Municipal
  • Road Responsibility: Public Maintained Road
  • Other Structures: Cabana,Garage(s),Outdoor Kitchen,Pool House
  • Horse: No
  • Pool Private: Yes
  • Pool Features: Diving Board,In Ground,Outdoor Pool,Pool Cover
  • Pool Details: Diving Board,In Ground,Outdoor Pool,Pool Cover
  • Direction Faces: West
Lot Information
  • Lot Features: Back Yard, Corner Lot, Front Yard, Garden, Landscaped, Level, Near Golf Course, Sprinklers In Front, Sprinklers In Rear, Stone/Brick Wall
  • Additional Parcel: No
  • Site Features: Back Yard, Corner Lot, Front Yard, Garden, Landscaped, Level, Near Golf Course, Sprinklers In Front, Sprinklers In Rear, Stone/Brick Wall
  • Building Area Units: Square Feet
Parking
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: Central Air
  • Heating: Hot Air, Natural Gas, Radiant, Radiant Floor
  • Heat Fuel Type: Hot Air, Natural Gas, Radiant, Radiant Floor
  • Sewer: Public Sewer
  • Water Source: Well, Public
  • Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Phone Connected, Sewer Connected, Trash Collection Public, Water Connected
Green Features
  • Green Features: Oversized Windows, Shutters, Convection Oven, Dishwasher, Dryer, Exhaust Fan, Freezer, Gas Cooktop, Microwave, Refrigerator, Washer, Indirect Water Heater, Wine Refrigerator, Hot Air, Natural Gas, Radiant, Radiant Floor, Balcony, Garden, Lighting, Speakers, Diving Board, In Ground, Outdoor Pool, Pool Cover
Agent
Payment and Rate
  • Down Payment Resource: No

Property History for 369 Sleepy Hollow Road

DateEvent & SourcePriceAppreciation
Nov 7, 2025

Sold (Public Record)

Public Record #1919797857

$2,150,000

+6.3% / yr

Oct 7, 2021

Sold (Public Record)

Public Record #1500190938

$1,675,000—
DateEvent & SourcePrice
11/07/2025

Sold (Public Record)

Public Record #1919797857

$2,150,000

+6.3% / yr

10/07/2021

Sold (Public Record)

Public Record #1500190938

$1,675,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 369 Sleepy Hollow Road

Taxable ValueLand$447,100Additions$1,279,800Total$1,726,900
Tax Record2020$42,518 ($3,543 / month)
Home Facts
Beds4Baths2.5Total Finished SqFt3,006 SqFtAbove Grade Finished SqFt3,006 SqFtStories3Lot Size45,738 SqFtStyleSingle Family ResidenceYear Built1927CountyWESTCHESTERAPN554201 105.06-1-17Fireplace TypeHas Fireplace

Schools near 369 Sleepy Hollow Road

This home is within Briarcliff Manor Union Free School District.
Rating
School
Type
Grades
Distance
Todd Elementary School
Public - K to 5
Briarcliff Middle School
Public - 6 to 8
Briarcliff High School
Public - 9 to 12
Rating
School
Distance
Todd Elementary School
PublicK to 5

Briarcliff Middle School
Public6 to 8

Briarcliff High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Listing Courtesy of William Raveis-New York, LLC; Coldwell Banker Realty

Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 12/27/2025 05:38 AM. All data is obtained from various sources and may not have been verified by broker orMLS GRID. Supplied Open House Information is subject to change without notice. All informationshould be independently reviewed and verified for accuracy. Properties may or may not be listed bythe office/agent presenting the information.