45, Wolden Road, Village of Ossining, Town of Ossining, Westchester County, New York, 10562, United States
Perched majestically on nearly two private acres in Westchester County’s most prestigious enclave, the Westchester Castle Tudor Estate represents the pinnacle of New York suburban luxury. This extraordinary 7,000-square-foot residence, dating to 1928, stands as a testament to the golden age of American estate architecture while offering every modern amenity discerning travelers expect. Just 35 minutes from Manhattan yet worlds away from urban chaos, this remarkable property provides an unparalleled setting for those seeking privacy, grandeur, and authentic architectural magnificence.
The estate’s commanding presence begins at first sight. Constructed during the height of the Tudor Revival movement in American architecture, this residence showcases the period’s characteristic half-timbering, steep gabled rooflines, and masterful stonework that have been meticulously preserved and enhanced through careful restoration. The property’s elevation and mature landscaping create a sense of arriving at a private compound, where towering oaks and specimen trees frame views while ensuring complete privacy from the outside world.
Upon entering through the estate’s impressive foyer, guests encounter spaces that seamlessly blend historic character with contemporary comfort. The great room, with its soaring beamed ceilings and magnificent stone fireplace, serves as the home’s dramatic centerpiece. Original hardwood floors, restored to their full luster, reflect light from multiple exposures while maintaining the warmth that only genuine aged wood can provide. The fireplace, constructed from locally quarried stone and rising nearly two stories, creates an irresistible focal point that naturally draws groups together during cooler evenings.
Custom millwork throughout the space showcases the craftsmanship of a bygone era, with built-in bookcases, window seats, and architectural details that modern construction rarely attempts. Large leaded glass windows, another hallmark of Tudor Revival architecture, filter light into painterly patterns while maintaining the privacy that makes this estate so special. The room’s generous proportions—easily accommodating 20 for cocktails or intimate groups for conversation—reflect the era’s commitment to gracious entertaining.
The estate’s kitchen represents a masterful renovation that respects historic character while delivering professional-grade functionality. At its heart, a commanding La Cornue range—the choice of Michelin-starred chefs worldwide—offers both gas burners and electric ovens, providing the versatility serious cooks demand. This legendary French range, with its distinctive vaulted oven design and precise temperature control, transforms meal preparation from task to art form.
Surrounding this culinary centerpiece, custom cabinetry provides abundant storage while maintaining period-appropriate aesthetics. Soft-close drawers, pull-out pantries, and specialized storage solutions accommodate everything from everyday dinnerware to extensive entertaining supplies. Carrara marble countertops, selected for both beauty and functionality, provide generous workspace while complementing the kitchen’s sophisticated palette. A substantial center island offers additional preparation space, informal dining for six, and a gathering spot that inevitably becomes the heart of any party.
Professional-grade appliances throughout include a Sub-Zero refrigerator and freezer, ensuring ingredients remain at optimal freshness; a Miele dishwasher so quiet conversations continue uninterrupted; and a built-in espresso system that rivals Manhattan’s finest coffee bars. A butler’s pantry, complete with wine refrigeration and additional storage, facilitates seamless entertaining while keeping utilitarian aspects hidden from view.
The formal dining room exemplifies the estate’s commitment to gracious living. Original oak paneling, carefully preserved and restored, creates an atmosphere of refined elegance that modern materials simply cannot replicate. The room’s proportions, designed when formal dining was a nightly ritual rather than special occasion, comfortably accommodate 12 at the antique mahogany table while maintaining an intimate atmosphere conducive to conversation.
A stunning chandelier, carefully selected to complement the room’s historic character while providing modern illumination, serves as the space’s crowning jewel. French doors open to the estate’s gardens, allowing for seamless flow between indoor and outdoor entertaining spaces during warmer months. Built-in china cabinets display fine porcelain and crystal, while a discrete serving area facilitates formal service when desired.
The estate’s master suite occupies its own wing, ensuring privacy and tranquility. This remarkable space encompasses over 800 square feet, including a sitting area with fireplace, creating a true retreat within the home. The bedroom proper features spectacular garden views through oversized windows, while motorized blackout shades ensure restful mornings regardless of sunrise. Original hardwood floors continue here, warming the space and providing continuity with the home’s public areas.
The master bathroom rivals any five-star hotel, with a deep soaking tub positioned to capture garden views, a separate glass-enclosed rain shower with multiple body jets, and dual vanities topped with marble. Heated floors provide comfort on cool mornings, while a private water closet and abundant storage complete the space. The suite’s walk-in closet, larger than many Manhattan bedrooms, provides organized storage for extended stays with built-in drawers, adjustable shelving, and dedicated spaces for everything from shoes to jewelry.
Five additional bedrooms ensure every guest enjoys privacy and comfort. Each room maintains its own character while providing modern amenities including individual climate control, high-speed WiFi access, and carefully selected furnishings that balance comfort with style. The second-floor guest rooms feature original architectural details—exposed beams, window seats, charming dormers—that create unique personalities while maintaining cohesive design throughout.
Three full bathrooms and two powder rooms mean morning routines proceed without conflict, even with a full house. Each bathroom has been updated with premium fixtures, stone countertops, and tile work that respects the home’s historic character while providing modern functionality. Guest rooms range from intimate spaces perfect for children to substantial suites that rival master bedrooms in typical homes, ensuring appropriate accommodations regardless of group composition.
The estate’s outdoor amenities transform warm-weather stays into resort experiences. The heated gunite pool, measuring 20 by 40 feet, provides serious swimming space while maintaining elegant proportions that complement rather than dominate the landscape. Professional-grade filtration and heating systems ensure crystal-clear water at perfect temperatures from May through October, while automatic covers provide safety and energy efficiency.
The pool house serves as an outdoor living room, complete with comfortable seating, dining space, and a fully equipped bar area. This structure provides shade during peak sun hours, shelter during passing showers, and a natural gathering spot for poolside entertaining. An outdoor kitchen, featuring a Viking grill, refrigeration, and preparation space, means meals can be prepared and served without trips to the main house.
The pool deck, constructed from natural stone that stays cool underfoot even in summer sun, provides ample space for lounging, with room for a dozen chaise lounges without crowding. Mature landscaping provides privacy while allowing sunshine to warm the space throughout the day. Evening lighting transforms the pool area into a magical setting, with underwater lights creating an inviting glow while landscape lighting highlights specimen plants and architectural features.
Nearly two acres of professionally maintained grounds provide endless opportunities for outdoor enjoyment. Mature specimen trees—including centuries-old oaks, flowering dogwoods, and Japanese maples—create a park-like setting that changes dramatically with seasons. Spring brings waves of bulbs and flowering shrubs; summer showcases perennial borders and annual displays; fall delivers spectacular foliage; and winter reveals the property’s architectural bones against pristine snow.
A bluestone terrace adjacent to the main house provides outdoor dining for 12, with a retractable awning offering shade when desired. This space, equipped with heating elements for cool evenings, extends the outdoor season well into fall. Multiple seating areas throughout the grounds offer choices: a quiet reading nook beneath an ancient oak, a morning coffee spot capturing eastern sun, an evening gathering place positioned for sunset views.
The estate’s level lawns provide space for croquet, badminton, or simply stretching out with a book. Children find endless entertainment in the property’s safe, enclosed spaces, while adults appreciate the privacy that allows for complete relaxation. Professional landscape maintenance ensures the grounds always appear their best, with seasonal plantings providing continuous color and interest.
While respecting its historic character, the estate incorporates modern systems that ensure contemporary comfort. A sophisticated HVAC system with multiple zones maintains perfect temperatures throughout, with individual room controls allowing personalized comfort. High-speed fiber optic internet reaches every corner of the property, supporting multiple devices for streaming, gaming, or video conferencing without compromise.
A Sonos sound system provides music throughout public spaces and can be controlled from any smartphone, while smart TVs in bedrooms and gathering spaces offer access to all major streaming services. Security systems, including discrete cameras and professional monitoring, ensure peace of mind without intrusive visibility. Automated lighting systems allow for scene-setting at the touch of a button, while maintaining traditional switches for those who prefer conventional controls.
A three-car garage provides protected parking with additional driveway space for several more vehicles—a crucial amenity for groups arriving separately. The laundry room, equipped with two sets of high-capacity washers and dryers, means even large groups can maintain fresh wardrobes without scheduling conflicts. A mudroom with built-in storage manages coats, boots, and sports equipment, maintaining order despite full occupancy.
Storage throughout the home exceeds typical vacation rental standards, with closets, built-ins, and discrete spaces ensuring luggage and personal items can be properly stowed rather than cluttering living spaces. The estate’s mechanical systems—from water heaters to heating equipment—have been sized for maximum occupancy, ensuring everyone enjoys hot showers and comfortable temperatures regardless of demand.
The estate’s location in Northern Westchester provides remarkable accessibility while maintaining the privacy and tranquility that define true retreats. Just 35 minutes from Midtown Manhattan via Metro-North’s express trains, guests can enjoy Broadway shows, world-class museums, or business meetings while returning to suburban serenity each evening. The nearby Saw Mill River Parkway and I-684 provide direct highway access for those preferring to drive, with the estate’s circular driveway easily accommodating multiple vehicles.
Three international airports—Westchester County Airport (15 minutes), LaGuardia (45 minutes), and JFK (60 minutes)—ensure convenient arrivals and departures regardless of origin. Private aviation users particularly appreciate Westchester County Airport’s fixed-base operators, which provide discrete, efficient service without the delays common at major airports.
Westchester County offers sophisticated shopping, dining, and cultural experiences that rival any major city. The Westchester, one of the nation’s premier shopping destinations, features flagship stores from Nordstrom to Neiman Marcus alongside unique boutiques. Greenwich’s Avenue provides additional upscale shopping just 20 minutes away, with galleries, antique shops, and specialty stores that reward exploration.
Dining options range from Michelin-starred restaurants to beloved local institutions. Blue Hill at Stone Barns, regularly ranked among America’s best restaurants, provides a farm-to-table experience that’s become pilgrimage-worthy for food enthusiasts. X2O Xaviars on the Hudson offers spectacular river views alongside innovative cuisine, while dozens of excellent neighborhood restaurants provide options for every taste and occasion.
Cultural attractions abound, with the Caramoor Center for Music and the Arts hosting world-class performances in a spectacular setting. The Jacob Burns Film Center in Pleasantville screens independent films and hosts filmmaker talks. Museums ranging from the Hudson River Museum to the Neuberger Museum of Art provide rainy-day alternatives, while historic sites like Kykuit (the Rockefeller estate) and Lyndhurst Mansion offer glimpses into the region’s gilded past.
Westchester’s extensive park system provides endless outdoor opportunities. The Bronx River Parkway Reservation offers miles of walking and cycling paths, while Ward Pound Ridge Reservation’s 4,315 acres include hiking trails ranging from gentle strolls to challenging climbs. Golf enthusiasts can choose from dozens of courses, including several ranked among the nation’s best: Winged Foot, Quaker Ridge, and Sleepy Hollow Country Club all lie within 20 minutes.
The Hudson River waterfront provides kayaking, sailing, and paddleboarding opportunities, with several marinas offering rentals and instruction. In winter, nearby ski areas provide family-friendly slopes, while ice skating rinks and cross-country ski trails offer additional cold-weather activities. Tennis courts, both indoor and outdoor, accommodate year-round play, with several clubs welcoming guest players.
Families with children find endless entertainment options nearby. The Westchester Children’s Museum provides hands-on learning experiences, while LEGOLAND New York Resort, just 45 minutes away, offers a full day of themed entertainment. Playland Amusement Park, a National Historic Landmark, combines vintage charm with modern thrills on Long Island Sound’s shores.
Nature centers throughout the county offer educational programs and easy hiking trails perfect for young explorers. The Greenburgh Nature Center, Teatown Lake Reservation, and Muscoot Farm provide opportunities to encounter wildlife, learn about local ecosystems, and experience farm life. Seasonal attractions—from apple picking in fall to maple syrup demonstrations in spring—create memorable experiences for all ages.
Spring arrives dramatically at the estate, with hundreds of bulbs emerging across the grounds. Daffodils, tulips, and crocuses provide waves of color, while flowering trees—cherries, magnolias, dogwoods—create spectacular displays. The pool opens in May, often warm enough for swimming by Memorial Day. Spring in Westchester means farmers’ markets overflowing with early vegetables, garden tours showcasing the region’s horticultural heritage, and perfect weather for hiking without summer’s humidity.
Summer transforms the estate into a private resort. The pool becomes the daily focal point, with breakfast on the terrace segueing into poolside lunches and evening barbecues. Westchester’s summer calendar fills with outdoor concerts, art festivals, and county fairs. The Hudson River becomes a recreational playground, while local farms offer pick-your-own berries and vegetables. Evening temperatures typically remain comfortable, allowing for outdoor dining throughout the season.
Fall may be Westchester’s finest season, with the estate’s mature trees providing a private foliage display that rivals any New England destination. The pool remains usable through October’s Indian Summer days, while evenings grow cool enough to enjoy the great room’s fireplace. Apple orchards throughout the county offer picking, cider pressing, and harvest festivals. The region’s numerous Halloween attractions—from historic mansion tours to haunted hayrides—provide seasonal entertainment.
Winter transforms the estate into a cozy retreat where the home’s multiple fireplaces truly shine. Snow-covered grounds create a magical landscape visible from every window, while the garage’s protection becomes particularly appreciated. Nearby ski areas provide winter sports, while the estate’s proximity to Manhattan means Broadway shows and museum visits offer perfect cold-weather activities. The holiday season brings special magnificence, with the home’s architecture providing perfect backdrop for seasonal decorations.
The estate’s combination of grand public spaces and extensive grounds makes it ideal for hosting special celebrations. Intimate weddings of up to 50 guests find perfect settings between the great room’s dramatic architecture and the garden’s natural beauty. Birthday celebrations, anniversaries, and family reunions benefit from spaces that accommodate both large gatherings and smaller breakout groups.
The kitchen’s professional capabilities support catered events or ambitious home cooking, while the butler’s pantry facilitates seamless service. Multiple gathering spaces mean different activities can occur simultaneously—children playing in one area while adults enjoy conversation elsewhere. The pool area provides additional entertainment space during warm weather, effectively doubling the estate’s capacity for outdoor events.
Business groups increasingly seek residential settings for strategic planning sessions, team building exercises, and executive retreats. The estate provides an ideal environment for such gatherings, with spaces that transition seamlessly from focused work sessions to relaxed social interaction. The dining room serves as an impressive conference room, while the great room accommodates presentations. Multiple bedrooms allow executive teams to stay on-site, fostering the informal interactions that often prove most valuable.
High-speed internet throughout supports video conferencing and collaborative work, while the property’s privacy ensures confidential discussions remain secure. The pool and grounds provide recreational options that build team cohesion, while proximity to Manhattan allows for easy addition of outside facilitators or speakers. Evening gatherings around the fireplace or pool create environments where hierarchies relax and genuine connections form.
Hudson Valley Luxury Resorts brings decades of hospitality expertise to ensure every stay exceeds expectations. Pre-arrival planning begins with detailed consultation to understand specific needs and preferences. Whether arranging for pre-stocked groceries, coordinating airport transfers, or securing reservations at sought-after restaurants, our team ensures arrivals are seamless and stays are memorable.
During your residence, our property management team remains available 24/7 to address any needs that arise. From arranging additional housekeeping to coordinating maintenance issues, we handle concerns immediately and professionally. Our local knowledge means we can recommend everything from the best hiking trails to emergency pediatricians, providing the support that transforms good vacations into great ones.
Understanding that every group has unique interests, we offer customized experience planning that maximizes your Westchester stay. Wine enthusiasts might enjoy a curated tour of Hudson Valley wineries with private tastings and meet-the-winemaker opportunities. Art lovers could experience private gallery tours, artist studio visits, and even arranged purchases of local works. Families might appreciate customized itineraries that balance adult interests with child-friendly activities.
Our partnerships with local providers mean guests receive preferred treatment and access to experiences not generally available. Private chef services can transform the estate’s kitchen into a culinary classroom or provide memorable dinner parties. Massage therapists, yoga instructors, and personal trainers can come to the property, creating a private spa or fitness experience. Whatever your interests, we can arrange experiences that elevate your stay from accommodation to adventure.
Every aspect of the Westchester Castle Tudor Estate reflects our commitment to providing exceptional vacation experiences. Linens are premium quality and professionally laundered. Amenities are regularly updated and meticulously maintained. Cleaning standards exceed hotel levels, with additional services available as needed. We understand that our guests have choices, and we strive to ensure choosing Hudson Valley Luxury Resorts remains their best decision.
This exceptional estate accommodates various group types with equal success. Multi-generational families appreciate bedrooms that provide privacy while common areas encourage togetherness. Friend groups enjoy the resort-like amenities and space to pursue different activities. Corporate groups value the professional functionality within a relaxed setting. Wedding parties find perfect spaces for both preparation and celebration.
The property’s flexibility means it adapts to different needs without compromise. Early risers can enjoy coffee on the terrace without disturbing late sleepers. Cooks can prepare elaborate meals while others relax by the pool. Children can play safely in enclosed grounds while adults enjoy uninterrupted conversation. This versatility, combined with the estate’s inherent luxury, creates experiences that satisfy every guest.
The Westchester Castle Tudor Estate operates with a three-night minimum stay, allowing guests to truly settle in and experience the property’s full potential. Peak seasons—summer for pool enjoyment, fall for foliage, December for holidays—book months in advance, making early planning essential. Longer stays of a week or more provide opportunity to explore the region thoroughly while enjoying the estate as a true home base.
Pricing reflects the property’s exceptional nature and includes all utilities, high-speed internet, and basic amenities. Additional services—extra housekeeping, chef services, experience planning—can be arranged for supplemental fees. We recommend discussing specific needs during booking to ensure appropriate arrangements and accurate pricing.
The Westchester Castle Tudor Estate offers more than mere accommodation; it provides entry into a lifestyle typically reserved for the fortunate few who call such properties home. From the moment you enter the gates until your reluctant departure, every element conspires to create memories that endure long after your stay ends. The estate’s combination of architectural grandeur, modern luxury, and perfect location creates opportunities limited only by imagination.
Whether seeking a family gathering place, a base for New York exploration, or simply an escape from ordinary life, this remarkable property delivers experiences that exceed expectations. Here, in Westchester County’s most desirable location, surrounded by beauty both natural and architectural, your extraordinary escape awaits.
Hudson Valley Luxury Resorts invites you to experience the Westchester Castle Tudor Estate, where historic grandeur meets modern luxury, where privacy ensures relaxation, and where every detail has been considered to create perfection. Your castle awaits—complete with pool, proximity to Manhattan, and possibilities as endless as your imagination.
Start Date | End Date | Per Night | Minimum Stay |
---|---|---|---|
2025-09-10 | 2025-09-10 | $521 | 2 Nights |
2025-09-11 | 2025-09-11 | $401 | 1 Night |
2025-09-14 | 2025-09-14 | $618 | 2 Nights |
2025-09-15 | 2025-09-15 | $406 | 2 Nights |
2025-09-16 | 2025-09-16 | $404 | 2 Nights |
2025-09-17 | 2025-09-17 | $420 | 1 Night |
2025-09-23 | 2025-09-23 | $374 | 2 Nights |
2025-09-24 | 2025-09-24 | $382 | 2 Nights |
2025-09-25 | 2025-09-25 | $403 | 1 Night |
2025-10-04 | 2025-10-04 | $693 | 2 Nights |
2025-10-05 | 2025-10-05 | $621 | 2 Nights |
2025-10-06 | 2025-10-06 | $635 | 2 Nights |
2025-10-07 | 2025-10-07 | $635 | 2 Nights |
2025-10-08 | 2025-10-08 | $569 | 1 Night |
2025-10-12 | 2025-10-12 | $884 | 4 Nights |
2025-10-13 | 2025-10-13 | $729 | 3 Nights |
2025-10-14 | 2025-10-14 | $668 | 3 Nights |
2025-10-15 | 2025-10-15 | $604 | 2 Nights |
2025-10-16 | 2025-10-16 | $886 | 1 Night |
2025-10-21 | 2025-10-21 | $539 | 2 Nights |
2025-10-22 | 2025-10-22 | $548 | 1 Night |
2025-10-26 | 2025-10-26 | $600 | 2 Nights |
2025-10-27 | 2025-10-27 | $532 | 2 Nights |
2025-10-28 | 2025-10-28 | $539 | 2 Nights |
2025-10-29 | 2025-10-29 | $549 | 2 Nights |
2025-10-30 | 2025-10-30 | $601 | 1 Night |
2025-11-02 | 2025-11-02 | $601 | 2 Nights |
2025-11-03 | 2025-11-03 | $534 | 2 Nights |
2025-11-04 | 2025-11-04 | $602 | 2 Nights |
2025-11-05 | 2025-11-05 | $611 | 1 Night |
2025-11-09 | 2025-11-09 | $739 | 4 Nights |
2025-11-10 | 2025-11-10 | $729 | 3 Nights |
2025-11-11 | 2025-11-11 | $734 | 3 Nights |
2025-11-12 | 2025-11-12 | $611 | 2 Nights |
2025-11-13 | 2025-11-13 | $632 | 2 Nights |
2025-11-14 | 2025-11-14 | $698 | 4 Nights |
2025-11-15 | 2025-11-15 | $713 | 4 Nights |
2025-11-16 | 2025-11-16 | $629 | 4 Nights |
2025-11-17 | 2025-11-17 | $593 | 3 Nights |
2025-11-18 | 2025-11-18 | $602 | 3 Nights |
2025-11-19 | 2025-11-19 | $674 | 3 Nights |
2025-11-20 | 2025-11-20 | $683 | 4 Nights |
2025-11-21 | 2025-11-21 | $701 | 4 Nights |
2025-11-22 | 2025-11-22 | $716 | 4 Nights |
2025-11-23 | 2025-11-23 | $692 | 3 Nights |
2025-11-24 | 2025-11-24 | $656 | 2 Nights |
2025-11-25 | 2025-11-25 | $665 | 1 Night |
2025-12-01 | 2025-12-01 | $1,356 | 3 Nights |
2025-12-02 | 2025-12-02 | $1,365 | 3 Nights |
2025-12-03 | 2025-12-03 | $1,374 | 3 Nights |
2025-12-04 | 2025-12-04 | $1,446 | 4 Nights |
2025-12-05 | 2025-12-05 | $1,464 | 4 Nights |
2025-12-06 | 2025-12-06 | $1,473 | 4 Nights |
2025-12-07 | 2025-12-07 | $1,455 | 4 Nights |
2025-12-08 | 2025-12-08 | $1,419 | 4 Nights |
2025-12-09 | 2025-12-09 | $1,428 | 4 Nights |
2025-12-10 | 2025-12-10 | $1,437 | 4 Nights |
2025-12-11 | 2025-12-11 | $1,446 | 4 Nights |
2025-12-12 | 2025-12-12 | $1,464 | 4 Nights |
2025-12-13 | 2025-12-13 | $1,473 | 4 Nights |
2025-12-14 | 2025-12-14 | $1,455 | 4 Nights |
2025-12-15 | 2025-12-15 | $1,419 | 4 Nights |
2025-12-16 | 2025-12-16 | $1,428 | 4 Nights |
2025-12-17 | 2025-12-17 | $1,437 | 4 Nights |
2025-12-18 | 2025-12-18 | $1,446 | 4 Nights |
2025-12-19 | 2025-12-19 | $1,289 | 3 Nights |
2025-12-20 | 2025-12-20 | $1,299 | 2 Nights |
2025-12-21 | 2025-12-21 | $1,269 | 1 Night |
2025-12-26 | 2025-12-26 | $1,289 | 4 Nights |
2025-12-27 | 2025-12-27 | $1,299 | 4 Nights |
2025-12-28 | 2025-12-28 | $1,269 | 4 Nights |
2025-12-29 | 2025-12-30 | $1,500 | 3 Nights |
2025-12-31 | 2025-12-31 | $1,259 | 3 Nights |
From $875 / Per Night
Added: August 17, 2025
Price On Call
Added: January 24, 2024
What is there more kindly than the feeling between host and guest?
Aeschylus