Sleepy Hollow NY Real Estate & Homes for Sale

Experience simplicity and expansive views at the Volner House, where modern living meets the majestic Hudson River. Just 45 minutes from New York City, this private oasis sits gracefully between the Hudson National Golf Course and the vast expanse of the Hudson River, offering unparalleled vistas of river bays, marinas and the iconic Palisades. The original house was designed in 1951 by modernist H. Seymour Howard Jr., a visionary of Harvard's Graduate School of Design, the Volner House stands as the original cornerstone of a modernist enclave along the Hudson River. In addition to the original house being meticulously restored, a pool and guest house, as well as a 3-car garage, was recently added to the property.

This New England-style center hall colonial sits majestically atop a long private drive in idyllic back country Greenwich. The combination of outdoor spaces, set on 4 acres, make this home ideal for relaxation & entertaining...an in-ground pool, pool house, tennis court, and a versatile heated barn for creative pursuits. The interior features truly create an inviting atmosphere. Custom moldings, a wood-burning fireplace & beamed ceilings in the formal living room add character & elegance. The spacious dining room, with its vaulted ceiling & built-ins, can comfortably host large gatherings. In the chef's kitchen, the gas range & center island make cooking a pleasure, while the brick fireplace adds a unique charm that sets it apart from typical kitchens. The family room has walls of windows, allowing natural light to flood the space. All of these features & a flexible floor plan contribute to making this home so special. The main-level primary bedroom suite has an adjacent space to work or relax. Upstairs, there's a 2nd primary bedroom with a concept to add a full bath. There are 3 more bedrooms & 2 full baths on this level. Above the 2-car garage, a bedroom, den & bath create a very private suite for guests or extended family. Find more space & a wine cellar on the lower level. New exterior paint will bring this home back to its original splendor. More ways to add value exist here. Zoned for horses & beach rights. This wonderful property has all one could need to enjoy life!

Grand Greenwich Estate | Luxurious Living on 4.3 Acres Nestled at the end of a quiet cul-de-sac, 27 Stiles Lane is a magnificent brick manor set on 4.3 private acres of lush, manicured grounds. Offering 7,438 square feet of refined living space, this exceptional estate is designed for those who appreciate elegance, comfort, and unparalleled amenities. Inside, the grandeur unfolds with six ensuite bedrooms, ensuring ultimate privacy and convenience. The heart of the home features two fireplaces, creating warm and inviting spaces for relaxation. A gorgeous library with custom millwork is a sanctuary for book lovers or an ideal work-from-home retreat. Step outside to discover your resort-style backyard, where an oversized pool, tennis court, and sprawling stone patio set the stage for effortless entertaining. Gather around the fire pit under the stars or enjoy peaceful moments in this secluded oasis. A bonus room offers endless possibilities-fitness studio, media lounge, or playroom-while a three-car garage provides ample storage. This is more than a home-it's a private Greenwich retreat where every detail is designed for luxury living.

BELLE HILL FARM. Reminiscent of the great country estates of Normandy. Long drive through manicured grounds to circle surrounding a majestic Sargent's Weeping Hemlock. Absolutely breathtaking grounds with specimen trees & manicured gardens. Impressive Brick & Stucco European Manor, circa 1942. Spectacular restoration & addition using the finest materials. Rooms of perfect proportion with incredible detailing. Meticulously appointed living space. Formal rooms for entertaining. Chef's Kitchen. Incredible Primary Suite. 4 additional Bedrooms. Gym & 2 Home Offices. Pool, Spa & beautiful Pool House. 3 Stall Barn, paddocks & riding trail access. Garden & Greenhouse. Nearly 9 acres including Caretaker's Cottage on separate parcel. Backs up to protected Greenwich Land Trust. Remarkable!

Stunning estate in Greenwich's prestigious Back Country. Set on 4 acres of rolling lawns, this 5,200+ sq ft Colonial blends timeless charm with modern luxury and privacy. Enter through a gated stone entrance to a home beautifully renovated by renowned Lighthouse Architects, with plans for expansion. The magnificent primary suite features a private boudoir, mahogany vaulted ceiling, and fireplace. Four additional bedrooms complete the second floor. Expansive living spaces are ideal for both intimate and grand-scale entertaining. Enjoy sunset views over sweeping lawns, a sparkling pool, and scenic Laub Pond. Minutes from top schools and country clubs.

Elegantly renovated 6 bed, 6.2 bath Georgian Colonial w/stunning finishes & custom millwork on 4+ acres bordering the Fairchild Wildflower Sanctuary providing privacy. The stunning new kitchen & adjacent family rm., opens to spacious outdoor living for entertaining w/expansive terraces, heated pool w/spa, outdoor BBQ, pool house w/kitchen & a paddock with 3 stall stable. Arched doorways lead into the living rm., formal dining rm., wood paneled office & elegant family rm. w/serene views of surrounding woods. The 2nd floor comprises the primary bedroom suite w/coffered ceiling, & 3 more ensuite bedrooms. The 3rd floor is a private suite w/bedroom, sitting area, balcony, office space & bath. A finished walkout LL w/gym, media rm., massage rm., bath & sauna completes a rare blend of elegance, outdoor living and equestrian charm - all just minutes from town.

Restored one of kind home with cathedral celling's nested in over two acres of parklike land among multi million $ homes only 45 minutes from NYC and 10 minutes from Greenwich Train Station. The versatile floor plan offers room for families to play or at-home working situations. Several light filled formal rooms, 4 En-suite bed rooms and 5 luxurious full bath can be used as needed. Primary suite with sitting room over looking garden and access to pool enjoys spa like marble bath with steam room system and dressing room. Brand new chef kitchen with top of the line appliances opens to large dinning/family room and delightful patio and pool area surrounded by gardens and pond perfect for entertaining. Walk out lower level has 2 full bath, a bed room and large exercise/ yoga space. Heated driveway, All renovated with ultimate craftmanship and best of materials. Large chandelier and antique scones are excluded. Interior and exterior cameras. please see list of features

Charming Greenwich country compound offers an inviting, updated 1900 farmhouse with beautiful gardens on 2+ level acres. This gracious 3,264 sq. ft. home blends modern amenities with original details such as hardwood floors and high ceilings. Main level features a granite-clad kitchen open to breakfast room/lounge; dining room with French doors to the side yard; wood-beamed living room with fireplace; a library and family rooms with terrace access; plus, two powder rooms and a laundry room. Second floor has the primary suite with sliding barn door entrance, walk-in fitted closet and bath; plus, an en-suite bedroom; two additional bedrooms and another bath. A barn with two-car garage has a studio above. Potential expansion and pool site. Within one hour of NYC.

Immediate Occupancy, construction just completed. The culmination of a visionary architectural endeavor, this residence stands complete, offering a move-in-ready sanctuary of unparalleled modern luxury. This meticulously executed, ground-up transformation has birthed an ultra-modern masterpiece, a testament to innovative design where contemporary aesthetics seamlessly merge with the pinnacle of refined living. Spanning an impressive 5,230 sqft , this home is gracefully situated on 2.5 acres of meticulously landscaped grounds, providing both privacy and a sense of expansive tranquility. Custom-crafted cabinetry and state-of-the-art Miele & Bosch appliances underscore a commitment to both quality and refined elegance.The generously proportioned living areas extend effortlessly into the outdoor environment, blurring the lines between interior and exterior and cultivating an integrated living experience that embraces the surrounding natural beauty. Each of total of 5 bedrooms serves as a meticulously designed retreat, offering a haven of tranquility and comfort, while the spa-inspired bathrooms provide an indulgent escape, a sanctuary for relaxation and rejuvenation. State-of-the-art amenities further elevate the living experience, ensuring that this ultra-modern residence represents the zenith of contemporary residential design. Embrace an idyllic lifestyle in Greenwich, a prestigious enclave offering a serene retreat with effortless access to NYC.

Country meets modern is this beautifully renovated turn-key home set on a private cul-de-sac. This home offers all the amenities to enjoy today's modern lifestyle. It's the perfect size for your first home in Greenwich or to scale down from a larger home. A two story entry welcomes you home. The living room features new hickory hardwood floors, glass front wine cabinets and a wet bar to service the adjacent covered porch and cedarwood spa for outdoor entertaining. The new reconstructed carrera marble and soapstone kitchen features Wolfe, Sub Zero and Miele appliances. The new primary bedroom has a cozy fireplace, direct access to the cedarwood spa and a new luxurious bath. 3 en suite bedrooms are on the upper level. The lower level offers an office or rec room and the fifth bedroom/exercise room. All this close to Greenwich's great restaurants,parks and beaches as well as a short drive to Armonk and Bedford, NY. Possible pool site in attached documents.

Peaceful, serene and private best describes this property located on a secluded lane off Lake Avenue. Meticulously renovated with both functionality and playfulness in mind. The stunning entry foyer has soaring windows inviting in an abundance of natural light. A Bilotta designed kitchen, has custom cabinetry and high-end appliances and finishes. There is a spacious primary with fireplace, luxury bath and private balcony. Also, four additional bedrooms on the same level, ensuite with thoughtfully designed closets. A separate staircase leads to a private bedroom suite with kitchenette, ideal for staff, guests or in-laws. The parklike setting has tennis court, private garden area with pool, terrace and you're ready for relaxing summer fun.

Discover the enduring beauty of this stately 1900 Georgian Colonial. Set on a corner lot on one acre offers over 7,500 square feet of living space, 9 bedrooms, 5 full bathrooms, and 8 working fireplaces, a true testament to timeless elegance and old-world craftsmanship. Step inside and you're greeted by exquisite period details, ornate millwork, soaring 12ft ceilings, original leaded glass windows and build-ins that echo the grandeur of a bygone era. Graceful formal rooms, a sweeping central staircase, and sun-drenched spaces throughout offer the perfect canvas for restoration and refinement. Entertain or relax on the sweeping veranda overlooking a private gated pool and grounds. Possible Subdivision site. Interested parties must perform own verification.

Located in the gated community of Conyers Farm, a private, lakefront country estate, ideally perched on over 10 acres. This extraordinarily chic shingle and stone residence was originally built in 2002 with enhancements and an expansion in 2017. Included in the extensive interior and exterior improvements, is a 6,500+ sf addition offering a remarkable, one of one, full size regulation tennis arena which doubles as a party barn and NBA size basketball court, an oversized pool with hot tub, outdoor kitchen, outdoor fireplaces, a golf simulator and a golf green. At every turn, painstaking attention to detail abounds with lofty beamed ceilings and a stone fireplace in the family room, a large formal dining room, private office, renovated main house kitchen with a service pantry and wine cellar complete the first level. A luxurious and calming owner's suite with walk in dressing room, four additional ensuite bedrooms plus a separate 1-bedroom cottage provide ample living quarters. The third floor adds an indoor sport court, bar area, gym, bunk room and bath. With a Greenwich PO and access to the polo fields, 9 Cowdray Park also features a dock on the idyllic 100+ acre Converse Lake. Tennis, golf, basketball and boating - recreation at your fingertips.

Nestled within the confines of Conyers Farm, this French Normandy chateau epitomizes exclusivity and grandeur. Blending exquisite architecture with lavish comforts and resort amenities that elevate luxury living to new heights. Showcasing impeccable materials, palatial entertaining spaces, a luxurious kitchen, family room, paneled library, and a sprawling terrace overlooking the pool. Seven bedrooms include a lavish primary suite with dual baths and two walk-in closets with dressing rooms and a balcony, while the garden level features a theater, lounge, bar, spa facilities with an indoor resistance pool, spa tub, sauna, gym, bath, family room/fireplace! Outside, you'll revel in the peace and beauty of the serene 13+ acres, where lush lawns, verdant woodlands, and vibrant gardens will surely enchant. This gorgeous setting is further enhanced by guarded 24/7 security, easy access to nearby Greenwich, Bedford, Armonk, Westchester Airport, and New York City, less than an hour away.

Located in the gated community of Conyers Farm, a private, lakefront country estate, ideally perched on over 10 acres. This extraordinarily chic shingle and stone residence was originally built in 2002 with enhancements and an expansion in 2017. Included in the extensive interior and exterior improvements, is a 6,500+ sf addition offering a remarkable, one of one, full size regulation tennis arena which doubles as a party barn and NBA size basketball court, an oversized pool with hot tub, outdoor kitchen, outdoor fireplaces, a golf simulator and a golf green. At every turn, painstaking attention to detail abounds with lofty beamed ceilings and a stone fireplace in the family room, a large formal dining room, private office, renovated main house kitchen with a service pantry and wine cellar complete the first level. A luxurious and calming owner's suite with walk in dressing room, four additional ensuite bedrooms plus a separate 1-bedroomcottage provide ample living quarters. The third floor adds an indoor sport court, bar area, gym, bunk room and bath. 9 Cowdray Park also features a dock on the idyllic 100+ acre Converse Lake and access to the polo fields. Tennis, golf, basketball and boating - recreation at your fingertips.

This home was built with great bones and is now ready for a full renovation. OR, take it down and build new - see photos. Gorgeous 2.3 acres combine with a premier Round Hill Rd. address! The topography of 121 Round Hill Road offers uncommon long vistas from all floors with a unique blend of openness and privacy. Irrigated, manicured lawns, plantings, old stonewalls, and natural areas provide a tranquil, relaxing estate setting. Explore the above-ground, day-lit, walk-out lower level for exercise and other recreational rooms as well as another access to the south-facing pool, and a level backyard. Location, Location, Location - great quality of land - and your imagination can lead to your dream home and great value. Also, ask LB about new construction plans.

Beautifully renovated 5 bedroom Colonial on a quiet cul-de-sac in the Glenville school district. This home has a great layout for entertaining family & friends. Enter into a 2-story foyer with a curved staircase. The living room has several windows & fireplace. There is a formal dining room off the stunning redone kitchen & an adjacent family room with fireplace. Both rooms lead to a covered large deck & an open deck that overlooks the pool, koi pond with waterfall, hot tub & stone patio. The second level has a cathedral ceiling primary suite with luxe new bath, walk-in closet & balcony overlooking the pool. This level has 3 additional bedrooms & new bath. Bonuses: generator, 2 car garage, separate au pair/office space & basement storage. Close to school, parks, restaurants and shops.

This is a must see spacious Mid- Century 5 bedroom, 3 1/2 bath 3317 SF home. Beautifully rebuilt and renovated in 2023 on a very quiet cul de sac on 1.25 acre of land. It has features unmatched in comparably priced homes with soaring ceilings flooding in light through its surrounding trees in its natural environment. It has not one but two contemporary fireplaces in separate living areas, an open dream kitchen with stainless steel appliances and a central island. Large and private primary bedroom suite with two walk-in closets and luxury bath. The light and bright downstairs offers a bedroom, bath, home office and large sunny family room, a large area that can be used as an exercise room plus large storage. . The house has been wired for internet and AV charging station. Two patios for gathering and hosting. Possible pool site, 6 Minutes to town

Step into luxury with this newly staged custom built home in one of Greenwich's prestigious associations. Perfectly situated near downtown, this elegant property offers a blend of sophistication and convenience- now at an improved price! A stunning custom built white Georgian Colonial in the coveted mid country Sherwood Farm Association is sited on a picturesque level acre lot. This six bedroom masterpiece spans four meticulously designed levels showcasing exceptional woodworking craftsmanship and architectural details throughout. Enter through the grand foyer with a sweeping circular staircase, leading to a breathtaking living room with double height ceilings and stunning floor to ceiling fireplace. The first floor features elegant French doors that open to a large formal dining room with a fireplace, offering scenic views of the expansive terrace. The cherry-paneled library provides a refined retreat, while the classic Christopher Peacock kitchen, complete with a rotunda breakfast room is a culinary dream.

This stunning brick and clapboard 7 bedroom home with open floor plan was completely renovated, expanded and redesigned for modern living. Beautifully sited high and west facing, the property extends 2.11 acres on one of the most coveted lanes in mid-country. The exquisite grounds have been creatively designed by Glen Gate including a new private driveway with parking court. Every element of this 12,200 sq ft luxury home on 4 levels has been carefully curated including European windows, 6-inch white oak flooring, Taj Mahal quartzite island, glistening marble bathrooms, deluxe primary suite, Shoreline pool with auto cover, 4-car garage with extra height, Lutron system, exercise center and more. This is truly a scarce opportunity in the heart of mid-country for a sensational new home.

Welcome to this impeccably maintained and charming 3-bedroom home in the heart of Pemberwick. The sunlit, renovated kitchen flows into a formal dining room and spacious living room with fireplace and bonus office/den. Sliders lead to a fully fenced, beautifully landscaped backyard-ideal for entertaining or play. Upstairs, the primary suite features a walk-in closet and spa-like bath with Jacuzzi. Two large bedrooms share a full hall bath. Located in a family-friendly neighborhood steps to Pemberwick Park, and minutes to Byram Park's beach, pool, and marina. Convenient to I-95 and the Merritt.

Eight private, gated acres showcase a sprawling back-country home with stone terraces, secluded backyard, fountain and resort-style amenities including tennis court, indoor pool, spa, steam room and separate office. Thoughtful floor plan accommodates both grand scale entertaining as well as comfortable everyday living with elegant formal rooms, fireplaces in living, family rooms and library; gourmet and catering kitchens. Twelve bedrooms provide plenty of sleeping options with two main floor guest suites, second floor primary suite with fireplace and separate two bedroom suite with sitting room over four-car garage. Lower level reveals tasting room/wine cellar; media room with bar, gym and half bath. Located just minutes from town and schools with views of Rockwood Lake and across from Babcock Preserve.

Impeccably maintained, spacious and sunny end unit! Two generously sized bedrooms, one ensuite, plus open office/study area, 3.1 baths, eat in kitchen, dining area, large living room with wood burning fireplace, deck and finished/walk out lower level. Central A/C, hardwood floors throughout. Close to shops, restaurants, parks, beaches, train and major highways for an easy commute! 2 assigned parking spaces. 2 Pets - 25 lbs. each maximum. Parking for 81 Pembroke unit a is on the 79 building side the middle slot and on the 81 building side the one closest to the building. Please park there when showing thank you.

A true home connoisseur's dream! Newly renovated Mid-century modern home is reimagined for today! This unique home offers a RARE opportunity positioned to attract positive energy & offer physical features like SS appl & designer finishes. The home is embraced by harmonizing nature visible thru soaring double-height glass walls. Perched on serene 4+ acres yet minutes to train for NYC express. Guests are greeted by 2 story dramatic glass front doors that set the stage for the interior architectural brilliance found within. The grand foyer w soaring ceilings invites you to come into breathtaking nature views permeating walls of glass. This exceptional home blends the earthy tones & natural materials like natural HW, to create a warm, therapeutic yet sophisticated atmosphere. The open floor plan flows effortlessly thru the main areas encountering sunken liv rooms and elevated retreats for many uses. Heart of the home is the chef's kitchen featuring an 8 burner Wolf oven, custom cabinets, quartz island & vaulted ceilings. The home boasts 7 bedrooms -5 are En Suites. The Prim bedroom suite boasts a linear FP, spa-inspired bath, sitting room, priv deck, W-I-C & sep shoe closet. Add'l two En Suite Bedrooms are on the main and LL offer flexibility for guests. Nine decks provide tranquil escapes and LL primed for a wellness center, gym, yoga rm & sauna. Mins to DT Greenwich. This timeless Mid-century modern gem offers both serenity & convenience. Your new lifestyle awaits at 69 Taconic

Modern One-Bedroom Condo with Garage Parking and Prime Commuter Access Welcome to effortless living in this light-filled one-bedroom, one-bath residence built in 2005. Thoughtfully designed with a galley kitchen featuring a breakfast bar, this home offers a seamless blend of functionality and style. Enjoy oversized windows that flood the space with natural light, creating a warm and inviting atmosphere. This pet-friendly building includes a well-equipped exercise room, secure garage parking, and is ideally located just minutes from major highways, public transportation, and Metro-North-making it a commuter's dream. This home offers comfort, convenience, and a low-maintenance lifestyle in a well-maintained community.