Pleasantville NY Real Estate & Homes for Sale

INVITING, LIGHT FILLED HOME in the Greenwich countryside. Ideal for a family compound. Features a stylish cottage and stables. Enjoy the peaceful surroundings of nature only 39 miles from NYC. Bordered by hundreds of acres of Audubon nature preserves and over 125 miles of riding trails, this property is a nature lover's dream! The home's open space floor plan is extremely versatile. A plethora of windows keep the space cheerful and bright while generous gathering spaces encourage joyful entertaining of extended family and friends. Two primary suites in separate wings allow for a privacy. The sunny walkout lower level offers another suite of roomaway from household distractions. Updated mechanical systems and back up generator assure a worry free lifestyle. THE COTTAGE has been remodeled into a sweet space. Sited away from the main house with a private driveway access, this sophisticated charmer contains a living/dining area, bedroom, full bathroom, kitchen and walkout lower level with a full laundry and storage area. Ideal for a guest cottage, an office or a caretaker's residence. THE STABLES were thoughtfully constructed in 2010 to house quality competition horses. Some 12 x12 box stalls include attached paddocks. A tack room, feed room, wash room, hay lofts and turn out areas are also included. The riding arena was designed and built with excellent footing and drainage. Property abuts miles of well-groomed riding trails. A fabulous family retreat.

Enter a world of refined luxury, fine craftsmanship and magical outdoor living located off Round Hill Road on a quiet cul-de-sac. Timeless architecture and modern amenities create the perfect setting for entertaining indoors while seamlessly flowing to a modern, but contextual interpretation of a traditional French parterre garden. A stunning home that features high ceilings throughout, architecturally appointed doorways & moldings, spacious rooms with large windows & French doors providing an abundance of natural light to entertain the most intimate of gatherings or a full scale event. Enjoy a beautifully appointed Christopher Peacock kitchen, dramatic vaulted breakfast room, adjacent family room and first floor primary retreat overlooking the tranquil pool, spa and pool house. Lush and vibrant 4 acres designed by landscape architect Lignin Group offers a perfectly choreographed layout, both in sequence and seasonality and takes you through a series of outdoor rooms each as their own extension of their interior counterparts. Minutes to town & school.

A rare opportunity for Midcentury Modern enthusiasts to own a house designed by renowned Bauhaus Architect Marcel Breuer in 1950. Privately set on a 3/4 acre, in-town parcel in the Village of Croton-on- Hudson, this 2,292 square foot, one-story, 3-bedroom, 1 1/2 bathroom residence faces public woodlands through an expansive wall of windows. This architectural gem has been meticulously restored by the current owners. It's exterior features a distinctive butterfly roof, Cypress vertical siding, and steel casement windows, nestled against a rock outcropping. A central entry leads to three bright bedrooms on one wing, and free-flowing living spaces on the other. The living room features a unique locally- quarried stone fireplace, original bluestone floor, and oversized picture window framing the private patio and gardens. The updated kitchen includes stainless-steel cabinetry, Caesarstone countertops and all Bosch appliances. The original screened porch was enclosed as an open-plan concept family and dining room, and seamlessly added are a bright mudroom and large home office/studio. A bonus work area is the original one-car garage, which was converted to a 290 square foot finished space and used as a studio (not included in the listed total square footage). Extensive gardens, a fenced organic vegetable garden and stone pathways add to the outdoor appeal. The mature landscaping gives the house privacy, a feeling of seclusion and connection with nature.

Winding tree-lined driveway with front gardens lead to a private 5.64 acres romantic estate of Edwardian mansion. Accomplished with the finest materials, finishes and craftsmanship throughout 13,365SqFt of living space - a total of 26 rooms, 10 fireplaces, 9 bedrooms, 10 bath - builded big, solid with light, airy rooms and accents to details is a cut above what anyone is used to. The oak french door grand entrance welcomes you to a 2-story foyer with a staircase to the second level. Flowing into light-filled open living areas to a great room, living room, a built-in oak shelf office, music room, the formal dining room that easily seats 20, chef's kitchen with high end stainless steel appliances and walk-in pantry room. A family room with a cathedral ceiling, wood beams and a spiral filigree staircase takes you to the second level of the Master Suite and additional bedrooms. Low level offers billiard room, entertainment room, gym room, a study, media room, wine cellar, and a staff wing that has two bedrooms, one bath, an office, a laundry room, and a kitchen. Multiple French glass doors open to a terrace overlooking the pool area. A unique architectural design of living space offer comfort at the highest level. East Branch Byram River, that's crossing the back of the property, where 'Wild Flower Sanctuary' is calling for an adventurous hike of very quiet and deep woods serene at all times. Truly one of a kind, welcoming its new owner.

This is the moment to design and build an extraordinary dream home. This 4.35-acre site is tree lined, private and picturesque. The positioning of a home on this lot with a pool site would be like no other. With a quiet setting and easy access to the Merritt Parkway and short drive to town the convenience and possibilities are endless. The pastoral Back Country is defined by the meandering streams, the pronounced rock outcroppings, winding roads and open meadows. This area is the perfect backdrop and setting for the new construction home awaiting this exceptional site. Explore now before this golden opportunity is gone! The lot is available and can be sold separately.

Stately gated 6-bedroom Georgian Colonial set on four picturesque manicured acres with 50' pool and expansive terraces provides the ideal family home minutes from the towns of Greenwich, Armonk and Bedford in peaceful backcountry Greenwich. Classically appointed, bright interior showcases well-scaled rooms with 10' ceilings and custom millwork. Highlights include an open plan kitchen, breakfast room, double height family room with wood-burning fireplace and oversized windows that fill the room with light. Elegant wood-clad office, sunroom, and main floor bedroom with sitting/music room allows for privacy when guests come to stay or could be transformed into a first floor primary suite.

An exceptional residence meticulously designed and built by a notable developer as his personal dwelling. This six-bedroom Stone/Cedar home sprawls across 2.46 private, gated acres positioned just off Round Hill Road with stunning entertaining areas including a pool, pool cabana with outdoor kitchen and fireplace. Ideal blending of traditional architecture with an contemporary open floor plan boasting 10-foot ceiling heights, this bespoke home is a testament to luxurious living, nestled in a coveted neighborhood, surrounded by walking trails, close to private and public schools, just minutes from town. Designed with meticulous attention to detail, the 13,000+ sq. ft. home features custom millwork, five fireplaces, tall ceilings, and a 3-stop elevator. The main floor highlights elegant formal rooms flowing seamlessly into casual spaces. Spectacular custom kitchen with multiple pantries; family room with French doors to covered porch, library, 900 bottle wine room, mudroom, backstairs and attached heated three-car garage. Luxurious primary suite with fireplace, spa bath with steam shower and radiant floors, dressing room plus four en-suite bedrooms comprise second floor. The walk-out lower level offers flexible space for a playroom, gym, game room, and guest suite with outdoor access to a level lawn.

Step back in time with this 1790 colonial farmhouse situated on almost 2 picturesque acres of land providing a serene and private retreat. This 4 bedroom, 3 bathroom home features wide plank hardwood floors throughout and a vintage kitchen boasting copper countertops and an antique stove. There is a first floor primary suite along with a second floor primary suite. Update to your standards or rebuild up to a 7448 square foot home.

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

Large, Light, Bright Updted 2,708sf 4BR, 2.5B Home w/HrdWd Thruout in Flrs in DR w/Pict. Wndow, LR w/Pict. Wndow & Fpl, the Upper Hall & 4BRs. Grassy, level yrd w/back-yrd rock gardn. Lg. Deck off updated EIK w/Granit Countrs, Lots of Storage, Newish Electric Double (2) Wall Ovens & 36'' Rangemaster glass cooktop, 42'' Sub-Zro Refrig./Freezer. FR w/1/2-Bath & Sliders to Level Lg. Slate Patio w/back yrd. Lndry Rm off FR-w/Newish Washer, Elect. Dryer & Utility Sink. 2-Zone Heat & A/C. 2-Car Gar. w/Elec. Drs. Storage Off Garage & in 2 Attics. NEW in Basement: OilTank, Electrical Panel & Meter + CT Basement System Water Proofing System. Easy commute to Westchester Airport, NYC, White Plains, Rye, & CT areas of Glenville, Greenwich, Stamford, Etc. Close to public/private schools & Merritt Pkwy.

Discover the epitome of luxurious living in Greenwich's gated community with this sensational new construction opportunity. This 5,000 square-foot masterpiece, complete with a 2-car garage and a pool, offers unparalleled customization, allowing you to mold the floor plan and finishes to your exact desires. The heart of this home is its open living spaces and gourmet kitchen, ideal for entertaining, while the spacious bedrooms and primary retreat provide a peaceful sanctuary. With the lower level offering endless potential, this residence promises the epitome of comfort, style, and prestige in one of Greenwich's most sought-after locations. Secure your future in this gated haven, where your dream home becomes a reality. Buyers, please note this is a to be built listing yet to be constructed. All renderings and plans, including the proposed one listed would remain subject to approval by the HOA.

Welcome to this exquisite 5-bedroom, 4-bathroom home, boasting 4,332 sq/ft of sophisticated living space, nestled directly on the serene banks of what the homeowners affectionately refer to as ''Serenity Pond.'' This magnificent residence offers breathtaking pond views from most rooms, creating a tranquil backdrop to everyday life. The spacious eat-in kitchen is a culinary enthusiast's dream, with ample room for dining and entertaining. Adjacent, the inviting living room beckons with a cozy fireplace and elegant French doors, blending traditional charm with modern comfort, all while offering sweeping views of the water. Enjoy the peaceful ambiance of the Pond with a variety of activities right at your doorstep. Whether you fancy a quiet morning of fishing or birdwatching, a playful afternoon of kayaking, or simply relishing a calming evening breeze off the water, this home is your gateway to a life of relaxation and recreation. All bedrooms are generously sized, with the primary suite providing a luxurious retreat, where one can soak in the stunning scenery and the tranquil vibes of the pond. The additional bedrooms and baths are thoughtfully designed to accommodate both family and guests with utmost comfort. Immerse yourself in the unparalleled serenity and beauty of this private, yet close to town, waterside gem. The harmonious connection between the elegant interiors and the pristine outdoor environment makes this property a rare find.

Welcome to this extraordinary and truly one-of-a-kind property in sought-after Greenwich. Boasting 19,096 sq ft, 7 bedrooms, and 8.4 bathrooms, this residence offers abundant space and luxury. Nestled in prestigious Mid Country Greenwich on a 7.05-acre lot, privacy and exclusivity are guaranteed. What sets this property apart is the unique and unparalleled building opportunity it presents. Whether you choose to renovate the existing home to further enhance its grandeur or embark on creating your dream estate from scratch, the possibilities are truly limitless. The lush greenery creates a serene atmosphere. Don't miss this exceptional opportunity. Seize this once-in-a-lifetime chance to own a truly extraordinary residence in Greenwich. * Sold As Is

Stylish English Manor situated on 5.38 mature landscaped acres, nestled on a private mid-country lane. Thoughtfully restored and updated by current Owners offering six bedrooms and a wealth of amenities including pool, pool house, terraced tennis court crafted for tennis legend Ivan Lendl, charming guest cottage, and lush gardens. Inside, the home exudes understated elegance, combining extraordinary original 1932 architectural details with today's modern design/amenities. The grand formal rooms feature tall ceilings and exquisite moldings while the handsome study showcases a gorgeous tracery ceiling. The expansive chef's kitchen, complete with an adjacent breakfast room featuring parquet floors, flows seamlessly into the family room, where arched, leaded French doors provide access to the wisteria covered loggiaa true highlight of the main level. The second floor is dedicated to luxury living, with a sumptuous primary suite that includes a sitting room, fireplace, dual baths with dressing rooms and closets. Five en-suite sun-filled bedrooms are steps away accessible via front or back stairway. Downstairs, the walk out lower level has a spacious family room with a bar and abundant storage opening to a reflection pool and fields.

Truly unique 19 Acre Estate in the heart of mid country! Prepared to be captivated by this custom built masterpiece of design and craftsmanship. Completed in 2009, and offered to the market for the first time since completion, 97 Pecksland has an unrivaled combination of lot size, quality and privacy. Enter through the grand gated entrance and dramatic driveway to the elevated main house on the primary lot of 8.71 acres, with 2 further sep parcels of 5.3 and 5.13 acres for a total of 19.14 acres in the 2 acre zone. A substantial amount of mature trees balance wide open park like spaces with lawns to the front and rear of the main home. Classically designed to show a high degree of architectural integrity and balance. The Grand entry foyer with double staircase set the tone for the living spaces within. Large informal and formal spaces blend for an ideal venue for large scale entertaining, both inside and out. First floor features an oversized living room / bar area, multiple office spaces, guest suite, dining room, kitchen / fam room and kennel room for 3 large dogs. 3 car garage off the mudroom along with 3 car port cochere for day to day parking. A car collectors dream awaits in the lower level with further parking for over 30 cars. Lower level also features a generous wine cellar, tasting room and golf sim. A huge master suite with terrace overlooking the rear yard, master sitting room and multiple bathrooms and walk in closets. 6 further fam / guest suites and large

A timeless Connecticut Compound in mid-country Greenwich custom designed and built by a coveted team. Resting on 4.7 private level acres with a two bedroom guest house and barn/accessory garage. The sun-filled stylish interior features 10+foot ceilings, grand front-to-back entrance hall, refined living and dining rooms; large handsome library and five inviting fireplaces all with bespoke finishes. The gourmet kitchen and breakfast room seamlessly connect to three exposure family room perfect for gatherings. Five en suite bedrooms including primary suite with spacious terrace, sitting room and double walk-in closets and luxurious baths. Third floor space is open and bright for versatile use. The exceptional lower level has multiple recreation rooms, a wine cellar, potential media room, and space for arts & crafts. Outdoor spaces offer all the amenities to enjoy the seasons; pool, spa, fire pit, expansive lawns and combination of open & covered spaces for entertainment and relaxation. The guest cottage, fronted behind an old world stone wall, has a charming covered front porch and it's own driveway entrance. For driving enthusiasts there is garaging for 5 cars. A unique opportunity on a lovely country road close to schools and parks, 45 minutes to NYC.

The perfect condo alternative in the perfect location! Renovated ranch located on wonderful Glenville cul-de-sac near NY border. Warm and welcoming light-filled living room with gas fireplace opens into the updated kitchen with spacious eat-in area. Two comfortable bedrooms (one with queen-size Murphy bed), newer bath and cozy front foyer complete the main level. Hardwood floors throughout and central AC. Full basement with workbench, plenty of storage and access to back yard. Brick patio leads to carport with new roof and pretty, private low-maintenance yard with shed. Includes the trifecta: city gas/city water/city sewer. Also includes architectural plans for expansion. Convenient location close to shops, restaurants and easy access to Merritt Parkway. Single floor living at its best! Shed sold "as is."

Handsome custom stick-built colonial home boasting beautiful fieldstone detailing and a gracious front porch overlooking a landscaped island at the end of a cul-de-sac. The deep, private backyard is complemented by two stone patios, one bluestone and one Colorado sandstone, and gorgeous hand-stacked stone walls. Special features include four full baths, one which is adjacent to a first-floor bedroom, and another of which adds flexibility to the bright, finished lower level, with full-sized windows, perfect for exercise studio, hangout haven, au pair or guest suite. Two wood-burning fireplaces add coziness to the primary bedroom and living room. Generous and varied expansion possibilities!

Elegant country estate w/modern enhancements offering 4 BR's, 4 1/2 baths, set on 3.69 acres. Gated entrance leads to this unique home accented by specialty stone, hardwood flooring, substantial millwork, period details & flexible floorplan conducive for both formal & informal gatherings. Gourmet eat-in Kitchen and Family room w/walls of glass overlooking meticulous grounds. Enjoy time outdoors under the wisteria covered pergola, swimming in the saltwater pool, playing tennis or basketball day or night under lights, or perfecting your golf on a 3- tee practice hole and bunker complex. Quiet idyllic location 1 mile from the Greenwich border w/easy access to schools, clubs, shopping, stables & riding trails. Tranquility awaits you at ''Cedar Ridge Farm'', a timeless country compound.

Nestled on a tranquil private road, this magnificent stately colonial home offers a perfect blend of elegance and comfort. The residence boasts an abundance of natural sunlight that fills the grand foyer entrance. The main floor features 10-foot ceilings adorned with crown molding. The living room provides an inviting ambiance with a cozy gas fireplace, creating a warm and welcoming atmosphere. Adjacent to the living room is a dining room that opens up to a private deck, perfect for intimate gatherings or alfresco dining. The chef's dream kitchen features a large island with a charming farmhouse sink, granite countertops, and newer top-of-the-line stainless steel appliances. The family room is a haven for relaxation, complete with a captivating wood-burning fireplace and access to French doors leading to an expansive deck and a screened porch. This outdoor retreat offers a serene sanctuary for enjoying nature with rare specimen plantings throughout the property. The primary suite is an oasis of serenity, featuring a gas fireplace, a sitting and reading area, and deluxe his and hers walk-in closets. The primary bathroom is a spa-like haven with a walk-in shower, a jetted tub, and double sinks. A private balcony attached to the primary suite provides a secluded outdoor space for peaceful moments. Expansive bonus room to customize for endless possibilities. The lower level of the home is thoughtfully finished, offering a walkout feature and a full bath for versatility.

Welcome to an extraordinary home that offers a perfect fusion of privacy and panoramic vistas, masterfully sited adjacent to the 17th fairway of The Burning Tree Country Club in Greenwich, Connecticut. As you step into the living room, you will be captivated by the dramatic double-height ceiling, anchored by a magnificent two-story stone fireplace and windows that illuminate the space with natural light and frame the breathtaking views of the golf course. The library and formal dining room flank the living room, each with glass doors that reveal large, private decks and stunning views. The kitchen seamlessly flows into the family room, where another fireplace, complemented by a cozy breakfast room, adds warmth and character. Wood floors and exquisite paneling underscore the home's sophisticated aesthetic and attention to detail. The primary bedroom suite, facing the golf course, features a spacious walk-in closet and a beautifully appointed bath, offering a private retreat for the homeowner. With three additional bedrooms, two bathrooms, and a substantial lower-level playroom, this home can accommodate family and guests alike. The playroom, complete with a wet bar and open doors to the outdoors, provides the perfect setting for entertainment and leisure.

Nestled on the cusp of Stamford, CT, and the coveted Greenwich border, this Mid-Century Modern masterpiece offers a unique blend of architectural charm and natural beauty. Overlooking a serene spring-fed pond, and adjacent bird sanctuary 386 June Road promises a lifestyle that is both elegant and harmonious with nature. Sited on over 4 acres of lush green, renovated, as you enter the foyer prepare to be captivated. The picture window beckons you with views of the pond. The living room featuring 12' ceiling and fireplace welcomes you. Dinner time will be a breeze with the Viking gas range, soapstone counters and high-end appliances, and formal dining room with 9' ceilings. The Sunroom with surrounding windows overlooks a stone patio, lush lawn and the pond. Master suite two dressing rooms and a primary white marble bath with a soaking tub. Three additional en-suite bedrooms, featuring hardwood floors throughout. The electric car charging station for your convenience at home. Centrally located and close to shopping, highways

Welcome to 853 Riverbank Road, a peaceful and serene retreat flooded with natural light and gorgeous views of the expansive property. You will enjoy the convenience and ease of one level living and the flexibility of all the extra space of your fully finished lower level offers. In addition to formal living and dining spaces, the heart of the home includes an expansive, well appointed kitchen. There is a built in desk as well as a sizable eating area with a skylite. The adjacent family room has a vaulted ceiling and beautiful fieldstone wall with fireplace. There are sliders to a large deck overlooking the tree lined property. On one side of the home you will find the primary bedroom suite with walk in closet and a spacious bath with skylite, double sink, jetted tub and separate shower. Two other guest bedrooms and another full bath are nearby. On the opposite end of the home is another spacious bedroom with an adjacent full bath - great for a home office, guests or an au pair. The lower level is very special. There is a game room with a full bath, a spacious rec room with 9+foot ceilings and sliders to a patio, a large guest room with sliders, a home gym as well as an additional room for storage. The crawl space contains the mechanical components including 2 new oil tanks. New driveway. Also included in the sale are the pool table, foosball table, nautilus machine, refrigerator in the lower level storage room as well as the TV in the lower level.

Antique Country Compound. One of North Stamford's historic estates. The main residence, a Country Colonial built in 1804, was renovated and expanded with nicely scaled rooms with great light. Hardwood floors, three fireplaces, period millwork and French doors add architectural interest. Located in the heart of North Stamford, 4.26 acres with gently rolling lawns, old stone walls and exceptional landscaping including towering Evergreens, Dogwood, Boxwood, Rhododendrons, Hosta, Ivy and Hydrangeas. Privately sited gunite Swimming Pool with heated Cabana. Small heated Studio with Kitchenette, Living Room and Bath. Detached Two-Car Garage with heated Storage. Easy access to Merritt Parkway, shops, restaurants and train. A wonderful opportunity!

This traditional Colonial home, nestled on a private shared drive, boasts generously sized rooms and a seamless layout ideal for modern living. As you step onto the welcoming front porch, enter this lovely home by the slate Foyer which leads into the spacious Living Room adorned with a wall of windows, seamlessly flowing into the formal Dining Room and Eat-In Kitchen featuring granite countertops. Adjacent to the kitchen, the Family Room, complete with a brick Fireplace, opens onto an airy screened porch overlooking the serene rear yard. Ascending to the second floor, you'll discover the inviting Primary Bedroom offering a Walk-In Closet and Full Bath, alongside three additional comfortably sized Bedrooms and a refreshed Hall Full Bath. The Lower Level adds versatility with a newly carpeted Playroom, storage room, and mechanical room boasting a brand new boiler, with convenient walk-out access to the yard. Throughout most of both main and upper levels, hardwood floors exude timeless charm, while the main level Laundry/Powder Room adds convenience. Enjoy the comfort of Central Air and the practicality of an oversized 2 Car Garage, conveniently accessible from the main level, completing this inviting Colonial home.