Pleasantville NY Real Estate & Homes for Sale

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

A gracious Colonial prominently positioned in the coveted Mid-Country enclave of Burning Tree, provides for spacious living in a country setting. Bay windows, skylights and French doors fill the interior with natural light and complement the well-scaled proportions. The main level offers versatile living spaces with an expansive chef's kitchen flowing to elegant formal rooms and private wood paneled office. Second floor features a primary suite with a spa-like bathroom and walk-in closet; as well as three additional bedrooms and a spacious full bath. Fifth bedroom, office/bedroom, gym and a full bath on the third level offering lots of flexibility for various lifestyles. Other features include a 3,000 bottle wine cellar, expansive playroom and attached two car garage on the lower level. The highlight is the gorgeous, sun-filled family room with cathedral ceiling seamlessly connecting to the wrap-around deck and Zen-like pool - a secluded retreat perfect for summer entertaining.

Welcome to the newest offering by luxury custom builders, Ritzzo Development. This 8K SF+ 2024 smart home will be ready for move-in early 2025. 3 exquisitely finished floors with extra height ceilings throughout boast 6 en-suite bedrooms plus 2 powder rooms. Custom kitchen with Subzero/Wolf Appliances, 9' island and breakfast area. Spectacular indoor / outdoor living is designed to appreciate the level 2.16 private acres with 2 sets of french doors opening to the pool, terrace with outdoor kitchen, firepit and loggia with indoor/outdoor bar. Venetian Plaster + clapboard exterior with slate composite roof, Pella windows and doors, buried electric, 400 amp service and generator are a few of the details that make this house stand out. See video for similar interiors.

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!

Nestled at the end of a cul-de-sac in the coveted Calhoun Association lined with significant and historic homes, close to town is this 5 bedroom, renovated colonial tastefully appointed with a coastal, cottage design. The open layout and flow are perfect for enjoying a casual lifestyle that extends to the outdoor spaces. The heart of the home is the updated kitchen with high-end stainless steel appliances and granite countertops/island with abundant seating. Flanking the kitchen are two family spaces, the cozy den with fireplace and the stunning family room surrounded by floor to celling windows offering views of the exceptional grounds. Upstairs is the primary suite with a luxury Carrera marble bath, and a very large walk-in closet. There are four additional bedrooms and 3 baths including a separate nanny/in-law suite with kitchenette access through the custom mud room room and up the back stairs. The one acre tranquil and parklike property has two stone terraces, verdant lawns, stone walls, perennial gardens, mature plantings, treehouse and hot tub, feels miles from town and yet is just minutes from all town amenities and public and private schools. Truly an enchanting property with a unique combination of privacy and convenience, all within a prestige and friendly neighborhood. Expansion possibilities.

Doubling Lane - Kaali-Nagy's newest addition to their Greenwich portfolio. This new construction to-be-built with ultra-chic interiors and amazing outdoor entertaining spaces overlooking the fabulous pool is privately set behind a gated entry on 1.55 acres of lush meadows and wide open sky, Spanning an impressive 9,500+ square feet, the interiors effortlessly blend timeless elements with modern details, featuring custom millwork and finishes that set a new standard of luxury. With lofty 10-foot ceilings and white oak floors, the main level dazzles with its spacious design. Here, you'll find an incredible kitchen that gracefully opens into a two-story great room, harmoniously connected to covered terraces. Formal rooms blend seamlessly into casual spaces filled with natural light. The study with a fireplace, is set peacefully to the side - an ideal remote work space. Six generously proportioned en-suite bedrooms and a stunning primary wing with fireplace, luxurious dressing room, and spa-like bath for relaxation and rejuvenation. The lower level offers an expansive great room, along with a gym and full bath. Additional customization possible. This residence is also equipped with cutting-edge smart home technology, three-car garage and generator. Step into the exceptional lifestyle Greenwich has to offer in this coveted mid-country location, just minutes from town, train and private clubs. Anticipated completion of construction is set for 2025.

Welcome to your serene Colonial sanctuary, gracefully nestled on 2.05 lush acres. This delightful residence embodies timeless charm and offers a bright, tranquil retreat. Step inside to discover an abundance of natural light that floods the meticulously maintained interior. The main level features a double-height foyer, and a spacious formal living area perfect for entertaining or relaxing. The well-appointed kitchen boasts modern appliances, ample storage space, and extra space for informal dining. Take advantage of the generously sized office overlooking the manicured backyard. Upstairs, three generously sized bedrooms offer peaceful views of the beautiful grounds. The master suite provides a private haven with a walk-in closet and updated ensuite bathroom. An additional mid-level oversized family room adds versatility with a patio, large windows, and a cozy fireplace for leisure and entertainment. Outside, the expansive grounds invite you to unwind and enjoy nature's beauty. Meticulously cared for by the original owners, this home exudes pride of ownership at every turn. New appliances, recent upgrades, and generator are a nice bonus! Just a short distance from downtown Greenwich and Stamford, don't miss your chance to make this beautiful colonial retreat your own! Property is GREENWICH, 06831 on tax card, STAMFORD taxes and schools

This contemporary style home offers a fantastic opportunity with its 3 bedrooms, 3.5 bathrooms, vaulted & exposed beamed ceilings, two fireplaces, hardwood flooring. Open floor plan with spacious layout including a finished basement and a additional bonus room which can be used as potential office. Set on just over 1 acre, nestled in a tranquil cul-de-sac neighborhood, it provides a private retreat. The large deck & large yard is ideal for family entertaining and offers ample space for outdoor activities. With your personal touch, you can enhance this home to suit your style. Conveniently located, it offers easy access to Long Ridge Rd and the New York state line.

Nestled in the heart of North Stamford this custom-built colonial will not disappoint! Featuring a unique combination of beautiful design and thoughtful construction. Framework was done in 4"x 6" lumber, engineered wood reinforced with metal beams, foam insulation.Bathrooms feature natural marble, Kohler Cast-iron tubs, one-piece toilets & stationery/hand bidets. Full walk out basement is massive offering even more potential living space with high ceilings, fireplace and full bath.Pella casement windows fill the house with natural light, central vac ,2000-gal concrete septic tank,1000 gal in ground propane tank,6 zone sprinkler system. Additional features include CITY WATER, copper piping throughout, 100-gal high efficiency water heater & direct-vent furnace. 1st floor: Formal Living & Dining Rooms, Family Room with two story natural stone fireplace, Library/Office,rec room,kitchenette & full bath (perfect for in-law), powder room, Laundry Room,3 car garage.2nd floor has a superb Primary suite with cathedral ceiling luxurious onyx bathroom with oversize Jacuzzi tub, spa shower, bidet, wet bar, walk-in Cedar Closet seating area, private balcony, additional 3 bedrooms ,3 full bathrooms, two lofts, many closets can accommodate extended family. Kitchen has Miele S/S appliances, in island prep sink, solid cherry cabinets, granite counters & glass tile backsplash.9 foot+ ceilings on the 1st & 2nd floor Also walking distance to Larocca's Country Market!

Welcome to 25 Evergreen, a beautifully updated colonial originally built in 1924 situated on a peaceful cut-de-sac in lower mid country. This timeless residence offers a perfect blend of classic charm & modern sophistication. Boasting 5 BR/5.5BA w/ an abundance of space for family living & entertaining. Main level features a flowing floorpan with a spacious living room adorned with fireplace & French doors. Formal dining room, generously scaled family room w/ fireplace & dine in chefs kitchen showcasing marble clad countertops, butlers pantry. Upstairs primary suite offers ample closet space & balcony. 4 additional bedrooms ideal for family/guests. 3rd floor playroom/office. Landscaped yard, covered porch & flagstone patio offer endless possibilities. Minutes to schools, town and train.

Classic Mid-Century Ranch on 1.4 coveted private Saw Mill Association acres. Gracious living on one floor. In ground swimming pool with terraced flagstone patio. In addition to 3,333 square feet on main floor, lower level has 1,600 square feet of finished space. Main Floor boasts a large family room, sun room off of the pool, extra bed room/art studio, large downstairs entertainment area with wet bar and en suite for in-laws or Au Pair which opens to its own walk-out flagstone patio. New roof, New Central AC, New Hot Water Heater. All new appliances. All hard wood floors redone, new carpeting in sun room. The exterior has been freshly painted as well as the majority of the interior. Agent Related to Seller.

Welcome to Mead Farm, a tranquil and serene 26 stall horse farm in the heart of Stamford that has been home to a thriving riding program for the last 20+ years. This unique property boasts multiple exercise rings, a large arena fit for jumping, a boarders tack room as well as a lesson program tack room equipped with a bathroom, separate feed room and silo. The residents brings complete and total immersion into your equestrian lifestyle, 3 bedrooms and 2 bathrooms, with a beautiful fire-placed sunroom, step out onto the patio and enjoy your morning coffee pasture side with your horses, or sit on one of multiple balconies and watch your loved ones ride with views of the entire property. Another unique feature of this farm is its location directly on the Greenwich Trail Network, tack up and ride out without having to trailer your horses! Mead farm is the perfect place to slow down and reconnect with nature. Come see everything mead farm has to offer. The lesson program and horses are available to convey.

Welcome to 188 Mountain Wood Road, a charming 5 bed 3.5 bath home on a tree-lined cul-de-sac in North Stamford, CT. This beautiful residence spans an impressive 4795 square feet, offering ample space for comfortable living and entertaining. As you step inside, you'll be greeted by a bright, airy living space featuring large windows that flood the home with natural light. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a warm and inviting atmosphere for gatherings with loved ones. The eat-in kitchen with an island boasts modern appliances, plenty of counter space, and stylish cabinetry. Whether you're whipping up a quick breakfast or preparing a gourmet feast, this kitchen has everything you need. The primary bedroom is a serene retreat, complete with a balcony, a walk-in closet, and a spa-like en-suite bathroom. Four additional bedrooms provide versatility for guests, home offices, or hobby rooms, ensuring that everyone has their own private space. Outside, the professionally landscaped, expansive yard offers a peaceful oasis for relaxation and outdoor activities. Enjoy al-fresco dining on the patio, or simply unwind in the tranquility of the lush surroundings. Downstairs, a rec room provides additional space for entertaining, and the multiple private decks offer stunning views and outdoor enjoyment. The property also features a fully equipped pool house, pool, and jacuzzi, perfect for hosting unforgettable gatherings.

Welcome to 1 Stepping Stone Lane, a harmonious blend of gracious architecture and mature landscaping, where every detail has been thoughtfully crafted to create a sanctuary of natural beauty. The open-concept living area boasts soaring ceilings and large windows that flood the space with natural light, offering panoramic views of the wooded landscape. The large welcoming marble foyer with an elegant staircase, leads to an open-concept living area with high ceilings and large windows that flood the space with natural morning and afternoon light. The white kitchen with black granite counter tops, opens to the rear patio, ready for al fresco dining. On one side are the laundry room, pantry and powder room. The family room with its bar and natural gas fireplace, adjoins the kitchen. Off the foyer, is the long gallery hallway leading to two large master bedrooms with en suite bathrooms and walk in closets. The bedrooms with many large windows, allow for light and garden views. The second floor has two additional extra large bedrooms with their own brand new marble bathrooms. The hallway, with three walk in closets, affords plentiful storage. The picture window study sits between the two bedrooms.. The house has natural hardwood flooring throughout. The 2030 sq ft basement, with its high ceilings, awaits your transformation! Outside the landscaping with stone patio and fenced-in backyard, boasts many specimen plantings and perennials.The house located in a tree lined cul

Welcome to La Gentilhommiere, a Fairfield County gem, embodying the epitome of architectural finesse, now open for those seeking unparalleled luxury. Inspired by the Chateau de Givenchy le-Noble, this limestone masterpiece seamlessly blends European elegance with modern comfort. Enter through the gates, flanked by mature linden trees, into a formal motor court, where each sense is awakened by the beauty around. From the flowering trees to the melody of birdsong, every detail resonates with opulence. This is a residence, a sanctuary, a work of art. The materials used to create this treasure are authentically French: centuries-old beams, 18th century parquet de Versailles floors, Remy Garnier hardware, even the La Cornue range. In the tradition of so many period manor homes, the main residence's four ensuite bedrooms are all located on the arrival level of the home, with the public rooms located on the upper level. Engage in quiet contemplation in the parlor or library, indulge in lively discussions in the dining room, or delight in culinary pursuits in the Smallbone kitchen, adorned with two limestone sinks. Natural light floods every space, framing picturesque views of the landscape. Step outside to an enchanting outdoor oasis, complete with a guest house, sparkling pool, and pool house boasting a gas fireplace, magnificent bath and surround sound home theater. Despite its tranquil ambiance, this estate remains conveniently close to Manhattan.

Parklike,- 1.27 acres, the Greenwich 4+Den-bedroom Colonial is nestled down a private drive off Edgewood just a blocks from downtown. This home is an entertainer's delight with an expansive sun-filled living room, an open kitchen w/ access to terrace & in-ground pool. Finished lower level includes additional 1,690 square feet w/ home theater, recreation room, home office, & optional den/au-pair in-law options pus full bath. Main level flowing floorplan, tall ceilings with back-to-front foyer, 2-story living room adorned with a fireplace & French doors, formal dining room, generously sized family room with built-ins and stately study. Upstairs, the primary suite provides fireplace and sitting room, dressing suite & balcony. Additionally, there are 3 more bedrooms. Full House generator

This multi family home is an ideal entry point for investors and home owners with two manageable units. As an investment; a 1 bed and 2 bed unit always in high demand. Light updating and ready to increase to total market rents of $5000/m. As a ''house hack''; live in the one bed unit and rent out the second unit for $3000/m. As a single family; reopen a sheetrocked door to make functional 3 bed/3 bath with curb appeal and large level yard. Whatever the use, it's in a great home in a great location. Unit 2 a 2 bed 2 bath unit not shown in photos. Great layout and space. Subject to probate approval.

This multi family home is an ideal entry point for investors and home owners with two manageable units. As an investment; a 1 bed and 2 bed unit always in high demand. Light updating and ready to increase to total market rents of $5000/m. As a ''house hack''; live in the one bed unit and rent out the second unit for $3000/m. As a single family; reopen a sheetrocked door to make functional 3 bed/3 bath with curb appeal and large level yard. Whatever the use, it's in a great home in a great location. Unit 2 a 2 bed 2 bath unit not shown in photos. Great layout and space. Subject to probate approval.

Charming end unit walk-in one level condo with amazing light and outdoor terrace. Freshly painted; hardwood floors throughout; updated Kitchen with s/s appliances and granite counters; updated bath, NEW washer/dryer in unit. Large storage closet and area for home office. Assigned parking and separate storage space (outside access through back of bldg). Common picnic area with BBQ. This lovely home is turn key and move in ready. Great location convenient to Greenwich Avenue shops and endless dining choices, Metro North, I-95 and the Merritt Parkway. NEW roof November 2023.

New to market! Prepare to be captivated by views of the Greenwich skyline and Long Island Sound in this 3-bedroom condo flooded with natural light. Seconds from Greenwich Ave, the Greenwich Lodge is an elegantly preserved historic landmark with secure entry and elevator for its residents. First of its kind with in-unit washer/dryer, this condo with northern and southern exposures offers extraordinary finishes with an antique cast-iron mantel, marble foyer, hardwood floors throughout, expanded walk-in closets in primary bedroom, and an updated kitchen with double ovens and brand new dishwasher. There is an on-site superintendent, dedicated storage space and rooftop deck with breathtaking views. Close to shops, restaurants, & train from your private oasis in the heart of downtown Greenwich.

Welcome to this captivating 1930 vintage colonial boasting nearly 4,000 sf of timeless charm & modern amenities across 3 lvls of living space. Situated on 2.86 acres of private & picturesque land, this exceptional property features 5+ BRs & 3.5 baths, perfect for comfortable living & entertaining. The large front porch - an ideal spot for enjoying the surroundings - sets the scene & warmly welcomes you into the oversized LR, featuring a beautiful stone fireplace. The spacious DR is adorned w/ corner cabinets, wainscoting & sliders to a deck overlooking the expansive grounds, incl scenic water views. The light filled kitchen incl an island, s/s appls, pantry, & a convenient half bath nearby. Completing the 1st flr is the show-stopping library, w/cherry built-ins, a 2nd stone fireplace, & add'l front porch access. The 2nd flr offers comfort & convenience w/a corner primary en-suite, 3 add'l BRs, a full bath & laundry rm. The 3rd flr has flex living options w/ 3 add'l rms, a full bath, large cedar closet & ample storage space. LL features exterior access & a large storage/canning room. Outside, embrace country living w/ a charming chicken coop & ample space for gardening & outdoor activities. The 2-car garage w/200-amp service provides a perfect workspace for projects & hobbies. NEW: roof w/copper flashing, well equip, & water heater. Hardwood floors throughout, freshly painted inside & out,& minutes to everything - don't miss the opportunity to make this timeless home your own!

Welcome to this tranquil 5 bedroom haven on a quiet cul-de-sac, blending comfort, convenience, and luxury. With two primary suites, this home caters to your every need. A dream worthy walk-in closet, and lavish ensuite bathroom define the first floor suite. The second floor suite boasts cathedral ceilings and equal opulence. This residence is an entertainer's delight with an expansive sun filled living room, open concept kitchen, and deck overlooking a beautifully landscaped backyard. The lower level offers a 10+ft ceiling entertainment space, walk-out access to a pond, a well appointed kitchenette, and a stylish bathroom, perfect for hosting and relaxation. A thoughtfully designed office space on the lower level ensures a quiet and productive environment. Conveniently located near schools, trains, and highways, this home meets your daily commute and educational needs. Enjoy the convenience of nearby amenities while savoring the peace and quiet of your private retreat.

Absolutely stunning! 156 Old Church Road underwent a complete gut renovation in 2017, transforming it into a high-end masterpiece. The quality is evident throughout, with meticulous attention to detail. Boasting 5 bedrooms, 6.1 bathrooms, finished lower level, and 3rd floor, this home epitomizes luxury living. Each space is a testament to bespoke craftsmanship, featuring all new and custom kitchen and bathrooms, millwork, fireplaces, sauna, bar, etc.! The beautiful patio, complete with a built-in stone fire pit, seamlessly extends the living area outdoors, creating an incredible indoor-outdoor living experience. With an open concept floor plan designed for family comfort, this residence exudes both sophistication and warmth, making it truly a unique gem.

Stunning 4 bedroom ranch in coveted Stamford neighborhood. Enter into the large welcoming foyer that opens to the sunken living room with fireplace and tons of natural light. Expansive kitchen with breakfast bar, eating nook and plenty of storage space. Two additional rooms perfect for work from home, library, den or guest bedroom. Main bedrooms separate from the rest of the house down a hall to the primary suite with walk-in closets and luxurious full bath. Lower level features a finished family/rec room, laundry and tons of storage. Walk out from the dining room or kitchen to the patio and huge backyard. Quiet location, great neighborhood with easy proximity to downtown and commute to elsewhere. Come see this house today, it won't last!