Pleasantville NY Real Estate & Homes for Sale

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.

Elegantly renovated 6 bed, 6.2 bath Georgian Colonial w/stunning finishes & custom millwork on 4+ acres bordering the Greenwich Audubon 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 & also 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 this distinguished property.

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.

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.

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

New construction on quiet lane set high on 2 acres off Riversville w 10' ceilings, spectacular natural light and 4 levels of living. Main house boasts 7 ensuite dbl bedrooms & 10 baths plus additional modern guest house with bed, bath ,laundry + 13' ceiling in fam rm w kitchenette. Spectacular kitchen / family rm w dbl islands, Viking , Subzero appliances & FP opens out to terrace + htd pool. First floor w sunlit LR w fp & DR Incls ensuite DBR, office/homework room & library. Spacious primary suite w 2 bathrooms, large walk in closets + separate sitting room / office. 7th bed in walkout LL with rooms for exercise, home theatre, wine + playroom. 3rd floor playroom + office spaces w full bath. Open floor plan allows for flexible living spaces throughout.Builder offering one year builders warranty.

Welcome to 75 Bowman, a beautifully expanded ranch/split-level home nestled in the highly desirable King Merritt Association. This thoughtfully designed residence offers a spacious, sun-filled layout that effortlessly blends relaxation and entertainment. With primary suites on both the first and second floors, you have the flexibility to choose the space that best fits your needs. The family room and entertainment kitchen, with sliding doors leading to the pool, create the perfect setting for gatherings. Outside, the yard and inviting pool provide a serene backdrop for hosting or unwinding. Located in a vibrant community with convenient access to local amenities, this home offers an exceptional blend of comfort and lifestyle. Don't miss your chance to make 75 Bowman your private retreat!

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.

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.

A true Greenwich classic nestled on 4.14 private, level acres, this stunning center-hall Georgian colonial with a delightful guest house embodies elegance and comfort. Setback for ultimate privacy, this meticulously updated and maintained home strikes the perfect balance between classic architecture and contemporary upgrades. Step into the grand front-to-back foyer that flows seamlessly into the formal dining room, living room, private den/office, and inviting family room. French doors open to a serene rear bluestone patio. The gourmet kitchen features a Wolf gas range, a Sub-Zero refrigerator, two additional frig/freezer drawers, two dishwashers, a center island, a breakfast counter, and a sunlit dining area with direct access to the family room and steps leading outdoors. A main-floor ensuite bedroom offers versatility as a guest suite, additional office, or playroom. Upstairs, the primary suite boasts a tray ceiling, double walk-in closets, a luxurious bath, and a private sitting room. Three additional ensuite bedrooms feature built-ins and walk-in closets, while a spacious family room with an adjacent bedroom creates the perfect guest suite. Convenient back stairs provide easy access to the kitchen and mudroom. The lower level includes a playroom with a custom mahogany wet bar, a half bath, and a gym, adding approximately 1,400 additional square feet. A fabulous one-bedroom guest house with a covered porch and an oversized two-car garage offers endless possibilities.

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.

Anchored into a hillside, this three level Mid Century Marvel is proof that two things can be true at the same time, as it both blends into, and stands out in, the surrounding natural habitat of native plants and massive rocks sculpted by a long-forgotten glacier. This property in North Greenwich is truly one of a kind, designed and built by the visionary artist and architect Norman Hoberman, it is filled with light and creativity to stimulate the mind and soul. With 4,670 SF set on 5.6 acres, the open floor plan showcases the outdoors, and can work for almost every lifestyle, both personal and professional.Enjoy the radiant-heated slate floors, floor-to-ceiling glass windows, and a brick fireplace in the living room. The bright, eat-in kitchen has been lovingly restored, completed with new appliances and opens to gardens with steps to a brick patio ideal for gatherings. Upstairs, you'll find two wood-burning cast-iron vintage stoves, three bedrooms with freshly refinished oak floors, two large skylights, ample built-in storage, two full bathrooms and a large family room. Great potential is found in the two large (formerly artist studios) for a home office with separate entrance, creative hobbies, health activities, in-law or au-pair living space, plus a third-level home office drenched in natural light. Updates include roof, generator, flooring, freshly painted interior and new appliances.

Prominently sited on a private Mid-Country lane, this gated stone manor offers a rare blend of timeless elegance and resort-style amenities. Set on 2 private acres with 10,000+ sf of beautifully designed living space, this estate stands out for its highly convenient secluded setting. The breathtaking grounds, designed by Edmund Hollander (AD 100), feature mature specimen trees, lush plantings, and a landscape that evolves with the changing seasons. A 20' x 40' pool with covered pavilion, granite fireplace, and outdoor wet bar serve as the centerpiece of the outdoor experience. Adjacent, a built-in Viking grill and flagstone patio provide the perfect space for alfresco dining. Built in 2006, the custom home with oversized 3 car garage is flooded with natural light via Marvin windows and doors and soaring 10' ceilings. Inside, the double-height front-to-back entrance hall leads to a generous kitchen and open, double-height family room with a limestone fireplace, seamlessly connected to the private backyard. The living room and library each feature elegant stone fireplaces, creating warm and inviting gathering spaces. The chef's kitchen with granite countertops is outfitted with a Sub-Zero refrigerator, Viking Professional range, and two Miele dishwashers, and a wine fridge for entertaining. Rounding off the first floor is a bedroom with a full bath just off the kitchen, perfect for guests.

Discover this exquisite retreat that seamlessly blends luxury and nature, designed with both comfort and style in mind. With 4 spacious bedrooms plus Office/Den, 3.1 bathrooms, this 3750 sq ft of sleek, bright living space makes for the perfect forever home or weekend hideaway. This "TO BE BUILT" home is located in a prestigious enclave of fine residences in North Stamford, on a quiet cul-de-sac. Nestled on 2 lush acres offering a bucolic natural setting with a picturesque seasonal views of the reservoir and plenty of privacy. It features gorgeous living spaces with an array of luxury amenities to personalize your home. The 1st floor features a welcoming entry foyer, 10' high ceilings, open-plan chef's kitchen with center island and breakfast nook, walk-in butlers pantry, dining and a connecting Great Room w/12' ceilings providing ample space for entertaining with easy access to the spacious covered patio and open terrace, an office/den, powder room and laundry room all on 1st floor. The Primary suite w/2 large WICs and spa-like bath, 3 addt'l BR's, 2 full baths complete the second floor. Full walkout lower level, optional upgrade at an additional cost to finish LL. This home has it all! Conveniently located near fine dining, shopping, theaters, parks, golf, hiking, beaches, and everything the vibrant City of Stamford is known for, easy access to train, airport and Hwys! Easy commute, one hour to NYC! Interior pictures are a representation only, plse see spec sheet.

Walk into the main level with an oversized living dining room, which opens to a newly renovated kitchen. The first floor also includes a newly renovated powder room. There is also a bright study/office room, in addition to an oversized family room that can also be used as a third bedroom. Upstairs, there are two bedrooms. The primary bedroom features a walk-in cedar closet. The second bedroom has two closets. The oversized laundry room is great for additional storage. The full bathroom is on the same level. As an added bonus there is a ground level accessible 2-3 bedrooms with laundry and a bathroom. There is lots of natural light and was previously used and approved as an ADU accessory apartment. There is lots of parking and storage space along with a wraparound porch/deck

Virtually New Modern Home, expertly renovated by Frattaroli Construction Group. This stunning residence is a perfect blend of contemporary elegance and timeless classic design. It boasts expansive living areas bathed in natural light, creating an inviting atmosphere for both relaxation and entertaining. The heart of the home is the gourmet kitchen, featuring high-end Thermador appliances. A true showcase of sophisticated design! The primary suite featuring vaulted ceilings that add an airy elegance. The luxurious bathroom with spa-like amenities, including a soaking tub. The third-floor en-suite serves as an ideal guest suite, offering comfort and privacy. A finished lower and spacious backyard, perfect for entertaining family and friends and creating lasting memories.

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 is a must see spacious Mid- Century 5 bedroom, 3 1/2 bath 3500+ 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. The house has been wired for internet and AV charging station. Two patios for gathering and hosting. Possible pool site, 6 Minutes to town

Welcome to 1187 Riverbank Rd! Space and tranquility await in this desirable N-Stamford location! Situated on 2.29 acres close to the Greenwich border. This is a fantastic home for anyone looking for ample space to spread out, yet enjoys a quiet and private setting. The home offers multiple flex spaces that would work well for a gym, movie theater, art gallery, office, play room, dance studio or whatever the heart desires. Extra large stone patio with built-in firepit and a side yard for additional space to entertain or room for a swing/play-set. The gourmet kitchen has granite countertops, double wall ovens and a built-in pizza oven. For larger gatherings, there is a spacious bonus room with hardwood flooring, high ceilings, and skylights. The living room features a beautiful fireplace, serving as a focal point. On the main floor, you will find a large primary bedroom w/ high ceilings, skylights, sliders to a balcony, and a private primary bathroom with a separate shower & jacuzzi tub. Additionally, there are two more bedrooms and another full bathroom on this main floor. The lower level family/flex room offers a stone fireplace with wood-burning stove insert, bedroom with a private bathroom, an office, a laundry room, a full bathroom and an entry/mud room. Both a main level and lower level garage with interior access. Experience the abundant indoor/outdoor space tailored to accommodate additional cars, boats, snowmobiles, RVs, & the potential for an in-ground pool

Move in late summer 2025 to this Mid Country New Construction smart home on 2.16 exquisite level acres will be ready for mid fall move in. 9400+ SF of finished space on 3 floors with extra height ceilings throughout. Primary suite and 4 en-suite bedrooms on 2nd floor and a 6th bedroom in the walkup lower level. Custom kitchen with Subzero/Wolf Appliances, 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 and covered porch. Clapboard exterior with slate composite roof, Pella windows and doors, buried electric, 400 amp service, elevator shaft, electric car charger and generator are a few of the details that make this house stand out. Time to customize.

This beautifully updated home offers bright, open living spaces and a serene, park-like setting. The spacious living and dining area boasts soaring vaulted ceilings, a cozy fireplace, and seamless access to an expansive deck perfect for outdoor entertaining. The recently updated kitchen shines with custom cabinetry, quartz countertops, and new stainless steel appliances. Upstairs, the primary suite features a walk-in closet and spa-like bath with a soaking tub and separate shower. Two additional bedrooms and a full bath complete the second level. A versatile first-floor office can double as a guest space or den, while the finished lower level provides endless possibilities. A two-car garage and community amenities, including a pool, tennis courts, and clubhouse, complete this home.

This charming property seamlessly blends classic elegance with modern comforts, offering an ideal sanctuary for both relaxation and entertaining. This home features newly upgraded roof, Kitchen and state of the art appliances, flooring, bathrooms, fixtures, door handles and hinges. The open layout flows effortlessly into the living room making it perfect for hosting gatherings. The in-law suite can be a private and comfortable retreat for guests or extended family members with its own amenities.

A rare offering of a unique property w/ winding river views, an expansive lawn, an in-ground pool & exquisite landscaping. A resort like atmosphere unmatched anywhere at this price. Conveniently located on a mid-North Stamford cul-de-sac you will find this classic colonial has been maintained very well. Recent updates include a newer furnace installed 2020, a newer hot water heater installed 2021 & newer air conditioners installed 2022. The main level has spacious bright rooms w/ great flow. The 2nd floor offers the primary suite w/ beautiful views, 3 additional bedrooms & hall bath along w/ an office / den. The finished lower level is the perfect recreation room, & there is also the laundry & storage. This is one of those properties that do not come on the market often.