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luxury real estate for sale Greenwich, United States (page 4)

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887 listings near Greenwich

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Contract pending
47
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House with pool Cos Cob (United States)

Picture-perfect and impeccably maintained, this stunning 5-bedroom, 3.5-bath home offers exceptional flow, generous scale, and timeless appeal in one of the area's most sought-after neighborhoods. Sun-filled interiors feature spacious living and entertaining rooms, an inviting layout, guest room and private office. The finished lower level provides excellent additional space for recreation, fitness, media, or play. Set on a spectacular level property, the private backyard is a true retreat with a sparkling pool and expansive lawn for entertaining and outdoor enjoyment. Ideally located in the coveted North Mianus and Eastern school districts and just minutes from Country Day School, this is a rare opportunity to enjoy comfort, style, and convenience in an outstanding location.

… 
$3,125,000
5bedrooms
5bathrooms
land 4,087

By Sotheby's International Realty - Greenwich Brokerage

Nearby
5

House with terrace Stamford (United States)

Experience refined luxury in this expansive Westover home, discreetly nestled at the end of a tranquil driveway just moments from schools, highways, transportation, and Stamford and Greenwich amenities. The property is enveloped by lush mature landscaping and offers access to the sprawling beauty of Mianus River Park. Designed for both grand entertaining and effortless everyday living, this move-in ready home exudes timeless sophistication. The gourmet chef's kitchen, complete with an elegant butler's pantry, flows seamlessly into gracious open-concept living spaces. French doors throughout the main level open onto an expansive west-facing deck, perfectly positioned to capture breathtaking sunset views, while a sun-drenched patio just off the kitchen creates an exceptional indoor-outdoor lifestyle. The serene main-level primary suite is a luxurious and expansive, featuring dual walk-in closets and a spa-inspired bath with a Jacuzzi tub. The second level offers four generously proportioned bedrooms, including two en-suite bedrooms and two with a shared bath. Bathed in natural light, the home also features an extraordinary walk-out lower level with a private en-suite guest suite, spacious office, and an expansive recreation room anchored by a dramatic stone fireplace. Every detail of this exceptional residence has been thoughtfully curated to offer unparalleled comfort, elegance, and privacy.

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$2,295,000
6bedrooms
5bathrooms

By Annonceur International

Nearby
50

House with garden and terrace Stamford (United States)

Offering a warm blend of 19th-cent character & modern updts, this 1860 Greek Revival Col showcases truly distinctive features. Despite its expansive 5,358sf, the home feels inviting & intimate, highlighted by rustic design elements incl brick hallways & accents. Orig rich random width pumpkin pine plank flrs recently refin 10' clgs thru-out & 5FPs. Set on 1.22 lvl acres w/specimen trees, this special property offers a peaceful, prvt setting in desirable Westover-just moments from city amenities. The orig residence, believed to be the orig area farmhse, feat a gracious LR & DR both w/FPs, Kit w/access to charming Bkfst Rm, Full Bth & unique brick hallway w/sunlit nooks ideal for reading, gardening & relaxing. An award-winning late 1960s addition recognized for architectural accuracy of design & craftsmnshp, enhances the home w/stunning FR feat a wall of blt-ins & spacious Den-both w/FPs & wonderful windows flooding the space w/natural light. Upstairs you'll find a priv & spacious PBR w/FP & en-suite Full Bth. 4 add'l BRs, 3rd Full Bth w/Laundry, & a framed space ready for an add'l bth, +a bright, airy Bonus Rm. Dramatic walls of floor-to-clg windows overlook the brick patio & beautifully landscaped grounds. The lvl, fenced yard w/mature plantings provides a serene outdoor retreat perfect for relaxation and entertaining. This wonderful home features brand new mech sys incl C/A, Furnace, Wtr Htr, Boiler & Well Purification sys.

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$1,489,000
5bedrooms
3bathrooms
land 4,937

By William Pitt Sotheby's International Realty

Nearby
30

House Cos Cob (United States)

Beautiful five-bedroom Shingle Style Home set high above the Mianus River, with views of open sky, tree tops and River valley. Spacious floor plan with eat-in gourmet kitchen open to dining room, family room with French doors to large deck and covered outdoor area. Living room lends to patio seating under pergola. Second floor you will find the primary suite with sitting room, ample closet spaces, luxury bath, and screened-in porch with hanging bed. Four addt'l bedrooms, with Jack + Jill bathrooms, round out the second floor. Bonus room on the 3rd flr. Outside you will find a putting green/turf backyard, fire pit + bball hoop. Lower level completes this home with a play space, climbing wall, zip line, as well as office space. Lower level and third floor not included in square footage.

… 
$3,800,000
4,916
5bedrooms
5bathrooms

By Annonceur International

Nearby
19

House Cos Cob (United States)

Tucked at the end of a private road in Cos Cob, this newly built (2025) Louis Contadino-designed home offers a layout rarely available in central Greenwich at this price point: sophisticated single-level main-floor living over a fully finished walk-out lower level, all on a private 0.34-acre setting. The main floor delivers four bedrooms -- three with private en-suite full baths, including a primary suite with soaking tub, double vanity, and heated floors. The chef's kitchen features Sub-Zero and Wolf appliances, custom cabinetry, marble counters and backsplash, a white oak island, and a walk-in pantry, all opening to a light-filled great room and formal dining. Wide-plank white oak flooring runs throughout. Below, a generous family room with full bath and direct yard access expands the home for guests, entertaining, or future flexibility. Approximately 3,500 square feet of finished living space in total, with available FAR for roughly 1,000 square feet of additional expansion if desired. Outside, extensive stonework frames the entry, terrace, and grounds, with four-zone HVAC and EV charging completing a thoughtful modern build. Set high above a quiet private road yet minutes from the village, train, and I-95, the property offers the privacy of an estate in a location that keeps you fully connected to Greenwich. Vision, design, and execution complete -- a finished home, ready to move into.

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$2,895,000
3,408
4bedrooms
5bathrooms

By Annonceur International

Nearby
25

House Stamford (United States)

Privately nestled on 1.76 exceptional acres in a coveted Westover setting, 450 Westover Road is a sophisticated retreat offering remarkable privacy, scale, and timeless appeal. Surrounded by mature landscaping and serene natural beauty, the property's expansive grounds create a rare sense of seclusion while remaining just moments from town, schools, and commuting routes. Sunlit interiors, expansive entertaining spaces, and oversized windows create an airy elegance throughout, while refined architectural details add warmth and character at every turn. The stunning primary suite is a true sanctuary, featuring soaring vaulted ceilings and dramatic arched windows that flood the space with natural light while overlooking the picturesque surroundings. Generously scaled bedrooms, renovated baths, and flexible living areas offer both comfort and versatility for today's lifestyle. Complementing the main residence is a separate accessory structure with rich wood interiors and entertaining space, perfectly suited as a private studio, wellness retreat, home office, or guest escape. An exceptional offering combining privacy, sophistication, and extraordinary land in one of the area's most sought-after locations.

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$1,250,000
2,499
4bedrooms
2bathrooms

By Annonceur International

Nearby
14

House with pool Cos Cob (United States)

Tucked away in the heart of Cos Cob, this spacious 3-bedroom, 2-bath home offers an incredible opportunity to enjoy convenience, comfort, and potential in one of Greenwich's most desirable neighborhoods. Featuring approximately 2,400 sq ft of living space, this 1966 built residence is ideally located within close distance to schools, shops, and metro-north for an easy commute to New York City. Inside, the home offers generously sized rooms throughout, including a large eat-in kitchen with access to the oversize deck, expansive living and dining rooms, and a substantial lower-level family room, with fireplace, perfect for entertaining, recreation or flexible living space. Step outside to enjoy the inground pool and private backyard setting - ideal for summer enjoyment. Being sold as-is, this property presents a wonderful opportunity to update, customize or simply enjoy as it is a prime Cos Cob location.

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$1,495,000
3bedrooms
2bathrooms
land 769

By Sotheby's International Realty - Greenwich Brokerage

Nearby
40

Property with pool Stamford (United States)

Modern Sophistication Meets Suburban Serenity in Westover - Tucked away on a tranquil cul-de-sac, this recently built architectural gem offers a masterclass in modern living, blending refined elegance with the vibrant energy of nearby downtown Stamford. The residence unfolds through a dramatic two-story foyer into a sun-drenched, open-concept sanctuary, where a chef-inspired kitchen-adorned with pristine white cabinetry and expansive granite surfaces-flows effortlessly into a fireside living room and adjacent sunroom with French doors leading outside. The outdoor experience is truly peerless, featuring a resort-style saltwater pool with waterfall, a professional-grade basketball/sports court, and a sprawling bluestone patio framed by artisanal rock walls and secure perimeter fencing. With a high-efficiency infrastructure, vast expansion potential in the walk-out basement, and a commute to Manhattan in under an hour, this property represents a rare opportunity to enjoy like-new luxury and a private backyard oasis without the wait.

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$1,795,000
4bedrooms
5bathrooms
land 4,452

By William Pitt Sotheby's International Realty

Nearby
23

House Cos Cob (United States)

Move right into this beautifully maintained 4-bedroom home in the heart of Cos Cob. The first floor offers a wonderful open-concept family room flowing seamlessly into the eat-in kitchen, creating the perfect space for everyday living and entertaining. A formal dining room, full bath, private office, and study complete the main level. Upstairs, you'll find four generously sized bedrooms and two full bathrooms, including access to a walk-up attic from one of the bedrooms, providing excellent storage or future expansion potential. Outside, enjoy a flat backyard and detached two-car garage. Ideally located just moments from parks, shops, restaurants, schools, and the train, this home offers the perfect combination of space, convenience, and lifestyle.

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$1,650,000
2,720
4bedrooms
3bathrooms

By Annonceur International

Nearby
41

Apartment Cos Cob (United States)

Unparalleled water views and boater's dream. Quality renovation, includes 30' boat slip, 16 units at River Landing. Channel access to Long Island Sound. Common fees include private dock. Updated eat-in kitchen w/Bosch SS appliances. Dining room features river views. Relax by the fireplace in LR or step through sliders onto your scenic deck. Primary suite w/completely updated bath, Waterworks fixtures, marble countertop, has private balcony overlooking expansive lawns and the water. Large 2d bedroom with deep closet. Potential for finishing insulated attic space for additional living space on 4th floor. Ground-level office/gym/playroom. Generous storage, community garden, storage for kayaks/boards. Oversized attached garage, 1 outdoor parking, close to train, I-95. www.115riverrd.com. Hallway powder room has also been updated with Waterworks fixtures and marble countertop. There are sidewalks from River Landing to the Greenwich Water Club, Cos Cob train station, shopping and restaurants. Square footage: entry level 645 sq.ft. (office 264, foyer 99, garage 285). 1st floor 645 sq.ft. 2nd floor 617 sq.ft.

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$1,575,000
2bedrooms
3bathrooms

By Sotheby's International Realty - Greenwich Brokerage

Nearby
50

House with garden and terrace Stamford (United States)

80 East Ridge Road - Deerfield Estate, Stamford, CT. Nestled in a prestigious North Stamford enclave, this residence sits on 1.16 landscaped acres, offering an extraordinary blend of architectural grandeur, absolute privacy, and effortless access to NYC. From the moment you arrive, the transformation is striking. 20 newly planted trees frame a re-landscaped garden - a lush sanctuary crossed by a serene private stream visible from inside the home. Step outside to 2 generous decks, a jacuzzi, a flower and vegetable garden, and an outdoor fireplace for gatherings. A four-season solarium completes this outdoor paradise. Inside, soaring ceilings, skylights, and oversized new windows flood every room with extraordinary natural light. The spectacular see-through fireplace anchors both the living room and family room, creating a warm, convivial heart to the home. The chef's kitchen features premium granite countertops, top appliances, and floor-to-ceiling sliders opening directly onto the deck. The primary suite is a true spa retreat: radiant heated flooring, an oversized walk-in shower, and double sinks. Three additional bedrooms and a fully finished basement - Murphy bed included, ideal as guest room or home office - complete the picture. 2-car garage with an EV outlet for your electric car, ample parking, full furniture package available. 5 minutes to Whole Foods and restaurants. 50 minutes to Manhattan by train or Merritt Prkwy. Turnkey. Luminous. Exceptional.

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$1,250,000
4bedrooms
4bathrooms
land 4,694

By William Pitt Sotheby's International Realty

Nearby
34

House with pool and terrace Stamford (United States)

Discover this distinctive Colonial, gracefully positioned on a quiet cul-de-sac with 2 acres of stunning natural beauty. From the moment you arrive, timeless elegance and thoughtful design welcome you home. Sun-filled grand rooms flow seamlessly throughout. The impressive living room captivates with a fireplace, gleaming hardwood floors, and a wall of windows. The gourmet kitchen is a true showpiece - granite counters, premium stainless appliances, and an oversized island perfect for entertaining. Step through French doors to your private deck and sparkling heated in-ground pool - outdoor living at its absolute finest. The primary suite is a sanctuary of its own - a private wing complete with a fireplace, personal gym, steam shower, jetted tub, and two oversized walk-in closets. Four generous upstairs bedrooms, including an en-suite second primary, accommodate family and guests beautifully. A main-level office and two powder rooms add everyday convenience. The finished lower level offers a mud room playroom, cedar closet, and exceptional storage - ideal for hobbies or a private workspace. A whole-house generator and EV charging hookup deliver the ultimate in modern luxury and peace of mind. Exceptional space. Exquisite details. Extraordinary value. This is the one you've been waiting for.

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$1,889,000
5bedrooms
5bathrooms
land 8,094

By William Pitt Sotheby's International Realty

Nearby
Contract pending
40

Property with pool and garden Stamford (United States)

Exceptional custom-built 4 to 5 bedroom Colonial in desirable North Stamford! This impressive 4,644-square-foot residence welcomes you with a dramatic two-story entry hall and offers sophisticated living on a beautifully landscaped 1.1-acre lot. Four generous bedrooms and four full baths plus one half bath provide ample space for family and guests. A versatile bonus in-law suite over the three-car garage features convenient back stair access, perfect for multi-generational living or au pair accommodations. Plus 2200 square foot lower level with high ceilings is just waiting to be finished. Outdoor living is a dream with a level yard, expansive wood deck and patio with a heated in-ground pool-ideal for entertaining throughout the seasons. The prime North Stamford location offers tranquility and privacy while remaining just minutes from the Merritt Parkway for easy commuting. Experience the perfect balance of luxury, functionality, and location in this distinguished home.

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$1,695,000
4bedrooms
5bathrooms
land 4,452

By William Pitt Sotheby's International Realty

Nearby
Contract pending
16

Apartment with terrace Old Greenwich (United States)

Invest with a tenant in place! This sun-filled studio offers efficient, low-maintenance living in a prime, convenient location just minutes from Greenwich Point Beach, Binney Park, shopping, dining, and public transportation. The unit includes a private balcony - a valued feature for outdoor enjoyment, as well as on site parking. It also presents future potential for first-time buyers or downsizers.

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$295,000
1bathroom

By Sotheby's International Realty - Greenwich Brokerage

Nearby
Contract pending
44

Property with pool and garden Rye Brook (United States)

Experience luxury and easy effortless in this spectacular, masterfully updated home located in the highly desirable BelleFair community! Featuring a welcoming front porch and a dramatic two-story entry, this home shines with refinished hardwood floors across the first level and stairs. A stunning kitchen renovation boasts pristine marble countertops and ultra-luxury appliances (Sub-Zero fridge/wine cooler, Wolf cooktop/oven/microwave, Cove dishwasher). The sophisticated layout offers a seamless flow into the livingroom area, complete with a fireplace and soaring high ceilings. The main floor also features a convenient powder room and a sought-after first-floor primary suite. Renovated bathrooms on both floors are equipped with luxury Toto bidet toilets. The second floor offers 2 spacious bedrooms and a large livingroom/possible 4th bedroom. The fully finished walk-out lower level is an entertainer's dream with elegant marble floors, custom built-ins, a full bath, and a separate entrance. Outside, relax on the beautifully renovated deck. Enjoy total peace of mind with a newer roof (2024). Parking is incredibly convenient with a 2-car attached garage, 2-car driveway, and nearby guest parking. Experience resort-style living every day with BelleFair's indoor/outdoor pools, fitness center, indoor basketball court, playground, and dedicated train station shuttle! Enjoy luxury maintenance-free living! This is a Maintenance Included Home. HOA services include lawn care, snow removal, siding and roof repairs, clogged drains, shutter replacement, and painting of front door and garage trim. The property is vacant. Photos featuring furniture are virtually staged to help buyers envision the home's full potential.

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$1,475,000
3bedrooms
4bathrooms
land 405

By Julia B. Fee Sotheby's International Realty

Nearby
36
Video

House with pool Armonk (United States)

This spectacular limestone French Manor estate sits on 10+ acres on Converse Lake with 100'+ of lakefront in exclusive Conyers Farm, a guard gated community and private security. Custom designed for the current owners by architect James Davis, this meticulous home features impressive attention to detail. The main & garden level of the home are ideal for entertaining with an oversized great room, music room, formal living and dining room with double-sided fireplace. Many rooms open onto the terraces overlooking the lake and pool. The master bedroom suite is comprised of 4 rooms; sleeping room, 2 sitting rooms with a balcony and luxurious onyx bath. The four finished floors of living space feature 8 bedrooms, 11 full baths, 2 powder rooms, a full gym, indoor half basketball court with NBA 3-point line, a steam room, home theatre and every modern amenity. The grounds include a heated pool & spa, golf green & playground. There is a separate pool kitchen with dining area and changing rooms.

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$17,500,000
8bedrooms
12bathrooms
land 4.2ha

By Sotheby's International Realty - Greenwich Brokerage

Nearby
Contract pending
41

Property with pool Rye Brook (United States)

Move right into this beautifully appointed, turnkey home in the highly sought-after Bellefair community. This exceptional residence features dramatic cathedral ceilings, hardwood floors, elegant crown molding, and custom-finished California Closets throughout. A welcoming formal living room and dining room set the stage for entertaining, while the gourmet kitchen—complete with granite countertops and stainless steel appliances—opens seamlessly to an adjacent family room, perfect for everyday living. The spacious primary suite on the main floor offers two walk-in closets and a fully renovated, spa-like bathroom. Upstairs, you will find two generously sized bedrooms and a beautifully updated hall bath with dual sinks. The fully finished walk-out basement expands the living space with a full bath, a spacious recreation area, gym, and home office. Enjoy Bellefair's outstanding amenities, including fully renovated outdoor pool and indoor pool, a fitness center, country market, playground, and jitney service to the train. 67 Bellefair Road isn't just a home—it's a lifestyle.

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$1,350,000
3bedrooms
4bathrooms
land 607

By Julia B. Fee Sotheby's International Realty

Nearby
27

House Stamford (United States)

Don't miss this rare opportunity to own NEW construction in a desirable mid city, cul de sac neighborhood location. One of only two homes remaining in this 10-lot subdivision. This 5 bedroom, 3.5 bath colonial is comfortably proportioned and thoughtfully designed throughout with a relaxed, transitional style. The main level features an open and welcoming floor plan that easily connects living spaces. First and second floor home office options. The finished lower level adds versatility with a bedroom featuring a large-scale window for natural light, full bathroom, and pleasant sitting room-ideal for guest accommodations, in-law suite, teen retreat, or rec space. Excellent storage throughout ensures everything has its place. City water, city sewer, natural gas and underground utilities. Traveling distance from Walnut Ridge Court to the Stamford Train Station is a mere 2.5 miles and CT Transit has a stop practically at the front door. A grand opportunity for NEW construction in this limited NEW construction market.

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$1,495,000
5bedrooms
4bathrooms
land 1,052

By William Pitt Sotheby's International Realty

Nearby
2

House with garden and terrace Stamford (United States)

Beautifully rebuilt in 2006, this custom turn-key retreat offers 4 spacious Bedrooms with the flexibility for a 5th, 3 full & 2 half baths, all set on 2.33 acres of private, picturesque grounds; just 1 hour away from NYC. Arrive to curated landscaping surrounded by mature trees and seasonal blooms, including hydrangeas, geraniums, and climbing mandevilla, complemented by bespoke stonework and hand-crafted stepping stone paths. As you step inside, soaring ceilings and gleaming hardwood floors set the tone for the home's expansive, open-concept, anchored by a striking spiral staircase that makes an unforgettable first impression. Natural light pours through French doors, seamlessly connecting indoor and outdoor living. The living room, perfectly positioned off the grand foyer and family room, is filled with natural light and features a second fireplace crafted from premium natural limestone. The Family room is a true centerpiece, featuring vaulted ceilings & a grand wood-burning fireplace. Both warm and inviting, it's the perfect setting for cozy game nights or relaxing with hot chocolate by the fire while watching the snowfall outside. The Chef's Kitchen is both grand and functional, featuring high-end Viking appliances and designed for effortless entertaining, with seamless flow to the Dining and Living rooms and direct access to the outdoor patio, perfect for al fresco dining on a summer night. GPS Friendly.

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$2,275,000
510
4bedrooms
3bathrooms

By Annonceur International

Nearby
33

House with terrace Stamford (United States)

Exceptional NEW construction in a coveted mid-city location offers the perfect blend of refined comfortable living. This sensational 5-bedroom, 4.5 bathroom home with well proportioned rooms throughout, showcases sophisticated design together with an open-concept. The gourmet kitchen serves as the heart of the home, boasting a large center island, walk-in pantry, and abundant cabinet and counter space for the discerning chef. A fireplace and wet bar enhance the space with seamless access to an oversized deck. Four second floor bedrooms, 3 full baths and a full sized laundry room add to the comfort of this level. Thoughtful details include a fabulous mudroom with built ins for everyday convenience. The finished lower level expands living space with the fifth bedroom, full bathroom, and generous rec room, all enhanced by full-sized windows that flood the space with natural light throughout the day. Hardwood flooring, 9-foot ceilings and energy-efficient LED recessed lighting. City water and sewer, natural gas for heating and cooking plus underground utilities compliment the location. Traveling distance from Walnut Ridge Court to the Stamford Train Station is a mere 2.5 miles and CT Transit has a stop practically at the front door. A grand opportunity for NEW construction in this limited NEW construction market.

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$1,849,000
5bedrooms
5bathrooms
land 1,376

By William Pitt Sotheby's International Realty

Nearby
37

Property with garden Stamford (United States)

HIGHEST AND BEST OFFERS DUE SUNDAY, JUNE 7 6PM. Set at the top of a quiet cul-de-sac, this handsome Colonial-style home combines timeless appeal and generous space on a picturesque 1-acre property. With 5 bedrooms, 3.5 baths, and multiple living spaces, the home's layout easily supports both shared gatherings and private comfort. Most rooms boast beautiful hardwood flooring. A welcoming foyer introduces formal living and dining rooms. Spanning the full depth of the home, the living room receives natural light from large windows with east and west exposures, capturing morning and afternoon sun. The updated eat-in kitchen overlooks the backyard and features quartz countertops, KitchenAid appliances, and a stylish stainless steel farmhouse sink. Adjoining the kitchen is the spacious family room with a wood-burning fireplace. Tucked away is a private suite containing a bedroom, en-suite bath, and an office/flexible-use room, creating a perfect separate space for guests, multigenerational living, or a main-level primary. Upstairs are 4 more bedrooms, including the primary suite, which enjoys a walk-in closet, en-suite bath, and a private deck with views of the backyard's mature oaks, maples, and a flowering mountain laurel. The full unfinished basement and two-car garage provide ample storage and great potential for future expansion. In one of North Stamford's most convenient locations.

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$1,100,000
5bedrooms
4bathrooms
land 4,047

By William Pitt Sotheby's International Realty

Nearby
33

Property with garden Stamford (United States)

Beyond the classic white picket fence you will find a tastefully updated 1930's colonial in the heart of Stamford. The main level features an expansive living room with oak flooring and a wood-burning fireplace. The open floor plan has the dining room adjacent to the living room. The star of the home is the newly remodeled sleek designer kitchen with custom cabinets, quartz tops, and stainless appliances. A sparkling new powder room and mudroom complete the first floor and lead to the oversized deck in the back yard. Upstairs there are three bedrooms. The hall bath has been remodeled as has the primary bedroom, en-suite. The lower level has a home office, a playroom with a laundry nook, and a powder room. The sunny back yard has a detached 2-car garage and is completely fenced in. The home is in the desirable Hubbard Heights area, only steps to the vibrant Scalzi Park and shopping & dining at Ridgeway Plaza. Minutes to downtown Stamford, Metro North Train, and public beaches. Welcome Home!

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$749,000
3bedrooms
4bathrooms
land 567

By William Pitt Sotheby's International Realty

Nearby
50
Video

House with pool and garden Riverside (United States)

Perched in timeless elegance atop an expansive 2.91-acre gated peninsula, with best-in-class views of the Manhattan skyline and the shimmering Long Island Sound, Cedar Cliff is a Mediterranean villa of unrivaled pedigree and commanding presence. Privately situated along a secluded road within Riverside’s prestigious Indian Head Association, this storied property occupies the historic grounds of railroad magnate Henry Francis Shoemaker’s former compound—a Gilded Age legacy that later served as the backdrop for the iconic Cedar Cliff Beach Club of the 1920s. The estate bears the name Shoemaker originally gave his villa, ‘Cedar Cliff’—a designation that eventually defined the very road on which it stands today. Elevated high above the flood zone and offering 1,250 +/- feet of direct water frontage, the property unfolds with extraordinary scale and privacy. A sweeping, manicured lawn rolls gracefully toward the shoreline, creating a striking foreground to the panoramic coastal vistas and an exceptional setting for grand-scale entertaining. Each of the eight oversized bedrooms is oriented to capture breathtaking water views, while interiors blend the romance of pre-war craftsmanship with modern refinement—soaring ceilings, intricate millwork, antique wood floors, a three-level elevator and a professional recording studio. The East Wing, constructed in the early 2000s, introduces a new dimension of contemporary luxury, anchored by a sophisticated primary suite and complemented by a custom office, wine cellar, and private theater capable of accommodating up to twenty guests. The grounds rival those of a world-class private resort. A substantial stone pier and deep-water dock provide immediate access to open water, while a seaside tennis court with pergola and lighting offers championship-level play. At the water’s edge, a pool and spa are paired with a fully realized cabana featuring a fitness center, kitchenette, full bathroom and changing rooms. Sculpted into the eastern landscape, a series of stone terraces with a bluestone bar directly overlook Greenwich Cove and the vast protected expanse of Greenwich Point Park. Meticulously maintained and thoughtfully enhanced, the estate includes a newly installed Ludowici terra cotta roof, rebuilt sun decks, custom East Wing windows, and a full-property generator—ensuring seamless comfort and continuity. With access to a private beach and watercraft facilities, and located less than an hour from Manhattan and minutes from Westchester County Airport, the property offers a rare convergence of seclusion, scale, and global accessibility. Cedar Cliff is a singular offering for the most discerning buyer—an incomparable experience of refined luxury, inviting residents and their guests to revel in the natural beauty of one of the finest estates on the East Coast of the United States.

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$100,000,000
8bedrooms
14bathrooms
land 1.2ha

By Sotheby's International Realty - Greenwich Brokerage

Nearby
22

House Old Greenwich (United States)

Positioned along the crest of the hill to capture southern exposure and serene treetop views, this mid-century residence was thoughtfully designed by noted architect Walther Prokosch as his family home. Prokosch is perhaps best known as one of the architects behind the iconic JFK Pan Am Terminal, and his vision is evident throughout this distinctive property. The vaulted living and dining room is wrapped in walls of glass, flooding the interiors with natural light and creating a seamless connection to the surrounding landscape.The updated galley kitchen features modern appliances, a built-in banquet and sliders opening to a bluestone terrace, providing effortless indoor-outdoor living and entertaining. A private first-floor primary suite opens directly to the gardens, while additional first-floor rooms, ideal as bedrooms or home offices, share a full bath. The second floor offers two spacious double bedrooms and an additional full bath, creating a private retreat for family or guests. Mature natural gardens frame the property, enhancing the sense of privacy and tranquility. Set on an oversized .41-acre lot in an R-7 zone and only steps to Old Greenwich's parks, library, train, and village amenities. A rare opportunity to own an architecturally significant Mid-Century Modern home in one of Old Greenwich's most coveted neighborhoods.

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$1,895,000
4bedrooms
3bathrooms
land 1,659

By Sotheby's International Realty - Greenwich Brokerage

Nearby
50
Video

House with garden Killingworth (United States)

Welcome to Stone Heron Farm, an extraordinary 74+ acre estate offered as five parcels, creating one of the most versatile and rare compound opportunities in Connecticut. Tucked away on a quiet country road, 12 Jackson Road combines timeless New England charm with exceptional land value, privacy and multi-use potential. The main residence, an updated 1806 Cape, features exposed beams, rich wide-plank flooring, 3 bedrooms, 3 baths, a main level master suite, 4 fireplaces and a wraparound deck creating a warm, inviting atmosphere with a sophisticated farmhouse flair. The chef's kitchen is a culinary dream with handcrafted cabinetry, granite countertops, and top-of-the-line SubZero and Wolf appliances. A separate guest cottage with kitchen and bath offers private accommodations for visitors, extended family, or creative studio use. A large workshop adds further utility for hobbyists, artists, or equipment needs. Across the estate, enjoy scenic walking trails, stone walls, open meadows and wooded acreage. A beautifully sited pond house overlooking the water provides a peaceful retreat for year-round enjoyment and breathtaking views. Multiple barns, paddocks, and cleared pastures offer ideal conditions for horses, small livestock, gardening, or future agricultural use. Possibilities include a multi-home compound, expanded equestrian facilities, conservation strategies, or simply a private sanctuary. A truly exceptional offering with endless potential. Convenient to the Connecticut shoreline, New Haven, Middletown, Route 9 and commuter routes, yet wonderfully secluded, this estate is perfect for buyers seeking privacy, creativity, and a lifestyle deeply connected to nature. A private hangar at an FBO may be included.

… 
$1,895,000

By Sotheby's International Realty - Greenwich Brokerage

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