Greenwich, CT Homes for Sale with Pool

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  /29

  $9,950,000

  • 6 Beds
  • 8 Baths
  • 8,896 Sq Ft

  35 Club Rd, Riverside, CT 06878

  Sought after Riverside location showcases a stunning six-bedroom Colonial built by Sound Beach Partners with pool, porches, outdoor fireplace and grill on beautifully manicured .71 acres with private yard dotted with sequentially flowering trees. Offers easy access to trains, schools, water and Yacht Club. This pristine home exudes classic elegance with superb architectural details, wood floors,

  

  Andrew Smith

  Houlihan Lawrence

  (475) 265-6383

  35 Club Rd, Riverside, CT 06878
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  /27

  $6,250,000

  • 6 Beds
  • 8 Baths
  • 7,447 Sq Ft

  79 Richmond Hill Rd, Greenwich, CT 06831

  Completely renovated exquisitely designed Colonial-style home, nestled on 4 park-like acres. Custom millwork, built-ins, designer lighting, and European fixtures. Light-filled family dining area featuring a 20-foot curved sliding glass wall that opens to the patio and pool. The Primary Suite boasts private balcony, large dressing room, and luxurious bath complete with radiant heated floors,

  

  Kevin Stone

  Sotheby's International Realty

  (475) 255-6696

  79 Richmond Hill Rd, Greenwich, CT 06831
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  /39

  $1,899,000

  • 4 Beds
  • 4.5 Baths
  • 2,773 Sq Ft

  51 Forest Ave Unit 98, Old Greenwich, CT 06870

  This rare 4 bedroom,4.5 bath renovated unit the the popular Old Greenwich Gables complex with pool and fitness center. This light and bright updated open plan ground floor with primary on first and second floor. Private balcony and patio. Close distance to train, Binney Park and new Civic Center. International School at Dundee and Eastern Middle school and short distance to the beach make this a

  Constance Stuart Jones Coldwell Banker Realty

  51 Forest Ave Unit 98, Old Greenwich, CT 06870
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  /7

  $8,750,000

  • 6 Beds
  • 7.5 Baths
  • 10,400 Sq Ft

  11 Winterset Rd, Greenwich, CT 06830

  Mid Country New Construction smart home on 2.16 exquisite level acres will be completed by early fall, 2025. 10K+ SF of finished space on 4 floors with extra height ceilings throughout. Primary suite and 4 en-suite bedrooms on 2nd floor and a 6th en-suite bedroom on 3rd floor. Custom kitchen with Subzero/Wolf Appliances, island and breakfast area. Spectacular indoor / outdoor living is designed

  Amanda Bates Houlihan Lawrence Inc.

  11 Winterset Rd, Greenwich, CT 06830
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  /31

  $6,550,000

  • 7 Beds
  • 9 Baths
  • 10,723 Sq Ft

  28 Thunder Mountain Rd, Greenwich, CT 06831

  Elegance and luxury define this light-filled modern stone + clapboard home on 2 stunning acres near town + schools. Designed by Rich Granoff, this 7-bedroom, 7.2-bath residence offers exceptional indoor/outdoor living w pool, spa, covered terrace w fireplace + firepit—all on a quiet cul-de-sac. Built in 2005 and recently redesigned, the open floor plan + soaring ceilings create a bright, airy

  B.K. Bates Houlihan Lawrence

  28 Thunder Mountain Rd, Greenwich, CT 06831
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  /31

  $13,400,000

  • 6 Beds
  • 9 Baths
  • 11,157 Sq Ft

  31 Meadow Ln, Greenwich, CT 06831

  Exceptional Tanner White ultra-luxurious six-bedroom modern residence in the estate area of Greenwich. The open floor plan with 12+ foot ceilings is filled with natural light and allows for versatile use of the dramatic formal and casual rooms, all leading to a captivating outdoor living space complete with a fireplace overlooking the serene pool with spa and verdant lawn. The interior design and

  Leslie McElwreath Sotheby's International Realty

  31 Meadow Ln, Greenwich, CT 06831
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  /54

  $8,250,000

  • 6 Beds
  • 10 Baths
  • 9,600 Sq Ft

  828 North St, Greenwich, CT 06831

  Pristine stone Georgian colonial set on over four acres of verdant level lawn in back country Greenwich. Custom built, this 9,600+/- SF home was crafted with high ceilings, custom moldings and superb attention to detail on all three levels serviced by an elevator. Stunning double height entry, elegant formal rooms, gourmet kitchen with sun-filled breakfast area adjoining double height family room

  Leslie McElwreath Sotheby's International Realty

  828 North St, Greenwich, CT 06831
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  /40

  $8,850,000

  • 6 Beds
  • 8 Baths
  • 9,440 Sq Ft

  34 Carrington Dr, Greenwich, CT 06831

  A rare offering in back-country Greenwich, this timeless estate is set on 3.58 exquisitely landscaped and gated acres, masterfully blending classic architecture with contemporary luxury. Designed for both grand-scale entertaining and intimate everyday living, the residence offers a sun-filled interior with soaring ceilings, custom millwork, and modern, bespoke finishes throughout. The grand

  Carissa Larriuz Houlihan Lawrence

  34 Carrington Dr, Greenwich, CT 06831
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  /44

  $19,500,000

  • 8 Beds
  • 17 Baths
  • 26,454 Sq Ft

  11 Langhorne Ln, Greenwich, CT 06831

  Famed architect Boris Baranovich designed this extraordinary stone Georgian estate of 26,000+/- square feet on 8.788 secluded acres off of Round Hill Road. Exquisitely executed, this stately manor home offers eight bedrooms and twelve full and five half bathrooms throughout four levels of living space. Mature trees and lush lawn surround this exceptional estate with two gated entrances: one to

  Leslie McElwreath Sotheby's International Realty

  11 Langhorne Ln, Greenwich, CT 06831
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  /43

  $6,700,000

  • 6 Beds
  • 11 Baths
  • 10,036 Sq Ft

  280 Round Hill Rd, Greenwich, CT 06831

  Ideally sited on more than two acres just minutes from town, this timeless and light-filled colonial offers the perfect blend of classic elegance and modern luxury. Graciously scaled rooms begin with an expansive foyer that provides a stunning front-to-back view, setting the tone for the rest of the home.The main residence features a private gym, home theater, custom 1,000-bottle wine cellar,

  Susan Holey Sotheby's International Realty

  280 Round Hill Rd, Greenwich, CT 06831
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  /50

  $14,250,000

  • 6 Beds
  • 8 Baths
  • 9,418 Sq Ft

  52 Carriglea Dr, Riverside, CT 06878

  Experience unparalleled luxury in this extraordinary custom-built Riverside waterfront residence. Nestled on 1.45 acres with 9,418 square feet of living space, this exceptional home, designed by acclaimed architect Cormac Byrne, boasts a seamless open-concept layout that promotes effortless flow throughout. Soaring ceilings and expansive windows flood the interiors with natural light,

  Stephen Archino Sotheby's International Realty

  52 Carriglea Dr, Riverside, CT 06878
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  /38

  $7,250,000

  • 5 Beds
  • 6 Baths
  • 6,714 Sq Ft

  21 Aiken Rd, Greenwich, CT 06831

  Introducing a timeless Round Hill estate, on the market for the first time in over 50 years. Nestled midway along a quiet cul-de-sac, this pastoral property spans over 10+ sweeping, private acres with mature plantings and specimen tress overlooking a tranquil pond. The main residence features beautifully proportioned, sun-filled rooms, 5 bedrooms, 4 full and 2 half baths, and a walk-out lower

  Krissy Blake Sotheby's International Realty

  21 Aiken Rd, Greenwich, CT 06831
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  /38

  $6,300,000

  • 9 Beds
  • 6.5 Baths
  • 6,841 Sq Ft

  78 Khakum Wood Rd, Greenwich, CT 06831

  78 Khakum Wood occupies a premier position in one of Greenwich's most distinguished private enclaves. Originally envisioned by Newton Phelps Stokes and developed in collaboration with the renowned Olmsted Brothers, this exceptional property is set on 2.95 beautifully landscaped acres. The residence showcases its charming Tudor architecture with the characteristic pitched gabled roof, decorative

  Deborah Huffard Houlihan Lawrence

  78 Khakum Wood Rd, Greenwich, CT 06831
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  /52

  $13,995,000

  • 5 Beds
  • 9 Baths
  • 10,431 Sq Ft

  190 North St, Greenwich, CT 06830

  Nor Tor stands as one of Greenwich's finest English Manors, an extraordinary estate spanning nearly 3.5 acres of breathtaking beauty. Meticulously preserved, the manor underwent an extensive three year restoration and expansion, completed in 2010, blending historical integrity with seamless enhancements. This masterful renovation was led by architect Ira Grandberg, resulting in a breathtaking

  Leslie McElwreath Sotheby's International Realty

  190 North St, Greenwich, CT 06830
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  /26

  $11,500,000

  • 7 Beds
  • 12 Baths
  • 10,058 Sq Ft

  35 Andrews Farm Rd, Greenwich, CT 06831

  Elegantly updated & impeccably maintained, this 10K+ SF estate is set on 8 manicured acres in the exclusive, gated Andrews Farm Association. Offering 7 bedrooms & 7.5 baths, this timeless home blends classic architecture with modern convenience, including a recent renovation featuring modern systems & smart home technology. The grounds, designed by renowned landscape architect Penelope Hobhouse,

  Kevin Sneddon Compass Connecticut, LLC

  35 Andrews Farm Rd, Greenwich, CT 06831
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  /50

  $6,800,000

  • 5 Beds
  • 10 Baths
  • 7,632 Sq Ft

  21 Calhoun Dr, Greenwich, CT 06831

  Welcome to ''Park Hill'', a stunning English Tudor Revival Manor known as ''The House of Seven Gables''. Updated in 2025, this historic gem nestled in the heart of Greenwich on a 1.81-acre oversized lot, offers privacy & a unique blend of timeless elegance with modern conveniences. Located in the desirable Calhoun Drive Association, this property boasts both beauty & charm. The manor's

  Danielle Claroni Sotheby's International Realty

  21 Calhoun Dr, Greenwich, CT 06831
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  /44

  $6,750,000

  • 5 Beds
  • 9 Baths
  • 9,974 Sq Ft

  386 North St, Greenwich, CT 06830

  This 9,974 sq. ft. estate, nestled in 2.3 acres of pristine, park-like grounds, epitomizes understated luxury. A handcrafted brick facade and hand-split shingle roof frame interiors adorned with rare materials and custom millwork. A grand, 2-story foyer leads to a formal area designed for refined entertaining. The luxury primary suite provides a serene retreat with a double private office and a

  Stephen Archino Sotheby's International Realty

  386 North St, Greenwich, CT 06830
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  /31

  $8,950,000

  • 6 Beds
  • 5.5 Baths
  • 5,040 Sq Ft

  33 Meadow Wood Dr, Greenwich, CT 06830

  In the gated Quarry Farm neighborhood of the enchanting Belle Haven Association with 24hr security, this property offers a unique opportunity to renovate or build new, 16,000+ sq ft waterfront home. Overlooking Byram Harbor and Long Island Sound, the current 6-bedroom house sits on 2.78 acres with a pool, adjacent to a 1.09-acre protected lot. Once a quarry and later acquired as part of the

  Joseph Barbieri Sotheby's International Realty

  33 Meadow Wood Dr, Greenwich, CT 06830
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  /36

  $7,500,000

  • 7 Beds
  • 9 Baths
  • 14,066 Sq Ft

  4 Cowdray Park Dr, Greenwich, CT 06831

  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

  Joan Marks Christie's International Real Estate

  4 Cowdray Park Dr, Greenwich, CT 06831
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  /49

  $6,395,000

  • 7 Beds
  • 8 Baths
  • 8,068 Sq Ft

  2 Winding Ln, Greenwich, CT 06831

  LOCATION, LOCATION LOCATION Set back on 2 private acres very close to town & landscaped to perfection, this exquisite property with over sized salt water pool, tennis court, children's playground, exquisite gardens & entertaining terraces offer today's buyers the perfect lifestyle. 8000+sq.ft. brick residence w/ new slate composite roof features 6 bdrms/6 bths, private office., lg light filled

  Helene Barre Sotheby's International Realty

  2 Winding Ln, Greenwich, CT 06831
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  /7

  $7,995,000

  • 8 Beds
  • 11.5 Baths
  • 10,646 Sq Ft

  68 Dearfield Dr, Greenwich, CT 06831

  Perched high on a hill in downtown Greenwich, 66 Dearfield is unparalleled in its grandeur with over 10,000 square feet of luxury living spanning 4 floors. Close to Greenwich Library, Greenwich Avenue, the train and all downtown amenities. This exquisite colonial boasts stone chimneys with extra height ceilings on each floor. Upon entry, the 2 story foyer nestled between the living room and

  Nina Frandson BHHS New England Properties

  68 Dearfield Dr, Greenwich, CT 06831
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  /42

  $8,950,000

  • 10 Beds
  • 9 Baths
  • 9,483 Sq Ft

  14 Meadow Dr, Greenwich, CT 06831

  DISCOVER BREEZEMORE Experience the rare opportunity to own a piece of history with the stunning Breezemore estate located in Greenwich, Connecticut. Built in 1909, this magnificent property offers 10,000 square feet of architectural splendor, old-world charm, and modern conveniences. Set high on 3.2 private, park-like acres within close distance of downtown Greenwich, this property stands

  Ryan Hoffman Houlihan Lawrence

  14 Meadow Dr, Greenwich, CT 06831
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  /32

  $8,950,000

  • 6 Beds
  • 10 Baths
  • 8,146 Sq Ft

  26 Andrews Farm Rd, Greenwich, CT 06831

  Classic brick Georgian updated for today's lifestyle. Just renovated, the residence features high ceilings, oversized windows, hardwood flooring, tasteful stone and tile throughout three levels, a splendid backdrop for both formal and casual entertaining. One of a kind first-floor primary suite with two stunning bathrooms and two dressing rooms. Elegant formal rooms open to a west-facing brick

  Leslie McElwreath Sotheby's International Realty

  26 Andrews Farm Rd, Greenwich, CT 06831
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  /38

  $7,995,000

  • 6 Beds
  • 10 Baths
  • 10,796 Sq Ft

  230 Taconic Rd, Greenwich, CT 06831

  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

  Ellen Mosher Houlihan Lawrence

  230 Taconic Rd, Greenwich, CT 06831
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  /37

  $6,950,000

  • 6 Beds
  • 9 Baths
  • 11,615 Sq Ft

  21 Sterling Rd S, Armonk, NY 10504

  Where design meets purpose—this award-winning home brings together architectural innovation and serene luxury. Created by Carol Kurth Architecture and built by Legacy Construction NE, exceptional craftsmanship is seen throughout the home, showcased by a mix of natural materials and bold structural details. A cantilevered fireplace, floating staircases and cathedral ceilings are some of the

  Brian Milton Compass Greater NY, LLC

  21 Sterling Rd S, Armonk, NY 10504
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  /40

  $1,399,000

  • 3 Beds
  • 3 Baths
  • 2,175 Sq Ft

  88 Indian Field Rd, Greenwich, CT 06830

  Welcome to 88 Indian Field Road, where convenience meets comfort in this updated 3 bed, 3 bath cape. Seconds from the Cos Cob Train station, Greenwich schools, parks, and dozens of dining & shopping options, this home offers unparalleled accessibility. Highlights of the surprisingly spacious layout include the living room's w/b fireplace, renovated kitchen and inviting family room perfect for

  PJ Collins Keller Williams Realty Group

  88 Indian Field Rd, Greenwich, CT 06830
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  /41

  $799,000

  • 3 Beds
  • 1.5 Baths
  • 1,362 Sq Ft

  75 Cos Cob Ave Unit 10, Cos Cob, CT 06807

  A Rare Find in Greenwich!Located in the desirable Rockybrook Woods Association, this 3-bedroom condo is truly rare in Greenwich—offering more space and flexibility than typically available at this price. Featuring gleaming, recently refinished hardwood floors throughout, the unit includes a relaxing deck, stylish kitchen and baths, and a flowing layout. The kitchen opens seamlessly to the

  Angela Alfano Coldwell Banker Realty

  75 Cos Cob Ave Unit 10, Cos Cob, CT 06807
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  /36

  $2,149,000

  • 5 Beds
  • 3.5 Baths
  • 3,506 Sq Ft

  46 Bowman Dr, Greenwich, CT 06831

  Experience the exceptional craftsmanship and refined details in this meticulously maintained home within the prestigious King Merritt association. The chef's kitchen is a culinary masterpiece, featuring Wolf and Sub-Zero appliances, a double oven, wine cooler, stunning oversized Carrara marble center island, and an additional stacked washer/dryer. Seamlessly integrated with a spacious

  Joy Kim Metalios Houlihan Lawrence

  46 Bowman Dr, Greenwich, CT 06831
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  /13

  $799,000

  • 1 Bed
  • 2 Baths
  • 947 Sq Ft

  51 Forest Ave Unit 60, Old Greenwich, CT 06870

  One bedroom with den with 2 full baths on one level on second floor near elevator. En suite primary bath. Private terrace. Assigned indoor garage space and personal storage unit. Association features brick promenades and landscaped courtyards with gardens and water fountains, large outdoor pool (near unit), fitness center and squash court. Convenient to Old Greenwich Metro-North train station. No

  Marc Robinson Coldwell Banker Realty

  51 Forest Ave Unit 60, Old Greenwich, CT 06870
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  /21

  $750,000

  • 2 Beds
  • 1.5 Baths
  • 1,222 Sq Ft

  75 Cos Cob Ave Unit 9, Cos Cob, CT 06807

  Step inside this beautifully renovated 2-bedroom, 1.1-bath condominium, offering 1,222 square feet of stylish, reimagined living space. Every detail has been thoughtfully updated—from the beautifully appointed kitchen featuring custom cabinetry, quartzite countertops, and stainless steel appliances, to the elegant lighting and white oak flooring throughout. Recent upgrades include a brand-new

  Jenny Allen Compass Connecticut, LLC

  75 Cos Cob Ave Unit 9, Cos Cob, CT 06807
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  /41

  $825,000

  • 1 Bed
  • 2 Baths
  • 1,160 Sq Ft

  51 Forest Ave Unit 31, Old Greenwich, CT 06870

  Great opportunity to enjoy the Old Greenwich lifestyle in this stunning one bedroom with den condo renovation offering one-level living in coveted Old Greenwich Gables . Up-to-the-minute kitchen with quartz countertops, updated bathrooms and quality appointments throughout enhance the inviting open floor plan. Lounge on your terrace or take advantage of the Association pool, squash court,

  Patricia Cameron BHHS New England Properties

  51 Forest Ave Unit 31, Old Greenwich, CT 06870
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  /28

  $2,500,000

  • 5 Beds
  • 4 Baths
  • 3,772 Sq Ft

  43 Buckfield Ln, Greenwich, CT 06831

  Nestled at the end of a quiet street in one of the most prestigious towns in the country, this rare 8.5-acre estate in Greenwich, offers an exceptional opportunity for those seeking space, privacy, and potential. Built in 1936, this stately residence features 5 bedrooms, 4 full bathrooms, and over 3,700 square feet of living space, all set on a sprawling flat parcel rarely found in the area. The

  Jolanta Rojek eXp Realty

  43 Buckfield Ln, Greenwich, CT 06831
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  /28

  $3,495,000

  • 6 Beds
  • 8 Baths
  • 5,613 Sq Ft

  4 Mountain Laurel Dr, Greenwich, CT 06831

  Stately Georgian brick on a private cul-de-sac w/2 landscaped acres, stunning pool & spa. Approach via wrought iron gates to a circular driveway. Elegant, beautifully decorated home boasts 5,613 SF (add. 1000+/- sf in finished part of garden level), high ceilings, hardwood & stone floors & 5 fireplaces. Spacious entry foyer leads to gourmet kitchen w/Sub Zero, Viking & Bosch appliances, adj.

  Barbara Wells Houlihan Lawrence

  4 Mountain Laurel Dr, Greenwich, CT 06831
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  /49

  $5,200,000

  • 6 Beds
  • 9 Baths
  • 7,738 Sq Ft

  897 Lake Ave, Greenwich, CT 06831

  Peaceful, serene and private best describes this property located on a lane off Lake Avenue adjacent conservation. 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

  Marjorie Marianacci Coldwell Banker Realty

  897 Lake Ave, Greenwich, CT 06831
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  /53

  $4,995,000

  • 4 Beds
  • 6 Baths
  • 5,244 Sq Ft

  34 Edgewood Dr, Greenwich, CT 06831

  Tucked discreetly at the end of a long, private drive in coveted mid-country Greenwich, masterfully renovated in 2025 this Colonial offers a harmonious blend of heritage architecture and sophisticated modernity. Designed to accommodate both grand-scale entertaining and intimate daily living, the residence unfolds across three levels and over 7,000 square feet of meticulously curated

  Danielle Scialpi-Malloy Serhant Connecticut LLC

  34 Edgewood Dr, Greenwich, CT 06831
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  /20

  $22,000,000

  • 8 Beds
  • 12 Baths
  • 14,071 Sq Ft

  8 Fox Run Ln, Greenwich, CT 06831

  Ultra-stylish 2024 custom-built Contemporary from visionary developer SBP Homes graces nearly 5.5 private, gated acres very close to town with pool, spa, two-bedroom pool house, porches, outdoor kitchen, fireplace and tennis court designed for optimum indoor/outdoor entertaining and relaxed living. Luxurious details elevate the 11,000+ sq. Interior with Bulthaup kitchen, living room bar; walls

  James Hoffman Houlihan Lawrence

  8 Fox Run Ln, Greenwich, CT 06831
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  /20

  $5,850,000

  • 5 Beds
  • 5.5 Baths
  • 8,818 Sq Ft

  12 Dwight Ln, Greenwich, CT 06831

  Experience the charm of a genuine 17th-century Elizabethan manor, meticulously reconstructed on over four acres of beautifully landscaped grounds showcasing exquisite gardens, stunning masonry, and exceptional amenities. Located on a picturesque private lane, this home preserves the architectural essence of a classic English manor, featuring historic wooden beams sourced and carefully dismantled

  Yashmin Lloyds Compass Connecticut, LLC

  12 Dwight Ln, Greenwich, CT 06831
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  /38

  $4,350,000

  • 5 Beds
  • 6.5 Baths
  • 5,257 Sq Ft

  331 Round Hill Rd, Greenwich, CT 06831

  Built in 1758 and masterfully updated, 331 Round Hill Road offers a rare opportunity where historic character and modern comfort exist in perfect balance. Wide-plank floors, hand-hewn beams, and wood-burning fireplaces showcase early American craftsmanship, while a reimagined kitchen with premium appliances and renovated baths provides seamless functionality. The large living room offers a quiet

  Jack Sarsen Compass Connecticut, LLC

  331 Round Hill Rd, Greenwich, CT 06831
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  /51

  $19,900,000

  • 7 Beds
  • 10 Baths
  • 18,000 Sq Ft

  37 Burying Hill Rd, Greenwich, CT 06831

  Custom designed and built to exacting standards, this phenomenal back country lakefront compound was built to exacting standards offering fabulous privacy and flexibility for families, guests and staff. Prominent local design build firm created a masterpiece that combines a pre war elegance with substantial entertaining and modern lifestyle amenities. Multiple structures, including a large pool

  Robert Johnson Brown Harris Stevens CT, LLC

  37 Burying Hill Rd, Greenwich, CT 06831
• 

  

  /49

  $2,650,000

  • 4 Beds
  • 4.5 Baths
  • 4,447 Sq Ft

  5 Whitney Dr, Greenwich, CT 06831

  Stone pillars and a serene Koi pond set the tone as you enter this beautiful property offering 4.58acres abutting the Audubon Sanctuary and trails. This easy living ranch home offers an open and sundrenched layout. The dramatic foyer boasts soaring ceilings and walls of windows and doors surrounding you. Take a gracious step down into the living room with fireplace and doors to an expansive

  Lisa DeFonce Houlihan Lawrence

  5 Whitney Dr, Greenwich, CT 06831

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