5-Bedroom Homes for Sale in Old Greenwich, CT

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  /36

  $5,100,000 Open Sun 1PM - 3PM

  • 6 Beds
  • 8 Baths
  • 7,930 Sq Ft

  20 Sherwood Farm Ln, Greenwich, CT 06831

  Step into luxury with this newly staged custom built home in one of Greenwich's prestigious associations. Perfectly situated near downtown, this elegant property offers a blend of sophistication and convenience- now at an improved price! 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

  

  Richard Higgins

  Higgins Group Bedford Square

  (203) 433-0559

  20 Sherwood Farm Ln, Greenwich, CT 06831
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  /40

  $1,750,000 Open Sun 1PM - 3PM

  • 6 Beds
  • 5 Baths
  • 3,461 Sq Ft

  47 Hollow Tree Ridge Rd, Darien, CT 06820

  PRICE ADJUSTMENT. A Rare Darien Gem and opportunity to own this historic Federal Colonial 2-family home, one of Darien's few multi-family properties. Spanning over 3,460 SF on .47 acres, this turn-key furnished residence blends timeless elegance with modern versatility, ideal for investors, families, multi-generational households, or those seeking rental income. Historic Charm, Modern Comfort: *

  

  Karen Finn

  Gatehouse Realty Inc

  (475) 325-5924

  47 Hollow Tree Ridge Rd, Darien, CT 06820
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  /10

  $16,750,000

  • 8 Beds
  • 11 Baths
  • 16,300 Sq Ft

  90 Oneida Dr, Greenwich, CT 06830

  Build your legacy in one of Greenwich, CT's most sought-after downtown gated communities. Approved plans and ready to break ground with local Award winning developer, Greenwich Custom Homes. A magnificent estate will be built with precision and finished with elegance, continuing to raise the bar for the finest living in Greenwich CT. This waterfront Georgian Colonial blends timeless elegance with

  Brian Milton Compass Connecticut, LLC

  90 Oneida Dr, Greenwich, CT 06830
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  /38

  $7,950,000

  • 6 Beds
  • 9 Baths
  • 8,970 Sq Ft

  105 Woodside Dr, Greenwich, CT 06830

  This stately prewar stone manor, located in the exclusive gated community of Milbrook, has been thoughtfully expanded and reimagined for modern living while preserving its timeless elegance. Stepping into the grand foyer, graced with a beautiful curved staircase, the home reveals its extraordinary character and sophistication.Designed for both comfortable living and exceptional entertaining,

  Sarah Muir Houlihan Lawrence

  105 Woodside Dr, Greenwich, CT 06830
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  /34

  $12,450,000

  • 5 Beds
  • 7 Baths
  • 8,306 Sq Ft

  21 Guinea Rd, Greenwich, CT 06830

  Hidden beyond a private gated drive, majestically sited atop 5.5 enchanting acres, Fox Lair reveals herself. A 1938 English manor reimagined for today, timeless architectural detail meets modern updates resulting in a home equally suited to formal entertaining or the rigors & joys of family life. The romance of a bygone era blends seamlessly with the spacious gourmet kitchen, family

  Julie Grace Burke Compass Connecticut, LLC

  21 Guinea Rd, Greenwich, CT 06830
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  /27

  $11,995,000

  • 6 Beds
  • 8.5 Baths
  • 11,830 Sq Ft

  12 Turner Dr, Greenwich, CT 06831

  Welcome to 12 Turner Drive, a stunning home where timeless design meets luxurious living. This custom-built masterpiece spans 11,830 sq. ft. on a generous 1.16-acre lot, offering 6 bedrooms and 8.5 bathrooms with a blend of sophistication and modern amenities. The home features a striking double-height entryway, setting the tone for exquisite craftsmanship within. The main level showcases

  Yashmin Lloyds Compass Connecticut, LLC

  12 Turner Dr, Greenwich, CT 06831
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  /50

  $6,400,000

  • 5 Beds
  • 8 Baths
  • 7,492 Sq Ft

  101 Perkins Rd, Greenwich, CT 06830

  Situated high above Perkins Road on 2.6 acres this gated mid country 5 bedroom/5 bath residence is the ultimate in CHIC style and architectural SOPHISTICATION while also offering cozy comfort. This beautiful home has been recently updated by the current owner with many major high end improvements... including a new cedar roof, new HVAC system and conversion to propane. Second floor primary

  Francine Ehrlich Sotheby's International Realty

  101 Perkins Rd, Greenwich, CT 06830
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  /64

  $16,750,000

  • 5 Beds
  • 9 Baths
  • 13,031 Sq Ft

  50 Dingletown Rd, Greenwich, CT 06830

  Peace and tranquility amid 7.37 lush acres, just minutes from Downtown Greenwich: this is Harkaway Farm, a distinguished Georgian Colonial estate set behind stately stone pillars and impressive gates. A meandering drive carries you over a stone bridge fording a gentle stream, to the recently transformed home. Framed by idyllic views of Oakley Pond, the light-filled 11,000+ square foot manor

  Francine Ehrlich Sotheby's International Realty

  50 Dingletown Rd, Greenwich, CT 06830
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  /39

  $11,750,000

  • 7 Beds
  • 10 Baths
  • 9,992 Sq Ft

  10 Copper Beech Rd, Greenwich, CT 06830

  Nestled privately, and surrounded by matured trees, on 1.82 bucolic mid-country acres, sits this seven bedroom, seven full and three half bath, gorgeous estate! Extraordinary stone & shingle construction, built by Aberdeen Properties, and gardens magnificently designed by Rutherford & Associates. Dramatic front to back, double height entry, exquisite millwork throughout, 10' ceilings, and a

  Roberta Jurik Berkshire Hathaway NE Prop.

  10 Copper Beech Rd, Greenwich, CT 06830
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  /39

  $5,795,000

  • 6 Beds
  • 5.5 Baths
  • 5,577 Sq Ft

  21 Ridge St, Greenwich, CT 06830

  Situated on a quiet St. in the heart of Greenwich, this cedar/stone house is beautifully designed with the style and comfort to meet the needs in today's living. Taken down to the studs, expanded, and professionally designed by the owners. A welcoming front porch opens to the two-story, dramatically lit entry hall w/ repetitive archways passing by a gracious LR, into the light, bright

  Dorothy Salisbury Coldwell Banker Realty

  21 Ridge St, Greenwich, CT 06830
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  /12

  $5,900,000

  • 6 Beds
  • 7 Baths
  • 7,600 Sq Ft

  6 Dorchester Ln, Riverside, CT 06878

  Just Completed! 2025 Luxury new construction in a fabulous Riverside location! This beautifully designed home features a double height entrance with front to back views, a sophisticated living room, dining room with tray ceiling, and office with access to a covered terrace and outdoor fireplace. The gourmet kitchen with high-end appliances and breakfast area is next to the family room with a

  Gloria Gimenez-Ferrer Berkshire Hathaway HS NE Prop.

  6 Dorchester Ln, Riverside, CT 06878
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  /47

  $5,995,000

  • 6 Beds
  • 9 Baths
  • 6,520 Sq Ft

  25 Dialstone Ln, Riverside, CT 06878

  Discover the perfect blend of modern luxury and thoughtful design in this 6-bedroom, 7.2 half-bath home with room for a pool tucked away on a quiet cul-de-sac in Riverside. Just steps from top schools, transportation, parks, and Old Greenwich village, this 6,500 sq. ft. residence spans four finely crafted levels, offering ultimate convenience and comfort. The main level impresses with soaring 10+

  Carol Zuckert Sotheby's International Realty

  25 Dialstone Ln, Riverside, CT 06878
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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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  /31

  $6,500,000

  • 6 Beds
  • 4 Baths
  • 2,833 Sq Ft

  0 Rich Island Unit 24092237, Greenwich, CT 06830

  A one-of-a-kind offering, this property provides sweeping views of Long Island Sound and the allure of your own island. The expansive half-acre property, shaded by mature trees, also features its own boat dock and two boats for exploration of nearby waters and islands. Meticulously landscaped grounds with beautiful perennial gardens provide a picturesque setting for outdoor events. A beautiful

  Margriet McGowan Sotheby's International Realty

  0 Rich Island Unit 24092237, Greenwich, CT 06830
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  /37

  $6,500,000

  • 6 Beds
  • 4 Baths
  • 2,833 Sq Ft

  0 Rich Island Unit KEY855821, Greenwich, CT 06830

  A one-of-a-kind offering, this property provides sweeping views of Long Island Sound and the allure of your own island. The expansive half-acre property, shaded by mature trees, also features its own boat dock and two boats for exploration of nearby waters and islands. Meticulously landscaped grounds with beautiful perennial gardens provide a picturesque setting for outdoor events. A beautiful

  Margriet McGowan Sotheby's International Realty

  0 Rich Island Unit KEY855821, Greenwich, CT 06830
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  /37

  $6,500,000

  • 6 Beds
  • 4 Baths
  • 2,833 Sq Ft

  0 Rich Island Unit 122625, Greenwich, CT 06830

  A one-of-a-kind offering, this property provides sweeping views of Long Island Sound and the allure of your own island. The expansive half-acre property, shaded by mature trees, also features its own boat dock and two boats for exploration of nearby waters and islands. Meticulously landscaped grounds with beautiful perennial gardens provide a picturesque setting for outdoor events. A beautiful

  Margriet McGowan Sotheby's International Realty

  0 Rich Island Unit 122625, Greenwich, CT 06830
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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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  /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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  /10

  $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 10,646 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 dining

  Nina Frandson BHHS New England Properties

  68 Dearfield Dr, Greenwich, CT 06831
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  $5,795,000 Open Sun 2PM - 4PM

  • 6 Beds
  • 7 Baths
  • 6,673 Sq Ft

  7 Jones Park Dr, Riverside, CT 06878

  Nestled on a beloved tree-lined cul-de-sac, this custom-built residence perfectly blends a traditional coastal Connecticut shingle style with a sun-filled, modern open-plan interior all just steps from Riverside Yacht Club, schools, and train. Thoughtfully designed, the home incorporates bespoke architectural elements including tall ceilings, custom millwork, expansive windows and wide-plank

  Ellen Mosher Houlihan Lawrence

  7 Jones Park Dr, Riverside, CT 06878
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  /40

  $8,250,000

  • 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 with 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 proudly

  Ryan Hoffman Houlihan Lawrence

  14 Meadow Dr, Greenwich, CT 06831
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  /25

  $2,795,000

  • 5 Beds
  • 3.5 Baths
  • 3,800 Sq Ft

  11 Orchard Place Unit B, Greenwich, CT 06830

  Welcome to one of the largest townhouses in Greenwich! 11 Orchard is located in a super convenient Greenwich location; close to the train, town, and next door to the lovely Bruce Park. The main floor boasts a formal living room with fireplace, dining room, and expansive eat-in kitchen plus living room, which flows to the rear patio and yard. High end kitchen appliances and a huge island make for

  Daniel Berger RE/MAX Prestige Properties

  11 Orchard Place Unit B, Greenwich, CT 06830
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  /50

  $5,500,000

  • 5 Beds
  • 5.5 Baths
  • 7,569 Sq Ft

  50 North St, Greenwich, CT 06830

  Nestled in the heart of Greenwich, this classic 1905 Victorian home sits on an oversized 0.96 acre flat lot with mature trees. High ceilings, expansive rooms & private terraces exude timeless elegance. This spacious home features 5 bedrooms, 5 1/2 bathrooms & two-car garage with port cochere. The sports court, pool & pool house welcome you home for a relaxing day. Enjoy your front porch, where

  Danielle Claroni Sotheby's International Realty

  50 North St, Greenwich, CT 06830
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  $899,000 Open Sun 11AM - 1PM

  • 5 Beds
  • 3.5 Baths
  • 2,261 Sq Ft

  73 Maitland Rd, Stamford, CT 06906

  Welcome to 73 Maitland Road, a stunning 5-bedroom, 3.5-bath home in Stamford that's been completely reimagined for modern living. The main level offers two bedrooms, a brand-new kitchen with quartz countertops and soft-close cabinetry, and sliders that open to a brand-new Trex deck overlooking a private flat backyard-perfect for entertaining or relaxing. Upstairs, you'll find a spacious primary

  Michael Spindler RE/MAX Right Choice

  73 Maitland Rd, Stamford, CT 06906
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  /30

  $4,300,000

  • 5 Beds
  • 5.5 Baths
  • 5,400 Sq Ft

  57 Lockwood Ave, Old Greenwich, CT 06870

  This beautifully scaled five-bedroom Colonial offers refined living in one of Old Greenwich's most coveted neighborhoods, just moments from the beach, park, train, schools and dining. Set on a meticulously landscaped 1/2 acre, the 5400-square-foot sun-drenched five bedroom boasts a stone terrace, French doors, wraparound porch, butler's pantry, grand chef's kitchen with island open to the family

  Noah Finz Houlihan Lawrence

  57 Lockwood Ave, Old Greenwich, CT 06870
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  /19

  $3,995,000

  • 6 Beds
  • 4.5 Baths
  • 3,515 Sq Ft

  22 Tomac Ave, Old Greenwich, CT 06870

  Terrific Old Greenwich location with easy access to south of the village with sidewalks to town, school and train. This gracious Shore Colonial is on an over-sized o.46 acre level lot (FAR in the R-12 zone could allow 6,300+ sf home), is warm and welcoming with 5 bedrooms and 3 full baths PLUS an additional studio on the main level that could be used in so many ways, as a main floor bedroom,

  Jackie Hammock Coldwell Banker Realty

  22 Tomac Ave, Old Greenwich, CT 06870
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  /38

  $849,900 Open Sun 12PM - 2PM

  • 5 Beds
  • 2 Baths
  • 2,015 Sq Ft

  27 Crane Rd N, Stamford, CT 06902

  This spacious and charming 5 BR, 2 BA Cape is full of thoughtful updates, making it the perfect place to call home. Set on a corner lot in a quiet, walkable neighborhood just off Newfield Avenue, it offers both comfort and convenience for today's busy families. The beautifully landscaped yard, framed by a classic New England rock wall, is ideal for gardening, playtime, or summer barbecues. A

  Jeff Roberts William Pitt Sotheby's Int'l

  27 Crane Rd N, Stamford, CT 06902
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  /25

  $975,000

  • 6 Beds
  • 4 Baths
  • 2,980 Sq Ft

  117 Maple Ave, Stamford, CT 06902

  3-Family House Listing in the Cove Area, Stamford, CT Spacious Multi-Family Opportunity Near the Waterfront Welcome to a rare opportunity in the heart of the coveted Cove neighborhood of Stamford, Connecticut. This charming and meticulously maintained three-family residence offers the perfect blend of investment potential and comfortable living, just moments from the sparkling waters of Long

  Antonio LaRocca The LaRocca Group

  117 Maple Ave, Stamford, CT 06902
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  /40

  $1,195,000

  • 8 Beds
  • 4.5 Baths
  • 3,019 Sq Ft

  39 North St, Stamford, CT 06902

  4-Family at 39 North St, Downtown Stamford, CT Prime Investment Opportunity in the Heart of Stamford Rare 4-family property ideally located at 39 North St, right in vibrant downtown Stamford! This well-maintained multi-family offers spacious units with excellent rental history and great income potential. Each apartment features bright living areas, updated kitchens, and separate utilities.

  Antonio LaRocca The LaRocca Group

  39 North St, Stamford, CT 06902
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  /40

  $725,000

  • 5 Beds
  • 3 Baths
  • 1,768 Sq Ft

  19 Waverly Place, Stamford, CT 06902

  OFFER DEADLINE - Wednesday, September 3 @ Noon. Looking for a turn-key multi-family just steps from Downtown Stamford? Welcome to 19 Waverly Place! This well-maintained 2-family home features two spacious, up/down style units, each offering 2 bedrooms, 1 bathroom, updated kitchens, and comfortable living spaces. The basement provides plenty of storage along with laundry for the building. The

  Chris Balestriere William Raveis Real Estate

  19 Waverly Place, Stamford, CT 06902
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  /35

  $3,399,000

  • 5 Beds
  • 5.5 Baths
  • 4,300 Sq Ft

  20 Sound Beach Ave, Greenwich, CT 06870

  NEW BUILD in coveted Old Greenwich, close to BEACH! Greeted with Wide Plank White Oak hardwood floors and high end finishes throughout the home, it truly is a masterpiece. Open-concept Kitchen is full of gold accent fixtures and JennAir appliances, with a large waterfall Quartz Carrara Gold Island. Entertain your guests while admiring the electric heating fireplace in the living room which also

  Kaltrina Xhema-Latifi Higgins Group Greenwich

  20 Sound Beach Ave, Greenwich, CT 06870
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  /36

  $1,999,000 Open Sun 1PM - 3PM

  • 5 Beds
  • 4.5 Baths
  • 4,278 Sq Ft

  6 Walnut Ridge Ct, Stamford, CT 06905

  Exceptional NEW construction in a coveted mid-city location offers the perfect blend of luxury and convenience. 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

  Barbara Hickey William Pitt Sotheby's Int'l

  6 Walnut Ridge Ct, Stamford, CT 06905
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  /40

  $1,950,000

  • 6 Beds
  • 4.5 Baths
  • 4,210 Sq Ft

  12B Hickory Dr, Greenwich, CT 06831

  Experience luxury living in this beautifully updated home. Featuring a brand-new high-end kitchen with premium appliances, custom cabinetry, and elegant finishes, this residence blends timeless style with modern convenience. Throughout the home, new flooring, upgraded door hinges, and designer door handles add a refined touch. The newly renovated bathroom offers a spa-like retreat, while the

  Daminder Sawhney Berkshire Hathaway NE Prop.

  12B Hickory Dr, Greenwich, CT 06831
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  /42

  $1,950,000

  • 6 Beds
  • 4.5 Baths
  • 4,210 Sq Ft

  12 Hickory Dr Unit B, Greenwich, CT 06831

  Experience luxury living in this beautifully updated home. Featuring a brand-new high-end kitchen with premium appliances, custom cabinetry, and elegant finishes, this residence blends timeless style with modern convenience. Throughout the home, new flooring, upgraded door hinges, and designer door handles add a refined touch. The newly renovated bathroom offers a spa-like retreat, while the

  Daminder Sawhney BHHS New England Properties

  12 Hickory Dr Unit B, Greenwich, CT 06831
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  /31

  $945,000

  • 6 Beds
  • 3 Baths
  • 2,880 Sq Ft

  95 Frederick St, Stamford, CT 06902

  Take notice! Legal two family dwelling in sought after Cove section of Stamford. Each unit features four rooms, two good size bedrooms, one full bath, eat in kitchen. This can be used as a full investment property or you can occupy one floor and rent the other for positive cash flow. Enclosed porch, large level rear yard with shed, close to many local businesses. Don't miss this one, this could

  Rosania Melo Century 21 Scala Group

  95 Frederick St, Stamford, CT 06902
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  /29

  $2,350,000

  • 5 Beds
  • 4 Baths
  • 3,897 Sq Ft

  76 Deepwood Rd, Darien, CT 06820

  Set on a full acre in one of Darien's most sought-after neighborhoods, this property presents a rare and versatile opportunity for visionary buyers. Whether you choose to undertake a renovation-reviving the charm of mid-century modern design-or build a custom new construction estate from the ground up, the potential here is extraordinary. Surrounded by multi-million dollar homes, this centrally

  Carolyn Brook William Pitt Sotheby's Int'l

  76 Deepwood Rd, Darien, CT 06820
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  /39

  $9,500,000

  • 8 Beds
  • 9 Baths
  • 10,328 Sq Ft

  31 Sawmill Ln, Greenwich, CT 06830

  Extraordinary 3+acre Greenwich mid country estate in a bucolic & private setting, situated within close proximity to downtown Greenwich. Available exclusively as furnished rental as well. This recently renovated & elegantly furnished stone Georgian Colonial blends timeless character with modern aesthetics. This substantial home features gracious & luxurious living spaces, ideal for entertaining

  Kevin Sneddon Compass Connecticut, LLC

  31 Sawmill Ln, Greenwich, CT 06830
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  /2

  $739,900

  • 5 Beds
  • 3 Baths
  • 1,732 Sq Ft

  41 Young Dixon Way, Stamford, CT 06902

  Excellent Investment property with Income potential,This legal 3 Family home is located on the West Side of Stamford,CT. Convenient to Train Station,I95 and walking distance to shops,hospital,parks and restaurants. Currently rented all tenants on month to month. Showings Monday through Saturday Only. This property is being sold as-is and the buyer must do their own due-diligence.

  Jacqueline Castro Keller Williams Prestige Prop.

  41 Young Dixon Way, Stamford, CT 06902
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  /37

  $8,490,000

  • 5 Beds
  • 7 Baths
  • 4,448 Sq Ft

  10 W Crossway, Old Greenwich, CT 06870

  See Video....Welcome to your dream vacation-like setting! This bright and spacious 5 bed 7 bath property boasts a tranquil ambiance with stunning sunsets that will take your breath away. Perfect for cozy evenings looking at the water. Multiple options for offices including bonus space above the garage are the perfect Zoom refuge. Entertain and relax on the inviting patios while taking in the

  Christian Perry Sotheby's International Realty

  10 W Crossway, Old Greenwich, CT 06870

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