Homes for Sale in Old Greenwich, CT with 5-Bedrooms

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  /86

  $23,000,000

  • 5 Beds
  • 7 Baths
  • 7,400 Sq Ft

  58 Shore Rd, Old Greenwich, CT 06870

  You don't look at your home...you look out from it.Set directly on the waterfront in Old Greenwich, this newly constructed residence is a masterclass in design, engineering and execution where every material, finish and feature was selected without compromise. Beyond a long, privately gated drive, sweeping cove views unfold, leading to a façade clad in premium Thermory wood siding beneath a

  

  Danielle Malloy

  Serhant Connecticut LLC

  (475) 253-5714

  58 Shore Rd, Old Greenwich, CT 06870
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  /31

  $21,000,000

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

  8 Fox Run Ln, Greenwich, CT 06831

  Perfectly sited on a quiet lane minutes from Greenwich Avenue, this 2024 SBP home offers serenity on nearly 5.5 gated acres. Walls of glass flood the interiors with natural light, highlighting 7'' white oak floors, a dramatic foyer, Calacatta marble fireplaces and Bocci lighting across 11,000+ sq ft. The open plan features a Bulthaup kitchen, living room with bar, and main-level bedroom suite or

  

  Megan Sullivan

  Douglas Elliman of Connecticut

  (475) 260-5961

  8 Fox Run Ln, Greenwich, CT 06831
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  /31

  $8,880,000

  • 6 Beds
  • 8 Baths
  • 7,718 Sq Ft

  15 Vineyard Ln, Greenwich, CT 06831

  Location, location, location! This stunning stone colonial sits on 2 park like acres just minutes from downtown Greenwich. With over 9,000 sq ft of beautiful living space, this 6-bedroom, 6.5-bath home offers graciously scaled rooms and an exceptional floor plan. The luxurious primary suite features a fireplace, dual bathrooms, and walk-in closets. Enjoy the spacious playroom over the garage, a

  

  Megan Sullivan

  Douglas Elliman of Connecticut

  (475) 265-6175

  15 Vineyard Ln, Greenwich, CT 06831
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  /37

  $1,050,000

  • 6 Beds
  • 3 Baths
  • 3,927 Sq Ft

  21 Hirsch Rd, Stamford, CT 06905

  This beautifully renovated two-family home in a highly desirable Stamford location is the one you've been waiting for. Conveniently situated near shopping, dining, entertainment, and transportation, it's just minutes from downtown Stamford and the train station. The first-floor unit features three spacious bedrooms, two full bathrooms, a bright living room, a dining area, and an eat-in kitchen.

  

  Hy Natarajan

  Keller Williams Prestige Prop.

  (475) 264-4148

  21 Hirsch Rd, Stamford, CT 06905
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  /47

  $6,250,000

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

  21 Calhoun Dr, Greenwich, CT 06831

  Welcome to ''Park Hill'', a reimagined 1923 English Manor in a Prestigious Private Association. Thoughtfully refreshed for modern living while preserving the architectural character that makes it timeless. Set on 1.81 private, park-like acres, this 7,632 sq. ft. manor blends historic charm with contemporary luxury in a way few properties can. 1923 English Tudor Revival with 2025 updates. Rare

  Danielle Claroni Sotheby's International Realty

  21 Calhoun Dr, Greenwich, CT 06831
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  /36

  $11,750,000 New Construction

  • 6 Beds
  • 9 Baths
  • 10,078 Sq Ft

  41 Mohawk Ln, Greenwich, CT 06831

  LUMEN HOUSE Set behind a private bridge on four gated acres of west-facing land, Lumen House is a 10,000+ square foot modern estate that transcends the ordinary. Conceived through a rare collaboration between Boutique Project Development, Atkins Construction Group, and the celebrated Vakota Architecture, this six-bedroom, nine-and-a-half-bath residence stands as one of Backcountry Greenwich's

  Jeffrey Jackson Corcoran Centric Realty LLC

  41 Mohawk Ln, Greenwich, CT 06831
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  /42

  $4,995,000

  • 5 Beds
  • 6 Baths
  • 5,482 Sq Ft

  7 Bailiwick Rd, Greenwich, CT 06831

  This stunning new construction filled with natural light features an open floor plan and soaring ceilings. The three -story foyer leads into an expansive living room, elegant formal dining room with access to the bluestone deck and a generous family room. Spectacular kitchen boasts top of the line sub-zero and wolf appliances, two large islands, skylights, a bright breakfast area and built-in

  Maria Ruggeberg William Raveis Real Estate

  7 Bailiwick Rd, Greenwich, CT 06831
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  /8

  $8,995,000 New Construction

  • 6 Beds
  • 10 Baths
  • 10,216 Sq Ft

  2 Stillman Ln, Greenwich, CT 06831

  Exceptional 2026 new construction offering resort-style living across a main residence + pool house on a private one-acre lot close to town. Designed by Schettino, the main house features 5 bedrooms, 7 full baths + 2 powder rooms with a seamless, light-filled floor plan ideal for entertaining and everyday living. The second floor incl a luxurious primary suite w balcony, dual walk-in closets, +

  Amanda Bates Houlihan Lawrence

  2 Stillman Ln, Greenwich, CT 06831
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  /58

  $8,495,000

  • 6 Beds
  • 10 Baths
  • 8,704 Sq Ft

  7 Calhoun Dr, Greenwich, CT 06831

  This timeless estate, situated in an exclusive private association moments from town, masterfully blends turn-of-the-century grandeur with 21st-century luxury. Extensively renovated and expanded in 2006 by the award-winning architects Austin Patterson Disston and lovingly updated by current owners to the same impeccable standards, this residence showcases grand-scale rooms, soaring ceilings, and

  Victoria Thorman Sotheby's International Realty

  7 Calhoun Dr, Greenwich, CT 06831
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  /30

  $8,750,000

  • 5 Beds
  • 8 Baths
  • 9,619 Sq Ft

  10 Birch Ln, Greenwich, CT 06830

  Impeccably constructed colonial in Greenwich's Golden Triangle on 1.35 acres with pool bordered by a scenic pond. A double-height foyer leads to the formal living room and library, both with fireplaces. Chef's kitchen adjoins the family room with fireplace, butler's pantry, and formal dining room. French doors open to terrace with heated pool, barbecue and firepit. Mudroom and attached 4-car

  Joseph Barbieri Sotheby's International Realty

  10 Birch Ln, Greenwich, CT 06830
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  /26

  $5,800,000

  • 5 Beds
  • 3.5 Baths
  • 4,324 Sq Ft

  8 Indian Point Ln, Riverside, CT 06878

  Tucked within the secluded Indian Point Association, this 1.55-acre waterfront sanctuary in coveted Riverside invites you to imagine the lifestyle that you have always wanted. From its sweeping southwestern vantage point, the property opens to mesmerizing views of Long Island Sound-a living canvas that shifts with every season, every tide, every change of light. A charming 1949 built house sits

  Patte Nusbaum Sotheby's International Realty

  8 Indian Point Ln, Riverside, CT 06878
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  /34

  $11,250,000

  • 6 Beds
  • 6 Baths
  • 5,638 Sq Ft

  200 Shore Rd, Old Greenwich, CT 06870

  Old Greenwich, Connecticut · Lucas Point · Long Island Sound. Where the Sound sets the rhythm. At 200 Shore Road, the water is not just a view, it is a way of life. Mornings arrive with a stillness only the Sound can offer, as light dances across the water and every moment feels slowed, softened, intentional. This Nantucket inspired residence is designed entirely around that experience, from the

  Angela Swift Compass Connecticut, LLC

  200 Shore Rd, Old Greenwich, CT 06870
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  /36

  $6,600,000

  • 6 Beds
  • 5.5 Baths
  • 6,987 Sq Ft

  11 Alden Rd, Greenwich, CT 06831

  Masterfully restored English stone manor, set on one of the prettiest neighborhoods in Greenwich, with close proximity to downtown. Originally built in 1928 using the finest craftsmanship and materials. The home features concrete structural walls for enduring strength and fantastic acoustics absent in more modern construction. A timeless slate roof and an exterior of hand laid local stone -

  Robert Johnson Brown Harris Stevens CT, LLC

  11 Alden Rd, Greenwich, CT 06831
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  /21

  $5,995,000

  • 7 Beds
  • 6 Baths
  • 6,797 Sq Ft

  251 Palmer Hill Rd, Greenwich, CT 06870

  Stonycrest -- A magnificent stone and shingle Victorian, completely and masterfully transformed while honoring its original architectural grandeur. Soaring high ceilings, exquisite millwork, and timeless character meet every modern amenity in this one-of-a-kind 7-bedroom residence. The stunning renovation showcases a spectacular new chef's kitchen, butler's pantry, and mudroom -- all with heated

  B.K. Bates Houlihan Lawrence

  251 Palmer Hill Rd, Greenwich, CT 06870
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  /43

  $5,950,000

  • 5 Beds
  • 5.5 Baths
  • 6,233 Sq Ft

  164 Stanwich Rd, Greenwich, CT 06830

  Welcome to this exquisitely updated Colonial on 1.16 landscaped acres near Greenwich Country Club and minutes from town. A grand foyer with gleaming hardwood floors and sweeping staircase introduces the elegant interior. The main level includes a formal living room, dining room, two studies, and a gourmet kitchen with Wolf appliances, Palissandro marble, Thermador coffee station, a custom wet bar

  Jeffrey Jackson Corcoran Centric Realty LLC

  164 Stanwich Rd, Greenwich, CT 06830
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  /41

  $4,988,000

  • 5 Beds
  • 6.5 Baths
  • 5,428 Sq Ft

  2 Potter Dr, Greenwich, CT 06870

  Forget the compromise between city energy and coastal calm. This isn't just a home; it's a high-design lifestyle that blends convenience with style. Situated on a coveted private lane in the heart of Old Greenwich, this new construction masterpiece by North Star Development delivers a ''five minute lifestyle'' rarely found outside the city, with a feel comparable to neighborhoods like Park Slope

  Angela Swift Compass Connecticut, LLC

  2 Potter Dr, Greenwich, CT 06870
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  /27

  $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 in collaboration with the renowned Olmsted Brothers. The property is set on 2.95 beautifully landscaped lakeside acres. The residence reflects timeless English architecture with elegant rooflines, rich stonework and finely crafted detailing throughout.

  Deborah Huffard Houlihan Lawrence

  78 Khakum Wood Rd, Greenwich, CT 06831
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  /37

  $4,995,000

  • 6 Beds
  • 4.5 Baths
  • 4,775 Sq Ft

  17 Brookside Park, Greenwich, CT 06831

  Beautifully renovated six-bedroom English country estate blending classic stone and shingle architecture with modern luxury, ideally set on a private, level acre in a coveted in-town location. Tucked down a quiet private lane, this exceptional property offers privacy, and timeless charm. The heart of the home is a fully updated, state-of-the-art eat-in kitchen, seamlessly connected to a gracious

  Alexandra Friedman Compass Connecticut, LLC

  17 Brookside Park, Greenwich, CT 06831
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  /43

  $5,475,000

  • 5 Beds
  • 5.5 Baths
  • 4,780 Sq Ft

  159 Lake Ave, Greenwich, CT 06830

  This fabulous just completed new home with 5 bedrooms is conveniently located on lower Lake Avenue with a large fenced in yard and sidewalks to downtown Greenwich. High ceilings and tall windows provide fantastic natural light through the living space. Exquisitely finished at every turn with modern elements including glass railings, stunning stone selections, white oak flooring and sparkling

  Christopher Finlay Brown Harris Stevens CT, LLC

  159 Lake Ave, Greenwich, CT 06830
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  /36

  $6,700,000

  • 5 Beds
  • 8 Baths
  • 7,691 Sq Ft

  131 Pecksland Rd, Greenwich, CT 06831

  A rare and distinguished offering in mid-country Greenwich, an estate of architectural significance, ready to be reimagined for modern luxury living. The Helen C. Douglas house was designed by the renowned Twachtman Brothers, blending classic elegance with warmth, sophistication and scale. Set on 3.8 acres of beautifully landscaped, private grounds, the property features a pool, tennis court, and

  Kaori Higgins Higgins Group Greenwich

  131 Pecksland Rd, Greenwich, CT 06831
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  /31

  $5,150,000 Open Sat 12PM - 2PM

  • 6 Beds
  • 6.5 Baths
  • 6,364 Sq Ft

  110 Sheephill Rd, Riverside, CT 06878

  Perfectly designed and built to meet the needs of today's buyer. Move right into this brand new 6,500 SF luxury home on Bella Lane a new private cul-de-sac off Sheephill Road, built by renowned builder Lino Marcal. This high-design residence features 6 bedrooms plus office, 6.1 baths, high ceilings throughout, 4 fireplaces, wine cellar, media room, and a beautiful three-season porch. Primary

  Lin Lavery Coldwell Banker Realty

  110 Sheephill Rd, Riverside, CT 06878
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  /40

  $1,700,000 Open Sat 1PM - 3PM

  • 6 Beds
  • 5.5 Baths
  • 4,794 Sq Ft

  163 W Hill Rd, Stamford, CT 06902

  Spectacular estate in highly coveted Westover delivering luxury, scale, and versatility at every turn. Boasting 6 bedrooms and 5.5 baths, this exceptional home is designed to meet a wide range of needs-from comfortable everyday living to hosting grand, unforgettable events. Freshly painted throughout, it showcases a crisp, modern feel while maintaining timeless elegance. Built for entertaining,

  Todd Auslander Keller Williams Prestige Prop.

  163 W Hill Rd, Stamford, CT 06902
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  /30

  $1,699,999

  • 5 Beds
  • 3 Baths
  • 2,911 Sq Ft

  21 Amherst Rd, Riverside, CT 06878

  First Time on the Market!Set on a quiet, sought-after street, this spacious five-bedroom, three-bath split-level home spans 2,911 square feet of bright, comfortable space. The main level features an eat-in kitchen and a large open dining and family room with an electric fireplace, ideal for gathering and everyday living. Sliders off the dining and family area lead to a generous deck

  Angela Alfano Coldwell Banker Realty

  21 Amherst Rd, Riverside, CT 06878
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  /40

  $15,945,000

  • 6 Beds
  • 10 Baths
  • 11,211 Sq Ft

  30 Meadowcroft Ln, Greenwich, CT 06830

  Sited on over two acres of private, west-facing land in the heart of Greenwich's coveted Golden Triangle, this architectural modern masterpiece commands attention. Designed in collaboration with renowned architect William D. Earls, this 11,000+ sq ft six-bedroom estate showcases timeless design, masterful craftsmanship, and refined sophistication. Completed in 2018, the residence blends bold

  Jeffrey Jackson Corcoran Centric Realty

  30 Meadowcroft Ln, Greenwich, CT 06830
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  /36

  $2,160,000

  • 5 Beds
  • 4 Baths
  • 3,644 Sq Ft

  61 Hobson St, Stamford, CT 06902

  Set in Stamford's coveted Shippan Point waterfront community, this renovated home offers a flexible, livable layout. The main level features hardwood floors, a chef-caliber kitchen with high-end appliances and generous prep space, a large dining area, a comfortable living room, and a wraparound deck overlooking a private patio. Three nicely sized bedrooms on the main level include one of two

  Thaddea Sheridan William Raveis Real Estate

  61 Hobson St, Stamford, CT 06902
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  /54

  $3,125,000

  • 5 Beds
  • 5 Baths
  • 4,777 Sq Ft

  2 Daffodil Ln, Cos Cob, CT 06807

  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,

  Stephen Archino Sotheby's International Realty

  2 Daffodil Ln, Cos Cob, CT 06807
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  /4

  $900,000

  • 5 Beds
  • 2 Baths
  • 2,815 Sq Ft

  424 Willett Ave, Port Chester, NY 10573

  This two-family Colonial-style home features two bedrooms, two full baths, two eat-in kitchens, and a two-car garage. The information provided is estimated to the best of our abilities at this time.

  Todd Yovino Island Advantage Realty LLC

  424 Willett Ave, Port Chester, NY 10573
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  /26

  $999,000

  • 6 Beds
  • 3 Baths
  • 3,392 Sq Ft

  72 Alvord Ln, Stamford, CT 06902

  This very spacious two-family home offers 3,392 sq ft of living space. Unit 1 has 3 bedrooms, 2 baths, eat in kitchen, large living room with fireplace, hardwood floors, partially finished basement, and a 1 car garage. Unit 2 has 3 bedrooms, 1 bath, eat in kitchen, large living room, walk up attic, and hardwood floors. Each unit has its own hot water heater, furnace, separate utilities, and

  Calvin Darula William Raveis Real Estate

  72 Alvord Ln, Stamford, CT 06902
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  /2

  $1,550,000

  • 8 Beds
  • 8 Baths
  • 5,760 Sq Ft

  6 Lawn Ave, Stamford, CT 06902

  GREAT INVESTMENT OPPORTUNITY! 4- family building with steady rental income. Each unit has 2 bedrooms, 1 full and 1 half bath, washer/dryer in unit, full basement, and 2 parking spaces. This property is a short distance to Cove Island beach and park, downtown Stamford shops and restaurants, I 95, Metro North train station, and Chelsea Piers. The property offers great future value to re-build as

  Angela Abate William Raveis Real Estate

  6 Lawn Ave, Stamford, CT 06902
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  /44

  $18,500,000

  • 6 Beds
  • 9 Baths
  • 10,275 Sq Ft

  41 Meadow Wood Dr, Greenwich, CT 06830

  With breathtaking views of Long Island Sound, this custom-built Mediterranean-style home is nestled in an exclusive gated community known as Quarry Farm in Belle Haven. Featuring a terracotta-tiled roof, this luxurious home boasts 6-bedrooms and 6.3 baths on 4.7 acres of land. The central courtyard, which serves as the heart of the home, is surrounded by common living areas with extra-height

  Jennifer Ho Douglas Elliman of Connecticut

  41 Meadow Wood Dr, Greenwich, CT 06830
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  /34

  $8,250,000

  • 6 Beds
  • 9 Baths
  • 9,295 Sq Ft

  34 Dublin Hill Dr, Greenwich, CT 06830

  Ideally located on a picture-perfect cul-de sac, this Shingle Style house has had just one owner since it was built in 2005. A well-conceived 9,295 +/-SF floor plan comprises six bedrooms, seven full bathrooms and two powder rooms, plus five fireplaces. High ceilings invite an abundance of light, while exquisite millwork, rich hardwood floors and a desirable layout highlight the appealing

  Leslie McElwreath Sotheby's International Realty

  34 Dublin Hill Dr, Greenwich, CT 06830
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  /41

  $14,890,000

  • 5 Beds
  • 7 Baths
  • 6,069 Sq Ft

  4 Little Cove Ln, Old Greenwich, CT 06870

  Exceptional new construction waterfront home set on a private cul-de-sac in one of Old Greenwich's most desirable enclaves. This custom-built residence offers 180-degree unobstructed water views from every bedroom and living space, with beautiful NYC skyline views. Designed for modern coastal living, the home spans three levels with six decks and seamless indoor-outdoor flow. Walls of glass and

  Alexandra Robinson Corcoran Centric Realty LLC

  4 Little Cove Ln, Old Greenwich, CT 06870
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  /8

  $900,000

  • 8 Beds
  • 3 Baths
  • 2,520 Sq Ft

  51 Lincoln Ave, Stamford, CT 06902

  Great opportunity in the heart of Stamford! This spacious multi-family property at 51 Lincoln Ave features two 3-bedroom, 1-bath units, plus a finished basement with 2 bedrooms and 1 bath-offering flexibility for a variety of uses. The large driveway provides ample parking, and the prime location near Downtown, shopping, and dining adds to its appeal. Perfect for investors seeking strong cash

  Abdul Kader Guy Bocicaut Real Estate

  51 Lincoln Ave, Stamford, CT 06902
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  /39

  $24,900,000

  • 7 Beds
  • 8 Baths
  • 18,217 Sq Ft

  44 & 40 Mayo Ave, Greenwich, CT 06830

  Nestled within the prestigious Belle Haven, Fairholme Estate is a magnificent English Manor that exudes timeless elegance and grandeur. Set on 2.74 beautifully landscaped acres, this seven-bedroom masterpiece features a spectacular pool, gracious wraparound porch, formal gardens, and expansive lawns, complemented by a charming coachman's cottage. Meticulously preserved to honor its historic

  Joanne Mancuso Houlihan Lawrence

  44 & 40 Mayo Ave, Greenwich, CT 06830
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  /27

  $4,200,000 Coming Soon

  • 5 Beds
  • 3.5 Baths
  • 4,795 Sq Ft

  2 Sylvan Ln, Old Greenwich, CT 06870

  2 Sylvan Lane is the property you've been waiting for, set on one of the most admired streets in Old Greenwich. Fantastic curb appeal in a sought after private association moments from the beach, clubs and village. Bike with your family around the quiet neighborhood or down to the beach at Greenwich Point. Deeded water access at the end of the street! This elegant home has been recently

  Robert Johnson Brown Harris Stevens CT, LLC

  2 Sylvan Ln, Old Greenwich, CT 06870
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  /29

  $899,000

  • 5 Beds
  • 2 Baths
  • 2,146 Sq Ft

  103 Ledge Ln, Stamford, CT 06905

  The Ultimate Belltown Retreat "Welcome home to 103 Ledge Lane! This stunningly refreshed 5-bedroom residence offers a rare combination of space, privacy, and modern updates in one of Stamford's most desirable pockets. Featuring a separate-entry floor plan ideal for guests or Multigenerational living, plus a beautifully manicured yard that opens to nature. With updated appliances including washer

  Noor Ahmed RE/MAX Heritage

  103 Ledge Ln, Stamford, CT 06905
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  /46

  $1,350,000 Open Sat 12PM - 2PM

  • 5 Beds
  • 3 Baths
  • 2,538 Sq Ft

  18 Moshier St, Greenwich, CT 06831

  Rare and exceptional side-by-side two-family is being offered for the first time since being built!! Boasting true one-floor living in both residences. The front unit is a showstopper that was completely renovated and expanded with stylish finishes and modern comfort throughout in 2019 with 3-bedrooms and 2. full baths, family room with vaulted ceilings and gas FP. Gas heat and cooking. The

  Stephen Archino Sotheby's International Realty

  18 Moshier St, Greenwich, CT 06831
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  /49

  $7,595,000

  • 6 Beds
  • 8 Baths
  • 8,087 Sq Ft

  20 Sherwood Farm Ln, Greenwich, CT 06831

  Privately nestled in a coveted enclave just minutes from downtown, schools and amenities, this 8,000 sq ft home is thoughtfully curated with elevated design and the most exceptional luxury finishes. Meticulously reimagined and recently updated, this grand residence offers a large chef's kitchen, sunlit breakfast room and elegant living spaces that open seamlessly to a tranquil and private

  Cora Lynch-O'Meara Brown Harris Stevens CT, LLC

  20 Sherwood Farm Ln, Greenwich, CT 06831
• 

  

  /38

  $2,499,999 Open Sat 2PM - 3:30PM

  • 5 Beds
  • 4 Baths
  • 3,302 Sq Ft

  51 Glen Rd, Greenwich, CT 06830

  Close to town from this rare in-town Greenwich gem -- a corner lot home on a quiet cul-de-sac, just steps from Greenwich Avenue's shops, restaurants, and cafés, the Greenwich Library, renowned private schools including Brunswick School and Greenwich Academy, and minutes to Metro-North Greenwich Station, with effortless access to parks, the waterfront, and all that downtown Greenwich offers. This

  Monica Webster Douglas Elliman of Connecticut

  51 Glen Rd, Greenwich, CT 06830
• 

  

  /20

  $1,600,000

  • 6 Beds
  • 5 Baths
  • 2,550 Sq Ft

  61 Aberdeen St, Stamford, CT 06902

  This exceptional four-family house, located in a sought-after Stamford neighborhood, offers a unique blend of modern luxury and investment practicality. Situated just minutes from vibrant local shopping centers and easily accessible to major highways, it is a prime location for professionals and working families seeking both convenience and a suburban feel. The property is designed with a clear

  Scott Kadison Scott Kadison Real Estate

  61 Aberdeen St, Stamford, CT 06902

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