Colonial Homes for Sale in Old Greenwich, CT

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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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  /38

  $1,849,000

  • 4 Beds
  • 5 Baths
  • 5,079 Sq Ft

  231 Roxbury Rd, Stamford, CT 06902

  Timeless and charming, this home-originally built as a dairy farm in 1925-has been thoughtfully expanded and updated for modern living, offering over 5,000 sq ft of beautifully finished space on nearly one acre of private, park-like property.A welcoming wraparound porch invites you in, where hardwood floors throughout and fresh interior paint create a move-in ready feel. Generous room sizes and a

  

  Suzette Kraus

  Compass Connecticut, LLC

  (475) 265-8334

  231 Roxbury Rd, Stamford, CT 06902
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  /61

  $3,195,000

  • 4 Beds
  • 4.5 Baths
  • 4,113 Sq Ft

  14 Upland Dr, Greenwich, CT 06831

  Set on 1.6 beautifully landscaped acres in a coveted Greenwich location, this exceptional four-bedroom residence offers space, flexibility, and timeless appeal. A dramatic two-story entry with a sweeping balcony sets the tone, leading into an oversized step-down living room with a fireplace, abundant natural light, and doors that open seamlessly to a patio perfect for indoor-outdoor living and

  Roseann Benedict Compass Connecticut, LLC

  14 Upland Dr, 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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  /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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  /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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  /39

  $2,395,000

  • 3 Beds
  • 2.5 Baths
  • 1,717 Sq Ft

  13 Mortimer Dr, Old Greenwich, CT 06870

  Tucked away in one of Old Greenwich's most desirable settings, this beautiful, fully updated home offers a rare sense of privacy paired with effortless indoor-outdoor living. Thoughtfully renovated for modern living, the home features a bright, efficient layout, a level fenced yard, and a detached heated studio ideal for a home office. Set in a sought-after location, close to town, train, schools

  Edineia Bickerstaff Berkshire Hathaway NE Prop.

  13 Mortimer Dr, Old Greenwich, CT 06870
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  /37

  $3,795,000

  • 4 Beds
  • 3.5 Baths
  • 3,560 Sq Ft

  7 Waverly Rd, Darien, CT 06820

  LIVE THE PERPETUAL VACATION LIFE IN NOROTON BAY - Experience this chic, sun-drenched Beach Colonial, perfectly situated on an open double lot. Extensively remodeled, the home's bright, open configuration is designed for effortless year-round family living and entertaining. Enjoy seamless indoor-outdoor living with expansive terraces, professionally landscaped grounds, and a charming signature

  Robert Green William Pitt Sotheby's Int'l

  7 Waverly Rd, Darien, CT 06820
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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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  /30

  $4,995,000

  • 4 Beds
  • 3.5 Baths
  • 6,915 Sq Ft

  177 Indian Head Rd, Riverside, CT 06878

  One of Riverside's most coveted waterfront enclaves, this elegant colonial offers refined living with a sense of privacy and tranquility set on nearly 2 acres. A new cedar just completed in 2025. The first level features a living room with fireplace, expansive family room, formal dining room, and sunny gallery passageway with French doors. Access the secluded back patio from the open kitchen,

  Remy Cook Corcoran Centric Realty LLC

  177 Indian Head Rd, Riverside, CT 06878
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  /32

  $3,120,000

  • 3 Beds
  • 3.5 Baths
  • 3,512 Sq Ft

  403 Stanwich Rd, Greenwich, CT 06830

  Come see this total and complete renovation!. New design, expanded Sq ft, custom hand built kitchen, all new mechanicals, roof, siding, windows, baths, etc. New granite pool deck, private 1.23 acres on desirable Stanwich rd. location.

  Stephen Kane Sotheby's International Realty

  403 Stanwich Rd, Greenwich, CT 06830
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  /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
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  /4

  $2,525,000

  • 8 Beds
  • 3 Baths
  • 3,443 Sq Ft

  2646 Boston Post Rd, Darien, CT 06820

  Home with seasonal water views of Holly Pond. Present use: Boarding House. Sold "As Is".

  Angela Abate William Raveis Real Estate

  2646 Boston Post Rd, Darien, CT 06820
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  /35

  $3,145,000 Open Sat 11AM - 1PM

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

  20 Sound Beach Ave, Greenwich, CT 06870

  NEW BUILD in 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 has

  Kaltrina Xhema-Latifi Higgins Group Greenwich

  20 Sound Beach Ave, Greenwich, CT 06870
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  /35

  $2,700,000

  • 4 Beds
  • 3 Baths
  • 2,796 Sq Ft

  8 Seagate Rd, Darien, CT 06820

  Welcome to 8 Seagate Road, a rare opportunity to live in one of Dariens most sought after waterfront communities! Enjoy the views of Holly Pond from this custom built home, offering a terrific layout. The large living room offers built-in cabinetry, a cozy fireplace & leads to the formal dining room, both with beautiful water views! The bright kitchen is nicely sized, with quartz counters,

  Kevin Quick William Pitt Sotheby's Int'l

  8 Seagate Rd, Darien, CT 06820
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  /32

  $2,995,000

  • 5 Beds
  • 4.5 Baths
  • 4,446 Sq Ft

  18 Thomasina Ln, Darien, CT 06820

  Thoughtfully built and meticulously maintained, this five-bedroom colonial offers four finished levels of living on a highly desirable in-town cul-de-sac. Ideally located just moments from beaches, train, downtown Darien and Darien Commons the home blends convenience with a true neighborhood feel. The bright open layout features hardwood floors throughout, detailed millwork, and a spacious

  Robin Halsey Compass Connecticut, LLC

  18 Thomasina Ln, Darien, CT 06820
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  /35

  $3,375,000

  • 5 Beds
  • 3.5 Baths
  • 5,213 Sq Ft

  12 Ricki-Beth Ln, Old Greenwich, CT 06870

  Tucked at the end of a quiet cul-de-sac in coveted Hillcrest Park, this superbly renovated 5-bedroom, 3.1-bath Colonial offers 5,213 square feet of refined living on 1.11 manicured acres in the heart of Old Greenwich, CT. Close distance to top-rated North Mianus Elementary School and just minutes from the Old Greenwich train station, downtown shops, and the beach, this is the rare Greenwich

  Jeffrey Jackson Corcoran Centric Realty LLC

  12 Ricki-Beth Ln, Old Greenwich, CT 06870
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  /40

  $2,900,000

  • 5 Beds
  • 6 Baths
  • 4,966 Sq Ft

  1 Duffys Ln, Darien, CT 06820

  Welcome to One Duffy's Lane, an exceptional 5-bedroom, 4.2-bath residence offering 4,966 square feet of refined living space on a private .65-acre lot. Perfectly positioned at the entrance of a highly sought-after cul-de-sac, this home combines timeless design with modern comfort. A spacious two-story foyer welcomes you upon entry, featuring a sweeping staircase and dramatic ceiling heights.

  Eileen Murphy William Pitt Sotheby's Int'l

  1 Duffys Ln, Darien, CT 06820
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  /40

  $2,950,000 Open Sat 1PM - 3PM

  • 6 Beds
  • 3.5 Baths
  • 5,105 Sq Ft

  40 Rogers Rd, Stamford, CT 06902

  Tucked within Stamford's coveted Shippan Point, 40 Rogers Road presents a refined coastal offering just moments from the water. Thoughtfully reimagined, the residence blends timeless character with a comprehensive suite of recent upgrades, delivering a turnkey living experience. Sun-filled interiors offer well-proportioned spaces with seamless flow for everyday living and entertaining. The second

  Ryan Dichter Compass Connecticut, LLC

  40 Rogers Rd, Stamford, CT 06902
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  /34

  $3,345,000

  • 5 Beds
  • 4.5 Baths
  • 6,195 Sq Ft

  5 Middlesex Rd, Darien, CT 06820

  Step into a truly special offering- a stately New England home, thoughtfully RENOVATED and completely MOVE-IN READY. Conveniently located close to train, elementary school, downtown shopping/dining, and parks. South-facing and situated on over half an acre, this gracious residence offers 6,195 sqft of character, elegance, and modern convenience. The gourmet kitchen is thoughtfully appointed with

  Allison Santopietro William Raveis Real Estate

  5 Middlesex Rd, Darien, CT 06820
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  /40

  $2,495,000 Open Fri 11AM - 1PM

  • 7 Beds
  • 5.5 Baths
  • 6,268 Sq Ft

  31 Gray Farms Rd, Stamford, CT 06905

  31 Gray Farms Rd nails the wish list for today's buyer: new construction, high-end finishes, space to entertain, and a location that can't be beat. Over an acre in Stamford's Newfield area, the home is surrounded by other new builds and minutes to trains MetroNorth (NYC)/Amtrak, I-95, the Merritt Parkway, JCC, Sterling Farms, and houses of worship. Inside, a bright two-story foyer opens to an

  Jonathan Makovsky Compass Connecticut, LLC

  31 Gray Farms Rd, Stamford, CT 06905
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  /30

  $2,950,000

  • 5 Beds
  • 5.5 Baths
  • 4,539 Sq Ft

  44 Maple St, Darien, CT 06820

  Welcome to 44 Maple Street, a beautifully maintained and thoughtfully updated home in one of Darien's most convenient locations. Just half a mile from Noroton Heights' shops, dining, and train, this property makes everyday errands simple, and commuting a breeze. Originally built by Giannattasio builders in 2017 and enhanced with quality updates by Ruddy Builders, the home has been meticulously

  Amanda Spatola Houlihan Lawrence

  44 Maple St, Darien, CT 06820
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  /38

  $2,995,000

  • 4 Beds
  • 3.5 Baths
  • 4,348 Sq Ft

  7 Heusted Dr, Old Greenwich, CT 06870

  Set in the desirable Edgewater neighborhood, 7 Heusted Drive offers a flexible layout, multiple living options, and exceptional convenience in the heart of Old Greenwich.The home is designed to adapt to a variety of needs, with open, well-proportioned living spaces, high ceilings, and thoughtful detailing throughout. A central kitchen with a large island connects seamlessly to the main living

  Ashley Petraska William Raveis Real Estate

  7 Heusted Dr, Old Greenwich, CT 06870
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  /39

  $2,495,000

  • 4 Beds
  • 3.5 Baths
  • 3,074 Sq Ft

  34 Macarthur Dr, Old Greenwich, CT 06870

  Located in sought-after Havemeyer Park, this 4BR, 3.5BA Colonial offers a bright, open layout centered around a dramatic, double-height living room with fireplace. The gourmet, eat-in kitchen opens to the dining room with sliders to a large deck overlooking a private, landscaped yard. A separate, sunny office provides a quiet work-from-home space, and a large family room completes the first

  Susan Isaak Coldwell Banker Realty

  34 Macarthur Dr, Old Greenwich, CT 06870
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  /40

  $910,000

  • 4 Beds
  • 1.5 Baths
  • 1,608 Sq Ft

  19 Burwood Ave, Stamford, CT 06902

  Welcome to 19 Burwood Avenue, a beautifully updated 4-bedroom home offering 1,608 square feet of comfortable living space in desirable Waterside neighborhood. This move-in ready property combines classic New England colonial charm with thoughtful upgrades, perfect for today's modern lifestyle. Inside, you'll find beautifully refinished hardwood floors that flow throughout, creating a warm and

  Peter Anderson Via Real Estate LLC

  19 Burwood Ave, Stamford, CT 06902
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  /25

  $699,000

  • 3 Beds
  • 1.5 Baths
  • 1,164 Sq Ft

  125 Oaklawn Ave, Stamford, CT 06905

  Ideally situated in a sought-after Stamford neighborhood, 125 Oaklawn Avenue offers a rare opportunity to create something special. Set on a well-maintained property, this home features sun-filled interiors and a comfortable flow for everyday living. The kitchen opens to the dining and living rooms, while the second floor includes three bedrooms and one full bath. A spacious, level backyard

  Kristen Studwell Compass Connecticut, LLC

  125 Oaklawn Ave, Stamford, CT 06905
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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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  /17

  $895,000

  • 2 Beds
  • 2 Baths
  • 1,227 Sq Ft

  28 Putnam Park Unit 28, Greenwich, CT 06830

  Sun-filled corner end unit in established Putnam Park community, ideally situated in central Greenwich. This spacious two-bedroom, two bath co-op offers refined single level living in a tranquil, park-like setting. With over 1200 square feet and three exposures, the home is filled with natural light. The open concept layout seamlessly connects the living and areas, while the updated kitchen

  Graham Gallagher Douglas Elliman of Connecticut

  28 Putnam Park Unit 28, Greenwich, CT 06830
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  /20

  $759,000

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  29 Putnam Green Unit 29, Greenwich, CT 06830

  Enjoy the ease of one-floor living in this bright two bedroom, two bath Co-op in the desirable Putnam Park Community. First time on the market in over 25 years, this unit is full of potential and ready for your personal touch, perfect to customize, renovate and make it your own. One of the rare units with four exposures. Bright and filled with natural light, this home features beautiful hardwood

  Frann Ward Houlihan Lawrence

  29 Putnam Green Unit 29, Greenwich, CT 06830
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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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  /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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  /39

  $1,599,000 Coming Soon

  • 4 Beds
  • 4 Baths
  • 4,943 Sq Ft

  33 Stone Wall Dr, Stamford, CT 06905

  Beautiful 4 bed 4 full bath colonial in Stamford's Highridge neighborhood. Built in 2006 and renovated this year. this property boasts new kitchen cabs and counters, new master bath, new first floor bathroom, new light and plumbing fixtures fixtures. Just in time for pool season!. enjoy BBQs with family and friends on the party deck and very private back yard and of course new gunite heated pool.

  Daniel Kolich William Raveis Real Estate

  33 Stone Wall Dr, Stamford, CT 06905
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  /18

  $815,000

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft

  233 Glenbrook Rd, Stamford, CT 06906

  This beautifully reimagined 4-bedroom, 3-bath home in Stamford's sought-after Glenbrook neighborhood blends timeless charm with modern living. Featuring a sun-filled open layout, soaring ceilings, and gleaming hardwood floors, this move-in-ready home offers effortless flow and comfort. With efficient upgrades, a private driveway, and a prime location just minutes from parks, schools, shopping,

  Natalia LLano Compass Connecticut, LLC

  233 Glenbrook Rd, Stamford, CT 06906
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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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  /34

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 2,172 Sq Ft

  30 Lenox Ave, Stamford, CT 06906

  Charming Colonial offering 3 bedrooms with additional finished attic space and a bonus room with full bath, providing flexibility for extended living, home office, or guest setup. The former garage has been converted into additional living space. Hardwood flooring throughout much of the home. Recent updates include a newer roof and a brand new hot water heater. Central air and natural gas

  Emiliano Navarro Keller Williams Realty

  30 Lenox Ave, Stamford, CT 06906
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  /40

  $1,250,000

  • 4 Beds
  • 2.5 Baths
  • 2,168 Sq Ft

  107 Barclay Dr, Stamford, CT 06903

  HIGHEST AND BEST BY MAY 5th, 5:00 pm. Tucked away on a quiet cul de sac just over the North Stamford border, 107 Barclay Drive is the fully renovated colonial you've been waiting for. Set on 1.17 acres with charming curb appeal and a welcoming front porch, this move-in ready 4 bedroom, 2.5 bath home blends style, space, and location. Filled with natural light, the home features refinished

  Staci Zampa Compass Connecticut, LLC

  107 Barclay Dr, Stamford, CT 06903
• 

  

  /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
• 

  

  /22

  $4,375,000

  • 5 Beds
  • 4.5 Baths
  • 3,384 Sq Ft

  118 Shore Rd, Old Greenwich, CT 06870

  Charming stone-front Shore Colonial ideally located south of Old Greenwich Village and on a quiet corner lot along desirable Ballwood Rd. This classically designed home offers 3 levels of relaxed, coastal living, featuring an open-concept kitchen and family room with expansive windows and doors that lead to a level, fenced backyard.Enjoy seamless indoor-outdoor entertaining with a large stone

  Tracey Koorbusch Sotheby's International Realty

  118 Shore Rd, Old Greenwich, CT 06870

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