61,672

Old Greenwich, CT Homes

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  • /35

    $694,000

    $26K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,636 Sq Ft

    2539 Bedford St Unit 38C, Stamford, CT 06905

    Welcome to The Chesterfield, one of Stamford's most iconic and sought-after condominium communities. Offering a lifestyle unlike any other, this gated, pet-friendly community features security, two swimming pools, a clubhouse, and beautifully maintained grounds. Freshly painted and move-in ready, this updated four-level townhome combines style, space, and convenience. The renovated kitchen

    Agent Photo

    Todd Auslander

    Keller Williams Prestige Prop.

    2539 Bedford St Unit 38C, Stamford, CT 06905
  • /65

    Starting at $2,915

    Total Monthly Price

    • 1 - 3 Beds

    850 Pacific St, Stamford, CT 06902

    Welcome to a new way of living on the waterfront. Allure offers luxury studio, 1, 2, 3 & 4 bedroom homes with elegance in each detail, spacious floorplans and spectacular views of Manhattan’s skyline. At Allure, experience the height of luxury living in Stamford.

    Allure @ Harbor Point

    850 Pacific St, Stamford, CT 06902
  • 36 Middlebury St, Stamford, CT 06902

    $651,700

    Sold Nov 07, 2025

    36 Middlebury St, Stamford, CT 06902

    • 3 Beds
    • 1 Bath
    • 1,365 Sq Ft
    • Built 1950

    Last Sold Summary

    • 9% Above List Price
    • $477/SF
    • 12 Days On Market

    Current Estimated Value $675,449

    Last Listing Agent Max Dober Keller Williams Prestige Prop.

    36 Middlebury St, Stamford, CT 06902
    • 58 Riverdale Ave, Greenwich, CT 06831

      Est $771,276

      Not Listed For Sale

      58 Riverdale Ave, Greenwich, CT 06831

      • 2 Beds
      • 1 Bath
      • 1,123 Sq Ft
      • Built 1926
      58 Riverdale Ave, Greenwich, CT 06831

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent Stefanie Lacoff Berkshire Hathaway NE Prop.

  • /39

    $712,985

    Pending
    • 5 Beds
    • 3 Baths
    • 2,358 Sq Ft

    224 Seaside Ave, Stamford, CT 06902

    INVESTORS & OWNER-OCCUPANTS TAKE NOTICE! Opportunity knocks with this spacious Stamford two-family offering an impressive 5 bedrooms, 4 full baths and approximately 2,358 square feet of living space. With two separate living spaces, this property offers tremendous flexibility-ideal as an income-producing investment, an owner-occupied home where rental income can help offset expenses, or a

    Agent Photo

    Susan Hanson

    William Raveis Real Estate

    224 Seaside Ave, Stamford, CT 06902
  • /17

    $3,100 Per Month

    • 2 Beds
    • 2 Baths
    • 1,188 Sq Ft
    • Townhouse for Rent

    49 Fairgate Dr, Stamford, CT 06902

    Located on the brim of vibrant downtown Stamford and in the heart of the popular Fairgate community, this newer townhome is so private + accommodating! Inside you'll find a designer kitchen with cool new granite countertops, opening to the large window-lined living-dining area featuring new laminate flooring + fresh paint. Upstairs you'll find 2 generous bedrooms, including a primary bedroom with

    Agent Photo

    Melanie Healey

    Coldwell Banker Realty

    49 Fairgate Dr, Stamford, CT 06902
  • /15

    $2,600,000

    Sold Dec 23, 2025

    137 Shore Rd, Old Greenwich, CT 06870

    • 4 Beds
    • 2.5 Baths
    • 2,214 Sq Ft
    • Built 1970

    Last Sold Summary

    • 5% Above List Price
    • $1,174/SF
    • 13 Days On Market

    Current Estimated Value $2,670,333

    Last Listing Agent Angela Swift Compass Connecticut, LLC

    137 Shore Rd, Old Greenwich, CT 06870
    • 30 Douglas Ave Unit 1, Stamford, CT 06906

      Est $799,313

      Not Listed For Sale

      30 Douglas Ave Unit 1, Stamford, CT 06906

      • 3 Beds
      • 3 Baths
      • 1,940 Sq Ft
      • Built 1915
      30 Douglas Ave Unit 1, Stamford, CT 06906

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Jason Kinard BHGRE Shore & Country

  • /24

    $196,500

    • 1 Bed
    • 1 Bath
    • 855 Sq Ft

    28 Courtland Ave Unit 1, Stamford, CT 06902

    Welcome to 28 Courtland Avenue, Unit 1, a thoughtfully maintained 1-bedroom, 1-bath co-op offering a spacious layout, abundant natural light, and move-in-ready living in Stamford. As an end unit, the home benefits from additional natural light that creates a bright and welcoming atmosphere throughout. Beautiful hardwood floors complement the generously sized living spaces, while the

    Agent Photo

    David Quito

    Modern Day Real Estate

    28 Courtland Ave Unit 1, Stamford, CT 06902
  • /168

    Starting at $3,345

    Total Monthly Price

    • 1 - 2 Beds

    880 Pacific St, Stamford, CT 06902

    Built with state-of-the-art infrastructure, our water-front resort-style amenities are inspired by the most sophisticated yachts from around the world. They will evoke pure joy and comfort, allowing you to connect with what truly matters. Relish in spacious open concept layouts paired with wood plank flooring, Silestone countertops, and full-size stainless-steel appliances. Escape offers one to

    Escape

    880 Pacific St, Stamford, CT 06902
  • 52 Sachem Place, Stamford, CT 06902

    $760,000

    Sold Nov 13, 2025

    52 Sachem Place, Stamford, CT 06902

    • 3 Beds
    • 3 Baths
    • 2,174 Sq Ft
    • Built 1957

    Last Sold Summary

    • 4% Above List Price
    • $350/SF
    • 17 Days On Market

    Current Estimated Value $788,605

    Last Listing Agent Evan Philippopoulos RE/MAX Right Choice

    52 Sachem Place, Stamford, CT 06902
    • 2435 Bedford St Unit 8C, Stamford, CT 06905

      Not Listed For Sale

      2435 Bedford St Unit 8C, Stamford, CT 06905

      • 2 Beds
      • 2.5 Baths
      • 2,211 Sq Ft
      • Built 1993
      2435 Bedford St Unit 8C, Stamford, CT 06905

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Donna Gilbert Keller Williams Realty

  • /38

    $775,000

    • 3 Beds
    • 1.5 Baths
    • 1,488 Sq Ft

    17 Alton Rd, Stamford, CT 06906

    Fall in love from the moment you step inside! Timeless character meets sophisticated modern style in this beautifully updated Stamford home, perfectly set on a picturesque, tree-lined street. Rich hardwood floors, graceful archways and glass-paneled doors create warmth and architectural charm, while stunning updates give this home the fresh, polished look today's buyers crave. The showstopping

    Agent Photo

    Todd Auslander

    Keller Williams Prestige Prop.

    17 Alton Rd, Stamford, CT 06906
  • /17

    $10,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,700 Sq Ft
    • Condo for Rent

    409 Greenwich Ave Unit A, Greenwich, CT 06830

    In-town living at its best! Incredible luxury apartment, with private rooftop terrace. Natural light bathes this 1,700 sq ft 2 bedroom 2.5 bath unit. Gourmet kitchen. High ceilings. Wide Plank floors. Views of Long Island Sound. Great location. Seconds from shopping, restaurants, Metro North and more.

    Agent Photo

    Michael Carey

    Sotheby's International Realty

    409 Greenwich Ave Unit A, Greenwich, CT 06830
  • 30 Maple Tree Ave Unit D, Stamford, CT 06906

    $315,000

    Sold Dec 09, 2025

    30 Maple Tree Ave Unit D, Stamford, CT 06906

    • 2 Beds
    • 1 Bath
    • 918 Sq Ft
    • Built 1969

    Last Sold Summary

    • 1% Below List Price
    • $343/SF
    • 35 Days On Market

    Current Estimated Value $335,881

    Last Listing Agent Adam Wagner Keller Williams Prestige Prop.

    30 Maple Tree Ave Unit D, Stamford, CT 06906
  • /97

    $19,995,000

    • 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

    Agent Photo

    Danielle Malloy

    Serhant Connecticut LLC

    58 Shore Rd, Old Greenwich, CT 06870
  • /64

    Starting at $2,322

    Total Monthly Price

    • Studio - 2 Beds

    65-77 Prospect St, Stamford, CT 06901

    Live, work, and play in Downtown Stamford. From culture to business, our apartment communities have something for everyone.An unbeatable location, luxurious amenities and remarkable value, Prospect Park redefines living in downtown Stamford. Enjoy all of the restaurants, shops, and café that downtown Stamford has to offer. Features include a stunning atrium, 9' ceilings*, quarts

    Prospect Park

    65-77 Prospect St, Stamford, CT 06901
  • /25

    $1,095,000

    Sold Jun 23, 2026

    40 W Elm St Unit 2M, Greenwich, CT 06830

    • 1 Bed
    • 1.5 Baths
    • 1,235 Sq Ft
    • Built 1939

    Last Sold Summary

    • $887/SF
    • 31 Days On Market

    Last Listing Agent Peter DaPuzzo Sotheby's International Realty

    40 W Elm St Unit 2M, Greenwich, CT 06830
  • /23

    $319,000

    $11K PRICE DROP Pending
    • 1 Bed
    • 1 Bath
    • 782 Sq Ft

    34 Crescent St Unit 1D, Stamford, CT 06906

    Urban Convenience Meets Modern Comfort: Pristine 1BR Stamford Condo Welcome home to this beautifully updated 1-bedroom, 1-bathroom condominium, where effortless living meets unbeatable location. Situated just one block from the train station, this property is a true commuter's dream. Step inside to find an open-concept, light-filled living area featuring engineered bamboo floors and crown

    Agent Photo

    Urs Klarer

    Coldwell Banker Realty

    34 Crescent St Unit 1D, Stamford, CT 06906
  • /24

    $5,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,165 Sq Ft
    • Townhouse for Rent

    27 Terrace Place Unit 1, Stamford, CT 06902

    Rare downtown Stamford rental! Built in 2021, this detached end-unit townhouse offers the privacy and feel of a single-family home with all the convenience of downtown living. Featuring 3 bedrooms, 2.5 baths and a bright open floor plan with high-end finishes throughout. The gourmet kitchen with pantry, high-end appliances, and an L-shaped countertop, opens to the living and dining area. The

    Agent Photo

    Seamus Costigan

    Marr Caruso Realty Group

    27 Terrace Place Unit 1, Stamford, CT 06902
  • /8

    $1,285,000

    Sold Apr 01, 2026

    55 Byram Terrace Dr Unit B, Greenwich, CT 06831

    • 2 Beds
    • 4 Baths
    • 2,601 Sq Ft
    • Built 2008

    Last Sold Summary

    • 1% Above List Price
    • $494/SF
    • 9 Days On Market

    Current Estimated Value $1,335,564

    Last Listing Agent Stephen Archino Sotheby's International Realty

    55 Byram Terrace Dr Unit B, Greenwich, CT 06831
    • 22 Palmer Ave, Stamford, CT 06902

      Est $971,798

      Not Listed For Sale

      22 Palmer Ave, Stamford, CT 06902

      • 5 Beds
      • 4 Baths
      • 4,005 Sq Ft
      • Built 1982
      22 Palmer Ave, Stamford, CT 06902

      Last Sold Summary

      • 87 Days On Market

      Last Listing Agent Nelly Patric Navarrete Keller Williams Prestige Prop.

  • /55

    $3,495,000

    • 5 Beds
    • 4.5 Baths
    • 5,354 Sq Ft

    89 Indian Field Rd, Greenwich, CT 06830

    Beautifully designed and thoughtfully finished, this exceptional New home blends sophisticated style with modern comfort and effortless everyday living. From the moment you enter, wide-plank French oak floors, 9-foot ceilings, Andersen windows, and curated designer details create a warm yet elevated atmosphere. The dining room and office make a statement with rich color-drenched finishes, while

    Agent Photo

    Danielle Malloy

    Serhant Connecticut LLC

    89 Indian Field Rd, Greenwich, CT 06830
  • /63

    Starting at $3,245

    Total Monthly Price

    • 1 - 2 Beds

    100-110 Commons Park N, Stamford, CT 06902

    Leasing Center now open. Experience Stamford’s best new place to call home, NV@ Harbor Point. NV offers new modern/industrial-inspired spaces featuring, reclaimed wood design plank flooring, 24-Hour Matrix Fitness gym, rooftop pool, grills, fire-pits as well as energy efficient appliances, walk-in closets and the spacious master bedroom that you deserve. NV@ Harbor Point offers an urban living

    NV @ Harbor Point

    100-110 Commons Park N, Stamford, CT 06902
  • /35

    $4,753,000

    Sold Apr 20, 2026

    24 Annjim Dr, Greenwich, CT 06830

    • 5 Beds
    • 4.5 Baths
    • 4,937 Sq Ft
    • Built 2001

    Last Sold Summary

    • 12% Above List Price
    • $963/SF
    • 5 Days On Market

    Last Listing Agent Amanda Bates Houlihan Lawrence

    24 Annjim Dr, Greenwich, CT 06830
    • 87 Charles St, Stamford, CT 06902

      Est $535,477

      Not Listed For Sale

      87 Charles St, Stamford, CT 06902

      • 3 Beds
      • 1 Bath
      • 912 Sq Ft
      • Built 1950
      87 Charles St, Stamford, CT 06902

      Last Sold Summary

      • 78 Days On Market

      Last Listing Agent Adam Wagner Keller Williams Prestige Prop.

  • /16

    $719,000

    $120K PRICE DROP
    • 6 Beds
    • 3 Baths
    • 2,476 Sq Ft

    140 Terrace Ave, Port Chester, NY 10573

    Owner is Motivated and has Authorized a Huge Price Reduction.Prime Mixed-Use Investment Opportunity in the Heart of Port ChesterThis well-located mixed-use building only 5 minutes away from Greenwich, CT. features two fully occupied residential units generating strong, consistent rental income, with current rents below market value—providing immediate upside potential through future

    Agent Photo

    Cosmo Iadanza

    E Realty International Corp

    140 Terrace Ave, Port Chester, NY 10573
  • /18

    $10,500 Per Month

    • 3 Beds
    • 3 Baths
    • 2,233 Sq Ft
    • Condo for Rent

    208 W Lyon Farm Dr Unit 208, Greenwich, CT 06831

    Sophisticated 2/3 BR, 3 BA townhome completely renovated in 2005 with quality finishes. Private home with terrace overlooking pond & gardens. 1st floor family room/den can double as a 1st floor bedroom (owner will modify the closets if needed). Eat-in gourmet kitchen w/custom cabinets by Dean. New windows. Luxurious primary bedroom w/large walk-in closet & newer bath w/steam shower. Just move-in

    Agent Photo

    Spencer Sodokoff

    Houlihan Lawrence

    208 W Lyon Farm Dr Unit 208, Greenwich, CT 06831
  • 72 Palmer Ave, Stamford, CT 06902

    $700,000

    Sold Sep 15, 2026

    72 Palmer Ave, Stamford, CT 06902

    • 3 Beds
    • 2 Baths
    • 1,656 Sq Ft
    • Built 1928

    Last Sold Summary

    • 5% Above List Price
    • $423/SF
    • 31 Days On Market

    Current Estimated Value $702,568

    Last Listing Agent Geri Guzinski William Pitt Sotheby's Int'l

    72 Palmer Ave, Stamford, CT 06902
    • 38 Catoona Ln, Stamford, CT 06902

      Est $777,414

      Not Listed For Sale

      38 Catoona Ln, Stamford, CT 06902

      • 5 Beds
      • 3 Baths
      • 2,732 Sq Ft
      • Built 1958
      38 Catoona Ln, Stamford, CT 06902

      Last Sold Summary

      • 62 Days On Market

      Last Listing Agent Nancy Manby William Raveis Real Estate

  • /24

    $569,900

    Open Sat 1PM - 3PM
    • 2 Beds
    • 2 Baths
    • 1,335 Sq Ft

    850 E Main St Unit 504, Stamford, CT 06902

    Fully remodeled, top-floor loft-style condominium in the heart of downtown Stamford. Soaring vaulted ceilings, abundant natural light, and an open-concept layout create a bright, spacious main living area. The second-floor loft features two separate rooms, currently configured as a home office and an additional bedroom, offering flexibility for working from home or hosting guests. The updated

    Agent Photo

    Christopher Reid

    Coldwell Banker Realty

    850 E Main St Unit 504, Stamford, CT 06902
  • /22

    Starting at $2,920

    Total Monthly Price

    • Studio - 2 Beds

    66 Summer St, Stamford, CT 06901

    Live virtual tours available. Call to schedule an appointment today and hear about our current discounts on select lines.

    66 Summer Street

    66 Summer St, Stamford, CT 06901
  • 163 W Hill Rd, Stamford, CT 06902

    $1,550,000

    Sold Jul 16, 2026

    163 W Hill Rd, Stamford, CT 06902

    • 6 Beds
    • 5.5 Baths
    • 4,794 Sq Ft
    • Built 1954

    Last Sold Summary

    • 9% Below List Price
    • $323/SF
    • 34 Days On Market

    Current Estimated Value $1,563,880

    Last Listing Agent Todd Auslander Keller Williams Prestige Prop.

    163 W Hill Rd, Stamford, CT 06902
    • 12 Deacon Hill Rd, Stamford, CT 06905

      Est $714,078

      Not Listed For Sale

      12 Deacon Hill Rd, Stamford, CT 06905

      • 3 Beds
      • 1.5 Baths
      • 1,539 Sq Ft
      • Built 1941
      12 Deacon Hill Rd, Stamford, CT 06905

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent William Hensley William Raveis Real Estate

  • /29

    $295,000

    • 1 Bed
    • 1 Bath
    • 891 Sq Ft

    70 Strawberry Hill Ave Unit 2-2B, Stamford, CT 06902

    Discover timeless charm and unbeatable convenience in this desirable pre-war building, perfectly situated in one of Stamford's most sought-after locations. Just moments from award-winning restaurants, premier shopping, theaters, Metro-North, I-95, and everything downtown has to offer, this spacious one-bedroom home is ideal for commuters and those seeking a vibrant urban lifestyle. Located on the

    Agent Photo

    Todd Auslander

    Keller Williams Prestige Prop.

    70 Strawberry Hill Ave Unit 2-2B, Stamford, CT 06902
  • /14

    $3,250 Per Month

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Townhouse for Rent

    16 Merrell Ave Unit 16, Stamford, CT 06902

    Sunny, spacious & pet-friendly, this contemporary townhome is located in convenient & desirable Greenfield! Situated on the brim of Greenwich & close to UCONN + downtown Stamford, living is bright and sunny here - enjoy an abundance of windows and space, including an "office/den" nook off the living room! The kitchen features stunning granite countertops, rich cabinetry and stainless steel

    Agent Photo

    Melanie Healey

    Coldwell Banker Realty

    16 Merrell Ave Unit 16, Stamford, CT 06902
  • 83 Sea Beach Dr, Stamford, CT 06902

    $2,650,000

    Sold Jun 04, 2026

    83 Sea Beach Dr, Stamford, CT 06902

    • 6 Beds
    • 6.5 Baths
    • 4,815 Sq Ft
    • Built 1930

    Last Sold Summary

    • 2% Below List Price
    • $550/SF
    • 10 Days On Market

    Current Estimated Value $2,625,982

    Last Listing Agent Carolyn Brook William Pitt Sotheby's Int'l

    83 Sea Beach Dr, Stamford, CT 06902
    • 300 Soundview Ave, Stamford, CT 06902

      Est $1,136,060

      Not Listed For Sale

      300 Soundview Ave, Stamford, CT 06902

      • 4 Beds
      • 2 Baths
      • 2,685 Sq Ft
      • Built 1949
      300 Soundview Ave, Stamford, CT 06902

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Richard Breglia Coldwell Banker Realty

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