Old Greenwich, CT Homes

• 

  

  

  /16

  $777,000

  Open Sat 1PM - 3PM $62K PRICE DROP

  • 6 Beds
  • 3 Baths
  • 3,744 Sq Ft

  140 Terrace Ave, Port Chester, NY 10573

  Prime Mixed-Use Investment Opportunity in the Heart of Port Chester This 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 increases. The property also includes a highly versatile ground-floor

  

  Cosmo Iadanza

  E Realty International Corp

  140 Terrace Ave, Port Chester, NY 10573
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  /65

  Starting at $2,495

  Total Monthly Price

  • Studio - 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
• 

  $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 $688,238

  Last Listing Agent Max Dober Keller Williams Prestige Prop.

  36 Middlebury St, Stamford, CT 06902
• 

  Est $596,906

  Not Listed For Sale

  25 Adams Ave Unit 411, Stamford, CT 06902

  • 2 Beds
  • 2 Baths
  • 1,303 Sq Ft
  • Built 2007

  25 Adams Ave Unit 411, Stamford, CT 06902

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent MaryDana McCann Houlihan Lawrence
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  /16

  $589,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,335 Sq Ft

  850 E Main St Unit 504, Stamford, CT 06902

  Fully remodeled loft-style condominium in the heart of downtown Stamford. Located on the 5th floor, this spacious residence offers soaring vaulted ceilings, abundant natural light, and an open-concept layout designed for modern living. The updated kitchen features quartz countertops, stainless steel appliances, and a large island with seating that flows seamlessly into the living and dining

  

  Christopher Reid

  Coldwell Banker Realty

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

  

  /24

  $3,600 Per Month

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft
  • Apartment for Rent

  41 Southfield Ave, Stamford, CT 06902

  Spacious apartment in Stamford's up-and-coming Waterside neighborhood. SIGN ONE YEAR LEASE AND RECEIVE ONE-MONTH FREE RENT... This bright and functional unit features a flexible floor plan, an updated kitchen with quartz countertops, a subway tile backsplash, and stainless-steel appliances. Dedicated on-site parking and prime location near Metro-North, the marina, and restaurants.

  

  Glenn Marr

  Marr Caruso Realty Group

  41 Southfield Ave, 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 $2,658,803

  Last Listing Agent Angela Swift Compass Connecticut, LLC

  137 Shore Rd, Old Greenwich, CT 06870
• 

  Est $374,794

  Not Listed For Sale

  127 Greyrock Place Unit 1013, Stamford, CT 06901

  • 1 Bed
  • 1 Bath
  • 764 Sq Ft
  • Built 1987

  127 Greyrock Place Unit 1013, Stamford, CT 06901

  Last Sold Summary

  • 72 Days On Market

  Last Listing Agent Maritza Ruiz R Connecticut
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  /37

  $1,195,000

  $100K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,132 Sq Ft

  38 Doral Farm Rd, Stamford, CT 06902

  Nestled in the coveted Westover neighborhood of Stamford, this beautifully appointed single-family residence in the prestigious Doral Farm association offers an exceptional blend of privacy and low-maintenance living. Enjoy the lifestyle of a standalone home with the added convenience of maintenance-free grounds and outstanding amenities.Spanning approximately 3,132 square feet, this 3-bedroom,

  

  Robin Bartholomew

  Berkshire Hathaway NE Prop.

  38 Doral Farm Rd, Stamford, CT 06902
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  /29

  Starting at $2,065

  Total Monthly Price

  • Studio - 2 Beds

  101 Summer St, Stamford, CT 06901

  Experience the best of urban living at Park Square West! We are conveniently nestled in the heart of Downtown Stamford, Connecticut. Our prime location offers walking distances to Stamford Town Center, restaurants, and entertainment hot spots, placing you in the center of it all! Discover the exciting opportunities here at Park Square West.

  Park Square West

  

  101 Summer St, Stamford, CT 06901
• 

  $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 $794,923

  Last Listing Agent Evan Philippopoulos RE/MAX Right Choice

  52 Sachem Place, Stamford, CT 06902
• 

  Est $516,650

  Not Listed For Sale

  127 Greyrock Place Unit 502, Stamford, CT 06901

  • 2 Beds
  • 2 Baths
  • 1,038 Sq Ft
  • Built 1987

  127 Greyrock Place Unit 502, Stamford, CT 06901

  Last Sold Summary

  • 51 Days On Market

  Last Listing Agent David Johnson Brown Harris Stevens
• 

  

  /20

  $888,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,712 Sq Ft

  86 Birch St, Port Chester, NY 10573

  Nestled on a quiet cul-de-sac in the desirable Lyon Acres neighborhood, this immaculate ranch-style home offers comfortable living on a beautifully landscaped lot, approximately a half block from Lyon Park. The main living area features a floor-to-ceiling wood-burning stone fireplace, vaulted ceilings.The primary bedroom includes an en-suite bath. Two additional bedrooms are situated on the

  

  Kateryna Ulerio

  Houlihan Lawrence Inc.

  86 Birch St, Port Chester, NY 10573
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  /28

  $3,500 Per Month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  98 Southfield Ave Unit 105, Stamford, CT 06902

  Life your best life in this beautifully renovated waterfront home! Located in a first-class community with beautiful grounds, inground pool and garage + guest parking, this is a first-floor garden apartment overlooking the marina and boardwalk. Enjoy the open new kitchen with designer sea glass cabs, window-lined living room leading to the pretty patio, fabulous new bath, high ceilings, laminate

  

  Melanie Healey

  Coldwell Banker Realty

  98 Southfield Ave Unit 105, Stamford, CT 06902
• 

  $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 $333,392

  Last Listing Agent Adam Wagner Keller Williams Prestige Prop.

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

  Est $517,743

  Not Listed For Sale

  118 Grove St Unit 7, Stamford, CT 06901

  • 2 Beds
  • 2.5 Baths
  • 1,302 Sq Ft
  • Built 1988

  118 Grove St Unit 7, Stamford, CT 06901

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Todd Auslander Keller Williams Prestige Prop.
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  /41

  $2,995,000

  $205K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,599 Sq Ft

  64 Wallacks Dr, Stamford, CT 06902

  Welcome to Wallack's Point - Stamford's most prestigious waterfront enclave. Situated on 1.25 acre with nearly 100 ft of direct LI Sound frontage, this extraordinary former boathouse has been transformed into a remarkable luxury compound. Defined by striking architectural design, soaring walls of glass, and sweeping water views, the property seamlessly blends sophisticated interiors with

  

  Suzette Kraus

  Compass Connecticut, LLC

  64 Wallacks Dr, Stamford, CT 06902
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  /29

  Starting at $2,772

  Total Monthly Price

  • Studio - 3 Beds

  18 Dock St, Stamford, CT 06902

  18 Dock is Stamford's newest standard of sophistication. Tailored with your lifestyle in mind, our exquisitely crafted apartments, ranging from studio to 3 bedrooms, redefine luxury living. Indulge in an oasis with resort-style amenities, offering an unrivaled experience. With convenient transportation access and thoughtfully designed living spaces adorned with lavish finishes, bespoke details,

  18 Dock Apartments

  18 Dock St, Stamford, CT 06902
• 

  

  /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
• 

  Est $1,240,174

  Not Listed For Sale

  1 Shore Rd Unit 14, Stamford, CT 06902

  • 3 Beds
  • 2.5 Baths
  • 1,746 Sq Ft
  • Built 1992

  1 Shore Rd Unit 14, Stamford, CT 06902

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Margaret Dietz Berkshire Hathaway NE Prop.
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  /35

  $694,000

  Open Sat 1PM - 3PM $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

  

  Todd Auslander

  Keller Williams Prestige Prop.

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

  

  /12

  $2,200 Per Month

  • 1 Bath
  • 468 Sq Ft
  • House for Rent

  140 Grove St Unit 5J, Stamford, CT 06901

  Exceptionally Sunny + Accommodating Downtown Studio! RENT INCLUDES: Heat, Hot Water, Assigned Parking & Cooking Gas! Get Ready to Enjoy life in the heart of vibrant Downtown Stamford in this newly renovated 5th floor apartment in a secure mid-rise building. This tucked away space features an open flow with extra windows, new flooring, a modern white kitchen and excellent storage/closet space!

  

  Melanie Healey

  Coldwell Banker Realty

  140 Grove St Unit 5J, Stamford, CT 06901
• 

  

  /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 $1,324,851

  Last Listing Agent Stephen Archino Sotheby's International Realty

  55 Byram Terrace Dr Unit B, Greenwich, CT 06831
• 

  Est $327,456

  Not Listed For Sale

  426 Courtland Ave Unit 1, Stamford, CT 06906

  • 2 Beds
  • 1 Bath
  • 819 Sq Ft
  • Built 1920

  426 Courtland Ave Unit 1, Stamford, CT 06906

  Last Sold Summary

  • 123 Days On Market

  Last Listing Agent omar arce Marr Caruso Realty Group
• 

  

  /23

  $324,900

  Open Sun 11AM - 1PM $5K PRICE DROP

  • 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

  

  Urs Klarer

  Coldwell Banker Realty

  34 Crescent St Unit 1D, Stamford, CT 06906
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  /69

  Starting at $2,613

  Total Monthly Price

  • Studio - 3 Beds

  150 Southfield Ave, Stamford, CT 06902

  Enjoy our state-of-the-art 2-level athletic club with Matrix Series 7xi equipment, outdoor swimming pool facing the harbor, and indoor basketball and racquetball courts. Relax in the cafe lounge with fresh coffee and Wi-Fi or take a walk on our scenic boardwalk overlooking Stamford Harbor. Walk along the boardwalk and enjoy all of the restaurants Stamford Harbor has to offer. Enjoying an

  TGM Anchor Point

  

  150 Southfield Ave, 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
• 

  Est $242,140

  Not Listed For Sale

  24 Home Ct Unit 7, Stamford, CT 06902

  • 1 Bed
  • 1 Bath
  • 587 Sq Ft
  • Built 1945

  24 Home Ct Unit 7, Stamford, CT 06902

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Richard Wilson Coldwell Banker Realty
• 

  

  /55

  $3,495,000

  Open Sun 11AM - 1PM

  • 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

  

  Danielle Malloy

  Serhant Connecticut LLC

  89 Indian Field Rd, Greenwich, CT 06830
• 

  

  /30

  $5,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,110 Sq Ft
  • Townhouse for Rent

  7 River Rd Unit 306, Cos Cob, CT 06807

  Location, location, location: Easy 5 minutes away from Cos Cob train station. Discover the beauty of waterfront living in this spacious 2-bedroom, 2-bathroom condominium at Palmer Point. Perfectly situated along the Mianus River, Unit 306 offers serene water views, a well-designed floor plan, and effortless access to all that Cos Cob has to offer. The sun-filled living and dining area is anchored

  

  Urs Klarer

  Coldwell Banker Realty

  7 River Rd Unit 306, Cos Cob, CT 06807
• 

  $295,000

  Sold Sep 04, 2025

  71 Strawberry Hill Ave Unit 1116, Stamford, CT 06902

  • 2 Beds
  • 1 Bath
  • 875 Sq Ft
  • Built 1959

  Last Sold Summary

  • $337/SF
  • 34 Days On Market

  Current Estimated Value $313,978

  Last Listing Agent Marc Fraioli Realty ONE Group Connect

  71 Strawberry Hill Ave Unit 1116, Stamford, CT 06902
• 

  Est $1,317,866

  Not Listed For Sale

  996 Stillwater Rd, Stamford, CT 06902

  • 4 Beds
  • 2.5 Baths
  • 4,006 Sq Ft
  • Built 1978

  996 Stillwater Rd, Stamford, CT 06902

  Last Sold Summary

  • 72 Days On Market

  Last Listing Agent Lisa Bortz William Pitt Sotheby's Int'l
• 

  

  /24

  $1,695,000

  • Land
  • 17,424 Sq Ft
  • $4,237,500 per Acre

  25 Circle Dr, Greenwich, CT 06830

  A rare opportunity to create your dream home on this .40-acre parcel ideally situated on a quiet cul-de-sac in a sought-after neighborhood. The property offers the ability to build a custom residence of just over 5,000 square feet and is being offered with full architectural plans and an approved demolition permit already in place, providing a streamlined path to construction. Residents enjoy

  

  Danielle Malloy

  Serhant Connecticut LLC

  25 Circle Dr, Greenwich, CT 06830
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  /66

  Starting at $2,665

  Total Monthly Price

  • 1 - 2 Beds

  545-573 Bedford St, Stamford, CT 06901

  Located just steps from downtown Stamford's bustling Bedford Street retail, restaurant and entertainment corridor, Bedford Hall is a luxury rental community boasting sleek one and two bedroom residences. With a walk score of 95, you are truly in the center of it all. Bedford Hall features 12 expertly designed floor plans from sleek junior 1 bedroom to airy 2 bedroom apartments. These stylish

  Bedford Hall

  

  545-573 Bedford St, Stamford, CT 06901
• 

  $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 $1,567,452

  Last Listing Agent Todd Auslander Keller Williams Prestige Prop.

  163 W Hill Rd, Stamford, CT 06902
• 

  Est $562,237

  Not Listed For Sale

  202 Soundview Ave Unit 3, Stamford, CT 06902

  • 2 Beds
  • 1.5 Baths
  • 2,127 Sq Ft
  • Built 1977

  202 Soundview Ave Unit 3, Stamford, CT 06902

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Marilyn Boulware-Hewlett Coldwell Banker Realty
• 

  

  /22

  $795,000

  Under Contract

  • 2 Beds
  • 2 Baths
  • 1,027 Sq Ft

  107 Pemberwick Rd, Greenwich, CT 06831

  Unique and charming, this Sears kit home, model Collingwood from 1927, brings one back to a by-gone era. Located in the Pemberwick neighborhood, this unique home features beautiful woodwork and simple beauty. This inviting property is very near Pemberwick Park, offering direct access to tennis courts, baseball fields, basketball courts, open green space and nature trails - perfect for active

  

  Danielle Claroni

  Sotheby's International Realty

  107 Pemberwick Rd, Greenwich, CT 06831
• 

  

  /21

  $2,950 Per Month

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft
  • Apartment for Rent

  Unlisted Address

  Bright + Immaculate 3-bedroom home in the popular + convenient South End neighborhood features a sparkling new kitchen with stylish quartz countertops + luxury full bath, laminate flooring, central air conditioning, gas heat and generous, off-street parking. There is laundry in the lower level with additional space for storage! Ready for occupancy!

  

  Melanie Healey

  Coldwell Banker Realty

  Unlisted Address
• 

  $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 $2,604,417

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

  83 Sea Beach Dr, Stamford, CT 06902
• 

  Est $667,618

  Not Listed For Sale

  194 Courtland Ave, Stamford, CT 06906

  • 3 Beds
  • 2 Baths
  • 1,599 Sq Ft
  • Built 1940

  194 Courtland Ave, Stamford, CT 06906

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Robin Schultz The Agency

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