Old Greenwich, CT Homes

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  /20

  $569,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,475 Sq Ft

  101 Grove St Unit 19, Stamford, CT 06901

  Enjoy a prime Downtown Stamford location with rare privacy and tranquility. Tucked away from the main road and overlooking a lush, serene courtyard, this townhouse-style home feels worlds away while remaining just steps from restaurants, shops, and Metro North. This well-maintained 2-bedroom, 2.5-bath residence features a distinctive multi-level layout where each floor serves its own purpose,

  

  Christopher Reid

  Coldwell Banker Realty

  (203) 884-0974

  101 Grove St Unit 19, Stamford, CT 06901
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  /28

  $2,200 per month

  • 1 Bed
  • 1 Bath
  • 610 Sq Ft
  • Apartment for Rent

  444 Bedford St Unit 6J, Stamford, CT 06901

  Sweeping city views from the entertainer's large (15 feet!) balcony in this immaculate & updated 6th floor condo in the heart of sophisticated downtown. Be the first to enjoy a bright new kitchen, drift-wood style laminate floors, separate sleeping alcove and living room with fabulous south-facing balcony overlooking the downtown cityscape. HEAT AND HOT WATER INCLUDED IN RENT. There is a small,

  

  Melanie Healey

  Coldwell Banker Realty

  (475) 255-2762

  444 Bedford St Unit 6J, Stamford, CT 06901
• 

  $1,100,000 Sold Jun 30, 2025

  37 Maplewood Dr, Cos Cob, CT 06807

  • 4 Beds
  • 4 Baths
  • 3,232 Sq Ft
  • Built 1961

  Last Sold Summary

  • 31% Below List Price
  • $340/SF
  • 122 Days On Market

  Current Estimated Value $1,186,864

  Last Listing Agent Kurt Jain NextHome Real Estate Services

  37 Maplewood Dr, Cos Cob, CT 06807
• 

  Not Listed For Sale

  2437 Bedford St Unit B6, Stamford, CT 06905

  • 2 Beds
  • 2 Baths
  • 1,199 Sq Ft
  • Built 1984

  2437 Bedford St Unit B6, Stamford, CT 06905

  Last Sold Summary

  • $486/SF
  • 7 Days On Market

  • Last Sold Price $583,000
  • Apr 17, 2025

  Last Listing Agent Len Schwartz Keller Williams Prestige Prop.
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  /27

  $1,100,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,368 Sq Ft

  1238 Westover Rd, Stamford, CT 06902

  After 40 years, this gracious split-level ranch on over two private acres is ready for its next chapter. With a versatile floor plan that lives like a five-bedroom home plus office, it offers exceptional flexibility for empty nesters seeking a main-level primary suite or families in need of generous space. The expansive living room, anchored by a brick wood-burning fireplace, flows into the

  

  Suzette Kraus

  Compass Connecticut, LLC

  (475) 260-0735

  1238 Westover Rd, Stamford, CT 06902
• 

  

  /15

  $2,700 per month

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

  678 Atlantic St Unit 3, Stamford, CT 06902

  Fully renovated 2 BR 1 BA apartment. Living room opens to an eat-in kitchen. New kitchen with quartz countertops and stainless steel appliances. Newly renovated bathroom with shower/tub. New floors throughout the apartment. Brand new washer and dryer in unit. 1 outdoor assigned parking spot. Located minutes from Stamford Train station, downtown Stamford, and tons of shops/restaurants. Unit is a

  

  Spencer Sodokoff

  Houlihan Lawrence

  (203) 487-5825

  678 Atlantic St Unit 3, 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 $640,964

  Last Listing Agent Max Dober Keller Williams Prestige Prop.

  36 Middlebury St, Stamford, CT 06902
• 

  Est $698,865 Not Listed For Sale

  564 Fairfield Ave, Stamford, CT 06902

  • 4 Beds
  • 2 Baths
  • 2,048 Sq Ft
  • Built 1920

  564 Fairfield Ave, Stamford, CT 06902

  Last Sold Summary

  • 5% Above List Price
  • $325/SF
  • 46 Days On Market

  • Last Sold Price $665,000
  • Apr 22, 2025

  Last Listing Agent Silvana Orsaia BHGRE Shore & Country
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  /29

  $1,849,999 Under Contract

  • 4 Beds
  • 4 Baths
  • 3,150 Sq Ft

  43 High St, Greenwich, CT 06830

  Ultra-stylish and completely reimagined in 2026, this home was rebuilt from the foundation up, creating an extraordinary 4-bedroom residence spanning 3 levels with a deck in an established neighborhood near trains, shops, & schools. Impeccable attention to space, detail & function with light wood floors, high ceilings, many custom elements, designer touches and smart home technology. Light-filled

  

  Spencer Sodokoff

  Houlihan Lawrence

  (475) 262-8302

  43 High St, Greenwich, CT 06830
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  /18

  $3,750 per month

  • 2 Beds
  • 1 Bath
  • 2,950 Sq Ft
  • House for Rent

  45 W North St Unit 2, Stamford, CT 06902

  Spacious 2-bedroom plus two rooms in a classic Victorian in Stamford's historic Hubbard Heights neighborhood at 45 W. North Street, Unit #2. This sun-drenched second-floor home offers 1,475 sq ft of living space filled with the kind of character and quirks only a Victorian can deliver - five skylights, a widow's peak with 360-degree panoramic views that serves as its own room, and an additional

  

  Peter Raider

  Real Broker CT, LLC

  (475) 335-8842

  45 W North St Unit 2, Stamford, CT 06902
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  /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 $2,573,132

  Last Listing Agent Angela Swift Compass Connecticut, LLC

  137 Shore Rd, Old Greenwich, CT 06870
• 

  Est $1,395,804 Not Listed For Sale

  222 Hubbard Ave, Stamford, CT 06905

  • 4 Beds
  • 3.5 Baths
  • 3,420 Sq Ft
  • Built 1927

  222 Hubbard Ave, Stamford, CT 06905

  Last Sold Summary

  • 3% Above List Price
  • $397/SF
  • 35 Days On Market

  • Last Sold Price $1,359,000
  • Apr 21, 2025

  Last Listing Agent Max Dober Keller Williams Prestige Prop.
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  /17

  $549,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,073 Sq Ft

  850 E Main St Unit 524, Stamford, CT 06902

  Fully remodeled condo in downtown Stamford. Located on the 5th floor, this unit offers vaulted ceilings, abundant natural light, and a bright open concept layout. The brand new kitchen features quartz countertops, stainless steel appliances, and a large island with seating, opening directly into the main living space. Both bathrooms have been fully remodeled with clean, modern finishes. This 2

  

  Christopher Reid

  Coldwell Banker Realty

  (475) 242-8629

  850 E Main St Unit 524, Stamford, CT 06902
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  /11

  $2,250 per month

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

  87 Glenbrook Rd Unit 3E, Stamford, CT 06902

  City living in the treetops! Located on the brim of vibrant & sophisticated downtown Stamford, this large, breezy 3rd floor corner unit offers super space, big windows, hardwood floors, a bright open kitchen and large, window-lined living room which opens to the private balcony. Spacious bedroom also opens to the balcony. Secure building & reserved parking. Included in rent is: Heat up to 55

  

  Melanie Healey

  Coldwell Banker Realty

  (475) 262-8150

  87 Glenbrook Rd Unit 3E, 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 $766,257

  Last Listing Agent Evan Philippopoulos RE/MAX Right Choice

  52 Sachem Place, Stamford, CT 06902
• 

  Est $469,686 Not Listed For Sale

  106 Holcomb Ave, Stamford, CT 06906

  • 2 Beds
  • 2 Baths
  • 1,122 Sq Ft
  • Built 1955

  106 Holcomb Ave, Stamford, CT 06906

  Last Sold Summary

  • 7% Above List Price
  • $392/SF
  • 37 Days On Market

  • Last Sold Price $440,000
  • Apr 18, 2025

  Last Listing Agent Thomas Langschultz S.E.L. Realty
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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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  /28

  $4,900 per month

  • 3 Beds
  • 2.5 Baths
  • 1,645 Sq Ft
  • Townhouse for Rent

  20 3rd St Unit 18, Stamford, CT 06905

  Welcome to this newer luxury Townhouse available for rent starting April 2026. This beautiful condo is minutes away from downtown Stamford and close to all amenities and public transportation. Have access to all that Stamford has to offer. The Townhouse has 3 lovely bedrooms and 2.5bathrooms. Beautiful finishes and hardwood floor throughout. Walk up to a very private rooftop deck with beautiful

  

  Hy Natarajan

  Keller Williams Prestige Prop.

  (475) 472-9321

  20 3rd St Unit 18, Stamford, CT 06905
• 

  $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 $319,532

  Last Listing Agent Adam Wagner Keller Williams Prestige Prop.

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

  Est $598,207 Not Listed For Sale

  177 Culloden Rd, Stamford, CT 06902

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft
  • Built 1924

  177 Culloden Rd, Stamford, CT 06902

  Last Sold Summary

  • 8% Above List Price
  • $380/SF
  • 19 Days On Market

  • Last Sold Price $556,000
  • Apr 22, 2025

  Last Listing Agent Kevin Quick William Pitt
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  /34

  $750,000 Under Contract

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft

  190 Toms Rd, Stamford, CT 06906

  Charming and beautifully updated Cape in Stamford's sought-after Glenbrook/Belltown neighborhood. This 3-bedroom, 3-bath home blends timeless character with modern comfort, featuring a welcoming front porch, formal living room with wood-burning fireplace, elegant dining room with French doors, and an open-concept kitchen with Corian counters, quartz-topped island, and new stainless-steel

  

  Toni Riordan

  Berkshire Hathaway NE Prop.

  (475) 256-5658

  190 Toms Rd, Stamford, CT 06906
• 

  

  /19

  $3,900 per month

  • 3 Beds
  • 2.5 Baths
  • 1,766 Sq Ft
  • Townhouse for Rent

  57 Dean St Unit 4, Stamford, CT 06902

  Beautiful, spacious open-concept townhouse featuring three bedrooms and two and a half bathrooms. This home offers a renovated kitchen with updated finishes, a bright and airy living and dining area perfect for entertaining, and a private balcony to enjoy your morning coffee. Convenient in-unit laundry and an attached garage add to the comfort and practicality of this wonderful home.

  

  Angela Araujo

  Keller Williams Realty

  (475) 260-7805

  57 Dean St Unit 4, Stamford, CT 06902
• 

  $1,120,000 Sold Jul 08, 2025

  77 Havemeyer Ln Unit 107, Stamford, CT 06902

  • 3 Beds
  • 3.5 Baths
  • 2,527 Sq Ft
  • Built 2013

  Last Sold Summary

  • 8% Below List Price
  • $443/SF
  • 16 Days On Market

  Current Estimated Value $1,195,046

  Last Listing Agent Robert Marchesi Compass Connecticut, LLC

  77 Havemeyer Ln Unit 107, Stamford, CT 06902
• 

  Est $786,559 Not Listed For Sale

  80 Victory St, Stamford, CT 06902

  • 4 Beds
  • 2 Baths
  • 1,908 Sq Ft
  • Built 1946

  80 Victory St, Stamford, CT 06902

  Last Sold Summary

  • 5% Above List Price
  • $393/SF
  • 82 Days On Market

  • Last Sold Price $750,000
  • Apr 23, 2025

  Last Listing Agent Kerry Ann Fahan Brown Harris Stevens
• 

  

  /22

  $888,000 Open Sun 1PM - 3PM

  • 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, and skylights that bring in abundant natural light.The primary bedroom includes an en-suite

  

  Kateryna Ulerio

  Houlihan Lawrence Inc.

  (914) 537-5822

  86 Birch St, Port Chester, NY 10573
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  /33

  $6,000 per month

  • 3 Beds
  • 2 Baths
  • 1,511 Sq Ft
  • House for Rent

  47 Hollow Tree Ridge Rd, Darien, CT 06820

  Owner will consider Unfurnished or partially furnished for longer term lease. A rare, unique "Nathaniel B. Weed" historic Antique Federal Colonial home in Darien, CT updated with modern conveniences. 3 BR, 2 BA townhouse- style unit where all levels are loaded with charm and character. Formal Living Room with woodstove, formal Dining Room, Updated Kitchen with walk-out to spacious deck. Primary

  

  Karen Finn

  Gatehouse Realty Inc

  (203) 403-2569

  47 Hollow Tree Ridge Rd, Darien, CT 06820
• 

  

  /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 $1,343,093

  Last Listing Agent Stephen Archino Sotheby's International Realty

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

  Est $899,250 Not Listed For Sale

  15 River Rd Unit 201, Cos Cob, CT 06807

  • 2 Beds
  • 2 Baths
  • 1,205 Sq Ft
  • Built 1979

  15 River Rd Unit 201, Cos Cob, CT 06807

  Last Sold Summary

  • 13% Above List Price
  • $663/SF
  • 17 Days On Market

  • Last Sold Price $799,000
  • Apr 17, 2025

  Last Listing Agent Annmarie Del Franco Blackstone Properties of 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
• 

  

  /17

  $11,000 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.

  

  Michael Carey

  Sotheby's International Realty

  (475) 267-1063

  409 Greenwich Ave Unit A, Greenwich, CT 06830
• 

  $750,000 Sold Jun 20, 2025

  47 Lafayette Place Unit 4C, Greenwich, CT 06830

  • 1 Bed
  • 1 Bath
  • 766 Sq Ft
  • Built 1956

  Last Sold Summary

  • 6% Below List Price
  • $979/SF
  • 30 Days On Market

  Last Listing Agent Jennifer Marrelli Compass Connecticut, LLC

  47 Lafayette Place Unit 4C, Greenwich, CT 06830
• 

  Est $2,540,973 Not Listed For Sale

  15 Chester Rd, Darien, CT 06820

  • 4 Beds
  • 3.5 Baths
  • 3,204 Sq Ft
  • Built 1939

  15 Chester Rd, Darien, CT 06820

  Last Sold Summary

  • 4% Above List Price
  • $765/SF
  • 21 Days On Market

  • Last Sold Price $2,450,000
  • Apr 18, 2025

  Last Listing Agent Kate Geerer Coldwell Banker Realty
• 

  

  /22

  $2,930,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,163 Sq Ft

  25 Woodland Dr Unit C, Greenwich, CT 06830

  Single-family home, positioned at the rear of Avenue Terrace, a private six-home enclave in Downtown Greenwich constructed by Orlando Development. Exceptionally bright family room, Sub-Zero and Wolf appliances, gas fireplace, custom built-ins, separate first-floor office, and space available for future elevator installation.Primary bedroom beamed ceiling, fully outfitted walk-in closet and

  

  Andrew Smith

  Houlihan Lawrence

  (475) 255-2547

  25 Woodland Dr Unit C, Greenwich, CT 06830
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  /15

  $2,400 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Townhouse for Rent

  2 Westwood Dr Unit 2, Stamford, CT 06902

  Tucked back from the road, 2 Westwood Drive has its own private entrance and the rent price is the actual price - WITH NO ADDITIONAL FEES. This Newer, very pretty apartment in sought after Westwood features an open designer kitchen with new granite countertops + stainless steel appliances, sunny rooms lined with large windows, cool, new laminate floors, central air, gas heat, excellent closet

  

  Melanie Healey

  Coldwell Banker Realty

  (475) 445-1636

  2 Westwood Dr Unit 2, Stamford, CT 06902
• 

  $660,000 Sold Jul 01, 2025

  1 Broad St Unit 10F, Stamford, CT 06901

  • 2 Beds
  • 2.5 Baths
  • 1,530 Sq Ft
  • Built 2009

  Last Sold Summary

  • 2% Below List Price
  • $431/SF
  • 65 Days On Market

  Current Estimated Value $678,118

  Last Listing Agent Holly Giordano William Pitt Sotheby's Int'l

  1 Broad St Unit 10F, Stamford, CT 06901
• 

  Not Listed For Sale

  44 Strawberry Hill Ave Unit 9P, Stamford, CT 06902

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft
  • Built 1969

  44 Strawberry Hill Ave Unit 9P, Stamford, CT 06902

  Last Sold Summary

  • $380/SF
  • 44 Days On Market

  • Last Sold Price $245,000
  • Apr 17, 2025

  Last Listing Agent Michael Carriero Keller Williams Realty
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  /35

  $1,999,000 Under Contract

  • 7 Beds
  • 5 Baths
  • 4,626 Sq Ft

  225 Washington Blvd, Stamford, CT 06902

  Exceptional turnkey investment opportunity in Stamford's premier waterfront Harbor Point neighborhood. This recently renovated income-producing property offers a rare blend of modern design, flexibility, and strong revenue potential in one of Fairfield County's most sought-after locations. Pro forma projections reflect an estimated 9+ cap at market rents, presenting a compelling opportunity for

  

  Arian Hoxha

  Serhant Connecticut, LLC

  (475) 405-1249

  225 Washington Blvd, Stamford, CT 06902
• 

  

  /12

  $4,200 per month

  • 4 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • House for Rent

  253 Hope St, Stamford, CT 06906

  Remodeled and Painted throughout Three level home. Pictures are not complete yet. A renovation costing over $40,000 was just completed. All lights have been upgraded to LED. New hardwood floors on second and third floor. First floor has New Vinyl floor. Third floor bedroom area is the entire floor and it can be made into two bedrooms. 4 bedrooms, 2 full baths, Washer Dryer Hook on first floor.

  

  Cosmo Iadanza

  Century 21 AllPoints Realty

  (475) 222-1655

  253 Hope St, Stamford, CT 06906
• 

  

  /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 $809,941 Not Listed For Sale

  108 Seaside Ave Unit 10, Stamford, CT 06902

  • 3 Beds
  • 3.5 Baths
  • 2,728 Sq Ft
  • Built 2014

  108 Seaside Ave Unit 10, Stamford, CT 06902

  Last Sold Summary

  • 2% Above List Price
  • $291/SF
  • 22 Days On Market

  • Last Sold Price $795,000
  • Apr 18, 2025

  Last Listing Agent Arlene Bubbico Coldwell Banker Realty

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