Old Greenwich, CT Homes

• 

  

  

  /27

  $2,100,000

  Pending

  • 4 Beds
  • 4 Baths
  • 3,986 Sq Ft

  14 Rockland Place, Greenwich, CT 06831

  Spacious Colonial with nearly 4,000 sq ft on a quiet cul-de-sac in the heart of Pemberwick. The bright main level offers a living room with a fireplace, an open eat-in kitchen with an island and breakfast bar, a pantry, a dining area, one bedroom, and a full bath. Upstairs features the primary suite with a walk-in closet and en-suite bath, two additional bedrooms, a hall bath, laundry, and a

  

  Juliana Serrao

  William Raveis Real Estate

  14 Rockland Place, Greenwich, CT 06831
• 

  

  

  /64

  Starting at $2,716

  Total Monthly Price

  • 1 - 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
• 

  $615,000

  Sold Oct 24, 2025

  42 Sylvan Knoll Rd, Stamford, CT 06902

  • 4 Beds
  • 1 Bath
  • 1,238 Sq Ft
  • Built 1948

  Last Sold Summary

  • 1% Above List Price
  • $497/SF
  • 55 Days On Market

  Current Estimated Value $662,912

  Last Listing Agent Glenn Marr Marr Caruso Realty Group

  42 Sylvan Knoll Rd, Stamford, CT 06902
• 

  Est $1,005,027

  Not Listed For Sale

  182 5th St, Stamford, CT 06905

  • 4 Beds
  • 3.5 Baths
  • 3,253 Sq Ft
  • Built 1947

  182 5th St, Stamford, CT 06905

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Rosalia Casorla Premier Re Group LLC
• 

  

  

  /24

  $599,000

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,478 Sq Ft

  78 Saint Charles Ave, Stamford, CT 06907

  Welcome to 78 Saint Charles Avenue, a well-maintained home offering comfort, convenience, and exceptional value in one of Stamford's most accessible neighborhoods. Whether you're a first-time homebuyer, downsizer, or investor, this property presents an outstanding opportunity to own in a location close to everything Stamford has to offer. Inside, you'll find a practical and functional floor plan

  

  Joseph Pasquino

  Compass Connecticut, LLC

  78 Saint Charles Ave, Stamford, CT 06907
• 

  

  /22

  $13,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,454 Sq Ft
  • Townhouse for Rent

  178 Milbank Ave Unit 2, Greenwich, CT 06830

  Premier downtown Greenwich location just moments from Greenwich Avenue, the train, restaurants, shopping, and parks. This elegant townhouse features a private elevator from the large attached garage, opening to a light-filled interior with soaring ceilings, oversized windows, and refined finishes. The main level offers a living room with a gas fireplace and custom built-ins, a dining room with

  

  Andrew Smith

  Houlihan Lawrence

  178 Milbank Ave Unit 2, Greenwich, CT 06830
• 

  $765,000

  Sold Apr 17, 2026

  91 Dann Dr, Stamford, CT 06905

  • 3 Beds
  • 2.5 Baths
  • 1,413 Sq Ft
  • Built 1955

  Last Sold Summary

  • 11% Above List Price
  • $541/SF
  • 13 Days On Market

  Current Estimated Value $754,547

  Last Listing Agent Nick Jaku William Raveis Real Estate

  91 Dann Dr, Stamford, CT 06905
• 

  Est $887,851

  Not Listed For Sale

  88 Horton St, Stamford, CT 06902

  • 6 Beds
  • 2 Baths
  • 2,728 Sq Ft
  • Built 1971

  88 Horton St, Stamford, CT 06902

  Last Sold Summary

  • 29 Days On Market

  Last Listing Agent Mike Feldman Century 21 AllPoints Realty
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  /28

  $2,200,000

  $200K PRICE DROP

  • 8 Beds
  • 4 Baths
  • 5,250 Sq Ft

  11 Columbus Ave, Greenwich, CT 06830

  Rare four-unit multi-family opportunity in Greenwich's Chickahominy neighborhood. 11 Columbus Ave offers 8 bedrooms and 4 bathrooms total across four separate units on a private lot, close to downtown Greenwich Avenue, Metro-North rail, and I-95/Merritt Parkway access. Offering approximately 5,250 square feet, with separate utilities/meters and off street parking. Each unit features 2 beds, 1

  

  Arian Hoxha

  Serhant Connecticut, LLC

  11 Columbus Ave, Greenwich, CT 06830
• 

  

  /63

  Starting at $2,715

  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
• 

  $595,000

  Sold Jun 12, 2026

  143 Hoyt St Unit 1N, Stamford, CT 06905

  • 2 Beds
  • 2 Baths
  • 1,836 Sq Ft
  • Built 1976

  Last Sold Summary

  • 8% Below List Price
  • $324/SF
  • 23 Days On Market

  Last Listing Agent Patricia Rattray William Pitt Sotheby's Int'l

  143 Hoyt St Unit 1N, Stamford, CT 06905
• 

  Est $863,817

  Not Listed For Sale

  306 Hubbard Ave, Stamford, CT 06905

  • 3 Beds
  • 1.5 Baths
  • 2,146 Sq Ft
  • Built 1928

  306 Hubbard Ave, Stamford, CT 06905

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent Barbara Hickey William Pitt Sotheby's Int'l
• 

  

  /29

  $470,000

  Pending

  • 3 Beds
  • 3 Baths
  • 1,680 Sq Ft

  50 Glenbrook Rd Unit 7C, Stamford, CT 06902

  Spacious and beautifully updated 3-bedroom, 3-bath residence in a desirable doorman building, offering stunning city views from the 7th floor. This open-concept home features gleaming hardwood floors throughout and two private balconies facing south/east and west-perfect for enjoying both sunrise and sunset. The renovated eat-in kitchen boasts granite countertops, stainless steel appliances, and

  

  Todd Auslander

  Keller Williams Prestige Prop.

  50 Glenbrook Rd Unit 7C, Stamford, CT 06902
• 

  

  /40

  $23,000 Per Month

  • 5 Beds
  • 7 Baths
  • 5,000 Sq Ft
  • House for Rent

  Unlisted Address

  Spectacular custom-built modern home in the heart of Old Greenwich. Flooded with natural light, this sophisticated residence features soaring ceilings, oversized windows, and seamless indoor-outdoor living throughout. The open-concept layout offers effortless flow for both everyday living and entertaining, a gourmet kitchen with an oversized island, a retractable screened porch, and a private

  

  Juliana Serrao

  William Raveis Real Estate

  Unlisted Address
• 

  $380,000

  Sold Sep 26, 2025

  65 Glenbrook Rd Unit 8B, Stamford, CT 06902

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft
  • Built 1964

  Last Sold Summary

  • 1% Below List Price
  • $284/SF
  • 75 Days On Market

  Last Listing Agent Ying Gao Golden Heights LLC

  65 Glenbrook Rd Unit 8B, Stamford, CT 06902
• 

  Est $850,920

  Not Listed For Sale

  48 Powell Place, Stamford, CT 06902

  • 3 Beds
  • 2.5 Baths
  • 2,430 Sq Ft
  • Built 1910

  48 Powell Place, Stamford, CT 06902

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Naima Mazouzi Eagle Eye Realty PLLC
• 

  

  /14

  $189,000

  Pending

  • 1 Bath
  • 563 Sq Ft

  30 Glenbrook Rd Unit 6C, Stamford, CT 06902

  SELLER REQUESTS HIGHEST AND BEST BY 7/15 AT 5PM. This bright + open 6th floor studio in the pulse of vibrant downtown Stamford is is remarkably spacious, filled with windows ~ flooded with sunshine + possibility! Aggressively priced and presented as a canvas to create your perfect space featuring an open living/dining area, fabulous cityscape and some water views, galley kitchen and separate

  

  Melanie Healey

  Coldwell Banker Realty

  30 Glenbrook Rd Unit 6C, Stamford, CT 06902
• 

  

  /22

  Starting at $2,604

  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
• 

  $803,000

  Sold Oct 03, 2025

  123 Harbor Dr Unit 311, Stamford, CT 06902

  • 2 Beds
  • 2.5 Baths
  • 1,525 Sq Ft
  • Built 1985

  Last Sold Summary

  • 10% Above List Price
  • $527/SF
  • 10 Days On Market

  Current Estimated Value $846,700

  Last Listing Agent Susan Pitkin-Rudnick William Raveis Real Estate

  123 Harbor Dr Unit 311, Stamford, CT 06902
• 

  Est $1,913,478

  Not Listed For Sale

  124 Westover Ln, Stamford, CT 06902

  • 5 Beds
  • 5.5 Baths
  • 6,458 Sq Ft
  • Built 1961

  124 Westover Ln, Stamford, CT 06902

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Evan Philippopoulos RE/MAX Right Choice
• 

  

  /37

  $1,039,500

  $11K PRICE DROP

  • 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.

  21 Hirsch Rd, Stamford, CT 06905
• 

  

  /26

  $6,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,422 Sq Ft
  • House for Rent

  49 Hollow Tree Ridge Rd, Darien, CT 06820

  Central A/C system. 3 BR, 2 BA townhouse-style unit where all three levels are loaded with charm and character. Features include a Mansard roof (tall ceilings on 2nd floor), wide plank flooring, hand hewn beams, multiple fireplaces, newer kitchen with stainless steel appliances and washer dryer in unit. French doors lead to bluestone patio overlooking large, private backyard with plenty of level

  

  Karen Finn

  Gatehouse Realty Inc

  49 Hollow Tree Ridge Rd, Darien, CT 06820
• 

  

  /21

  $1,035,000

  Sold Aug 11, 2025

  112 Greenwich Hills Dr, Greenwich, CT 06831

  • 3 Beds
  • 2.5 Baths
  • 2,112 Sq Ft
  • Built 1976

  Last Sold Summary

  • 4% Above List Price
  • $490/SF
  • 43 Days On Market

  Last Listing Agent Emily Klaeboe Cerussi Compass Connecticut, LLC

  112 Greenwich Hills Dr, Greenwich, CT 06831
• 

  Est $780,549

  Not Listed For Sale

  211 Cold Spring Rd, Stamford, CT 06905

  • 4 Beds
  • 3 Baths
  • 2,276 Sq Ft
  • Built 1926

  211 Cold Spring Rd, Stamford, CT 06905

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Irene Cheung BHGRE Shore & Country
• 

  

  /21

  $249,000

  Pending

  • 1 Bed
  • 1 Bath
  • 725 Sq Ft

  71 Strawberry Hill Ave Unit 1015, Stamford, CT 06902

  Own your piece of the Stamford Sky! UPTO $10,000.00 1st Time Home-buyer Benefit is Possible Here! Look down on creation from this bright + stylish 10th Floor apartment in the heart of vibrant downtown! This sun-filled + spacious 1-bed, 1-bath condo at popular Fountain Terrace offers an open flow of entertainment spaces, featuring an accommodating living/dining area with luxury vinyl flooring

  

  Melanie Healey

  Coldwell Banker Realty

  71 Strawberry Hill Ave Unit 1015, Stamford, CT 06902
• 

  

  /64

  Starting at $2,400 Plus Fees

  • 1 - 2 Beds

  66 Glenbrook Rd, Stamford, CT 06902

  Located in downtown Stamford, minutes from I-95, the Merritt Parkway and Metro North Railroad Station, The Parc at Glenbrook offers a variety of furnished and unfurnished 1 and 2 bedroom apartments featuring fully equipped kitchens, washer/dryers, fireplaces, spacious closets, balconies and more. The state of the art fitness center, sparkling outdoor swimming pool and four private parking

  The Parc at Glenbrook

  

  66 Glenbrook Rd, Stamford, CT 06902
• 

  $1,925,000

  Sold Aug 12, 2025

  16 Dubois St, Darien, CT 06820

  • 4 Beds
  • 2.5 Baths
  • 2,337 Sq Ft
  • Built 1940

  Last Sold Summary

  • 7% Above List Price
  • $824/SF
  • 7 Days On Market

  Current Estimated Value $2,141,648

  Last Listing Agent Cheryl Williams Brown Harris Stevens

  16 Dubois St, Darien, CT 06820
• 

  Not Listed For Sale

  29 Maplewood Dr, Cos Cob, CT 06807

  • 7 Beds
  • 5.5 Baths
  • 4,258 Sq Ft
  • Built 1960

  29 Maplewood Dr, Cos Cob, CT 06807

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Angela Alfano Coldwell Banker Realty
• 

  

  /28

  $640,000

  Open Sun 12PM - 2PM

  • 2 Beds
  • 2.5 Baths
  • 2,032 Sq Ft

  2435 Bedford St Unit 10C, Stamford, CT 06905

  Welcome home to the prestigious, gated Chesterfield community, where classic townhouse charm meets modern convenience in central Stamford! This beautifully maintained residence features a spacious multi-level layout designed for both quiet relaxation and effortless entertaining. Upstairs, dual en-suite bedrooms each feature their own dedicated full bath, offering exceptional privacy for guests as

  

  Toni Mickiewicz

  William Pitt Sotheby's Int'l

  2435 Bedford St Unit 10C, Stamford, CT 06905
• 

  

  /20

  $3,245 Per Month

  • 2 Beds
  • 2 Baths
  • 1,272 Sq Ft
  • Townhouse for Rent

  41 Fairfield Ave, Stamford, CT 06902

  Located on the brim of vibrant downtown Stamford and in the heart of the popular Fairgate community, this newer townhome is super spacious + accommodating, offering 1275 square feet! Inside you'll find a designer kitchen with cool new granite countertops, opening to the bright + sunny window-lined living + dining areas featuring extra windows + fresh paint. This townhome has it's own entrance on

  

  Melanie Healey

  Coldwell Banker Realty

  41 Fairfield Ave, Stamford, CT 06902
• 

  $890,000

  Sold Oct 30, 2025

  11 Bel Aire Dr, Stamford, CT 06905

  • 3 Beds
  • 2.5 Baths
  • 2,463 Sq Ft
  • Built 1957

  Last Sold Summary

  • 5% Above List Price
  • $361/SF
  • 11 Days On Market

  Current Estimated Value $924,240

  Last Listing Agent Edward Zislis Higgins Group Real Estate

  11 Bel Aire Dr, Stamford, CT 06905
• 

  

  /21

  Not Listed For Sale

  50 Almira Dr Unit B, Greenwich, CT 06831

  • 2 Beds
  • 2.5 Baths
  • 1,798 Sq Ft
  • Built 2002

  50 Almira Dr Unit B, Greenwich, CT 06831

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Liz Eckert William Raveis Real Estate
• 

  

  /36

  $389,900

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,240 Sq Ft

  154 Cold Spring Rd Unit 86, Stamford, CT 06905

  Experience convenient one-level living in this spacious 2-bedroom, 1.5-bath home at Candlelight Terrace. This newly updated unit is move-in ready. The layout offers generous living and dining areas, ample closet space, and abundant natural light throughout. Step out onto your private patio to enjoy peaceful water views and the soothing sound of the nearby Rippowam River-a tranquil setting perfect

  

  Rudy Pierre

  YellowBrick Real Estate LLC

  154 Cold Spring Rd Unit 86, Stamford, CT 06905
• 

  

  /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
• 

  

  /61

  $3,195,500

  Sold Aug 06, 2026

  14 Upland Dr, Greenwich, CT 06831

  • 4 Beds
  • 4.5 Baths
  • 4,113 Sq Ft
  • Built 1936

  Last Sold Summary

  • $777/SF
  • 18 Days On Market

  Current Estimated Value $3,284,985

  Last Listing Agent Roseann Benedict Compass Connecticut, LLC

  14 Upland Dr, Greenwich, CT 06831
• 

  

  /19

  Not Listed For Sale

  54 Greenwich Hills Dr, Greenwich, CT 06831

  • 3 Beds
  • 3.5 Baths
  • 2,176 Sq Ft
  • Built 1976

  54 Greenwich Hills Dr, Greenwich, CT 06831

  Last Sold Summary

  • 177 Days On Market

  Last Listing Agent Janie Galbreath Coldwell Banker Realty
• 

  

  /21

  $395,000

  $35K PRICE DROP Pending

  • 2 Beds
  • 1.5 Baths
  • 1,240 Sq Ft

  154 Cold Spring Rd Unit 62, Stamford, CT 06905

  Beautifully updated 2-bedroom, 1.5-bath residence offering a bright, functional layout and true move-in ready living. This well-maintained unit features brand new flooring throughout, updated finishes, and thoughtful improvements that enhance both style and comfort. Enjoy a private deck, a fully upgraded laundry area with new washer & dryer and dedicated water shut-off, and access to a

  

  Spencer Sodokoff

  Houlihan Lawrence

  154 Cold Spring Rd Unit 62, Stamford, CT 06905
• 

  

  /14

  $2,900 Per Month

  • 2 Beds
  • 1 Bath
  • 818 Sq Ft
  • House for Rent

  60 Strawberry Hill Ave Unit 814, Stamford, CT 06902

  Stamford 818SF condo Available September 1, 2026 with two bedrooms asking $2,900.00. per month which includes heat, hot water, electricity. Conveniently located just minutes from downtown Stamford, on the eighth floor with good views of Stamford. This location places you within easy access to all downtown Stamford has to offer including wonderful restaurants, houses of worship, shopping, library,

  

  John Zervos

  DVB Commercial Realty LLC

  60 Strawberry Hill Ave Unit 814, Stamford, CT 06902
• 

  

  /31

  $1,575,000

  Sold Mar 12, 2026

  45 Sound Beach Avenue Extension, Greenwich, CT 06878

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1953

  Last Sold Summary

  • 1% Below List Price
  • $1,172/SF
  • 56 Days On Market

  Current Estimated Value $1,593,615

  Last Listing Agent Susan Isaak Coldwell Banker Realty

  45 Sound Beach Avenue Extension, Greenwich, CT 06878
• 

  Est $4,100,111

  Not Listed For Sale

  16 Lighthouse Way, Darien, CT 06820

  • 5 Beds
  • 4.5 Baths
  • 3,977 Sq Ft
  • Built 1966

  16 Lighthouse Way, Darien, CT 06820

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Becky Munro Brown Harris Stevens

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