Old Greenwich, CT Homes

• 

  

  

  /38

  $999,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,948 Sq Ft

  65 Macarthur Ln Unit 6, Stamford, CT 06902

  Tucked away on a meticulously kept cul-de-sac, this spacious and refined Colonial offers the perfect combination of comfort, elegance, and convenience. Situated in one of Stamford's most sought-after, commuter-friendly neighborhoods, the home showcases an airy, open-concept layout designed for modern living and a new roof! At the heart of the home, a sun-drenched kitchen features gleaming quartz

  

  Adam Wagner

  Keller Williams Prestige Prop.

  (475) 275-6955

  65 Macarthur Ln Unit 6, Stamford, CT 06902
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• 

  

  

  /17

  $1,950 per month

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

  50 Courtland Ave Unit A4, Stamford, CT 06902

  Updated 1 Bedroom/ 1 Bath Condo in Stamford. Updated Sun-Splashed Kitchen Offers an Abundance of Cabinetry Built-in Pantry Closet, Tile Floor, Granite Counter-tops, Stainless Steel Appliances. Bright Unit w/ Recessed Lighting, Clean Carpet, Newer Windows, Freshly Painted w/ Crown Moldings. Updated bathroom w/ Tiled Shower, Granite top Vanity. Reserved Parking Right Outside of the Unit. Great

  

  Federico Martinez

  Keller Williams Prestige Prop.

  (203) 635-5218

  50 Courtland Ave Unit A4, Stamford, CT 06902
• 

  $425,000 Sold Jun 27, 2025

  • 1,193 Sq Ft
  • $356/SF
  • 19 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1976

  61 Riverside Ave Unit 15, Stamford, CT 06905

  Welcome to River House.... Move right into this spacious end unit, Features 2 Bedroom, 2 Full Baths, in-ground pool & clubhouse. Large Living Room and Dining Room lead to balcony overlooking the pool and the Rippowam River. Freshly painted, new carpeting. Quiet mid-city location. Walk to Scalzt Park, golf courses, tennis courts, transportation, shopping, restaurants, and Mill River!

  Glenn Marr Marr Caruso Realty Group

  61 Riverside Ave Unit 15, Stamford, CT 06905
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft

  305 Sylvan Knoll Rd, Stamford, CT 06902

  305 Sylvan Knoll Rd, Stamford, CT 06902
• 

  

  

  /36

  $359,000

  • 1 Bed
  • 1 Bath
  • 640 Sq Ft

  1 Strawberry Hill Ct Unit PH, Stamford, CT 06902

  Sky-High Living with Unmatched Views - 1 Bedroom/1 Bath Penthouse at Strawberry Hill Court. Welcome to your private retreat in the sky! Perched atop the coveted Strawberry Hill address, this one-of-a-kind rooftop penthouse offers breathtaking 360 panoramic views-from the glittering skyline of Manhattan to sweeping vistas of Long Island Sound and the vibrant cityscape of Stamford below. This

  Mara Tome

  Keller Williams Prestige Prop.

  (914) 998-5307

  1 Strawberry Hill Ct Unit PH, Stamford, CT 06902
• 

  

  /26

  $6,000 per month

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

  49 Hollow Tree Ridge Rd, Darien, CT 06820

  A rare, unique "Nathaniel B. Weed" historic Antique Federal Colonial home in Darien, CT updated with modern conveniences being offered TURNKEY and tastefully FURNISHED - just bring your suitcase and enjoy! 3 BR, 2 BA townhouse- style unit where all three levels are loaded with charm and character. Features include a Mansard roof, wide plank flooring, hand hewn beams, multiple fireplaces, newer

  

  Karen Finn

  Gatehouse Realty Inc

  (203) 693-9554

  49 Hollow Tree Ridge Rd, Darien, CT 06820
• 

  $650,000 Sold Jun 27, 2025

  • 1,864 Sq Ft
  • $349/SF
  • 15 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1951

  29 Old Barn Rd S, Stamford, CT 06905

  Welcome to this fantastic 4-bedroom, 2-bathroom home nestled at the end of a peaceful cul-de-sac on a spacious corner lot in Stamford. Bring your design vision and make this charming house your dream home! Inside, you'll find an open-floor plan featuring a large living room and kitchen, perfect for both entertaining and everyday living. The main level also offers a cozy family room, and two

  Noelle Iannotta Compass Connecticut, LLC

  29 Old Barn Rd S, Stamford, CT 06905
• 

  

  /32

  Not Listed For Sale

  • 6 Beds
  • 6 Baths
  • 4,645 Sq Ft

  550 River Rd, Greenwich, CT 06807

  550 River Rd, Greenwich, CT 06807
• 

  

  /35

  $560,000

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

  101 Grove St Unit 19, Stamford, CT 06901

  Enjoy the best of both worlds: a prime downtown location with rare privacy and tranquility. Tucked away from the main road and overlooking a lush, serene courtyard, this home feels worlds away, yet downtown's energy is just steps from your door. This meticulously maintained 2-bedroom, 2.5-bath townhouse blends modern comfort with unbeatable convenience in the heart of Downtown Stamford. The entry

  

  Christopher Reid

  Keller Williams Realty

  (203) 884-0974

  101 Grove St Unit 19, Stamford, CT 06901
• 

  

  /16

  $4,700 per month

  • 3 Beds
  • 2 Baths
  • Apartment for Rent

  19 Valley Rd Unit A, Cos Cob, CT 06807

  Easy living in central Cos Cob. Gracious 3 bedroom 2bathroom townhouse. Hardwood floors and air-conditioning. Jus a few minutes walk to coffee and pastry or 14 minute walk to the train. Large beautiful deck, covered front porch and small garden . Off and on street parking. Gas heating and cooking. Only a couple blocks to school, playground and park.

  

  Scott Kadison

  Scott Kadison Real Estate

  (203) 872-6830

  19 Valley Rd Unit A, Cos Cob, CT 06807
• 

  $535,000 Sold Jun 27, 2025

  • 1,487 Sq Ft
  • $360/SF
  • 23 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1977

  202 Soundview Ave Unit 26, Stamford, CT 06902

  Welcome to Bishop Meadows, a small residential enclave nestled in a wooded location directly across from Cummings Beach Park. This lovely 2 BR, 2.5 BTH tri-level townhome is freshly painted and features an eat-in kitchen, large living room with fireplace, deck and a large separate dining space and powder room on the main level. Kitchen equipped with brand new refrigerator, range, hood vent,

  Connie Kim Coldwell Banker Realty

  202 Soundview Ave Unit 26, Stamford, CT 06902
• 

  

  /27

  Est $1,682,000 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 4,793 Sq Ft

  35 Walnut Ridge Ct, Stamford, CT 06905

  35 Walnut Ridge Ct, Stamford, CT 06905
• 

  

  /40

  $1,800,000

  • 6 Beds
  • 5 Baths
  • 3,461 Sq Ft

  47 Hollow Tree Ridge Rd, Darien, CT 06820

  A Rare Darien Gem and opportunity to own this historic Federal Colonial 2-family home, one of Darien's few multi-family properties. Spanning over 3,460 SF on .47 acres, this turn-key furnished residence blends timeless elegance with modern versatility, ideal for investors, families, multi-generational households, or young couples seeking rental income. Historic Charm, Modern Comfort: * Two

  

  Karen Finn

  Gatehouse Realty Inc

  (475) 325-5924

  47 Hollow Tree Ridge Rd, Darien, CT 06820
• 

  

  /27

  $6,750 per month

  • 5 Beds
  • 3.5 Baths
  • 4,776 Sq Ft
  • House for Rent

  208 Guinea Rd, Stamford, CT 06903

  Pristine and spacious 5-bedroom Colonial for rent near the Greenwich border, perfect for both everyday living and elegant entertaining. Recently renovated throughout with fresh interior/exterior paint, brand new bathrooms, updated flooring, kitchen improvements, and electrical upgrades. The classic center hall layout includes a formal dining room, living room with fireplace, and a large eat-in

  

  Laura Danforth

  William Raveis Real Estate

  (203) 801-8001

  208 Guinea Rd, Stamford, CT 06903
• 

  $2,801,000 Sold Jun 27, 2025

  • 3,638 Sq Ft
  • $770/SF
  • 9 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2002

  24 Casement St, Darien, CT 06820

  Nestled in a close-knit neighborhood with front yard playdates and backyard barbecues, this 5 bedroom classic colonial, set on a flat .5 acre lot, is a perfect blend of tradition and modern comfort. Located just moments from Noroton Heights Train Station, the vibrant energy of Darien Commons, shopping, restaurants and local beaches, this home offers a rare combination of convenience and serene

  Genevieve Schettino Compass Connecticut, LLC

  24 Casement St, Darien, CT 06820
• 

  Est $697,284 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,045 Sq Ft

  20 3rd St Unit 14, Stamford, CT 06905

  20 3rd St Unit 14, Stamford, CT 06905
• 

  

  /36

  $5,495,000

  • 6 Beds
  • 8 Baths
  • 7,930 Sq Ft

  20 Sherwood Farm Ln, Greenwich, CT 06831

  Step into luxury with this newly staged custom built home in one of Greenwich's prestigious associations. Perfectly situated near downtown, this elegant property offers a blend of sophistication and convenience- now at an improved price! A stunning custom built white Georgian Colonial in the coveted mid country Sherwood Farm Association is sited on a picturesque level acre lot. This six bedroom

  

  Richard Higgins

  Higgins Group Bedford Square

  (203) 433-0559

  20 Sherwood Farm Ln, Greenwich, CT 06831
• 

  

  /13

  $4,895 per month

  • 3 Beds
  • 1.5 Baths
  • 1,776 Sq Ft
  • House for Rent

  359 West Ave, Darien, CT 06820

  Commuters delight. Walk to train updated home with many newer improvements. The freshly painted interior is complemented by newer kitchen appliances w/large eat-in area, a renovated half bath, formal dining rm w/built-in hutch & living room with brick fireplace. Upstairs you'll find 3 beds & a large full bath w/laundry. An inviting glass enclosed 3 season front porch, plenty of basement & attic

  

  Robert Marchesi

  Compass Connecticut, LLC

  (203) 439-5295

  359 West Ave, Darien, CT 06820
• 

  

  /23

  $714,000 Sold Jun 27, 2025

  • 71 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1950

  100 Putnam Park, Greenwich, CT 06830

  Large 2BR/2Bth end unit in Putnam Park located in the heart of downtown Greenwich. Designer touches throughout with fully renovated primary bath, refinished hardwood floors, formal dining room with built-ins. Set in rear of complex with 3 exposures providing lots of sunlight and quiet relaxation. The pulldown attic allows for ample storage. All NEW WINDOWS to be installed. This lovely unit

  Renee Haggquist Sotheby's International Realty

  100 Putnam Park, Greenwich, CT 06830
• 

  Est $691,189 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,785 Sq Ft

  20 3rd St Unit 13, Stamford, CT 06905

  20 3rd St Unit 13, Stamford, CT 06905
• 

  

  /30

  $3,700,000 Under Contract

  • 5 Beds
  • 5 Baths
  • 5,200 Sq Ft

  164 Clapboard Ridge Rd, Greenwich, CT 06831

  Classic colonial in a coveted location minutes from town and schools. A gracious double height foyer leads to generously proportioned entertaining rooms including a large living room, oversized dining room, and spacious country kitchen with adjacent family room. A beautifully paneled library, main level primary suite and office complete this floor. Upstairs are 4 additional bedrooms and 3

  

  Carol Clarke Gilbride

  Sotheby's International Realty

  (475) 284-7134

  164 Clapboard Ridge Rd, Greenwich, CT 06831
• 

  

  /15

  $4,690 per month

  • 3 Beds
  • 1.5 Baths
  • 2,515 Sq Ft
  • House for Rent

  22 Glen Terrace, Stamford, CT 06906

  Sunny and Spacious Classic 3 Bedroom 1.5 Bath Colonial in Quiet Glenbrook Neighborhood, on the border with Darien, on a leafy one way street. Large Kitchen with Cooktop, Oven, Dishwasher & Refrigerator. Separate Dining Room. Hardwood Floors Thru-Out. Living Room with Wood Burning Fireplace. Large Sun Drenched Enclosed Rear Porch overlooking the garden and water stream at the backyard. Huge walk

  

  Urs Klarer

  Coldwell Banker Realty

  (203) 587-8611

  22 Glen Terrace, Stamford, CT 06906
• 

  $1,100,000 Sold Jun 27, 2025

  • 3,690 Sq Ft
  • $298/SF
  • 16 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1941

  36 Meadowpark Ave E, Stamford, CT 06905

  HIGHEST AND BEST OFFERS BY WEDS. 4/23 @ 5:00PM Welcome to 36 Meadowpark Avenue East, an exquisitely expanded and completely redone residence, offering the perfect blend of elegance and modern convenience. This centrally located Stamford gem provides easy access to shopping, dining, the parkway, and the train, ensuring a lifestyle of comfort and accessibility. Step inside to discover an

  Hyleri Katzenberg Compass Connecticut, LLC

  36 Meadowpark Ave E, Stamford, CT 06905
• 

  Est $662,382 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,810 Sq Ft

  20 3rd St Unit 11, Stamford, CT 06905

  20 3rd St Unit 11, Stamford, CT 06905
• 

  

  /21

  $500,000

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  39 Hearthstone Ct, Stamford, CT 06902

  Rare opportunity to own a classic ranch in The Cove, one of Stamford's more sought-after neighborhoods. Lovingly maintained by the same family for 70+ years, this 3-bedroom, 1-bath home is ideally located on a quiet cul-de-sac just minutes from Cove Island Park, the beach, and all the conveniences of downtown. Set on a generous 1/4-acre level lot, this charming home offers an open layout with a

  

  Len Schwartz

  Keller Williams Prestige Prop.

  (203) 872-9604

  39 Hearthstone Ct, Stamford, CT 06902
• 

  

  /12

  $2,300 per month

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

  20 Daly St Unit 2F, Stamford, CT 06902

  Just walk in and enjoy! Sun-filled condo walking distance to train station and Downtown Stamford. Newer kitchen, stainless steel appliances and breakfast bar. Hardwood floors throughout, W/D in unit, reserved parking and private storage unit. Close to I95, Beach, Parks and Restaurants. Fully furnished comes with 3 TVs, with a bar and fancy disco lights & music system, fitness bike. Available also

  

  Urs Klarer

  Coldwell Banker Realty

  (203) 666-4556

  20 Daly St Unit 2F, Stamford, CT 06902
• 

  $245,000 Sold Jun 26, 2025

  • 670 Sq Ft
  • $366/SF
  • 48 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1947

  1858 Summer St Unit 1858, Stamford, CT 06905

  Newly Updated Bright 1 BR Unit in a charming well-maintained complex. Newly remodeled kitchen. New cabinetry. New floors throughout. Newly remodeled bathroom. Freshly painted. Lots of closet space. Private Locked Storage Unit. Conveniently located mid-city but quietly tucked away. Reserved parking space directly in front. Coin-Op Laundry is clean, locked and on premises. Common charge includes

  Anthony Martino William Pitt Sotheby's Int'l

  1858 Summer St Unit 1858, Stamford, CT 06905
• 

  Est $806,607 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  77 Havemeyer Ln Unit 314, Stamford, CT 06902

  77 Havemeyer Ln Unit 314, Stamford, CT 06902
• 

  

  /22

  $495,000

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  87 Charles St, Stamford, CT 06902

  Opportunity awaits with this charming 3 bedroom home nestled in a desirable Stamford neighborhood, just a short walk to the water! While the interior is in need of updates, the home offers a solid layout with great potential for renovation or expansion. Perfect for buyers looking to customize and add their personal touch. Enjoy a leveled backyard that is nicely maintained. Located in a quiet,

  

  Adam Wagner

  Keller Williams Prestige Prop.

  (475) 348-7239

  87 Charles St, Stamford, CT 06902
• 

  

  /17

  $1,600 per month

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

  18 Quintard Terrace Unit 1F, Stamford, CT 06902

  FOR AGES 55+ Affordable Apartment! Immaculate, Bright and Sunny! Please see income/eligibility requirements to see if you qualify. MONTHLY RENT INCLUDES ALL UTILITIES AND PARKING! Electric, gas, water and hot water are included in the monthly rent! Conveniently located close to downtown Stamford, I-95 and Cove Island Beach, this pretty apartment features: A cheerful, open kitchen, living-dining

  

  Melanie Healey

  Coldwell Banker Realty

  (475) 290-6976

  18 Quintard Terrace Unit 1F, Stamford, CT 06902
• 

  

  /10

  $5,000,000 Sold Jun 26, 2025

  • 5,417 Sq Ft
  • $923/SF
  • 13 Days On Market

  • 6 Beds
  • 6 Baths
  • Built 1958

  95 Indian Head Rd, Riverside, CT 06878

  Nestled in a desired Riverside location, this home elegantly blends sophistication and modern convenience. Renovated in 2024, this beauty sits on 1.38 acres and is just minutes to town. It features a gourmet kitchen, illuminated by natural light, accompanied by a large breakfast area. Both the family room and the formal dining room feature their own fireplaces, enhancing comfort and ambiance. A

  Kristen Studwell Compass Connecticut, LLC

  95 Indian Head Rd, Riverside, CT 06878
• 

  Not Listed For Sale

  • Studio
  • 1 Bath
  • 425 Sq Ft

  54 W North St, Stamford, CT 06902

  54 W North St, Stamford, CT 06902
• 

  

  /17

  $375,000

  • 3 Beds
  • 1 Bath
  • 1,170 Sq Ft

  37 Greenwich Ave Unit 1-2, Stamford, CT 06902

  Great commuter location to own this 3Br 1Bath Condo in the heart of Stamford. The Condo has a spacious living room, remodeled kitchen with granite countertops and stainless appliances. The condo comes with 2 parking spaces - one in the garage and one in front of the unit. Short walk to Stamford train station, to down town Stamford, restaurants, shopping and a short drive to I-95.

  

  Hy Natarajan

  Keller Williams Prestige Prop.

  (203) 479-9224

  37 Greenwich Ave Unit 1-2, Stamford, CT 06902
• 

  

  /22

  $7,495 per month

  • 3 Beds
  • 2.5 Baths
  • 2,326 Sq Ft
  • House for Rent

  27 Hollow Tree Ridge Rd, Darien, CT 06820

  As good as it gets FURNISHED rental property. One year lease term preferred. Stylishly updated and furnished, this charming colonial has 3 bedrooms and 2.1 baths and everything else a renter could possibly want. The main floor is configured with a formal dining room and spacious living room with fireplace. The recently renovated eat-in kitchen has stainless steel appliances and a cozy breakfast

  

  Robert Marchesi

  Compass Connecticut, LLC

  (475) 215-2593

  27 Hollow Tree Ridge Rd, Darien, CT 06820
• 

  $280,000 Sold Jun 26, 2025

  • 980 Sq Ft
  • $286/SF
  • 15 Days On Market

  • 1 Bath
  • Built 1988

  1 Landmark Square Unit 607, Port Chester, NY 10573

  Bring your tools!! Capture this rare opportunity, in the Landmark building in the heart of Port Chester. This enormous studio (and I mean big) features over 1200 square feet including the expansive outdoor PRIVATE patio. This condo can be perfect for any home owner with an imagination. It is just a shell of what it once was and is just waiting for someone to bring back the sparkle. This unit

  Kimberly Cacace Howard Hanna Rand Realty

  1 Landmark Square Unit 607, Port Chester, NY 10573
• 

  Est $373,922 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft

  1 Landmark Square Unit 621, Port Chester, NY 10573

  1 Landmark Square Unit 621, Port Chester, NY 10573
• 

  

  /40

  $2,800,000

  • 3 Beds
  • 3.5 Baths
  • 3,251 Sq Ft

  523 E Putnam Ave Unit B, Greenwich, CT 06830

  Space and convenience await you at this incredible townhouse with views of the Mianus River and a location close to Old Greenwich, Riverside and Cos Cob. This 3 bedroom, 3.5 bath home has high ceilings throughout, generously sized rooms and picture-perfect outdoor space. With 3 dedicated underground parking spaces and an elevator to take you to your living floor, this is as easy as it gets. The

  

  Allen Vetrosky

  Berkshire Hathaway NE Prop.

  (203) 654-3755

  523 E Putnam Ave Unit B, Greenwich, CT 06830
• 

  

  /21

  $2,895 per month

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

  39 Hazel St, Stamford, CT 06902

  Rare opportunity to rent a 2-bed/2 bath townhome at desirable Fairgate! Located on the brim of vibrant downtown Stamford, this bright + newer townhome is move-in ready with large sunny rooms, designer kitchen with granite countertops, new carpeting + fresh paint. Beautifully set along the sidewalked streets + mature trees of Fairgate, residents enjoy a meticulously maintained, pet-friendly

  

  Melanie Healey

  Coldwell Banker Realty

  (475) 255-7288

  39 Hazel St, Stamford, CT 06902
• 

  $325,000 Sold Jun 26, 2025

  • 875 Sq Ft
  • $371/SF
  • 71 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1959

  Unlisted Address

  Great investment opportunity in desirable gated Community, centrally located, 2 bedrooms unit beautifully renovated, Brazilian Cherry hardwood floors thru-out, granite counter top,Stainless Steel appliances, new electrical fixtures and more. From the balcony enjoy the lovely view of the fountain, and, on hot days, relax by the pool, on site. Heat/ hot water is included, assigned parking space.

  Rose Revel William Raveis Real Estate

  Unlisted Address
• 

  Est $305,585 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 752 Sq Ft

  1 Landmark Square Unit 225, Port Chester, NY 10573

  1 Landmark Square Unit 225, Port Chester, NY 10573

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