86

Colonial Homes for Sale in Old Greenwich, CT

Section Image
  • /39

    $4,425,000

    • 4 Beds
    • 6 Baths
    • 5,038 Sq Ft

    108 Perkins Rd, Greenwich, CT 06830

    Welcome home to 108 Perkins Road. Set on over 2 private, beautifully landscaped acres in Midcountry, this classic Colonial offers the perfect blend of timeless elegance, exceptional outdoor living, and everyday convenience. Spacious and inviting interiors feature generous formal/ informal living spaces, 4 bedrooms, 6 bathrooms, and a finished lower level providing valuable additional living and

    Kristen Forlini Compass Connecticut, LLC

    108 Perkins Rd, Greenwich, CT 06830
  • /32

    $4,000,000

    • 4 Beds
    • 2.5 Baths
    • 2,014 Sq Ft

    14 Shoreham Club Rd, Old Greenwich, CT 06870

    A rare Shorehame Association lot with unobstructed Long Island Sound sight lines offered as an amazing opportunity to build new or reimagine the existing residence in one of Old Greenwich's most sought after waterfront settings. The .28 acre property sits within a private association that includes sandy beach access, a boat launch ramp for paddle boarding, kayaking and boating and a large

    Catherine Aaron Berkshire Hathaway NE Prop.

    14 Shoreham Club Rd, Old Greenwich, CT 06870
  • /40

    $849,999

    • 5 Beds
    • 3.5 Baths
    • 2,846 Sq Ft

    44 Toms Rd, Stamford, CT 06906

    Welcome to 44 Toms Road, a rare opportunity to own a home that seamlessly blends generous living space, exceptional versatility, and an unbeatable Stamford location. Offering 5 bedrooms, 3 bathrooms & 1 half bath, and a thoughtfully designed floor plan, this home is built for both comfortable everyday living and effortless entertaining. Bright, inviting living spaces flow seamlessly into a

    Jorge Lopez Coldwell Banker Realty

    44 Toms Rd, Stamford, CT 06906
  • /40

    $2,300,000

    • 7 Beds
    • 5.5 Baths
    • 6,103 Sq Ft

    64 Sanford Ln, Stamford, CT 06905

    64 Sanford Lane, a combination of design and functionality was meticulously renovated in late 2024, offering 6,103 sq ft of functional space. Situated on a quiet, tree-lined street, it offers 7 bedrooms & 5.5 bathrooms on a flat, corner lot in the popular neighborhood of Pepper Ridge, known as Case Acre Estates. The main level is an open flow built for everyday living and large-scale

    Lisa Linzer L & S Realty

    64 Sanford Ln, Stamford, CT 06905
  • /39

    $13,500,000

    • 4 Beds
    • 7 Baths
    • 7,142 Sq Ft

    16 Indian Point Ln, Riverside, CT 06878

    Presenting a rare Riverside home, this SBP Homes masterpiece, custom-built in 2009, is now on the market for the first time. Designed to capture breathtaking water views and stunning sunsets. Situated in a peaceful private association within the desirable 1-acre zone off Indian Head Road. Manhattan skyline in the distance, regular Summer firework displays can be seen from Rye Playland as the

    Robert Johnson Brown Harris Stevens CT, LLC

    16 Indian Point Ln, Riverside, CT 06878
  • /50

    $5,995,000

    • 4 Beds
    • 4.5 Baths
    • 3,827 Sq Ft

    25 Cove Rd, Old Greenwich, CT 06870

    Experience unparalleled luxury in this brand-new, just-completed masterpiece by Braydan Construction. Located in the exclusive Lucas Point association, this stunning 4-bedroom, 4.5-bath home offers coveted access to a neighborhood beach and private pier. Defined by a ''coastal chic'' aesthetic, natural light pours through the home, highlighting exquisite hand-sewn oak beams, top-of-the-line

    Alison Farn-Leigh Brown Harris Stevens CT, LLC

    25 Cove Rd, Old Greenwich, CT 06870
  • /40

    $4,749,000

    $201K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 2,949 Sq Ft

    212 Milbank Ave Unit South, Greenwich, CT 06830

    Stunning brick-clad Georgian Townhome boasts a private, enchanting courtyard terrace with fountain and fireplace ideally located on the corner of Milbank, just two blocks from Greenwich Avenue. This elegant home showcases a grandly scaled, sunwashed interior with soaring ceiling heights and striking architectural details including French door terrace access, ideal for indoor/outdoor entertaining.

    Deborah Needle Houlihan Lawrence

    212 Milbank Ave Unit South, Greenwich, CT 06830
  • /40

    $3,150,000

    • 4 Beds
    • 3.5 Baths
    • 4,397 Sq Ft

    4 Mercia Ln, Greenwich, CT 06830

    Belle Haven Peninsula-one of Greenwich's most coveted coastal enclaves, where harbor breezes, in-town convenience, and quiet residential character come together in a way few addresses can offer. Privately sited on a tranquil cul-de-sac and close to downtown, this 4-BR, 3.5-BA residence is approx. 4,300 sq ft of graciously scaled living space. Built in 1995 and impeccably maintained, the home

    Evangela Brock Douglas Elliman of Connecticut

    4 Mercia Ln, Greenwich, CT 06830
  • /27

    $1,495,000

    • 3 Beds
    • 2.5 Baths
    • 1,804 Sq Ft

    3 Westminster Rd, Stamford, CT 06902

    Shippan Waterfront Community! Pristine home with water views just a short walk to the beach! Updated 3-BR, 2.5 bath home on quiet cul de sac. Large eat in kitchen, living room with vaulted ceiling and fireplace. Family room and half bath complete the first floor. Hardwood floors throughout. Upper level has primary BR with full bath plus two additional bedrooms and full hall bath. Many recent

    Suzanne Cingari William Pitt Sotheby's Int'l

    3 Westminster Rd, Stamford, CT 06902
  • /30

    $4,100,000

    • 4 Beds
    • 2 Baths
    • 1,904 Sq Ft

    Unlisted Address

    Development opportunity. This 0.735 acre property is currently improved with 1,904 sq. Ft. two story traditional single-family house. The current zoning is R-20 which was up zoned circa 2000 from two R-12 building lots. Assuming the current structure is razed the current FAR of 0.225 allowing for a total of 7,203 sq. ft. on two floors plus a 1,440 sq. ft. third story for a total of 8,643 sq. t.

    Liz Eckert William Raveis Real Estate

    Unlisted Address
  • /32

    $4,495,000

    • 5 Beds
    • 5.5 Baths
    • 4,259 Sq Ft

    16 Ridgebrook Rd, Greenwich, CT 06830

    Just minutes from downtown Greenwich, this beautifully renovated Colonial offers the ideal blend of luxury, comfort, and convenience. The bright, open interior features soaring ceilings, hardwood floors, a custom kitchen with stone countertops and stainless steel appliances, and an impressive great room with fireplace overlooking the backyard. Designed for today's lifestyle, all bedrooms feature

    Jose Cuartas Corcoran Centric Realty LLC

    16 Ridgebrook Rd, Greenwich, CT 06830
  • /30

    $1,600,000

    • 4 Beds
    • 2 Baths
    • 2,350 Sq Ft

    105 Rose Ln, Darien, CT 06820

    105 Rose Lane blends classic charm with modern updates in a welcoming Darien neighborhood. This sun-filled 4-bedroom, 2-bath home features an open-concept first floor, an updated kitchen, and beautifully renovated bathrooms for a move-in ready experience. An additional living space offers flexibility for relaxing or entertaining, while the fantastic front porch is perfect for enjoying morning

    Genevieve Schettino Compass Connecticut, LLC

    105 Rose Ln, Darien, CT 06820
  • /53

    $2,500,000

    • 4 Beds
    • 4 Baths
    • 4,851 Sq Ft

    3 Carriage Rd, Cos Cob, CT 06807

    Nestled on a peaceful cul-de-sac in a desirable Cos Cob neighborhood, this beautifully crafted 2003 traditional offers approximately 4,800 sq. ft. on 1.25 private acres. Thoughtfully designed for comfortable living and entertaining, the home is being offered for the first time since being built and features four spacious bedrooms, five full baths, and three fireplaces that add warmth and

    Stephen Archino Sotheby's International Realty

    3 Carriage Rd, Cos Cob, CT 06807
  • /36

    $1,849,000

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 4,278 Sq Ft

    6 Walnut Ridge Ct, Stamford, CT 06905

    Exceptional NEW construction in a coveted mid-city location offers the perfect blend of refined comfortable living. This sensational 5-bedroom, 4.5 bathroom home with well proportioned rooms throughout, showcases sophisticated design together with an open-concept. The gourmet kitchen serves as the heart of the home, boasting a large center island, walk-in pantry, and abundant cabinet and counter

    Barbara Hickey William Pitt Sotheby's Int'l

    6 Walnut Ridge Ct, Stamford, CT 06905
  • /31

    $5,250,000

    • 5 Beds
    • 5.5 Baths
    • 6,997 Sq Ft

    16 Annjim Dr, Greenwich, CT 06830

    An exceptional opportunity to own a thoughtfully crafted 2015 Colonial in one of Greenwich's most desirable in-town neighborhoods. Set on level grounds at the end of a quiet cul-de-sac, this home offers four finished levels of natural light, high ceilings and refined finishes throughout. The heart of the home is an expansive kitchen with a large center island that flows effortlessly into the

    Amanda Bates Houlihan Lawrence

    16 Annjim Dr, Greenwich, CT 06830
  • /21

    $16,995,000

    $2M PRICE DROP
    • 5 Beds
    • 8.5 Baths
    • 8,248 Sq Ft

    207 Long Neck Point Rd, Darien, CT 06820

    This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering two separately deeded parcels ( that create this magical estate to ensure the peace and tranquility of your own private oasis. East facing views are enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned

    Shelly Tretter Lynch Compass Connecticut, LLC

    207 Long Neck Point Rd, Darien, CT 06820
  • /30

    $2,795,000

    • 4 Beds
    • 5 Baths
    • 2,828 Sq Ft

    93 Summit Rd, Riverside, CT 06878

    Classic four bedroom Colonial in a convenient Riverside location has been thoughtfully renovated and expanded over the years. Entertain in the spacious living room with fireplace and the sun-filled dining room leading to the open plan kitchen, breakfast area, and family room. Step out from both main rooms through French doors to the beautiful covered deck with fireplace and flagstone surround

    Julie Church Houlihan Lawrence

    93 Summit Rd, Riverside, CT 06878
  • /39

    $4,500,000

    • 3 Beds
    • 3.5 Baths
    • 4,259 Sq Ft

    248 Stanwich Rd, Greenwich, CT 06830

    Set on 1.21 acres, this beautifully maintained home has exceptional indoor and outdoor living designed for entertaining. Home was completely taken down to the studs in 2017. The freshly painted interior offers top-of-the-line finishes and a flexible floor plan. The main level features a private office with Murphy bed, dining room with soaring ceilings, and a cozy living room with wet bar and

    Julie Church Houlihan Lawrence

    248 Stanwich Rd, Greenwich, CT 06830
  • /45

    $4,250,000

    $545K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,890 Sq Ft

    40 W Elm St Unit 3D/E, Greenwich, CT 06830

    Experience true concierge living in one of Greenwich's premier full-service doorman buildings, ideally located just one block from Greenwich Avenue. Residences of this size, with park & Long Island Sound views, rarely become available in this building and are uncommon in the Greenwich condominium market, offering a unique opportunity for full-service, in-town living. This elegantly updated

    Joan Suter BHHS New England Properties

    40 W Elm St Unit 3D/E, Greenwich, CT 06830
  • /22

    $595,000

    • 1 Bed
    • 1 Bath
    • 582 Sq Ft

    25 W Elm St Unit 51, Greenwich, CT 06830

    GEM in Luxury Doorman BLDG in Town.Close to Train and all that Greenwich has to offer. Charming and well designed Pied-A-Terre, fireplace, high ceilings, privacy,extra storage in basement.Elegant apt with lovely mouldings, Waterworks tile,. Right off Gr AvePet permitted. Beautiful building.

    Lin Lavery Coldwell Banker Realty

    25 W Elm St Unit 51, Greenwich, CT 06830
  • /38

    $2,750,000

    • 4 Beds
    • 5 Baths
    • 2,814 Sq Ft

    316 Valley Rd, Cos Cob, CT 06807

    Some homes are built. This one was sculpted. Elevated above Mianus River,this turnkey home is where extraordinary grounds meet reimagined interior.Year round views, stone terraces, hidden garden paths, a grotto and lookout points create a private European escape in Cos Cob. A walkout entertainment room with wet bar and fireplace sets the tone. Elegant living and dining spaces with wine display

    Karin Fry Compass Connecticut, LLC

    316 Valley Rd, Cos Cob, CT 06807
  • /37

    $9,750,000

    • 6 Beds
    • 8 Baths
    • 11,567 Sq Ft

    31 Sawmill Ln, Greenwich, CT 06830

    Beautifully picturesque, a long, shared drive leads to the 1920 stone manor sitting high on park-like grounds bordered by 29 acres of wooded conservation land. Renovated and expanded, this warmly inviting residence offers 10,664± square feet with six bedrooms, six full and two half baths, plus eight fireplaces. Above the three-bay detached garage is a renovated two-bedroom, 903-square-foot

    Joseph Barbieri Sotheby's International Realty

    31 Sawmill Ln, Greenwich, CT 06830
  • /29

    $1,699,900

    $69K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,046 Sq Ft

    2435 Post Rd, Darien, CT 06820

    Spacious Colonial in the sought-after Hindley Elementary School district! Offering over 2500sf on the main and upper levels, this 5-bedroom, 3 full and 1 half bath home is designed for comfortable everyday living and entertaining. The oversized primary suite is complemented by generous living spaces, while 500sf finished lower level with wet bar provides an ideal recreation room, media room, home

    Fay Goebert William Raveis Real Estate

    2435 Post Rd, Darien, CT 06820
  • /28

    $1,499,000

    • 5 Beds
    • 3.5 Baths
    • 2,629 Sq Ft

    57 Revonah Ave, Stamford, CT 06905

    Timeless elegance meets modern luxury in this meticulously restored vintage Colonial, Ideally situated in the highly sought after Revonah neighborhood just a short walk to everything downtown Stamford has to offer. Rich in architectural character, this exceptional home showcases coffered 9' ceilings, classic wainscoting, custom millwork, built-ins, handsome hardwood floors, and gracious

    Tom Vozzella Berkshire Hathaway NE Prop.

    57 Revonah Ave, Stamford, CT 06905
  • /22

    $3,250,000

    • 7 Beds
    • 4.5 Baths
    • 3,439 Sq Ft

    33 Hillside Rd, Greenwich, CT 06830

    A unique opportunity awaits the new owner to put their own footprint on this lovely 1911 home. This house is beautifully sited on 2.27 acres in one acre zoning and cannot be subdivided. One can make a family compound here. High ceilings throughout, lovely sunroom which opens to the terrace and spacious yard with mature gardens. Magnificent alee of the most spectacular sycamore trees. Truly

    Elizabeth Douthit Brown Harris Stevens CT, LLC

    33 Hillside Rd, Greenwich, CT 06830
  • /19

    $675,000

    $14K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 3,024 Sq Ft

    707 Hope St, Stamford, CT 06907

    Beautifully-maintained single-family home offers the perfect blend of convenience, comfort, and opportunity. Ideally situated within walking distance of the Springdale Train Station. Thoughtfully updated for peace of mind, major improvements include a newer roof, central air conditioning, boiler, and efficient gas heating, ensuring year-round comfort and energy efficiency. Main-level washer and

    Eileen Carpanzano William Pitt Sotheby's Int'l

    707 Hope St, Stamford, CT 06907
  • /40

    $1,399,000

    • 6 Beds
    • 4.5 Baths
    • 3,568 Sq Ft

    80 3rd St, Stamford, CT 06905

    Discover the epitome of modern luxury living in this meticulously renovated 6 bedroom home nestled in the heart of Mid City, Stamford, CT. The perfect blend of timeless charm and contemporary flair, gleaming hardwood floors, abundant natural light, and elegant finishes adorn every corner, enhancing the ambiance of sophistication throughout. The gourmet kitchen is a chef's delight, featuring

    Jessica Buckley Keller Williams Prestige Prop.

    80 3rd St, Stamford, CT 06905
  • /35

    $995,500

    $155K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 3,179 Sq Ft

    387 Stillwater Ave, Stamford, CT 06902

    Thoughtfully designed for both comfortable everyday living and effortless entertaining, this spacious home offers an inviting layout and a backyard setting overlooking the E. Gaynor Brennan Golf Course. A dramatic two-story foyer greets you upon entry and leads to a formal living room and formal dining room. Adjacent to the dining room, the large kitchen features a center island, breakfast nook,

    Chris Carozza RE/MAX Right Choice

    387 Stillwater Ave, Stamford, CT 06902
  • /14

    $28,500,000

    • 7 Beds
    • 12 Baths
    • 18,370 Sq Ft

    39 Brookridge Dr, Greenwich, CT 06830

    Set along a quiet street 3 mins from town, this exceptional 2027 new construction blends timeless architecture with modern livability. A striking white brick façade, steep gables, and dark-framed windows create a refined yet welcoming presence. Warm interior light highlights expansive living spaces, including a dramatic kitchen and family room designed for both everyday living and elevated

    Amanda Bates Houlihan Lawrence Inc.

    39 Brookridge Dr, Greenwich, CT 06830
  • /60

    $7,450,000

    $500K PRICE DROP
    • 5 Beds
    • 9 Baths
    • 8,911 Sq Ft

    74 Rock Maple Rd, Greenwich, CT 06830

    Set on four beautifully landscaped acres in Greenwich, 74 Rock Maple Road is a classic Georgian-style residence that blends timeless architecture with exceptional modern amenities. Recently updated with a stunning new kitchen and beautifully renovated bathrooms, the home is designed for both elegant entertaining and comfortable everyday living. Gracious sun-filled interiors, a thoughtful floor

    Jenny Allen Compass Connecticut, LLC

    74 Rock Maple Rd, Greenwich, CT 06830
  • /40

    $8,795,000

    • 6 Beds
    • 10 Baths
    • 8,273 Sq Ft

    55 Calhoun Dr, Greenwich, CT 06831

    Majestic six bedroom manor, completely rebuilt with exceptional quality and craftsmanship, and sited on stunning 1.4 park-like acres in coveted Calhoun Drive Association. This distinguished residence is gracefully elevated to offer sweeping views of expansive lawns, lovely gardens and specimen trees. Impressive, sophisticated interiors throughout offer soaring ceilings, gleaming hardwood floors

    Barbara Wells Houlihan Lawrence

    55 Calhoun Dr, Greenwich, CT 06831
  • /37

    $3,100,000

    • 4 Beds
    • 4.5 Baths
    • 3,866 Sq Ft

    22 Ocean Dr N, Stamford, CT 06902

    Experience luxurious waterfront living in this stunning home in the coveted Shippan Point neighborhood, offering breathtaking water views, seamless indoor-outdoor entertaining spaces, & private access to the ALC association's private park, beach, & playground with an annual membership. The open-concept first floor features a gourmet kitchen with a gas Wolf Range, Sub-Zero refrigerator, breakfast

    Dannel Malloy NestSeekers International

    22 Ocean Dr N, Stamford, CT 06902
  • /32

    $729,900

    $69K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,917 Sq Ft

    80 Leonard St, Stamford, CT 06906

    Classic charm, endless potential, and a desirable Glenbrook location. This 3-bedroom, 2-bath Colonial offers nearly 2,000 SF on a level lot at the end of a quiet street. A welcoming front porch, mature landscaping, and detached 2-car garage create exceptional curb appeal. Inside, hardwood floors, abundant natural light, and timeless character complement a functional layout featuring a spacious

    Mike Parelli Mike Parelli Real Estate, LLC

    80 Leonard St, Stamford, CT 06906
  • /36

    $3,195,000

    • 6 Beds
    • 5.5 Baths
    • 5,442 Sq Ft

    219 Orchard St, Cos Cob, CT 06807

    Nestled behind thoughtful & mature landscaping, 219 Orchard St is a beautifully crafted Colonial that combines timeless architecture with a floor plan of 5,442sf on 4 finished levels. The stone façade, backyard privacy, light-filled rooms, oversized windows, high ceilings & rich millwork are some of the home's most wonderful features. The heart of the home is a bright, spacious kitchen that opens

    Jen Turano Compass Connecticut, LLC

    219 Orchard St, Cos Cob, CT 06807
  • /40

    $14,500,000

    • 6 Beds
    • 8 Baths
    • 8,738 Sq Ft

    379 Ocean Dr W, Stamford, CT 06902

    Completed in 2023 and designed by Michael Smith Architects, this extraordinary six bedroom waterfront residence offers more than 8,700 square feet of luxury living along one of Stamford's most coveted stretches of Ocean Drive West. Built two feet above FEMA flood elevation requirements and featuring sweeping views of Long Island Sound from every principal room, the home combines timeless coastal

    Joshua Weisman William Raveis Real Estate

    379 Ocean Dr W, Stamford, CT 06902
  • /30

    $1,495,000

    New Construction
    • 5 Beds
    • 3.5 Baths
    • 3,119 Sq Ft

    12 Walnut Ridge Ct, Stamford, CT 06905

    Don't miss this rare opportunity to own NEW construction in a desirable mid city, cul de sac neighborhood location. One of only two homes remaining in this 10-lot subdivision. This 5 bedroom, 3.5 bath colonial is comfortably proportioned and thoughtfully designed throughout with a relaxed, transitional style. The main level features an open and welcoming floor plan that easily connects living

    Barbara Hickey William Pitt Sotheby's Int'l

    12 Walnut Ridge Ct, Stamford, CT 06905
  • /14

    $3,600,000

    • 8 Beds
    • 3 Baths
    • 2,372 Sq Ft

    37 Arch St, Greenwich, CT 06830

    Potential for residential conversion in the heart of downtown Greenwich. Located just two doors from Greenwich Avenue and moments from the Metro-North train station, 37 Arch Street presents an exceptionally rare opportunity to create a one-of-a-kind in-town residence, mixed-use property, or continue as boutique commercial space. Situated within the Central Greenwich Business District zone, the

    Liz Eckert William Raveis Real Estate

    37 Arch St, Greenwich, CT 06830
  • /38

    $749,000

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    26 Birchwood Rd, Stamford, CT 06907

    Welcome Home to this spotless Colonial nestled in the highly sought-after Springdale neighborhood! Ideally located just a short stroll to local restaurants, shopping, & the Metro-North train, this home offers the perfect combination of convenience and comfort. Step inside to discover beautifully refinished hardwood floors & a bright, freshly painted open-concept living & dining room with sliding

    Terry LaPolice Berkshire Hathaway NE Prop.

    26 Birchwood Rd, Stamford, CT 06907
  • /38

    $12,100,000

    • 6 Beds
    • 13 Baths
    • 11,668 Sq Ft

    524 Lake Ave, Greenwich, CT 06830

    A gated drive opens to this elegant six-bedroom Mid-Country Manor overlooking tranquil views of Horseneck Brook. A stone courtyard introduces the dramatic four-story residence with elegant foyer, where sweeping butterfly staircases and limestone floors create a striking architectural welcome. From the gracious gallery hall, beautifully proportioned formal and informal rooms unfold-including

    Leslie McElwreath Sotheby's International Realty

    524 Lake Ave, Greenwich, CT 06830
  • /33

    $1,850,000

    • 3 Beds
    • 3 Baths
    • 1,860 Sq Ft

    313 Sound Beach Ave Unit 313, Old Greenwich, CT 06870

    One of only four condominiums - Federal Green Neighborhood Association - south of the village in Old Greenwich! This is a one-of-a kind opportunity to live in The Ferris Mortimer historic residence - CIRCA 1879 - expanded in 1968 and created into condo ownership in 1983Close distance to train, Old Greenwich Village and school.

    Ann Simpson BHHS New England Properties

    313 Sound Beach Ave Unit 313, Old Greenwich, CT 06870

Showing Results 41 - 80, Page 2 of 3

How to Buy a Home How to Finance a Home How to Sell a Home