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Colonial Homes for Sale in Old Greenwich, CT

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  • /29

    $1,849,999

    • 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

    Agent Photo

    Spencer Sodokoff

    Houlihan Lawrence

    (475) 262-8302

    43 High St, Greenwich, CT 06830
  • /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

    Agent Photo

    Megan Sullivan

    Douglas Elliman of Connecticut

    (475) 265-6175

    15 Vineyard Ln, Greenwich, CT 06831
  • /2

    $4,250,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 4.5 Baths
    • 4,937 Sq Ft

    24 Annjim Dr, Greenwich, CT 06830

    Framed by mature trees on an oversized .33 acre lot, this beautifully refreshed 4 / 5 bed custom built Colonial is full of sunlight + tucked away on a quiet cul-de-sac 3 mins from town. Bright, newly painted interiors feature wood floors, 2 FP's + classic detailing. A double-height entry leads to elegant formal rooms + an open chef's kitchen w banquette seating + high end appliances, flowing to a

    Amanda Bates Houlihan Lawrence

    24 Annjim Dr, Greenwich, CT 06830
  • /40

    $2,695,000 Coming Soon

    • 6 Beds
    • 6.5 Baths
    • 4,815 Sq Ft

    83 Sea Beach Dr, Stamford, CT 06902

    Welcome to this stately colonial, one of only 19 homes with deeded rights to the coveted Sea Beach Association on Shippan Point. Enjoy updated living in this spacious home, with water views from most of the rooms. Professionally decorated with a comfortable/homey feel, the versatile floor plan offers plenty of options for formal and informal entertaining. The heart of the home is the kitchen

    Carolyn Brook William Pitt Sotheby's Int'l

    83 Sea Beach Dr, Stamford, CT 06902
  • /49

    $3,499,000

    • 5 Beds
    • 4.5 Baths
    • 5,389 Sq Ft

    399 Stanwich Rd, Greenwich, CT 06830

    Set amid scenic beauty, this custom-built Colonial offers over 5,300± square feet of elegant living space across four levels, complete with an indoor swimming pool and a charming guest cottage. Sun-filled formal living and dining rooms showcase soaring ceilings and beautiful natural light, while the kitchen with breakfast room opens to a comfortable family room. The serene primary suite provides

    Leslie McElwreath Sotheby's International Realty

    399 Stanwich Rd, Greenwich, CT 06830
  • /46

    $2,495,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,717 Sq Ft

    13 Mortimer Dr, Old Greenwich, CT 06870

    Welcome to 13 Mortimer Drive, a charming Colonial Cape nestled in the highly sought-after ''Edgewater'' neighborhood of Old Greenwich, just south of the village. This lovely home offers 3 bedrooms and 2 1/2 bathrooms, complemented by a beautifully level, fenced yard perfect for outdoor living. A detached, heated bonus space provides the perfect setting for a home office or studio. Ideally located

    Edineia Bickerstaff BHHS New England Properties

    13 Mortimer Dr, Old Greenwich, CT 06870
  • /8

    $8,995,000 New Construction

    • 6 Beds
    • 10 Baths
    • 10,216 Sq Ft

    2 Stillman Ln, Greenwich, CT 06831

    Exceptional 2026 new construction offering resort-style living across a main residence + pool house on a private one-acre lot close to town. Designed by Schettino, the main house features 5 bedrooms, 7 full baths + 2 powder rooms with a seamless, light-filled floor plan ideal for entertaining and everyday living. The second floor incl a luxurious primary suite w balcony, dual walk-in closets, +

    Amanda Bates Houlihan Lawrence

    2 Stillman Ln, Greenwich, CT 06831
  • /38

    $3,250,000

    • 5 Beds
    • 3.5 Baths
    • 4,170 Sq Ft

    19 Thomasina Ln, Darien, CT 06820

    Meticulously maintained and built in 2016 by Doherty & Deleo Development, this five-bedroom colonial offers four levels of thoughtfully designed living on a highly desirable in-town cul-de-sac. The home features a bright open layout, 9' ceilings, hardwood floors throughout, and a spacious kitchen with walk-in pantry that flows seamlessly into the main living areas. An oversized mudroom, powder

    Robin Halsey Compass Connecticut, LLC

    19 Thomasina Ln, Darien, CT 06820
  • /30

    $8,750,000

    • 5 Beds
    • 8 Baths
    • 9,619 Sq Ft

    10 Birch Ln, Greenwich, CT 06830

    Impeccably constructed colonial in Greenwich's Golden Triangle on 1.35 acres with pool bordered by a scenic pond. A double-height foyer leads to the formal living room and library, both with fireplaces. Chef's kitchen adjoins the family room with fireplace, butler's pantry, and formal dining room. French doors open to terrace with heated pool, barbecue and firepit. Mudroom and attached 4-car

    Joseph Barbieri Sotheby's International Realty

    10 Birch Ln, Greenwich, CT 06830
  • /40

    $15,945,000

    • 6 Beds
    • 10 Baths
    • 11,211 Sq Ft

    30 Meadowcroft Ln, Greenwich, CT 06830

    Sited on over two acres of private, west-facing land in the heart of Greenwich's coveted Golden Triangle, this architectural modern masterpiece commands attention. Designed in collaboration with renowned architect William D. Earls, this 11,000+ sq ft six-bedroom estate showcases timeless design, masterful craftsmanship, and refined sophistication. Completed in 2018, the residence blends bold

    Jeffrey Jackson Corcoran Centric Realty

    30 Meadowcroft Ln, Greenwich, CT 06830
  • /2

    $2,750,000

    • 5 Beds
    • 5.5 Baths
    • 3,482 Sq Ft

    43 Dubois St, Darien, CT 06820

    A beautiful modern interpretation of a traditional colonial, this 3,482 SF residence was built by award winning Hemingway Construction and is ideally located near the train, town, beaches and Great Island all short walk away. The neighborhood is zoned for Blue Ribbon award-winning Hindley Elementary School, where everyone can enjoy biking and walking to school together. The first floor features

    Chichi Mayhew Compass Connecticut, LLC

    43 Dubois St, Darien, CT 06820
  • /4

    $900,000

    • 5 Beds
    • 2 Baths
    • 2,815 Sq Ft

    424 Willett Ave, Port Chester, NY 10573

    This two-family Colonial-style home features two bedrooms, two full baths, two eat-in kitchens, and a two-car garage. The information provided is estimated to the best of our abilities at this time.

    Todd Yovino Island Advantage Realty LLC

    424 Willett Ave, Port Chester, NY 10573
  • /31

    $2,350,000

    • 5 Beds
    • 5 Baths
    • 3,598 Sq Ft

    201 Shore Rd, Greenwich, CT 06830

    Conveniently located near town: on sought-after Belle Haven Peninsula, this 2008 expansion 5-bed, 5-bath home boasts breathtaking views of Greenwich Harbor. Perfectly designed for harborside living & entertaining, the sunlit gourmet chef's kitchen & great room feature an island, custom cabinetry, and a wall of windows with glass doors opening to a deck overlooking the harbor & park. The spacious

    Meg McAuley Kaicher Coldwell Banker Realty

    201 Shore Rd, Greenwich, CT 06830
  • /42

    $13,995,000

    • 6 Beds
    • 8 Baths
    • 10,286 Sq Ft

    7 Parsonage Rd, Greenwich, CT 06830

    An extraordinary newly constructed residence in the heart of Greenwich, Seven Parsonage Road is a masterfully crafted white brick manor on 1.12 acres, defined by timeless elegance and modern sophistication. Spanning four expansive light filled levels served by an elevator, this six-bedroom, six full and two half-bathroom home offers over 10,200+/- square feet of meticulously designed living

    Leslie McElwreath Sotheby's International Realty

    7 Parsonage Rd, Greenwich, CT 06830
  • /27

    $2,995,000

    • 4 Beds
    • 2.5 Baths
    • 2,998 Sq Ft

    45 Hillcrest Park Rd, Old Greenwich, CT 06870

    Set on 1.35 level acres in the desirable Hillcrest Park private association, this 2025 renovated 4-bedroom, 2.1-bath home offers move-in ready living with expansion potential. 1st floor-large living room with french doors to welcoming covered porch, sun-filled family room with french doors to stone terrace, eat-in-kitchen, and generously sized mudroom. 2nd floor-spacious primary suite with

    Alexandra Kelly Sotheby's International Realty

    45 Hillcrest Park Rd, Old Greenwich, CT 06870
  • /21

    $3,795,000

    • 5 Beds
    • 4.5 Baths
    • 4,187 Sq Ft

    16 Summit Rd, Riverside, CT 06878

    Stop-the-Car - come experience the inside of this 4,187 sq ft Riverside Colonial, thoughtfully updated to today's standards. This is a rare opportunity to own a turnkey Riverside home that combines location, space, and everyday livability near Riverside Elementary, Binney Park, Old Greenwich Village, and two Metro-North stations. This 5-bedroom, 4.1-bath home blends classic architecture with the

    Felipe Dutra Leite Compass Connecticut, LLC

    16 Summit Rd, Riverside, CT 06878
  • /8

    $7,995,000

    • 8 Beds
    • 11.5 Baths
    • 10,646 Sq Ft

    68 Dearfield Dr, Greenwich, CT 06831

    Perched high on a hill in downtown Greenwich, 66 Dearfield is unparalleled in its grandeur with 10,646 square feet of luxury living spanning 4 floors. Close to Greenwich Library, Greenwich Avenue, the train and all downtown amenities. This exquisite colonial boasts stone chimneys with extra height ceilings on each floor. Upon entry, the 2 story foyer nestled between the living room and dining

    Nina Frandson BHHS New England Properties

    68 Dearfield Dr, Greenwich, CT 06831
  • /30

    $4,995,000

    • 4 Beds
    • 3.5 Baths
    • 6,915 Sq Ft

    177 Indian Head Rd, Riverside, CT 06878

    One of Riverside's most coveted waterfront enclaves, this elegant colonial offers refined living with a sense of privacy and tranquility set on nearly 2 acres. A new cedar just completed in 2025. The first level features a living room with fireplace, expansive family room, formal dining room, and sunny gallery passageway with French doors. Access the secluded back patio from the open kitchen,

    Remy Cook Corcoran Centric Realty LLC

    177 Indian Head Rd, Riverside, CT 06878
  • /39

    $2,995,000

    • 3 Beds
    • 2 Baths
    • 2,859 Sq Ft

    40 Bruce Park Dr, Greenwich, CT 06830

    Nestled on a scenic knoll in the heart of Greenwich just moments from downtown & directly across from picturesque Bruce Park, this fully renovated home offers the perfect blend of timeless mid-century design & modern luxury. Boasting an open-concept layout, the sun-drenched interior features three spacious bedrooms & two elegant bathrooms. The gourmet kitchen flows effortlessly into the dining &

    Danielle Claroni Sotheby's International Realty

    40 Bruce Park Dr, Greenwich, CT 06830
  • /31

    $3,195,000

    • 3 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

    403 Stanwich Rd, Greenwich, CT 06830

    Come see this total and complete renovation!. New design, expanded Sq ft, custom hand built kitchen, all new mechanicals, roof, siding, windows, baths, etc. New granite pool deck, private 1.23 acres on desirable Stanwich rd. location.

    Stephen Kane Sotheby's International Realty

    403 Stanwich Rd, Greenwich, CT 06830
  • /38

    $4,750,000

    • 6 Beds
    • 8 Baths
    • 6,762 Sq Ft

    66 Stanton Rd, Darien, CT 06820

    Welcome to 66 Stanton Road. Set on 1.34 landscaped acres, this classic 1938 clapboard colonial blends architectural charm with thoughtful updates, including a full renovation and expansion completed in 2009. Designed for effortless living and entertaining, the home offers refined formal rooms and relaxed gathering spaces. A gracious foyer with sweeping curved staircase is flanked by sunlit living

    Amanda Spatola Houlihan Lawrence

    66 Stanton Rd, Darien, CT 06820
  • /65

    $8,395,000

    • 6 Beds
    • 9 Baths
    • 8,370 Sq Ft

    56 Winthrop Dr, Riverside, CT 06878

    Completed in '24 by Edgewater Development and architect Steven Mueller, this exceptional residence is set on one of Riverside's most sought after streets. Positioned on .57 acres, the home blends modern sophistication with timeless design.Spanning 3 levels, sun filled interiors feature clean architectural lines and refined finishes throughout. The main level is designed for both entertaining

    Jenny Allen Compass Connecticut, LLC

    56 Winthrop Dr, Riverside, CT 06878
  • /30

    $1,375,000

    • 3 Beds
    • 3 Baths
    • 2,063 Sq Ft

    11 Patton Dr, Darien, CT 06820

    The seller has requested all offers to be submitted by Sunday at 5PM. The sellers attorney is Michael Murray 203-358-0800 mmurray@dmoc.com Located in one of the most sought-after CT gold coast communities, this meticulously maintained 3-bedroom, 3 full bath expanded colonial home offers an open, light-filled layout designed for everyday living and entertaining. Highlights include a living room

    Holly Hawes Compass Connecticut, LLC

    11 Patton Dr, Darien, CT 06820
  • /21

    $2,999,999

    • 5 Beds
    • 4 Baths
    • 3,302 Sq Ft

    51 Glen Rd, Greenwich, CT 06830

    Close to town from this rare in-town Greenwich gem -- a corner lot home on a quiet cul-de-sac, just steps from Greenwich Avenue's shops, restaurants, and cafés, the Greenwich Library, renowned private schools including Brunswick School and Greenwich Academy, and minutes to Metro-North Greenwich Station, with effortless access to parks, the waterfront, and all that downtown Greenwich offers. This

    Monica Webster Douglas Elliman of Connecticut

    51 Glen Rd, Greenwich, CT 06830
  • /26

    $1,495,000

    • 4 Beds
    • 2 Baths
    • 1,759 Sq Ft

    25 Hillside Ave, Darien, CT 06820

    Sun-filled, Beachy Colonial ideally located beside a coveted private cul-de-sac just moments from the Darien train & Darien Commons. Thoughtfully updated with numerous improvements and upgrades, including a stylish, top-of-the-line eat-in kitchen designed for both everyday living and effortless entertaining.The open, flexible floor plan offers the rare option of a primary suite on either the main

    Kathryn Bates Compass Connecticut, LLC

    25 Hillside Ave, Darien, CT 06820
  • /18

    $869,000

    • 2 Beds
    • 1.5 Baths
    • 1,463 Sq Ft

    115 Top Gallant Rd Unit 6, Stamford, CT 06902

    Enjoy the rare combination of condominium convenience and the privacy of a single-family home in this freestanding townhouse ideally located on the Old Greenwich-Stamford border. Offering an effortless lifestyle without the demands of traditional homeownership, this turnkey unit is equally suited for year-round living or as a sophisticated weekend retreat. Additional highlights include a

    Melinda Chanaud BHHS New England Properties

    115 Top Gallant Rd Unit 6, Stamford, CT 06902
  • /35

    $3,195,000

    • 6 Beds
    • 5.5 Baths
    • 4,300 Sq Ft

    20 Sound Beach Ave, Greenwich, CT 06870

    NEW BUILD in Old Greenwich, close to BEACH! Greeted with Wide Plank White Oak hardwood floors and high end finishes throughout the home, it truly is a masterpiece. Open-concept Kitchen is full of gold accent fixtures and JennAir appliances, with a large waterfall Quartz Carrara Gold Island. Entertain your guests while admiring the electric heating fireplace in the living room which also has

    Kaltrina Xhema-Latifi Higgins Group Greenwich

    20 Sound Beach Ave, Greenwich, CT 06870
  • /31

    $849,000

    • 3 Beds
    • 2.5 Baths
    • 2,062 Sq Ft

    408 Strawberry Hill Ave, Stamford, CT 06902

    Well cared for Fieldstone colonial in most convenient location. Spacious rooms, living room with fireplace and hardwood floors, formal dining room,large newer eat-in-kitchen with pantry. Sliders open onto the durable maintenance free deck where you can enjoy outdoor dining while you watch loved ones play safely in the fenced in yard. Primary bedroom with tray ceiling, huge en-suite bath and walk

    Lisa Linzer L & S Realty

    408 Strawberry Hill Ave, Stamford, CT 06902
  • /24

    $1,350,000

    • 5 Beds
    • 2.5 Baths
    • 3,702 Sq Ft

    42 Hastings Ln, Stamford, CT 06905

    *Please submit offers by Monday 3/23 at 2pm* Welcome HOME to 42 Hastings Lane! Nestled on a quiet cul-de-sac in Stamford's highly sought-after Springdale neighborhood, this beautifully maintained and tastefully updated home truly checks every box. The home features four spacious bedrooms upstairs along with a convenient ground-floor bedroom that's perfect for guests or a work-from-home office.

    Rachel Levi Compass Connecticut, LLC

    42 Hastings Ln, Stamford, CT 06905
  • /36

    $3,095,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 6 Baths
    • 5,735 Sq Ft

    25 Patricia Ln, Darien, CT 06820

    Welcome to 25 Patricia Lane, where timeless elegance meets modern convenience. Nestled on a highly desirable street in Darien, this 2006 Hemingway built pristine 5-bedroom, 4 full and 2 half-bath Colonial offers over 5,700 square feet of beautifully designed living space. Step inside to discover a bright, airy layout with exceptional flow, perfect for both everyday living and entertaining. The

    Keiley Fuller Compass Connecticut, LLC

    25 Patricia Ln, Darien, CT 06820
  • /16

    $4,250,000

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    6 Benedict Place, Greenwich, CT 06830

    Welcome to this newly renovated 3,500 sq ft gem nestled in the heart of downtown Greenwich, CT. A quick walk to MetroNorth and steps away from the amenities, restaurants and shops, this unique space is designed with the modern executive or family in mind. The home seamlessly blends comfort, functionality, and style and can be adapted effortlessly to suit your needs.Benedict Place is

    Wendy Hill Sotheby's International Realty

    6 Benedict Place, Greenwich, CT 06830
  • /36

    $5,350,000

    • 4 Beds
    • 5 Baths
    • 5,417 Sq Ft

    129 Doubling Rd, Greenwich, CT 06830

    Set on 1.79 gated acres in the heart of mid-country Greenwich, this extraordinary property offers a rare combination of complete privacy, refined elegance, and modern luxury living. Tucked far back from a quiet country road and within a neighborhood of $10+ million estates, this property unfolds like a private botanical retreat--featuring sweeping perennial gardens, flowering shrubs, magnificent

    Jeffrey Jackson Corcoran Centric Realty

    129 Doubling Rd, Greenwich, CT 06830
  • /26

    $2,195,000

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

    17 Maple Dr, Old Greenwich, CT 06870

    This fully renovated and expanded in 2024 home features an open-plan living/family room with electric fireplace, that flows into the dining room. Gourmet kitchen with Thermador appliances and eat-in area that opens out to the stone patio and fenced yard. 1st floor bedroom with full bath is also ideal as an office. The 2nd floor primary bedroom with vaulted ceiling is a relaxing space with a

    Gloria Gimenez-Ferrer BHHS New England Properties

    17 Maple Dr, Old Greenwich, CT 06870
  • /28

    $6,250,000 New Construction

    • 5 Beds
    • 6 Baths
    • 4,500 Sq Ft

    30 Meadowbank Rd, Old Greenwich, CT 06870

    Exceptional new construction, scheduled for late summer 2026 completion. This modern coastal residence offers 4-5 ensuite bedrooms, signature European windows, and expansive open-plan living. Full-height sliders open to decks on the first and second floors. Features include a custom white oak kitchen, bespoke bathrooms, home office or optional first-floor bedroom, two-car garage with mudroom, and

    Mary Childs BHHS New England Properties

    30 Meadowbank Rd, Old Greenwich, CT 06870
  • /21

    $750,000

    • 3 Beds
    • 1.5 Baths
    • 2,526 Sq Ft

    15 Tremont Ave, Stamford, CT 06906

    1925 Colonial with the charm and character of yesterday . Updated kitchen & bath located on a tree lined street in Glenbrook less than 1 mile from the Glenbrook Train Station. Entry foyer opens to spacious living room with window seat, hardwood floors and sunroom/office for additional family space, formal dining room has built-in corner cabinet. The updated white kitchen has granite counter tops,

    Ann Simpson BHHS New England Properties

    15 Tremont Ave, Stamford, CT 06906
  • /13

    $875,000

    • 3 Beds
    • 3 Baths
    • 4,398 Sq Ft

    139 Wyndover Ln, Stamford, CT 06902

    Westover Colonial home set on .69 acres built in 1960. Occupied, DO NOT disturb occupants. Being sold as-is via auction. new owner to assume responsibility for occupants. Cash Only

    Susan Frederico Aspen Realty Group

    139 Wyndover Ln, Stamford, CT 06902
  • /37

    $3,595,000

    • 6 Beds
    • 6 Baths
    • 5,112 Sq Ft

    15 Desiree Dr, Greenwich, CT 06830

    Set on a cul-de-sac, this inviting Colonial offers a bright interior, flexible layout, and six bedrooms on two quiet acres. A welcoming foyer with soaring ceiling opens to the sunlit dining room with bay window and living room with fireplace and doors leading to a large deck overlooking the backyard. The kitchen has been expanded and renovated, featuring a built-in desk and breakfast area with

    Julie Church Houlihan Lawrence

    15 Desiree Dr, Greenwich, CT 06830
  • /40

    $6,345,000

    • 5 Beds
    • 5.5 Baths
    • 6,233 Sq Ft

    164 Stanwich Rd, Greenwich, CT 06830

    Welcome to this exquisitely updated Colonial on 1.16 landscaped acres near Greenwich Country Club and minutes from town. A grand foyer with gleaming hardwood floors and sweeping staircase introduces the elegant interior. The main level includes a formal living room, dining room, two studies, and a gourmet kitchen with Wolf appliances, Palissandro marble, Thermador coffee station, a custom wet bar

    Jeffrey Jackson Corcoran Centric Realty

    164 Stanwich Rd, Greenwich, CT 06830
  • /40

    $1,990,000

    • 5 Beds
    • 4.5 Baths
    • 4,665 Sq Ft

    1209 Westover Rd, Stamford, CT 06902

    Extraordinary opportunity. A gracious country estate in the highly sought-after Westover neighborhood, set on a stately and private property with mature gardens, in-ground pool, fountain and large patio ideal for outdoor entertaining. This custom built 5-bedroom, 5-bath home blends classic architecture with subtle European designer influences throughout. Meticulous care devoted to upgrade this

    Catherine Aaron Berkshire Hathaway NE Prop.

    1209 Westover Rd, Stamford, CT 06902
  • /39

    $845,000

    • 3 Beds
    • 2.5 Baths
    • 2,016 Sq Ft

    23 Congress St, Stamford, CT 06902

    This completely renovated single-family home features 3 bedrooms, 2.5 bathrooms and modern updates throughout. Hardwood floors, shiplap accents, high-quality tile and hardware selections add style and durability. The Eat-in kitchen includes LG stainless steel appliances, quartz countertops and an under-counter beverage cooler plus breakfast bar. The home also offers a dedicated laundry room on

    Gregorio Pansino BHGRE Shore & Country

    23 Congress St, Stamford, CT 06902

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