Old Greenwich CT Real Estate & Homes for Sale

RARE OPPORTUNITY AND ENDLESS POSSIBILITIES ON OVERSIZED LOT IN THE HEART OF OLD GREENWICH! Charming, lived in and loved, this 1918 Colonial sits on one of OG's most desirable streets in The Village. The 3,670sf home blends timeless architecture with a welcoming layout and high ceilings. Additional FAR available for expansion. A wide wraparound front porch opens to well-proportioned entry hall, living room, dining room and family room. The generously sized kitchen features a large informal dining and seating area, opening to an expansive back deck and patio. The second floor features 4 bedrooms and bathroom, while the third floor offers a private 5th bedroom and bathroom. The 0.3-acre lot provides privacy thanks to the adjacent Innis Arden golf course and potential pool site (subject to approvals). An exceptional offering with unlimited potential in a truly desirable location near shops, school, train, and Tod's Point beach.

Stylish five-bedroom Contemporary provides a modern oasis with stunning pool, Ipe wood decks and secluded backyard on a quiet drive south of the village near shops, trains, school and beach. Striking architectural details ranging from maple wood floors, glass stair railings on three levels, high ceilings, expansive windows, sliding doors and skylights enhance 4,286 sq. ft. interior. Boasts sleek kitchen with Gaggenau appliances, Geoluxe counters and butler's pantry. Family and dining rooms with shared linear fireplace and games room, all with deck access for outdoor entertaining. First floor guest suite or office. Second floor has serene primary suite with spacious closet and luxurious bath plus three more ensuite bedrooms. Lower level with media room, mudroom and garage for up to eight cars.

Step into timeless and superior craftsmanship in this exceptional residence filled with custom features and luxurious details throughout. Dramatic 2 story foyer, custom wall mouldings and rich English oak hardwood floors that extend through the main living spaces. The centerpiece of the Living area is a shagreen tile fireplace, a striking and unique architectural focal point. The gourmet kitchen boasts a stunning waterfall-edge quartz countertop, custom cabinetry and a marble and glass tile backsplash. Convenience of touchless water faucet and the sophistication of a stunning beverage center bar.

Located near the heart of Old Greenwich, this classic Cape-style home is filled with warmth, character, and endless potential. The layout includes two bedrooms, one full bath, a dedicated office, formal living and dining rooms, and a sunny eat-in kitchen-offering both comfort and flexibility. Hardwood floors run throughout the main living areas, bedrooms, and office. Additional features include central air conditioning and a washer/dryer conveniently located on the main level. Head outside to a private back deck, ideal for relaxing or entertaining guests. Enjoy close proximity to Tod's Point, Binney Park, Perrot Library, and all the shops, dining, and conveniences of Old Greenwich Village-with schools and the train just minutes away.

Luxury new construction (Sept 2025) in a fabulous Riverside location! This beautifully designed home features a double height entrance with front to back views, a sophisticated living room, dining room with tray ceiling, and office with access to a covered terrace and outdoor fireplace. The gourmet kitchen with high-end appliances and breakfast area is next to the family room with a fireplace, wet bar, and large sliders opening out to the patio and level yard (with possible pool site) for indoor/outdoor entertainment. The primary suite with coffered ceiling boasts a fireplace, balcony, 2 walk-in closets, and luxury bath with cathedral ceiling, heated floors, steam shower, and tub. Also on the 2nd floor are 4 additional bedrooms, 2 of which are en-suite, and the spacious laundry room with sink. On the 3rd floor is a private office, playroom and half bath. The lower level offers 9' ceilings, a bedroom, full bath, media room with a wet bar, gym, and additional flexible space. Convenient mudroom off the 2-car garage. Close to town, shopping, schools, the train and beach.

Updated in 2025 this charming 1920's Shore Colonial mixes timeless turn of the century charm in an expansive over 4,000 sq. ft home in a great neighborhood near schools, playground, train and shopping. Welcoming front porch introduces a spacious main level with new gas fireplace/ shiplap and hearth and opens into the newly remodeled Chefs kitchen with marble countertops, breakfast bar seating, custom cabinetry and bar. This open plan living space seamlessly expands into the great room with breakfast room accentuated by French doors leading to the deck, allowing for great indoor/outdoor flow. New hardwood floors throughout. Second floor reveals primary suite with new luxurious bathroom, walk-in closet, two bedrooms, office and 1 full bath. With top floor bathroom and 2 additional bedrooms. Lower level was dug out to build a playroom (additional 600 sq. ft.) and more storage space. Unfinished attic above office adds more storage. Renovation includes new bathrooms with custom vanities, new front porch, new kitchen with custom cabinetry, new HVAC, landscaping, lighting and more.

A French Normandy Tudor home situated on a private peninsula within the Waterside community of Davenport Point. Nestled just beyond the Old Greenwich line within the coveted, private enclave of three neighborhood associations, this extraordinary French Normandy Tudor is a rare offering for the buyer seeking timeless elegance, architectural distinction, & a vibrant coastal lifestyle. Residents enjoy exclusive dock slips & this home also has deeded access to the private beach at Southfield Point-an exceptional combination of luxury & leisure. From the moment you step onto the grounds, you are transported to the pastoral beauty of the European countryside. Perennial plantings, landscaped gardens, & a pergola adorned w/ cascading wisteria create a romantic & tranquil setting that unfolds w/ storybook charm. The meticulously landscaped half-acre property offers both grandeur & intimacy-perfect for refined entertaining or peaceful reflection. Inside, modern sophistication harmonizes w/ old-world craftsmanship. The chef's kitchen is a culinary masterpiece, featuring a generous center island w/ a six-burner Viking gas cooktop, granite countertops, custom inlay cabinetry w/ crown molding, high-end stainless steel appliances, & a dedicated wet bar. This inviting space flows seamlessly into the formal dining room, where a bay window frames picturesque views of the lush backyard.

2 bedroom, 2 bath unit on 2nd floor with million dollar water views of Stamford Harbor and beyond. Live like you are on vacation year 'round in this one level condo featuring an open floor plan with 9' ceilings and hickory floors. The eat-in kitchen with high end appliances, wood cabinetry and granite counters is open to the spacious living room with gas fireplace and stunning water views. The master bedroom is on the water side with a master bath that features marble and double vanities. Guest bedroom features a marble bathroom in the hall. Harbor Point with restaurants galore is just a water taxi away. Private terrace overlooking the harbor is the perfect spot to start and end your day. 40' Boat slip avail at additional cost.

This attractive and spacious 5-bedroom Colonial on peaceful cul-de-sac in Riverside was rebuilt and expanded in 2006 with a modern floor plan. The interior extends to 4,100 sq ft. with recent upgrades and extra ceiling height in many of the rooms providing generous scale and abundant natural light. The large kitchen with breakfast area flows to the expansive family room with fireplace. French doors lead to the bluestone terrace and private garden and lawn area. The large first floor bedroom provides a flexible living space as an option for a playroom, library, game room or fitness center. The 2nd floor includes the primary suite, 3 additional bedrooms with 2 bathrooms and a laundry room. This lovely home is conveniently located a short distance to train, schools, tennis courts and more.

2024 *Fully Renovated* Riverside home on an oversized, flat lot with room to expand. Zoned for North Mianus and Eastern Middle schools. Brand new kitchen and bathrooms; new oak hardwood floors, doors and windows; all new mechanicals; en suite primary bedroom on ground level with private entrance; 3 additional bedrooms upstairs; office/flex room off the one car garage complete with electric car charging outlet; ample unfinished basement storage and dedicated laundry room. New deck with double sliding doors leads to the backyard adjacent to conservation land. In 2025 professionally installed Velux skylights in living room, Honeywell wired security system, and Culligan whole house water filtration system with reverse osmosis under sink. Short drive to parks, beach and downtown Old Greenwich.

Nestled on a beloved tree-lined cul-de-sac, this custom-built residence perfectly blends a traditional coastal Connecticut shingle style with a sun-filled, modern open-plan interior all just steps from Riverside Yacht Club, schools, and train. Thoughtfully designed, the home incorporates bespoke architectural elements including tall ceilings, custom millwork, expansive windows and wide-plank oak flooring throughout. With 6,600+ square feet of living space across two levels, it seamlessly blends formal and informal spaces to accommodate a variety of lifestyles. The gracious entry opens to wide hallways ideal for art placement. A handsome study, with rich paneling and a fireplace, delivers the perfect balance of functionality and style, serving as both a productive workspace and a peaceful retreat. The recently renovated kitchen is bright and contemporary with Caesarstone and Carrara marble countertops and a large island adjoining the coffered ceiling family room featuring long wall of windows. A classic tailored stairway leads to the second level and five spacious ensuite bedrooms, highlighted by a spectacular primary suite that is a true sanctuary featuring two fireplaces, a sitting area, and fabulous custom closets. An additional bedroom on the first floor is ideal for guests or staff. There is 3,200+ square feet of unfinished space in the lower level, with generous 9-foot ceilings providing incredible potential for customization.

Stunning fully renovated and expanded Colonial in the heart of Old Greenwich seamlessly blends timeless charm with modern luxury. Set on a quiet, tree-lined street just minutes from Old Greenwich Village, Metro North, and Tod's Point beach, this 5-bedroom, 4-bath home offers refined living in a prime location. The brand-new chef's kitchen showcases custom cabinetry, premium fixtures and finishes, and top-tier appliances including a Sub-Zero refrigerator and Wolf range. The kitchen opens to a sunlit dining room and inviting living room, while the family room features a cozy fireplace-perfect for entertaining or relaxing. A generous upstairs landing leads to five spacious bedrooms, including a vaulted-ceiling primary suite with a luxurious spa bath and soaking tub. The finished lower level offers a full bath, playroom, utility room, and extra space ideal for a guest room, gym, or au pair suite. Outside, a private backyard oasis features a sparkling pool and space for unforgettable gatherings. Every detail reflects exceptional craftsmanship, thoughtful design, and effortless elegance. This rare, move-in-ready gem offers sophisticated living in one of Greenwich's most sought-after neighborhoods.

This light and bright 5BR, 4.1BA Colonial, renovated to the studs in 2021, features modern conveniences with original charm. The open floor plan boasts a gourmet kitchen with quartz/marble countertops, new luxury baths, a woodburning fireplace, built-ins, convenient laundry/mudroom, and a finished 3rd floor with office, bedroom and full bath. Finished lower level (additional 365+ sf) with playroom and full bath. Spacious front porch, back deck, and French doors open out to the level yard. 2-car detached garage. Close to schools and town.

Lucas Point Association Fabulous shore colonial on oversize corner lot with private beach, dock and boatyard. A rare find, first time on the market in 60 years... Steps from Tod's Point, and close to Old Greenwich Village and Train

Welcome to this beautifully maintained tri-level townhouse in the sought-after Green Oaks complex. This spacious 2-bedroom, 1.5-bath home offers an open-concept main level with hardwood floors, crown molding, and a bright living room that flows into the dining area-perfect for entertaining. The kitchen features ample cabinet space, solid countertops, and easy access to your private patio, where you can grill and relax just steps from the community pool. Upstairs, you'll find two generously sized bedrooms, including a primary suite with a walk-in closet and a second bedroom with excellent closet space. The renovated bathrooms add a modern touch, including a stylish full bath with a glass-enclosed shower and sleek finishes. The finished lower level offers flexible living space with direct access to your private garage. Enjoy the unbeatable location close to grocery stores, Home Depot, I-95, and just minutes to the charm of Old Greenwich. This home combines comfort, convenience, and a low-maintenance lifestyle in a desirable community.

Sought after Riverside location showcases a stunning six-bedroom Colonial built by Sound Beach Partners with pool, porches, outdoor fireplace and grill on beautifully manicured .71 acres with private yard dotted with sequentially flowering trees. Offers easy access to trains, schools, water and Yacht Club. This pristine home exudes classic elegance with superb architectural details, wood floors, marble fireplaces and high ceilings. Dramatic double height entry leads into formal rooms with fireplaces, chef's kitchen with breakfast nook, family room with fireplace, library with wet bar and sunroom. Second floor boasts primary suite with balcony, walk-in closets; plus five bedrooms and four full baths. Play/rec room, gym, full bath and attached three-car garage complete lower level.

From a welcoming front porch to its cheerful canary-yellow door, 2 Lakeview Dr invites you in with warmth & personality. Nearly rebuilt in 2013 & offering approx. 3,000sf across 3 finished levels with existing expansion to 4-5 bedrooms, this 3-bed, 2.5-bath home is turnkey. The main level is filled with natural light & features an open-concept layout that connects a spacious dining room, elegant living area, stylish powder room, & a bright breakfast area. The gourmet kitchen is equipped with high-end features, like Wolf/Sub Zero, & flanked by a professionally organized pantry & radiant-heated mudroom. Upstairs, 2 large guest bedrooms share a full bath, & the primary suite boasts 2 walk-in closets & an en-suite bathroom with 2 sinks, a separate jet tub and marble-clad steam shower. A convenient laundry room completes the second floor. The fully finished lower level offers flexible space perfect for a playroom or entertainment space, home gym, media room, or private office. Just off the kitchen, French doors lead to a screened porch that opens to a patio and an expansive, level backyard (with irrigation) - ideal for outdoor entertaining. Cornered on a quiet street, 2 Lakeview Drive is ideally located close to schools, local shops and restaurants, and public transportation.

Welcome to 34 Brown Avenue, also known as 18 Brown Avenue-a townhouse-style condominium offering comfort, convenience, and a fantastic location. This well-laid-out unit features 2 spacious bedrooms, 1 full bathroom, and a partially finished basement that provides added flexibility for storage, recreation, or work-from-home space. Ideally situated within walking distance to vibrant downtown Stamford, you'll enjoy easy access to a wide array of shopping, dining, and entertainment options-everything you need just steps from your front door. Whether you're a first-time buyer or an investor seeking a conveniently located property, this is an opportunity you won't want to miss. Listed while occupied, no showings allowed. Offered strictly "as-is", this property is subject to no contingencies or inspections. The buyer will be responsible for obtaining possession of the property upon closing. No interior photos available.

This Classic Colonial thoughtfully designed and custom built for the current owner is sited on .24 level acres. Quality construction with high ceilings, large windows and hardwood floors. The traditional layout features a welcoming double-height marble entry foyer, formal living and dining rooms and a gourmet kitchen adjacent to an enormous family room with stone fireplace. French doors lead to the rear deck for peaceful outdoor enjoyment. Second floor is complete with 4 bedrooms including a gracious primary suite with fireplace, 3 full baths and separate laundry room. Finished lower level can be used as playroom, gym, or home theater. Oversized two car garage, walk-up attic, and numerous additional features. Close to train, highway and North Mianus Elementary School.

Exquisite 2016 French Normandy manor designed by premier architect, Douglas VanderHorn blends classic elegance with 3 levels of stunning modern aesthetics in coveted Riverside association with Shoreline pool and neighborhood private beach. Sophisticated, custom crafted interior with Italian marble mantels framing four fireplaces, quarter-sawn white oak flooring, 10 ft. ceilings, French doors to multiple terraces offers extraordinary 21st century state-of-the-art luxury. Richly paneled living room/library with Long Island Sound views; magnificent dining and family rooms; fabulous gourmet kitchen. Five en suite bedrooms including the sublime primary with fireplace and Waterworks marble bath. State of the art systems including Geothermal heat, Lutron System, 1,000+ bottle wine cellar.

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.

Well-maintained and competitively priced townhouse hardwood flooring on the main level. The kitchen includes granite countertops and stainless steel appliances, opening to a living room with custom wood trim and a fireplace. Second level offers two bedrooms, a full bathroom, and in-unit laundry. The third floor boasts a spacious primary suite with city views, a walk-in closet, and an ensuite bath with double vanity and soaking tub. Convenient location near downtown, train station, and local amenities. Assumes existing loan is available, subject to approval.

Where lifestyle, livability, and versatility meet... all your family & friends, too. Set in Cos Cob's tight-knit Loughlin Park, this 5 Bed home is in a prime location. Seconds to the train, a food scene, & the Park. With 3000 sqft of livability this home is a neighborhood hub. A garage & breezeway lead to open living, kitchen, & dining with a fireplace. Easy access to a grill, putting green, & fully turfed yard. A covered outdoor area connects to a lower level with half bath. The versatility is a 5 bed layout. On the main level are 3 beds & 3 baths, one a main suite. Beds 4 & 5 are on the 2nd level connected to a huge family room, with bath. It's set up perfectly for a guest suite & or dual home offices. The 2 bed wing provides a runway to set up roots for a forever home.

Don't miss this rare opportunity to own a spacious and versatile seven bedroom, five and a half bath colonial in sought-after Cos Cob! Set on a generous half-acre lot, this home offers 4,258+/- square feet of flexible living space-ideal for multi-generational living arrangement-with a private entrance for added comfort and independence. The main level features a welcoming living room, bright eat-in kitchen with sliders to an oversized deck with built-in benches-ideal for outdoor entertaining-and a spacious bonus room great for a home office, playroom, guest suite, or gym. The finished walk-out lower level includes a cozy family room with a fireplace that opens to a patio and expansive yard. Located close to schools, parks, and the train, this home offers space and flexibility.

Charming and updated 4BR/2BA Colonial in Stamford's desirable Hubbard Heights neighborhood! This sun-filled home blends 1920s character with thoughtful updates including fresh interior paint, new crown molding, and refinished hardwood floors. The renovated kitchen features high-end custom cabinetry, honed granite counters, and stainless steel appliances. Both full baths are remodeled with marble and designer fixtures. Smart home features include smart thermostats, Yale keyless entry, smart light switches, SimpliSafe security, and remote blinds in the living room. Extensive electrical upgrades include recessed lighting, updated fixtures, bedroom ceiling lights, and garage wiring with a smart opener. A Level 2 EV charger is also installed. The walk-up attic is fully insulated with heat and A/C, offering expansion potential. Enjoy a sunny front porch and spacious back deck overlooking your yard filled with perennial plantings. Close to Metro-North, I-95, downtown, parks, and shopping. Move-in ready and full of charm-don't miss it!