Old Greenwich, CT Houses for Sale

/27
$584,999
- 3 Beds
- 1 Bath
- 1,289 Sq Ft
18 Oaklawn Ave, Stamford, CT 06905

Please come see this beautiful antique home in the Newfield section of Stamford. This house has Three Beautiful Large Bedrooms and Two Full Baths. This New England style cape has a wrap around porch with skylights. Built in 1790 this home has very unique features: wide plank flooring, built-ins, nooks, clawfoot tub, and antique windows. The main level has a large Living Room w/fireplace and

Kenny Clyburn BHGRE Shore & Country

18 Oaklawn Ave, Stamford, CT 06905
/35
$849,000
- 4 Beds
- 2.5 Baths
- 2,588 Sq Ft
25 Wire Mill Rd, Stamford, CT 06903

Charming and manageable Cape Cod-style home on a spacious lot, ideally located near the Merritt Parkway with easy access to top restaurants and a convenient Greenwich, New Canaan, Darien, Rye Brook, Bedford, Norwalk & NYC commute. Enjoy the comfort of a first-floor primary bedroom and the added versatility of a finished basement.

Christian Perry Sotheby's International Realty

25 Wire Mill Rd, Stamford, CT 06903
/20
$1,595,000
- 4 Beds
- 3 Baths
- 2,259 Sq Ft
52 Center Dr, Old Greenwich, CT 06870

There is more than meets the eye in this sweet colonial on oversized lot in R7 zone. A prior expansion creates flexible space on the first floor. A spacious living room with fireplace is flanked by an office/playroom, ample formal dining room and a first floor primary bedroom with full bath which can alternately be used as a family room. Archways lend a special charm to the formal rooms.

Lisa DeFonce Houlihan Lawrence

52 Center Dr, Old Greenwich, CT 06870
/21
$2,325,000
- 3 Beds
- 2 Baths
- 2,220 Sq Ft
23 Beach Dr, Darien, CT 06820

Ideally located in the heart of the sought-after Noroton Manor Association and within the coveted Hindley Blue Ribbon school district, this delightful three-bedroom, two-bath home offers the perfect blend of charm and convenience. Enjoy exclusive access to a private beach and tennis courts, all within a welcoming, close-knit community. Inside, you'll find a spacious eat-in kitchen with an island,

Janine Tienken Houlihan Lawrence

23 Beach Dr, Darien, CT 06820
/51
$11,400,000
- 8 Beds
- 10 Baths
- 10,935 Sq Ft
151 Old Church Rd, Greenwich, CT 06830

''Oak Castle Farm'', an extraordinary 7-bedroom turn-of-the-century English-style granite and shingle home, masterfully renovated and expanded under the supervision of noted architect, Alisberg Parker. Stunning 2014 transition incorporates relaxed grandeur with all modern-day luxuries. Exquisite detail, quality and scale with high ceilings throughout. Spectacular landscape and manicured grounds

John McAtee Coldwell Banker Realty

151 Old Church Rd, Greenwich, CT 06830
/40
$5,495,000
- 6 Beds
- 5.5 Baths
- 6,543 Sq Ft
86 Wallacks Dr, Stamford, CT 06902

Prestigious Waterfront Estate at Wallack's Point Experience the pinnacle of coastal luxury with this once-in-a-lifetime opportunity to own 1.46 acres of DIRECT Long Island Sound frontage in the gated enclave of Wallack's Point. With sweeping, unobstructed water views and nightly sunsets that feel like art, this premier waterfront property is among the most coveted on the Connecticut shoreline.

Carla Kupiec William Raveis Real Estate

86 Wallacks Dr, Stamford, CT 06902
/31
$6,500,000
- 6 Beds
- 4 Baths
- 2,833 Sq Ft
0 Rich Island Unit 24092237, Greenwich, CT 06830

A one-of-a-kind offering, this property provides sweeping views of Long Island Sound and the allure of your own island. The expansive half-acre property, shaded by mature trees, also features its own boat dock and two boats for exploration of nearby waters and islands. Meticulously landscaped grounds with beautiful perennial gardens provide a picturesque setting for outdoor events. A beautiful

Margriet McGowan Sotheby's International Realty

0 Rich Island Unit 24092237, Greenwich, CT 06830
/37
$6,500,000
- 6 Beds
- 4 Baths
- 2,833 Sq Ft
0 Rich Island Unit KEY855821, Greenwich, CT 06830

A one-of-a-kind offering, this property provides sweeping views of Long Island Sound and the allure of your own island. The expansive half-acre property, shaded by mature trees, also features its own boat dock and two boats for exploration of nearby waters and islands. Meticulously landscaped grounds with beautiful perennial gardens provide a picturesque setting for outdoor events. A beautiful

Margriet McGowan Sotheby's International Realty

0 Rich Island Unit KEY855821, Greenwich, CT 06830
/37
$6,500,000
- 6 Beds
- 4 Baths
- 2,833 Sq Ft
0 Rich Island Unit 122625, Greenwich, CT 06830

A one-of-a-kind offering, this property provides sweeping views of Long Island Sound and the allure of your own island. The expansive half-acre property, shaded by mature trees, also features its own boat dock and two boats for exploration of nearby waters and islands. Meticulously landscaped grounds with beautiful perennial gardens provide a picturesque setting for outdoor events. A beautiful

Margriet McGowan Sotheby's International Realty

0 Rich Island Unit 122625, Greenwich, CT 06830
/26
$2,350,000
- 3 Beds
- 2.5 Baths
- 2,950 Sq Ft
2 Lakeview Dr, Greenwich, CT 06878

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

Jen Turano Compass Connecticut, LLC

2 Lakeview Dr, Greenwich, CT 06878
/38
$2,175,000
- 5 Beds
- 4.5 Baths
- 2,775 Sq Ft
39 Riverside Ave, Riverside, CT 06878

This light and bright 5BR, 4.1BA Colonial, renovated to the studs in 2021, features modern conveniences with original charm. The open floor plan offers 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

Gloria Gimenez-Ferrer BHHS New England Properties

39 Riverside Ave, Riverside, CT 06878
/40
$2,350,000
- 5 Beds
- 3.5 Baths
- 3,634 Sq Ft
551 River Rd, Cos Cob, CT 06807

Bright newer five bedroom Center Hall Colonial near North Mianus school and minutes to Eastern Middle school , Riverside and Cos Cob shopping and RR stations. Third floor separate suite with bedroom, bath and office or sitting room. Hardwood floors , fenced in backyard. Great flow for day-to-day indoor and outdoor living and entertaining. Total Sq. footage includes 535 sq. ft. below grade.

Maria Arning BHHS New England Properties

551 River Rd, Cos Cob, CT 06807
/50
$6,800,000
- 5 Beds
- 10 Baths
- 7,632 Sq Ft
21 Calhoun Dr, Greenwich, CT 06831

Welcome to ''Park Hill'', a stunning English Tudor Revival Manor known as ''The House of Seven Gables''. Updated in 2025, this historic gem nestled in the heart of Greenwich on a 1.81-acre oversized lot, offers privacy & a unique blend of timeless elegance with modern conveniences. Located in the desirable Calhoun Drive Association, this property boasts both beauty & charm. The manor's

Danielle Claroni Sotheby's International Realty

21 Calhoun Dr, Greenwich, CT 06831
/42
$27,950,000
- 8 Beds
- 11.5 Baths
- 13,428 Sq Ft
45 Binney Ln, Old Greenwich, CT 06870

This unparalleled custom-built modern waterfront estate, winner of 2021 HOBI-award, is a true oasis with 300'+ water frontage, pool, guest house, boat house, spa, expansive terraces integrated with gardens and deep water pier. Joeb Moore + Partners, Arthur Dunnam for Jed Johnson Studio, Reed Hilderbrand & Prutting Custom Builders collaborated on this spectacular LEED certified 13,428 sf compound

Ellen Mosher Houlihan Lawrence

45 Binney Ln, Old Greenwich, CT 06870
/44
$6,750,000
- 5 Beds
- 9 Baths
- 9,974 Sq Ft
386 North St, Greenwich, CT 06830

This 9,974 sq. ft. estate, nestled in 2.3 acres of pristine, park-like grounds, epitomizes understated luxury. A handcrafted brick facade and hand-split shingle roof frame interiors adorned with rare materials and custom millwork. A grand, 2-story foyer leads to a formal area designed for refined entertaining. The luxury primary suite provides a serene retreat with a double private office and a

Stephen Archino Sotheby's International Realty

386 North St, Greenwich, CT 06830
/18
$11,000,000
- 8 Beds
- 7 Baths
- 8,751 Sq Ft
111 Byram Shore Rd, Greenwich, CT 06830

Experience panoramic views from this 1.5-acre waterfront estate. The views stretch across the Long Island Sound from Greenwich to Oyster Bay, allowing you to enjoy both sunrises and sunsets over the water- all in complete privacy from neighboring properties. This one-of-a-kind distinctive contemporary offers a truly unique blend of cutting-edge modern design and historic charm, complete with

Julie Church Houlihan Lawrence

111 Byram Shore Rd, Greenwich, CT 06830
/13
$1,995,000
- 4 Beds
- 1.5 Baths
33 Parsonage Rd, Greenwich, CT 06830

Beautiful property, on a desirable road, in the heart of Greenwich. Conveniently located close to schools and downtown. Move in, renovate, or build your dream home!*newly subdivided lot, assessment and taxes determined at time of sale.

Bryan Tunney Brown Harris Stevens CT, LLC

33 Parsonage Rd, Greenwich, CT 06830
/64
$43,000,000
- 6 Beds
- 11 Baths
- 11,500 Sq Ft
579 Indian Field Rd, Greenwich, CT 06830

This stunning 2.72 acre waterfront property in Mead Point has panoramic South and Easterly views across the Sound to Long Island, New York and to Tods Point and Riverside. Enjoy sunrises from almost every room in this custom-built stone and shingle colonial. The current owners intention to preserve the original house, was not possible, and they built new with the goal of retaining old world

Heather Platt Sotheby's International Realty

579 Indian Field Rd, Greenwich, CT 06830
/9
$11,900,000
- 6 Beds
- 9 Baths
- 9,836 Sq Ft
32 Pheasant Ln, Greenwich, CT 06830

Welcome to 32 Pheasant Lane, a stunning completely rebuilt and expanded modern Colonial on one of Greenwich's most coveted streets. This exceptional 6 bedroom, 7.2 bath home offers over 9800 square feet of luxurious finished living space on 4 levels. An expansive front porch invites you inside where you will discover an open, airy floor plan with 10ft ceilings and custom details. White oak floors

Maria Crowley Houlihan Lawrence

32 Pheasant Ln, Greenwich, CT 06830
/75
$13,750,000
- 6 Beds
- 8 Baths
- 9,418 Sq Ft
52 Carriglea Dr, Riverside, CT 06878

Experience unparalleled luxury in this extraordinary custom-built Riverside waterfront residence. Nestled on 1.45 acres with 9,418 square feet of living space, this exceptional home, designed by acclaimed architect Cormac Byrne, boasts a seamless open-concept layout that promotes effortless flow throughout. Soaring ceilings and expansive windows flood the interiors with natural light,

Stephen Archino Sotheby's International Realty

52 Carriglea Dr, Riverside, CT 06878
/20
$1,995,000
- 4 Beds
- 3 Baths
- 3,284 Sq Ft
297 Cognewaugh Rd, Cos Cob, CT 06807

Nestled within the serene beauty of Greenwich's sought-after Cos Cob community, this elegant property is set on two private, wooded acres. This refined 4-bedroom, 3-bathroom residence spans over 3,200 square feet of meticulously designed living space, perfect for the discerning buyer.Exquisite hardwood floors, sunlit interiors, and architectural details create an atmosphere of understated

Mark Pruner Compass Connecticut, LLC

297 Cognewaugh Rd, Cos Cob, CT 06807
/31
$8,950,000
- 6 Beds
- 5.5 Baths
- 5,040 Sq Ft
33 Meadow Wood Dr, Greenwich, CT 06830

In the gated Quarry Farm neighborhood of the enchanting Belle Haven Association with 24hr security, this property offers a unique opportunity to renovate or build new, 16,000+ sq ft waterfront home. Overlooking Byram Harbor and Long Island Sound, the current 6-bedroom house sits on 2.78 acres with a pool, adjacent to a 1.09-acre protected lot. Once a quarry and later acquired as part of the

Joseph Barbieri Sotheby's International Realty

33 Meadow Wood Dr, Greenwich, CT 06830
/23
$33,000,000
- 8 Beds
- 14 Baths
- 18,954 Sq Ft
555 Lake Ave, Greenwich, CT 06830

Overlooking 8+park-like acres, this majestic brick Georgian was transformed to blend top of the line appointments with a rich array of custom detailing. Crowned by a 3-story chandelier, the impressive reception hall with Wenge walnut parquetry floor opens to a formal Dining Room with fireplace and elegant Living Room with fireplace and custom bar. Distinguished two-story English mahogany library

Leslie McElwreath Sotheby's International Realty

555 Lake Ave, Greenwich, CT 06830
/53
$1,595,000 Open Sun 1PM - 3PM
- 4 Beds
- 2.5 Baths
- 3,827 Sq Ft
24 Rippowam Rd, Cos Cob, CT 06807

This newly and tastefully renovated sun-filled home offers a modern open-concept design with large windows and an abundance of natural light throughout. Featuring 4 spacious bedrooms, 2 1/2 baths and a beautiful brick fireplace with approximately 3,827 sq. ft. including the 1,033 sq. ft. (per Realty Plans) in the lower-level playroom, this truly turnkey home is ready for immediate occupancy.

Stephen Archino Sotheby's International Realty

24 Rippowam Rd, Cos Cob, CT 06807
/13
$4,350,000
- 5 Beds
- 4.5 Baths
- 3,858 Sq Ft
121 Round Hill Rd, Greenwich, CT 06831

This home was built with great bones and is now ready for a full renovation. OR, take it down and build new - see photos. Gorgeous 2.3 acres combine with a premier Round Hill Rd. address! The topography of 121 Round Hill Road offers uncommon long vistas from all floors with a unique blend of openness and privacy. Irrigated, manicured lawns, plantings, old stonewalls, and natural areas provide a

Sabine Schoenberg Primesites, Inc.

121 Round Hill Rd, Greenwich, CT 06831
/23
$4,350,000
- 6 Beds
- 4.5 Baths
- 4,958 Sq Ft
121 Round Hill Rd, Greenwich, CT 06831

Rare find - property on one of Greenwich' estate roads, Round Hill Rd. Oversized, private property, pool, stable, with a perfect blend of tranquil, manicured and natural landscapes. Enjoy your morning coffee gazing across beautiful east-facing rear vistas.Move right into this 5 bedroom 4 1/2 bath home, featuring upgrades like generator, irrigation, and largely new windows. Create your

Sabine Schoenberg PrimeSites, Inc.

121 Round Hill Rd, Greenwich, CT 06831
/49
$6,395,000
- 7 Beds
- 8 Baths
- 8,068 Sq Ft
2 Winding Ln, Greenwich, CT 06831

LOCATION, LOCATION LOCATION Set back on 2 private acres very close to town & landscaped to perfection, this exquisite property with over sized salt water pool, tennis court, children's playground, exquisite gardens & entertaining terraces offer today's buyers the perfect lifestyle. 8000+sq.ft. brick residence w/ new slate composite roof features 6 bdrms/6 bths, private office., lg light filled

Helene Barre Sotheby's International Realty

2 Winding Ln, Greenwich, CT 06831
/9
$4,295,000
- 4 Beds
- 2.5 Baths
- 3,650 Sq Ft
30 Milbank Ave, Greenwich, CT 06830

Welcome to The Robert Mead House - a magnificent 1854 Federal with a prominent downtown location in Greenwich. Sensitively preserved and extensively renovated over the past 18 years, this elegant building has immense character and charm. Large scale rooms, 12' ceiling height with beautiful mill work and tall windows throughout. With many different ways to enjoy this property please see

B.K. Bates Houlihan Lawrence

30 Milbank Ave, Greenwich, CT 06830
/40
$2,200,000
- 5 Beds
- 7.5 Baths
- 6,354 Sq Ft
25 Cogswell Ln, Stamford, CT 06902

This stunning 5-bedroom, 7.5 bath brick contemporary blends timeless elegance with modern sophistication. From the grand foyer, showcasing skylights and a limestone feature wall, to the living room with a quartzite fireplace and cathedral ceiling, every space in this home is designed for both beauty and function. The formal dining room, features a large bay window, offering picturesque views. The

Jim Caldarone William Pitt Sotheby's Int'l

25 Cogswell Ln, Stamford, CT 06902
/37
$4,275,000
- 5 Beds
- 7.5 Baths
- 6,725 Sq Ft
490 North St, Greenwich, CT 06830

Rare opportunity to own a 200 year old Barn on one mid-country acre, designed in the 70's by renowned architect Charles Gwathmey. Owners updated it to add additional bedrooms and seamlessly connect indoor and outdoor spaces offering year-round entertainment. Main entrance opens to an expansive 30 X 35' Great room filled with natural light, original beams, and impressive fireplace. A generous

Spencer Sodokoff Houlihan Lawrence

490 North St, Greenwich, CT 06830
/4
$540,000
- 3 Beds
- 3 Baths
- 1,372 Sq Ft
157 Cold Spring Rd, Stamford, CT 06905

Desirable neighborhood in Stamford! It is conveniently located near highways, public transportation, shopping, restaurants, etc. ESTATE SOLD AS IS, WHERE IS. Agents, please read the agent-only remarks section.

Katerina Hendrickson Coldwell Banker Realty

157 Cold Spring Rd, Stamford, CT 06905
/40
$4,995,000
- 5 Beds
- 5.5 Baths
- 4,286 Sq Ft
29 Lockwood Dr, Old Greenwich, CT 06870

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

Julie Lowe Houlihan Lawrence

29 Lockwood Dr, Old Greenwich, CT 06870
/33
$4,995,000
- 5 Beds
- 5.5 Baths
- 4,286 Sq Ft
29 Lockwood Dr, Old Greenwich, CT 06870

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

Julie Lowe Houlihan Lawrence

29 Lockwood Dr, Old Greenwich, CT 06870
/7
$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 over 10,000 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

Nina Frandson BHHS New England Properties

68 Dearfield Dr, Greenwich, CT 06831
/23
$475,000
- 3 Beds
- 1 Bath
- 912 Sq Ft
56 Bradley Place, Stamford, CT 06905

Attention Visionaries!! Small but Cozy 3 Bedroom & 1 Bath Ranch located in one of the best neighborhoods in Stamford. Lots of potential for adding square footage to this jewel. A MUST SEE !!

Juan Garcia Sunbelt Sales & Development

56 Bradley Place, Stamford, CT 06905
/41
$10,950,000
- 6 Beds
- 7.5 Baths
- 9,258 Sq Ft
142 Cedar Cliff Rd, Riverside, CT 06878

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

Alison Farn-Leigh BHHS New England Properties

142 Cedar Cliff Rd, Riverside, CT 06878
/39
$24,950,000
- 10 Beds
- 19 Baths
- 17,878 Sq Ft
97 Pecksland Rd, Greenwich, CT 06831

Truly unique 19 Acre estate in the heart of mid country! Prepared to be captivated by this custom built masterpiece of design and craftsmanship. Completed in 2009, and offered to the market for the first time since completion, 97 Pecksland has an unrivaled combination of lot size, quality and privacy. Enter through the grand gated entrance and dramatic driveway to the elevated main house on the

Robert Johnson Brown Harris Stevens CT, LLC

97 Pecksland Rd, Greenwich, CT 06831
/38
$5,995,000
- 6 Beds
- 7 Baths
- 6,673 Sq Ft
7 Jones Park Dr, Riverside, CT 06878

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

Ellen Mosher Houlihan Lawrence

7 Jones Park Dr, Riverside, CT 06878
/6
$750,000
- 3 Beds
- 2 Baths
- 1,007 Sq Ft
57 Prospect St, Greenwich, CT 06830

Rach Style Home in great location .Don't miss this opportunity to own a wonderful ranch house close to I-95

Iryna Rosales Smart Realty Services Corp

57 Prospect St, Greenwich, CT 06830
/42
$8,950,000
- 10 Beds
- 9 Baths
- 9,483 Sq Ft
14 Meadow Dr, Greenwich, CT 06831

DISCOVER BREEZEMORE Experience the rare opportunity to own a piece of history with the stunning Breezemore estate located in Greenwich, Connecticut. Built in 1909, this magnificent property offers 10,000 square feet of architectural splendor, old-world charm, and modern conveniences. Set high on 3.2 private, park-like acres within close distance of downtown Greenwich, this property stands

Ryan Hoffman Houlihan Lawrence

14 Meadow Dr, Greenwich, CT 06831

Showing Results 81 - 120, Page 3 of 4

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In Old Greenwich, there are currently 134 houses for sale, offering an array of options for potential buyers. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Old Greenwich, CT and find the perfect place to call home.

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