Old Greenwich, CT Homes for Sale with Acreage

Welcome to ''Park Hill'', a reimagined 1923 English Manor in a Prestigious Private Association. Thoughtfully refreshed for modern living while preserving the architectural character that makes it timeless. Set on 1.81 private, park-like acres, this 7,632 sq. ft. manor blends historic charm with contemporary luxury in a way few properties can. 1923 English Tudor Revival with 2025 updates. Rare

Danielle Claroni Sotheby's International Realty

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

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

Perched high on a scenic knoll off a private road and set on nearly 4 acres of manicured grounds, this timeless estate is a rare opportunity to own one of Westover's most distinguished properties. Showcasing an 8,543 sq ft Georgian brick manor, built in 1989 with masterful attention to quality and detail, this renovated home offers a luxurious lifestyle with warmth and sophistication throughout.

Anthony Ardino William Raveis Real Estate

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

A timeless Georgian residence, 6 bedrooms, 6.2 baths, ideally situated on 2 acres in one of Greenwich's most coveted locations. This home, bathed in natural light, is defined by classic symmetry and scaled proportions. Privately positioned at the end of a cul-de-sac, with heated pool and spa, it enjoys an exceptional sense of openness while remaining quietly secluded. Upstairs, a serene primary

Melinda Relyea Houlihan Lawrence

A rare offering of refined luxury and meticulous craftsmanship, 108 Husted Lane is a stunning estate that has been extensively renovated and enhanced, blending timeless architecture with modern sophistication. Set behind stone walls and surrounded by mature landscaping, this exceptional residence offers unparalleled privacy, scale, and comfort. The home has undergone significant, high-caliber

Joy Kim Metalios Houlihan Lawrence

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

With breathtaking views of Long Island Sound, this custom-built Mediterranean-style home is nestled in an exclusive gated community known as Quarry Farm in Belle Haven. Featuring a terracotta-tiled roof, this luxurious home boasts 6-bedrooms and 6.3 baths on 4.7 acres of land. The central courtyard, which serves as the heart of the home, is surrounded by common living areas with extra-height

Jennifer Ho Douglas Elliman of Connecticut

Ideally located on a picture-perfect cul-de sac, this Shingle Style house has had just one owner since it was built in 2005. A well-conceived 9,295 +/-SF floor plan comprises six bedrooms, seven full bathrooms and two powder rooms, plus five fireplaces. High ceilings invite an abundance of light, while exquisite millwork, rich hardwood floors and a desirable layout highlight the appealing

Leslie McElwreath Sotheby's International Realty

Nestled within the prestigious Belle Haven, Fairholme Estate is a magnificent English Manor that exudes timeless elegance and grandeur. Set on 2.74 beautifully landscaped acres, this seven-bedroom masterpiece features a spectacular pool, gracious wraparound porch, formal gardens, and expansive lawns, complemented by a charming coachman's cottage. Meticulously preserved to honor its historic

Joanne Mancuso Houlihan Lawrence

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

Experience the ease of elevated mid-country living in this extraordinary, sundrenched six bedroom Colonial on two manicured acres showcasing fresh new landscaping with pool, patio and pergola ideally located just three miles from town. Built in 2023 with many bespoke features which enhance the 10,800 sq. ft. interior offering 6'' white oak flooring, custom cabinetry and an abundance of windows

Michele Tesei Houlihan Lawrence

Peace and tranquility amid 7.37 lush acres, just minutes from Downtown Greenwich: this is Harkaway Farm, a distinguished Georgian Colonial estate set behind stately stone pillars and impressive gates. A meandering drive carries you over a stone bridge fording a gentle stream, to the recently transformed home. Built exceptional craftsmanship the facade of the stately manner was preserved and

Francine Ehrlich Sotheby's International Realty

Exquisite six-bedroom stone manor, executed to the highest standards, and sited atop a majestic knoll on 2.97 picturesque acres in the heart of Mid-Country Greenwich. Chic, sophisticated interiors by Amy Hirsch unfold across three levels of light-filled living space, highlighted by soaring ceilings, oversized custom windows, and every modern amenity. An elegant double-height entry hall with

Leslie McElwreath Sotheby's International Realty

Set on nearly 2 acres in one of Riverside's most coveted waterfront enclaves, this elegant colonial offers refined living and a sense of privacy and tranquility. A new cedar roof 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

Remy Cook Corcoran Centric Realty LLC

On sought-after Belle Haven peninsula near town, this 2008 expanded 5 bed, 3.2 bath home boasts breathtaking Greenwich Harbor views. Perfectly designed for harborside living & entertaining, the sunlit gourmet chef's kitchen & great room boast an expansive island, custom cabinetry and a wall of windows overlooking harbor & park. The spacious living room, complete with wood burning fireplace &

Meg McAuley Kaicher Coldwell Banker Realty

Dramatic views of Long Island Sound extend from this spectacular 1.50-acre property with 185 ft of direct water frontage, an 80-ft dock, a sandy boat launch and a 528 sq.ft. antique cottage. Walls of glass in the current 5-bedroom residence open to a spectacular deck with pool and panoramic views. Once part of the 43-acre Edgar Marston estate, the property includes c.1885 Queen Anne-style cottage

Joseph Barbieri Sotheby's International Realty

Welcome to 420 North Street - Superbly renovated in 2024, this centrally located, move in ready home has it all. Excellent layout throughout with an open feel and great light. Oversized kitchen with excellent millwork and appliances plus informal dining area all overlooking a stunning pool and spa. Open plan family area and formal living room with bar. Generous primary bedroom suite has a

Robert Johnson Brown Harris Stevens CT, LLC

Tucked away down a quiet mid-country lane, surrounded by pretty woodlands, is this modern styled one level home with 3 bedroom septic. Large open reception hall, large living room with fireplace, high ceilings, study/office area, and large formal south-facing dining room with oversized windows that overlook the front yard and lovely mature trees. A step down from the dining room through French

Edward Mortimer Sotheby's International Realty

Ultra-stylish 2024 custom-built Contemporary from visionary developer SBP Homes graces nearly 5.5 private, gated acres very close to town with pool, spa, two-bedroom pool house, porches, outdoor kitchen, fireplace and tennis court designed for optimum indoor/outdoor entertaining and relaxed living. Luxurious details elevate the 11,000+ sq. Interior with Bulthaup kitchen, living room bar; walls of

James Hoffman Houlihan Lawrence

Build your legacy in one of Greenwich, CT's most sought-after downtown gated communities. Approved plans and ready to break ground with local Award winning developer, Greenwich Custom Homes. A magnificent estate will be built with precision and finished with elegance, continuing to raise the bar for the finest living in Greenwich CT. This Georgian Colonial, with LI Sound waterfront access, blends

Brian Milton Compass Connecticut, LLC

Timeless in its design, this architecturally crafted contemporary home blends soaring vaulted ceilings with panoramic views, creating a seamless connection to the outdoors. Thoughtfully sited on 2.32 peaceful and private acres, it captures natural light throughout the seasons while remaining just minutes from every convenience.The open-concept layout is ideal for both grand entertaining and

Paula Waldman BHHS New England Properties

A rare waterfront estate of true scale and presence, this reimagined coastal masterpiece commands 1.6 acres on the Long Island Sound with sweeping, unobstructed horizon views. Rebuilt from the foundation up, the home delivers level beachfront living with powerful architectural lines, floor-to-ceiling glass, and a seamless connection to the water at every turn. The approach opens to a 19-foot

Jesse Marinak Serhant Connecticut LLC

Stunning 6-bedroom Colonial in Mid-Country currently underway (Summer '26 completion). Designed to impress by the renowned Alex Kaali-Nagy Architect AIA with a traditional exterior look, quintessential Greenwich, but a transitional interior with 4 finished levels and thoughtful design touches throughout, including extensive millwork. Exceptional primary suite with walk-in dressing rooms, plus 5

Amanda Miller Houlihan Lawrence

Set along a private lane off Stanwich Road, this exquisitely maintained and recently enhanced six-bedroom, six full and one half bathroom Shingle-Style residence is bathed in natural light and embraced by acres of conservation land, ensuring exceptional privacy and tranquility. Designed with high ceilings and a thoughtful open layout, the home blends timeless architectural elegance with

Leslie McElwreath Sotheby's International Realty

THIS NEW CONSTRUCTION CHECKS ALL THE BOXES OF A MODERN FARMHOUSE DESIGN. THE OPEN CONCEPT FLOORPLAN ALLOWS FOR INDOOR/OUTDOOR ENTERTAINING. THE ATTENTION TO DETAIL & HIGHEND FINISHES ARE APPARENT AS SOON AS YOU ENTER THIS SPECIAL PROPERTY. LOCATED IN A HIGHLY SOUGHTAFTER NEIGHBORHOOD OF REVONAH WOODS. THE MAIN LEVEL IS PERFECTLY SUITED FOR GRAND ENTERTAINING. THE GENEROUS SIZED ROOMS WITH

Barbara Webski William Pitt Sotheby's Int'l

A winding drive gently rises through majestic trees to this architect designed handsome Dutch shingle home built in 2001. Set on a hilltop plateau in the heart of Mid-Country, the property is spectacular and could easily support a large addition or a new build with substantial square footage available on the over 2 acre lot. The warmth and character of this 4,000 sq ft, 4 bedroom, 3.5 bath home

Martha Jeffrey Sotheby's International Realty

DEER PARK WOODSIDE: This distinguished 1930's brick Georgian is set on a serene, oversized lot within Deer Park Association, embodying the timeless architectural presence of a classic pre-war brick manor. Originally designed as an elegant six-bedroom, six-bath residence, the home offers an exciting opportunity to be reimagined for its next chapter. The exceptional grounds unfold across expansive,

Leslie McElwreath Sotheby's International Realty

Perched on the top floor of historic Greenwich Lodge, this spacious one-bedroom blends classic character with crisp updates. Soaring 18-foot vaulted ceilings complement hardwood floors and western-facing windows that flood the home with light and frame unobstructed sunset and NYC skyline views. An eat-in kitchen offers generous room for dining and meal prep, and the smart layout supports both

Frank Schiavone Compass Connecticut, LLC