Old Greenwich, CT Homes for Sale with Acreage

LUMEN HOUSESet behind a private bridge on four gated acres of west-facing land, Lumen House is a 10,000+ square foot modern estate that transcends the ordinary. Conceived through a rare collaboration between Boutique Project Development, Atkins Construction Group, and the celebrated Vakota Architecture, this six-bedroom, nine-and-a-half-bath residence stands as one of Backcountry Greenwich's

Jeffrey Jackson Corcoran Centric Realty LLC

THE GIVING HOUSE. For 39 years, 69 Brookhollow has given this family something that can't be measured in square feet: a home that adapted beautifully as life changed around them. Set high above the street on a cul-de-sac in sought-after Westover, this ranch offers 2,714 finished square feet on one level with a smart, functional layout. The giving begins at the heart of the home-the oversized

Lori Elkins William Raveis Real Estate

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

An extraordinary opportunity to acquire a waterfront residence within the exclusive & highly coveted Belle Haven Association - at an unusually low ''cost of entry'' point. One of just eight residences in historic Quarry Farms - which has its own gated entrance, this gut renovated 3-bedroom. 3.5 bathroom home is privately set on 1.2 acres with 220' of direct Long Island Sound frontage. Unique

Kevin Sneddon Compass Connecticut, LLC

Set on two picturesque acres in a premier Greenwich estate neighborhood, this exceptional property offers the perfect canvas to design and build your ultimate dream home. Surrounded by natural beauty with a serene, park-like setting, it provides both privacy and prestige. Ideally located just minutes from downtown, Greenwich Avenue, top-rated schools, and the Metro-North train station, offering

Alison Farn-Leigh Brown Harris Stevens CT, LLC

Sport lovers dream - Set on a quiet cul-de-sac within Sherwood Farms, this custom-built 2013 residence offers four finished levels of thoughtfully designed living space paired with exceptional recreational and lifestyle amenities. High ceilings, abundant natural light and seamless flow define the main level, where formal living and dining rooms connect effortlessly to an expansive open-concept

Amanda Bates Houlihan Lawrence Inc.

Tucked within the secluded Indian Point Association, this 1.55-acre waterfront sanctuary in coveted Riverside invites you to imagine the lifestyle that you have always wanted. From its sweeping southwestern vantage point, the property opens to mesmerizing views of Long Island Sound-a living canvas that shifts with every season, every tide, every change of light. A charming 1949 built house sits

Patte Nusbaum Sotheby's International Realty

Sport Lovers Dream - Set at end of a quiet cul-de-sac on Stillman Lane, this custom-built 2013 residence offers 4 finished levels of thoughtfully designed living space on 1.2 level acres w putting green. High ceilings, abundant natural light and seamless flow define the main level, where formal living and dining rooms connect effortlessly to an expansive open-concept kitchen and family room with

Amanda Bates Houlihan Lawrence

A Rare Convergence of Beauty, Vision and Readiness to Build Your Dream Home in Greenwich's Golden Triangle. This 2.3-acre property/land is for a discerning buyer who values beauty, time and predictability. Shovel-Ready with custom architectural work by award-winning Saniee Architects. Full municipal approvals in place for your 10,000 square-foot residence -- eliminating a year or more typically

Sabine Schoenberg PrimeSites, Inc.

Privately set on more than 6 extraordinary acres within the prestigious Khakum Wood Association, this award-winning estate offers distinction, privacy, and architectural excellence in an A+ location. Clad in limestone, fieldstone, and stucco and crowned by a graduated slate roof, the residence is defined by timeless elegance and exceptional quality. Bright interiors feature soaring ceilings,

Deborah Ward Sotheby's International Realty

Set on over an acre at the end of a quiet cul-de-sac within the private Lia Fail Association in Greenwich, CT (Cos Cob), this exceptional stone and clapboard Colonial masterfully blends timeless style with resort-like amenities across approximately 6,300 square feet of beautifully designed living space. The property offers ultimate privacy and an expansive yard designed for grand-scale

Rachel Overton BHHS New England Properties

This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering one acre of east facing views that can be enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned by Christopher Plummer of The Sound of Music, the current owners have meticulously renovated and restored

Shelly Tretter Lynch Compass Connecticut, LLC

Surrounded by the Long Island Sound on three sides, this extraordinary waterfront compound has defined the southern tip of Shippan Point for more than a century. Set on a private peninsula, it offers the rare privilege of watching the sun rise over the Sound and set back into the water with the Manhattan skyline shimmering in the distance.Designed by Hunt & Hunt Architects and completed in

Leslie McElwreath Sotheby's International Realty

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

Light-filled spaces, an open layout, and a seamless connection to the outdoors define this unique contemporary home on one private acre in Stamford. The main level was designed for everyday living and entertaining, with the kitchen flowing into a spacious great room that combines the living and dining areas around a wood-burning fireplace. Large windows bring in natural light throughout the day,

George Herchenroether GLG Realty Group, LLC

GREAT INVESTMENT OPPORTUNITY-Bellavista is a 16,000+sf estate designed by architect Anthony Minichetti, comprised of 9 bedrooms, 9 full baths, and 4 half baths, set on 2.93 private elevated acres within Greenwich's elite Golden Triangle. Commanding panoramic views over one of Greenwich's historic Country Club golf courses, plus Long Island Sound views from the 2nd and 3rd floors, A truly

Jill Kelly Sotheby's International Realty

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

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

A home of enduring beauty and remarkable provenance, Roxbury Rose is a rare offering that celebrates the craftsmanship and character of a bygone era. Believed to be one of Westover's original farmhouses, this distinguished 1860 Greek Revival Colonial has been thoughtfully preserved while embracing the comforts of modern living. Rich in authentic architectural detail, the residence is defined by

Teodoro Sibilia Keller Williams Prestige Prop.

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

Serene & Private Escape. With a trending modern sensibility, this light-filled residence showcases oversized windows and doors, and soaring ceilings throughout the home. Designed for one-level living, the layout features 3 bedrooms, 2.5 baths with more potential, and a generous primary overlooking tranquil woodland views. A fireplace anchors the living room, while a sun-drenched south-facing

Edward Mortimer Sotheby's International Realty

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

LOCATION ,LOCATION, LOCATION! Striking, sophisticated, & contemporary w/a true WOW factor. This exceptional residence is tucked within the celebrated Golden Triangle, surrounded by some of Greenwich's most prominent estates. A rare blend of timeless modern sensibility, the home showcases stunning interiors, refined elegance, & impeccable craftmanship. Designed for today's lifestyle, the layout

Janet Milligan Sotheby's International Realty

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.

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

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

Nestled at the end of one of Westover's most sought after cul-de-sacs, this exceptional five bedroom residence offers the perfect blend of privacy, elegance, and convenience. Ideally positioned on the Greenwich border, you'll enjoy quick access to downtown Stamford, Metro North, and vibrant downtown Greenwich, while returning home to a peaceful, secluded setting surrounded by nature. Designed

Nancy Rondano Keller Williams Prestige Prop.

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

One level living at its best! A gated drive introduces this beautifully appointed stone residence, gracefully set on over two exquisitely landscaped Mid-Country acres. Light-filled interiors offer a rare combination of scale and comfort, and are defined by dramatic ceiling heights, expansive windows, and beautifully proportioned spaces. A generous entry flows to the formal dining and living

Leslie McElwreath Sotheby's International Realty

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

Perched in timeless elegance atop an expansive 2.91-acre gated peninsula, with best-in-class views of the Manhattan skyline and the shimmering Long Island Sound, Cedar Cliff is a Mediterranean villa of unrivaled pedigree and commanding presence. Privately situated along a secluded road within Riverside's prestigious Indian Head Association, this storied property occupies the historic grounds of

Leslie McElwreath Sotheby's International Realty

Modern Sophistication Meets Suburban Serenity in Westover - Tucked away on a tranquil cul-de-sac, this recently built architectural gem offers a masterclass in modern living, blending refined elegance with the vibrant energy of nearby downtown Stamford. The residence unfolds through a dramatic two-story foyer into a sun-drenched, open-concept sanctuary, where a chef-inspired kitchen-adorned with

Jaime Sneddon William Pitt Sotheby's Int'l

Set on 1.5 picturesque acres in Stamford's desirable Westover neighborhood, this sprawling ranch offers comfortable living surrounded by a pond, and mature perennial gardens. The main level features a spacious eat-in kitchen with stainless steel appliances, a formal dining room, a private office, and a light-filled living room with hardwood floors, a fireplace with a custom mantel, and a large

Chris Carozza RE/MAX Right Choice

Rare 3.75-Acre Builder Opportunity on W Hill Road Exceptional opportunity to own 3.75 private acres in one of the area's most prestigious and sought-after locations-W Hill Road. This unique property features an existing 4,400 sq ft main residence plus a separate 900 sq ft cottage, offering endless possibilities for builders, investors, or end-users seeking a private estate setting. The current

Antonio LaRocca The LaRocca Group

SUMMER FUN BEGINS HERE! An extraordinary newly constructed residence in the heart of Greenwich,7 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

Leslie McElwreath Sotheby's International Realty