Weston, CT Homes for Sale with Acreage

Set on 5+ private acres at the end of a coveted cul-de-sac, this distinctive family compound is minutes to town and top-rated schools. Classic New England architecture opens to a striking, loft-inspired interior defined by soaring three-story ceilings, hand-hewn antique beams from the late 1800s, wide-plank floors, and walls of glass that fill the home with natural light. Generous living spaces

Michelle Genovesi William Raveis Real Estate

Set privately in Weston, this extraordinary home is an early masterpiece by Michael Greenberg, featuring a meticulously relocated Vermont barn, rebuilt with exceptional care and craftsmanship. Rich in character, the residence blends rustic authenticity with refined, modern updates. The stunning great room is anchored by a dramatic three-story fieldstone fireplace, while the first-floor primary

Georgia Wasserman Coldwell Banker Realty

A four-season retreat-where open lawns, a large GUNITE POOL ready for you to swim before Memorial Day, and the surrounding landscape create a sense of quiet luxury. Set along the Saugatuck River on a quiet private Lower Weston Cul de Sac, this architecturally distinctive contemporary is privately sited on 2.49 acres, offering scale, light, and direct river access in one of Weston's most desirable

Hope Klein The Riverside Realty Group

Experience dramatic, modern living in this grand home with a glorious gunite pool & exceptional architectural appeal. Custom-designed, the quality of this residence is readily apparent as you approach from the centrally-located, multi-million dollar neighborhood of fine homes. The stone front, Belgium block-lined drive and specimen landscaping greet you, leading to the soaring two-story foyer.

Barbara Bross Coldwell Banker Realty

Set on three private acres of serene woodland along the banks of the Saugatuck River, this extraordinary Riverfront Retreat offers a rare opportunity to live immersed in nature in a modern masterpiece. Creating a seamless connection between the stunning interiors and the tranquil beauty of the surrounding landscape, experience breathtaking river views from the rooftop deck with succulent gardens,

Laurie Crouse Coldwell Banker Realty

Striking contemporary sanctuary set on 2.4 private acres along one of Lower Weston's most coveted cul-de-sacs--where sophistication meets serenity. Dramatic atrium entry with soaring ceilings and skylights introduces a home defined by light, volume, and architectural distinction. Walls of glass and multiple French doors dissolve the boundary between indoors and out, creating a seamless connection

Monica Kass BHHS New England Properties

Welcome to 14 Langner Lane, a uniquely charming stone residence set on 2.35 beautifully landcaped acres of lush, private property in the coveted town of Weston. Offering approximately 3,880 square feet of living space, this home beautifully blends architectural character with exceptional space, making it perfect for families seeking privacy and room to roam. Fall in love with 14 Langner's

Scott Palma William Raveis Real Estate

Set on over two private acres along the Wilton/Weston border, this architecturally distinct Contemporary offers a compelling blend of design, privacy & setting. Ideally positioned in southern Wilton, the home offers rare convenience-just minutes to Wilton Center, Weston, Westport & Georgetown. A circular drive leads to the home, where striking vertical siding and thoughtfully designed grounds

Matthew Nuzie RE/MAX Right Choice

Tucked away at the end of a long private drive, this exceptional property offers rare privacy just mins from everything Westport has to offer. Set on 2.1 acres, 3 Cedar Pond Rd is a true hidden oasis in the heart of town. Custom-built by noted architect George White as a 'replica' Colonial, the home reflects the timeless character of early CT architecture & was recognized by the Westport Historic

Shannon Manning The Riverside Realty Group

Rock Ledge, a private estate in Weston, is set on nearly five acres surrounded by protected land at the end of a cherry-tree-lined private drive. A reimagined Tudor Revival that blends historic character with modern living. Originally built in 1918, the property was once the residence of Godspell author John-Michael Tebelak. It has evolved into a compound of a brick mansion, pool house with

John Schiaroli Coldwell Banker Realty

Welcome to 18 Cartbridge Road! This beautifully stylish expanded Cape is flooded with natural light, it's warm & inviting throughout with over sized rooms. This home is located in lower Weston situated on an acre with beautiful gardens. The formal living room has a fireplace, hardwood floors, & it leads to a playroom/office. Just off of the living room is the formal dining room. The large family

Stacy Haggerty William Raveis Real Estate

This is very special. $7,500 per month income! INVESTOR'S DREAM !! AN AMAZING OPPORTUNITY IN LOWER WESTON-DIRECT SAUGATUCK RIVER FRONT VIEWS-Beautiful home with separate living spaces featuring living rooms, family rooms, dining areas, newer kitchens & baths, wraparound decks with serene river views and so much more. Beautiful hardwood floors throughout, updated bathrooms and kitchens, newly

Dagny Eason Dagny's Real Estate

Beautiful 5-bedroom 3 and half bath Colonial set on 2 private acres featuring hardwood floors throughout, a whole-house automatic standby generator, completely refinished hardwood floors upstairs, and fresh interior paint throughout. The open floor plan seamlessly connects the eat-in kitchen and family room, creating the perfect space for everyday living and entertaining. The spacious family room

Karen Magee Brown Harris Stevens

NEW...Stunning transitional 5-bedroom estate blending classic curb appeal with a clean, modern interior - beautifully sited on 2.35 private acres. This immaculate five-bedroom home offers five ensuite bedrooms (including a luxurious primary suite), exceptional finishes and thoughtful details throughout:Thermador appliances, high-end fixtures, and gorgeous White Oak floors and handrails that run

Tom Kelley Coldwell Banker Realty

Set on 3 private acres of riverfront property, this classic 1700's colonial is timeless, composed, and rooted in Weston's earliest history. Beyond the elegant facade, a residence unfolds - expansive, impeccably crafted, and quietly refined. Rebuilt to the studs and thoughtfully reimagined for today, it lives fully in the present while honoring its past. The graceful floor plan balances generous

Susan Seath Compass Connecticut, LLC

Find Your Place on Glory Road. Step inside this charming contemporary ranch with a twist, tucked on a quiet cul-de-sac in Weston's sought-after Georgetown neighborhood. With a flat backyard, countless updates, and spaces designed for both connection and retreat, this home blends timeless character with modern comfort. The sun-filled main level opens with a welcoming living & dining area, anchored

Erica Acheychek Compass Connecticut, LLC

Exceptional opportunity in a prime Lower Weston location directly bordering Westport - just minutes to both Weston and Westport town centers, award-winning schools, shopping, dining, trains and commuting routes. Privately set on a beautiful 2-acre lot on a quiet country lane, this property offers endless potential for buyers with vision. Whether you choose to renovate, customize, expand, or build

Christine Oleynick Keller Williams Realty

Highest & Best Offers due 5PM TUESDAY, 4/14.Welcome to this sophisticated country Cape blending modern living with charm in Weston's Georgetown area. White picket fences & stepping stones through an arbor welcome you to the front porch of this beautiful home! Set at the end of a quiet cul-de-sac on a level acre w/inviting circular driveway, the open floor plan creates comfortable flow for

Dianne DeWitt Berkshire Hathaway NE Prop.

Exceptional 5-BR stone home blending contemporary design w natural tranquility sits atop 2 private acres in Weston. Expertly engineered & beautifully constructed, this freshly painted home welcomes you through a dramatic 2-story foyer into a sun-filled living room with floor-to-ceiling windows, sweeping woodland views, and a custom 2-sided fireplace. Open chef's kitchen features granite

Elaine Schanzenbach William Raveis Real Estate

Prepared to be awe-struck! This renovated/updated mid-century modern home is a naturalist's dream with walls of glass that allow for light filled spaces & a calming vibe. A two-sided field stone fireplace anchors the living spaces including the stunningly designed kitchen featuring a 10x6 quartz topped center island & new windows overlooking the magical zen courtyard/garden w/ flowering trees and

Carrie Shea Camelot Real Estate

Welcome to 24 N Calvin Rd, an exceptional residence set in the prestigious enclave of Weston, where timeless elegance meets serene New England beauty. Perfectly positioned on a private, picturesque setting, this distinguished home offers a rare combination of sophistication, comfort, and refined living. Thoughtfully designed with attention to detail, the home features expansive, light-filled

Irsannia Gallardo eRealty Advisors, Inc.

In the heart of a neighborhood known for fine estates and just moments from the campus of award-winning schools, this distinguished 2.5 +/- acre property elevates your lifestyle with refined craftsmanship and effortless luxury. A grand foyer with a graceful floating staircase introduces interiors defined by exquisite walnut floors, incredible millwork, and architectural moments to savor at every

Alex Chingas Coldwell Banker Realty

Eight minutes from downtown Westport, escape to 11 Judges Hollow-a 1930's rustic hunting cabin on 1.6 private wooded acres at the end of a long secluded driveway. A one of a kind private in holding completely surrounded by the 180 acre Brett Woods Conservation Area, this rare property offers ultimate privacy with protected open space as your permanent neighbor. Judges Hollow is nestled within

Lisa Hartmann William Pitt Sotheby's Int'l

Reminiscent of an European Estate this 4420 square-foot home features, four bedrooms, two full bathrooms and two half bathrooms on an open acre of land. It's extensive outdoor patio and entertainment areas wrap around the rear of the property, a cobblestone lined driveway, and specimen landscaping are all situated on a cul-de-sac in an easy to get to everything location. The gourmet kitchen

Peter Hastings Hastings Real Estate

Rare 2.25-acre riverfront opportunity on the Fairfield/Westport line. This exceptional 538-foot deep lot offers 158 feet of frontage along the Aspetuck River, creating a private, scenic setting with significant upside. A unique feature is the ability to site a new home further back from Westport Turnpike, maximizing privacy and long-term value. The existing 3-bedroom, 2-bath ranch offers

Chip Parrish Keller Williams Realty

Completely reimagined from top to bottom, this beautifully renovated Redding residence offers the comfort, efficiency, and peace of mind of a newly built home. Every major system and finish has been replaced, including a brand-new roof, siding, windows, doors, plumbing, electrical, and a new central A/C and heating system, ensuring modern performance and long-term reliability. Inside, the home

Thomas Casey Live Real Estate LLC