Homes for Sale near Weston High School

This Charming 3-bedroom, 2-bath Colonial is ideally located close to downtown Weston! Featuring a spacious living room, large kitchen with granite countertops, and a formal dining room with a full bath and separate laundry room. The second level has two bedrooms, a shared bathroom and office area. The expansive primary bedroom is located on the 3rd level with full-sized windows and its own

Jared Randall Redfin Corporation

Discover a stunning custom-crafted luxury home, complete with a separate one-bedroom guest pool house, that stands as an architecturally significant estate designed to be cherished. Nestled on meticulously landscaped grounds with picturesque views of Pawtucket Valley Country Club, this grand colonial residence offers every amenity for a refined lifestyle. As you enter the soaring foyer, you are

Anissa Paolillo Redfin Corporation

This meticulous home was rebuilt and expanded in 2015, refinished floors and fresh paint in 2025, and is located on 2 sunny acres in lower Weston. Professionally crafted stone pillars, walls, and patios, and a sweeping circular driveway create exceptional curb appeal in a serene cul-de-sac setting. The renovation and expansion transformed the property-adding a charming front porch and a stunning

Mary Palmieri Gai Berkshire Hathaway NE Prop.

Welcome to this beautifully maintained 4BR colonial nestled in one of Weston's most desirable neighborhoods. Set on 2.35 level acres, this inviting home offers a perfect blend of classic charm & modern updates. The heart of the home is the renovated kitchen featuring white cabinetry, granite countertops, a large center island, dining area, & newer appliances. The first floor offers exceptional

Kathleen O'Connell Coldwell Banker Realty

Secluded Riverfront Estate: A Masterpiece of Luxury, Tranquility, and Investment Value Set along a pristine riverfront, this extraordinary estate blends unparalleled natural beauty with world-class craftsmanship. Offering a private nature preserve outside your door, you'll enjoy kayaking, fishing, and luxuries few can experience. This property isn't just an investment in real estate; it's a

Betty Stroll William Raveis Real Estate

Located in Lower Lower Weston and in move-in condition for summertime enjoyment and be ready for school. This beautiful 4-bedroom, 2 full and 2 half-bath Colonial is set on one of the best cul-de-sacs in town. Nestled on a serene and picturesque 2-acre lot, the home offers both privacy and convenience-just minutes from town, award-winning schools, and the Westport train station. Step inside to

Hope Klein The Riverside Realty Group

Welcome to your own private oasis at 30 Soundview Farm, sequestered on over 2 acres of breathtaking landscape; a Michael Greenberg original. This remarkable home is nestled at the end of a quaint cul-de-sac, overlooking the 3rd hole of the Aspetuck Valley Country Club; conveniently located in lower Weston, bordering Easton & Fairfield. The grounds begin this home's story as a picturesque

Julie Vanderblue Higgins Group Real Estate

This modern farmhouse offers year-round comfort and effortless entertaining! Set at the end of a quiet cul-de-sac, the 7,760 sq ft home borders the 37 acres of trails of the Grace Robinson Nature Sanctuary - yet is just minutes to Weston's award-winning schools and village center. Inside, the home is light-filled and inviting, featuring a flexible layout and spacious rooms. A formal living room

Cyd Hamer William Pitt Sotheby's Int'l

29 Bradley Road seamlessly blends timeless New England charm with modern-day comforts, set against the backdrop of one of Connecticut's most picturesque (1000+acre) nature preserves. This "Quintessential Country Home"-features a professionally landscaped & sprawling backyard, adorned with specimen plantings that provide year-round beauty & curb appeal. Inside layout offers an effortless

Vickie Kelley Camelot Real Estate

Tucked on a peaceful cul-de-sac in prime lower Weston, this contemporary gem is a rare find. Set on beautifully landscaped grounds with a sparkling pool, this 4-bedroom, 2.5-bath home offers an airy, sun-filled layout perfect for modern living. The spacious living room features a vaulted ceiling, wood-burning fireplace, wet bar, and sliders to the deck, creating an ideal flow for indoor-outdoor

Dee Cohen Compass Connecticut, LLC

This stunning Colonial sits proudly on a beautifully landscaped 2-acre lot on the corner of Coley Drive, just over the Westport line in Lower Weston. Enjoy the best of both towns with easy access to the Merritt, train, Longshore, The Y and Compo beach. Perfectly situated for walking and biking on neighboring streets, the property features a heated in-ground pool, gorgeous bluestone patio and

Julie Vanderblue Higgins Group Real Estate

Luxury & Convenience: Stunning Home Just Minutes from Merritt Parkway! Welcome to 9 Blue Spruce Circle-a masterfully designed, meticulously maintained 5-bedroom, 41/2-bath colonial, nestled on 2.03 private acres in picturesque Weston. Tucked away on a coveted cul-de-sac, this home seamlessly blends tranquility and convenience, with a charming pathway leading directly to Morehouse Farm Park.

Maria Tziolis William Pitt Sotheby's Int'l

New construction for SALE or RENT. Dont miss the opportunity to be the first to occupy this newly erected Modern Farmhouse sited on 1.3 acres of picturesque property just steps away to the Katharine Ordway Nature Preserve. Flooded with natural light and southern exposure, this home offers many special features including hardwood floors, 7 1/2 foot kitchen island with Quartz countertops, stainless

Carrie Shea Camelot Real Estate

Idyllic riverfront property in Lower Weston - a builder's dream with both main house and barn transformations. Nestled along the serene Saugatuck River on a private lane, 17 Huckleberry Lane presents a rare and exciting opportunity to craft something truly extraordinary. This 2.12-acre riverfront property boasts over 350 feet of direct waterfront, highlighted by a rocky break in the river that

Jay Cannone William Raveis Real Estate

Bringing the Indoors and Outdoors Together with Mid-Century Rustic Elegance... Designed by renowned Broadway scenic designer Ralph Alswang-whose legacy includes nearly 100 productions and iconic venues such as the George Gershwin Theatre-this extraordinary Weston home reflects his theatrical eye for light, space, and natural beauty. Alswang, who also designed a handful of homes for notable

Vickie Kelley Camelot Real Estate

Welcome to this timeless Colonial, where comfort, functionality, and style come together seamlessly. The main level is thoughtfully designed for everyday living and easy entertaining. The updated kitchen overlooks a peaceful backyard and features an inviting eat-in area with a cozy wood-burning fireplace. Just off the kitchen, the formal dining room offers a warm, elegant space for hosting. A

Georgia Wasserman Coldwell Banker Realty

Enjoy an authentic resort vibe, all just minutes from Westport. Experience unparalleled light and distant views in this luxurious haven. A stunning blend of elegance and modern comfort set in a tranquil environment. This is a true oasis! The current owner has updated three of the four bathrooms, installed numerous new appliances, constructed a new fire pit, installed a new pool heater, and

Marion Filley Compass Connecticut, LLC

Discover exceptional living at this distinguished 5-bedroom, 3-bathroom ranch home spanning over 5,000 square feet on prestigious Whippoorwill Lane in coveted Weston. Built in 1955 and situated on a magnificent 1.72-acre lot, this timeless residence offers the perfect blend of classic New England charm and modern potential in one of the most sought-after communities. Ready for a new homeowners

Christine Oleynick Keller Williams Realty

Storybook Charm Meets Modern Convenience in Lower Weston! Perched atop a gentle knoll, this beautifully maintained 3-bedroom, 2-bath home offers stunning sunsets, serene pond views, and timeless character. Ideally located in Lower Weston, just minutes from the Westport train station, I-95, and the Merritt Parkway, the home provides a peaceful setting with easy commuting access. Step inside to

William Gill Compass Connecticut, LLC

Spectacular open floor plan highlights this lovely updated 3 bedroom, 3 full bath Ranch in Lower Weston. One level living at its best with dramatic beamed, vaulted ceilings, corner fireplace with wood burning stove, and floor to ceiling windows. Primary Bedroom Suite with vaulted ceiling, updated full bath with walk-in glass shower. Two finished bonus rooms and additional full bath in walk-out

Nancy Manby William Raveis Real Estate

Set on a scenic 2-acre lot surrounded by trees & lush plantings, this home offers a perfect blend of classic style & thoughtful updates, just minutes from Weston's town center & schools. The spacious 5-bedroom, 3.5-bath Colonial welcomes you with a circular driveway, attached 2-car garage, & gleaming hardwood floors that flow through a sun-drenched floor plan designed for comfortable living &

Cynde Koritzinsky William Pitt Sotheby's Int'l

Weston's Best Kept Secret. Stonybrook is a community along the Aspetuck River that offers a private sandy beach, swimming, kayaking, tennis, zip line, and a very special lifestyle. Originally built in 1880, this historic cottage plus legal, rentable, auxiliary dwelling unit, have been thoughtfully restored and reimagined from top to bottom. Upon entering the main house, a light-filled retreat is

Mary Palmieri Gai Berkshire Hathaway NE Prop.

Tranquil Contemporary Retreat on 2.5 Acres in Weston. Tucked away in a peaceful natural setting, this beautifully updated contemporary home offers 2-3 bedrooms and 1,580 square feet of stylish, move-in-ready living space. Set on 2.5 serene acres, the home features gleaming hardwood floors, dramatic beamed and vaulted ceilings, and walls of glass that invite the outdoors in. The spacious living

Yulka Markevich Iron Gates Realty

Classic Clapboard Colonial Farmhouse -Sitting Pretty Atop a Knoll -Welcome to this charming farmhouse perched gracefully at the corner of Lords Hwy. and Graystone Lane, in a peaceful enclave. The home greets you with an inviting front porch and a thoughtfully designed floor plan that blends comfort and character. The sunny eat-in kitchen features updated back splash and light maple cabinetry,

Vickie Kelley Camelot Real Estate

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

Nestled in a serene and private setting, this stunning custom colonial offers the perfect blend of elegance and comfort. Tucked away on over 2 acres of pristine landscape, this meticulously maintained home boasts an inviting layout with exceptional craftsmanship throughout. The sun-filled interior features a beautifully designed custom kitchen, perfect for entertaining. Step outside to a

Adriana Radu Coldwell Banker Realty

Tucked away on a quiet cul-de-sac in sought-after Lower Weston, this extraordinary 4-bedroom retreat redefines modern leisure living. With unrivaled privacy and every amenity at your fingertips, each day feels like a vacation in your very own resort-style oasis. Step inside to discover sun-drenched, open-concept living spaces-perfect for family life and effortless entertaining. Expansive windows

Peter Depalo William Raveis Real Estate

80 K Price Reduction! Amazing Value! Oak Lane is a welcoming, tranquil retreat on a quiet cul de sac in the bucolic town of Weston. Set back, this home offers a private setting with lush, level lawns, lovely gardens/landscaping, a circular driveway, & alluring topography. This home combines the best features of colonial & contemporary elements with high, vaulted ceilings, skylights, open layout,

Lori Elkins William Raveis Real Estate

3 Mayflower Lane offers a perfect blend of modern sophistication and timeless charm. This beautiful home is set on over two idyllic acres, overlooking the Aspetuck Valley Country Club Golf Course. It has been meticulously maintained and upgraded, offering a fresh, contemporary feel while retaining its classic charm. Upon entering the grand foyer with double hight ceilings and a spiral staircase,

Kim Harizman Compass Connecticut, LLC

Modern Transitional Colonial! Built by Jon Rogers and crafted to perfection, no expense was spared creating this well designed home. The epitome of craftsmanship, using only the finest quality materials the fastidious attention to detail & inspired design is evident in every inch of the space.The stunning Kitchen WOWS with white custom cabinetry and top of the line appliances opening to the Great

Todd David Miller William Raveis Real Estate

This exquisite custom estate with pool site on 4.7+/- acres (poss./potential to divide) will take your breath away. Set atop one of the highest points in the area, this luxurious retreat blends modern luxury, convenience, privacy and treetop vistas into one irresistible package. Sited to capture the incomparable views, every room and multiple terraces have gorgeous panoramas, with a circulating

Alex Chingas Coldwell Banker Realty