Colonial Homes for Sale in Winchester, MA

Winchester Single Family Home with Attached Garage. Completely rebuilt in 2019, 4 Bedrooms + 2 Home Offices & 3.5 Bathrooms across 2,750+ SF! Two "WFH Offices" with Door & Window for privacy. Open-Concept Kitchen: Quartz Island/Countertops & Stainless Steel Appliances. Induction cooking & Hood Venting. Open-Concept Flows into the Connected Dining Room & Sundrenched Living Room with Wood Burning

Collin Bray Century 21 Cityside

Welcome home to this completely renovated gem, ideally situated on a corner lot in the highly sought-after Lincoln Elementary School district. Warm, inviting, and truly move-in ready, this home offers the open-concept first floor buyers dream of—featuring a beautiful kitchen flowing seamlessly into the dining and living areas, plus a sunken family room perfect for relaxing or entertaining. Enjoy

Philip Vita Compass

Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz

Kim Covino Compass

Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where you can entertain with ease throughout the expansive first floor. Here you will find a high-end

Joan Francis Sullivan Better Homes and Gardens Real Estate - The Shanahan Group

Classic curb appeal abounds at this expansive five-bedroom colonial in the desirable Winchester Highlands neighborhood. The sun-filled first floor features a gracious floor plan with a thoughtfully designed eat-in kitchen showcasing premium appliances including a Sub-Zero refrigerator and Fisher & Paykel DishDrawer. A dining room, living room with wood-burning fireplace, office, mudroom and

Dara Singleton Better Homes and Gardens Real Estate - The Shanahan Group

Turnkey-ready 4BR, 3 full bath home set on a beautifully landscaped .82-acre lot directly across from the Swim & Tennis Club, where the new owner receives immediate membership! Extensively renovated & thoughtfully designed, this home offers exceptional style & comfort throughout.The stunning 2026 kitchen features custom cabinetry, quartz countertops, center island, designer backsplash, updated

Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

Nearing completion! This thoughtfully designed new construction home in prime Winchester locations a must see- a handcrafted labor of love, this home welcomes you with immense curb appeal & showcases stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept

Kim Covino Compass

Discover this picture perfect 4 BD 3.5 BA colonial in coveted Brooks neighborhood! This distinguished property offers a gourmet kitchen featuring sleek SS appliances, AGA dual fuel range w/ gas burners, center island & tall wine cooler w/sunny brkfst area. The family rm is an architectural focal point, boasting cathedral ceilings, skylights & a cozy fireplace. Natural light floods the home &

Kim Covino Compass

Truly one of a kind new construction blending timeless design with modern luxury, 8 Priscilla Ln offers 6,500± sq ft of thoughtfully designed living space. Elegant archways and a dramatic two-story living room create an immediate sense of scale and character. The chef’s kitchen features custom cabinetry, Thermador appliances, and an oversized island, flowing seamlessly into the main living and

The Pezzano Group Rise Signature Homes

Ideally situated in one of Winchester's most desirable neighborhoods, 1 Plymouth offers the rare combination of exceptional living space and unmatched convenience just minutes to Winchester Center, top-rated schools, commuter rail access, country clubs, and local amenities.Thoughtfully expanded and rebuilt, this impressive residence features 7 bedrooms, 7 full baths, and 1 half bath, designed to

George Sarkis Douglas Elliman Real Estate - The Sarkis Team

Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England

Weidong Li WINN Real Estate & Consulting

Step into the welcoming foyer and take in the period detail: stained-glass windows, large bow windows, detailed moldings, and hardwood floors. The sun-drenched formal dining room is made for gatherings, and the updated kitchen with butler's pantry makes entertaining a pleasure. On the 2nd floor, the primary suite includes a private office and sleeping porch, along with two additional bedrooms, a

Elena Langlois Compass

Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient

Andersen Group Realty Keller Williams Realty Boston Northwest

Move right into this beautifully updated Colonial set on a level, fenced corner lot. Designed for modern living, this 4-bedroom, 3.5-bath home offers a spacious floor plan with a warm, nature-inspired aesthetic throughout. The inviting family room impresses with a dramatic beamed ceiling, while the primary suite features a cathedral ceiling, walk-in closet & spa-like bath with an oversized

Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group

Exceptionally rare 1911 property, fully renovated on prestigious Rangeley Road, steps to town. Set on what is widely regarded as the most iconic street in Winchester, this 5 bedroom, 4.5 bath home captures the essence of the coveted Rangeley Estates lifestyle. Over 7,300 sq ft of total space & architectural character, blending classic design with modern luxury. Grand, sun drenched interiors & a

Karima Alami Compass

Welcomed by a convenient horseshoe driveway surrounded by thoughtfully designed gardens, 211 Forest has undergone a completely reimagined renovation. This curated family residence shows refined attention to detail and a designer’s eye at every turn. From the custom kitchen with bespoke cabinetry and premium hardware, AGA cast-iron range and Liebherr refrigerator to the sunporch filled with

Michael Gilbert Stuart St James, Inc.

Thoughtfully reimagined with a designer’s eye, this beautifully renovated 4 bed, 3.5 bath home delivers refined living across 3 finished levels. Elevated finishes, including custom tile work, white oak flooring, & curated lighting set this home apart from the typical renovation. The heart of the home is a beautifully designed kitchen with an oversized island & seamless connection to the

Pirani & Wile Group Gibson Sotheby's International Realty

New construction 2019, this impressive 4-5-bedroom, 4.5-bath custom built East side colonial offers exceptional space and a highly sought-after floor plan. The chef's eat-in kitchen features a large center island, abundant cabinetry & sunny dining area that seamlessly blends w/ the spacious family room w built ins & fireplace. Sun-filled living and dining rooms are connected by a double-sided

Kim Covino Compass

Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves

Valerie Post Engel & Volkers Boston

This extraordinary 6-bedroom, 6.5-bath luxury home offers approximately 7,400 square feet of impeccably crafted living space designed for sophisticated living and grand-scale entertaining. A dramatic open-concept floor plan is highlighted by soaring ceilings, a statement fireplace, and expansive walls of Pella windows that flood the interiors with natural light. The designer chef’s kitchen is

Brooke Zarbano Regatta Realty

Must see this completely renovated & expanded stately brick home located just outside the town center offering the perfect blend of timeless charm & modern living. Thoughtfully re-designed with an open concept layout, the home features a custom high end kitchen that flows into a gorgeous oversized family room addition* w/ walls of windows overlooking a stunning private backyard. Formal LR and DR,

Kim Covino Compass

Exceptional new construction offering approximately 6,000 sq ft of thoughtfully designed living space with 6 bedrooms, 7.5 baths, and a 3-car garage. A striking exterior showcases natural stonework, copper roof accents, copper gutters, and a welcoming covered porch. Inside, custom millwork, wide-plank hardwood floors, soaring ceilings, a floating staircase, and designer finishes create a timeless

The Boston ONE Team Serhant

Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming

Kim Covino Compass

Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming

Kim Covino Compass

This completely remodeled home is nestled on a dead end street off Brookside Road, offering a serene/ natural setting with unmatched privacy. This home offers 4 bedrooms, and 2.5 baths with three spacious finished levels. The completely reimagined open concept main floor features a stunning kitchen open to dining area and large family room, plus a separate living room, mudroom, half bath and

Kim Covino Compass

True private resort living. Set on a private .73-acre lot in one of Lexington’s most coveted neighborhoods, This home offers over 10,500SF of curated living & entertaining space w/ 7 beds & 7.5 baths. Privately sited behind mature landscaping, this estate blends timeless architecture w/ resort-style amenities. Dramatic two-story foyer w/ arched windows, formal living & dining rooms, expansive

Ricardo Rodriguez Coldwell Banker Realty - Boston