Winchester, MA Homes for Sale with Garage

Nestled in one of Winchester's most picturesque cul-de-sacs, this elegant English Tudor is available for the first time in 60 years. Passed quietly through word of mouth, this is a rare opportunity to own a piece of Winchester's architectural history. Located near Lincoln School & Winchester Fells' scenic trails, the setting is both serene and convenient. Designed by renowned architect Harry M.

Anne Spry Barrett Sotheby's International Realty

Experience the perfect blend of craftsmanship & modern luxury in this stunning custom-built brick ranch. From the moment you enter the spacious front foyer, you’re greeted by soaring cathedral beamed ceilings & an inviting open-concept layout that seamlessly connects the living, dining, & family areas—ideal for effortless entertaining & comfort. A thoughtfully designed private wing includes 4

Anne Spry Barrett Sotheby's International Realty

One of Winchester’s most beloved neighborhoods sets the tone for 30 Prospect Street, a beautifully reimagined home transformed by an extensive remodel less than five years ago. A spectacular, fully renovated Chef's kitchen anchors the main level with high-end finishes and a seamless flow for living and entertaining. The living room is sunny and inviting, featuring an impressive fireplace,

Karima Alami Compass

Welcome to 89 Wildwood — Winchester’s best new value, where modern design meets classic New England charm! This new construction home offers a flexible layout with spaces for hosting, relaxing & everyday living. The chef’s kitchen impresses with an oversized island, stylish finishes, ample cabinetry & opens to a designated dining area. Fireplaced family room, bedroom/office with ensuite & half

George Sarkis Douglas Elliman Real Estate - The Sarkis Team

This beautifully updated Winchester residence combines timeless Garrison-style architecture with elegant modern finishes, creating a seamless space for everyday living. The inviting foyer leads to a sunlit living room, where wide-plank oak flooring flows into a stunning chef’s kitchen equipped with a spacious pantry, double ovens, and an oversized island—perfect for both cooking and gathering.

Jody Geany Citylight Homes LLC

Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining area that opens to a warm, fireplaced living room. From there, step into the stunning screened-in

Philip Vita Compass

NEWER CONSTRUCTION! This 2020 home showcases 5 beds, 4 baths-4300sf of style & luxury situated on the corner of Loring Ave. The home features high ceilings, hardwood floors & a stunning sunny open floor plan w/ eat in kitchen, center island, custom cabinetry, stainless appliances & walk-in pantry. Formal dining room & dramatic oversized family room will impress, featuring vaulted ceilings, gas

Kim Covino Compass

Welcome to 8 Priscilla Ln, Winchester—a brand-new 5 bed, 5.5 bath luxury home designed by Salt & Stone Co where elevated craftsmanship meets everyday comfort. Spanning 6,500 ± sq ft, this home features a chef’s kitchen with custom cabinetry, premium appliances, and an oversized center island flowing into a dramatic two-story living room with fireplace and glass slider to the backyard. The

The Pezzano Group Rise Signature Homes

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

Welcome to 15 Wildwood Street — a quintessential Winchester residence offering timeless character, modern amenities & endless potential. Ideally situated on a beautiful lot close to the town center. This charming home is impeccably maintained & move-in ready, while providing the opportunity for thoughtful updates to further enhance its value. Step inside to a sun-filled living room w/oversized

Kim Covino Compass

NEW PRICE & UPDATES BEAUTIFULLY REIMAGINED!Welcome home to this stunning brick ranch tucked on a quiet cul-de-sac in Winchester’s coveted West Side. Every space has been thoughtfully designed, blending classic craftsmanship with distinct elegance. The bright open layout invites you in with a chef’s granite and stainless kitchen, sun-filled family room framed by floor-to-ceiling windows, and

Anthony Marino The Marino Group Collection

New roof. New landscaping. New exterior paint. New price! With its coveted setting, elegant bones, and enduring charm, this Royal Barry Wills home awaits your personal design statement. Ideally located on the 4th green of Winchester Country Club’s storied Donald Ross-designed course, this beloved home offers 11 rooms, 5 bedrooms and 3.5 baths. Enjoy views from the sun-splashed eat-in kitchen w/

Carolyn Vernaglia Better Homes and Gardens Real Estate - The Shanahan Group

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

Great value in Town! Discover the perfect blend of luxury and comfort in this stunning 6-bedroom home. Sunlight pours into the open-concept layout, highlighting a gourmet kitchen with stone countertops, an oversized island, and high-end Viking appliances. The inviting living room, featuring a shiplap fireplace, opens to a spacious composite deck. The primary suite is a private retreat with a

Alina Wang Coldwell Banker Realty - Lexington

Elegantly sited on Morningside Hill, this home is a luxury-built masterpiece. Thoughtfully designed & artfully crafted, it exudes opulence & cozy comfort. A gracious entry hall welcomes you into sophisticated living, highlighted by a breathtaking two-story living room adorned with countless windows. The chef's kitchen, a culinary haven, is equipped with state-of-the-art Thermador appliances,

Suzanne Koller Compass

Mid Century Side Hall Colonial w Attached Garage on an Attractive Corner Lot in Winchester. Available for the first time in more than fifty years, this inviting home awaits its next owners' vision and personal touch. Exceptional opportunity to add immediate value with the right repairs and upgrades. Main floor features an open living room with fireplace, adjoining dining room with southwest

William Cordts Charlesgate Realty Group, llc

This charming Cape style home on a half-acre lot combines classic character with modern updates. Step inside to find newly refinished hardwood floors throughout the inviting fireplaced living room, dining room, and bedrooms. The recently updated kitchen and bathrooms blend style and function with contemporary finishes. The dining room with built-in China cabinet provides an inviting space to

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

Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining area that opens to a warm, fireplaced living room. From there, step into the stunning screened-in

Philip Vita Compass

Beautiful 2BR/2BA waterfront condo at Wedgewood Place located at 666 Main Street. This open-concept corner unit features a bright living/dining area with private balcony, granite counter-tops in the kitchen, and hardwood floors. The primary bedroom is bright with lots of windows and offers a walk-in closet and en-suite bath. Additional highlights include in-unit laundry hook-ups, garage parking,

Walace Nogueira

Beautiful 3 bed, 2.5 bath home set on a generous lot in a fantastic Winchester location/ Lincoln Elementary close to town, schools, the train, and route to Boston. The first floor offers an ideal layout with an updated kitchen, stainless steel appliances & island w seating open to a lovely family room flooded with sunlight, plus a spacious living room w fplc and dining room. A 3 season sunroom in

Kim Covino Compass

Welcome to this beautifully updated home! The interior boasts fresh interior paint, all new lighting with refinished hardwood flooring. The living room features a cozy fireplace, perfect for relaxing evenings. The kitchen is a chef's dream with all new stainless steel appliances, new cabinets, and new counter tops with an accent backsplash adding a touch of elegance. The primary bathroom is

DANIEL BEIRNE OpenDoor Brokerage LLC

Charming Spanish-style home in desirable Winchester! This unique property features a beautiful terracotta roof and timeless architectural details. The first floor welcomes you with a foyer which leads to an astounding great room, perfect for entertaining or hosting family gatherings. The kitchen opens seamlessly to the dining area. Additionally an inviting enclosed patio provides space to relax

Andersen Group Realty Keller Williams Realty Boston Northwest

Charm and character meet modern living in this beautifully renovated & expanded Victorian townhome just steps from Winchester Center. Fully updated in 2013/14 with new kitchen, baths, wiring, all systems, roof, and windows—and enhanced in 2023 with a redesigned patio, landscaping, fencing, and flower beds—in the exclusive yard. This home offers four levels of sun-filled space. The main level

Kim Covino Compass

Location, Location, Location! This beautifully maintained 3-bedroom, 2.5 bath multi-level home perfectly balances convenience and suburban charm. Enjoy an easy walk to the commuter rail, downtown shops and restaurants, schools, parks, and more. The main level features a spacious, sun-filled open floor plan with fireplaced living room, updated kitchen with skylight, and a bright sunroom offering

Taleen Chiofaro Leading Edge Real Estate

27,000 SF lot!!! Set far back from the street~ Don't miss this opportunity! Whether looking to lightly update/ expand or completely renovate; this well maintained 3 bedroom split entry home with a stunning oversized private yard offers tremendous potential! The first floor is spacious with large sunny rooms incl. a generously sized living room with picture window & wood burning fireplace, a

Kim Covino Compass

Welcome to 44 Cabot Street, a newly built home in one of Winchester’s most desirable neighborhoods. Offering over 6,000 square feet of beautifully crafted space, this residence features 6 bedrooms, 6.5 bathrooms, and a layout designed for modern living. Thoughtfully selected finishes, high ceilings, and an abundance of natural light create a warm and inviting atmosphere throughout. The

Andersen Group Realty Keller Williams Realty Boston Northwest

Amazing custom-built 6-bedroom / 5+ bathroom house on a quiet neighborhood in Winchester. 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

Weidong Li WINN Real Estate & Consulting

This Expanded Cape features a fireplace living room, built in bookcases, and glistening hardwood floors throughout. The spacious kitchen has a dining area which opens to the living room for an entertaining atmosphere. The 2nd floor Master bedroom suite has a balcony to enjoy your morning coffee. The inviting 3 season porch with flagstone floor is a favorite place for family to congregate and get

Pavan Patel Realty ONE Group Nest

Best valued single family in Winchester with incredible fenced backyard and expansive patio extending your living space outdoors, and 2 car garage!! Build immediate equity and convenience by adding an additional bathroom - Plans and renderings in hand (see attached and ask agent for details)! Designed with light-filled living spaces and three generously sized bedrooms, it’s a perfect fit for

Ryan Wilson Keller Williams Realty

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

Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck,

Kim Covino Compass

Discover this brand-new custom-built home featuring 6 bedrooms and 7 full baths, located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador

Wei Wang WW Real Estate LLC

From the moment you enter this European-style Victorian, you’ll be charmed. The first level features an eat-in kitchen with quartz countertops, LG Café appliances, wine fridge, island, and large windows, plus a living room, den, and half bath. The second floor offers a primary suite with skylight, ceiling fan, two walk-in closets, balcony, jacuzzi bath, and steam shower. Two more bedrooms and a

Andersen Group Realty Keller Williams Realty Boston Northwest

This STUNNING newly constructed home facing Old Village Drive redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the

Kim Covino Compass

Another Tree Top Group masterpiece –Welcome to 4 Wyman Court! New full gut renovation townhome with 2,500 sq. ft., 4 beds, 4.5 baths & 4 levels of sun-drenched living space. Located in a prime end of cul-de-sac & moments from the vibrant Winchester Center including shops, dining & commuter rail. Main level features a thoughtfully designed kitchen w/ stainless steel appliances, a large center

Monte Marrocco Coldwell Banker Realty - Lexington

An extremely rare new construction in the Flats, this stunning 6BD/4.5BA home is a ground-up rebuild blending modern luxury with timeless warmth in one of Winchester’s most coveted neighborhoods. Designed for elevated living, it features a chef’s kitchen with quartz counters, custom cabinetry, a large island, and built-in bar, opening to a sunlit dining area ideal for both casual meals and

Monte Marrocco Coldwell Banker Realty - Lexington

New Construction at Highland at Vale in Woburn! The Jackson floor plan offers over 2,900 sq. ft. of living space, including a finished basement. The bright kitchen features abundant cabinetry, stainless steel appliances, and a large island that opens to a spacious gathering room and a distinctive octagon-shaped dining area with bay window. Enjoy wooded views from your private deck—perfect for

Erin Sullivan Pulte Homes of New England

This stunning new construction end-unit townhome offers 3 bedrooms, 3.5 bathrooms, and a finished basement with full bath—perfect for flexible living or guest space. The chef’s kitchen boasts stainless steel appliances, a large center island, and abundant cabinetry, opening seamlessly to the spacious living room and private deck. A formal dining room with a charming bay window adds warmth and

Erin Sullivan Pulte Homes of New England

New Construction Move- In Ready Townhome at Highland at Vale in Woburn! The Jackson floor plan offers over 2,100 sq. ft. of thoughtfully designed living space with 3 spacious bedrooms and 2.5 baths. The main level features a bright kitchen with stainless steel appliances, abundant cabinetry, and a large center island, flowing into an oversized gathering room and an octagon-shaped dining room with

Erin Sullivan Pulte Homes of New England