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Homes for Sale near Winchester High School

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  • 1 Fox Hunt Ln, Winchester, MA 01890
    1 Fox Hunt Ln, Winchester, MA 01890
    1 Fox Hunt Ln, Winchester, MA 01890
    /41

    $2,250,000

    • 5 Beds
    • 5 Baths
    • 5,000 Sq Ft

    1 Fox Hunt Ln, Winchester, MA 01890

    Expanded Colonial Ranch offering over 5,000 sq ft of versatile living space, set on a beautifully landscaped 1/2-acre lot on a quiet cul-de-sac near Winchester Country Club. The first floor features a welcoming formal living room just off the entry, a spacious primary suite with two walk-in closets and a private bath, a guest bedroom with en-suite bath, and a third bedroom or home office.

    Leigh Ventura Compass

    1 Fox Hunt Ln, Winchester, MA 01890
  • 107 Cambridge St, Winchester, MA 01890
    107 Cambridge St, Winchester, MA 01890
    107 Cambridge St, Winchester, MA 01890
    /42

    $2,599,000

    • 6 Beds
    • 4.5 Baths
    • 5,824 Sq Ft

    107 Cambridge St, Winchester, MA 01890

    Gracious and fully restored, this stunning 6-bedroom, 4.5-bath Victorian blends timeless elegance with luxurious modern updates. Rich with sumptuous period details and soaring 9' ceilings, the inviting first floor features a grand marble foyer with custom built-ins and a sweeping staircase. The formal living room offers a stately fireplace, while the chef’s kitchen—complete with expansive quartz

    Maija Sawyer Puleo William Raveis R.E. & Home Services

    107 Cambridge St, Winchester, MA 01890
  • 5 Stratford Rd, Winchester, MA 01890
    5 Stratford Rd, Winchester, MA 01890
    5 Stratford Rd, Winchester, MA 01890
    /39

    $3,599,000

    • 6 Beds
    • 4.5 Baths
    • 5,876 Sq Ft

    5 Stratford Rd, Winchester, MA 01890

    This extraordinary, fully renovated home blends rich architectural detail w/ modern luxury in one of Winchester’s most sought-after neighborhoods. Designed by a shipbuilder, this home offers 5,876 sq ft of elegant living space filled w/ natural light, coffered ceilings, crown moldings, restored hardwood floors & more. The breathtaking chef’s kitchen includes a quartzite island, 8-burner Wolf

    Kim Covino Compass

    5 Stratford Rd, Winchester, MA 01890
  • 9 Prospect St, Winchester, MA 01890
    9 Prospect St, Winchester, MA 01890
    9 Prospect St, Winchester, MA 01890
    /40

    $2,299,000

    • 6 Beds
    • 3.5 Baths
    • 4,667 Sq Ft

    9 Prospect St, Winchester, MA 01890

    Step into timeless elegance with this Colonial Revival, a true celebration of classic architecture, refined style, and exceptional craftsmanship. From the moment you arrive, the home's rich character makes a striking first impression, setting the stage for everything that follows. Inside, you’ll discover a harmonious blend of historic charm and modern comfort. Gleaming hardwood floors, intricate

    Nancy Pallotta Advisors Living - Winchester

    9 Prospect St, Winchester, MA 01890
  • 21 Fernway, Winchester, MA 01890
    21 Fernway, Winchester, MA 01890
    21 Fernway, Winchester, MA 01890
    /42

    $3,175,000

    • 5 Beds
    • 4.5 Baths
    • 5,386 Sq Ft

    21 Fernway, Winchester, MA 01890

    Exceptional colonial on Myopia Hill showcasing an expansive rear family room addition, perfectly situated on an idyllic lot surrounded by lush gardens & mature landscape. This stately residence offers a true private oasis just minutes from all conveniences. Rich in finish, elegant in design w/ stunning living areas, large scale rooms & 4 fireplaces creating warm inviting spaces for every day

    Kim Covino Compass

    21 Fernway, Winchester, MA 01890
  • 10 Sheffield Rd, Winchester, MA 01890
    10 Sheffield Rd, Winchester, MA 01890
    10 Sheffield Rd, Winchester, MA 01890
    /42

    $2,899,000

    • 7 Beds
    • 5.5 Baths
    • 5,864 Sq Ft

    10 Sheffield Rd, Winchester, MA 01890

    This stunning Colonial Revival home, situated on one of Winchester’s most desirable streets, is just moments from the train station, town center, and Ambrose School. The kitchen features radiant floor heating. The first floor includes a chef-designed kitchen, expansive living and family rooms, a formal dining room, a half bath, and a mudroom. On the second floor, you'll find a luxurious master

    Andersen Group Realty Keller Williams Realty Boston Northwest

    10 Sheffield Rd, Winchester, MA 01890
  • 44 Cabot St, Winchester, MA 01890
    44 Cabot St, Winchester, MA 01890
    44 Cabot St, Winchester, MA 01890
    /40

    $3,249,000

    • 6 Beds
    • 6.5 Baths
    • 6,028 Sq Ft

    44 Cabot St, Winchester, MA 01890

    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

    44 Cabot St, Winchester, MA 01890
  • 19 Sussex Rd, Winchester, MA 01890
    19 Sussex Rd, Winchester, MA 01890
    19 Sussex Rd, Winchester, MA 01890
    /26

    $2,249,900

    • 4 Beds
    • 3.5 Baths
    • 4,023 Sq Ft

    19 Sussex Rd, Winchester, MA 01890

    Ideally located in a very desirable neighborhood that abuts the town forest and surrounded by cul-de-sacs, this elegant well-designed 4-bedroom, 3.5-bathroom colonial home has been meticulously maintained by the original owners and features a spacious layout with ample room for comfortable living. The floorplan is thoughtfully designed, with a nice flow from one room to the next. The family room

    Ida Bianco Coldwell Banker Realty - Lexington

    19 Sussex Rd, Winchester, MA 01890
  • 80 Arlington St, Winchester, MA 01890
    80 Arlington St, Winchester, MA 01890
    80 Arlington St, Winchester, MA 01890
    /37

    $3,475,000

    • 5 Beds
    • 3.5 Baths
    • 5,632 Sq Ft

    80 Arlington St, Winchester, MA 01890

    This stunning Royal Barry Wills colonial estate, with 11 rooms, 5 bedrooms and 3.5 baths, is nestled alongside the 4th green of the exclusive Winchester Country Club. Take in views from the sun-splashed eat-in kitchen, complete w/ granite island, custom wood cabinetry, and a generous seating area. Unwind by the fireplace in the richly paneled study. Access the expansive wrap around patio from the

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

    80 Arlington St, Winchester, MA 01890
  • 15 Churchill Rd, Winchester, MA 01890
    15 Churchill Rd, Winchester, MA 01890
    15 Churchill Rd, Winchester, MA 01890
    /41

    $2,599,000

    • 4 Beds
    • 4.5 Baths
    • 5,501 Sq Ft

    15 Churchill Rd, Winchester, MA 01890

    Indulge in modern luxury with this stunning home, set on a double 1/2 acre lot. This 4 bedroom, 4.5-bathroom home seamlessly blends chic style with an abundance of functional space. The architectural design is dramatic, showcasing soaring ceilings, a stunning contemporary fireplace, state of the art kitchen & sun filled living room which opens to a fabulous deck, creating a perfect indoor-outdoor

    Kim Covino Compass

    15 Churchill Rd, Winchester, MA 01890
  • 5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    5 Azalea Rd, Winchester, MA 01890
    /34

    $2,349,000

    • 4 Beds
    • 3.5 Baths
    • 4,959 Sq Ft

    5 Azalea Rd, Winchester, MA 01890

    Pristine Home nestled in Winchester's Sought After West Side Neighborhood and on a Cul de Sac! Open Floor Plan, Very Spacious Granite and Stainless Chef's Kitchen w/Breakfast Bar and Sun-filled Family Room featuring Floor to Ceiling Windows w/ French Doors open to New Composite Deck, Serene Level Backyard w/ Stone Patio, Lush Perennials and Mature Trees to Relax and Enjoy! Elegant Dining Room

    Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

    5 Azalea Rd, Winchester, MA 01890
  • 8 Tanglewood Ln, Winchester, MA 01890
    8 Tanglewood Ln, Winchester, MA 01890
    8 Tanglewood Ln, Winchester, MA 01890
    /42

    $2,650,000

    • 4 Beds
    • 3 Baths
    • 4,276 Sq Ft

    8 Tanglewood Ln, Winchester, MA 01890

    This expansive contemporary residence exudes elegance & sophistication and offers the perfect layout for gatherings & everyday living. This gorgeous home, nestled into a cul-de-sac on the West side was custom designed with soaring ceilings & large scale rooms offering unparalleled views! Enjoy meals in the updated kitchen w/ high end appliances & direct access to deck overlooking private yard.

    Kim Covino Compass

    8 Tanglewood Ln, Winchester, MA 01890
  • 19 Laurel Hill Ln, Winchester, MA 01890
    19 Laurel Hill Ln, Winchester, MA 01890
    /2

    $2,550,000

    • 5 Beds
    • 4.5 Baths
    • 3,800 Sq Ft

    19 Laurel Hill Ln, Winchester, MA 01890

    Nestled on a quiet street in one of Winchester’s most coveted neighborhoods, 19 Laurel Hill Lane will offer refined living just minutes from Boston and top-rated schools. This latest Mark Stephen Development project will feature 4 bedrooms and 4.5 bathrooms, including a flexible first-floor suite perfect for a guest room or study. The heart of the home will be a spacious kitchen flowing into a

    Mark Donnellan Advisors Living - Winchester

    19 Laurel Hill Ln, Winchester, MA 01890
  • 89 Wildwood St, Winchester, MA 01890
    89 Wildwood St, Winchester, MA 01890
    89 Wildwood St, Winchester, MA 01890
    /38

    $2,499,000 Open Sat 11AM - 12PM

    • 7 Beds
    • 5.5 Baths
    • 4,829 Sq Ft

    89 Wildwood St, Winchester, MA 01890

    Brand-New Luxury Construction! This exquisite 7-bedroom, 5.5-bath home blends sophisticated design with functional elegance. Crafted w/ top-tier finishes throughout, the open-concept layout is ideal for modern living & effortless entertaining. The chef’s kitchen showcases an oversized quartz island, premium appliances, & a sunny breakfast nook w/ sliders opening to a private backyard oasis. A

    Monte Marrocco Coldwell Banker Realty - Lexington

    89 Wildwood St, Winchester, MA 01890
  • 32 Oneida Rd, Winchester, MA 01890
    32 Oneida Rd, Winchester, MA 01890
    32 Oneida Rd, Winchester, MA 01890
    /38

    $1,699,000

    • 5 Beds
    • 4 Baths
    • 2,853 Sq Ft

    32 Oneida Rd, Winchester, MA 01890

    Move right into this 5 b/r 4 bth colonial steps to Ambrose School! This picture perfect colonial features high ceilings,hdwd floors & an open first floor plan that creates an airy, welcoming atmosphere.The bright kitchen equipped with ss appliances & charming banquette seating is perfect for casual family meals; step outside to the deck overlooking the spacious yard or into the beautiful

    Stephanie McGowan Better Homes and Gardens Real Estate - The Shanahan Group

    32 Oneida Rd, Winchester, MA 01890
  • 50 Lake St Unit B, Winchester, MA 01890
    50 Lake St Unit B, Winchester, MA 01890
    50 Lake St Unit B, Winchester, MA 01890
    /27

    $625,000

    • 2 Beds
    • 1.5 Baths
    • 1,554 Sq Ft

    50 Lake St Unit B, Winchester, MA 01890

    A well-maintained 2-bed, 1.5-bath townhouse-style condo offering scenic views of Wedge Pond. The main level features hardwood floors, a spacious living area, half bath, and a kitchen with granite countertops and stainless steel appliances. Upstairs offers two bedrooms and a full bath. The finished lower level provides versatile space for a family room, home office, or gym. Additional highlights

    Andersen Group Realty Keller Williams Realty Boston Northwest

    50 Lake St Unit B, Winchester, MA 01890
  • 9 Lakeview Terrace, Winchester, MA 01890
    9 Lakeview Terrace, Winchester, MA 01890
    9 Lakeview Terrace, Winchester, MA 01890
    /42

    $4,250,000 Open Tue 12PM - 1:30PM

    • 5 Beds
    • 3.5 Baths
    • 4,484 Sq Ft

    9 Lakeview Terrace, Winchester, MA 01890

    LAKEFRONT! Nestled on the serene shore of Mystic Lake just 7 miles from Boston, this extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room! Located in one of Winchester’s most sought-after neighborhoods, the home blends high ceilings, rich original details, and a flowing floor plan ideal for both everyday living and

    Kim Covino Compass

    9 Lakeview Terrace, Winchester, MA 01890
  • 49 Lincoln St, Winchester, MA 01890
    49 Lincoln St, Winchester, MA 01890
    49 Lincoln St, Winchester, MA 01890
    /29

    $1,345,000

    • 3 Beds
    • 2 Baths
    • 2,238 Sq Ft

    49 Lincoln St, Winchester, MA 01890

    Enter into the serene in this inviting Colonial, where timeless architecture meets thoughtful updates. High ceilings and sun-splashed, spacious rooms - accented by multiple bay windows and rich wood floors - create a light, airy feel. Featuring a cook’s kitchen with light cherry cabinets, gas cooktop with vented hood, generous storage, and a breakfast nook nestled in a five-window bay overlooking

    Vantage Point Team William Raveis R.E. & Home Services

    49 Lincoln St, Winchester, MA 01890
  • 19 Pilgrim Dr, Winchester, MA 01890
    19 Pilgrim Dr, Winchester, MA 01890
    19 Pilgrim Dr, Winchester, MA 01890
    /42

    $1,775,000

    • 5 Beds
    • 3.5 Baths
    • 3,150 Sq Ft

    19 Pilgrim Dr, Winchester, MA 01890

    Your very own private oasis tucked away in a cul-de-sac-like neighborhood just mins. to Winchester Center! Set on a deep, tree-lined lot, this stunning home offers 5 beds, 3.5 baths, & over 3,000 sq. ft. The versatile floor plan offers ground-level entry w/ a 2 car garage, 2 bedrooms (which can also function as work/play space,) & full bath/laundry area. The upper level is the heart of the home –

    Gorfinkle Group eXp Realty

    19 Pilgrim Dr, Winchester, MA 01890
  • 8 Garfield Ave, Winchester, MA 01890
    8 Garfield Ave, Winchester, MA 01890
    8 Garfield Ave, Winchester, MA 01890
    /38

    $1,199,000

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft

    8 Garfield Ave, Winchester, MA 01890

    Located in a beautiful neighborhood, this thoughtfully renovated 3-bed, 2-bath home with a brand new custom built cottage, blends timeless charm with modern comfort. Sunlight pours into the open living spaces, highlighting original details & gleaming refinished hardwood floors. The inviting living room features a cozy fireplace, while the formal dining room is perfect for gatherings. A bright

    Kim Covino Compass

    8 Garfield Ave, Winchester, MA 01890
  • 35 Harvard St, Winchester, MA 01890
    35 Harvard St, Winchester, MA 01890
    35 Harvard St, Winchester, MA 01890
    /36

    $1,389,000

    • 5 Beds
    • 2 Baths
    • 1,706 Sq Ft

    35 Harvard St, Winchester, MA 01890

    Luscious landscaping and a beautiful farmers porch create amazing curb appeal for this classic colonial in the coveted Muraco School district. Offering a lovely floorplan which offers a welcoming foyer which allows access into the front living room, formal dining room and directly into a large kitchen with plenty of cabinets and granite countertops. The second level features a full bath as well

    Joanne Mulkerin J. Mulkerin Realty

    35 Harvard St, Winchester, MA 01890
  • 6 Francis Circuit Unit 6, Winchester, MA 01890
    6 Francis Circuit Unit 6, Winchester, MA 01890
    6 Francis Circuit Unit 6, Winchester, MA 01890
    /39

    $960,000

    • 2 Beds
    • 2 Baths
    • 1,540 Sq Ft

    6 Francis Circuit Unit 6, Winchester, MA 01890

    Submerge yourself in historic elegance in this meticulously detailed Victorian home, brimming with classic design. Located on one of Winchester’s most serene and desirable cul-de-sacs, this stunning gem overflows with rich architectural details. Inside, you'll find three stately fireplaces, two oversized pocket doors, exquisite antique leaded light fixtures, stained glass, gleaming hardwood

    Katherine Waters-Clark Compass

    6 Francis Circuit Unit 6, Winchester, MA 01890
  • 162 Swanton St Unit 162, Winchester, MA 01890
    162 Swanton St Unit 162, Winchester, MA 01890
    162 Swanton St Unit 162, Winchester, MA 01890
    /32

    $1,299,000 Open Sat 11AM - 12PM

    • 3 Beds
    • 3.5 Baths
    • 2,136 Sq Ft

    162 Swanton St Unit 162, Winchester, MA 01890

    Opportunity to own the last available end unit! Welcome to 162 Swanton Street, the final new construction townhome by Ron Roy in the heart of Winchester. This home blends modern design with exceptional craftsmanship. The open-concept first floor features hardwood floors, a cozy fireplace, and a chef-inspired kitchen with stainless steel appliances, a large island, and adjacent mudroom with half

    Monte Marrocco Coldwell Banker Realty - Lexington

    162 Swanton St Unit 162, Winchester, MA 01890
  • 10 Girard Rd, Winchester, MA 01890
    10 Girard Rd, Winchester, MA 01890
    10 Girard Rd, Winchester, MA 01890
    /41

    $1,349,000

    • 3 Beds
    • 1.5 Baths
    • 3,335 Sq Ft

    10 Girard Rd, Winchester, MA 01890

    Unleash Your Vision in Winchester’s Coveted West Side! Don't miss this rare chance to transform this Mid-Century Modern ranch on a generous 15,024 square foot idyllic lot in one of Winchester’s most desirable neighborhoods. Whether you renovate, expand, or enjoy this home as it is, this 3-bed, 1.5-bath home offers endless potential. Nestled on a quiet, tree-lined street abutting conservation land

    Joanne Sexeny Coldwell Banker Realty - Lexington

    10 Girard Rd, Winchester, MA 01890
  • 44 Amberwood Dr, Winchester, MA 01890
    44 Amberwood Dr, Winchester, MA 01890
    44 Amberwood Dr, Winchester, MA 01890
    /29

    $1,799,999

    • 3 Beds
    • 2.5 Baths
    • 3,002 Sq Ft

    44 Amberwood Dr, Winchester, MA 01890

    Incredibly well maintained, nicely updated 3-4 bedroom Colonial in a wonderful neighborhood in desirable VO School district! The first floor has an oversized kitchen w/cherry cabinets, all granite counters & breakfast bar that opens to a great room with FP and a recently added family room w/vaulted ceiling, computer cubby and 10' slider to a deck overlooking a beautiful landscaped yard & 2

    Hudson Santana Keller Williams Realty Boston Northwest

    44 Amberwood Dr, Winchester, MA 01890
  • 518 Washington St, Winchester, MA 01890
    518 Washington St, Winchester, MA 01890
    518 Washington St, Winchester, MA 01890
    /40

    $1,199,900

    • 4 Beds
    • 2.5 Baths
    • 2,302 Sq Ft

    518 Washington St, Winchester, MA 01890

    Set in the coveted Muraco School District, this classic 1915 Colonial offers the perfect blend of character and modern comfort. Featuring 4 bedrooms and 2.5 baths, the welcoming main level boasts an open-concept layout with an eat-in kitchen (granite countertops, stainless steel appliances), a dining room with charming built-ins, a spacious living room, and a convenient powder room with laundry.

    Rodrigo Serrano Leading Edge Real Estate

    518 Washington St, Winchester, MA 01890
  • 7 Conant Rd Unit 23, Winchester, MA 01890
    7 Conant Rd Unit 23, Winchester, MA 01890
    7 Conant Rd Unit 23, Winchester, MA 01890
    /34

    $689,000

    • 2 Beds
    • 2 Baths
    • 1,160 Sq Ft

    7 Conant Rd Unit 23, Winchester, MA 01890

    Fantastic opportunity to own a freshly updated 2 bed 2 bath condo in Winchester—one of Massachusetts’ top-rated school districts. Located in the desirable Lynch Elementary district, which will open a brand-new school building this fall. This move-in ready home has just been freshly painted, with brand-new kitchen appliances and new carpeting throughout. The open-concept living and dining area

    Xin Cui Hooli Homes Boston

    7 Conant Rd Unit 23, Winchester, MA 01890
  • 18 Brookside Ave, Winchester, MA 01890
    18 Brookside Ave, Winchester, MA 01890
    18 Brookside Ave, Winchester, MA 01890
    /30

    $1,199,000

    • 3 Beds
    • 1.5 Baths
    • 1,573 Sq Ft

    18 Brookside Ave, Winchester, MA 01890

    Charming, fully renovated colonial in a prime Winchester neighborhood! The sunny front porch welcomes you in, leading to a bright bow front living room w/ high ceilings, that flows into the dining room & beautifully updated kitchen w/ stainless appliances & custom cabinetry w/ generous counter space. Off the kitchen, there’s a half bath and a bonus room—great as an office, playroom, or casual

    Kim Covino Compass

    18 Brookside Ave, Winchester, MA 01890
  • 4 Worthen Rd, Winchester, MA 01890
    4 Worthen Rd, Winchester, MA 01890
    4 Worthen Rd, Winchester, MA 01890
    /40

    $2,050,000

    • 5 Beds
    • 3.5 Baths
    • 3,874 Sq Ft

    4 Worthen Rd, Winchester, MA 01890

    Stunning 5 bed 3.5 bath customized colonial situated on a gorgeous street with 1/2 acre lot! This sun-drenched home is filled w/ natural light & is perfectly designed for both everyday living & entertaining. The first floor features a spacious, updated kitchen w/ an oversized island, dining room w fplc & two beautiful great rooms on either side of the home w/ vaulted ceilings, skylights &

    Kim Covino Compass

    4 Worthen Rd, Winchester, MA 01890
  • 22 Grove Place Unit 4, Winchester, MA 01890
    22 Grove Place Unit 4, Winchester, MA 01890
    22 Grove Place Unit 4, Winchester, MA 01890
    /37

    $859,000

    • 2 Beds
    • 1 Bath
    • 1,123 Sq Ft

    22 Grove Place Unit 4, Winchester, MA 01890

    Looking to downsize or just live more modestly?Welcome to the sought-after White Horse Commons Condominiums, The perfect opportunity to enjoy the lovely town of Winchester and keep costs down. Near Symmes corner, downtown Winchester & Wedgemere train station, this wonderful 2 bedroom, 1 bathroom end unit lives and feels like a single home with windows on all three sides. The kitchen offers a

    Kim Covino Compass

    22 Grove Place Unit 4, Winchester, MA 01890
  • 571 Washington St, Winchester, MA 01890
    571 Washington St, Winchester, MA 01890
    571 Washington St, Winchester, MA 01890
    /34

    $1,010,000

    • 3 Beds
    • 1 Bath
    • 1,425 Sq Ft

    571 Washington St, Winchester, MA 01890

    Welcome to this beautifully maintained 3-bedroom home just moments from vibrant Winchester Center. Ideal for commuters with quick access to I-95 and I-93, this home blends charm, comfort, and convenience. The updated kitchen features quartz countertops and generous cabinetry—perfect for cooking and gathering. Light-filled living spaces offer a warm, welcoming feel throughout. Unwind on the

    Ryan Wilson Keller Williams Realty

    571 Washington St, Winchester, MA 01890
  • 25 Wedgemere Ave, Winchester, MA 01890
    25 Wedgemere Ave, Winchester, MA 01890
    25 Wedgemere Ave, Winchester, MA 01890
    /42

    $3,895,000

    • 7 Beds
    • 8 Baths
    • 7,587 Sq Ft

    25 Wedgemere Ave, Winchester, MA 01890

    Stately elegance resides on one of the most desirable streets in the “Flats". This sprawling home details fine craftsmanship & modern finishes that a home of this caliber warrants. Sprawling open concept kitchen w/ impressive coffered ceilings, eat-in dining along w/ an adjoining family rm w/gas fireplace, dining room, and a formal living room make this the perfect space for entertaining. 7

    Prestige Homes Realty Team Prestige Homes Real Estate, LLC

    25 Wedgemere Ave, Winchester, MA 01890
  • 54 Wedgemere Ave, Winchester, MA 01890
    54 Wedgemere Ave, Winchester, MA 01890
    54 Wedgemere Ave, Winchester, MA 01890
    /42

    $3,175,000

    • 6 Beds
    • 3.5 Baths
    • 5,238 Sq Ft

    54 Wedgemere Ave, Winchester, MA 01890

    SELLER WILL INCLUDE 50K of RESTORATION HARDWARE FURNISHINGS *w/ signed offer by 6/16* Exceptional living in this stunning Wedgemere Ave home w/ spectacular resort style back yard! Completely updated throughout w/ custom high end finishes, wonderful chefs kitchen w/ Sub Zero- Wolf appliances, sunny breakfast/dining area w/ a wall of windows overlooking expansive back yard featuring gorgeous patio

    Kim Covino Compass

    54 Wedgemere Ave, Winchester, MA 01890
  • 11 Fieldstone Dr, Winchester, MA 01890
    11 Fieldstone Dr, Winchester, MA 01890
    11 Fieldstone Dr, Winchester, MA 01890
    /41

    $2,899,000

    • 5 Beds
    • 4.5 Baths
    • 6,904 Sq Ft

    11 Fieldstone Dr, Winchester, MA 01890

    Stunning 5BD/4.5BA contemporary estate on a private cul-de-sac in Winchester’s most coveted neighborhood. Modern design with soaring two-story ceilings, skylights, wide-plank hardwoods, and a dramatic stone fireplace. Gourmet chef’s kitchen with all-white waterfall island, Sub-Zero appliances, and butler’s pantry. Luxe primary suite with dual walk-in closet, spa bath, and private terrace. Fully

    Andersen Group Realty Keller Williams Realty Boston Northwest

    11 Fieldstone Dr, Winchester, MA 01890
  • 147 Highland Ave, Winchester, MA 01890
    147 Highland Ave, Winchester, MA 01890
    147 Highland Ave, Winchester, MA 01890
    /37

    $1,329,000

    • 3 Beds
    • 2 Baths
    • 1,884 Sq Ft

    147 Highland Ave, Winchester, MA 01890

    Discover this charming renovated 3 bed 2 bath home with close proximity to the Fells trails & Winchester town center including schools, train to Boston, restaurants, shops & all the town has to offer!! Beautifully renovated & lovingly maintained, this great home welcomes you with a spacious living room w fplc that flows seamlessly into a sun-drenched updated kitchen featuring stainless steel

    Kim Covino Compass

    147 Highland Ave, Winchester, MA 01890
  • 3 Abby Rd, Winchester, MA 01890
    3 Abby Rd, Winchester, MA 01890
    3 Abby Rd, Winchester, MA 01890
    /13

    $2,999,999

    • 5 Beds
    • 4.5 Baths
    • 5,716 Sq Ft

    3 Abby Rd, Winchester, MA 01890

    Welcome to your dream home! This brand-new, meticulously crafted residence offers the perfect blend of luxury & comfort in Winchester’s newest neighborhood. Boasting 4 beds & 4.5 designer baths, every detail has been thoughtfully curated. The chef’s kitchen boasts custom cabinetry, professional-grade appliances & island — ideal for both everyday living & elegant entertaining. The adjoining dining

    Philip Vita Compass

    3 Abby Rd, Winchester, MA 01890
  • 10 Olde Lyme Rd, Winchester, MA 01890
    10 Olde Lyme Rd, Winchester, MA 01890
    10 Olde Lyme Rd, Winchester, MA 01890
    /33

    $1,769,000

    • 5 Beds
    • 3.5 Baths
    • 3,478 Sq Ft

    10 Olde Lyme Rd, Winchester, MA 01890

    Come see this spacious 5-bedroom home offered at a NEW PRICE of $1,769,000! Located near the end of a quiet cul-de-sac in a wonderful neighborhood, this home offers privacy, space and natural beauty, just a short distance to Winchester Center and surrounding towns. Walking distance to the Vinson-Owen school, which has consistently been rated as one of the best elementary schools in the state.

    Darryl Brian RE/MAX Bentley's

    10 Olde Lyme Rd, Winchester, MA 01890
  • 7 Thornberry Rd, Winchester, MA 01890
    7 Thornberry Rd, Winchester, MA 01890
    7 Thornberry Rd, Winchester, MA 01890
    /34

    $1,449,900

    • 5 Beds
    • 2 Baths
    • 3,033 Sq Ft

    7 Thornberry Rd, Winchester, MA 01890

    Renovated Contemporary Split-entry 3 Level home in the highly sought-after Vinson- Owen Elementary and West-side neighborhood. 15 minutes to Downtown Boston. 5 bedrooms, 2 full baths, Living, Dining PLUS family room & 2nd finished room ( play or office) ground level room heated & A/C walk access to outdoor deck & fire pit. Open concept kitchen area. Hardwood floors, 2 fireplace, 2 garage space,

    salim chowdhury TAJ Mahal Realty LLC

    7 Thornberry Rd, Winchester, MA 01890
  • 14 Hillside Ave, Winchester, MA 01890
    14 Hillside Ave, Winchester, MA 01890
    14 Hillside Ave, Winchester, MA 01890
    /42

    $1,499,000

    • 3 Beds
    • 2.5 Baths
    • 2,605 Sq Ft

    14 Hillside Ave, Winchester, MA 01890

    Location, location, location! Rare opportunity to own this stunning Italianate home, in a desirable neighborhood, steps from Town Center! This property has been lovingly owned & maintained by the same family for 70+ years and is now ready for new owners. Prepare to fall in love with the charm and period details of this circa 1870 historic home, the first house built on Hillside Ave. The 1st floor

    Seeme Moreira Coldwell Banker Realty - Lexington

    14 Hillside Ave, Winchester, MA 01890
  • 14 Nassau Dr, Winchester, MA 01890
    14 Nassau Dr, Winchester, MA 01890
    14 Nassau Dr, Winchester, MA 01890
    /42

    $2,850,000

    • 6 Beds
    • 7 Baths
    • 6,968 Sq Ft

    14 Nassau Dr, Winchester, MA 01890

    Stunning Absolutely! Custom-built 6-bedroom house on a large and tranquil lot. 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

    14 Nassau Dr, Winchester, MA 01890

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