Homes for Sale near Winchester High School

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  /34

  $974,900

  • 3 Beds
  • 2.5 Baths
  • 1,719 Sq Ft

  258 Cross St, Winchester, MA 01890

  A rare opportunity to own a detached home in Winchester under $1M—with the space, privacy and flexibility often missing from condo or townhome living. Tired of or can't imagine paying an HOA fee on top of fighting rising interest rates? Skip the added cost, lock in (REFI LATER) a lower monthly payment, and get more value at 258 Cross Street! The property is set on a level, fenced corner lot with

  

  Justin Blankenship

  Fiv Realty Co

  258 Cross St, Winchester, MA 01890
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  Explore Winchester High School

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  /29

  $949,999

  • 4 Beds
  • 2 Baths
  • 2,326 Sq Ft

  96 Loring Ave, Winchester, MA 01890

  Discover a rare opportunity to own a versatile ranch in sought-after Winchester, offering flexible living with a two-bedroom main level and a full two-bedroom in-law suite below. The gracious first floor welcomes you with gleaming hardwood floors and a handsome fireplace anchoring the living room. A generously proportioned dining room, complete with a classic built-in china cabinet, opens

  

  Jeremy Smith

  StartPoint Realty

  96 Loring Ave, Winchester, MA 01890
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  /24

  $495,000

  • 2 Beds
  • 1 Bath
  • 822 Sq Ft

  200 Swanton St Unit 303, Winchester, MA 01890

  Enjoy the best of Winchester living in this beautifully updated two-bedroom condo at Parkview, just minutes from Winchester Center, local shops, dining, parks, and commuter access. A bright, open-concept layout creates an inviting flow for everyday living and entertaining. The modern kitchen features stainless steel appliances, while fresh paint throughout adds a crisp, contemporary feel. Both

  Joseph Pollack Redfin Corp.

  200 Swanton St Unit 303, Winchester, MA 01890
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  /40

  $2,199,000

  • 4 Beds
  • 3.5 Baths
  • 3,570 Sq Ft

  19 Hancock St, Winchester, MA 01890

  Welcome to 19 Hancock Street, a stunning transformation where timeless New England character meets sophisticated modern living. Completely reimagined through an extensive renovation, this exceptional Winchester residence preserves the charm and presence of a classic home while delivering the design, finishes and functionality expected for today’s lifestyle. The beautifully designed first floor

  Philip Vita Compass

  19 Hancock St, Winchester, MA 01890
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  /41

  $1,749,000

  $50K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,010 Sq Ft

  1 Town Way, Winchester, MA 01890

  Welcome home to this beautifully renovated gem, perfectly positioned 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 today’s buyers are looking for—featuring a stunning kitchen that flows effortlessly into the dining and living areas, plus a sunken family room ideal for relaxing

  Philip Vita Compass

  1 Town Way, Winchester, MA 01890
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  /23

  $630,000

  $99K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,494 Sq Ft

  247 Washington St Unit 11, Winchester, MA 01890

  Ideally located just minutes from vibrant downtown Winchester, this spacious condominium offers easy access to shopping, restaurants, the Farmer's Market, library, award-winning schools, parks, and the commuter rail. The renovated kitchen features custom maple cabinetry, granite countertops, a breakfast bar, and an open-concept layout that flows seamlessly into the living area—perfect for

  Heejeong Joo Coldwell Banker Realty - Lexington

  247 Washington St Unit 11, Winchester, MA 01890
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  /40

  $1,099,000

  • 4 Beds
  • 2.5 Baths
  • 2,411 Sq Ft

  24 Richardson St, Winchester, MA 01890

  Tucked on a quiet side street just north of Main Street, this circa-1853 antique pairs the character of a classic Winchester home with the space of a beautiful, sun-filled addition (completed in 2003): A lovely farmer's porch welcomes you and, once inside, hardwood and tile floors run through the main living spaces. Front rooms include a quaint sitting room and private office. A gas fireplace

  Andersen Group Realty Keller Williams Realty Boston Northwest

  24 Richardson St, Winchester, MA 01890
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  /4

  $3,200,000

  • 5 Beds
  • 5.5 Baths
  • 5,295 Sq Ft

  18 Ridge St, Winchester, MA 01890

  Introducing 18 Ridge Street — a masterfully restored and reimagined Greek Revival residence where timeless architectural beauty meets elevated modern luxury. Set on a beautifully landscaped 20,654 sq ft lot, this exceptional 5-bedroom, 5 full and 1 half bath home offers over 5,295 square feet of exquisitely curated living space designed for both sophisticated entertaining and everyday comfort.

  Gayle Winters Compass

  18 Ridge St, Winchester, MA 01890
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  /42

  $1,650,000

  • 5 Beds
  • 3.5 Baths
  • 3,722 Sq Ft

  117 Highland Ave, Winchester, MA 01890

  Expansive living and unparalleled curb appeal define this exceptional five-bedroom garrison colonial, ideally positioned near the natural beauty and extensive trails of the Fells Reservation. Set in the highly regarded Muraco Elementary School district, this spacious home offers an inviting blend of timeless architecture, thoughtful updates, and remarkable flexibility for today’s lifestyle. The

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

  117 Highland Ave, Winchester, MA 01890
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  /42

  $3,200,000

  $200K PRICE DROP

  • 6 Beds
  • 5.5 Baths
  • 6,100 Sq Ft

  9 Albamont Rd, Winchester, MA 01890

  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

  9 Albamont Rd, Winchester, MA 01890
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  /42

  $1,699,000

  • 3 Beds
  • 2 Baths
  • 2,421 Sq Ft

  4 Churchill Rd, Winchester, MA 01890

  OPEN HOUSES THIS WEEKEND! 11:30-1 Sat & Sun 9/19 &9/20 ** Extensively rebuilt and expanded, this impeccably maintained 3/4 Bed 2 BA home offers a spacious and versatile floor plan. The impressive 28’ x 20’ great room features vaulted ceilings, bay window, and a gas fireplace which flows nicely from the updated kitchen. Step outside to a new oversized Azek deck with plenty of room for grilling,

  Kim Covino Compass

  4 Churchill Rd, Winchester, MA 01890
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  /32

  $2,695,000

  $100K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 5,233 Sq Ft

  18 Middlesex St, Winchester, MA 01890

  Seller to offer a buyer credit paying up to 2% of loan size for buyer at closing that can go to a permanent or temporary rate buydown. European inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes,

  Tina Natale Luxury Living Real Estate

  18 Middlesex St, Winchester, MA 01890
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  /42

  $1,870,000

  $29K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,210 Sq Ft

  79 Grove St, Winchester, MA 01890

  As close to new construction as you’ll find, this exceptional Colonial was comprehensively renovated in 2016, with numerous additional improvements since. Sophisticated and comfortable, the home offers beautifully scaled living spaces and a versatile floor plan designed for everyday living and entertaining alike. The sun-filled main level features hardwood floors, elegant architectural details,

  Pirani & Wile Group Gibson Sotheby's International Realty

  79 Grove St, Winchester, MA 01890
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  /42

  $1,350,000

  • 4 Beds
  • 3 Baths
  • 2,690 Sq Ft

  423 Washington St, Winchester, MA 01890

  Architecturally distinctive and beautifully renovated throughout, this unique home blends historic character with the comfort of modern living. The home offers exceptional curb appeal and privacy with mature evergreens, specialty trees, and an elevated setting. Inside, a central staircase creates a focal point while naturally defining the open concept living and dining rooms, perfect for everyday

  Danielle Fleming MA Properties

  423 Washington St, Winchester, MA 01890
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  /39

  $799,000

  $101K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,083 Sq Ft

  84 Oak St, Winchester, MA 01890

  $5000 Closing Costs Credit to Buyer closing by Oct. 31st. Best Value in Winchester! Charming and Spacious Custom Built Mid-Century Bungalow offers a terrific opportunity to live in Winchester! Do you want to send your children to the award-winning public schools? Need an in-law apt.? Generously sized, sun-drenched, freshly painted rooms with high ceilings and hardwood floors, beautiful

  John Magazzu Charlesgate Realty Group LLC

  84 Oak St, Winchester, MA 01890
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  /38

  $1,999,000

  • 4 Beds
  • 2.5 Baths
  • 3,757 Sq Ft

  85 High St, Winchester, MA 01890

  Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a

  Catherine Albiani Better Homes and Gardens Real Estate - The Shanahan Group

  85 High St, Winchester, MA 01890
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  /22

  $849,000

  • 3 Beds
  • 1.5 Baths
  • 1,340 Sq Ft

  15 Clark St Unit 17, Winchester, MA 01890

  Walkable to nearly everything, 15 Clark St presents and exceptional opportunity to enjoy refined living in one of Winchester's sought-after neighborhoods. This sun-drenched duplex offers 3 bedrooms, 1.5 bathrooms, and approx 1,336 sq ft of thoughtfully curated living space. Rich hardwood and pine floors, soaring natural light, and an effortless flow in layout create a warm and sophisticated

  Jeffrey Hsu Coldwell Banker Realty - Milton

  15 Clark St Unit 17, Winchester, MA 01890
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  /38

  $4,299,000

  • 5 Beds
  • 5.5 Baths
  • 6,526 Sq Ft

  4 Dartmouth St, Winchester, MA 01890

  Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully renovated, maintained and updated, blending classic architecture with modern comfort. This 5-bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined

  Nancy Pallotta Gibson Sotheby's International Realty

  4 Dartmouth St, Winchester, MA 01890
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  /16

  $399,000

  Open Sat 10AM - 12PM

  • 1 Bed
  • 1 Bath
  • 613 Sq Ft

  200 Swanton St Unit 727, Winchester, MA 01890

  Welcome to Parkview Condominiums in Winchester! This well-maintained 1-bedroom, 1-bathroom condo offers comfortable living in a desirable location. The spacious living room features a glass slider that opens to a private balcony overlooking the pond and garden, perfect for relaxing and enjoying the peaceful surroundings. The condo fee includes all utilities, including heat, hot water, and

  Alice Zheng Shore Real Estate LLC

  200 Swanton St Unit 727, Winchester, MA 01890
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  /42

  $3,450,000

  • 6 Beds
  • 4.5 Baths
  • 5,735 Sq Ft

  7 Hutchinson Rd, Winchester, MA 01890

  Situated on a generous18,000SF level lot! Must see this custom built spectacular masterpiece by some of winchester's finest builders, offering unique architectural design and dramatic finishes showcasing a fabulous dining room w/ a custom wine wall cabinet, gorgeous kitchen, with high end 48 inch gas range w/double ovens, 48"paneled fridge, 10' island w/ seating & a walk in pantry! Enter from the

  Kim Covino Compass

  7 Hutchinson Rd, Winchester, MA 01890
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  /37

  $975,000

  $125K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  83 Church St Unit 15, Winchester, MA 01890

  Stunning corner unit, fully renovated 2 BR,1.5 BA condo offering an exceptional blend of elegance & modern updates in a prime in-town location.Soaring ceilings, dramatic arched openings, & oversized windows flood the space w/natural light.French doors open to charming private balcony.Main living area showcases beautifully refinished marble flooring, gas FP, & designer lighting including crystal

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

  83 Church St Unit 15, Winchester, MA 01890
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  /42

  $685,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,170 Sq Ft

  666 Main St Unit 211, Winchester, MA 01890

  NEW PRICE! Great layout and numerous recent improvements make this a wonderful opportunity! Inviting open layout with abundant natural light coming through NEW TRIPLE-PANE WINDOWS and NEW SLIDER for improved energy efficiency and beauty. Kitchen features updated appliances, granite counters with an eating bar and pantry closet; open to living room with fireplace and dining room with new

  Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  666 Main St Unit 211, Winchester, MA 01890
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  /21

  $774,900

  $24K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft

  50 Middlesex St Unit 52, Winchester, MA 01890

  Completely renovated from top to bottom, this brand-new 2-bedroom, 2-bath condo offers the privacy and feel of a single-family home in one of Winchester's most desirable neighborhoods. Tucked away on a quiet, tree-lined street just moments from vibrant downtown, this home features its own private entrance, driveway, and backyard. Inside, enjoy white oak hardwood floors, a stunning chef's kitchen

  The North Star Group Keller Williams Realty Evolution

  50 Middlesex St Unit 52, Winchester, MA 01890
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  /42

  $3,149,000

  • 7 Beds
  • 7.5 Baths
  • 8,540 Sq Ft

  37 Mayflower Rd, Winchester, MA 01890

  Magnificent newer sun-filled Colonial ideally situated in a premier West Side cul-de-sac, offering over 8,000 sq ft of beautifully finished living space across four levels-A great price at only $368psf! !Designed for grand-scale entertaining and multi-generational living, this exceptional home features 7 bedrooms, 7.5 baths, four fireplaces and a 3-car direct-entry garage, all complemented by

  Kim Covino Compass

  37 Mayflower Rd, Winchester, MA 01890
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  /30

  $899,000

  $51K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,356 Sq Ft

  47 Water St, Winchester, MA 01890

  Warmth, charm, and an exceptional location come together in this inviting 3-bedroom home. Beautiful wood floors, natural woodwork, French doors, and custom built-ins add character throughout. Generous living spaces provide room to gather, relax, and entertain, while the home's classic appeal offers the perfect opportunity to enjoy today or personalize over time. A detached 2-car garage adds

  The Mary Scimemi Team Leading Edge Real Estate

  47 Water St, Winchester, MA 01890
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  /42

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 2,973 Sq Ft

  7 Sherman Place, Winchester, MA 01890

  Move-in-ready luxury townhouse in Winchester with the space, privacy, and single-family-home feel rarely found in condominium living. Built in 2005 and thoughtfully updated, 7 Sherman Place is set on a cul-de-sac and offers 3,095 square feet across four finished levels with four bedrooms, two-and-a-half baths, a private one-car garage, and outstanding indoor and outdoor living spaces.The bright,

  John Dean Engel & Volkers Boston

  7 Sherman Place, Winchester, MA 01890
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  /42

  $2,100,000

  • 4 Beds
  • 3.5 Baths
  • 3,640 Sq Ft

  7 Wainwright Rd Unit 113, Winchester, MA 01890

  Experience elevated living in this exquisitely renovated luxury townhouse at The Ledges! This sought-after condominium community, just minutes from Winchester Center, offers the ease of low-maintenance living w/ the feel of a single-family home, plus exceptional amenities including a private clubhouse, swimming pool, & tennis courts. Featuring the community's most desirable floor plan, this home

  Kim Covino Compass

  7 Wainwright Rd Unit 113, Winchester, MA 01890
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  /17

  $1,098,000

  • 3 Beds
  • 1.5 Baths
  • 1,657 Sq Ft

  17 Russell Rd, Winchester, MA 01890

  Welcome to 17 Russell Rd, a meticulously maintained and updated 3-bedroom, 1.5-bath home in a highly desirable Winchester neighborhood! A charming mudroom with beadboard accents and radiant heated floors welcomes you into a bright open-concept layout with gleaming hardwood floors throughout. Enjoy a sun-filled living room with cozy bow window seating, a spacious kitchen with rich cabinetry, and a

  KoKo Kwan Kwan Realty Inc.

  17 Russell Rd, Winchester, MA 01890
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  /35

  $2,995,000

  • 5 Beds
  • 5.5 Baths
  • 6,500 Sq Ft

  8 Priscilla Ln, Winchester, MA 01890

  A distinctive new construction home where exceptional scale, thoughtful design, and refined finishes come together. Offering approximately 6,500 sq ft of beautifully finished living space, 8 Priscilla Ln was designed to feel impressive yet inviting. Soaring ceilings, graceful archways, and a dramatic two-story living room establish the home's architectural character, while an open, flowing layout

  The Pezzano Group Rise Signature Homes

  8 Priscilla Ln, Winchester, MA 01890
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  /42

  $2,600,000

  • 6 Beds
  • 4 Baths
  • 3,534 Sq Ft

  7 Lakeview Terrace, Winchester, MA 01890

  RARE WATERFRONT OPPORTUNITY on Upper Mystic Lake with spectacular sunset views! Tucked away on Lakeview Terrace, this special 1910 home offers a combination rarely found in Winchester: waterfront living, privacy, beautiful southwest light and exceptional convenience. Gracious rooms, period details and quality craftsmanship give the home wonderful character, while its generous layout offers an

  Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  7 Lakeview Terrace, Winchester, MA 01890
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  /36

  $2,100,000

  $100K PRICE INCREASE

  • 6 Beds
  • 5 Baths
  • 3,403 Sq Ft

  6 Ivy Cir, Winchester, MA 01890

  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

  6 Ivy Cir, Winchester, MA 01890
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  /41

  $769,000

  • 2 Beds
  • 2 Baths
  • 1,170 Sq Ft

  666 Main St Unit 310, Winchester, MA 01890

  Don't miss this beautifully appointed 2-bedroom, 2 bath unit at Wedgewood Place, a waterfront condominium community that is centrally located in downtown Winchester. Magnificent new kitchen with custom cabinets, quartz counter tops and stainless-steel appliances that looks out at a bright and sunny, spacious open living and dining room and small home office area. Featuring a wood burning

  Darryl Brian RE/MAX Bentley's

  666 Main St Unit 310, Winchester, MA 01890
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  /42

  $1,350,000

  • 2 Beds
  • 2.5 Baths
  • 1,573 Sq Ft

  36 Elmwood Ave Unit 11, Winchester, MA 01890

  Introducing 36 Elmwood Avenue, Unit 11 - a penthouse residence at Allegro with Winchester Center's shops, restaurants & commuter rail right outside your door. Built in 2021, this 2 bedroom / 2.5 bath home w/ 2 GARAGE PARKING SPACES offers 1,573 sqft and the best layout in the building. Loads of upgrades throughout! The open living, dining & kitchen area is bright and great for entertaining, with

  The Rasner Group Keller Williams Realty Boston-Metro | Back Bay

  36 Elmwood Ave Unit 11, Winchester, MA 01890
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  /24

  $849,000

  • 3 Beds
  • 1.5 Baths
  • 1,340 Sq Ft

  15 Clark St Unit 15, Winchester, MA 01890

  Walkable to nearly everything, 15 Clark St presents an exceptional opportunity to enjoy refined living in one of Winchester's most sought-after neighborhoods. This sun-drenched townhome offers 3 bedrooms, 1.5 bathrooms, and approximately 1,336 sq ft of thoughtfully curated living space. Rich hardwood floors, soaring natural light, and an effortless open layout create a warm yet sophisticated

  Jeffrey Hsu Coldwell Banker Realty - Milton

  15 Clark St Unit 15, Winchester, MA 01890
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  /37

  $1,749,000

  • 5 Beds
  • 3.5 Baths
  • 3,508 Sq Ft

  17 Churchill Rd, Winchester, MA 01890

  A rare offering in one of Winchester's most desirable neighborhoods, this spacious mid-century contemporary spans approximately 3,500 square feet with 5 bedrooms and 3.5 baths on a private 0.24-acre lot. The open main level flows from a light-filled living room with a cathedral ceiling, stained-glass accents, and a fireplace into the dining room, family room, and a renovated kitchen with

  Domingo Medina Coldwell Banker Realty - Lexington

  17 Churchill Rd, Winchester, MA 01890
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  /42

  $1,599,000

  • 5 Beds
  • 3 Baths
  • 2,944 Sq Ft

  143 Arlington St, Winchester, MA 01890

  JOIN US FOR AN OPEN HOUSE SATURDAY 9/19 11-12;30! Set on a generous lot in one of Winchester’s most highly sought-after locations, this stately brick colonial presents a rare opportunity to create your dream home. Offering 2,944 square feet of living space, with high ceilings & oak hardwood flooring. This classic residence has been lovingly enjoyed & maintained by one family and proudly showcases

  Kim Covino Compass

  143 Arlington St, Winchester, MA 01890
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  /20

  $675,000

  • 2 Beds
  • 1.5 Baths
  • 1,190 Sq Ft

  60 Lake St Unit E, Winchester, MA 01890

  Enjoy Winchester living in this spacious 2-bed, 1.5-bath townhouse at the desirable Wedge Pond Condominium. The main level features hardwood floors, a sunny living room, dining room, half bath, and kitchen. On the second level, you have two bedrooms and a full bath. The finished lower level offers more space for a family room, home office, or guest bedroom, plus laundry and storage. To top it all

  Shaundize Moosavizadeh Coldwell Banker Realty - Boston

  60 Lake St Unit E, Winchester, MA 01890
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  /41

  $3,200,000

  • 8 Beds
  • 6.5 Baths
  • 5,750 Sq Ft

  30 Willowdale Rd, Winchester, MA 01890

  A rare expression of quality, craftsmanship, and enduring style, 30 Willowdale Road presents an exceptional opportunity to own a newly constructed residence in one of Winchester’s most coveted neighborhoods. Set on a beautifully proportioned, large and level lot, this remarkable home has been thoughtfully conceived to offer the space, sophistication, and effortless lifestyle expected of a truly

  Nancy Pallotta Gibson Sotheby's International Realty

  30 Willowdale Rd, Winchester, MA 01890
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  /42

  $1,075,000

  $150K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  53 Lake St, Winchester, MA 01890

  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

  53 Lake St, Winchester, MA 01890
• 

  

  /30

  $349,900

  $15K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 613 Sq Ft

  200 Swanton St Unit 717, Winchester, MA 01890

  Rarely available top-floor (7th floor) condo at the Parkview Condominium Complex! Enjoy easy living in highly desirable Winchester. Well-maintained 1-bedroom condo offers a bright, open-layout, spacious bedroom with an oversized closet. Full bathroom with tiled shower/tub. The Kitchen offers ample cabinet and counter-top space, breakfast bar style which opens to the living area- perfect for

  Cameron Moniz Coldwell Banker Realty - Lexington

  200 Swanton St Unit 717, Winchester, MA 01890

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