Winchester, MA Homes for Sale with Garage

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  $974,900

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

  258 Cross St, Winchester, MA 01890

  Looking for a quiet retreat, with a SIDE STREET DRIVEWAY, built in privacy but still connected to the urban hustle and bustle of Boston metro? A rare Winchester opportunity, has arrived, priced comfortably under $1M. 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2.5 bath Colonial

  

  Justin Blankenship

  Fiv Realty Co

  258 Cross St, Winchester, MA 01890
• Explore Winchester

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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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  $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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  /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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  $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

  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, dining, and relaxing. The main level also includes formal

  Kim Covino Compass

  4 Churchill Rd, Winchester, MA 01890
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  /37

  $3,299,000

  $100K PRICE DROP

  • 7 Beds
  • 7.5 Baths
  • 7,226 Sq Ft

  1 Plymouth Rd, Winchester, MA 01890

  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

  1 Plymouth Rd, Winchester, MA 01890
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  /41

  $1,899,000

  • 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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  $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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  $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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  $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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  $975,000

  • 4 Beds
  • 3 Baths
  • 2,475 Sq Ft

  199 Washington St, Winchester, MA 01890

  Enjoy being just a few blocks from Winchester Center in this spacious condo with unique separate guest suite or home office. This single family alternative features 3 bedrooms on the main level and a fourth tucked away in the back of the second floor along with a 3rd bath and kitchenette. Come in the back door from the 1-car garage, or 3 parkings spaces in the driveway, straight into the large,

  Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

  199 Washington St, Winchester, MA 01890
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  $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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  $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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  $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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  $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

  $950,000

  • 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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  $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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  $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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  $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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  /40

  $1,299,000

  • 4 Beds
  • 1.5 Baths
  • 3,307 Sq Ft

  253 Pond St, Winchester, MA 01890

  Custom-built and thoughtfully designed for comfortable one-level living, this spacious ranch offers a flexible floor plan, ample living spaces, and convenient access to the walking trails and recreational amenities of nearby Horn Pond. The main level features a gracious formal living room with a wood-burning fireplace, an elegant dining room with custom paneling, and an updated eat-in kitchen

  Pirani & Wile Group Gibson Sotheby's International Realty

  253 Pond St, Winchester, MA 01890
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  $2,249,000

  • 5 Beds
  • 3.5 Baths
  • 4,368 Sq Ft

  11 Locke St, Winchester, MA 01890

  Built in 2021, this stunning home is ready for its next owners to enjoy. Its elevated setting provides a peaceful retreat with multiple areas for outdoor living, including a charming front porch. Inside, thoughtful design and exceptional attention to detail are evident throughout. The expansive open-concept kitchen, living and dining areas offer an ideal setting for entertaining, complemented by

  Lesley Smith Barrett Sotheby's International Realty

  11 Locke St, Winchester, MA 01890
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  $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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  $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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  $1,599,000

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

  143 Arlington St, Winchester, MA 01890

  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 timeless architectural character, generously

  Kim Covino Compass

  143 Arlington St, Winchester, MA 01890
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  $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
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  /42

  $1,549,000

  • 3 Beds
  • 2.5 Baths
  • 2,640 Sq Ft

  50 Holland St, Winchester, MA 01890

  Resort living just steps from the town center! Completely remodeled with custom finishes throughout, this stunning expanded cape with 3 levels, 3/4 bedrooms, 2.5-baths will exceed your expectations. The first floor features a spacious bedroom w/ full bath, an inviting living room w/ beautiful fireplace surrounded & custom built-ins, while the chef's kitchen is designed to impress with high end

  Kim Covino Compass

  50 Holland St, Winchester, MA 01890
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  /42

  $3,295,000

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

  2 Atherton Rd, Winchester, MA 01890

  Introducing 2 Atherton Road, an exceptional new construction residence offering over 6,100 sq. ft. of beautifully designed living space with 6 bedrooms, 6.5 baths, and a 3-car garage. A dramatic entry with soaring ceilings and a striking staircase sets the tone for the home’s sophisticated interiors. Designed for both everyday living and entertaining, the open-concept main level showcases an

  Peter Kasseris Serhant

  2 Atherton Rd, Winchester, MA 01890
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  $1,329,000

  $171K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,459 Sq Ft

  110 Thornberry Rd, Winchester, MA 01890

  110 Thornberry Road. Strong west side location near Vinson-Owen Elementary School and the Winchester Swim & Tennis Club. An exceptional opportunity to establish roots in Winchester. 2021 Natural Gas Brute FT Floor Standing Boiler. Replacement windows. Central cooling. 200 amp electric. Updated Kitchen w Double oven. Prefinished hardwood floors. Therma-Tru French doors flow from the dining room to

  Mark Kiklis Kiklis Real Estate, LLC

  110 Thornberry Rd, Winchester, MA 01890
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  $2,499,000

  • 4 Beds
  • 4.5 Baths
  • 4,450 Sq Ft

  54 Squire Rd, Winchester, MA 01890

  Introducing 54 Squire Road,an exceptional newer Colonial privately sited within one of Winchester’s most desirable enclaves.Set on a beautifully landscaped, wooded lot, this sun-filled residence blends timeless architecture with numerous substantial owner upgrades.Highlights include 9’ ceilings, elegant millwork,a designer chef’s kitchen with premium appliances,an impressive family room with

  Anthony Marino The Marino Group Collection

  54 Squire Rd, Winchester, MA 01890
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  $2,049,000

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

  26 N Gateway, Winchester, MA 01890

  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

  26 N Gateway, Winchester, MA 01890
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  $1,050,000

  • 5 Beds
  • 2.5 Baths
  • 2,801 Sq Ft

  257 Cross St, Winchester, MA 01890

  Situated on a large,10k+ level corner lot with frontage on both Cross Street and Verplast Avenue! The upper level features a fireplaced living room w picture window, updated kitchen, three bedrooms, 1.5 baths, and a large sunroom overlooking the expansive backyard. The first level offers additional flexible living space with a kitchenette, living area, two bedrooms, laundry, and a full bath,

  Kim Covino Compass

  257 Cross St, Winchester, MA 01890
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  $2,195,000

  $104K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 5,006 Sq Ft

  276 High St, Winchester, MA 01890

  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

  276 High St, Winchester, MA 01890
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  $1,110,000

  $40K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,186 Sq Ft

  63-65 Harvard St, Winchester, MA 01890

  Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home.

  Beth Sager Group Keller Williams Realty Boston Northwest

  63-65 Harvard St, Winchester, MA 01890
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  $3,600,000

  • 7 Beds
  • 7.5 Baths
  • 7,429 Sq Ft

  11 Viking Rd, Winchester, MA 01890

  Spectacular ground-up NEW construction estate on expansive, large level lot of 24,688sf, ready for move in, located on a quiet Winchester cul-de-sac. Newly completed, this exceptional residence spans more than 7,000 square feet across impeccably finished levels. Ideally positioned on a quiet cul-de-sac on over half an acre of land in one of Winchester’s most desirable locations, the home offers

  Valerie Post Engel & Volkers Boston

  11 Viking Rd, Winchester, MA 01890
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  /37

  $2,400,000

  $100K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 4,071 Sq Ft

  9 Plymouth Rd, Winchester, MA 01890

  Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for

  Stephanie Crawford Real Broker MA, LLC

  9 Plymouth Rd, Winchester, MA 01890
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  /42

  $3,100,000

  • 5 Beds
  • 5.5 Baths
  • 5,600 Sq Ft

  22 Oldham Rd, Arlington, MA 02474

  Elegantly positioned in Arlington's desirable Morningside neighborhood, this custom build luxury colonial offers over 5600 sf of refined living space on a beautifully landscaped lot. This recently built home features 5 bedrooms,5 full and 1 half bath. A grand two-story living room filled with natural light creates a dramatic centerpiece, while the chef's kitchen is equipped with premium Thermador

  Kathleen Lyons Century 21 North East

  22 Oldham Rd, Arlington, MA 02474
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  /42

  $2,950,000

  • 6 Beds
  • 5.5 Baths
  • 5,550 Sq Ft

  23 Lantern Ln, Arlington, MA 02474

  Stunning new-construction home set on a winding hillside street in Arlington's sought-after Morningside neighborhood. Designed for flexible modern living, this 6-bedroom residence features a serene second-floor primary suite plus a complete first-floor suite with its own private entrance — a self-contained space offering exceptional versatility. Two dedicated offices, one on each level, make

  Plato Asadov Steve Bremis Realty Group

  23 Lantern Ln, Arlington, MA 02474

Showing Results 1 - 40, Page 1 of 2