Homes for Sale in 01890

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  /41

  $1,990,000

  • 4 Beds
  • 4.5 Baths
  • 4,474 Sq Ft

  4 Chestnut St, Winchester, MA 01890

  Space to grow, room to gather, and a location that feels like home. Just blocks from Winchester’s town center, commuter rail, and nearby schools, this warm and distinctive home offers four levels of flexible living. A vaulted-ceiling living room sets the tone, while the custom kitchen features blue cabinetry, copper accents, and bold designer touches. One bedroom opens to a composite deck

  

  Tyson Lynch

  The Proper Nest Real Estate

  (781) 633-6582

  4 Chestnut St, Winchester, MA 01890
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  /42

  $2,975,000

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

  54 Wedgemere Ave, Winchester, MA 01890

  Exceptional value, prime living in this stunning home w/ spectacular resort style back yard surrounded by mature plants and trees encompassing the gorgeous yard/setting. Completely updated throughout w/ custom high end finishes, open floor plan, wonderful chefs kitchen w/ Sub Zero- Wolf appliances, sunny breakfast/dining area w/ a wall of windows overlooking expansive backyard featuring gorgeous

  Kim Covino Compass

  54 Wedgemere Ave, Winchester, MA 01890
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  /42

  $3,499,000

  • 5 Beds
  • 7 Baths
  • 7,101 Sq Ft

  257 High St, Winchester, MA 01890

  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

  257 High St, Winchester, MA 01890
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  /42

  $2,399,000

  • 6 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  14 Grant Rd, Winchester, MA 01890

  Welcome to 14 Grant Road – a stunning new construction home offering spacious, open-concept living in one of Winchester’s most desirable neighborhoods. Designed for modern lifestyles, this home features a chef’s kitchen that flows seamlessly into the dining and living areas, creating the perfect space for entertaining and everyday living. A sun-drenched 3-season porch expands your living space

  Monte Marrocco Coldwell Banker Realty - Lexington

  14 Grant Rd, Winchester, MA 01890
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  /40

  $2,999,999

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

  6 Abby Rd, Winchester, MA 01890

  Here's a rare opportunity to own a spectacular new construction home by a premier local builder on a BRAND-NEW road. This property stands prominently on its lot, overlooking a lush wooded area with close proximity to “The Fells”. The first floor is designed for both entertaining and everyday living, featuring formal dining, a designer kitchen with a butler's pantry, and a fireplaced family room

  Philip Vita Compass

  6 Abby Rd, Winchester, MA 01890
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  /36

  $3,600,000

  • 6 Beds
  • 7 Baths
  • 8,866 Sq Ft

  20 Amberwood Dr, Winchester, MA 01890

  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

  20 Amberwood Dr, Winchester, MA 01890
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  /40

  $2,199,000

  • 5 Beds
  • 3.5 Baths
  • 6,232 Sq Ft

  5 Azalea Rd, Winchester, MA 01890

  NEW PRICE! RENOVATIONS & UPDATES JUST COMPLETED THROUGHOUT! 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

  Giordana Fiorvanti-Smith Berkshire Hathaway HomeServices Commonwealth Real Estate

  5 Azalea Rd, Winchester, MA 01890
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  /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
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  /42

  $2,689,000

  • 6 Beds
  • 5.5 Baths
  • 4,563 Sq Ft

  382 S Border Rd, Winchester, MA 01890

  NEW HIGH-END CONSTRUCTION - 12 Rms - 6 BD's - 5.5 BA's You will be captivated by the grand entrance - attention to detail - high coffered 10' ceilings and excellent flow that leads you to the magnificent Open Floor Plan - custom-designed Kitchen which is the heart of this home. no expense was spared; custom Cabinets, Thermador appliances, oversized Center Island; Living Rm/Great Rm w/FP, Dining

  Lucille Murray Advisors Living - Winchester

  382 S Border Rd, Winchester, MA 01890
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  /42

  $2,245,000

  • 6 Beds
  • 4 Baths
  • 4,385 Sq Ft

  5 Bacon St, Winchester, MA 01890

  This stunning Victorian home, in the style of Painted Ladies with soaring ceilings & hardwood floors, is in a prime neighborhood just moments from Winchester Center, the commuter rail, Shannon Beach, & a short ride to the Airport & downtown Boston. The house lives as a harmonious single family with an inlaw apartment on the 1st floor. It has 6 beds & 4 baths, over 4,385 SF of living area on 3

  Anne Spry Barrett Sotheby's International Realty

  5 Bacon St, Winchester, MA 01890
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  /38

  $2,350,000

  • 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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  /27

  $2,239,000

  • 5 Beds
  • 4.5 Baths
  • 4,798 Sq Ft

  61 Grove St, Winchester, MA 01890

  - 2017 - STUNNING CUSTOM- BUILT HOME, COMPLETELY rebuilt and doubled in size with bright and sunny rooms and a flexible floor plan. Welcome to this easy living, maintenance free sophisticated residence. FIRST FLOOR LUXURIOUS SUITE with a LARGE BEDROOM, marble bath w/double sink vanity, walk in shower & soaking tub. An exquisite kitchen with granite island, counters and back splash, All Bosch

  Dorothea Feffer Coldwell Banker Realty - Lexington

  61 Grove St, Winchester, MA 01890
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  /40

  $2,195,000

  • 6 Beds
  • 5.5 Baths
  • 5,791 Sq Ft

  58 Bacon St, Winchester, MA 01890

  Timeless elegance spans four meticulously finished levels with 15 rooms, 6 bedrooms and 5+ bathrooms(2 en-suite). Living room flows seamlessly into a sunroom for a perfect retreat. The dining room opens to a covered porch with a gas line for the grill. New, top shelf, chef’s kitchen with all the bells & whistles and open to the family room. Thoughtfully designed for convenience, an elevator from

  Real Estate Advisors Group Coldwell Banker Realty - Belmont

  58 Bacon St, Winchester, MA 01890
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  /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
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  /38

  $2,399,000 New Construction

  • 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
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  /30

  $875,000

  • 3 Beds
  • 2.5 Baths
  • 1,843 Sq Ft

  171 Swanton St Unit 5, Winchester, MA 01890

  Charming townhouse located at The Village, one of Winchester’s most sought-after and impeccably maintained communities, offers 1,843sf of living space. Featuring 3 generously sized bedrooms with full-height ceilings, and 2.5 updated bathrooms, it is one of the largest homes in the community. The home is flooded with natural light thanks to its end-unit position, windows on three sides, and a

  Jonathan Radford Coldwell Banker Realty - Boston

  171 Swanton St Unit 5, Winchester, MA 01890
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  /37

  $1,649,000

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

  166 Forest St, Winchester, MA 01890

  Tucked away on a picturesque street, this beautifully maintained Colonial offers 4 levels of thoughtfully designed living space. The open-concept main floor features a sun-filled living room with vaulted ceilings, skylights, gas fireplace, and an adjacent dining area. The gourmet kitchen boasts stainless steel appliances, breakfast bar, built-in desk, and sliders leading to a private deck. A

  Ning Sun United Real Estate, LLC

  166 Forest St, Winchester, MA 01890
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  /23

  $1,050,000

  • 4 Beds
  • 2 Baths
  • 1,938 Sq Ft

  380 Cross St, Winchester, MA 01890

  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

  380 Cross St, Winchester, MA 01890
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  /42

  $1,550,000

  • 5 Beds
  • 3 Baths
  • 2,995 Sq Ft

  205 Ridge St, Winchester, MA 01890

  Welcome to 205 Ridge Street, a stunning residence that blends timeless elegance with modern comfort, perfectly designed for today’s lifestyle. Nestled in one of Winchester’s most desirable neighborhoods, this five-bedroom, three-bath home offers the perfect balance of refined living and everyday convenience. From the moment you arrive, the property’s curb appeal and thoughtful details set the

  Debby Valdes eXp Realty

  205 Ridge St, Winchester, MA 01890
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  /23

  $999,999

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft

  16 Park Ave Unit 1, Winchester, MA 01890

  Breathtaking luxury condo just moments from Winchester Center and the commuter rail. This recently updated home offers bright, spacious, one-level living with hardwood floors and custom shutters throughout. The kitchen features quartz countertops, stainless steel appliances–including GE Cafe range and microwave, an oversized sink, and large peninsula with ample seating flows seamlessly to the

  Andrea Mackey Barrett Sotheby's International Realty

  16 Park Ave Unit 1, Winchester, MA 01890
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  /36

  $959,000

  • 3 Beds
  • 1 Bath
  • 1,425 Sq Ft

  571 Washington St, Winchester, MA 01890

  Step into this charming 3-bedroom home that radiates warmth and character from the moment you arrive. Designed with light-filled living spaces and three generously sized bedrooms, it’s a perfect fit for today’s lifestyle just moments from Winchester Center, award-winning schools, and the commuter rail. The fenced backyard and expansive patio extend your living space outdoors, creating a private

  Ryan Wilson Keller Williams Realty

  571 Washington St, Winchester, MA 01890
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  /31

  $1,599,000

  • 5 Beds
  • 3.5 Baths
  • 2,718 Sq Ft

  77 Washington St, Winchester, MA 01890

  This isn’t just a house — it’s a front-row seat to the good life, where you can walk to shops, schools, cafes, restaurants, and everything the town has to offer! This 5-bedroom, 3.5-bath Victorian sits proudly in the heart of Winchester Center, in the highly coveted Lincoln School district. Original hardwood floors, soaring ceilings, and stunning architectural details give this home its timeless

  Nancy Pallotta Advisors Living - Winchester

  77 Washington St, Winchester, MA 01890
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  /42

  $409,900

  • 1 Bed
  • 1 Bath
  • 634 Sq Ft

  200 Swanton St Unit T11, Winchester, MA 01890

  Move right into this immaculate, renovated walk-in condo with an oversized layout and a highly sought-after private terrace patio. Terrace units rarely go on the market—don’t miss this opportunity to purchase a unit in the best location in the building. The sun-filled home offers an eat-in kitchen with granite counters, modern cabinets, newer stainless-steel appliances, and a dining area

  Shannon Jenkins RE/MAX Realty Experts

  200 Swanton St Unit T11, Winchester, MA 01890
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  /41

  $1,950,000

  • 4 Beds
  • 4.5 Baths
  • 3,512 Sq Ft

  7 Wainwright Rd Unit 72, Winchester, MA 01890

  Extensively renovated and move-in ready, this stunning F-unit townhouse offers 4 bedrooms and 4.5 baths with impeccable detail and modern appeal throughout. The many windows, high ceilings, gleaming hardwood floors, and open design create a warm sun-filled home. You will enjoy the large kitchen and the ability to retreat to the dazzling first-floor primary suite, which provides single floor

  Pirani & Wile Group Advisors Living - Winchester

  7 Wainwright Rd Unit 72, Winchester, MA 01890
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  /41

  $1,125,000

  • 3 Beds
  • 2.5 Baths
  • 2,648 Sq Ft

  89 Main St, Winchester, MA 01890

  Welcome to this charming Cape on a spacious corner lot in Winchester. The main level offers hardwood floors, a front-to-back living room with fireplace and built-ins, a dining room with corner hutch, and a half bath. The kitchen features granite counters, stainless steel appliances, abundant cabinetry, and a breakfast island that opens to the cathedral-ceiling family room. A side entry with

  Andersen Group Realty Keller Williams Realty Boston Northwest

  89 Main St, Winchester, MA 01890
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  /41

  $4,174,000

  • 7 Beds
  • 6 Baths
  • 7,043 Sq Ft

  2 Everett Ave, Winchester, MA 01890

  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

  2 Everett Ave, Winchester, MA 01890
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  /25

  $662,500

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  2 George Rd Unit 2, Winchester, MA 01890

  Presenting a charming 3- Bedrooms ,2 - Baths home at The Residences at Winchester featuring gleaming hardwood floors, freshly painted interior and updated lower level with brand new flooring. This move-in-ready has comfort , and functionality across all levels. The first floor includes bright Living room ,a dedicated dining room and an updated kitchen with granite countertops and stainless

  Rajive Dogra Coldwell Banker Realty - Lexington

  2 George Rd Unit 2, Winchester, MA 01890
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  /39

  $2,750,000

  • 5 Beds
  • 3.5 Baths
  • 4,779 Sq Ft

  48 Salisbury St, Winchester, MA 01890

  Thoughtfully renovated & meticulously maintained, this classic colonial home in the Flats invites with timeless charm & modern conveniences. Through the center entrance be welcomed into the fireplaced living room & dining room- both refreshed in 2025 with new lighting, paint & wallpaper. The open-plan custom kitchen with marble counters, stainless appliances, and a butler’s pantry with sink,

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

  48 Salisbury St, Winchester, MA 01890
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  /41

  $2,849,000

  • 5 Beds
  • 5.5 Baths
  • 4,627 Sq Ft

  11 Taft Dr, Winchester, MA 01890

  Luxury, location, and lifestyle come together in this beautiful new 5-bed, 5.5-bath home in Winchester’s sought-after Westside. Just steps to Ambrose School, one block from the Alewife bus stop, a short stroll to the commuter rail, and right down the street from the Winchester Boat Club, this home offers unmatched convenience and charm. Inside, enjoy over 4,600 sq. ft. of thoughtfully designed

  Rose Hall Blue Ocean Realty, LLC

  11 Taft Dr, Winchester, MA 01890
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  /42

  $2,099,000

  • 6 Beds
  • 3.5 Baths
  • 3,521 Sq Ft

  19 Glengarry Rd, Winchester, MA 01890

  A truly special opportunity to own a home in one of Winchester’s most desirable neighborhoods, just outside the vibrant town center! Welcome to 19 Glengarry Road~ this character-filled residence offers the perfect blend of charm, warmth & potential, making it ideal for buyers looking to personalize & create their dream home. Nestled in a top neighborhood near wedge pond, the home boasts classic

  Kim Covino Compass

  19 Glengarry Rd, Winchester, MA 01890
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  /35

  $1,379,000

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

  7 Thornberry Rd, Winchester, MA 01890

  Priced to SELL this newly renovated contemporary home, nestled in a highly sought-after West-side neighborhood with surprising space! This 3+ level home boasts 4-5 spacious bedrooms and 2 full stylish baths, this home offers versatile space for multiple home offices, in law/ au-pair space plus comfortable family spaces all great for entertaining. The main level features a beautiful open-concept

  Kim Covino Compass

  7 Thornberry Rd, Winchester, MA 01890
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  /42

  $3,989,000

  • 6 Beds
  • 7.5 Baths
  • 7,330 Sq Ft

  6 Ledgewood Rd, Winchester, MA 01890

  Majestic 6 BR, 7.5 BA w/ 3 car garage! Custom home in one of Winchesters most sought after neighborhoods. From the moment you step inside, you will feel the unsurpassed quality of this grand home built by top local builder. A welcoming wrap-around front porch & foyer flow into the formal dining room & into the beautiful oversized family room. The stunning eat in kitchen boasts custom cabinetry,

  Kim Covino Compass

  6 Ledgewood Rd, Winchester, MA 01890
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  /24

  $1,249,900

  • 3 Beds
  • 2.5 Baths
  • 2,458 Sq Ft

  59 Johnson Rd, Winchester, MA 01890

  Welcome to this stunning updt’d 3-bed, 2.5-bath multi-level home in one of Winchester’s most desirable neighborhoods, just two blocks to Vinson-Owen Elementary! Freshly painted inside&out for a modern, crisp feel, the home offers a perfect blend of style, comfort, convenience. Open layout with a beautiful fireplace, living room, bay windows, and formal dining room lead to a spacious deck and

  Angela Zhang Greatland Real Estate LLC

  59 Johnson Rd, Winchester, MA 01890
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  /42

  $1,275,000

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

  162 Swanton St Unit 162, Winchester, MA 01890

  NEW CONSTRUCTION!! Welcome to this meticulously crafted, modern townhouse END UNIT offering over 2,100 sq ft of thoughtfully designed living space. The open-concept main level features gorgeous mill work, gleaming hardwood floors, a cozy fireplace & sleek chef-inspired kitchen w/ stainless appliances, large center island & an adjacent mudroom w/ half bath perfect for today’s lifestyle. The 2nd

  Kim Covino Compass

  162 Swanton St Unit 162, Winchester, MA 01890
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  /30

  $1,500,000

  • 4 Beds
  • 2.5 Baths
  • 2,765 Sq Ft

  7 Sherman Place, Winchester, MA 01890

  Welcome to a sun-filled, newly renovated 4-bedroom,2.5-bath luxury residence nestled on a cul-de-sac w/ private garden! This is a 2,760 SF townhome, living like a free-standing home & offering a thoughtful layout ideal for living & entertaining. Standout features: 9-ft ceilings, oversized windows & a state-of-the-art, eco-conscious, high-efficiency heat pump system. The first level: open concept

  Ides Figueiredo Coldwell Banker Realty - Brookline

  7 Sherman Place, Winchester, MA 01890
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  /42

  $3,199,000

  • 6 Beds
  • 6.5 Baths
  • 8,463 Sq Ft

  26 Swan Rd, Winchester, MA 01890

  Nestled in the heart of Myopia Hill, this custom-built home is sure to impress! Live your best life at 26 Swan Road offering 6 bedrooms, 6.5 bathrooms with 2 primary suite options! This magnificent residence boasts expansive living spaces, elevator & indoor pool! Exquisite craftsmanship is shown throughout this home including a newly renovated gourmet kitchen w/custom cherry cabinetry & high end

  Kim Covino Compass

  26 Swan Rd, Winchester, MA 01890
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  /16

  $1,075,000

  • 4 Beds
  • 3 Baths
  • 1,860 Sq Ft

  60 Harvard St, Winchester, MA 01890

  Exceptional investment opportunity. Located in the heart of desirable Winchester, this multi family property offers a rare opportunity to own a ready to renovate vacant building with incredible potential. Two 1 bedroom, 1 bathroom units and 1 two bedroom unit. This property is primed for a full renovation. Perfect for investors, end users or travellers looking for their own pied-a'-terre, while

  Mark Krasnyansky eXp Realty

  60 Harvard St, Winchester, MA 01890
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  /42

  $1,879,000

  • 5 Beds
  • 3.5 Baths
  • 3,294 Sq Ft

  20 Grove Place, Winchester, MA 01890

  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 Cafe 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

  20 Grove Place, Winchester, MA 01890
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  /42

  $1,729,000

  • 4 Beds
  • 5 Baths
  • 5,361 Sq Ft

  4 Aricia Ln, Winchester, MA 01890

  Rare 5-car garage on a quiet, tree-lined cul-de-sac in one of Winchester’s most exclusive enclaves! Offering both serene privacy and seamless connectivity, 4 Aricia is perfectly positioned within walking distance to a coveted elementary school and Wright-Locke Farm, and minutes from the commuter rail and Routes 128 & 93. Set on nearly .5 acres of manicured grounds, the home’s exterior is framed

  The McLaren D'Agostino Team Compass

  4 Aricia Ln, Winchester, MA 01890
• 

  

  /36

  $1,349,900

  • 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

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