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Homes for Sale Winchester MA

Browse current homes for sale in Winchester MA. Contact Barrett Sotheby's International Realty or call our Winchester office directly at 781-729-7900 with any questions or to schedule a viewing. Register on the site to save your favorite listings and to receive email notifications when similar listings come to market.

Winchester, Massachusetts is 8 miles north of Boston. Winchester is child-friendly and home to lakes, parks, and trails. Winchester keeps its public spaces well maintained. Winchester is a family-friendly bedroom community. 

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16 Bellevue Avenue Winchester MA 01890

Winchester, MA16 Bellevue Avenue

Price$1,099,000

Est. Mortgage: $/month

MLS Number 73042012

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,791
  • High School Winchester High

Welcome to this charming multi-level home nestled on a generous corner lot, in a desirable Winchester neighborhood. The newly remodeled contemporary kitchen showcases white cabinets, granite countertops, tasteful backsplash, new stainless appliances, tile flooring, and recessed lighting. This bright & sunny home offers 3 bedrooms, 1.5 baths, fireplaced living room, inviting dining room, hardwood floors, lower level family room with fireplace, heated sunroom with skylights and exterior access, and an over-sized mud room with direct access to the 1-car attached garage. Move right in and enjoy as-is or bring your expansion ideas, with neighborhood value well supported by surrounding high-end newer homes. Live in the highly-rated Muraco school district, close to the Fells conservation area with acres of hiking, biking and walking trails, with easy access to highways (Rt-93 and Rt-95) for a convenient commute, and enjoy all the perks of Winchester living. Welcome home!

Listed by Seeme Moreira of Coldwell Banker Realty - Winchester

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$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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93 Bacon Street Winchester MA 01890

Winchester, MA93 Bacon Street

Price$899,000

Est. Mortgage: $/month

MLS Number 73040884

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,763
  • High School Whs

Townhouse, also listed as MLS 73040882. One of two units. Charm and character, blended with modern sophistication. This home lives like a single family and makes you feel a bit like you're in Back Bay! This fabulous large townhouse has high ceilings, large rooms, and plenty of space to spread out and live! A spacious living room opens to a family room with a fireplace and covered porch. The formal dining room has wainscoting and a china cabinet. Like to cook? A big open kitchen offers cherry cabinets, an island, and lots of counter space. Upstairs, enjoy 4 bedrooms over 2 floors, including a huge primary bedroom with a sitting area and full bath. One car deeded garage, close proximity to the trains, schools, and town center. Plus there is a private yard! Being sold as is, some work is needed.

Listed by Nancy S. Pallotta of Leading Edge Real Estate

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%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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93 Bacon Street Winchester MA 01890

MLS Number 73040882

  • Condo
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,763
  • High School Whs

Charm and character, blended with modern sophistication. This home lives like a single family and makes you feel a bit like you're in Back Bay! This fabulous large townhouse has high ceilings, large rooms, and plenty of space to spread out and live! A spacious living room opens to a family room with a fireplace and covered porch. The formal dining room has wainscoting and a china cabinet. Like to cook? A big open kitchen offers cherry cabinets, an island, and lots of counter space! Upstairs, enjoy 4 bedrooms over 2 floors, including a huge primary bedroom with a sitting area and full bath. One car deeded garage, close proximity to the trains, schools, and town center. Plus there is a private yard! Being sold as is, some work is needed.

Listed by Nancy S. Pallotta of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4 Rangeley Road Winchester MA 01890

Winchester, MA4 Rangeley Road

Price$1,299,000

Est. Mortgage: $/month

MLS Number 73038416

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,647
  • High School Winchester High

Prestigious 11 room brick family structure with au pair or in law suite, now a 2 family home. Easily restored home, reminiscent of a Back Bay brownstone. Multi-generational family can occupy or collect $75,600 annual income. A sun filled entrance leads to spacious elegant rooms, grand 10 ft ceilings captures the charm of this Queen Anne Victorian home, modern kitchen featuring classis tin ceiling, fireplaced dining room, mahogany beamed ceiling & spacious fireplaced living room featuring plaster moldings. Bedrooms (multiple closets) with full bath & half bath. Upper level boasts updated kitchen, large insulated windows, gleaming hardwood floors, Fireplaced sitting room and 3 or 4 bedrooms & 2 full baths, (master suite?). Separate enough to have privacy, but cohesive enough to feel like one space if preferred! It’s premier location adjacent to Winchester Center, Just inside the granite entrance pillars to Rangeley Estates. And don't forget your in-laws (or friends) to visit or stay.

Listed by Danielle Storella of Berkshire Hathaway HomeServices Commonwealth Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4 Rangeley Road Winchester MA 01890

Winchester, MA4 Rangeley Road

Price$1,299,000

Est. Mortgage: $/month

MLS Number 73038354

  • MultiFamily
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 3,647
  • Parking Spaces 6

Opportunity to own 1 of few TWO family homes in Winchester. Solid brick two family structure on large lot, admired by all who pass through Winchester center. Reminiscent of a Back Bay brownstone. Need room for an in law? A large blended family can occupy or take advantage of $75,600 potential income. Sun filled entrance leads to spacious elegant rooms with grand 10 ft ceilings. Unit 1: captures Queen Anne Victorian style home with modern kitchen featuring classic tin ceiling, fireplaced dining room has mahogany beamed ceiling & a spacious fireplaced living room featuring old world plaster moldings. Bedrooms with multiple closets and bath and a half. Unit 2: boasts an updated kitchen, large insulated vinyl windows, gleaming hardwood floors, Fireplace living room and 3-4 bedrooms & 2 baths, (master suite?) This home can function as two separate units or one multigenerational home. Located just inside the granite pillared gates to Rangeley Estates.

Listed by Danielle Storella of Berkshire Hathaway HomeServices Commonwealth Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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39 Everett Avenue Winchester MA 01890

Winchester, MA39 Everett Avenue

Price$2,300,000

Est. Mortgage: $/month

MLS Number 73037552

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 3,769
  • High School Winchester High

Welcome to 39 Everett Avenue, a classic mid-century modern home situated on a 25,000+ sf lot in the heart of Winchester’s coveted Everett Ave. neighborhood. Embrace the abundance of natural light streaming through the oversized windows throughout. This home exudes style & character with its impressive living room lined w/ built-in shelves, a wall of windows, brick fireplace, & wet bar. French doors lead directly to a side garden creating an organic flow of air & light. An eat-in kitchen w/ double sinks & plenty of storage opens to a lovely formal dining room w/ a large bay window. The 1st floor also boasts a spacious primary bedroom suite complete w/ a full bathroom, changing room, & three double closets. Two additional bedrooms, one and a half baths, and a home office, which opens up to an outside patio, complete this floor. The 2nd floor features two sun-filled bedrooms with hardwood floors, a full bath, and an enormous storage room with a walk-in cedar closet. It's a must-see home!

Listed by Paula R. Sughrue of Better Homes and Gardens Real Estate - The Shanahan Group

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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17 Brooks Street Winchester MA 01890

Winchester, MA17 Brooks Street

Price$2,995,000

Est. Mortgage: $/month

MLS Number 73033237

  • Residential
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 5,265

Unparalleled privacy ~ a tranquil retreat & a pristine neighborhood right at your fingertips! Imagine bedrooms w/window seats & a private deck connected to your primary suite all perched behind a canopy of trees. So much to love about a backyard reminiscent of a secret garden & the colors of every season showcased all around you.  A majestic estate, nestled in a private cul-de-sac; preserved in history, grace & craftsmanship, accented by tasteful details - an inviting foyer, soaring ceilings, 6 FPL, spacious interior rooms bathed in natural light & windows that frame the lush landscape of mature oaks & Japanese maples! The 2013 expanded chef's kitchen w/Wolf Stove, SubZero Fridge, Miele Convection/Micro, Kit/Fam & 4 season sunroom seamlessly connect to the patio. Freshly detailed exterior, painted in the soft warmth of Edgecomb Grey. Like stepping into a storybook only better b/c it's right here and ready to usher in new owners after ~30 yrs.  Simply an elegant way to redefine home!

Listed by Michaela Pixie Mahtani of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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14 Nassau Drive Winchester MA 01890

Winchester, MA14 Nassau Drive

Price$2,499,000

Est. Mortgage: $/month

MLS Number 73032962

  • Residential
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 5,268
  • High School Whs

Stunning 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 room and dining maintain its good sense of typical New England Colonial style, curved front stair case add one more layer of beauty. Second floor and third floor offer total 6 bedrooms, suites and walk-in closets. Master bedroom is with cathedral ceilings and a sprawling master closet. Smooth flow of the spacious and walk out lower level enables rich life style with billiard room, media room, art room and exercise room -- all designed for a modern lifestyle, with an open layout that is perfect for entertaining. State of the art systems with total 6 heating and cooling zones and central vacuum system.

Listed by Weidong Li of WINN Real Estate & Consulting

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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107 Sylvester Avenue Winchester MA 01890

Winchester, MA107 Sylvester Avenue

Price$974,900

Est. Mortgage: $/month

MLS Number 73032684

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,979
  • High School Winchester High

Get ready to F-A-L-L in love! Boasting 3 bedrooms and 2 full bathrooms and a multitude of updates, this home may be the one for YOU! French doors will greet you upon entering and lead you to the living room. From there you will find a designated home office (or playroom) and formal dining room with built-ins. The kitchen features granite counters, stainless appliances, and is highlighted by Nantucket bead-board. Off the kitchen is easy access to the lovely rear deck. The second level is home to all 3 bedrooms, and full bathroom #1. Now let’s head downstairs! This gorgeously renovated space offers bathroom #2, laundry room, and cozy family room! The plumbing, heating, cooling, and electrical have all been updated at 107 Sylvester. There is literally nothing left to do but move in! Enjoy all that Winchester has to offer including our top rated schools, 2 commuter rail stations, AND our beautiful Town Center!

Listed by Vita Realty Group and Philip J. Vita of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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43 Tremont Street Winchester MA 01890

MLS Number 73032286

  • Condo
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,756
  • High School Winchester High

Energy-efficient home with low maintenance fee and friendly neighborhood. This bright home featuring 4 bedrooms, 3 full baths, office and enormous family room. The 1st floor highlights modern open concept Living &Dining room, a gourmet kitchen with granite counters, soft close custom cabinets, stainless steel appliances. 3 Bedrooms and 2 bathrooms on this level as well. The walkout lower level offers additional bedroom with another full bath. Plenty of space for family room, office, home theater and play area for kids. Gleaming hardwood floors throughout, high ceilings, central air, custom wainscoting, built-ins, recessed LED lighting, gas fireplace, washer/dryer. Features 2 grand master suites with en-suite master baths and walk in closet. 1 car garage and additional off street parking. Conveniently located in a desirable neighborhood on a dead-end street, minutes-walking distance to both elementary and high schools, shopping, commuter rail and downtown Winchester.

Listed by Yanling Zeng of Quintess Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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17 Lochwan Street Winchester MA 01890

Winchester, MA17 Lochwan Street

Price$1,988,000

Est. Mortgage: $/month

MLS Number 73029533

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3,293
  • High School Wps

Amazing home built in 2015 on a quiet dead-end street, this 4 bedroom, 2.5 bathroom home has over 3293 sf of living area, and an attached 2 car garage. Elegant foyer with high ceilings leads to sunny living room and dinning room with large windows; On the 1st floor, the kitchen flows into the FR with gas fireplace. Open floor plan kitchen with granite island & countertops, vented gas stove & all S+S appliances. You can see the hardwood floors throughout the house. On the 2nd level, a Master suite with walk-in closets and bathroom with a stand-up shower and a tub with jets. 3 other spacious bedrooms, a convenient laundry room with a build-in sink, and an office complete the 2nd floor. A slider door on the 1st floor breakfast area leads to the deck overseeing the fenced backyard. Property has underground lawn irrigation to help maintain the exterior of this gorgeous home! Big potential with the walk-up 3rd floor and basement with 3 big egress windows finished. 17 Lochwan is a must see!

Listed by Yan Rong of United Real Estate,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2 Reservoir Street Winchester MA 01890

Winchester, MA2 Reservoir Street

Price$1,990,000

Est. Mortgage: $/month

MLS Number 73027354

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,267
  • High School Whs

Elegant & spacious new construction in one of Winchester’s coveted neighborhoods situated steps from the Middlesex Fells Reservation, minutes from downtown Boston & within close proximity to town center, commuter rail & schools. If you like open concept living, high end design elements & incredible architectural details, then look no more, this is the home for you. The developer has carefully designed the house with everything in mind for today’s lifestyle & ease of living. The 1st floor has an open concept layout perfect for entertaining, a gourmet chef's kitchen, formal dining, living room with fireplace, mudroom & powder room. The 2nd floor offers a primary suite with a luxurious bathroom & walk-in closet with custom cabinetry. A 2nd ensuite, 2 more bedrooms, laundry room & full bath complete this level. The 3rd level has another bedroom & bonus room. The lower level is the perfect space for a gym, playroom or family room. Offers a spacious yard with landscaped grassy areas & patio.

Listed by Pirani & Wile Group and Julie Wile Fish of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Nov 23, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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