Winchester Homes for Sale

Winchester, Massachusetts is a quiet, bedroom community conveniently located just 8 miles north of Boston. Winchester is home to several lakes and parks. Winchester is a family-friendly community that is home to several well-maintained parks, several lakes, and lots of trails.

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Browse all homes for sale in Winchester, Massachusetts below. Contact us to schedule a showing or if you have any questions. Create an account to save your favorite Winchester listings and to receive email notifications when similar properties become available. 

3 Cambridge Street Winchester MA 01890

Winchester, MA3 Cambridge Street

Price$2,999,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72619462

  • Single Family
  • Garage 2
  • Parking Spaces 8
  • Total Parking Spaces 10
  • MLS Status Contingent

WINCHESTER WATERFRONT!! Amazing opportunity to customize your dream home on spectacular oversized lot on upper Mystic Lake! This gorgeous home has been custom designed to maximize the view from every room offering an open first floor plan with panoramic views of the lake and distant views of the Boston Skyline! Top of the line kitchen, with designer cabinetry, oversized island, gas fireplace, 42' Wolfe stove and double ovens. Expansive family room with fireplace off kitchen with doors direct to 35' deck overlooking lake. This home features 2 master suites with full baths & walk-in closet; one on the first floor and the other on the second both with breathtaking water views and deck access. Master en-suite on second level features separate sitting area with french doors leading to balcony. Full walk-out lower level with additional unfinished space that can be finished and customized to include a gym, media space or anything your family desires.

Listed by Kim Covino of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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11 Lorena Road Winchester MA 01890

Winchester, MA11 Lorena Road

Price$2,945,000

Est. Mortgage: $/month

MLS Number 72628997

  • Single Family
  • Garage 2
  • Parking Spaces 5
  • Total Parking Spaces 7
  • MLS Status Active

Steeped in history, 11 Lorena Road features 7,549 square feet of living space & is a quintessential New England home in both setting & style. Originally designed by renowned architect Miles Standish, a 1960s addition by Richard Wills of the elite Royal Barry Wills architecture firm-featured in Life Magazine in both 1938 & 1946 for his classic Cape Cod & Colonial home designs-added an early American pub w/ beautiful pine-paneled walls, full bar, fireplace & abundant seating as well as a country living room. In 1999 Richard's son, also of RBW, added an updated kitchen, family room & second floor bedrooms. All of this is set on 1.5+ acres of terraced land w/ patio spaces, embedded mill stones & spectacular gardens with a number of rare & unusual plantings including a certified Dawn Redwood that is one of the oldest in the US & believed to be from the original batch of seeds brought to the US from China by the Arnold Arboretum. Additional details abound in this unique, special home!

Listed by Anne Spry and Lesley Smith of Waterfield Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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5 Wagon Wheel Road Winchester MA 01890

Winchester, MA5 Wagon Wheel Road

Price$2,670,000

Est. Mortgage: $/month

MLS Number 72625592

  • Single Family
  • Garage 3
  • Parking Spaces 12
  • Total Parking Spaces 15
  • MLS Status Active

A Must Have Is This Majestic Brick COLONIAL Home With A Heated Three Car Garage Attached To The House With Plenty of Parking For Guests Also. On Over An Acre of Beautiful Professionally Landscaped Flower Beds and Green Grass. it includes 7,097 Square Feet Of Living Space, Huge Heated Pool, Year Round 10 Person Spa. 14 Rooms, 6 Bedrooms, 6 Full Bathrooms, Finished Basement. When you Enter the New Elegant Double Front Door Will Welcome You Featuring A Family Room With A Fireplace, Formal Living Room, Dining Room, Office, And The Gorgeous Kitchen on the First Floor. To The Second Floor You Have A Private Master Bedroom Area With a Fireplace, Heated Tile Bathroom Floor , A Large Walk In Closet and A Reading Room. Three Large Bedrooms Complete the Second Floor Including Walk In Closets in Each One. The Third Floor Offers A Great Living Area For Visitors And An Additional Master Suite. Built in 2015 it still Looks Like Brand New. A Must See And Buy for the Family.

Listed by J D J Elite Team, Deborah Byrne, Jack Lister and Joanne Vanstry of Berkshire Hathaway HomeServices Verani Realty

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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9 Ginn Road Winchester MA 01890

Winchester, MA9 Ginn Road

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72633034

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Total Parking Spaces 8
  • MLS Status Active

Stunning Craftsman Colonial with a dreamy back yard in top neighborhood! Beautifully situated on one of the largest lots in the area, you will be proud to call this spectacular house your home! Gorgeous welcoming front porch with breathtaking entry, featuring a 180 gallon salt water fish tank, sleek designer kitchen w/ custom Bamboo cabinets, Lutron auto shades & LR w/stone/gas fireplace. Spacious 1st floor Master suite w/ spa like bath, soaking tub, walk in closet & sitting area w/ high ceilings & french doors to patio overlooking amazing back yard; outdoor entertaining at its finest! Offering a full kitchen with sink, fridge, built in gas grill w/ dining/ bar, TV and sun-setter auto.awning! Custom built w/top of the line everything, this home is a work of art with beautiful finishes and custom details throughout. 4/5 large bedrooms each w/ private baths,1st floor office, mudroom with lockers leads to 2 car garage, plus over 1200 sf add'l basement space avail for future game/media/gym

Listed by Kim Covino of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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 Myopia Road Winchester MA 01890

Winchester, MA39 Myopia Road

Price$2,349,000

Est. Mortgage: $/month

MLS Number 72574074

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Total Parking Spaces 12
  • MLS Status Active

If you are searching for privacy in a sought after enclave of Winchester this is the home for you. Large sunfilled 1st floor with a flexible floor plan. Enter into a gracious foyer with a dramatic curved staircase. The kitchen is open to family room with wide-planked hardwood floors. Huge 4 season sunroom w/ fireplace, Palladian windows and a series of glass french doors overlooking your private oasis & pool area. Formal living rm w/ marble fireplace. A sophisticated study w/ bay window & fireplace overlooking the back yard. Beautiful dining room perfect for entertaining large gatherings or intimate family meals. 2nd floor offers a private master bedroom suite w/ 4 additional bedrooms. Finished walk-out lower level w/ a large tiled bonus room, additional space for guest or au pair. Attached 2 car-garage. Close to Country Club, Boat Club & only 8 miles from Boston. Bring your design ideas and make this your forever home. House cannot be seen from street.

Listed by Leigh Ventura and David Hayes of Coldwell Banker Residential Brokerage - Winchester

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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 Grove Street Winchester MA 01890

Winchester, MA43 Grove Street

Price$2,199,000

Est. Mortgage: $/month

MLS Number 72629238

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Active

NEW CONSTRUCTION! This exquisite 5 beds 4.5 bth colonial features open floor concept for today's family living! Thoughtfully designed with a high-end finishes & details, this homes offers an oversized 2-car garage, direct entry into mudroom, gourmet kitchen w/ island & high end appliances, FR with FP & direct exterior access , formal LR & DR with crown moldings & wainscoting. Second floor features include master suite w/ walk-in closets, luxurious master bath, laundry room with custom cabinetry and sink, 4 oversized corner bedrooms flooded with light & ample closet space. Third floor with bonus room, add'l bedroom & full bath. Great rear yard w/deck & sliders from kitchen. The lower level bonus space features spacious family room, full bath &-plenty of space for gym. Looking to build an in-ground pool? This home has the perfect setting and yard to accommodate all your backyard needs. Don't miss this opportunity to customize some interior finishes!

Listed by Kim Covino of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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54 Wedgemere Avenue Winchester MA 01890

Winchester, MA54 Wedgemere Avenue

Price$2,199,000

Est. Mortgage: $/month

MLS Number 72638671

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Active

Enjoy life in this gorgeous Wedgemere Avenue home with spectacular backyard retreat! Updated throughout with custom high end finishes, wonderful chefs kitchen with Sub Zero/ Wolf appliances, sunny breakfast/dining area with a wall of windows overlooking expansive back yard featuring gorgeous patio & maintenance free heated POOL with in- floor cleaning system and auto cover! Inviting covered rear porch / outdoor living room complete with flat screen TV just steps from pool and kitchen. Enormous family room with gas fireplace, built in bookshelves & great storage. Stylish formal dining room with custom wainscoting, window buffet & china cabinet, front to back LR w/ fplc; Grand rooms, detailed moldings, new windows, new baths, great master suite with 2 walk in closets, spa like bath with oversized shower and soaking tub. Full third floor with 3 rooms and full bath, updated heating system, central air, new roof. 2 car detached garage with office above completes this great home!

Listed by Kim Covino of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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5 Dean Road Winchester MA 01890

Winchester, MA5 Dean Road

Price$2,100,000

Est. Mortgage: $/month

MLS Number 72582583

  • Single Family
  • Garage 3
  • Parking Spaces 6
  • Total Parking Spaces 9
  • MLS Status Active

BEAUTIFUL NEW CONSTRUCTION in Winchester's Muraco school district, recognized by the state for its outstanding 2019 MCAS achievement! This STUNNING 6-bedroom, 5-bath home with approx. 6125 sq. ft. of living space offers extraordinary comfort for the entire family, and the details throughout are absolutely exquisite. The sun-filled main level boasts a grand two-story foyer, living & dining rooms, gorgeous high-end kitchen w/ elegant cabinetry, large family rm. w/ fireplace, sitting rm., office area, + a guest bdrm & full bath. Second level has 4 spacious bdrms., including a fabulous master en-suite w/ soaking tub, striking tile, his/her sinks, + jetted shower; there are 2 more full baths, and laundry. Lower level offers GREAT spaces; exercise rm., playroom, media room, mudroom, + bedroom & full bath. The top floor is +900 sq. ft. of unfinished storage space. There's a 3 car garage, + terrific level back yard. Welcome home!

Listed by Anne Spry and Jane Byrne of Waterfield Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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5 Fox Hunt Lane Winchester MA 01890

Winchester, MA5 Fox Hunt Lane

Price$2,050,000

Est. Mortgage: $/month

MLS Number 72633001

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Active

Understated and unique luxury. This traditional brick colonial opens into an interior of simple, contemporary beauty. Situated on 1.2 acres that border the 13th fairway of the Winchester Country Club, the home's 300-foot elevation affords sweeping views across the Mystic Lake and into East Boston. A large deck and patio invite outside entertaining. Inside, the home mixes traditional and contemporary elements: an expansive living room with custom Butternut woodwork and vaulted ceiling; a kitchen/family room with a gas fireplace; a TV and billiards room; a master bedroom suite with a fireplace and attached office/dressing room. The second floor features two ensuite bedrooms, plus options for additional bedrooms. The walk-out lower level includes an indoor pool, greenhouse, and a fourth bedroom with a separate entrance, bathroom, and sauna.

Listed by Cynthia Houle and Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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12 Priscilla Lane Winchester MA 01890

Winchester, MA12 Priscilla Lane

Price$1,899,000

Est. Mortgage: $/month

MLS Number 72561811

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Active

Beautiful NEW CONSTRUCTION Home on the East Side! Ready for occupancy late December/January~ This exquisite 5 bedroom 3.5 bath colonial features desirable open floor plan for today's family living! Thoughtfully designed with high-end finishes & details, this home offers an oversized 2-car garage, direct entry into mudroom, gourmet kitchen w/ island & Chefs appliances, family room with FP adjacent to kitchen & direct exterior access to patio. sun-drenched formal LR & DR with crown molding ~ Second floor features include master suite w/ double walk-in closets, luxurious master bath, laundry room with custom cabinetry and sink, 4 oversized corner bedrooms flooded with light & ample closet space. Third floor with bonus room/ add'l bedroom & full bath. Private rear yard w/ sliders from kitchen leading to patio. This home is located in sought after East side of town, convenient to the center, Lincoln school district, and great neighborhood!

Listed by Kim Covino of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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36 Dunster Lane Winchester MA 01890

Winchester, MA36 Dunster Lane

Price$1,789,000

Est. Mortgage: $/month

Open House

MLS Number 72640271

  • Single Family
  • Next Open House: Sun 5th 12:00 pm - 1:30 pm
  • Garage 2
  • Parking Spaces 2
  • Total Parking Spaces 4

Ultra high-end, NEW Farmhouse Colonial! Imagine finding your dream home, in the Blue Ribbon Award-Winning Vinson-Owen School District, that has room for the whole extended family! Finally, a luxury new construction option which is not only architecturally stunning with farmer's porch and stop-in-your-tracks curb appeal, but it does not disappoint once inside, as local quality builder has thought of every custom detail and amenity craved by today's buyers. Quartz & Soapstone counters; Thermador appliances; extra beverage fridge; Pella windows; security & irrigation systems; Nest thermostats; Ring video doorbell; full finished walk-out lower level with 2nd gas fireplace, sliders to sunny patio and full bath; and huge 2c garage. Absolutely A+ Winchester location steps to Wright-Locke farm, provides quick commute to Camb/Boston, or choose T from Winchester Ctr or Alewife. This energy-efficient, state-of-the-art showpiece, in one of the most sought-after towns, is like nothing out there!

Listed by Robert Bowes of Bowes Real Estate Real Living

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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508 South Border Road Winchester MA 01890

Winchester, MA508 South Border Road

Price$1,649,900

Est. Mortgage: $/month

MLS Number 72483056

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • Year Built 2020

This beautiful new construction, three level Colonial home is a must see, ready for a 4 week move in! Located across the street from Middlesex Fells Reservation, this is the perfect location for everything Winchester has to offer. This home will feature gorgeous finishes including eat-in kitchen with new quartz counters, stainless steel appliances and formal dining room. The spacious rooms through-out the home include a finished basement with full size windows, and finished 3rd floor with a 5th bedroom and bonus room! Property will have underground lawn irrigation, to help maintain the exterior of this gorgeous property!

Listed by Gary J. Litchfield and Brittany Gray of Mass. Real Estate Solutions, LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 2020
* 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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