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Luxury Homes in Winchester MA

View current luxury homes for sale in Winchester, MA below. You may also be interested in viewing listings for Greater Boston luxury homes.

Winchester Luxury Real Estate

Contact Barrett Sotheby's International Realty or call our Winchester office directly at 781-729-7900 with any questions or to schedule a viewing. 

20 Westland Avenue Winchester MA 01890

Winchester, MA20 Westland Avenue

Price$2,299,000

Est. Mortgage: $/month

Open House

MLS Number 73059770

  • Residential
  • Next Open House: Sat 12/3 11:00 am. to 12:30 pm.
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,400

Extraordinary ALL NEW renovation/expansion! 4 bedroom 3.5 bath colonial with 2 story rear addition in top west side neighborhood; the most recent project by premier design/build team “Renew” w/ high end finishes from Ralph Lauren, Restoration Hardware, Duravit, Emtek & more! The must see kitchen is the focus of main level boasting an oversized Carrera marble island, custom cabinetry & gorgeous overhead designer light fixture. Desirable open concept kitchen & family room w/fireplace, walls of windows & French doors leading to oversized patio & newly landscaped yard. Living room w/wood burning fireplace & french doors plus a great home office flooded w/ sunlight, mudroom side entry w/built-ins & spacious half bath complete the first level. Second level has a fabulous primary suite with high cathedral ceilings, sitting area & marble spa-like bath plus 3 additional bedrooms & 2 full gorgeous baths. Lower level offers a large family room w/fireplace & office/rec/workout room. Just perfect!!

Listed by Kim Covino & Co. Team 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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48 Oak Street Winchester MA 01890

Winchester, MA48 Oak Street

Price$2,099,000

Est. Mortgage: $/month

MLS Number 73059441

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,534

New Construction just a short walk to downtown! Development is underway and slated for completion in late spring! 1st floor has an inviting open concept layout with kitchen, family room and dining room. Workstation with built in desk and walk in pantry adjacent to kitchen area as well! The balance of the 1st floor offers a living room/office and bedroom with bath or could also be used as a study or extra play area! 2nd floor has spacious primary suite with generous closet and dream bathroom with dual vanities and plenty of storage. 2nd bedroom upstairs also has en-suite bath. 2 additional bedrooms on 2nd floor. Laundry room on 2nd floor completes the level. Bonus room in lower level will truly be a great bonus! Exterior offers patio with built in entertainment center! The design board pictures are attached also with pictures from a recently completed project in Winchester...

Listed by Mark Donnellan 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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1 Socrates Way Winchester MA 01890

Winchester, MA1 Socrates Way

Price$1,995,000

Est. Mortgage: $/month

MLS Number 73054183

  • Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 5,122
  • High School Whs

SPACE GALORE! Welcome to this fantastic 5 BR, 3.5 bath colonial on a little over an acre lot. The comfortable floor plan maximizes space with plenty of room for entertaining and spreading out. The light and airy living and dining room lead to a good size open concept kitchen which sits right in the center of the home. You'll feel as though you are perched up on a bird's nest looking out from the family room to the deck. On the 2nd FL, the primary suite is equipped with a fireplace, walk-in closet & full bath with a soaking tub. Laundry and 2 additional bedrooms complete this floor. The third level offers 2 additional bedrooms w/ full bath and office/media room. You'll love the convenience of simply taking a few stairs to your own home gym and hair/make up studio in the basement level, offering perfect for access for trainers and stylists. Outside this home is surrounded by mature trees and a direct path to Nutile Field make for a picturesque suburban setting.

Listed by Johan Lopez of Home Shop Properties,Inc.

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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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18 Middlesex Street Winchester MA 01890

Winchester, MA18 Middlesex Street

Price$2,595,000

Est. Mortgage: $/month

MLS Number 73047571

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Square Feet 4,500

This extraordinary property is privately situated, yet, just minutes from Boston. European inspired and masterfully crafted, showcases sophisticated design and top-of-the-line systems. A well appointed floor plan awaits with grand scale rooms and elegant charm. Enter through the magnificent foyer, featuring a beautiful curved staircase that leads into the formal living room and separate family room. Bespoke chef's kitchen comes outfitted with professional grade appliances, fireplace and adjoining mudroom. In addition to 3 en-suite secondary bedrooms, the primary suite rivals the finest hotels offering a spa like bath, complete with bidet and w/I closet. Seamless indoor/outdoor flow through 8 sets of French doors to marble columned loggia, lush landscaping, sparkling salt water heated pool and sound system thru-out. An unparalleled entertainment oasis. Other features incl 350 gallon Reef Tank, full wet bar, ideal LL au-pair suite, heated driveway. All a stones throw from town center.

Listed by Candice Macoul of Luxury Living 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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6 Harrington Road Winchester MA 01890

Winchester, MA6 Harrington Road

Price$1,595,000

Est. Mortgage: $/month

MLS Number 73044931

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,688

Situated on a private cul-de-sac moments from Winchester Center, a gracious single-family residence is available for the first time in over 35 years. Featuring a large level lot, this property has a significant amount of potential with many unique details, making this home a rare find in Winchester. Meticulously maintained over the course of ownership, it boasts 4 large bedrooms including a primary suite, 3 Full and 1 half baths, walk up attic, and beautiful spaces with original details. A finished lower level, attached garage and beautiful level yard, compliment the potential in this property. Located minutes to the Wedgemere, and Winchester Center commuter rail stations 6 Harrington Road is an opportunity for a buyer with a creative vision.

Listed by Matthew Diozzi 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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6 Wickham Road Winchester MA 01890

Winchester, MA6 Wickham Road

Price$1,799,900

Est. Mortgage: $/month

Open House

MLS Number 73044791

  • Residential
  • Next Open House: Sat 12/3 1:30 pm. to 2:30 pm.
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3,248

If prime location & classic layout top your list of must-haves, this center entrance Colonial in a well-loved neighborhood will capture your attention! The beautiful foyer welcomes you into a gracious front-to-back formal LR. Cozy kitchen w/tasteful granite countertops & SS appliances opens into a stunning family room, sun-splashed & spacious, w/FPL & cathedral ceilings. Step outside to enjoy crisp Fall evenings on your deck & feel the enchantment of lovely landscaping in your private backyard! Both the LR & DR are accented w/wainscoting detail throughout. A 1st floor powder room w/laundry completes the layout. Upstairs, there are 4 well-proportioned corner bedrooms w/a common bathroom. The primary bedroom boasts vaulted ceilings & a full en suite bathroom. Movie nights will be memorable in the lovely LL w/3rd FULL bath, wine closet & bar, plus walk-out to an over-sized 2 car garage! Close to town center, shops & restaurants & train!

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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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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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

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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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2 Reservoir Street Winchester MA 01890

Winchester, MA2 Reservoir Street

Price$1,990,000

Est. Mortgage: $/month

Open House

MLS Number 73027354

  • Residential
  • Next Open House: Sun 12/4 12:00 pm. to 1:00 pm.
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,267

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

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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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5 Manomet Road Winchester MA 01890

Winchester, MA5 Manomet Road

Price$1,649,000

Est. Mortgage: $/month

MLS Number 73018758

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,800
  • High School Whs

Price reduced. Come see and prepare to be inspired! Spectacular and tasteful describe this 4 bedroom, 4 bath beauty in the Ambrose School District within a minute to the fabled Myopia Hill neighborhood. Meticulous, modern, and transitional flair with attention to detail and quality make this home a gem.Fabulous white kitchen with quality appliance package and white Carrera Quartz countertops.Maintenance free exterior, and professionally landscaped yard will dazzle your senses.Bright and open concept within the kitchen, dining and living areas with 2 bedrooms and full bath make up the main level.Upstairs encompasses the primary suite with connecting full bathroom and additional bedroom and full bath & laundry.Finished lower level with playroom, mudroom, home office, 4th full bathroom, and 2nd set of laundry hookups. Extra long heated garage and storage area complete the basement.Rarely does so much punch get put into such a nifty space.Value and quality are unmistakable.

Listed by Anthony Marino of Marino Real Estate 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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