Winchester Luxury Homes

Known for its affluence and beauty, Winchester has some truly luxurious homes for sale. All priced over $800,000, you'll find a range of Winchester homes, from new construction mansions to contemporary condos- all with the finest features and amenities. 

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4 Dix Street Winchester MA 01890

Winchester, MA4 Dix Street

Price$3,200,000

Est. Mortgage: $/month

MLS Number 73070754

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5,500
  • High School Whs

Gracious old-world stucco Colonial. A rare combination of classic architecture completely renovated for modern living. Carefully curated interior design w/ all the upgrades. Chef’s kitchen w/ custom cabinetry, Wolf appliances, 10ft marble island, Wolf range, Sub-Zero, wine fridge, wet-bar & walk-in pantry. Gorgeous fire placed dining room. Sun-filled family room off kitchen w/French doors to outdoor bluestone patio & fenced yard. Living room w/ beamed ceilings, built-in window bench & fireplace. 1st floor offers additional living space w/ cozy sitting room & more built-ins. Grand foyer, mudroom w/ heated flrs. 5 Beds w/ 5 baths for flexible living space w/ dedicated office space & ample storage. Huge bonus rm w/ cork floors & built-ins perfect for playroom/studio. Home is professionally organized w/ storage & built-out closets. Anderson windows, high-efficiency systems, architectural roof, sound system, headed driveway. Steps to Winchester Center, train, schools, restaurants and more.

Listed by Leigh Ventura of Compass

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Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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: 6.13% last updated on Jan 26, 2023
* 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: 6.13% last updated on Jan 26, 2023
* 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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47 Wedgemere Avenue Winchester MA 01890

Winchester, MA47 Wedgemere Avenue

Price$1,899,000

Est. Mortgage: $/month

MLS Number 73073649

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,550
  • High School Whs

Wedgemere Avenue, one of Winchesters top and most desired locations! Customize this stunning 5 bed 15 room home & create the home of your dreams! This unique and lovingly maintained property offers a perfect layout with large rear addition/ family room directly off the kitchen featuring 20' vaulted ceilings, an oversized stone fireplace & french doors to patio. Enter into the warm & welcoming foyer flanked by the dining room & front to back living room boasting original woodwork & beautiful details incl a wood burning fireplace w/ adjacent sun room or home office. The second story offers a 3 room primary suite w/ bath, dressing room & access to sun deck. Three add'l rooms, one being perfect for an office plus hall bath complete this floor. The third offers two more bedrooms & a full bath. Enjoy the spacious lower level game/rec/gym room w/ secondary kitchen, laundry & bath. Perfectly level 13k+ lot plus a 4 car garage or 2 car with workshop offers space for projects or car enthusiast!

Listed by Kim Covino & Co. Team and Kim Covino of Compass

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$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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111 Cambridge Street Winchester MA 01890

Winchester, MA111 Cambridge Street

Price$1,700,000

Est. Mortgage: $/month

MLS Number 73071135

  • Residential
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 3,436
  • High School Whs

Gorgeous six-bedroom home has been lovingly renovated throughout. This house beautifully blends modern living with old world charm combining a new kitchen and baths with quality millwork, soaring ceilings, French doors and a stunning staircase of old. Step through the grand entry hall to an open dining/kitchen with Bosch appliances, a quartz-top island, coffered ceiling, custom cabinetry, new flooring, lighting, windows and hardware throughout. Enjoy entertaining in the front to back oversized living room with fireplace. Pass the elegant arched window to the second level with 4 bedrooms including the Primary en suite. With oversized bedrooms, a second full bath and excessive storage, there is plenty of space for all! The top floor offers two bedrooms, more storage and a bonus room. This home has a new electrical system, roof, fence, landscaping and has been repainted inside and out. Located minutes from Ambrose, the train and Winchester Center, don’t miss this rare move in ready home.

Listed by Lynne Russo of Better Homes and Gardens Real Estate - The Shanahan Group

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$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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: 6.13% last updated on Jan 26, 2023
* 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 Dana Avenue Winchester MA 01890

Winchester, MA11 Dana Avenue

Price$1,449,000

Est. Mortgage: $/month

Open House

MLS Number 73074575

  • Residential
  • Next Open House: Sat 02/4 12:00 pm. to 1:30 pm.
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,624

This meticulously renovated and expansive ranch-style home checks all the boxes. The open floor plan is well suited for everyday living and entertaining. Featuring a tastefully designed living room with stunning fireplace, dry bar and large windows that flood the space with natural light. An elegant dining room opens to a richly appointed eat-in kitchen with center island, beautiful crisp, white cabinetry and stainless-steel appliances. Adjacent is an expansive family room with vaulted ceilings with direct access to the deck and level manicured yard. The master bedroom suite features custom closets and marble tiled bath. There are two additional bedrooms with ample closets and a full bath on this level. The finished lower level has a large family room, laundry, office, plus mudroom with access to a two-car heated garage. All this plus newer roof, updated utility systems, central AC, Pella windows, composite deck and plenty of storage. With so many updates it feels like new.

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

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$
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$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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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40 Elmwood Avenue Winchester MA 01890

MLS Number 73073522

  • Condo
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,662
  • High School Winchester High

The CROWN JEWEL of the building! This truly special unit is flooded with light and boasts (2) private decks, (2) master suite options, and (2) garage parking spaces. Allegro is conveniently located in DOWNTOWN WINCHESTER. Picture yourself strolling down for your morning cup of joe, then over for a quick visit to the farmers market to pick up some fresh items for dinner. Don't feel like cooking? We don't blame you! Out the door you go, AGAIN, to enjoy any one of the fabulous restaurants our town center has to offer. This is how you live when you live Allegro. This elegant Penthouse unit boasts in-unit laundry and easy one level living. Don’t forget about the elevator and heated garage for your car. Condo fee includes trash service, landscaping, snow removal, property maintenance, PLUS HEAT & WATER!

Listed by Vita Realty Group, Robert Cipro and Philip J. Vita of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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 Glenwood Avenue Winchester MA 01890

MLS Number 73066850

  • Condo
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,225

High Quality New Construction in convenient location easy access to everything. Home features open concept Kitchen, dining area and living room perfect for entertaining. Hardwood flooring throughout bedrooms and bonus rooms. Slider off to small deck to backyard. Treks siding on front porch and back deck. All quality SS appliances, white cabinets, center island, fireplace in LR. Second floor features Master Bed and Bath, two other bedrooms with one additional full bath. Finished Bonus family room/office on 3rd Floor. Basement has high ceilings and walk out. Plenty of parking.

Listed by Claire Moore-Rosa of Burns & Egan Realty Group,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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 Glenwood Avenue Winchester MA 01890

MLS Number 73066852

  • Condo
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,285

High Quality New Construction in convenient location easy access to everything. Home features open concept Kitchen, dining area and living room perfect for entertaining. Hardwood flooring throughout bedrooms and bonus rooms. Slider off to small deck to backyard. Treks siding on front porch and back deck. All quality SS appliances, white cabinets, center island, fireplace in LR. Second floor features Master Bed and Bath, two other bedrooms with one additional full bath. Finished Bonus family room/office on 3rd Floor. Basement has high ceilings and walk out. Plenty of parking.

Listed by Claire Moore-Rosa of Burns & Egan Realty Group,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.13% last updated on Jan 26, 2023
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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