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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5 Cambridge Street Winchester MA 01890

Price$4,499,000

Est. Mortgage: $/month

MLS Number 72476341

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Year Built 1857
  • Full Bath 4

Majestic WATERFRONT Estate situated on the west bank of the Mystic lake with breathtaking views over the water and onto the Boston Skyline! Over an acre of rolling hills, the most gorgeous and serene setting in all of Winchester; this property is like no other! This home has been completely & lovingly renovated and restored to its original grandeur blending exquisite detail with modern day luxuries.This home boasts 12' ceilings on the first and showcases 13 rich and elegant rooms that you can only appreciate in person. Enter though the grand foyer and your eye is drawn through the living room windows and over the rolling hills of the beautifully manicured lawn to the lake and beyond to the Boston skyline! With Winchester being only 8 miles north of the city and Logan airport, this home is a commuters dream. 5 bedrooms on the second floor with 4 baths,Grand Master overlooking lake with fireplace & gorgeous spa bath. Must see this rare and never before offered home for sale in Winchester

Listed by Kim Covino of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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 Grove Street Winchester MA 01890

Price$4,299,000

Est. Mortgage: $/month

MLS Number 72461829

  • Single Family
  • Garage 3
  • Parking Spaces 3
  • Year Built 1914
  • Full Bath 6

Restored to its former grandeur, and renovated to modern splendor is your new home in highly desirable Winchester, MA - just 7 miles from downtown Boston. Enjoy all the convenience of being close to the city but still far enough away to relax in the serenity of this premium suburb (bonus - Winchester is situated close by to the PRIVATE AIR TRAVEL HUB of Bedford Hanscom Field Airport). Features of the home you will appreciate include a SECOND MASTER, smartly placed across the home from the main master bedroom; GYM and SAUNA/STEAM/SPA room to keep healthy, whole and mindful; WIRED FOR SMART HOME FEATURES including audio, video, and security. A third floor for extended guests or staff features a SECOND LAUNDRY ROOM, and the finished basement hosts an 1100 BOTTLE WINE CELLAR, MEDIA ROOM, and kitchen area, that will be the space to entertain your guests for movie nights or big games. A 3+ CAR GARAGE completes this magnificent home.

Listed by Michael Carucci and James Raggi of Gibson Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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7 Lakeview Road Winchester MA 01890

Price$3,769,000

Est. Mortgage: $/month

MLS Number 72485984

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Village Mystic Lake
  • Year Built 1880

Truly inspired in both its space and creativity, no expense was spared while creating this extraordinary home overlooking Upper Mystic Lake; it's one of the best renovations Winchester has ever seen. The entire house was gut-renovated to the studs and the then carefully rebuilt. An addition seamlessly melds with the original lines, allowing for the creation of an open kitchen and family room. Step onto the expansive deck from your master bedroom and take in the lake views. Cuddle up by your outdoor fireplace or open up the carriage house bar and billiards areas and grill up a feast. There's 5 bedrooms, 4.5 baths, a jaw-dropping dining room, stately home office, elevator, lovely living room and study plus a top floor bonus room. This beauty sits on spectacular grounds with a charming landscaped path that leads to your private dock on the lake. Truly an oasis that makes you feel like you're at a resort in Maine! Just 8 miles from Boston, walk to the trains, town center and schools.

Listed by Nancy S. Pallotta of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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 Harrison Street Winchester MA 01890

Price$3,295,000

Est. Mortgage: $/month

Open House

MLS Number 72466644

  • Single Family
  • Next Open House: Sun 28th 12:00 pm - 1:00 pm
  • Garage 3
  • Parking Spaces 4
  • Village The Flats

New construction colonial will take your breath away! Entryway opens up to an open concept layout: Family room w/ gas fireplace, dining room, living room, grand kitchen, office, mudroom w/ built-ins & 1.5 baths. The kitchen features an oversized island w/ White Rhino counters, Wolf double oven w/ grill, griddle, custom hood & pot filler, 54" sub zero fridge/freezer, 2 sinks, 2 dishwashers & pantry. Sliders open up to a patio & expansive lawn. 2nd floor features the grand master suite plus 3 additional bedrooms, all w/ ensuite bathrooms & walk-in closets. Master includes dramatic vaulted ceilings, cupola, attached sitting room, oversized celebrity style closet & master bathroom w/ soaking tub, rain shower & marble floors. The 3rd floor has 2 bedrooms & 1 full bathroom. Finished lower level w/ sunken media room, cable/internet setup, central vac & sitting room w/ full bathroom. Additional features: oversized laundry room; heated floors in full bathrooms; heated oversized 3-car garage.

Listed by Andersen Group Realty and Sven Andersen of Keller Williams Realty Boston Northwest

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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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15 Cambridge Street Winchester MA 01890

Price$2,998,000

Est. Mortgage: $/month

MLS Number 72484213

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Year Built 1941
  • Full Bath 5

Live Waterfront - on Mystic Lake! This totally renovated and expanded Colonial is now a modern classic, designed for comfortable, gracious living. Open First Flr features Lg windows/glass paneled drs across back, providing abundant natural light and stunning views from Kit/Fam Rm, Liv Rm w/FP and Dining Rm. Gorgeous Cook's kitchen w/high-end appliances, Lg island, leathered granite and mahogany counter tops, and wet bar for entertaining. Handsome private, paneled office w/FP, Mud Room and half bath complete floor. Second Flr boasts 4 bedrooms, all w/meticulously finished en suite baths. Retreat-like master w/dressing closet, 2nd double wardrobe, luxurious bath w/soaker tub with lake and Boston Skyline views. All finished LL w/separate entrance incl: Media/Game Rm w/FP; flexible 5th Bdrm suite, in-law, au-pair or workout rm; full bath accessed via bdrm or hall; 2nd ldry area. Sited on prof landscaped 29K+ sf lot w/new deck, stone patio and steps to 111 ft Lakefront. 8 miles to Boston.

Listed by Ann Basmaji of Waterfield Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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60 Wedgemere Avenue Winchester MA 01890

Price$2,599,000

Est. Mortgage: $/month

MLS Number 72469658

  • Single Family
  • Garage 2
  • Parking Spaces 8
  • Year Built 1929
  • Full Bath 5

INCREDIBLE, VINTAGE, HISTORIC, TUDOR LOOKING FOR A FAMILY TO MAKE NEW MEMORIES!!! Are you looking for a home which is both modern and loaded with historic charm and character? Look no further and welcome to 60 Wedgemere Avenue. Located in the exclusive "Flats Of Winchester" and meticulously maintained, this home has it all! Boasting a Chef's kitchen with a top of the line SS appliance package, huge granite island and french doors to a private stone patio, perfect for lounging in during those impending warmer days. The oversized, fireplaced family room has plentiful custom built-ins, magnificent woodwork and is flooded with natural light. This spacious 6 bedroom, 5.5 bathroom house underwent a major renovation and addition in 2006. Private and quiet neighborhood, a short drive to Winchester center, where you'll find an abundance of coffee shops, boutiques, salons, restaurants and the commuter rail to Boston. Within the Vinson Owen school district and easy access to major highways.

Listed by The Marrocco Group and Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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

Price$2,599,000

Est. Mortgage: $/month

Open House

MLS Number 72463183

  • Single Family
  • Next Open House: Sun 28th 12:00 pm - 2:00 pm
  • Garage 2
  • Parking Spaces 4
  • Year Built 1982

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, with brilliant sunrises that change hourly with the light and weather. 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 of Berkshire Hathaway HomeServices Commonwealth Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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45 Bacon Street Winchester MA 01890

Price$2,599,000

Est. Mortgage: $/month

Open House

MLS Number 72470493

  • Single Family
  • Next Open House: Sun 28th 12:00 pm - 1:30 pm
  • Garage 3
  • Parking Spaces 5
  • Year Built 2011

PREMIER LOCAL BUILDER's PERSONAL RESIDENCE! Incredible location in Winchester's desirable "Flats" neighborhood, walk to the commuter rail to Boston. The welcoming double story foyer is flanked by a spacious dining room & sunny living room. Host a cooking class in the incredible Chef's style kitchen, boasting a top of the line SS appliance package & enormous granite island. Sit by the fireplace to unwind or enjoy the impending warmer days on the deck & spark up the grill. Puppies love frolicking in the fenced in backyard! The master suite boasts a large WIC, radiant heated floors & a steam shower. 4 other bedrooms with en-suite baths & an "au pair" living quarter with separate entrance from the garage. The basement features a fabulous bar & bonus room, a great space for parties! Downtown Winchester, bustling with coffee shops, salons & restaurants is a short walk. Ginn Field & playground is around the corner. Within the Ambrose school district and easy access to major highways.

Listed by The Marrocco Group and Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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 Central Green Winchester MA 01890

Price$2,499,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72478675

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Village Rangeley
  • Year Built 1930

The epitome of sophistication in Winchester's Rangely neighborhood! This breathtaking Georgian boasts an elegant brick exterior & luxurious interior. On the 1st floor, relax by a fire in the living room, in the office, or in the formal dining room. Gourmet kitchen w/ large island, stone/granite countertops, spacious cabinets & pantry, dining area, wet bar, recessed lighting & patio access. Family room w/ fireplace & a 1/2 bath complete 1st floor. Head upstairs to the master suite for self-care in your spa-like ensuite bathroom, & enjoy a celeb-style dressing room/walk-in closet. 2nd floor includes 4 additional bedrooms, 2 bathrooms & oversized, luxurious laundry room. 3rd floor has 1 bedroom w/ ensuite bathroom and an office/den. Enjoy the oversized backyard w/ 2 private patios & enchanting gardens. Additional features: partially finished lower level, 2 car garage, central air, Sonos speakers (1st floor). Walking distance to Winchester Center, schools, commuter rail & walking trails.

Listed by Andersen Group Realty and Sven Andersen of Keller Williams Realty Boston Northwest

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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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20 St. Thomas More Drive Winchester MA 01890

Price$2,499,000

Est. Mortgage: $/month

Open House

MLS Number 72488480

  • Single Family
  • Next Open House: Sat 27th 1:30 pm - 3:00 pm
  • Garage 3
  • Parking Spaces 5
  • Year Built 2000

Welcome home to this beautiful custom built brick colonial in a neighborhood of several newly built homes. The foyer is two story with curved staircase into the open floor plan. The family room has a cathedral ceiling, floor to ceiling fireplace, beautiful elliptical windows that add plenty of sunshine to this room with spacious built ins. The kitchen has hardwood flooring, Thermador appliances, and wet bar. There is a step down sunroom for dining with a wall of windows, skylights and a patio door that leads to your private backyard. This home has 2 work at home office/homework rooms on the first floor, both with glorious windows to make your workday a pleasure. This home has a 3 car garage with direct access to mudroom/laundry.There is a walkup finished 3rd floor and 2 sliders in the walkout LL. Four floors of finished space. Located in the recently finished Vinson Owen School and newly completed Winchester High School. There are 2 commuter rail stops and just 10 miles from Boston

Listed by Buono/Lyons Team of Century 21 CELLI

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* 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.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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