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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15 Lawson Road Winchester MA 01890

Winchester, MA15 Lawson Road

Price$2,999,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72777864

  • Single Family Detached
  • Village East Hill
  • Bathroom 5
  • Rooms 13
  • Bedrooms 5

This tastefully updated home is exquisitely renovated with 6 fireplaces. The first floor includes sun room with 3 walls of windows, library or second home office, expansive fireplace living and dining rooms which flow to the front to back kitchen and equally large gas fireplace family room with work area and table area for hours of entertainment and mudroom. The second floor has a privately situated double door master suite with sitting room, and walk in closet. It is further complimented by 3 additional generously sized bedrooms, full family bath with double vanity & a cathedral ceiling with 2 skylights home office or 6th bedroom with half bath. The third floor retreat includes a spacious bedroom with 2 skylights, walk in & cedar closets & a full bath. Flexibility abounds with a finished & heated room above the 2 car garage - great for either another office or workout studio. The large 27,299 square foot lot features nightscape lighting, a large patio and great yard.

Listed by Anne Spry of Barrett Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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65 Myopia Road Winchester MA 01890

Winchester, MA65 Myopia Road

Price$2,599,999

Est. Mortgage: $/month

MLS Number 72775321

  • Single Family Detached
  • Bathroom 5
  • Rooms 14
  • Bedrooms 4
  • Acreage 0.9

A stately Colonial set atop Myopia Hill in one of Boston's most desired suburbs, 65 Myopia Road is a tranquil & immaculate estate well adapted to modern family living. Beyond the grand entry foyer are graciously scaled living & entertaining rooms with oversized windows highlighting beautiful views of the private outdoors. These include the double height living/family room with impressive stone fireplace, chef's kitchen with vaulted breakfast nook, & formal dining room with elegant fireplace. The home's 4 generous bedrooms are all located on the 2nd level. The Master suite is breathtaking with spacious walk-in closet and luxurious bath. Additional features of this residence include the 2nd floor mezzanine game room, home gym, expansive outdoor mahogany deck, & heated outdoor pool. This home is only 9 miles north of Boston, accessible to the commuter rail to North Station, within ½ mile +/- of Ambrose School, & within close proximity to all the shops & restaurants of downtown Winchester.

Listed by Mark Doherty of Campion & Company Fine Homes Real Estate

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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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27 Gershon Way Winchester MA 01890

Winchester, MA27 Gershon Way, Unit 27

Price$2,050,000

Est. Mortgage: $/month

MLS Number 72757101

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,638

ONLY 3 HOMES REMAIN out of 29! Designed by national, award-winning architect Gary Snider. Live surrounded by luxurious finishes, soaring ceilings, hardwood throughout & plenty of natural sunlight. This open concept plan boasts a 1st floor master suite with tray ceiling, a super-sized walk-in closet and luxurious en suite bath. The eat in kitchen is adorned with ceiling height cabinets, quartz countertops and top of the line stainless steel appliance package featuring Sub*Zero, Bosch, Wolf... The dining room has a stately coffered ceiling, bay window and sliders to a private, covered deck. The flex room can be a home office or studio for your beloved hobbies. 1st floor also features a powder room, mudroom and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath, a library and a large open loft for movie watching or game night. The icing on the cake: attached 2 Car garage with electric car charging station AND a 1,500 SF Walkout basement! MODEL HOME OPEN DAILY 11-4

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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 Stonefield Circle Winchester MA 01890

Winchester, MA1 Stonefield Circle

Price$1,849,000

Est. Mortgage: $/month

MLS Number 72725701

  • Single Family Detached
  • Bathroom 5
  • Rooms 14
  • Bedrooms 5
  • Acreage 0.25

NEW PRICE! Amazing value ~ Must see this modern 2005 farmhouse w/ oversized 2 car attached garage and wrap around farmers porch! Completely renovated and expanded by top local builder, this home is located across from the flats area in desirable Stonefield Estates cul-de-sac. This beautiful sprawling home boasts a grand yet very livable first floor with high end chefs kitchen, first floor office/ family room, beautiful dining room and front to back living room with floor to ceiling windows, access to deck / side yard and fireplace. Second floor offers 4 large bedrooms w/ 3 baths .. second floor laundry and study room. The master is beautiful with cathedral ceilings, walk in closet & custom designer bath. Finished third floor offers great space for guests/ additional office or nanny quarters! Lower level game room/ family room / gym with add'l bath. Curb appeal doesn't get much better! Enjoy all of the modern amenities along with the old world charm this special home offers!

Listed by Kim Covino of Compass

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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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248 Forest Street Winchester MA 01890
Open House

MLS Number 72770374

  • Single Family Detached
  • Next Open House: Sat 03/6 11:30 am. to 12:30 pm.
  • Bathroom 5
  • Rooms 11
  • Bedrooms 5

~NEW CONSTRUCTION IN WINCHESTER~ Here you will enjoy a tremendous location with convenient access to the Middlesex Fells, Rt 93 while also being located in the popular Muraco School District. Set on a large parcel over 37,000 sf offering a unique scenic setting with wooded views. This 11 room 5 bed, 4.5 bath Colonial built by a prominent local builder has it all! Four fully finished floors provide plenty of space for the whole family plus comfortable space for guests, in-laws and flexible areas for working from home. A gorgeous kitchen with full recessed cabinetry,GE Monogram appliances, 36" oven with exhaust hood and an upgraded island with builtin microwave and opens to a fireplaced family room with sliders to a large deck overlooking a landscaped yard with pleasant views. The finished basement is complete with a full bath and separate storage area. The 3rd floor has a large recreation room a 5th bedroom and a full bath.

Listed by The Synergy Group and Paul Cirignano of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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23 Hutchinson Road Winchester MA 01890

Winchester, MA23 Hutchinson Road

Price$1,539,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72784421

  • Single Family Detached
  • Bathroom 3
  • Rooms 9
  • Bedrooms 5
  • Acreage 0.4

If you're looking for space, this stunning move-in ready colonial has plenty of room to accommodate the growing needs for today's families. This 4,101sq. ft. home has 5 spacious bedrooms, 2.5 bathrooms, an open floor plan with beautiful hardwood flooring throughout the main living space, two fireplaces, and granite countertops in the kitchen. Additional space to accommodate a home office, gym, play area and more. The sunny and bright family room has cathedral ceilings that opens up to a large deck perfect for hosting summer barbecues with a manicured backyard that was recently updated and optimal for entertaining kids and adults. Complete with a 2 car garage, large driveway and 4 off street parking spaces, you don't want to miss this ideally located home near the Winchester Country Club golf course.

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: 2.97% last updated on Feb 25, 2021
* 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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25 Gershon Way Winchester MA 01890

Winchester, MA25 Gershon Way, Unit 25

Price$1,475,000

Est. Mortgage: $/month

MLS Number 72725070

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,980

This fabulous townhome bordering the woods was designed by national, award-winning, architect Gary Snider. Imagine luxurious finishes throughout: 10'+ ceilings, hardwood floors and plenty of natural light. This open concept plan has a 1st floor master suite with oversized walk-in closets and a great bathroom. The kitchen is adorned with ceiling height cabinets, Quartz countertops & island, a spacious pantry + top of the line SS appliance package. The dining room features a beautiful coffered ceiling. Just beyond, the room opens up to a 22' ceiling in the dramatic living room featuring a floor to ceiling fireplace. Abutting the covered porch, a wall of windows pours sunlight into this home. The 1st floor flex room can be a home office, a library or studio for your beloved hobbies. 1st floor also features a powder rm and laundry. Upstairs you'll find 2 additional spacious EN SUITE bedrooms and a bright open loft. 2 Car garage with electric car charging station.*MODEL HOME OPEN DAILY 11-4

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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123 Washington Street Winchester MA 01890

MLS Number 72773713

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 3,374
  • Complex Live/Work Winchester

Presenting a truly unique offering, located in the heart of Winchester! Perfect for our new "work from home" environment, this completely remodeled and redesigned property offers a clean, modern aesthetic with separate studio/work space. All built with sustainability and accessibility as priorities. The property features a bright 2142 sq ft residence. First level is an open concept floorplan with gourmet kitchen, massive windows for maximum light, gas fireplace and half bath, as well as French doors to the exterior. Second level features two bedrooms, one with lovely walk in closet, as well as full bathroom with tub and zero entry large shower. The studio space can be accessed from the interior or separate entrance and features cubbies for visitors, kitchenette and full bathroom. All the best in systems from CAT6 wiring to high efficiency HVAC. Private patio exclusive to this unit. See list agent for details about elevator and roof deck potential, as well as numerous other features!

Listed by Karen S. Garrett and Clay Tappan of Better Homes and Gardens Real Estate - The Shanahan Group

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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 Elmwood Avenue Winchester MA 01890

MLS Number 72672238

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,580
  • Complex allegro

NEW Construction in Town Center. MOVE IN READY, PH Home with split bedrooms and two separate balconies. This Penthouse is the largest unit at Allegro and a one of a kind floor plan that spans the entire back of the building and offers 2 master suites, half bath, 2 car parking spaces and 2 decks overlooking picturesque Vine St. It has a beautiful, open concept layout with bedrooms flocking on either side of the living room. Allegro Winchester is a boutique style building consisting of 11 unique homes in an intimate setting off the beaten path yet steps from restaurants, shopping & the MBTA Winchester Commuter Rail Station. All residences are one level with designer kitchen; gas heating & cooling; elevator access to garage parking & additional storage room. Your dream home at Allegro is ready for you now, scheduled your appointment today.

Listed by Janice Dumont of Advisors Living - Back Bay

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$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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37 Cambridge Street Winchester MA 01890

Winchester, MA37 Cambridge Street

Price$1,350,000

Est. Mortgage: $/month

Open House

MLS Number 72771272

  • Single Family Detached
  • Next Open House: Sat 03/6 11:00 am. to 1:00 pm.
  • Bathroom 4
  • Rooms 11
  • Bedrooms 4

This contemporary colonial in desirable Winchester is simply beautiful! A 2005 addition transformed this traditional home into a show-stopping open floor plan with soaring walls of windows across the back of the home. Breathtaking views of majestic pine trees provide a natural canopy over a spacious deck with lovely gardens beyond. Long sight lines flow across a modern kitchen/dining area with 2 pantries, island, quartzite counters, & new stainless-steel appliances. A living room w/built-ins & mudroom w/ a one-car attached garage complete the first floor. The second-floor owner's suite features a dramatic vaulted ceiling, tall windows with treetop views, a study & walk-in closet. 3 additional large bedrooms, 2 full baths, laundry & an office complete this floor. Lower level is partially finished w/playroom, wet bar & full bath. Lots of flex-areas everywhere! Numerous amenities & critical updates-see attached. Great transportation access to Alewife & Boston. Ambrose Elementary.

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* 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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