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 A Fernway Winchester MA 01890

Winchester, MA5 A Fernway

Price$3,395,000

Est. Mortgage: $/month

MLS Number 72884501

  • Single Family Detached
  • Village Myopia Hill
  • Bedrooms 5
  • Bathroom 6
  • Rooms 12

EXCEPTIONAL FIND! BETTER THAN NEW, much improved and customized with designer fixtures and quality elegant,timeless finishes, allow for immediate easy living & enjoyment. Enter a stunning living-room with fireplace from the 2 story hall, elegant dining-room, 2 Bespoke customized home-offices.A fully equipped Gym for your convenience.Enjoy the Cooks kitchen with 6 Burner cooktop & large island, eat in area, family-room w/fireplace and deck all connect for entertaining family and friends. Custom 3 car garage connects to the mudroom. A gracious staircase leads to the owners suite with gorgeous bath and walk in closet. Guest room with ensuite bath, 2 Bedrooms share a bath, 5th BR used as a home office with walk in closet. Bonus walk up ready for your finish. Fantastic lower full walkout above ground level, w/ recreation/Br,1200 bottle Wine-cellar, Kitchenette by Bespoke,marble bath with walk in shower and more. Exclusive, much sought after "MYOPIA HILL" Winchester CC, golf course location.

Listed by Dorothea Feffer of Coldwell Banker Realty - Winchester

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Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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282 High Street Winchester MA 01890

Winchester, MA282 High Street

Price$3,300,000

Est. Mortgage: $/month

MLS Number 72867636

  • Single Family Detached
  • Bathroom 5
  • Rooms 16
  • Bedrooms 6
  • Acreage 0.56

Stunning family compound setting built with pride & quality offered for first time.Once in a generation opportunity.Uniquely generous in size and scale.Light filled,modern all brick home abundant in space and comfort.Unrivaled privacy at end of cul-de-sac.Masterfully built staircase presents the two story great room with double sided fireplace.Spacious kitchen with island, double gas range, and 66" of refrigeration.Grand formal dining room,serving pantry,dinette,and fabulous living room make up the first floor common areas.Add a main level bedroom,seperate full and half baths,and large office complete the primary level.Upstairs,open primary suite complete with stone fireplace,ensuite bath,and dressing room.Three additional bedrooms,big full bath,and laundry on second level.Full,finished walkout basement with kitchen,living area,brick oven,fireplace,dinette,and additional 6th bedroom and bathroom ideally suited for in-law,au pair,or multigenerational suite.Rare,attached 4 bay garage.

Listed by Anthony Marino of Marino Real Estate Group

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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32 Calumet Road Winchester MA 01890

Winchester, MA32 Calumet Road

Price$2,499,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72903321

  • Single Family Detached
  • Village Flats
  • Bathroom 5
  • Rooms 12
  • Bedrooms 6

Top flats location! This stunning 6 bed 4.5 ba. home has been tastefully renovated & meticulously maintained blending old world charm w/ modern amenities. A spacious entry foyer welcomes you into this grand home & flows into a sun drenched living room w/gas fireplace featuring a beautiful bay window & french doors to inviting screen porch. A cozy family room, formal dining room w/ beamed ceilings, adjacent butlers pantry, and an oversized expanded kitchen w/island, high end appliances & dining area w/cathedral ceilings showcasing a wall of windows overlooking lush private yard completes this floor. Second floor offers 4 large bedrooms, including a master suite w/ private bath & great closet space. The 3rd floor has 2 add'l bedrooms and a full updated bathroom. Lower level features TV/ playroom, gym, storage & full bath with a jacuzzi tub. Private rear yard with bluestone patio, plumbed gas grill & stone walls create the perfect space for entertaining. 2 gar garage, new windows.

Listed by Kim Covino of Compass

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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119 Forest Street Winchester MA 01890

Winchester, MA119 Forest Street

Price$2,349,000

Est. Mortgage: $/month

MLS Number 72893561

  • Single Family Detached
  • Village Fells area
  • Bathroom 6
  • Rooms 12
  • Bedrooms 5

Must see this fabulous +/- 6000 sf Colonial farmhouse! This newly constructed 5 bed, 4 full, 2 half bath home by premiere local builder is one of a kind & offers space & style that will impress! With the frontage on Bell Road, the location offers an abundance of privacy and side street access. From the moment you enter you will feel the quality & appreciate the beautiful craftsmanship; features include a stunning kitchen w/quartz counters, wide plank oak flooring, oversized island, Viking appliances w/ 48" fridge, 6 burner gas range along with a wet bar w/wine fridge & walk in pantry! Adjacent family room w/fplc, formal dining room, living room & stunning office w/ walls of windows, Amazing master suite w/ spa like bath, soaking tub & oversized marble shower. 4 additional spacious bedrooms /2 en-suite, 2 car garage w/2 charging outlets, direct entry to mudroom w/ bench, bead board trim & cubbies. Great lower level Media/Game/Home Gym. In wall speakers & smart locks, Don't miss!

Listed by Kim Covino of Compass

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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28 Gershon Way Winchester MA 01890

Winchester, MA28 Gershon Way, Unit 28

Price$1,690,000

Est. Mortgage: $/month

Open House

MLS Number 72857591

  • Condo or Co-op
  • Next Open House: Thu 10/21 11:30 am. to 3:00 pm.
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,980

2021 Winner for BEST NEW 55+ COMMUNITY IN THE UNITED STATES. ONLY 2 HOMES REMAIN out of 29! 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.*SALES CENTER 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: 3.05% last updated on Oct 14, 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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254 Main Street Winchester MA 01890

Winchester, MA254 Main Street

Price$1,689,000

Est. Mortgage: $/month

MLS Number 72873085

  • Single Family Detached
  • Village Downtown location
  • Bedrooms 4
  • Bathroom 3
  • Rooms 10

Must see this stunning and very spacious home! Set on an oversized lot with great rear yard just outside the vibrant town center; this sprawling 10 room, 4 bedroom 2.5 bath home w/ 3 car garage will exceed your expectations! Recently renovated and expanded this great home has the look and feel of a colonial from the exterior yet offers a stunning redesigned open concept kitchen w/ great room addition on the rear w/soaring ceilings, amazing space and contemporary flair! The high end kitchen is the heart of the home with wonderful flow for entertaining, island seating and adjacent wine bar. Great room off kitchen with breathtaking space, vaulted ceilings, double gas fireplaces and sliders to spacious deck overlooking the rear yard. Pantry storage, mudroom & laundry all just off the kitchen. Formal dining, living room w/fplc. & sunroom/family room complete this floor. The second features 4 bedrooms, a grand master w/ vaulted ceilings & private bath plus 3 add'l bedrooms and full bath.

Listed by Kim Covino of Compass

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$
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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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157 Highland Avenue Winchester MA 01890

Winchester, MA157 Highland Avenue

Price$1,599,000

Est. Mortgage: $/month

MLS Number 72908778

  • Single Family Detached
  • Village Fells
  • Bathroom 4
  • Bedrooms 6
  • Rooms 10

Majestic 6 Bedroom 4 bath home close to the town center and seconds to the Fells! Enter into the stunning open foyer w/high ceilings flanked by a great home office w/built ins and a sunny living room w/wood burning fireplace. The dining room is large w/original detail, china cabinets & flows nicely into the updated cherry kitchen w/stainless appliances, granite island with lots of prep space, breakfast area & easy access to rear deck & yard. The1st floor also features a beautiful large screened in porch with a treehouse feel & a full bath! The 2nd floor offers 4 generously sized bedrooms, and an updated full bath.The third floor has an add'l full bath and two large bedrooms. A nicely finished lower level includes a media center with a fireplace, a full bath and a wet bar. The lower level and kitchen both have direct access to a sprawling deck overlooking the backyard of your dreams including a stone patio, play area and plenty of lawn space, all fenced in. Direct access 1 car garage.

Listed by Kim Covino of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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60 Emerson Road Winchester MA 01890

Winchester, MA60 Emerson Road

Price$1,449,000

Est. Mortgage: $/month

MLS Number 72896521

  • Single Family Detached
  • Village West Side
  • Rooms 9
  • Bathroom 3
  • Bedrooms 4

GREAT NEW PRICE! Tastefully renovated 4/5 bed home nestled into the hillside at the end of desirable Emerson Road! Enjoy the backyard oasis filled with peach and apple trees, nice lawn area and new deck perfect for outdoor entertaining. Enter the home through the welcoming foyer and fall in love with the sunny open floor plan. The spacious european designed kitchen offers an oversized island w/ seating, high end appliances with an abundance of storage & breakfast area w/ picture window. A formal dining room, sunny living room w/ historic fireplace & family room/ or 5th bed with a full bath and a laundry room complete the first level. The second floor offers 4 bedrooms w/ 2 bathrooms; a fabulous master suite w/ updated full bath and custom walk in closet, and an office/homework space w/ built in desks. Finished lower level with family room, fireplace, fun kids play area and plenty of storage. 2 car attached garage, central AC, all new windows & updated systems. Move right in and enjoy!

Listed by Kim Covino of Compass

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$
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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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8 Sanborn Street Winchester MA 01890

Winchester, MA8 Sanborn Street

Price$1,360,000

Est. Mortgage: $/month

MLS Number 72902520

  • Single Family Detached
  • Bathroom 3
  • Rooms 8
  • Bedrooms 4
  • Acreage 0.19

Welcome to this charming 1850 colonial located in desirable Easthill neighborhood close to town and trains. This home has all the charm of yesteryear with high ceilings and hardwood floors. Lovely bookcases and window seat with fireplace in cozy family room. Updated custom kitchen with views of deck. Attractive dining room leads to private side screened porch. Four bedrooms on second floor with master suite and open space for an office in hallway .Large walk up attic.Expansive patio off deck and separate fenced in gardens. All in all a pretty corner lot with side yard as well.Fall in love with this inviting home and fabulous location

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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19 Hancock Street Winchester MA 01890

MLS Number 72893699

  • Single Family Detached
  • Bedrooms 5
  • Bathroom 2
  • Rooms 11
  • Square Feet 3,065

Investors and owner occupants! This Classic two family with craftsman details is located on quiet street in Winchester Highlands with 15,000 sf lot, could easily be converted to a single family. Walking distance to The Fells Reservation, perfect for hiking, biking, or walking your dog. Close proximity to downtown Winchester with shops, restaurants, Commuter Rail and more. First floor unit, 2 bed, 1 bath. Second floor unit, 3 bed, 1 bath. Both units feature sunny living rooms, large formal dining rooms, and hardwood floors throughout. The second floor could be converted to 4-5 bedrooms. Front covered porch and large rear deck, plus immense side yard offers potential for expansion. Includes giant driveway that can comfortably fit 6 cars, plus 2 garage spaces.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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