Winchester Homes for Sale

A busy urban street with shops in Winchester, MAWinchester, Massachusetts is a quiet, bedroom community conveniently located just 8 miles north of Boston. Winchester is home to several lakes and parks. Winchester is a family-friendly community that is home to several well-maintained parks, several lakes, and lots of trails.

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5 A Fernway Winchester MA 01890

Winchester, MA5 A Fernway

Price$3,395,000

Est. Mortgage: $/month

Open House

MLS Number 72884501

  • Single Family Detached
  • Next Open House: Sat 10/30 1:00 pm. to 3:00 pm.
  • Village Myopia Hill
  • Bathroom 6
  • Bedrooms 5

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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$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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: 3.09% last updated on Oct 21, 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 Glengarry Road Winchester MA 01890

Winchester, MA8 Glengarry Road

Price$2,599,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72912027

  • Single Family Detached
  • Village Downtown/ Wedge pond
  • Rooms 11
  • Bedrooms 5
  • Bathroom 5

BETTER THAN NEW! Must see this 5 bed 4.5 bath colonial, completely renovated and mindfully redesigned. This stunning home is located just outside the center in a most desired neighborhood; w/much of the interior reframed, it is sure to offer the layout todays buyers desire. Enter into the grand foyer as you are drawn to the front to back living room with gas fplc, & exceptional original woodwork and detail throughout. The stunning kitchen with 48' Wolf stove, Sub Zero fridge and an oversized honed Quartz island is a chefs dream! Adjacent dining area / dining room are offered as flex spaces depending on your family's needs. Family Rm w/ bay window, office & powder room complete this floor. The second floor showcases an inviting Master bedroom w/ gas fireplace, lavish spa-like bath w/ soaking tub and stall shower& walk in closet with custom shelving plus 2 add'l en-suite bedrooms flooded with sunlight, 2nd floor laundry. The third has 2 add'l beds w/vaulted ceil & full ba. Finished LL

Listed by Kim Covino of Compass

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%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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 Johnson Road Winchester MA 01890

Winchester, MA119 Johnson Road

Price$2,399,000

Est. Mortgage: $/month

MLS Number 72912471

  • Single Family Detached
  • Rooms 12
  • Bedrooms 6
  • Bathroom 6
  • Acreage 0.72

Modern French-style, farmhouse within the Vinson Owen district!! This new construction lovingly designed 6 bedroom, 4 bathroom home with 2 half baths is ideal for raising a family & enjoying everything Winchester has to offer, including a bustling downtown & 2 commuter rails to Boston. The spacious floor plan is comfortable for entertaining & allows several locations to accommodate a home office. Easy access to major highways & 7 miles North of Boston.

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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: 3.09% last updated on Oct 21, 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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15 Vinson Circle Winchester MA 01890

Winchester, MA15 Vinson Circle

Price$1,999,000

Est. Mortgage: $/month

MLS Number 72911440

  • Single Family Detached
  • Bathroom 4
  • Rooms 9
  • Bedrooms 4
  • Acreage 0.98

Private 1 acre lot! Situated on one of the most beautifully manicured & exclusive lots in Winchester, this unique property offers endless opportunities to create your dream home! Dramatic open layout w/ walls of windows, soaring cathedral ceilings, featuring 4+ bedrooms, 3.5 bathrooms & including an attached in-law suite w/ a full bathroom, kitchen / cabinetry, & private exterior access. The updated chefs kitchen includes four ovens, gas stove, a skylight and double sliding glass doors that lead to the back deck overlooking the expansive, spectacular yard.Two extra large sheds in backyard for storage, a gazebo with deck space, and a courtyard with grilling station make this property an entertainers dream. This property is situated in a neighborhood that can support a 3M home; close to Vinson Owen elementary. Build equity and create the home of your dreams with a custom renovation & plenty room for a pool! Builders lined up and available to work directly with buyers!

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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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14 Risley Road Winchester MA 01890

Winchester, MA14 Risley Road

Price$1,799,000

Est. Mortgage: $/month

MLS Number 72913415

  • Single Family Detached
  • Village East Hill
  • Rooms 10
  • Bathroom 4
  • Bedrooms 4

Exquisite custom built center entrance colonial in East Hill, beautifully re-envisioned, gutted & rebuilt w/expansive addition in '05 boasts 3 impressive levels of thoughtfully designed amazing space that reflects beauty & warmth in every detail. Gracious 1st level w/its easy flow & well-appointed living area is highlighted by fine features+ that will surprise & delight at every turn. (See tour/list). Elegant DR opens to large kit w/sleek granite counters & island, custom maple cabs & dining area w/sliders to lovely patio & yard: THE PLACE to relax & entertain. Kit flows seamlessly to spacious FR w/cath ceiling, custom windows & doors that also lead to patio. LR has Fr doors to in-demand home office. MBR suite w/walk-in closet & chic bath, plus 3 BRs w/double closets & spa bath await on 2nd level. Fin lower level with inlaw potential has full bath & access to 2C gar. Fab expansion possibilities in walk-up attic. Close to town Center, T, schools & Fells, close to 93 & minutes to Boston.

Listed by Cynthia Frate of RE/MAX Andrew Realty Services

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$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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 10/28 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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

Active With Contract

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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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7 Wainwright Road Winchester MA 01890

MLS Number 72910344

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 4,228
  • Complex The Ledges

Welcome to the "The Ledges" - Custom Builder-Designed “E” Style - 11+ Room Townhouse - End Unit - exclusive Custom Layout - like no other at The Ledges - beautifully maintained and updated with exquisite details and features throughout - Open Floor Plan - Gourmet Chef's Kitchen - Cathedral Ceilings - Wainscoting and Crown Molding - two Decks overlooking private wooded area - New Custom Built-in Cabinetry throughout - abundant storage. 1st Flr - Sun-filled Living Rm - Dining Rm - Family Rm w/FP and Sliders to Private Deck - Custom Built Gourmet Kitchen w/all the Bells and Whistles - Office - Half-Bath - Master BD w/Gas FP - Slider to Private Deck - two Walk-in Closets and Master Bath w/double-Vanity. 2nd floor has a fabulous Loft - Bedroom and full Bath. Lower Level is completely finished - Custom Built-In's - Walkout Sliders to Private Yard - perfect Nanny/In-Law/Guest Suite. Premier Location near Club House - Pool and Tennis Courts. Minutes to Winchester Center and Major Routes.

Listed by Lucille Murray of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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
  • Bathroom 3
  • Rooms 9
  • 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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