Winchester Real Estate

Just 15 minutes northwest of Boston is the beautiful town of Winchester, MA. When your kids are on summer vacation from Winchester's top-ranked public school system, have them spend time sailing at the Winchester Boat Club, keeping fit at the Winchester Swim and Tennis Club, or golfing at the Country Club. A quick trip on the Communter Rail's Purple Line will drop you right at the Fleet Center in central Boston, perfect for easy commuting to work or for an evening out. Don't miss out on D'Agostino's Deli, a famous local spot for subs, sandwiches, party trays, and more delicious deli wonders.

And Winchester real estate doesn't disappoint: find many new construction single-family homes, historic estates, luxurious condos, and more.

View currently listed real estate in Winchester below and contact Century 21 Advance Realty with any questions or to schedule a tour. You can also register with our site to save your favorite properties and receive notifications via email when a new listing matches your preferred criteria. 

5 A Fernway Winchester MA 01890

Winchester, MA5 A Fernway

Price$3,495,000

Est. Mortgage: $/month

MLS Number 72884501

  • Single Family Detached
  • Village Myopia Hill
  • Bathroom 6
  • Rooms 12
  • 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: 2.86% last updated on Sep 16, 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: 2.86% last updated on Sep 16, 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$2,599,000

Est. Mortgage: $/month

MLS Number 72890643

  • Single Family Attached
  • Bedrooms 5
  • Rooms 7
  • Bathroom 4
  • Square Feet 4,511

For the first time in over 25 years presents the rare opportunity to acquire one of the most exclusive and private lots in Winchester. The 1 acre property sits on an immaculately manicured landscape. Laid out with a wide open floor plan, creating endless opportunity for any family. Floor to ceiling windows fill the home with an abundance of natural light. 4 bedrooms, 2.5 bathrooms and an attached in-law suite which includes a full bathroom, kitchen / cabinetry, with access from the garage and private exterior access. The kitchen includes four ovens, gas stove, a skylight and double sliding glass doors that leads to the back deck filling the room with natural light throughout the day. Two extra large sheds in backyard for storage. Four water fountains, gazebo with deck space, and a courtyard with grilling station make this property an entertainers dream. 3 min walk to Vinson Owen Elementary School. House also features a large indoor pool that's currently covered but can be reopened.

Listed by Kevin Diarbakerly of Christine Boncore

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$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 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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34 Ginn Road Winchester MA 01890

Winchester, MA34 Ginn Road

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72894624

  • Single Family Detached
  • Bedrooms 5
  • Rooms 15
  • Bathroom 5
  • Acreage 0.39

COOK THANKSGIVING DINNER IN YOUR BRAND NEW KITCHEN! New construction home with an estimated completion date of November 2021. Local master builder brings another winning design to Winchester. Showing off both vertical & horizontal siding and featuring a metal roof over the front porch. This home will be loaded with high tech bells and whistles for modern conveniences. Just shy of 6,000 square feet, there's plenty of space for the family to spread out on 4 different floors. The phenomenal master wing boasts a sitting-library-dressing room with gas fireplace, a separate bedroom with soaring ceilings, a to-die-for walk in closet and gorgeous bathroom. Start your day with a workout in your downstairs gym. Multiple locations to set up a home office. There's even a secondary master suite on the 1st floor, perfect for overnight guests. The hardscape features spectacular stone work including a fire pit for those up coming cooler evenings. 2-Car garage and ample parking.

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 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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$
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$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 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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5 Bacon Street Winchester MA 01890

Winchester, MA5 Bacon Street

Price$1,899,999

Est. Mortgage: $/month

MLS Number 72855858

  • Multi-Family 2 Family
  • Total Parking Spaces 4
  • Year Built 1910
  • Bathroom 4
  • Full Bath 4

The timeless craftsmanship of this home has been preserved & updated to keep it as beautiful today as the day it was built! Both units of this home have been tastefully & thoughtfully renovated by the same family so that they seamlessly complement each other while keeping the original characteristics of the home intact. Sporting vintage style appointments, spacious fireplace living rooms, beautifully renovated kitchens, and dining rooms w/ built-in china cabinets, there's limitless personality in every room. This home can function as two separate units or one multigenerational home- separate enough to have plenty of privacy, but cohesive enough to feel like one space if preferred! Close to town center & Wedgemere Station. 9 foot ceilings, Many improvements include roof, electrical (knob & tube removed), hot water heaters, interior paint, exterior paint historic colors, gutters, exterior doors, storm windows - see list on link.

Listed by Anne Spry of Barrett Sotheby's International Realty

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$
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$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 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 Westland Avenue Winchester MA 01890

Winchester, MA8 Westland Avenue

Price$1,700,000

Est. Mortgage: $/month

Open House

MLS Number 72894282

  • Single Family Detached
  • Next Open House: Sat 09/18 11:00 am. to 1:00 pm.
  • Bathroom 3
  • Rooms 11
  • Bedrooms 4

Sumptuously landscaped modern colonial radiates an ambiance of comfortable elegance throughout: high ceilings, gleaming hardwood floors, 3 fireplaces, & a spacious, versatile floor plan for everyday living & entertaining. The sensational living room has soaring ceilings, walls of windows, & an impressive wood burning fireplace. The large sun-splashed eat-in kitchen features custom cabinetry, peninsula seating, granite counters, ss appliances, & a vaulted ceiling w/skylight. The kitchen is open to the sunroom, & a circular flow connects all 1st floor rooms including a formal dining room, office, & half bath. 2nd floor has 4 bedrooms, 2 full baths, & features a primary bedroom w/cathedral ceilings, dramatic windows & fireplace. Lower level has a finished media/game room & playroom. Exterior amenities: a 2-tiered deck, koi pond, & treehouse. Two-car detached garage w/storage. Ambrose Elementary location; close to Winchester center w/two commuter rail stops. Welcome to your forever home!

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 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: Fri 09/17 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: 2.86% last updated on Sep 16, 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
  • Bathroom 3
  • Rooms 10
  • Bedrooms 4

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: 2.86% last updated on Sep 16, 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$1,600,000

Est. Mortgage: $/month

Open House

MLS Number 72896521

  • Single Family Detached
  • Next Open House: Sat 09/18 11:30 am. to 1:00 pm.
  • Village West Side
  • Bedrooms 4
  • Bathroom 3

Welcome to this tastefully remodeled 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: 2.86% last updated on Sep 16, 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

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.