Homes for Sale Winchester MA

Homes in Winchester are popular for families and professionals who work in the greater Boston area. The community offers plenty of recreational opportunities and is located just 9 miles northwest of Boston. Types of homes range from Colonials and Victorians to custom homes and newer construction.

Search all homes for sale in Winchester MA below. Visit our About Winchester page to learn more about living here. Please contact us if you have questions or would like to set up a showing! Register for an account to keep track of your favorite listings and for new property email notifications.‚Äč

View other Winchester property searches:

 All Winchester Real Estate  |  Winchester Condos  |  Multi-Family Homes in Winchester

 

422 MAIN Street, Winchester, MA

Price$1,085,500

Est. Mortgage: $/month

Open House

MLS Number 72341362

  • Single Family
  • Next Open House: Sun 22nd 1:00 pm - 2:00 pm
  • Parking Spaces 3
  • Year Built 1880
  • Full Bath 2

Stunning residence in town center located on esteemed Main Street in Winchester! Exquisite architectural detail throughout & designed for comfortable family living as well as stylish entertaining highlighted by large scale rooms with pocket doors; oversized windows with light streaming in from all directions; hardwood floors & high ceilings. The main floor features an open concept renovated kitchen/living room with adjacent mud room & laundry; an elegant dining room; foyer & charming farmer’s porch. 2nd fl offers magnificent renovated bath & 3 corner bedrooms and office. The real treat is 3rd floor master suite with stunning bath, walk in closet & sitting/exercise room. Amenities list is expansive for this extremely well-maintained home: multi-zone gas heating & central air; double closets in bedrooms; fully fenced rear yard; off-street parking; newer systems; generous storage & so much more. Walking distance to schools, train & downtown Winchester shops & restaurants!

Listed by Nancy Ciampa McLaughlin of Redfin Corp.

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 A VisitAsk A QuestionMore Details

185 Mystic Valley Parkway, Winchester, MA
Open House

MLS Number 72347765

  • Single Family
  • Next Open House: Sun 22nd 11:30 am - 1:00 pm
  • Parking Spaces 3
  • Year Built 1859
  • Full Bath 1

With its premier downtown location, enjoy all that Winchester has to offer just out your front door! Beautifully situated on a picturesque, tree lined street, the home is just minutes from Winchester’s Victorian downtown’s shops and restaurants, award-winning schools, and Commuter Rail station. Built in the 1850s, this historic Colonial features high ceilings, wide pine flooring, and newer windows. This is the perfect opportunity for a savvy buyer to modernize and restore the property to its original glory. Enjoy summer barbecues on the secluded backyard patio and near-limitless outdoor activities are yours to explore in the Middlesex Fells Reservation. A unique opportunity to own a special home.

Listed by Stephanie Walsh and Monika Kordowska of Better Homes and Gardens | The Shanahan Group

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

1 Woodside Road, Winchester, MA

Price$1,349,000

Est. Mortgage: $/month

MLS Number 72349385

  • Single Family
  • Parking Spaces 2
  • Village Flats
  • Year Built 1895
  • Full Bath 3

Welcome to the Flats! Beautiful 1895 Colonial on a 12,000sqft lot, just 1mile from the town center. Private and serene back yard with a blue stone patio and new 6ft cedar fence located directly off the kitchen. Sprinkler system and NEW 2-car garage with a 22x14 2nd floor just waiting for your imagination to finish. An inviting front porch opens into the grand foyer with a classic staircase. Bright, sun-drenched double parlor with lovely built-in details. Formal dining room, kitchen with granite counters/island, gas stove, stainless steal appliances and half bath complete the 1st floor. The second floor offers a master bedroom with new wood floor, walk-in closet, beautifully updated master bath, three additional bedrooms and large family bath. Third floor is wonderful space with full bath, 2 bedrooms and ample storage. The partially finished lower level is great flex space with even more storage options. Great home in a fantastic location...come enjoy all Winchester has to offer!

Listed by Catherine Albiani and Carrie Simpson of Century 21 Commonwealth

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

42 Cabot Street, Winchester, MA

Price$2,175,000

Est. Mortgage: $/month

Open House

MLS Number 72351616

  • Single Family
  • Next Open House: Sun 22nd 12:30 pm - 1:30 pm
  • Parking Spaces 6
  • Year Built 1920
  • Full Bath 4

Stunning Colonial Revival from the 1920's, which was renovated and restored by the popular TV Show and website "This Old House" in 2002. Combining the most modern and exquisite details, this 5 bedroom, 4.5 bath home is sure to amaze you! Complete with an elegant dining room with custom built-in shelves, formal living room w/ fireplace and gorgeous beamed ceiling, an inviting sunroom and immaculate eat-in kitchen featuring stainless steel appliances, gas stove and pantry with wine refrigerator. Steps up to the 2nd floor, you will find 3 generously sized bedrooms and 2 full baths; inclusive of the master suite with dream walk-in closet and renovated master bath. The 3rd floor boasts 2 additional bedrooms, a cedar closet and full bath. The finished lower level contains a media room, full bath, laundry room and ample storage. During the warmer months, escape to the serene fenced in backyard setting. With a 2 car garage and incredible location in the Flats, make this magnificent home yours!

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

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 A VisitAsk A QuestionMore Details

87 Grove Street, Winchester, MA

Price$899,000

Est. Mortgage: $/month

Open House

MLS Number 72342084

  • Single Family
  • Next Open House: Sat 21st 11:00 am - 1:00 pm
  • Parking Spaces 8
  • Year Built 1942
  • Full Bath 1

LOCATED IN A COVETED NEIGHBORHOOD close to West Medford and the commuter rail to North station. This spacious sunny home is surrounded by a stone wall, lush lawn & mature plantings. The large eat-in, kitchen with light cherry cabinets, center island & top of the line stainless appliances is the heart of the home. Entertain with elegance in the formal dining room with built-in China cabinet & abundant natural light. Huge front to back fire placed living room, screened porch & 1/2 bath complete the first floor. Neutral paint colors with hardwood floors let you make it your own! The second floor has 3 bedrooms with hardwood floors, built in storage, window seat & a recently updated bathroom. Convenient 2nd floor laundry next to heated bonus room provides expansion potential. Heated, finished basement with fireplace. Morning coffee or afternoon barbecue on the large deck overlooking expansive yard. 15k sq. ft. lot. New hot water heater & Bosch dishwasher. Don’t miss this one!

Listed by Camille Murphy of William Raveis R.E. & Home Services

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

15 Cardinal Street, Winchester, MA

Price$924,900

Est. Mortgage: $/month

Open House

MLS Number 72362368

  • Single Family
  • Next Open House: Sat 21st 12:00 pm - 1:30 pm
  • Parking Spaces 4
  • Year Built 2015
  • Full Bath 3

Gorgeous sun filled townhouse located on quiet cul-de-sac will live more like a single family. So much space w/private yard & driveway.Beautiful gourmet kitchen w/ large marble island,countertops, stainless steel appliances. Open floor plan w/ dining area to living room featuring fireplace & custom bookshelves. Office on the main floor features french doors & custom bookcases. Master bedroom has a beautiful master bath & custom walk in closet w/ expansive shelving/drawers.Two more bedrooms, a full bath and laundry closet finish the upstairs. The delightful finished basement features a family room, children's art/play area and another bonus room & bath for guests.Off the first floor mudroom is the back deck & pretty new patio to enjoy the professionally landscaped yard w/ new plants & fruit trees and shed.This neighborhood in the Muraco school district is near the bike path, the Fells, KidStock, ballet school and Russian math to name a few.Don't miss this beauty.

Listed by The Synergy Group and Susan Silkes of Leading Edge Real Estate

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

36 Chester Street, Winchester, MA

Price$699,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72362451

  • Single Family
  • Parking Spaces 3
  • Year Built 1860
  • Full Bath 1
  • Bathroom 2

New to the market! Solid mid 1800 Colonial style home in need of upgrades and clean up located on a quiet tree lined street within close proximity to all of Winchester's amenities and a short walk to Muraco Elementary School. Location and land make this an opportunity for a contractor to upgrade. Being offered as is. This is a flipper's dream! Perfect opportunity to modernize and restore the property to its original glory. A rare and unique diamond in the rough with unlimited potential to be enjoyed by a new generation. Offering a level fenced in backyard perfect for those summer barbecues with plenty of off street parking. Perfect opportunity to set up roots in one of the most sought after communities minutes from Boston!

Listed by Robin Dunbar Bain and Paula Savard of Aberman Associates, Inc.

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

5 Nelson Street, Winchester, MA

Price$699,900

Est. Mortgage: $/month

Open House

MLS Number 72366040

  • Single Family
  • Next Open House: Sun 22nd 11:30 am - 1:30 pm
  • Parking Spaces 2
  • Year Built 1887
  • Full Bath 2

Picture Perfect Colonial in downtown Winchester neighborhood. This beautiful and bright home has it all! Full of character and charm, this home features 3 bedrooms, 2 full remodeled bathrooms, a stunning kitchen with stainless steel appliances, beadboard ceiling, granite countertops and wide board hardwood floors with first floor laundry. Extra space in the lower level is great for a playroom or office. Close to train, schools and Winchester Center! Showings to begin at Open House 7/22 11:30-1:30.

Listed by Stephanie Mcgowan of Waterfield Sotheby's International Realty

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

50 Glen Road, Winchester, MA

Price$1,299,000

Est. Mortgage: $/month

MLS Number 72337402

  • Single Family
  • Parking Spaces 4
  • Year Built 1896
  • Full Bath 2
  • Bathroom 3

Beautifully renovated 19th century colonial unites the gracious elegance of yesterday with the modern amenities of today. One of Winchester's premier neighborhoods, Glen Road is a quaint one-way street close to downtown, schools and the train to Boston. The attached two car garage addition features a plumbed, unfinished second level with a separate entrance~ perfect for future in-law, home office or au pair space. The stunning white marble gourmet kitchen with over sized island enjoys a double wall oven, Wolf range, Sub Zero refrigerator and drawers, a large walk-in pantry with bar sink and a beverage refrigerator. The informal dining area, mudroom and office flow easily from the kitchen into a bright and open combination family/formal dining room with fireplace and sun room. The professionally landscaped yard with custom stonework and private patio add to the homes classic curb appeal.

Listed by Cynthia Houle of Century 21 Commonwealth

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

700 Washington Street, Winchester, MA

Price$1,049,000

Est. Mortgage: $/month

Open House

MLS Number 72304452

  • Single Family
  • Next Open House: Sat 21st 12:00 pm - 1:00 pm
  • Parking Spaces 8
  • Year Built 2000
  • Full Bath 2

ABSOLUTELY GORGEOUS - GUTTED and COMPLETELY RENOVATED in 2000 - Colonial Farmhouse w/Farmer's Porch, OVERSIZED two-car Garage w/large LOFT, Shed, beautifully landscaped, Cedar Fenced Yard, 23,621 sq' Lot. Updated and has preserved some original details and character. Main floor features Open Floor Plan w/spacious Foyer & Staircase, lg Mudrm w/Walk-in Closet, updated Quartz Kitchen w/High-end Appliances and lg Island, Gracious Living Rm w/Fireplace and sun-filled Dining Rm. Second flr has three Bedrms including lg Master Bedrm w/full Bath and two Custom Closets one of which is a Walk-in Closet, Laundry Rm and another full Bath. Third floor has a lg Bedroom ideal for NANNY/IN-LAW Suite. Minutes to Muraco School, Parks, Winchester Center, Commuter Train and steps to the future Tri-City Bike Path. Enjoy Winchester and all its Amenities, including Schools, Shops, Restaurants and easy access to Rtes 93 &128. One of the BEST LOTS in Winchester and the BEST VALUE Home in this price range.

Listed by Lucille Murray of Leading Edge Real Estate

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

3 Brookside Avenue, Winchester, MA

Price$769,900

Est. Mortgage: $/month

Open House

MLS Number 72363094

  • Single Family
  • Next Open House: Sat 21st 1:00 pm - 2:30 pm
  • Parking Spaces 3
  • Year Built 1940
  • Full Bath 1

Classic New England Cape located in the popular Muraco School section of Winchester! This 3 bed, 1½ bath home offers a fantastic opportunity to become part of the Winchester community. This well-maintained home has updated systems, newer windows, hardwood floors & charming details including; crown molding, marble faced fireplace & built in cabinetry. The first level offers an expansive formal living room w/ a stunning fireplace that flows into the dining room, kitchen, half bath & a private sun filled office. You’ll love the convenient side entrance from the kitchen leading you to an enclosed breezeway/mudroom & attached garage. On the second level are 3 spacious bedrooms, full bath & bonus room which would make an excellent playroom, office or guest bedroom. Basement offers additional room for storage or expansion. Enjoy the private fenced in backyard with patio, storage shed & a wonderful location w/ easy access to both Route 93 & 95, restaurants, shops & public transportation.

Listed by Theuer, Pirani & Wile and Julie Wile Fish of Leading Edge Real Estate

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

85 Loring Avenue, Winchester, MA

Price$809,900

Est. Mortgage: $/month

MLS Number 72365545

  • Single Family
  • Parking Spaces 4
  • Year Built 1962
  • Full Bath 2
  • Bathroom 3

This home has been lovingly maintained and updated and is in mint condition Bright sunny granite kitchen and family room overlook private yard.Living room and dining room have gleaming hardwood floors. Three bedrooms on the second floor have spacious closets. Full basement has a large recreation room with fireplace and full bath. Central air,newer windows and gas heat are just a few of the amenities of this wonderful home.Located conveniently to a park, bike path and a short distance to major highways. This is a Lynch School neighborhood . Move right in and enjoy!

Listed by Nan Shanahan of Better Homes and Gardens | The Shanahan Group

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

51 Wedgemere Avenue, Winchester, MA

Price$1,799,000

Est. Mortgage: $/month

Open House

MLS Number 72365181

  • Single Family
  • Next Open House: Sat 21st 12:30 pm - 2:30 pm
  • Parking Spaces 4
  • Village The Flats
  • Year Built 1914

Don’t miss this rare opportunity to live on one of the most desirable streets in the “Flats". Seldom do you find homes like this charming English Tudor for sale. This home has everything you could want and more! The grand entrance has an elegant fireplace w/hand carved mantel & leads to a front to back lv rm & 2nd stunning fireplace w/built-in bookcases. Off lv rm is a wonderful & bright Sunroom. An elegant dnrm has plenty of space for small & large gatherings. Hand painted ceiling adds charm to this room. Original butler’s pantry opens to spacious updated kitchen. Washer & dryer on main level & elegant half-bath. Completing this level spacious Family Room. The 2nd level has oversized landing which leads to 4 bdrms including master bedroom.Original claw foot tub & separate shower are delightful. The 3rd level 2 add'l bdrs & bath - lower level has a lg bonus rm & 1/2 ba - private yard w/bluestone patio. Two car garage. Location, character & space describes this gorgeous home

Listed by Janet Halloran of Leading Edge Real Estate

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 A VisitAsk A QuestionMore Details

200 Cross Street, Winchester, MA

Price$739,900

Est. Mortgage: $/month

MLS Number 72365132

  • Single Family
  • Parking Spaces 3
  • Year Built 1950
  • Full Bath 1
  • Bathroom 2

Muraco School District !! This 3 bedroom, 1 1/2 bath Cape style home is very deceiving from the outside. So much more room than you'd think. Formal living room has wall to wall carpet over the hardwood floors. Cabinet packed kitchen, formal dining room with parquet floors, the first floor bedroom is being used as an office. Full bath. Upstairs finds two large bedroom with large closets and there is a half bath. Hardwood floors in all rooms.The basement area is finished with a laundry room with cabinets, a sink and a refrigerator. There is a family room and another office area. A plus is the storage room and extra storage under the stairs. Walk out the basement to the large back yard which has a patio and a shed. The home is close to everything -train, bus, downtown, schools. Purchase now and be in your new home in time for school. Open House Saturday 12-2 pm and Sunday 12-2 pm.

Listed by Patricia Marsh of Realty Executives Marsh & Associates

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

14 Aristotle Drive, Winchester, MA

Price$2,230,000

Est. Mortgage: $/month

Open House

MLS Number 72337313

  • Single Family
  • Next Open House: Sun 22nd 1:00 pm - 3:00 pm
  • Parking Spaces 6
  • Year Built 1998
  • Full Bath 4

Rare offering! A secluded residence exceptionally sited above a verdant conservation area among an enclave of new homes. This elegantly appointed home has been transformed inside & out with new systems & extensive improvements that enhance every room. High ceilings, open spaces, & walls of windows seamlessly integrate interior & exterior spaces offering the ultimate enjoyment for today’s indoor-outdoor modern lifestyle! Amenities include: 3 car attached heated garage, gracious two story entry hall w/ formal rooms, expansive chef’s kitchen, library, & sun splashed family room w/magnificent stone fireplace & views of the lush gardens, stone-scape & natural habitat beyond – simply indescribable! Second floor offers five bedrooms including a master suite & au pair wing. Walk out lower level offers an open game room/play room; gym & new music room provide versatility for those who need add’l bedrooms. Minutes to downtown Winchester! Extensive list of improvements are attached.

Listed by Lorrie Parajeckas of Century 21 Commonwealth

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 A VisitAsk A QuestionMore Details

104 Hillcrest Parkway, Winchester, MA

Price$1,250,000

Est. Mortgage: $/month

MLS Number 72347971

  • Single Family
  • Parking Spaces 4
  • Year Built 1926
  • Full Bath 2
  • Bathroom 3

Welcome to 104 Hillcrest Parkway! Located directly across from the breathtaking Middlesex Fells Reservation. This picturesque street truly is one of the most enticing in all of Winchester. Home has been exceptionally maintained and is bursting with character. Main level is ideal for entertaining with it's brilliant open floor plan and stunning hardwood floors. Massive family room with gorgeous built in book cases, eat-in kitchen, mudroom with a slider to the patio. There is also a living room with a gas fireplace, elegant dining room, and an office with it's own half bath. Sprawling master suite has 2 walk-in closets, and a balcony overlooking the backyard. Bonus heated room above the 2 car garage offers a variety of uses. Ecostar Majestic Slate roof is environment-friendly and super efficient. Central A/C, newer hot water heater, main level laundry and more. Winchester has a superior school system, easy access to Boston, and a great downtown area. The perfect town to raise a family!

Listed by Ryan Mirisola of Premier Homes Real Estate

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 A VisitAsk A QuestionMore Details

86 Church Street, Winchester, MA

Price$1,849,000

Est. Mortgage: $/month

Open House

MLS Number 72364668

  • Single Family
  • Next Open House: Sun 22nd 1:00 pm - 3:00 pm
  • Parking Spaces 7
  • Year Built 1890
  • Full Bath 3

Stunning and timeless, this beautiful Victorian masterfully blends high-end updates with exquisite period details, such as gorgeous leaded windows and a superb original pocket door in the dining room. Newly renovated designer kitchen features Thermador appliances, Perlick beverage fridge, custom cabinetry, gas fireplace, and reclaimed heart pine flooring. Meticulously chosen finishes like grass cloth wallpaper, custom window treatments, antique and modern lighting create spaces that welcome and delight. Generous bedrooms on the 2nd and 3rd levels, including the serene master retreat, have ample closets and are freshly updated; 3 remodeled baths impress. Sizable lower level bonus room is perfect for movie night, working out and entertaining. Brand new modern office is handsomely designed down to the last detail, flooded w/natural light and set away from main house for privacy. Lovely backyard oasis; wonderfully close to Center’s vibrant restaurants, shopping, schools and train stations

Listed by Stephanie Mcgowan of Waterfield Sotheby's International Realty

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

47 WAINWRIGHT Road, Winchester, MA

Price$2,499,900

Est. Mortgage: $/month

MLS Number 72333078

  • Single Family
  • Parking Spaces 6
  • Year Built 2007
  • Full Bath 5
  • Bathroom 7

Quality construction, dramatic architecture, elegant details and lavish appointments, this beautiful custom built residence is sited on a private lot in a very desirable location with everything that Winchester has to offer. A perfect blend of formal space and comfort. The gourmet kitchen features a breakfast room that leads to an outdoor patio, perfect for entertaining family and large gatherings. A grand staircase leads you to all en-suite bedrooms on the second floor. The Master Bedroom features a spa- inspired bath and walk in closets. 3 additional bedrooms with en-suite baths and walk in closets complete this level. This is a unique buying opportunity for this type of quality that is only found in custom built homes. Here is your chance to make it yours!

Listed by Dorothea Feffer of Coldwell Banker Residential Brokerage - Winchester

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

45 Mystic Valley Parkway, Winchester, MA

Price$1,599,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72339488

  • Single Family
  • Parking Spaces 3
  • Year Built 1910
  • Full Bath 2
  • Bathroom 3

This is the one you’ve been waiting for! Classically renovated turn of the century colonial steps from Wedgemere station and walking distance to schools and downtown. First floor includes custom chef’s kitchen with huge teak island, inset cabinetry, and Thermador appliances. Formal dining room is highlighted by wainscoting and built-in china cabinet. Large foyer off the enclosed front porch leads to a front to back living room with built in bookcases and working fireplace. Also on the first floor is a bright family room space with access to a large covered back deck and bluestone patio. Other features include two-car garage and professionally landscaped yard with irrigation. Upstairs are four spacious corner bedrooms, including master with en-suite bathroom and his/hers walk-in closets. Do not miss the full walk up attic with renovation ready fifth bedroom; potential for master bedroom suite conversion.

Listed by James L. Freeman of Freeman Realty Associates, Inc

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

3 Thornberry Road, Winchester, MA

Price$1,499,000

Est. Mortgage: $/month

MLS Number 72320737

  • Single Family
  • Parking Spaces 6
  • Year Built 1959
  • Full Bath 2
  • Bathroom 4

Prominently situated in the highly sought after Vinson Owen School District, this impressive West-Side Colonial has been architecturally redesigned + finished with the highest level of quality throughout. Glowing with sun-light, the sprawling first floor features a sumptuous living room w/ wood-burning FP + marble hearth, gallery style recessed lighting and great ceiling height, idyllic home office/ den and elegant marble powder room; Picture perfect chef's kitchen boasts Custom Cabinetry, Bosch Appliances, Bar Seating, Statuario Quartz Counters, tiled geometric backsplash + separate formal dining. Sun-Room w/ Montauk Blue tile + beadboard ceiling. Upper level offers 3 well-placed BR's + kids bath; super luxe Master Wing outfitted w/ custom built-ins, walk-in + linen closet + SPECTACULAR Italian Marble Bath. Media Room/ Yoga Studio is sun-filled w/ fireplace, Shiplap, 1/2 bath + laundry Blue Stone Patio, Deck + Huge Yard. All new or newer (heating/cooling/water/ electrical) systems.

Listed by Allison Shannon of RE/MAX Luxury Living RE

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

312 Washington Street, Winchester, MA

Price$889,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72360757

  • Single Family
  • Parking Spaces 3
  • Village Muraco
  • Year Built 1880
  • Full Bath 2

Finally! A fabulous, beautifully renovated home that you can afford in the coveted Muraco District! This one is a gem. Open and airy farmhouse sits on a gorgeously landscaped lot highlighted by a stone patio with a fire pit, lovely mature plants and a huge deck off the kitchen. The interior shines with sleek lines in the open, modern kitchen, dining room and family room. Antique wood floors have been perfectly restored, taking the design element of this home to a really beautiful height. There are 4 bedrooms, second floor laundry, sleek bathrooms and full dry basement for storage. There is also a big farmers porch to relax on as you sip your coffee, and lots of driveway space. BONUS: Solar panels (owned, not rented) keep electric bills extremely low (see attached utility bills). Close to town, schools, trains, the Fells and highway. Open Sat & Sun!

Listed by Nancy S. Pallotta of Leading Edge Real Estate

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

101 Harvard Street, Winchester, MA

Price$679,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72358216

  • Single Family
  • Parking Spaces 3
  • Year Built 1880
  • Full Bath 1
  • Bathroom 2

Extensively renovated in 2012, this home has all of the amenities you’d wish for. Located at the end of a dead end street w/ proximity to all of Winchester’s amenities & just a brief walk to Muraco Elementary. Greeted by a charming farmers porch, perfect for your morning coffee or to relax on after a long day. The 1st floor has a wonderful open layout containing a living room, adjoining dining room w/ a kitchen pass-through window to the completely renovated kitchen featuring a gas stove, stainless steel appliances, granite countertops & recessed lighting. The ½ bath & laundry room complete the 1st floor. The 2nd floor boasts 3 generously sized bedrooms, a full bath & a 4th room that could serve as an office or nursery. Containing an unfinished lower level, this home has plenty of room for future expansion. Offering a level fenced-in backyard & plenty of off-street parking, take this opportunity to establish your family in one of the most sought after communities in the Boston area.

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

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 A VisitAsk A QuestionMore Details

14 Ardley Road, Winchester, MA

Price$1,395,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72342179

  • Single Family
  • Parking Spaces 6
  • Year Built 1940
  • Full Bath 3
  • Bathroom 3

Perfectly situated on an oversized lot, this beautifully designed home is move in ready! Renovated and expanded from the original, this home combines classic charm with modern design. The first floor features an open floor plan with European inspired kitchen, breakfast bar, dining area and gas fireplace family room ideal for entertaining w/sweeping views of the picture perfect yard. Three bedrooms on the second floor including cathedral ceiling master w/ Juliet balcony, walk-in closet, and private bath. Enjoy summer days on the sun deck off family room or in the gorgeous back yard with patio. This home also features a first floor bedroom with adjacent full bath. Formal living room with wood burning fireplace, family room with gas fireplace & 3 car under garage~ Located only 7 miles from Boston, nearby commuter line, minutes from Lynch Elementary and Horn Pond. Walking path to the Lynch elementary school from back yard! This spectacular home is a MUST SEE!

Listed by Kim Covino of Leading Edge Real Estate

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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

47 Arlington Street, Winchester, MA

Price$2,245,000

Est. Mortgage: $/month

Open House

MLS Number 72343357

  • Single Family
  • Next Open House: Sun 22nd 12:00 pm - 1:00 pm
  • Parking Spaces 6
  • Year Built 2000
  • Full Bath 5

Stunning Colonial set in the heart of Myopia hill w/ serene golf course views & an impeccably landscaped yard, which affords privacy & tranquility. From the minute you walk in, your eyes will be drawn to the magnificent bridal staircase. A room for every occasion, this home is perfect for all of your entertaining needs. Featuring an elegant living room w/ double sided gas fireplace which leads into the den, a 1st floor bedroom w/ private bath & an open-floor family room w/ cathedral ceilings & a gorgeous stone fireplace. The chef inspired kitchen has upgraded, high-end appliances, an oversized island w/ granite countertops & dining area. A formal dining room & wet bar complete the 1st floor. The 2nd level boasts 4 spacious bedrooms, inclusive of the master suite w/ soaring ceiling heights, his & her closets & large master bath. The lower level is complete w/ a recreation room, full bath, exercise room & media room. With a 3 car garage & incredible location, make this dream home yours!

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

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 A VisitAsk A QuestionMore Details

10 Ledgewood Road, Winchester, MA

Price$2,945,000

Est. Mortgage: $/month

Open House

MLS Number 72337357

  • Single Family
  • Next Open House: Sat 21st 11:30 am - 1:00 pm
  • Parking Spaces 9
  • Year Built 2004
  • Full Bath 4

NEW LISTING! This Grand Estate is located in one of Winchester's most prestigious neighborhoods~ This private residence "Dream Home" was custom built with every amenity and will exceed your expectations. Situated on an acre w/ level manicured grounds, gunite pool w/ fence and auto cover for safety. Large mahogany deck and patio ideal for outdoor entertaining. Enormous state of the art chef's kitchen, freshly updated white quartz, custom cabinetry, oversized island, desk & breakfast bar. Sun-drenched breakfast room w/floor to ceiling windows overlooking expansive rear yard. Game room, gym, sports room with padded walls, media theatre room, and so much more! This exquisite residence features floor to ceiling Pella French doors & windows,10FT ceilings w/ double crown moldings, 3 fireplaces, 3 car garage. Seldom does such a magnificent estate come on the market with such privacy & beauty w/ easy access to Fells reservation, Winchester center shops, restaurants, schools & train to Boston

Listed by Kim Covino of Leading Edge Real Estate

{$office->Name}

Better Homes and Gardens | The Shanahan Group
552 Main Street
Winchester MA, 01890
Office: 781-729-9030

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.52% last updated on Jul 19, 2018
* 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 A VisitAsk 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.