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Homes for Sale Winchester MA

Winchester, Massachusetts is 8 miles north of Boston. Winchester is child-friendly and home to lakes, parks, and trails. Winchester keeps its public spaces well maintained. Winchester is a family-friendly bedroom community. 

Discover Winchester Real Estate

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6 Stone Avenue Winchester MA 01890

Winchester, MA6 Stone Avenue

Price$849,000

Est. Mortgage: $/month

MLS Number 72924686

  • Single Family Detached
  • Bathroom 2
  • Bedrooms 3
  • Rooms 7
  • Square Feet 1,890

Welcome to 6 Stone Avenue, one of Winchester's most sought after locations. Just minutes to wonderful downtown, commuter train, Fells Conservation area, major commuting routes, shopping, restaurants and schools. This charming home highlights a sunny, open concept, lots of windows and high ceilings. The first floor features hardwood floors, a stunning chef's kitchen with direct access to dining room and large Timbertek deck. A double sided gas fireplace separates the dining room and main family/living area. Second floor highlights three roomy bedrooms and hardwood floors. Recreation/play/office/den room in the lower level. This home will not disappoint!

Listed by Elisa Spence of Keller Williams Realty Boston Northwest

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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41 Irving Street Winchester MA 01890

Winchester, MA41 Irving Street

Price$799,000

Est. Mortgage: $/month

MLS Number 72924607

  • Multi-Family 2 Family - 2 Units Up/Down
  • Total Parking Spaces 8
  • Units 2
  • Full Bath 3
  • Bathroom 3

Excellent opportunity for owner occupants or investors! This spacious two-family home offers amazing potential in highly-sought after Winchester. The1st floor unit has been updated and features hardwood floors throughout, granite counters in the large eat-in-kitchen, bedroom w/walk-in closet and a heated sunroom. The owner's unit boasts a variety of options with 4 bedrooms, 2 full bathrooms, a formal dining room, living room, & bonus family room/home office adjacent to the bedroom on the main level. Both units have updated heating systems, electrical and windows. The backyard offers a new, above-ground pool just perfect for those hot summer days to come; the solar panels keep your electric bills to a minimum; and the oversized storage sheds are perfect for storing all your toys and tools. Located just under a mile to the Winchester train station (17 mins to N. Station!) the 2,500 acre Fells Reservation, and all of the shops & restaurants that Winchester Center has to offer!

Listed by Sarah Suarez of Gibson Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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44 Swanton Street Winchester MA 01890
Open House

MLS Number 72923290

  • Condo or Co-op
  • Next Open House: Sat 12/4 1:30 pm. to 2:30 pm.
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,174

MUST SEE two level condo located conveniently near Town Center! This updated and meticulously maintained 2 level condo is spacious with gorgeous hardwood floors throughout. First level of the condo has a bedroom with custom built-ins, formal open concept living and dining room with crown molding and custom built-ins. Bright and sunny family room opens to a chef's kitchen that has been updated to include stainless steel appliances, a kitchen island and upgraded custom cabinetry and countertops. Slider opens to a private back deck with great views and access to the oversized backyard. 2nd level features a massive master bedroom with custom built-in cabinets and ample storage in double closets. Two additional bedrooms and a full bathroom completes this level. Exterior has a paved driveway with 3 deeded parking and additional guest parking spaces. Close to shopping, restaurants, commuter rail and bike path! You cannot miss this opportunity for an incredible condo!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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124 Highland Avenue Winchester MA 01890

Winchester, MA124 Highland Avenue

Price$1,749,000

Est. Mortgage: $/month

Open House

MLS Number 72923268

  • Single Family Detached
  • Next Open House: Sat 12/4 1:00 pm. to 2:00 pm.
  • Bathroom 4
  • Rooms 14
  • Bedrooms 6

Welcome home to this quintessential Winchester Colonial. Located near the heart of Town Center and The Fells. This home has been meticulously maintained and updated. With a grand front entrance & an elegant foyer opening to a dining and family room with gorgeous hardwood floors, fireplace and built-in bookcase. A sitting parlor with fireplace is just off the fabulous chef's kitchen wonderful for entertaining. Featuring 2 ovens (Dacor, Gaggeau), Dacor gas stove, 2 sub-zero refrigerators including a 2 drawer, 2 sinks, 2 dishwashers (Bosch and Miele). 2nd & 3rd floors includes a total of 5 bedrooms w/ the addition of a master bedroom that includes an en-suite spa bathroom. 2 additional fully renovated bathrooms, two offices including a “sleeping porch” with one of the most beautiful sunset views in Winchester. Fantastic home for outdoor entertaining with a front porch, back bluestone patio, fire pit and a 2 car garage. Professionally landscaped w/ mature plantings. This is a MUST SEE home

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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261 Washington Street Winchester MA 01890

Winchester, MA261 Washington Street

Price$1,199,000

Est. Mortgage: $/month

Open House

MLS Number 72923330

  • Single Family Detached
  • Next Open House: Sat 12/4 11:30 am. to 12:30 pm.
  • Bathroom 3
  • Rooms 9
  • Bedrooms 4

Charming & tastefully redesigned Colonial has the curb appeal you've been looking for! This home has all the modern convenience for today's living including proximity to Winchester Center. The first floor has a cleverly designed mudroom with half bath. A spacious open concept living room boasts gorgeous hardwood floors, custom built-in cabinetry w/ a window seat and opens to a renovated chef's kitchen. The kitchen features stainless steel appliances, gas cooking, a kitchen island and ample storage. The dining room includes custom cabinetry and a wine refrigerator. 2nd floor has 3 spacious bedrooms and a fully renovated full bathroom. The 3rd floor has a bedroom that is a great option for a home office. Plenty of closets & storage space. Finished lower level has a fantastic space for a media room and play area. Includes laundry room and a full bathroom. Exterior features a welcoming front porch, entertainer's backyard patio that is fenced-in w/ a shed. Make this home yours!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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3 Fernway Winchester MA 01890

Winchester, MA3 Fernway

Price$1,599,000

Est. Mortgage: $/month

Open House

MLS Number 72923348

  • Single Family Detached
  • Next Open House: Sat 12/4 11:30 am. to 12:30 pm.
  • Bathroom 4
  • Rooms 8
  • Bedrooms 4

This elegant and expanded Cape home is a MUST SEE! Surrounded in lush landscaping, this home feels like being in an oasis. Formal entry opens to the spacious living room featuring a fireplace and French doors that open to the outdoor patio. Formal dining room is just off the kitchen making this convenient for entertaining. Impressive beamed vaulted ceilings in the kitchen and family room. Kitchen features double ovens and a paneled refrigerator. Oversized stone fireplace with a rustic mantle and French doors offer a second entry onto the outdoor patio from the family room. 2 Master Suites w/ spa like en-suite bathrooms. Completely renovated w/ high end finishes. 2nd floor bedroom is spacious enough for a sitting area and includes another full bathroom. Exterior boasts mature landscaping creating privacy, a 2 car garage with elevator and heated driveway, and a separate side parking pad available for overflow parking. This is truly a remarkable and stately home that is ready to be yours!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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20 Wildwood Street Winchester MA 01890
Open House

MLS Number 72923494

  • Single Family Detached
  • Next Open House: Sat 12/4 12:00 pm. to 2:00 pm.
  • Village Flats
  • Rooms 12
  • Bathroom 3

Located in the Flats - a mere half mile to the Winchester Town Center Commuter Rail & only .7 mile to Ambrose Elementary. This updated five-bedroom colonial is architecturally striking within a district known for alluring period homes. The interior blends the elegance of beamed ceilings, wainscotting, & 3 fireplaces with a modern comfortable décor. A circular flow connects formal living & dining rooms to the family room & kitchen, perfect for entertaining & everyday living. The eat-in custom kitchen w/granite counters & butcher block food prep peninsula adjoins a large mudroom/laundry area. Two staircases provide convenient access to 5 spacious 2nd floor bedrooms including a front to back primary bedroom w/walk-in cedar closet. Lots of areas for office/flex spaces on the 2nd floor, the sunlit 3rd floor bonus room, & finished lower level. A teakwood deck with a wisteria adorned pergola overlooks the spacious fenced-in backyard. 2 car attached garage. Numerous updates - list available.

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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 Ledgewood Road Winchester MA 01890

Winchester, MA32 Ledgewood Road

Price$2,799,000

Est. Mortgage: $/month

MLS Number 72921941

  • Single Family Detached
  • Bathroom 4
  • Rooms 10
  • Bedrooms 5
  • Acreage 0.3

NEW CONSTRUCTION!! Must see this gorgeous 4/5 bedroom home with thoughtful design & high end finishes! This luxurious home is spacious and inviting, offering a grand open floor plan ideal for entertaining and modern day family living. The kitchen features an oversized island with seating/ double thick quartz countertops, high-end thermador professional appliances, wine bar w/ fridge, breakfast nook/morning dining area. Off the kitchen is a spacious family room with gas fireplace and direct exterior access w/ sliders leading out to the large deck & private rear yard. The first floor also has a formal dining room and 5th bed OR home office with 3/4 bath. The second level master suite is a DREAM, offering a 2 room suite; bedroom with separate sitting room, dual walk-in closets, lavish bath with tiled shower/glass enclosure, double vanities & soaking tub! Three additional beds incl. junior suite w/ bath, full hall bath and a laundry room finish this level.oversized 2 car garage & mudroom.

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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50 Winford Way Winchester MA 01890

Winchester, MA50 Winford Way

Price$1,049,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72919584

  • Single Family Detached
  • Village East Side
  • Bedrooms 3
  • Bathroom 2
  • Rooms 8

Don't miss this opportunity! Create your dream home with this 3 bed expanded cape in top East Hill location overlooking conservation w/ easy access to the town forest trails! This lovingly maintained home with family room addition on the rear offers great space and has amazing potential w/ attached two car garage offering the perfect opportunity for expansion. Mudroom entry, generously sized living room with a wood-burning fireplace, dining room with original built-ins, PLUS a spacious family room with skylights that draws lots of natural sunlight w/ access to the private backyard. The first floor also offers a bedroom/study and 1/2 bath which could be expanded into a full bath for a master suite option. Second floor has two large bedrooms, great closet space and a full bath. Conveniently located just 7 miles from downtown Boston, minutes from the commuter rail and Winchester center.

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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907 Main Street Winchester MA 01890
Contingent

MLS Number 72916512

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,728
  • Complex Waterfield Commons

ACCEPTED OFFER. This luxury townhouse at Waterfield Commons has everything you've been looking for in Winchester! This pristine condo has the feeling of a single-family home. The main living area is open and bright, with a gas fireplace in the living room, and kitchen stainless appliances and plentiful storage. Enjoy your morning coffee on the private deck off the living room. The primary bedroom offers a walk-in closet with custom built-in storage, and en suite bath with jacuzzi tub. Second bedroom is also spacious, and has its own custom built-in storage. Laundry and full bath round out the second floor. The versatile third floor offers space for a bedroom, office, playroom, or movie room. Attached single car garage, mudroom and bonus room in ground level. Beacon Hill-style backyard. Move right in and enjoy all that Winchester has to offer: award-winning schools, access to the commuter rail and downtown Boston, Middlesex Fells, bike path, downtown

Listed by Pirani & Wile Group and Peter Pirani of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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11 Niles Lane Winchester MA 01890

Winchester, MA11 Niles Lane

Price$3,499,000

Est. Mortgage: $/month

Open House

MLS Number 72916261

  • Single Family Detached
  • Next Open House: Sun 12/5 1:00 pm. to 3:00 pm.
  • Bathroom 6
  • Rooms 12
  • Bedrooms 5

It's an end-of-season debut, the nicest renovation that Winchester has produced all year! If you've grown tired of cookie-cutter "new" construction, this is the home for you. PRIME location, one of the most sought-after streets in town. Quiet and beautiful with lake views plus your very own deeded parcel on the lake that provides you full water access. The interior stuns with a jaw-dropping layout & build-out, with quality well beyond the typical. You'll get giddy when you see the biggest kitchen/family room imaginable, complete with a wet bar, a second dishwasher & a beverage center. Light floods this house from every angle, it's spectacular. Entertain in the formal dining room and living room, flanked by a wall of glass leading to the patio and outside grilling area. Two primary bedroom suites offer options: one is massive with front and back balconies & lake views, plus dual walk-in closets. The other has a fabulous sitting room/study attached. Too much to mention, come see it!

Listed by Nancy S. Pallotta of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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314 HIGHLAND Avenue Winchester MA 01890

Winchester, MA314 HIGHLAND Avenue

Price$1,550,000

Est. Mortgage: $/month

MLS Number 72916495

  • Single Family Attached
  • Bedrooms 4
  • Bathroom 4
  • Rooms 11
  • Square Feet 4,372

The grand residence is located in a private setting steps from Winchester Center. Large rooms throughout with multiple primary suites, & a grand 2 story great room that is the heart of this home. Eat-in kitchen with pantry that flows seamlessly to sunroom & 2 tiered decks. The yellow antique yellow-pine bar is a show stopper! Sunny library and cozy family room round out first floor. Large yard for kids & pets with an opportunity for gardening. A lower-level home office with a separate entrance. This is definitely not your average Winchester home but it sure does check all the boxes for the buyer looking for a very special home in a premier location. This residence is a commuter's dream a short distance from I93 (2.3miles). Call this one home!

Listed by Nancy Ciampa McLaughlin of Redfin Corp.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.11% last updated on Dec 2, 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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