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Homes for Sale Winchester MA

Browse current homes for sale in Winchester MA. Contact Barrett Sotheby's International Realty with any questions or to schedule a viewing. Register on the site to save your favorite listings and to receive email notifications when similar listings come to market.

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. 

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2 Reservoir Street Winchester MA 01890

Winchester, MA2 Reservoir Street

Price$2,180,000

Est. Mortgage: $/month

Open House

MLS Number 73027354

  • Residential
  • Next Open House: Sat 08/20 12:00 pm. to 1:30 pm.
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,267

Elegant & spacious new construction in one of Winchester’s coveted neighborhoods situated steps from the Middlesex Fells Reservation, minutes from downtown Boston & within close proximity to town center, commuter rail & schools. If you like open concept living, high end design elements & incredible architectural details, then look no more, this is the home for you. The developer has carefully designed the house with everything in mind for today’s lifestyle & ease of living. The 1st floor has an open concept layout perfect for entertaining, a gourmet chef's kitchen, formal dining, living room with fireplace, mudroom & powder room. The 2nd floor offers a primary suite with a luxurious bathroom & walk-in closet with custom cabinetry. A 2nd ensuite, 2 more bedrooms, laundry room & full bath complete this level. The 3rd level has another bedroom & bonus room. The lower level is the perfect space for a gym, playroom or family room. Offers a spacious yard with landscaped grassy areas & patio.

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

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$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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83 Main Street Winchester MA 01890

Winchester, MA83 Main Street

Price$899,000

Est. Mortgage: $/month

Open House

MLS Number 73025920

  • Residential
  • Next Open House: Sat 08/20 12:00 pm. to 1:00 pm.
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,152

Charming Cape located in desirable Winchester! Incredible expansion potential w/ a back yard that abuts to a quiet cul-de-sac. This is truly a GEM! Spacious first floor layout w/ a living room featuring wood floors and a wood burning fireplace. Open to the formal dining room & just adjacent is a quaint office/mudroom just off the attached garage. Bright & sunny kitchen has ample storage & access to the exterior deck. Family room is an ideal location for your next game night! First floor bedroom & full bathroom complete this main level. Upper level features two oversized bedrooms along with large closets for storage and a full bathroom. Lower level is partially finished w/ incredible opportunity to add & increase additional living space. Just a short distance to Winchester Town Center where you can enjoy shopping, coffee shops, restaurants and so much more! Conveniently located near major routes to Boston, commuter rail and the Fells! You will not want to miss seeing this special home!

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

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$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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4 Horn Pond Brook Road Winchester MA 02420
Open House

MLS Number 73025767

  • Residential
  • Next Open House: Sat 08/20 12:00 pm. to 1:00 pm.
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,085

Winchester center Cottage-style home with easy, spacious one-level living. Two first floor Bedrooms, Full Bath, open concept Living and Dining Room with hardwood floors, Kitchen with gas range, Decora semi-custom cabinets, including a pantry with slide-out drawers, and Family Room plus a one-two car garage below. Enjoy the outdoors on this quiet dead-end street with immediate access steps from the home to the Tri-Community Greenway bike path; a few minutes to tennis, splash park, Winchester center shops and dining, excellent public schools, and the commuter rail, which is just two stops to Boston. This inviting home is ready for your finishing touches!

Listed by Maija Sawyer of William Raveis R.E. & Home Services

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$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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121 Loring Avenue Winchester MA 01890
Open House

MLS Number 73024289

  • Condo
  • Next Open House: Sun 08/21 1:30 pm. to 3:00 pm.
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,241

Fabulous new condo conversion updated and freshly painted throughout with updated kitchen with granite and stainless steel appliances and newer baths Hardwood floors and high ceilings. Inviting front porch with plenty of curb appeal and attached garage and parking. This first floor two bedroom/two bath unit features include central air, a large exclusive use front yard, generous storage in the basement, brand new laundry and all on one level for easy access. Excellent proximity to major commuting routes, downtown Winchester and the bus line. Don't miss this move-in ready unit.

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

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$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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 Swanton Street Winchester MA 01890

Winchester, MA11 Swanton Street

Price$849,000

Est. Mortgage: $/month

Open House

MLS Number 73024087

  • Residential
  • Next Open House: Sat 08/20 12:00 pm. to 2:00 pm.
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,386

11 Swanton St hits the market in style! While the home is located within a .5 mile radius of the Winchester schools, hospital, commerce, downtown, train stations and bus stop, it still retains it's privacy.This is 3 bed, 2 bath home boasts tall ceilings and ample space in the living room and dining room, and cathedral ceilings in the newly remodeled kitchen and entryway. Head upstairs and see the beautifully sunlit bedrooms and newly remodeled bathroom. In the basement you'll be greeted by 2 partially finished rooms with electric heat, leave it up to your creativity and finish the basement to add to the home (home theater and gym?). Then let's head out to the spacious backyard to enjoy fun and entertainment. With a back porch, and 1 of the garages finished to entertainment, your home will be a hit for family parties or friendly gatherings! The current owners have fully enjoyed this home and created wonderful memories, and now they welcome this home to a new owner to create more memorie

Listed by Javier Grandon of eXp Realty

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$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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22 Grove Place Winchester MA 01890
Open House

MLS Number 73023409

  • Condo
  • Next Open House: Sat 08/20 11:30 am. to 1:00 pm.
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 3,045

Don’t miss this gem! This condo is unique in that it's just one of two condos in the highly sought-after White Horse Commons that is a free-standing townhouse with an attached 2 car garage. Perfect for growing families & also for those looking to downsize to their forever home. Spacious FIRST FLOOR BEDROOM w/double closet & is adjacent to a full bath. 1st floor boasts a bright DR, & a two-sided gas fireplace for the home office & sun-filled living room. The living room features a vaulted ceiling w/ large picture window & access to a side deck. Spacious eat-in kitchen w/ garage access & sliders to an oversized private deck. 2nd floor offers a primary BR suite w/double vanity bath & walk-in closet. 3rd BR & two linen closets complete this floor. The lower level offers a large family room w/ built-ins, wet bar, bonus room & ample storage. Brand new HVAC & boiler. Conveniently located near the commuter rail, town shopping center, and schools. Move right in & enjoy!

Listed by Paula R. Sughrue of Better Homes and Gardens Real Estate - The Shanahan Group

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$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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 Nathaniel Road Winchester MA 01890

Winchester, MA32 Nathaniel Road

Price$999,900

Est. Mortgage: $/month

Open House

MLS Number 73023083

  • Residential
  • Next Open House: Sat 08/20 11:00 am. to 12:30 pm.
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,681

Don’t miss this well maintained colonial in the highly sought after Muraco School neighborhood. Traditional in appearance & located on a beautiful tree lined street, this house w/it’s easy living & top location will never go out of style or demand. You get that “right at home” feeling upon entering this bright sunlit home. A generous sized frplcd livrm leads to dining w/built in corner cabinet & opens to a large updtd kit w/bkfst rm addition. The 1st flr also features a nice sized famrm w/built in desk, perfect for working at home. This home flows like it was made for entertaining, both inside & out, & if this isn’t enough, sliders lead to a private patio overlooking a gardeners paradise, all while taking in views of a lge level yard! 2nd flr feat 3 generous szd bedrms, all w/hw flrs & an updated bath. The lower level offers a playrm w/exercise area for additional space. Located mins to parks, schools, close to center & commuter rail make this home the total package!

Listed by Eileen Doherty of Lamacchia Realty,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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18 Myrtle Street Winchester MA 01890

Winchester, MA18 Myrtle Street

Price$888,000

Est. Mortgage: $/month

Open House

MLS Number 73022825

  • Residential
  • Next Open House: Sat 08/20 12:00 pm. to 1:00 pm.
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,420

Location, location, location. You can have it all in this amazing 2-bedroom single-family alternative. Just minutes from downtown and all Winchester has to offer including parks, commuter rail, and The Fells. Less than .05 miles to the Lincoln Elementary School, McCall Middle School, and the High School. The Unit has been remodeled within the last two years and features high-end finishes, kitchen remodel, office space (or mud room alternative), new bathroom, 19 new windows, new stainless steel insulated front door, full insulation, new roof and so much more! The living room has a gorgeous wood-burning fireplace for those cozy winter evenings. The private backyard includes an exclusive patio and garden shed. Enjoy the illustrious history of living in The Conant-Stinson Condominium. Welcome Home!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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18 Myrtle Street Winchester MA 01890
Open House

MLS Number 73022823

  • Condo
  • Next Open House: Sat 08/20 12:00 pm. to 1:00 pm.
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 1,420

Location, location, location. You can have it all in this amazing 2-bedroom single-family alternative. Just minutes from downtown and all Winchester has to offer including parks, commuter rail, and The Fells. Less than .05 miles to the Lincoln Elementary School, McCall Middle School, and the High School. The Unit has been remodeled within the last two years and features high-end finishes, kitchen remodel, office space (or mud room alternative), new bathroom, 19 new windows, new stainless steel insulated front door, full insulation, new roof and so much more! The living room has a gorgeous wood-burning fireplace for those cozy winter evenings. The private backyard space includes an exclusive patio and garden shed. Enjoy the illustrious history of living in The Conant-Stinson Condominium. Welcome Home!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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4 Davey Lane Winchester MA 01890

Winchester, MA4 Davey Lane

Price$2,450,000

Est. Mortgage: $/month

Open House

MLS Number 73022155

  • Residential
  • Next Open House: Sun 08/21 1:00 pm. to 3:00 pm.
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5,402

Stunning custom built 5 bedroom, 4 1/2 bath colonial situated on a private cul-de-sac. Built by developer for personal use with nothing other than finest quality and craftsmanship, open floor plan & chefs kitchen with 48" Sub Zero refrigerator/freezer, DCS 6 burner range w/hood, Miele dishwasher & granite counters. Other features include 1st floor master bed & marble bath w/oversized jacuzzi, separate sauna, gorgeous wall of windows in living room opening to a beautiful deck, radiant heat throughout including 2 car garage, Lutron lighting system, separate au pair access, professionally landscaped yard w/bluestone patio, walk to "Fells" & Town Center.

Listed by Dave White of OwnerEntry.com

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$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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 Manomet Road Winchester MA 01890

Winchester, MA5 Manomet Road

Price$1,699,000

Est. Mortgage: $/month

Open House

MLS Number 73018758

  • Residential
  • Next Open House: Sat 08/20 11:00 am. to 12:30 pm.
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,800

Come see and prepare to be inspired! Spectacular and tasteful describe this 4 bedroom, 4 bath beauty in the Ambrose School District within a minute to the fabled Myopia Hill neighborhood. Meticulous, modern, and transitional flair with attention to detail and quality make this home a gem.Fabulous white kitchen with quality appliance package and white Carrera Quartz countertops.Maintenance free exterior, and professionally landscaped yard will dazzle your senses.Bright and open concept within the kitchen, dining and living areas with 2 bedrooms and full bath make up the main level.Upstairs encompasses the primary suite with connecting full bathroom and additional bedroom and full bath & laundry.Finished lower level with playroom, mudroom, home office, 4th full bathroom, and 2nd set of laundry hookups. Extra long heated garage and storage area complete the basement.Rarely does so much punch get put into such a nifty space.Value and quality are unmistakable in this turn key pleaser!

Listed by Anthony Marino of Marino Real Estate Group

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$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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4 Mayflower Road Winchester MA 01890

Winchester, MA4 Mayflower Road

Price$1,898,000

Est. Mortgage: $/month

Open House

MLS Number 73021613

  • Residential
  • Next Open House: Sat 08/20 11:00 am. to 12:30 pm.
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 4,209

This home comes w/ everything you desire! Entertain in style inside and out, with central AC and a beautiful in-ground pool! An elevated deck, great for parties & bbqs, overlooks the pool with its surrounding patio, deck, gardens & adjacent play area. Enjoy the private oversized yards as you float on by the lounge chairs and gazebo. This authentic colonial has a cedar shingled roof, copper gutters & downspouts and was just painted inside & out. Inside, the eat in kitchen with walk-in pantry includes a dining area that opens to the sun filled family room. Formal dining & living rooms, dedicated office + half bath complete the 1st floor. Head upstairs to the primary wing w/ dual custom closets, fireplace, jacuzzi & steam shower. In total 5 bedrooms & 2nd floor laundry round out the upper floor. Finished lower level has a full in-law suite! On 1/2 acre of professionally landscaped mature gardens w/ light scaping, enjoy complete privacy. If you’re looking for the perfect home, this is it!

Listed by Team Suzanne and Company and Suzanne Koller of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 5.13% last updated on Aug 18, 2022
* 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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