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Homes for Sale Winchester MA

Browse current homes for sale in Winchester MA. Contact Barrett Sotheby's International Realty or call our Winchester office directly at 781-729-7900 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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17 Cross Street Winchester MA 01890

Winchester, MA17 Cross Street

Price$975,000

Est. Mortgage: $/month

Open House

MLS Number 73076833

  • Residential
  • Next Open House: Wed 02/8 11:30 am. to 12:30 pm.
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,070

Meticulously maintained home in prime location of Winchester. Open front porch welcomes you. Enter the foyer and embrace the huge living rm w/bay window drenching natural sunlight. Living rm leads to dining rm with sliding glass doors to 3-season room. XL eat-in kitchen is perfect for the chefs to gather. Cozy family rm or office w/bay window. Large 1st floor bedroom w/double closets. Renovated 1/2 bath complete this level. Second flr has 3 sizeable bedrms w/ample deep closets. Remodeled full bath w/radiant heated floors and attractive tile work.Two lovely stained-glass windows. LL has 336 sq. ft. bonus room perfect for teen-hangout/gym/office/family rm, plus ample storage. 3-season rm extends entertainment, provides the perfect retreat and overlooks the private fenced in level yard. Gleaming hardwood flrs throughout. Newer roof, windows, oil tank. Garage. Generous space and easy flow throughout. Quick walk to top-rated schools, park, town center. Minutes to Rte 93 & 95, train & Boston

Listed by Marina Tramontozzi of True North Realty

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$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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 Francis Circuit Winchester MA 01890

Winchester, MA11 Francis Circuit

Price$1,700,000

Est. Mortgage: $/month

Open House

MLS Number 73075349

  • Residential
  • Next Open House: Fri 02/10 11:30 am. to 1:30 pm.
  • Bedrooms 5
  • Bathroom 3
  • Square Feet 3,403

Located in the heart of Winchester- minutes to the town center, train and acclaimed schools, this incredible property sits on a quiet circle, has been renovated to a higher standard and meticulously maintained. This is a must see! Nestled in an idyllic setting, the mahogany porch is perfect for sunsets. Inside, the grandeur of the stairway, 8.5ft ceilings, and gleaming heart pine floors do impress! The kitchen is a masterpiece. The solid cherry custom cabinetry, marble-topped island, paneled Subzero/Wolf appliances and custom hood/hardware perfectly accessorize this quality, gourmet kitchen. Large dining room and living room, an eat in kitchen, half bath/laundry complete this level. There are 5 bedrooms: one is currently used as a media room. The large Primary with bath is incredible: vaulted ceiling, dressing room, built-ins and closets. The back deck, lawn, plantings and trellis create an oasis. With a finished basement, AC and top location, this is the home you've been waiting for!

Listed by Lynne Russo of Better Homes and Gardens Real Estate - The Shanahan Group

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$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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19 Everett Avenue Winchester MA 01890

Winchester, MA19 Everett Avenue

Price$1,150,000

Est. Mortgage: $/month

MLS Number 73075700

  • Residential
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 4,569
  • High School Whs

Get ready to make your mark on one of the most desirable streets in Winchester! This Alfred Elliot home is located in the Everett/Sheffield Road Historic District and offers an abundance of opportunity with 12 spacious rooms including six bedrooms, three and one half bathrooms, living room, family room, bonus room, home office, refinished hardwood floors, 3 fireplaces, and open concept kitchen/dining area. Bathrooms have all been partially renovated and the home has been converted from oil to gas. With close vicinity to schools, Mystic Lakes, Boat Club and Country Club this property stands out in a class of its own. Don't miss out on this rare opportunity - make this home yours today and be proud of the address for years to come!

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: 6.09% last updated on Feb 2, 2023
* 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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21 Holton Street Winchester MA 01890

Winchester, MA21 Holton Street

Price$825,000

Est. Mortgage: $/month

Open House

MLS Number 73075485

  • Residential
  • Next Open House: Sun 02/12 12:00 pm. to 1:30 pm.
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 1,726

Opportunity knocks! Charming colonial on a wonderful quarter-acre level lot that awaits your creative renovation ideas and expansion plans. This bright and sunny home offers a spacious fireplaced living room with beamed ceiling that leads to a heated sun room with ample windows. The connected dining room and kitchen allow for easy entertaining. The 2nd floor consists of 3 bedrooms and a full bath. New Roof in 2021, hot water tank in 2020, and hardwood floors throughout. Contractors and builders will recognize the potential of a new construction on this generous, level, corner lot. This is a great entry point to the sought-after town of Winchester offering award-winning schools, Middlesex Fells, bike path, and the lovely Town Center with shops, restaurants and amenities. Easy access to Boston via public transportation (2 commuter train stations and buses) and convenient access to highways. You don't want to miss this one!

Listed by Seeme Moreira of Coldwell Banker Realty - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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14 Seneca Road Winchester MA 01890

Winchester, MA14 Seneca Road

Price$2,399,000

Est. Mortgage: $/month

MLS Number 73075010

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5,100
  • High School Whs

Gorgeous custom built 4-5 bed 4.5 bath oversized colonial located on Winchesters' West side in desirable Ambrose school district! A stunning foyer welcomes you into this meticulously maintained home w/ woodwork and detail rarely seen. The spacious kitchen, dining & family room boast high ceilings & an open floor plan, great for entertaining w/ access to the level yard & patio. The 2nd floor features a gorgeous primary suite w/ sitting room, gas fireplace, 2 custom built closets & en suite bath w/ soaking tub & double vanity. The 2nd floor includes 3 additional bedrooms/ 2 bathrooms & laundry room. Fully finished basement w/ large media room perfect for movie/game nights & more. The bonus room in the basement can be used as a home gym/or 5th bed w/ full bathroom. Great mudroom directly off the attached 2 car garage & utility room. This home has a complete air purifying system throughout. You will fall in love with this property and all it has to offer.. don't miss this amazing home!

Listed by Kim Covino & Co. Team and Kim Covino of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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40 Elmwood Avenue Winchester MA 01890

MLS Number 73073522

  • Condo
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,662
  • High School Winchester High

The CROWN JEWEL of the building! This truly special unit is flooded with light and boasts (2) private decks, (2) master suite options, and (2) garage parking spaces. Allegro is conveniently located in DOWNTOWN WINCHESTER. Picture yourself strolling down for your morning cup of joe, then over for a quick visit to the farmers market to pick up some fresh items for dinner. Don't feel like cooking? We don't blame you! Out the door you go, AGAIN, to enjoy any one of the fabulous restaurants our town center has to offer. This is how you live when you live Allegro. This elegant Penthouse unit boasts in-unit laundry and easy one level living. Don’t forget about the elevator and heated garage for your car. Condo fee includes trash service, landscaping, snow removal, property maintenance, PLUS HEAT & WATER!

Listed by Vita Realty Group, Robert Cipro and Philip J. Vita of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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111 Cambridge Street Winchester MA 01890

Winchester, MA111 Cambridge Street

Price$1,700,000

Est. Mortgage: $/month

MLS Number 73071135

  • Residential
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 3,436
  • High School Whs

Gorgeous six-bedroom home has been lovingly renovated throughout. This house beautifully blends modern living with old world charm combining a new kitchen and baths with quality millwork, soaring ceilings, French doors and a stunning staircase of old. Step through the grand entry hall to an open dining/kitchen with Bosch appliances, a quartz-top island, coffered ceiling, custom cabinetry, new flooring, lighting, windows and hardware throughout. Enjoy entertaining in the front to back oversized living room with fireplace. Pass the elegant arched window to the second level with 4 bedrooms including the Primary en suite. With oversized bedrooms, a second full bath and excessive storage, there is plenty of space for all! The top floor offers two bedrooms, more storage and a bonus room. This home has a new electrical system, roof, fence, landscaping and has been repainted inside and out. Located minutes from Ambrose, the train and Winchester Center, don’t miss this rare move in ready home.

Listed by Lynne Russo of Better Homes and Gardens Real Estate - The Shanahan Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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 Dix Street Winchester MA 01890

Winchester, MA4 Dix Street

Price$3,200,000

Est. Mortgage: $/month

MLS Number 73070754

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5,500
  • High School Whs

Gracious old-world stucco Colonial. A rare combination of classic architecture completely renovated for modern living. Carefully curated interior design w/ all the upgrades. Chef’s kitchen w/ custom cabinetry, Wolf appliances, 10ft marble island, Wolf range, Sub-Zero, wine fridge, wet-bar & walk-in pantry. Gorgeous fire placed dining room. Sun-filled family room off kitchen w/French doors to outdoor bluestone patio & fenced yard. Living room w/ beamed ceilings, built-in window bench & fireplace. 1st floor offers additional living space w/ cozy sitting room & more built-ins. Grand foyer, mudroom w/ heated flrs. 5 Beds w/ 5 baths for flexible living space w/ dedicated office space & ample storage. Huge bonus rm w/ cork floors & built-ins perfect for playroom/studio. Home is professionally organized w/ storage & built-out closets. Anderson windows, high-efficiency systems, architectural roof, sound system, headed driveway. Steps to Winchester Center, train, schools, restaurants and more.

Listed by Leigh Ventura of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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40 Elmwood Avenue Winchester MA 01890

MLS Number 73068446

  • Condo
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,296
  • High School Winchester High

The new year is all about starting fresh; pursuing things you may not have achieved during the year before. Perhaps you missed out on an opportunity to live in Winchester’s newest development right in our town center. You’re in luck, HERE’S ANOTHER CHANCE! Welcome to unit #4 at Allegro. This is the first time this front facing unit is available for sale! Boasting in-unit laundry and easy one level living. Don’t forget about the elevator and heated garage for your car. Condo fee includes trash service, landscaping, snow removal, property maintenance, PLUS HEAT & WATER! This location is truly not to be missed. Everything is just outside your door including shops, restaurants, banks, grocery store, hardware store, and the commuter rail station. Book your visit today and see what is means to live Allegro!

Listed by Vita Realty Group, Michael Askjaer and Philip J. Vita of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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6 Glenwood Avenue Winchester MA 01890

MLS Number 73066852

  • Condo
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,285

High Quality New Construction in convenient location easy access to everything. Home features open concept Kitchen, dining area and living room perfect for entertaining. Hardwood flooring throughout bedrooms and bonus rooms. Hardy Plank maintenance free exterior. Slider off to small deck to backyard. Treks siding on front porch and back deck. All quality SS appliances, white cabinets, center island, fireplace in LR. Second floor features Master Bed and Bath, two other bedrooms with one additional full bath. Finished Bonus family room/office on 3rd Floor. Basement has high ceilings and walk out. Plenty of parking.

Listed by Claire Moore-Rosa of Burns & Egan Realty Group,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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6 Glenwood Avenue Winchester MA 01890

MLS Number 73066850

  • Condo
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,225

High Quality New Construction in convenient location easy access to everything. Home features open concept Kitchen, dining area and living room perfect for entertaining. Hardwood flooring throughout bedrooms and bonus rooms. Slider off to small deck to backyard. Treks siding on front porch and back deck. Hardy Plank Maintenance free exterior. All quality SS appliances, white cabinets, center island, fireplace in LR. Second floor features Master Bed and Bath, two other bedrooms with one additional full bath. Finished Bonus family room/office on 3rd Floor. Basement has high ceilings and walk out. Plenty of parking.

Listed by Claire Moore-Rosa of Burns & Egan Realty Group,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* 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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132 Cambridge Street Winchester MA 01890

Winchester, MA132 Cambridge Street

Price$950,000

Est. Mortgage: $/month

MLS Number 73066517

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,636

Welcome to this move in ready Craftsman Colonial Style Home. Walk into an open Living room and Dining room with gleaming hardwood floors. The Kitchen is open and has plenty of cabinet space with access to the fenced in large shaded back yard in the warmer months with beautiful patio to enjoy. There are three bedrooms and three bathrooms plenty of storage in the Attic as well. and a partially finished basement downstairs. Don’t miss this opportunity on a beautiful majestic home close to highway, train station and shopping centers and town center.

Listed by Anas Mtet of Premier Property Solutions,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.09% last updated on Feb 2, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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