Winchester Real Estate

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Located just 8 miles north of Boston and Cambridge, and with easy access to both cities, you can see why Winchester has grown to become a popular bedroom community.  The town has not one, but two, commuter rail stations that take you into the city in under 20 minutes, and has direct access to the I-93 for a short drive into Boston and Cambridge. There are also bus routes that connect to the Red Line at Alewife, North Cambridge and the Orange Line at Wellington Station in Medford.  

The town has more to offer than just convenient transport links.  Another reason people are drawn to Winchester is the highly-regarded Winchester Public School system. Five elementary schools, one middle school and one high school cater for over 4600 students from Grades PK - 12. Winchester High School, recently renovated in 2017, consistently features in the lists of Top 20 High Schools in the state.  Vinson-Owen Elementary School has also been recently rebuilt (2013) and McCall Middle School is being expanded to accommodate the growing student population.   The schools are supported by the Winchester Foundation for Educational Excellence (WFEE), which raises funds to support staff and students. 

The picturesque town center, with the beautiful common flanked by the striking white church steeple, gives the town a quintessentially New England feel.  Boutique stores and salons sit alongside popular favorites such as Starbucks and CVS for essential purchases. There are a variety of options for dining out, including The Waterfield Kitchen (part of the Serenitee Restaurant Group), the locally owned Black Horse Tavern and Lucia’s Ristorante (sister restaurant of the North End favorite).  For groceries, there is a large Stop and Shop in the town, and a Whole Foods Market just across the line in Woburn.   Winchester also has its own hospital with full Emergency Room and many world-class facilities. 

One of the most stunning views of the town is looking across the Aberjona river towards the Winchester Public Library and the Town Hall.  People gather on the lawn behind the library to enjoy Town Day and the fireworks in June or to take part in the annual Halloween Parade, organized by the parent group Family Action Network of Winchester.  Across from the Town Hall, the En Ka Society brings the fair to town for a weekend in May, attracting the crowds since 1935 for this annual tradition.  Winchester has a thriving senior center, The Jenks, which as well as being a hub for the over-55’s, also hosts events and guest speakers for the whole community.   

A portion of the Middlesex Fells Reservation sits within Winchester’s borders, with access points along South Border Road.  This is a popular spot with families for hiking, biking and nature walks.  Upper Mystic Lake is another beauty spot within the town, and the Winchester Boat Club offers a prime spot from which to enjoy the lakes.  Wright-Locke Farm, a community farm offering organic produce, youth and adult education programs and events, is another gem of a place in town to enjoy the outdoors.

With all that Winchester has to offer, it’s no wonder property is in high demand in the town.  Speak to an experienced agent to find out more about the current real estate market in Winchester and how you can secure your dream home.

 

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1A Ledgewood Road Winchester MA 01890

Winchester, MA1A Ledgewood Road

Price$3,495,000

Est. Mortgage: $/month

MLS Number 72710089

  • Single Family
  • Rooms 12
  • Bedrooms 5
  • Full Bath 6
  • Half Bath 1

Developer saved the best for last at Winchester's new French Hill luxury home development. Exquisite details abound inside and outside in this masterpiece estate in one of Winchester's most desirable neighborhoods! Five-six Bedrooms, six and one-half Baths, include luxurious Master Suite complete with Sitting Room and two walk-in closets. Enormous Kitchen with two islands, premiere stainless and paneled gas appliances and Butler's Pantry. Over-sized bluestone Deck with perennial border overlooks lush grounds, setting the perfect scene for entertaining and relaxing. Deep 3-car Garage, outfitted Mudroom and 1st floor Office Suite. Gracious front porch, and shingled exterior, with fieldstone detail. Enjoy a scenic stroll into both Winchester's charming downtown and the “Fells,” with acres of hiking and mountain biking trails. Walk to the commuter rail, playgrounds and schools. Sited on an exquisite parcel - perfect for a swimming pool - just 11 minutes to downtown Boston!

Listed by Elizabeth P. Crampton of Coldwell Banker Residential Brokerage - Lexington

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$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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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281 Cross Street Winchester MA 01890

MLS Number 72710273

  • Rental
  • Bedrooms 3
  • Parking Spaces 2
  • Pets Yes w/ Restrictions

Rent this three bedrooms & 2 full bath in desirable Lynch School district for $2,400!. A good layout, open living room, dining room kitchen on the first floor. Upstairs, three bedrooms with an updated full bath, plus an additional family/play room with a full bath in the basement. Hardwood flooring throughout, Central AC, SS appliances in this updated kitchen. Back yard with patio for entertaining and enjoying the summer nights. Two assigned off street parking. Easy access to 93/95, commuter rail, restaurants, schools, conservation areas. Per Owner, NO SMOKE, GOOD CREDIT and REFERENCES REQUIRED.

Listed by Danny Zheng of Keller Williams Realty

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$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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 Gershon Way Winchester MA 01890

Winchester, MA19 Gershon Way, Unit 19

Price$1,550,000

Est. Mortgage: $/month

Open House

MLS Number 72709846

  • Condo or Co-op
  • Next Open House: Sat 08/15 11:30 am. to 2:30 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,638

WINCHESTER'S 1ST 55+ COMMUNITY! Designed by national, award-winning, architect Gary Snider. Imagine luxury finishes throughout, including 10' ceilings, hardwood floors and plenty of natural light. The open concept floor plan boasts a 1st floor master suite with oversized walk-in closets and luxurious bathroom. The kitchen is adorned with ceiling height cabinets, granite countertops and a top of the line stainless steel appliance package. The dining room has a beautiful coffered ceiling and sliders to a private, covered deck. The bonus room could be a home office, library or studio for your beloved hobbies. 1st floor also features a powder room and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath and an open loft area. 2 Car garage.***MODEL HOME OPEN DAILY 11-4PM***

Listed by The Marrocco Group of Coldwell Banker Residential Brokerage - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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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86 Middlesex Street Winchester MA 01890

Winchester, MA86 Middlesex Street

Price$675,000

Est. Mortgage: $/month

Open House

MLS Number 72709018

  • Single Family
  • Next Open House: Sat 08/15 1:00 pm. to 2:30 pm.
  • Rooms 6
  • Bedrooms 2
  • Full Bath 1

Home Sweet Home! 86 Middlesex St is a lovingly maintained home, featuring gorgeous oak flooring throughout and a great open floor plan. An updated kitchen with stainless appliances, granite counters and plenty of space for cooking opens to a sunny dining room, ready to fit a big table. The family room has great space for hanging out with wireless ready recess lighting and built in speakers and opens to an office area with sliders out to the yard. The second floor offers two large bedrooms and one full bathroom, updated with modern fixtures and lots of storage space. Unfinished basement provides laundry, additional storage and ample ceiling height for your home gym! Lots of smart home tech including Nest thermostats, smoke detectors and door lock. Enjoy the outdoors in a private, fenced in yard with patio, shed and plenty of space for gardening or play. Or, venture out to nearby schools, Winchester town center, Tri-Community Greenway and Horn Pond. Perfection!

Listed by Karen S. Garrett of Better Homes and Gardens Real Estate - The Shanahan Group

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$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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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185 Cross Street Winchester MA 01890

Winchester, MA185 Cross Street

Price$1,599,000

Est. Mortgage: $/month

Open House

MLS Number 72708352

  • Single Family
  • Next Open House: Sat 08/15 12:00 pm. to 1:00 pm.
  • Rooms 18
  • Bedrooms 5
  • Full Bath 4

Prepare to be stunned when you step into this impeccably designed, luxury home! This custom Colonial, newly built in 2016, boasts 4 finished levels! An open concept first floor features a chef's kitchen with island seating, custom cabinetry and high end appliances. You'll love the fireplace and built-in shelving in the sun-filled family room, as well as convenient home office and 1st fl bath. The 2nd fl offers 3 bedrooms, including a gorgeous master with shower & soaking tub and huge walk-in closet! Entertain often? Get ready to walk back in time--push the 3rd fl bookcase to reveal a hidden speakeasy with rich leather walls and bar that features a copper sink and ice fridge! There's even more: another full bed and bath in the finished basement, along with a custom wine room and kitchenette. There's an attached garage & fenced yard with beautiful patio and garden. Close to Rte. 93 and Fells reservation. You simply MUST SEE this gem of a 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: 2.96% last updated on Aug 13, 2020
* 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 Baldwin Street Winchester MA 01890

Winchester, MA22 Baldwin Street

Price$699,900

Est. Mortgage: $/month

Open House

MLS Number 72707874

  • Single Family
  • Next Open House: Sat 08/15 11:30 am. to 1:30 pm.
  • Rooms 7
  • Bedrooms 3
  • Full Bath 2

Meticulously cared for by the same family for a half century and its pride speaks loudly for itself. This sound and charming HOME sits on an extremely level 9500 sq ft lot affording its new owner a myriad of options in both indoor and outdoor future living options. Located on a small dead end provides that community feel and a limited amount of traffic. Tall mature plantings provide privacy for outdoor activities and entertaining. Inside you will find well maintained hardwood on both levels, a spotless kitchen with gas stove, a generous living room, and a dining room featuring an impressive built in cabinet. Den off of kitchen offers wood burning fireplace and full bath with its own heating zone. Second floor is where you will find three bedrooms and a full bath. Finished room in basement provides additional space. Easy access to major transportation routes and walking distance to downtown with its diverse options for shopping, dining, as well as one of Winchester's two commuter rails.

Listed by REthink39 Group and Philip Massa of LAER Realty Partners

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$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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 clark Street Winchester MA 01890

MLS Number 72707576

  • Rental
  • Bedrooms 2
  • Pets

Two bedroom with one bath all hardwood floors on one level. Short walk to the Center with shops and restaurants, the commuter train and buses to wellington and alewife stations. Separate laundry in the basement and storage . Dead end street with one parking space in front of house. Tandem driveway belongs to owner. Available if snowing . Good credit and references required. First, last and rental fee group showing begins wednesday from 4:30 to 5:30

Listed by Joan Theuer of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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 Oneida Circle Winchester MA 01890

Winchester, MA3 Oneida Circle

Price$799,900

Est. Mortgage: $/month

MLS Number 72707325

  • Single Family
  • Rooms 7
  • Bedrooms 3
  • Full Bath 1
  • Half Bath 1

Location can't be beat! This charming Colonial is situated in the coveted Ambrose Elementary School neighborhood. Plenty of natural light streams through and offers a cheery feel to this solid home. Features of this home include high ceilings, hardwood flooring, 3 large bedrooms, 1.5 bath, a one car garage and a wonderfully private backyard. First floor includes a large living room with hardwood flooring and a fireplace flanked with built-in bookshelves, dining room with corner cabinet. This much loved home is ready for its new owner to refresh and enjoy! Offers due Saturday, August 15th by 5 p.m.

Listed by Stephanie McGowan of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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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372 Cambridge Street Winchester MA 01890

Winchester, MA372 Cambridge Street

Price$749,999

Est. Mortgage: $/month

Open House

MLS Number 72706984

  • Single Family
  • Next Open House: Sat 08/15 12:00 pm. to 1:30 pm.
  • Rooms 9
  • Bedrooms 5
  • Full Bath 2

Discreetly set back from the road is this TWO OWNER hidden treasure! As you approach you will be immediately greeted by an oversized and secluded courtyard. Surrounded by lush greenery, you will truly feel like you're relaxing in your own private retreat every day. Morning coffee, or your evening dinner, will be enjoyed tenfold here! The main level of this property is where you will find the open concept living room and kitchen. A beautiful brick wood burning fireplace is the focal point of this space which also boasts an eat-in dining area. With treetop views from every window you'll feel tranquil energy from each room in 372 Cambridge Street. On the upper level you will find 3 bedrooms, and your first full bath. This bath has been beautifully renovated with current tile, frameless glass shower door, and stone countertops. As you make your way down a level you'll find 2 additional bedrooms, a play room, and another tastefully renovated full bath. Located in the desirable VO district!

Listed by Vita Realty Group and Philip J. Vita of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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 Trinity Road Winchester MA 01890

Winchester, MA11 Trinity Road

Price$1,199,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72706409

  • Single Family
  • Rooms 8
  • Bedrooms 4
  • Full Bath 2
  • Half Bath 1

Welcome to Winchester! Never before offered to the public - this spacious multi-level home offers sprawling grounds, oversized living space and the opportunity to customize and renovate to make this your own!! Located on cul-de-sac in desirable Vinsen Owen neighborhood - this 4 bed 2.5 bath home has been meticulously maintained by the same family for over 50+ years. The main level offers a cozy living room w/ FP & oversized windows, dining room and eat-in kitchen with direct access to the yard/patio. Four oversized bedrooms with a master suite equipped with walk-in closet and full bath. The lower level features 2-car attached, mudroom/laundry area, family room and half bath. Located minutes from Wright-Locke Farm, Whipple Hill, Winchester Country Club and Turkey Hill hiking trails this home is a must see!!

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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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24 Surrey Road Winchester MA 01890

Winchester, MA24 Surrey Road

Price$1,699,999

Est. Mortgage: $/month

Open House

MLS Number 72706012

  • Single Family
  • Next Open House: Sat 08/15 12:00 pm. to 1:30 pm.
  • Rooms 10
  • Bedrooms 4
  • Full Bath 3

This may seem like your typical split-level home from the exterior but my, oh, my, would you be WRONG! As you enter a dramatic foyer with stunning crystal orbital chandelier will lead you to the living room with cathedral ceilings and floor to ceiling ledger stone fireplace. To say this section of the home is impressive would be an understatement! But it gets better from there; the dining room offers majestic views of the Boston city skyline. The beautifully renovated kitchen with eat-in area boasts a stainless farmers sink and Bosch appliances including a 36" induction cooktop. Three bedrooms, including the master suite, are also found on this level. Access to the rear deck and a stunning spa-like bathroom with body sprays, linear drain, and steam shower are just a few of this masters special features. The lower level has an expansive family room, play room, bed #4, a full bath, kitchenette, and access to the 2 car garage. Quite possibly the in-law you've been searching for! Come see!

Listed by Vita Realty Group and Philip J. Vita of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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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123 Washington Street Winchester MA 01890

MLS Number 72705834

  • Commercial Office
  • Total Parking Spaces 3
  • Year Built 1930
  • MLS Status Active

LIVE/WORK in a piece of Winchester's history! Gorgeous & architecturally re-designed building by Architect Mary McKenna was transformed into 2 diverse Green-Sustainable, live/work spaces w/ special zoning granted to allow for a luxurious and super chic home/ loft space with floor to ceiling windows & flex floor plan including 2 beds 2 ½ bath home PLUS an expansive and completely separate 1290 sf office/ business space! Enjoy an easy commute to work; only one level below!! Live upstairs and work downstairs, with separate entries, each floor custom designed to maximize natural light and design potential w/beautiful hand crafted cabinets & mill work by Master Craftsman, David Sullivan. Lavish baths on each floor, full kitchen and kitchenette in LL office, elevator shaft ready to accept elevator, completely renovated inside & out with all new systems, ample electrical wiring to allow for full office capabilities & high speed internet & potential for future roof deck overlooking downtown.

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.96% last updated on Aug 13, 2020
* 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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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.

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