Winchester Real Estate

Just 15 minutes northwest of Boston is the beautiful town of Winchester, MA. When your kids are on summer vacation from Winchester's top-ranked public school system, have them spend time sailing at the Winchester Boat Club, keeping fit at the Winchester Swim and Tennis Club, or golfing at the Country Club. A quick trip on the Communter Rail's Purple Line will drop you right at the Fleet Center in central Boston, perfect for easy commuting to work or for an evening out. Don't miss out on D'Agostino's Deli, a famous local spot for subs, sandwiches, party trays, and more delicious deli wonders.

And Winchester real estate doesn't disappoint: find many new construction single-family homes, historic estates, luxurious condos, and more.

View currently listed real estate in Winchester below and contact Century 21 Advance Realty with any questions or to schedule a tour. You can also register with our site to save your favorite properties and receive notifications via email when a new listing matches your preferred criteria. 

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200 High Street Winchester MA 01890

Price$1,599,000

Est. Mortgage: $/month

Open House

MLS Number 72444043

  • Single Family
  • Next Open House: Sun 17th 11:30 am - 12:30 pm
  • Parking Spaces 8
  • Year Built 1957
  • Full Bath 3

Sophistication meets charm in this colonial dream home in the heart of Winchester. Gorgeous stonework frames the entrance, welcoming you into an entryway with soaring ceilings and dazzling chandelier. Flow easily through the first floor into a formal dining room and family room, which features oversized windows and a double-facing stone fireplace. Gourmet kitchen complete with beautiful granite countertops, stainless steel appliances and breakfast nook with gas fireplace. First floor includes bedroom with ensuite bathroom, perfect as in-law or au pair suite. Second floor master bedroom is the ultimate retreat with French doors, luxurious ensuite with soaking tub and glass shower and walk-in closet with space for large wardrobes. Additional highlights: attached 3 car garage, ample off-street parking, partially finished lower level and backyard with 2 decks, patio and storage shed. Make this dream home yours today!

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

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Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* 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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512 South Border Road Winchester MA 01890

Price$1,589,900

Est. Mortgage: $/month

MLS Number 72430943

  • Single Family
  • Parking Spaces 4
  • Year Built 2018
  • Full Bath 4
  • Bathroom 5

This beautiful new construction, three level Colonial home in Winchester is a must see, with a 60-90 day delivery! Located across the street from Middlesex Fells Reservation, this is the perfect location for everything Winchester has to offer. This home will feature gorgeous finishes including eat-in kitchen with new quartz counters, stainless steel appliances and formal dining room. The spacious rooms through-out the home include a finished basement with full size windows, and finished 3rd floor with a 5th bedroom and bonus room!

Listed by Gary J. Litchfield of Mass. Real Estate Solutions, LLC

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* 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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7 Wainwright Road Winchester MA 01890
Open House

MLS Number 72450851

  • Condo or Co-op
  • Next Open House: Sun 17th 1:30 pm - 2:30 pm
  • Half Bath 1
  • Bathroom 4
  • Year Built 1987

Imagine your morning meditation as you take in the beauty of the gardens from your main living space, enjoying a peaceful dinner on your private patio on a warm summer evening and entertaining your guests from your state of the art chef's kitchen. This home is the backdrop for the lifestyle you desire. This home features many of the amenities you would expect; an open floor plan, cathedral ceilings throughout the first floor, atrium windows, state of the art appliances and custom cabinetry in the kitchen, a first floor master en suite with gas fireplace and sitting area, gorgeous Brazilian hardwood floors, and a completely renovated lower level with a media room, office, guest suite, and bathroom with a steam shower. Close to major highways & commuter rail. Approximately 10 miles north Boston for all that the city has to offer. Buy the condo, own The Ledges experience.

Listed by Joanne Hofmann of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* 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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15 Royalston Avenue Winchester MA 01890

Price$1,550,000

Est. Mortgage: $/month

Open House

MLS Number 72430067

  • Single Family
  • Next Open House: Sun 17th 12:00 pm - 2:00 pm
  • Parking Spaces 4
  • Year Built 2003
  • Full Bath 3

This distinctive, updated colonial accents today's more casual lifestyle with a spacious, open floor plan, hardwood floors, and a kitchen you'll fall in love with - maple cabinets, granite counters, a huge island to seat 6+, & breakfast counter overlooking the fireplace living room. Immense dining room w/butler's pantry/2nd sink & dishwasher. The amenities continue with a 1/2 bath, 1st floor guest room, & office w/pocket doors to provide solitude from a busy household. The 2nd floor has 3 bedrooms, bath, huge laundry room, & a truly luxurious master suite w/large walk-in closet & cathedral ceilinged bath w/soaking tub, double sinks, make-up table, and large glass shower. The lower level has a huge mudroom off the 2 car garage, & large family room & bath. But wait, there's more - sliders from the kitchen lead out to a mahogany deck & a gorgeous built-in pool. A truly great Winchester home in which to live, to entertain, and to enjoy for many years to come! Muraco School!

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* 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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7 Gardner Place Winchester MA 01890

Price$1,450,000

Est. Mortgage: $/month

MLS Number 72418629

  • Single Family
  • Parking Spaces 2
  • Year Built 1932
  • Full Bath 3
  • Bathroom 4

The Gardner-Swan Ell House is a rarity, an intact Pre-Revolutionary structure whose tasteful updates and versatility make it timeless. Dating back to 1764 and originally connected to 89 Cambridge St as a shoe shop, architect Frank Patterson Smith moved the historic Ell to its present location in 1931. The Middlesex Canal ran along the property line and the land was the site of “Gardner Locks”. The present owners lovingly maintained and updated the original home with an addition in 1997 - an expansive family room, entry hall and eat-in kitchen. Beamed ceilings in the living and dining room, a home office with a separate entrance, fireplaces and charming butler's pantry add to its unique character. The second floor includes a master bedroom suite with fireplace plus 3 additional bedrooms and two baths. Spacious front and back yards, front patio and water gardens provide great space for outdoor play and entertaining. This welcoming home will delight and surprise you for years to come!

Listed by Anne Spry and Katie Tully of Waterfield Sotheby's International Realty

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$
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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* 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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30 AMBERWOOD Drive Winchester MA 01890

Price$1,425,000

Est. Mortgage: $/month

MLS Number 72436873

  • Single Family
  • Parking Spaces 8
  • Year Built 1979
  • Full Bath 3
  • Bathroom 4

Sprawling brick style home on The West Side of Winchester walking distance from the Vinson Owen Elementary School! A very special home offering superb curb appeal; an open airy floor plan & lush professional landscaped grounds on a half acre corner lot. A few of the best features of this 4000 sq ft home are 2 master suites; multi car attached garages; updated eat in kitchen adjacent to family room; finished lower level perfect for gym, home office or additional family room & fenced in rear yard with heated pool, stone patio, wood deck & 6 person outdoor hot tub. Amenities include 3 zone gas heat; central air; steam shower; 2 fireplaces & generous storage including outdoor shed. This is the home you will never want to leave.

Listed by Nancy Ciampa McLaughlin of Redfin Corp.

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$
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$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* 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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8-10 Winter Street Winchester MA 01890

Price$1,300,000

Est. Mortgage: $/month

Open House

MLS Number 72453632

  • Multi-Family Duplex
  • Next Open House: Sun 17th 1:00 pm - 3:00 pm
  • Year Built 1881
  • Bedrooms 6

OUTSTANDING DUPLEX IN WINCHESTER!!! Two-Family DUPLEX Style Home on EXTRA LARGE LOT with TWO driveways.THIS HOME HAS BEEN COMPLETELY RENOVATED , EVERYTHING IS BRAND NEW ! Close to Winchester's FINEST Restaurants and Shops, Commuter Rail, MBTA & Newly Renovated Winchester High School. EASY access to 93, 95 & Route 3. Each unit has three bedrooms with 2 1/2 baths. New cabinets with granite countertops, all new windows, flooring, roof, heating & electric ! Each side has private patio in the back. HUGE driveway with parking for at least 10 CARS. QUIET STREET & NEIGHBORHOOD. Close to brand new Tri-town bike path and highly sought after schools. Perfect investment for owner occupant or investor! Easy conversion to condo. Lots of privacy.

Listed by Mark Sullivan of T.A. Sullivan Agency Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* 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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16 Marshall Road Winchester MA 01890
Open House

MLS Number 72427239

  • Single Family
  • Next Open House: Sun 17th 1:30 pm - 2:30 pm
  • Parking Spaces 4
  • Year Built 1951
  • Full Bath 3

Live in one of the most sought after neighborhoods in Winchester and just minutes to Boston This Mid Century Modern home offers beautiful designer finishes inside and out, with it's lush landscaping, breathtaking deck and water feature. The open and airy living space is flooded with light all day from many skylights thru out. Fully appointed kitchen with marble breakfast bar, sub zero refrigerator and gold accents. The truly enormous master suite includes cathedral ceilings, window seat, it's own fireplace, incredible walk in closet with island, and exquisite master bath. Two additional bedrooms and full bath on main living level, French doors to office/study, a large media room and full bath on lower level is ideal for extended stay guests. Direct access from two car garage, additional storage. Easy access to Wedgemere Station or delightful downtown Winchester and all schools.

Listed by Candice Macoul and Lorelei Ritter of RE/MAX Luxury Living RE

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* 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

7 Wainwright Road Winchester MA 01890
Open House

MLS Number 72445578

  • Condo or Co-op
  • Next Open House: Sun 17th 12:00 pm - 1:30 pm
  • Half Bath 1
  • Bathroom 3
  • Year Built 1994

This is the Ledges unit you have been waiting for! Sitting at the top of the hill this light filled unit has sweeping sunset views to the west from a deck that spans the entire width of the condo. Step inside and see how the owner has meticulously maintained and decorated this home.There are many custom additions unique to this condo and this includes discreet handicap accessibility such as extra wide doors; a closet storage unit over the garage, custom lighting system; custom kitchen pantry; built in shelves and cabinets in both dining room and family room. Large basement enables easy conversion to living space, with walk out slider, large windows and plumbing set up for a bathroom.Master bedroom suite is on the first level with plentiful storage and closet space and access to the rear deck.Modern kitchen overlooks fireplace family room. The second floor has two large bedrooms and full bath in addition to storage closet and hall study. Hardwood floors throughout. Move right in!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* 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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310 Main Street Winchester MA 01890

Price$1,139,500

Est. Mortgage: $/month

MLS Number 72436394

  • Single Family
  • Parking Spaces 5
  • Year Built 1890
  • Full Bath 2
  • Bathroom 2

BUILDER/OWNER WILLING TO WORK WITH BUYER ON CUSTOM RENOVATION on this Great in-town location 3200+ sq ft colonial on a 10,000+ sq ft lot. Expansive front porch with gazebo-style roof welcomes you to this home. First floor features charming foyer with curved staircase, office/bedroom that connects to full bath, entertainment-sized living room with fireplace and French doors, formal dining room, cozy den loaded with windows, and kitchen with granite counter tops and stainless steel appliances. Second floor has 3+ bedrooms and full bath. Walk-up third floor has bedroom/office as well as ample storage space. Hardwood floors throughout most of first and second floors. Don't miss your opportunity to raise your family in this great house within walking distance to everything this great town has to offer.

Listed by Tom Doherty of Gibson Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.37% last updated on Feb 14, 2019
* 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

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.