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. 

149-151 Cross Street Winchester MA 01890

MLS Number 72550848

  • Commercial Industrial

We are pleased to present the Solberg Concrete building for sale. Long a Winchester landmark, this single-story, two-building industrial complex is ideal for an owner/occupant. The property is partially leased and the new owner will have the option of occupying just the Solberg Concrete space (approximately 4,000 SF), or terminating existing TAW leases to occupy a more substantial portion of the premises. Alternatively, the existing spaces are rented well below market in most cases and the building would allow for long-term growth for the new owner while generating income in the interim.

Listed by Phillip K. Burgess and Stephen Nohrden of Burgess Properties, Inc.

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Federal 30-year interest rate: 3.56% last updated on Sep 12, 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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9 Grove Street Winchester MA 01890

Price$3,790,000

Est. Mortgage: $/month

MLS Number 72461829

  • Single Family
  • Garage 3
  • Parking Spaces 3
  • Year Built 1914
  • Full Bath 6

Restored to its former grandeur, and renovated to modern splendor is your new home in highly desirable Winchester, MA - just 7 miles from downtown Boston. Enjoy all the convenience of being close to the city but still far enough away to relax in the serenity of this premium suburb (bonus - Winchester is situated close by to the PRIVATE AIR TRAVEL HUB of Bedford Hanscom Field Airport). Features of the home you will appreciate include a SECOND MASTER, smartly placed across the home from the main master bedroom; GYM and SAUNA/STEAM/SPA room to keep healthy, whole and mindful; WIRED FOR SMART HOME FEATURES including audio, video, and security. A third floor for extended guests or staff features a SECOND LAUNDRY ROOM, and the finished basement hosts an 1100 BOTTLE WINE CELLAR, MEDIA ROOM, and kitchen area, that will be the space to entertain your guests for movie nights or big games. A 3+ CAR GARAGE completes this magnificent home.

Listed by Michael Carucci and James Raggi of Gibson Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 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 Cambridge Street Winchester MA 01890

Price$2,998,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72484213

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Year Built 1941
  • Full Bath 5

Live Waterfront - on Mystic Lake! This totally renovated and expanded Colonial is now a modern classic, designed for comfortable, gracious living. Open First Flr features Lg windows/glass paneled drs across back, providing abundant natural light and stunning views from Kit/Fam Rm, Liv Rm w/FP and Dining Rm. Gorgeous Cook's kitchen w/high-end appliances, Lg island, leathered granite and mahogany counter tops, and wet bar for entertaining. Handsome private, paneled office w/FP, Mud Room and half bath complete floor. Second Flr boasts 4 bedrooms, all w/meticulously finished en suite baths. Retreat-like master w/dressing closet, 2nd double wardrobe, luxurious bath w/soaker tub with lake and Boston Skyline views. All finished LL w/separate entrance incl: Media/Game Rm w/FP; flexible 5th Bdrm suite, in-law, au-pair or workout rm; full bath accessed via bdrm or hall; 2nd ldry area. Sited on prof. landscaped 29K+ sf lot w/new deck, stone patio and steps to 111 ft Lakefront. 8 miles to Boston

Listed by Ann Basmaji of Waterfield Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 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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6 Harrison Street Winchester MA 01890

Price$2,995,000

Est. Mortgage: $/month

MLS Number 72466644

  • Single Family
  • Garage 3
  • Parking Spaces 4
  • Village The Flats
  • Year Built 2019

New construction colonial will take your breath away! Entryway opens up to an open concept layout: Family room w/ gas fireplace, dining room, living room, grand kitchen, office, mudroom w/ built-ins & 1.5 baths. The kitchen features an oversized island w/ White Rhino counters, Wolf double oven w/ grill, griddle, custom hood & pot filler, 54" sub zero fridge/freezer, 2 sinks, 2 dishwashers & pantry. Sliders open up to a patio & expansive lawn. 2nd floor features the grand master suite plus 3 additional bedrooms, all w/ ensuite bathrooms & walk-in closets. Master includes dramatic vaulted ceilings, cupola, attached sitting room, oversized celebrity style closet & master bathroom w/ soaking tub, rain shower & marble floors. The 3rd floor has 2 bedrooms & 1 full bathroom. Finished lower level w/ sunken media room, cable/internet setup, central vac & sitting room w/ full bathroom. Additional features: oversized laundry room; heated floors in full bathrooms; heated oversized 3-car garage.

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: 3.56% last updated on Sep 12, 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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65 Myopia Road Winchester MA 01890

Price$2,699,000

Est. Mortgage: $/month

MLS Number 72506620

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Year Built 1952
  • Full Bath 4

IMMACULATE ESTATE WITH STUNNING GROUNDS & HEATED POOL!!! This prestigious Myopia Hill address is an incredible Colonial set on an acre of land, affording privacy & tranquility. The home features a grand foyer, elegant dining room with fireplace, a chef's kitchen, and a vaulted breakfast nook; perfect for all your entertaining needs. The adjoining living & family room boasts soaring ceilings, natural light streaming through oversized windows & an impressive stone fireplace. The 2nd level features 4 spacious bedrooms, including the grand master suite with elegant master bath & dream walk-in closet. 2nd floor mezzanine game room, 3rd floor open office loft, home gym area,

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

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 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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5 Wagon Wheel Road Winchester MA 01890

Price$2,680,000

Est. Mortgage: $/month

Open House

MLS Number 72542662

  • Single Family
  • Next Open House: Sun 22nd 12:00 pm - 1:00 pm
  • Garage 3
  • Parking Spaces 12
  • Year Built 2015

This massive home sits on an acre of land of one of Winchester neighborhoods. Recently built (2015) and meticulously maintained, it is turn-key at a very high standard. It includes 7,097 square feet of living space, a huge heated pool, year-round 10 person spa, and professionally landscaping. Extreme privacy like no other. Fourteen rooms, 5 bedrooms, 6 full baths, finished basement, and a 3-car heated garage are the core of this estate. The patio has an extensive yard and room for a tennis court. A wrought-iron elegant entrance door will welcome you featuring a family room with a fireplace, formal living room, dining room, office, and the gorgeous kitchen in the first floor. The private master bedroom area dominates the second floor with a fireplace, heated tile bathroom, a large walk-in closet, and a reading room. Three large bedrooms complete the second floor including walk-in closets for each of them. The third floor offers a great living area for visitors and an addl master suite

Listed by Lisa Berry of Lisa Berry Properties

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 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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29 McCall Road Winchester MA 01890

Price$2,475,000

Est. Mortgage: $/month

MLS Number 72526503

  • Single Family
  • Garage 3
  • Parking Spaces 3
  • Village Myopia Hill
  • Year Built 1994

Custom built Myopia Hill Colonial was part of the Schrafft Estate peacock garden. From the moment you traverse the driveway nestled in greenery, this exceptional setting will capture your heart. The magical lot with beautiful mature plantings offers privacy with front porch, patios & lawn space. The spacious kitchen provides ample room for cooking & gathering with dining area & center island which flows into the 2 story, beamed ceiling family room with fireplace, interior balcony & oversized windows on three sides to enjoy all seasons. The elegant foyer opens to fireplace living room & vaulted ceiling dining room - both with access to serene patios for gracious entertaining. Enjoy a treetop view from the 2nd floor which includes a private master suite bedroom, guest room with ensuite bath, 2 additional bedrooms with shared bath & game room. Direct entry from the 3-car garage with access to both the basement & large mudroom, half bath & laundry, offers ease of living. Truly a retreat!

Listed by Anne Spry and Stephanie Mcgowan of Waterfield Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 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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60 Wedgemere Avenue Winchester MA 01890

Price$2,299,000

Est. Mortgage: $/month

MLS Number 72561930

  • Single Family
  • Garage 2
  • Parking Spaces 8
  • Year Built 1929
  • Full Bath 5

INCREDIBLE, VINTAGE, HISTORIC, TUDOR LOOKING FOR A FAMILY TO MAKE NEW MEMORIES!!! Are you looking for a home which is both modern & loaded with historic charm & character? Look no further, welcome to 60 Wedgemere Avenue. Located in the exclusive "Flats Of Winchester", this meticulously maintained home has it all! Boasting a Chef's kitchen with a top of the line SS appliance package, huge granite island & French doors to a private stone patio, perfect for a firepit during those impending cooler evenings. The oversized, fireplaced family room has plentiful custom built-ins, magnificent woodwork & is flooded with natural light. This spacious 6 bedroom, 5.5 bathroom house underwent a major renovation & addition in 2006. Private & quiet neighborhood, a short drive to Winchester center, where you'll find an abundance of coffee shops, boutiques, salons, restaurants & the commuter rail to Boston. Within the Vinson Owen school district, easy access to major highways & 7 miles North of Boston.

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 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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12 Prospect Street Winchester MA 01890

Price$2,299,000

Est. Mortgage: $/month

MLS Number 72493394

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Village near center
  • Year Built 1880

Breathtaking & completely renovated signature property with gorgeous kitchen featuring state of the art design with Thermador appliances, full wine tower, 42'' fridge, 6 burner gas range, quartzite island with seating for 4/5 and breakfast nook overlooking beautiful 27.000+ sf lot with perennial plantings and unique stone and shingle 3 car garage/ carriage house. Formal dining room with beautiful woodwork; double crown moldings, wainscoting, 2 chandeliers and bay window seating area. Elegant formal LR with lit built ins and fplc. Family room w/ oversized wood burning fplc, and a wall of windows beaming with sunlight. Enjoy summer evenings on the expansive front porch or on the rear terrace/ & patio with 6 person Jacuzzi offering gorgeous sunset views over Winchester center! This Magnificent home features 7 spacious bedrooms each w/ generous closet space & high ceilings. Basement media room, Pella windows, 400amp electric, 3 zone A/C, irrigation well, 3 car garage/carriage house ~

Listed by Kim Covino of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 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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5 Fox Hunt Lane Winchester MA 01890

Price$2,275,000

Est. Mortgage: $/month

MLS Number 72506669

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 1982
  • Full Bath 4

Understated and unique luxury. This traditional brick colonial opens into an interior of simple, contemporary beauty. Situated on 1.2 acres that border the 13th fairway of the Winchester Country Club, the home's 300-foot elevation affords sweeping views across the Mystic Lake and into East Boston, with brilliant sunrises that change hourly with the light and weather. A large deck and patio invite outside entertaining. Inside, the home mixes traditional and contemporary elements: an expansive living room with custom Butternut woodwork and vaulted ceiling; a kitchen/family room with a gas fireplace; a TV and billiards room; a master bedroom suite with a fireplace and attached office/dressing room. The second floor features two ensuite bedrooms, plus options for additional bedrooms. The walk-out lower level includes an indoor pool, greenhouse, and a fourth bedroom with a separate entrance, bathroom, and sauna.

Listed by Cynthia Houle of Berkshire Hathaway HomeServices Commonwealth Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Sep 12, 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.