Winchester MA Real Estate

View the latest real estate listings in Winchester MA below. Give us a call at 781-645-0505 or contact us online for more information or to schedule a private tour.

9 Grove Street Winchester MA 01890

Price$4,299,000

Est. Mortgage: $/month

Open House

MLS Number 72461829

  • Single Family
  • Next Open House: Sat 23rd 1:30 pm - 3:00 pm
  • Rooms 13
  • Bedrooms 8
  • Bathroom 8

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: 4.31% last updated on Mar 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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32 Everett Avenue Winchester MA 01890

Price$3,949,000

Est. Mortgage: $/month

MLS Number 72467279

  • Single Family
  • Rooms 12
  • Bedrooms 7
  • Bathroom 6
  • Year Built 1906

Every morning you could wake up to a rising sun over a quiet lake, nestled in privacy. This exclusive setting offers an unprecedented 304 feet of lake frontage, with a main house and detached office. This home underwent a massive renovation which restored all the original detail and woodwork to its glory. Grand scale to each room, with one lovelier than the next. Huge kitchen has a full dining area and connects to a family/homework room. The formal living and dining rooms delight with fireplaces and stunning tiger and quarter-sawn oak detailing. There is a receiving hall and staircase that just wows, and upstairs, escape to your master suite with a fireplaced sitting room, large WIC with burled wood builtins, and a master bath done in hand-selected rare green onyx. Full nanny suite on the third, plus a delightful artists studio/7th BR. Sprawling basement level with gym, media, wine and billiards rooms. 4 car garage holds 6! Walk to town, trains. This is a very rare opportunity.

Listed by Nancy S. Pallotta of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 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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6 Harrison Street Winchester MA 01890

Price$3,295,000

Est. Mortgage: $/month

Open House

MLS Number 72466644

  • Single Family
  • Next Open House: Sun 24th 1:00 pm - 2:00 pm
  • Rooms 20
  • Bedrooms 6
  • Bathroom 8

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: 4.31% last updated on Mar 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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5 Fox Hunt Lane Winchester MA 01890

Price$2,599,000

Est. Mortgage: $/month

MLS Number 72463183

  • Single Family
  • Rooms 10
  • Bedrooms 4
  • Bathroom 5
  • Year Built 1982

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: 4.31% last updated on Mar 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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94 Church Street Winchester MA 01890

Price$2,549,000

Est. Mortgage: $/month

Open House

MLS Number 72456588

  • Single Family
  • Next Open House: Sun 24th 12:30 pm - 2:00 pm
  • Rooms 13
  • Bedrooms 6
  • Bathroom 4

This grand Queen Anne Victorian has been completely renovated, restored & expanded with the utmost attention to detail. Enter through the vestibule and into the beautiful foyer bound by restored oak paneling and wooodwork.The 1st floor boasts gourmet eat-in kitchen complete w/ high-end appliances, built-in desk area, breakfast nook,walk-in storage & butler's pantry; formal dining & living rooms with FP & mahogany woodwork, family room with custom built-ins, laundry area, half bath and oversized media/game room or 2nd FR! The 2 room master suite features a FP sitting room, make-up area, 2 walk-in closets and full bath; 2add'l beds & 1 full marble bath complete the 2nd floor.Third floor makes for an ideal in-law/au-pair w/ 2 beds, full bath, bonus room and ample storage. LL direct entry from 2 car garage to mudroom, gym, workshop and unfinished space perfect for home theater/wine cellar.Beautifully landscaped front/rear yards feat. firepit, bluestone patio/walkway & add'l detached garage

Listed by Kim Covino of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 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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31 Swan Road Winchester MA 01890

Price$1,999,000

Est. Mortgage: $/month

MLS Number 72410499

  • Single Family
  • Rooms 12
  • Bedrooms 4
  • Bathroom 5
  • Year Built 1929

What does it mean to have a Swan Road address? It means you've arrived! Give yourself the gift of owning 31 Swan Road. A stately Tudor style home with magnificent grounds, situated on one of the finest roads that Winchester has to offer. The stunning brick exterior, adorned with slate roof, will impress you from moment one. As you enter, the beautiful foyer will leave you breathless. The sunken living room with Bath Stone fireplace and hand crafted wood walls is something straight out of a magazine. Enjoy the opulence and grandeur of a time gone by, seamlessly combined with a sensible layout and amenities of today such as a renovated kitchen with Wolf, Viking, and SubZero appliances. The second level is home to four bedrooms, and 3 full baths, including the master suite drenched with natural light, thanks in part to the homes South facing direction. Should you venture off these park-like grounds you'll find yourself within walking distance to both Winchester Country Club and Boat Club.

Listed by Philip J. Vita of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 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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47 Arlington Street Winchester MA 01890

Price$1,975,000

Est. Mortgage: $/month

MLS Number 72426120

  • Single Family
  • Rooms 13
  • Bedrooms 5
  • Bathroom 6
  • Year Built 2000

Gorgeous Colonial in move-in condition. Impeccable Myopia Hill location overlooking the Winchester Country Club with stunning light & serene golf course views, beautiful landscaping. Sweeping open floor plan is perfect for both relaxed daily living & luxurious entertaining. Outstanding craftsmanship include: high ceilings, large windows, oversized doors, exquisite bridal staircase. The sun-drenched front to back kitchen with large island & dining area opens to a covered porch - the perfect spot to enjoy your morning coffee overlooking the 4th hole. The two story foyer leads to the cathedral ceiling fireplace family room, fireplace living room & large dining room. The back entry provides easy access to the 1st floor guest room & fireplace study. The second floor includes the front to back master bedroom suite with three additional bedrooms, 2 baths & large laundry room. Spend your weekends enjoying the media room, exercise room & spacious play room or game room.

Listed by Anne Spry and Jane Byrne of Waterfield Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 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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6 Agawam Road Winchester MA 01890

Price$1,950,000

Est. Mortgage: $/month

Open House

MLS Number 72458378

  • Single Family
  • Next Open House: Sun 24th 12:00 pm - 2:00 pm
  • Rooms 11
  • Bedrooms 4
  • Bathroom 4

A HIDDEN TREASURE! Your private oasis with backyard bordering 350 ft. elevation summit of Mt. Pisgah conservation area, the highest point in Winchester. Amazing views of Boston! Enjoy the delightful breeze off Mystic Lake above the Winchester Country Club golf course. Perched high all by itself, this exceptional meticulously maintained three story eleven room home has totally private, beautifully landscaped grounds. Enjoy all seasons indoors and out. The family room is mahogany paneled with a fireplace & eat-in chef's kitchen. Create the ideal flow for today's lifestyle. On the second floor the master bedroom suite contains a fireplace & sitting area addition. Enjoy your daily private time without traveling to the spa hotel. Gracious and flexible floor plan allows for comfort and privacy. Turn the lower level into a media play area. Truly a rare great find, ample parking in your own, Full Loop - landscaped central island - Driveway. 8 mi to Boston, near 93 95 128 2 3.

Listed by Dorothea Feffer of Coldwell Banker Residential Brokerage - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 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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57 Lawson Road Winchester MA 01890

Price$1,949,000

Est. Mortgage: $/month

MLS Number 72463191

  • Single Family
  • Rooms 10
  • Bedrooms 4
  • Bathroom 4
  • Year Built 1956

Can you feel the excitement through your screen? Because we can! Not everyday does a property like this become available in one of the most SOUGHT AFTER neighborhoods that our idyllic Winchester has to offer. This 4 bedroom, 4 full bathroom, lovely colonial checks off all the boxes. Neighborhood, check! LINCOLN SCHOOL DISTRICT, check! Sensible layout, check! Oversized family room, check! Formal spaces for entertaining, check! Office, check! Finished basement with fireplace, check! Need we say more? Enter in to a dramatic 2 story foyer that will make you swoon from the moment you enter. Not enough? Let's not forget to tell you about the master suite with TWO full bathrooms (the key to any successful relationship) and TWO walk-in closets! The heart of the home, the kitchen, boasts top of the line appliances, a large center island, and full eat-in area. Situated just over 1/2 mile from Town it makes walking to dinner, to shops, to schools, the commuter rail, or just for coffee a breeze!

Listed by Philip J. Vita of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 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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4 Town Way Winchester MA 01890

Price$1,949,000

Est. Mortgage: $/month

Open House

MLS Number 72424070

  • Single Family
  • Next Open House: Sun 24th 12:00 pm - 1:00 pm
  • Rooms 10
  • Bedrooms 5
  • Bathroom 5

Recently completed NEW CONSTRUCTION - this exquisite 5 beds 4.5 bth colonial features open floor concept for today's family living! Thoughtfully designed with a high-end finishes & details, this homes offers an oversized 2-car garage, direct entry into mudroom, gourmet kitchen w/ island & Wolf/Subzero appliances, FR with FP & direct exterior access , formal LR & DR with crown moldings & wainscoting. Second floor features include master suite w/ walk-in closets, luxurious master bath, laundry room with custom cabinetry and sink, 4 oversized corner bedrooms flooded with light & ample closet space. Third floor with bonus room, add'l bedroom & full bath. Great rear yard w/deck & sliders from kitchen. The lower level bonus space features spacious family room w/fireplace, kitchenette/ full bath &-plenty of space for gym. This home is located in sought after East side of town, convenient to the center, Lincoln school district, and is truly a great neighborhood!

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 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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112 Highland Avenue Winchester MA 01890

Price$1,900,000

Est. Mortgage: $/month

MLS Number 72455664

  • Single Family
  • Rooms 12
  • Bedrooms 6
  • Bathroom 4
  • Year Built 1890

This home exudes opulence. The attached Porte Chochere (portico) conveniently located in middle of semi-circle drive, provides overhead coverage, car to door, very nice during inclement weather. Feel the elegance as you enter this exceptionally maintained home, which retains its historic character from the late 19th century. Built in 1890, with 12 rooms covering 4858 sq. ft. of living area, including 6 bedrooms and 3.5 baths, there's plenty of space for your antique furnishings and collections. New roof and outside paint were completed in 2017. Tasteful interior updates include Victorian period wallpaper, adding to its special appeal. Nothing more to do but enjoy! Showings begin on 2/28, M-F, 9:00 to 5:00 - Weekend showings by special appointment, for second viewings only. Basement and garage available for inspection 3/31. (Interior photos coming by 3/1)

Listed by Metrowest Homes Team and Ray Paulk of Keller Williams Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 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

6 FAIRFIELD Place Winchester MA 01890

Price$1,850,000

Est. Mortgage: $/month

MLS Number 72465453

  • Single Family
  • Rooms 12
  • Bedrooms 5
  • Bathroom 5
  • Year Built 2016

Stunning newer construction tucked away in a quiet neighborhood yet steps to town center, The Flats, schools, pond, tennis courts & train. A residence that was custom built in 2016 & offers over 4,500 sq ft of luxurious living on 4 levels; 5 large sunny bedrooms & 4 full baths. An inviting floor plan for all family members to enjoy with a blend of formal & informal spaces such as dining & living rooms; large 3rd fl playroom with full bath; exquisite oversized kitchen/family room that has direct access to paver patio & fenced in rear yard~ perfect for kids & pets; grand master suite & a finished lower level that is perfect for out or town guests or au pair suite. Amenities include hardwood floors; multi zone gas heating & cooking; attached garage; generous storage & so much more. Truly an urban oasis 7 miles from the Boston city line.

Listed by Nancy Ciampa McLaughlin of Redfin Corp.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.31% last updated on Mar 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details