and narrow your search. If you have fewer than 200 results, you can save your search.

Open Houses

5 Wagon Wheel Road Winchester MA 01890

Price$2,780,000

Est. Mortgage: $/month

Open House

MLS Number 72542662

  • Single Family
  • Next Open House: Sun 25th 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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

65 Myopia Road Winchester MA 01890

Price$2,699,000

Est. Mortgage: $/month

Open House

MLS Number 72506620

  • Single Family
  • Next Open House: Sun 25th 12:00 pm - 1:00 pm
  • Garage 2
  • Parking Spaces 6
  • Year Built 1952

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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

12 Prospect Street Winchester MA 01890

Price$2,379,000

Est. Mortgage: $/month

Open House

MLS Number 72493394

  • Single Family
  • Next Open House: Sun 25th 12:00 pm - 1:30 pm
  • Garage 2
  • Parking Spaces 6
  • Village near center

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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

326 Highland Avenue Winchester MA 01890

Price$2,199,000

Est. Mortgage: $/month

Open House

MLS Number 72551945

  • Single Family
  • Next Open House: Sun 25th 1:30 pm - 2:30 pm
  • Garage 2
  • Parking Spaces 8
  • Year Built 1903

Majestic Winchester home with detail and craftsmanship unlike any other~ Situated proudly on a private, oversized lot with lovely level rear yard, patio and 2 car garage, offering some of the most gorgeous custom hand milled woodwork you've ever seen~ breathtaking bridal staircase with 30' ceilings, spectacular stained glass windows, from one room to the next, this home will impress. Formal Mahogany dining room with beamed ceilings and oversized fireplace, living and family rooms each w/ fireplaces~ 5/6 bedrooms, Master with french doors to sunroom/enclosed balcony, updated electrical, newer heating system, central a/c, Perfect opportunity to expand /renovate the kitchen with adjacent mudroom offering plenty of space to create todays dream kitchen, add french doors to patio and the space is beautifully blended. This home was valued at over 4Million dollars to recreate & can now be yours ~this is a very special home & a once in a lifetime opportunity! Please call for a private showing

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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

Lot 1 Reynolds Street Andover MA 01810

Price$2,150,000

Est. Mortgage: $/month

Open House

MLS Number 72525309

  • Single Family
  • Next Open House: Sun 25th 11:00 am - 1:00 pm
  • Garage 3
  • Parking Spaces 6
  • Year Built 2018

Exquisite new construction yesteryear farmhouse with all the traditional farmhouse charm & all the amenities of a brand new home on a beautiful 1-acre flat, all useable lot. 1st flr features wonderful open floorplan w/ rustic white oak flooring throughout. Family & living rms offer gas fireplaces w/ gorgeous reclaimed mantels, as well as built-ins in the family rm w/ access to the lovely backyard. Dining rm features 2 sets of flr-to-ceiling cabinets & quartz serving counter. Don't miss the top-of-line kitchen w/ subzero & wolf appliances, a wonderful center island, beverage center & custom walk-in pantry. The 1st flr also features a mudroom, laundry room & ½ bath, all with beautiful custom cabinetry. Head upstairs to your cathedral ceiling Master suite w/ 2 walk-in closets & double vanity en-suite bath. 2nd floor also features second en-suite bedroom, as well as 2 additional bedrooms & a full bath, plus a second laundry rm & large bonus rm above garage w/ full bath.

Listed by Lillian Montalto of Lillian Montalto Signature Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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

18 Jewett Street Rockport MA 01966

Price$2,100,000

Est. Mortgage: $/month

Open House

MLS Number 72370932

  • Single Family
  • Next Open House: Sun 25th 11:30 am - 1:00 pm
  • Garage 1
  • Parking Spaces 3
  • Year Built 1904

Welcome home to The Carnegie. Originally a public library commissioned by Andrew Carnegie and built in1904, this luxurious single family home has been renovated with everything you could desire while maintaining its historic significance. Upon entering this home, built from locally quarried granite, you will find yourself standing on the intricately woven floor under a soaring rotunda. Straight ahead, the light filled gourmet kitchen will have you planning your next dinner party. The expansive windows in the large fireplaced living room allow natural light in abundance as well as views to a beautifully landscaped veranda, ocean and the bustling downtown. This home also features 3+ bedrooms and 3 1/2 baths. The master bath has an oversized sunken tub and beautiful marble floors. There is also an underground garage, mudroom and many options for living. This is truly a one of a kind home. Just steps to the beach, ocean and the acclaimed Shalin Liu, this home offers it all!

Listed by Syndi Zaiger and Jill Fucillo of Nest Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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

379 Main Street Winchester MA 01890

Price$1,800,000

Est. Mortgage: $/month

Open House

MLS Number 72536636

  • Single Family
  • Next Open House: Sun 25th 1:00 pm - 3:00 pm
  • Garage 2
  • Parking Spaces 6
  • Year Built 1846

Have you been looking and looking for a large updated classic Winchester home with an open floor plan and close to town? Finally it's come on the market! This handsome updated home with an open sunny floor plan is only a 5-10 min walk to town center, train, and schools. The 21 x 15 kitchen flows into the 21 x 21 fireplaced skylit family room. Off the family room is a sky-lit cathedral ceiling sunroom featuring a hot tub and French doors out to the garden. The fully equipped kitchen has everything you could want: separate gas cooktop, 2 wall ovens, plus built-in microwave, 2 warming drawers and an abundance of cabinets. On the second floor there are 3 bedrooms and a laundry. The fireplaced master suite has a walk-in closet and custom bathroom with heated towel bar. With 2 more bedrooms and a full bath on the 3rd floor you have options for more family bedrooms, an office, or a nanny suite. This quintessential Winchester home awaits you.

Listed by Judith Ober of Berkshire Hathaway HomeServices N.E. Prime Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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

24 Calumet Road Winchester MA 01890

Price$1,780,000

Est. Mortgage: $/month

Open House

MLS Number 72545296

  • Single Family
  • Next Open House: Sat 24th 12:00 pm - 2:00 pm
  • Garage 1
  • Parking Spaces 4
  • Village The Flats

This well-designed Dutch Colonial Revival in the Winchester Flats, marked by modern amenities, radiates original warmth & character. Formal & informal rooms on the 1st floor are connected by a pleasing circular flow that feels open & natural. Elegant details include high ceilings, crown moldings, wainscoting, hardwood floors, built-ins & a split formal staircase. Entertaining is a pleasure w/both formal dining & living rooms leading to a large kitchen w/island, breakfast bar, & dining area w/sliders to a secluded deck & fenced backyard. A stunning living room w/fireplace is flanked on both sides by two pairs of uniquely crafted French doors leading to a lovely sun room/family room. A 1st floor home office is a perfect workspace. The 2nd floor master suite w/walk-in closet has a spa-like bath w/steam shower, soaking tub, & radiant floors - a true oasis. Custom mudroom off kitchen & garage. Gorgeous landscaping/perennial gardens. Close to Town Center, Commuter Rail & Ambrose Elementary.

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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

272 High Street Winchester MA 01890

Price$1,725,000

Est. Mortgage: $/month

Open House

MLS Number 72509896

  • Single Family
  • Next Open House: Sun 25th 12:00 pm - 1:30 pm
  • Garage 2
  • Parking Spaces 4
  • Year Built 1995

Looking for some peace and quiet? You will find it at 272 High Street! This meticulously maintained colonial was custom built for its current owners, in a magnificent setting abutting the Whipple Hill conservation area. Lots of beautiful windows allow tons of natural light and a spectacular view. Large open kitchen, with island and eating area, open to a bright family room. First floor also includes formal dining room, living room and office. Second floor offers four large bedrooms, one with en suite bathroom and including a large master suite with gorgeous built in dressers, two walk in closets and bright bathroom. Game room in finished basement with walk out to the backyard. Need even more space? The basement has additional space to finish and is framed for an additional bathroom, as well as an entire third floor level, ready to make your own. Follow the trails to Wright Locke Farm, take a hike at Whipple Hill and close proximity to VO School and Winchester Swim and Tennis Club.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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

46 Lorena Road Winchester MA 01890

Price$1,699,000

Est. Mortgage: $/month

Open House

MLS Number 72509519

  • Single Family
  • Next Open House: Sun 25th 11:00 am - 12:30 pm
  • Garage 2
  • Parking Spaces 8
  • Year Built 1957

MUST SEE INSIDE this beautiful East Side contemporary home, set on a large private lot surrounded by homes 2M+ in very desirable area near center. This 5 bedroom, 3.5 bath home is completely renovated~ Close to Winchester Center schools, shops & train to Boston! Plenty of living space on the first floor, boasting a gorgeous high end kitchen w/Sub Zero fridge, double wall oven, walk-in pantry with wine fridge, playroom/ mudroom off the kitchen, dining room w/walls of windows, living room with fplc, and a bonus great room with floor to ceiling stone fireplace that is a focal point in this remarkable home! The master suite is private & includes a gorgeous spa like bath w/ walk in shower, double vanity & soaking tub; four additional bedrooms are generously sized w great windows & deep closets. 2 add'l baths and 2nd floor laundry complete this floor.The exterior includes a screen porch, beautiful patio, 2 car garage, mature perennials and large private yard to enjoy! Lincoln Elementary

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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

5 W Chardon Road Winchester MA 01890

Price$1,699,000

Est. Mortgage: $/month

Open House

MLS Number 72520138

  • Single Family
  • Next Open House: Sat 24th 11:00 am - 12:30 pm
  • Garage 2
  • Parking Spaces 6
  • Year Built 1950

Well maintained custom colonial in desirable neighborhood. Corner lot w/mature plantings & great curb appeal. This sun-filled home boasts six bedrooms & three fireplaces, completely renovated approx. 2008. First floor offers two generous sized bedrooms w/versatility; office, au pair or in-law w/full bathroom & shower. Large eat in kitchen flows into family room w/gorgeous stone fireplace. French doors lead to dining room with double sided fireplace shared with living room. Second floor offers a grand oversized master bedroom suite w/high ceilings, large walk in closet, spacious master bathroom w/tub, separate shower & double vanity sinks. Add'l three bedrooms one en-suite, plus a jack & jill bathroom shared by other bedrooms . Walk up attic with plenty of storage or choose to finish space. Oversized two car garage with direct entry to mudroom. High velocity A/C. New boiler/manifold/pump 2018. Radiant flooring throughout entire home. 75 gal hot water tank. Close to train and town.

Listed by Sharyn Pasquale of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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

48 Cabot Street Winchester MA 01890

Price$1,600,000

Est. Mortgage: $/month

Open House

MLS Number 72488975

  • Single Family
  • Next Open House: Sun 25th 12:30 pm - 2:45 pm
  • Garage 2
  • Parking Spaces 4
  • Village Flats

Stunning 5 bedroom Colonial in Winchester's desirable Flats neighborhood, First floor features hardwood floors, high ceilings, formal dining room with chair rail, inviting living room with fireplace, adjacent sun-room with built-in cabinets & study/home office with french doors & custom book shelves. Gourmet kitchen with high-end stainless steel appliances, large island & french doors leading to a lovely deck, patio, fenced yard & 2-car garage. Large master suite with full bath, double vanity, soaking tub & tiled shower. Three additional bedrooms with ample closet space, full bath & laundry room on 2nd floor. Bonus third floor bedroom suite with full bath, cathedral ceiling & skylights. Huge lower level playroom,exercise room & half bath. Improvements include high efficiency split system heating and cooling with 9 zones, new driveway,new carpet in lowest level. Beautiful fenced in back yard. 2008 home updated.with all new tilt windows.This is a Cool home during the Hot summer months

Listed by Richard Brenner of Brenner Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.55% last updated on Aug 22, 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

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.