Find a home

Sign Up Today!

Get fresh listings via email, save your favorite listings, match with similar properties, and unlock additional property info.

Create Your Account

Do not fill in this field:

Already have an account? Log in

Winchester MA Real Estate

Discover Winchester, MA real estate with the help from expert realtors at The Greene Realty Group. Look through a variety of listings, including commercial spaces, single family homes, apartment, and more.

Create a free account with us to save your favorites and to get notifications when similar properties are posted. If you already have an account, log in hereContact us today for more information and to set up a showing for any listing below. 

15&lot227 Vinson Circle Winchester MA 01890

Winchester, MA15&lot227 Vinson Circle

Price$6,500,000

Est. Mortgage: $/month

MLS Number 73134071

  • Residential
  • Bedrooms 6
  • Bathroom 7
  • Square Feet 8,805
  • High School Winchester

Visionary New Construction has begun! Quality and 1st class design define this rare legacy residence.Spectacular interpretation of a modern colonial designed by acclaimed architect & built by Master Builder.Impeccably positioned on one of the highest points in Winchester & commanding seasonal skyline vistas.Start your tour with the Grand 23' Entrance Hall.Sail under fabulous 10' ceilings throughout the main floor as they carry you past the library,dining room,into the living room, stunning kitchen & breakfast room.2nd floor provides 3 generous en suite BR's,Gallery,and the Grand Primary Suite with sensational dressing room & bathroom.Lower living/play space enhanced with magnificent family room,kitchenette,glass enclosed gym,game room,wine lounge,connecting wine cellar,and au pair suite with adjacent full bath.Close to an acre on 2 lots,home will be majestically oriented boasting a deep 85' setback from the street while providing rear entertaining grounds of magazine quality. No equal.

Listed by Anthony Marino of The Marino Group Collection

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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 TourAsk A QuestionMore Details

25 Ledgewood Road Winchester MA 01890

Winchester, MA25 Ledgewood Road

Price$5,800,000

Est. Mortgage: $/month

MLS Number 73159196

  • Residential
  • Bedrooms 7
  • Bathroom 5
  • Square Feet 4,231
  • High School Winchester

Opportunity abounds on a picturesque estate on a private road 7 miles from Boston and half mile from Winchester’s center. Custom built home on 3 heavily wooded acres and meticulously maintained by one family. This unique offering is an opportunity to create a private family compound or develop the approved 3 separate lots. A winding driveway leads to a mid-century modern masterpiece hidden from the road, offering unparalleled privacy. Floor plan is perfectly suited for entertaining as the large kitchen provides direct views into the family room with built-in bar. Generous dining room and formal living room offer views of the pastoral setting. High ceilings, a main floor study with access to one of 2 patios and en-suite bedroom on the main level. Upstairs 6 bedrooms each with dramatic views of the wooded grounds including owner’s suite with dressing room. Main house sits on over 1.6 acres with two additional lots measuring 0.5 acres each. A special property, looking for its next owner.

Listed by Karen S. Garrett, Robert Ellington and Kara Spelman of Better Homes and Gardens Real Estate - The Shanahan Group

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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 TourAsk A QuestionMore Details

8 Niles Lane Winchester MA 01890

Winchester, MA8 Niles Lane

Price$5,200,000

Est. Mortgage: $/month

MLS Number 73083677

  • Residential
  • Bedrooms 8
  • Bathroom 8
  • Square Feet 7,497
  • High School Winchester

MAJESTIC LAKEFRONT ESTATE! Situated directly on the Mystic lake w/ expansive yard & breathtaking views offering the most gorgeous and serene setting in all of Winchester. This 21+ room custom home includes 7/8 bedrooms and 7.5 baths. The 2 room primary suite features 13’ beamed ceiling w/ oversized windows, direct water views, luxurious bath w/ soaking tub & fireplace plus a private sitting room w/ custom cherry walls, second fireplace & balcony/deck. The kitchen is highlighted by a gourmet custom La Corneu Chateaux 48” double-oven range, w/ adjacent dining area & lakefront family room w/ fireplace & drop down ceiling TV. Formal dining & living room renovated w/ original details & beautiful woodwork preserved. Fully finished basement w/ media room, full gym, playroom, au-pair suite, & an exquisite “hidden” ~800 bottle wine cellar. This home also offers a top floor in-law suite and basement au-pair suite and features 5 fireplaces, radiant floors, expansive Ipe deck & dock.

Listed by Kim Covino & Co. Team and Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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 TourAsk A QuestionMore Details

23 Lawson Road Winchester MA 01890

Winchester, MA23 Lawson Road

Price$3,675,000

Est. Mortgage: $/month

MLS Number 73163652

  • Residential
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 5,757
  • High School Winchester

Step inside elegance in this 5,757 sq ft smart home nestled on spacious 14,000 sq ft lot! First floor welcomes you w/ grand entrance, a custom office on the right, and a formal dining room adorned w/ grand crown molding. Flow effortlessly into the dream kitchen, boasting custom cabinets, a Wolf range, premium Sub-Zero fridge, a generous island w/ Calcutta gold quartz, a wet bar, and walk-in pantry. The living room features coffered 14 ft ceilings and gas fireplace, creating the ideal entertainment space. Completing this level is an en suite w/ a den, a bedroom, a ¾ bath, a mudroom with ample storage, and a half bath. Upstairs, two spacious bedrooms sharing a Jack and Jill bath, full laundry room w/ sink, full bath w/ dual vanity, primary suite w/ his and her closets, a luxurious vanity, and high-tech thermostatic shower valve, fifth bedroom, and sitting/study room. Full lower level offers an Au Pair en suite, gym space, an entertainment area, and potential for a custom wine room.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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 TourAsk A QuestionMore Details

19 Socrates Way Winchester MA 01890

Winchester, MA19 Socrates Way

Price$3,299,000

Est. Mortgage: $/month

MLS Number 73156754

  • Residential
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 5,678
  • High School Winchester High

ULTIMATE DESIRABLE LOCATION - CUSTOM BUILT HOME - PRISTINE CONDITION - 7 MILES to BOSTON - HALF ACRE LOT - PERFECT FLAT LOT - RARE FIND in WINCHESTER - SPACE for YOUR EVERY DESIRE . Having 14 Rooms - 5+ Bedrooms, 4 Full Bathrooms and 2 Half Bathrooms - 3 floors of finished living space with a magnificent Grand Two-Story Foyer large enough to host your holidays and family celebrations. Lower Level has four spacious rooms - including a large Family/Recreation Room - perfect for a Nanny/In-Law Suite. Professionally landscaped yard and an oversized three-car Garage. Located a short distance to Schools - Winchester Center - Library - Restaurants -Coffee Shops, Town Taverns - Boutiques - Salons and two Commuter Rail stations to Boston. Do not miss this rare opportunity to own a true dream home and become part of the Winchester Community and all it has to offer.

Listed by Lucille Murray of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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 TourAsk A QuestionMore Details

11 Brooks Street Winchester MA 01890

Winchester, MA11 Brooks Street

Price$3,099,000

Est. Mortgage: $/month

MLS Number 73158209

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 5,208
  • High School Winchester

Embrace elegance, relish a private setting & enjoy one of Winchester's finest neighborhoods! Main level open floor plan showcases a kitchen replete w/luxury ~ Quartz counters, Laurier Max cabinetry, walk-in pantry & the culinary technology of Gagganeau appliances. An expansive LR w/gas fpl & custom built-ins flows into a sunrm surrounded by a canopy of trees & outdoor patio ~ sure to make entertaining exciting! Coffered ceiling & wainscoting details accent the DR plus large windows bring in natural light and the beauty of the outdoors. FIVE spacious bedrms w/built-in closets, incl. 1st FL suite & sumptuous 2nd FL Primary Suite w/vaulted ceilings & rear-facing deck! Family Rm in LL for movie & game nights w/half bath & walkout to outdoor space plus front yard to play hoops or catch. Crafted w/attention to modern desires, nestled in a slice of serenity w/easy access to Town Forest Trails, Commuter Rail, Bus and Winchester's beloved Town Center. Private financing may be available!

Listed by Michaela Pixie Mahtani of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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 TourAsk A QuestionMore Details

30 Wedgemere Avenue Winchester MA 01890

Winchester, MA30 Wedgemere Avenue

Price$2,975,000

Est. Mortgage: $/month

MLS Number 73120584

  • Residential
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 4,263
  • High School Winchester

This stately home is situated on the second block of prestigious Wedgemere Avenue, one of Winchesters' most desired addresses. This stunning home is situated on a meticulously maintained lot with gorgeous landscape, cozy private spaces offering an abundance of undeniable curb appeal. This home showcases a perfect blend of original woodwork & detail along w/ many recent updates todays buyers desire. The grand rooms flow beautifully w/ large open doorways, high ceilings & hardwood floors. The sun drenched kitchen w/ Viking appliances offers custom cabinetry w/dining banquette, desk & built ins, w/sliders to fabulous patio & fenced yard. Spacious primary bedroom w/2 baths, steam shower, walk in closet, plus home office. Two additional beds, with beautiful hall bath & lovely open foyer w/ window seat. Third level offers two add'l rooms, one w/en-suite bath. Oversized 2 car garage, plus a custom built plunge pool w/ the most stunning private setting, a great place to relax after a long day!

Listed by Kim Covino & Co. Team and Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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 TourAsk A QuestionMore Details

319 Main Street Winchester MA 01890

Winchester, MA319 Main Street

Price$2,899,900

Est. Mortgage: $/month

Open House

MLS Number 73112247

  • Residential
  • Next Open House: Fri 10/6 4:30 pm. to 6:00 pm.
  • Bedrooms 8
  • Bathroom 7
  • Square Feet 6,484

Introducing 319 Main Street...a remarkable colonial showcasing exquisite craftsmanship & details throughout! Situated in a prime location, this stately home offers a grand front brick porch providing a perfect spot to relax & enjoy warm summer evenings! Upon entering be greeted wi/stunning coffered ceilings & herringbone wd flrs.The white kitchen features high-end appliances & elegant marble countertops. Adjacent to the kitchen...a charming breakfast rm captivates, offering a cozy gas fireplace & windows that bathe the space in natural light. Additional 1st fl. highlights include: a beautiful dining rm, sitting rm w/fireplce & built-ins, a FR, a LR, a den & 1/2 ba. The 2nd flr offers 4 generously sized bdms & there's 3 more on the 3rd fl! Directly across the street, a carriage house awaits...nestled in nature & boasting 3 levels w/ a 1-bed apartment, potential for 7 cars! The Gorgeous backyard has 2 bluestone patios & is professionally landscaped! Walk to train & town!

Listed by Leeman & Gately and Jill Leeman of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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 TourAsk A QuestionMore Details

10 North Gateway Winchester MA 01890

MLS Number 73158946

  • Residential
  • Bedrooms 5
  • Bathroom 6
  • Square Feet 6,067
  • High School Winchester

Welcome to the market 10 North Gateway, a stunning new construction property in a neighborhood that everyone in Winchester LOVES! Enter in and immediately be greeted by a gorgeous 2 story foyer with access to your formal living room. The kitchen features an oversized island and is open to the fireplaced family room. A formal dining room with slider to the patio, first floor bed/office with private full bath, pantry, and mudroom with 1/2 bath are also found on this main level. The second floor is home to 4 bedrooms including the expansive primary suite. The finished basement offers a recreation room, gym, a potential 6th bedroom, and full bath! For the outdoor enthusiast, this is where you want to live! Take advantage of the Town Forest being just outside your door for hiking, biking, bird watching, or just a simple after dinner stroll. This property is located less than 1 mile from our beautiful Town Center. Take advantage of an opportunity for a home AND location as special as this!

Listed by Vita Realty Group and Philip J. Vita of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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 TourAsk A QuestionMore Details

3 Sheffield Road Winchester MA 01890

Winchester, MA3 Sheffield Road

Price$2,800,000

Est. Mortgage: $/month

MLS Number 73164804

  • Residential
  • Bedrooms 6
  • Bathroom 4
  • Square Feet 3,755
  • High School Winchester

Amazing 1907 six bedroom three and one half bath Colonial Revival located in one of Winchesters finest neighborhoods.This home is a tribute to yesteryear with its custom detail and design, magnificent woodwork, high coffered ceilings ,beautiful hardwood floors and four fireplaces.Imagine entertaining in the lovely front to back living room or enjoying the holidays by the fire in this most attractive dining room with all its exquisite detail and craftsmanship on display.Simply relax in the library and take in its beauty. Updated kitchen has a pantry. Large main bedroom suite has fireplace and updated bath.Three additional bedrooms on second floor.Third floor has two bedrooms or they can be used as an office or family room.The home has one garage in the front and original carriage house in rear. Inviting front porch looks over unusual large lot for possible expansion. This stunning property is located in the Everett Avenue- Sheffield Rd Historic district

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

$
$
%
$/month over payments
Federal 30-year interest rate: 7.31% last updated on Sep 28, 2023
* 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 TourAsk A QuestionMore Details

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. 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. MLSPIN 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.