Winchester MA Real Estate

The friendly suburban town of Winchester is about 8 miles north of Boston and offers two MBTA Commuter Rail stops and access to Interstate 93. The area is home to a beautiful downtown, outdoor recreational areas, a variety of restaurants, and a great school system that includes Winchester High School, one of Boston’s elite public schools. Explore a variety of listings currently on the market in Winchester, MA. Learn more about the town of Winchester!

Homes for Sale Winchester MA

Questions? Contact Better Homes and Gardens The Shanahan Group at 781-729-9030 or online!

Search By Property Type

Single Family Homes | Condos | Multi-Family Homes
Adult Communities | New Construction

r=26-50
36 Elmwood Avenue Winchester MA 01890
Open House

MLS Number 72672238

  • Condo or Co-op
  • Next Open House: Sun 07/12 12:00 pm. to 2:00 pm.
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,580

Introducing Residence 10 at allegro! This is The Penthouse and largest unit at allegro. This unique, one of a kind, floor plan is the entire back of the building and offers 2 master suites, half bath, 2 car parking and 2 decks overlooking picturesque Vine St. It is a beautiful, open concept layout with bedrooms flocking on either side of the living room. allegro Winchester is a boutique style building consisting of 11 unique homes in an intimate setting off the beaten path yet steps from market shopping & the MBTA Winchester Commuter Rail Station. All residences are one level with designer kitchen; well appointed master suite; multi zone gas heating & cooling; elevator access to garage parking & additional storage room. Your dream home at allegro will be ready for you by end summer 2020. NEW CONSTRUCTION IN TOWN CENTER!

Listed by Nancy Ciampa McLaughlin of Advisors Living - Back Bay

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

16 Gershon Way Winchester MA 01890

Winchester, MA16 Gershon Way, Unit 16

Price$1,425,000

Est. Mortgage: $/month

Open House

MLS Number 72670156

  • Condo or Co-op
  • Next Open House: Fri 07/10 11:00 am. to 2:30 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,549

WINCHESTER'S 1ST 55+ COMMUNITY! Designed by national, award-winning, architect Gary Snider. Imagine luxury finishes throughout, including 10' ceilings, hardwood floors and plenty of natural light. The open concept floor plan boasts a 1st floor master suite with oversized walk-in closets and luxurious bathroom. The kitchen is adorned with ceiling height cabinets, granite countertops and a top of the line stainless steel appliance package. The dining room has a beautiful coffered ceiling and sliders to a private, covered deck. The bonus room could be a home office, library or studio for your beloved hobbies. 1st floor also features a powder room and laundry. Upstairs you'll find 2 additional spacious bedrooms, a full bath and an open loft area. 2 Car garage.***MODEL HOME NOW OPEN SEVEN DAYS A WEEK***SEE ATTACHED SHOWING INSTRUCTIONS***

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

64 Highland Avenue Winchester MA 01890
Open House

MLS Number 72669392

  • Condo or Co-op
  • Next Open House: Sat 07/11 12:00 pm. to 1:30 pm.
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,610

This unique townhouse has its' own entrance from outside, giving a feeling of a separate house! A bedroom, a bath, laundry, extra nook for workout space or office are on the first floor along with separate kitchen and spacious living room/ dining room combination. Upstairs is the second bedroom, bath and an area for tv or office. The open floor plan as you enter with its' high ceilings says enjoy all this space! This owner has added soundproofing between neighboring condo, new ceiling, new hardwood floors throughout, new Kitchen Aid appliances and updated baths with ceramic tile flooring, vanities and toilets. This unit feels sparkling new. This complex, Waterfield Square (formerly the site of the Washington School) is located on Highland Avenue and abuts the town reservoir and Fells Reservation which offers many hiking trails. There are tennis courts and assigned parking spaces.(2) Whether you are starting out or downsizing, this special property is perfect for you !

Listed by Carolyn Vernaglia of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

238 Washington Street Winchester MA 01890

Winchester, MA238 Washington Street

Price$945,000

Est. Mortgage: $/month

Price Changed

MLS Number 72665760

  • Multi-Family 2 Family
  • Total Parking Spaces 5
  • MLS Status Price Changed
  • Bathroom 2
  • Year Built 1927

Attention Investors and owner occupants! Solid two-family home with 5 off street parking spaces in a prime Winchester location, blocks from Long Pond, the Fells, Winchester's hiking trails, Mill Pond, Winchester Center, shopping, commuter rail, and more. Each unit has hardwood floors throughout, large windows, period detail, and beautiful moldings. Both first and second-floor units offer two bedrooms, living room, formal dining room, in-unit laundry, updated full bath, and a back porch. Second floor unit offers in-unit laundry, a built-in dining room hutch, and a bonus room that would make the perfect in-home office or possible third bedroom. Well maintained and ready to occupy. This property is a wonderful chance to enter the Winchester market and earn money from one or both units. Call for private showings.

Listed by Guy Contaldi of Coldwell Banker Residential Brokerage - Arlington

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

432 South Border Road Winchester MA 01890

Winchester, MA432 South Border Road

Price$2,475,000

Est. Mortgage: $/month

MLS Number 72665236

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Total Parking Spaces 12
  • MLS Status Active

NEW CONSTRUCTION Step right into this beautifully designed custom home and make it yours. This spectacular home offers 5 bedrooms and 6.5 baths, and is situated on a large lot across from the Middlesex Fells, just minutes from downtown Boston. This beautiful home offers today's amenities with two car garage, direct entry into mudroom, high-end chef's kitchen, great room with fireplace, and office, all with luxury finishes such as coffered ceilings and hardwood floors. First floor offers guest bedroom with full bath. Second floor includes master suite with walk-in closet and master bath with soaking tub, laundry room and three additional bedrooms. Expansive finished basement with full bath, perfect for exercise space or media. Large, flat backyard offers ideal space for outdoor dining and entertaining. Enjoy all that Winchester offers, including award-winning schools, quaint Winchester Center with restaurants, shopping, Farmer's Market, and library, and two commuter rail stations.

Listed by Pirani & Wile Group and Peter Pirani of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

312 Cross Street Winchester MA 01890

Winchester, MA312 Cross Street

Price$729,000

Est. Mortgage: $/month

Open House

MLS Number 72665072

  • Single Family
  • Next Open House: Sun 07/12 12:00 pm. to 1:00 pm.
  • Parking Spaces 3
  • Total Parking Spaces 3
  • MLS Status Active

COMPLETELY RENOVATED HOME!!! Within the Lynch School district & walking distance to McDonald field. This cozy 3 bed, 1 bath home is in need of a new owner to share its life with. The 1st floor includes the living room, perfect for lounging, watching sports or snuggling up with a good read. The dining room / kitchen open concept plan is made for hosting your next dinner party & allowing you to be part of the conversation while preparing drinks for your guests. Adorned with stainless appliances, Quartz counters & a door that leads to a large, level, fenced back yard. Work from home in your quiet, private study. The 2nd Floor has a generous master bedroom with a separate sitting area & two additional bedrooms. The custom bathroom makes excellent use of the space, boasting a gorgeous walk-in shower. Nothing to do but move in & enjoy everything the town has to offer. A short drive to downtown Winchester bustling with coffee houses, boutiques & the commuter rail to Boston.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

256 Forest Street Winchester MA 01890

MLS Number 72663753

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Active

~New Construction in Winchester~ Under Construction for Summer Occupancy! This 11room, 5 bedroom home is the 2nd of 3 brand new homes by prominent local builder. Thoughtfully designed with an open yet traditional feel. The 1st floor features open concept kitchen and family room w/fireplace, formal dining room, gorgeous kitchen with quartz counters & center island, 1/2 bath & mud room. The 2nd flr features 4 bedrooms, hall way open to foyer below, a large laundry room w/sink, large master bedroom has a luxurious bath with soaking tub, separate fully tiled walk-in shower, double sink vanity and private water closet . The 3rd floor has a bonus room plus a 5th bedroom w/full bath perfect for au-pair, in-law or teen suite. This home is perfect for the family looking for convenient access to the Middlesex Fells, Rt 93 and in the popular Muraco School District. Showings ARE allowed and we are adhering to Covid-19 showing guidelines. Live open house Sat 6-27-20 12:30-2:00pm

Listed by The Synergy Group and Paul Cirignano of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

388 Cambridge Street Winchester MA 01890

Winchester, MA388 Cambridge Street

Price$724,900

Est. Mortgage: $/month

MLS Number 72660421

  • Single Family
  • Garage 1
  • Parking Spaces 3
  • Total Parking Spaces 4
  • MLS Status Active

Designed by architect John G. Danielson, this custom built Mid-Century Modern style home is sited on .4 acres and set far above the road amidst a bucolic wooded setting ideal for birdwatchers & hikers. The most stunning feature upon entry is the vast open living room and dining room with soaring ceilings boasting exposed solid mahogany beams and rafters, & a floor to ceiling fireplace surrounded by rare pecan wood paneling, & walls of windows flooding the rooms with natural light. Simply breathtaking! Other amenities include solid oak hardwood floors in formal rooms, hallway & bedrooms. Lower level has a fireplaced family room with pecan paneling, office, laundry, & heated 1 car garage. Building's exterior has redwood siding. Updated electrical. Heating cables under the driveway. This home is being sold AS-IS, but has had critical recent updates: e.g., in 2019, new roof, hot water heater, chimney cap & fireplace dampers. Vinson Owen Elementary. Make this your dream home in Winchester!

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

54-56 Salem Street Winchester MA 01890

Winchester, MA54-56 Salem Street

Price$775,000

Est. Mortgage: $/month

Open House

MLS Number 72660557

  • Single Family
  • Next Open House: Sun 07/12 12:30 pm. to 1:30 pm.
  • Garage 1
  • Parking Spaces 5
  • Total Parking Spaces 6

Wow! This gem of a home boasts soaring 9 1/2 ft ceilings on the first floor - a bright and light open floor plan, gleeming hardwood flooring, Stainless Steel Appliances, granite countertops & island on the first floor. Additionally there is the full bath, den & enclosed porch.The second floor is home to the Master Suite/Office area plus another bedroom and full bathroom. If that isn't enough - check out the third floor which has another two bedrooms, talk about space galore! Gorgeous flat outdoor space perfect for BBQ's - serene and tranquil. Close to all schools, shopping & the town Center. Come check out why Winchester is consecutively ranked one of the best places to live in Massachusetts!

Listed by Team Tom Truong, Marissa Truong and Tom Truong of eXp Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

32 Tremont Street Winchester MA 01890

Winchester, MA32 Tremont Street

Price$699,000

Est. Mortgage: $/month

MLS Number 72659467

  • Single Family
  • Parking Spaces 2
  • Total Parking Spaces 2
  • MLS Status Active
  • Year Built 1880

Antique Colonial with front porch and back deck on a quiet side street of Winchester. Home has 3 bedrooms with 1.5 baths and is situated in a friendly neighborhood walking distance to Winchester center and commuter rail. The first floor is freshly painted and features hardwood floors . The kitchen features new lighting and a center island perfect for preparing meals. The kitchen has a space set up for use as computer station or work space . A half bath is also on the first floor .You will love the charm of built in China cabinet in the the dining room . Family room completes the first floor.As you go up the stairs you will pass a stained glass window on your way to three bedrooms . One bedroom has washer /dryer which can stay or be removed.Washer /Dryer hook up in the basement as well . The bathroom is updated with new fixtures and paint . This is a great home in a great town.

Listed by Kelly Ryan of J. Mulkerin Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

237 High Street Winchester MA 01890

Winchester, MA237 High Street

Price$939,000

Est. Mortgage: $/month

Open House

MLS Number 72658956

  • Single Family
  • Next Open House: Sun 07/12 12:00 pm. to 1:00 pm.
  • Garage 1
  • Parking Spaces 6
  • Total Parking Spaces 7

Welcome to 237 High Street, a nature lover's dream tucked in a serene location surrounded by beautiful conservation land, hiking trails and pond views. Relax in the living room next to the fireplace or, on a warm day, in the enclosed 3 season sun porch surrounded by sights and sounds of nature. A beautiful family room features dramatic cathedral ceilings, skylight & cozy wood stove, plus sliders to a private deck & sprawling backyard. Contemporary kitchen with stainless steel appliances & granite counters. Formal dining room & half bath complete the 1st floor. Three generously sized bedrooms & 1 full bath on 2nd floor. Lower level features a large entertainment room with dry bar, laundry, storage & exterior access. Additional highlights include Nest thermostats, insulated attic, outdoor motion lights, recessed lighting. 1 car garage & off-street parking for 6 cars. Situated on a large lot in desirable West End neighborhood near VO Elementary.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

15 GROVE Street Winchester MA 01890

MLS Number 72658095

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Total Parking Spaces 8
  • MLS Status Active

Old world charm and satisfaction perfectly blended with all the comforts and luxuries of today's new construction. Manicured grounds invite you up onto the quintessential New England front porch. Open the front door and instantly take in the grand foyer, beautiful moldings and detailed wood work. On the first floor, you will find a classic front parlor to one side and a front to back living room both swimming in natural light. Dining room with fireplace and built-in china cabinet perfectly located off the large, brand new eat-in kitchen makes entertaining a breeze. The beautiful bright kitchen boasts an over-sized quartz island with seating, stainless steel appliances, large pantry, kitchen table for 6+ and access to the exterior patio, back entry or 2-car garage. The expansive second floor features 5 large bedrooms, plus a home office/guest room, 2 laundry rooms and master suite. Lower level offers great flex space for a home gym, teen get-away etc. Winchester at its finest.!

Listed by Bill Caci and Catherine Albiani of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

26 Forest Street Winchester MA 01890

Winchester, MA26 Forest Street

Price$699,000

Est. Mortgage: $/month

MLS Number 72657692

  • Single Family
  • Garage 1
  • Parking Spaces 5
  • Total Parking Spaces 6
  • MLS Status Active

Great location corner of Brookside Ave! Charming bungalow style home with many recent updates including completed renovated full bath, refinished hardwood floors and freshly painted interior walls. Move-in by summer and enjoy the wonderful amenities of Winchester! Charming home located on oversized corner lot and in desirable Muraco school neighborhood! Lovely front porch welcomes you into this sun-drenched home offering formal living room w/ wood burning fireplace open to dining room w/ built in hutch, updated kitchen with breakfast dining area and door to back yard. Potential to finish the basement with direct entry from garage. Enjoy the neighborhood park across the street and the tri-town bike path right around the corner! Don't miss out!

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

18 Brooks Street Winchester MA 01890

Winchester, MA18 Brooks Street

Price$2,249,000

Est. Mortgage: $/month

MLS Number 72654732

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Total Parking Spaces 8
  • MLS Status Active

Imagine a Back Bay mansion set in bucolic Winchester...this home personifies the look and feel.This is one of those homes that just stop you in your tracks, in an A++ location. It's all about the soaring ceilings, incredible moldings and trim. The original leaded glass windows that beckon from all over the house, a spectacular foyer that embraces with beauty, numerous windows seats, pocket doors and huge fireplaces. Spectacularly oversized custom French doors highlight the front of the house and open onto a stone porch that wraps around the house and creates an amazing entertaining flow. The living room is bathed in light and across the extra large entry hall is a matching parlor, currently being used as a study. The dining room can hold 30 for dinner! The kitchen is enormous with a big walk in pantry, and leads to a large family room.

Listed by Nancy S. Pallotta of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

5 Dean Road Winchester MA 01890

Winchester, MA5 Dean Road

Price$1,999,999

Est. Mortgage: $/month

Open House

MLS Number 72654608

  • Single Family
  • Next Open House: Sun 07/12 1:30 pm. to 3:00 pm.
  • Garage 3
  • Parking Spaces 3
  • Total Parking Spaces 6

Not all new construction is created equal. 5 Dean Road has been meticulously constructed with warm tones, modern highlights, and exquisite fixtures that will have you mesmerized from the moment you enter. The 1st floor is an entertainers dream. The designer kitchen is equipped with Thermador appliances, sophisticated wet bar, full eat-in, and oversized island. It's sure to make cooking fun again! The family room, with linear fireplace, boasts tall ceilings and exterior access to the lush green yard. A home office, 1st floor bed, full bath, parlor, formal living room, and dining room are all found on this level! Yes, this home IS expansive! The dramatic bridal staircase leads you to the 2nd floor. There you'll find 4 additional bedrooms including the master suite. This spa-like oasis offers a marble drenched bathroom AND his and hers closets! The lower level has a gym area, rec room, media room, bedroom, and full bath. With a 3 car garage this home truly has it all, and more!

Listed by Vita Realty Group and Philip J. Vita of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

65 Myopia Road Winchester MA 01890

Winchester, MA65 Myopia Road

Price$2,650,000

Est. Mortgage: $/month

MLS Number 72652226

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Total Parking Spaces 8
  • MLS Status Active

A stately Colonial set atop Myopia Hill in one of Boston's most desired suburbs, 65 Myopia Road is a tranquil & immaculate estate well adapted to modern family living. Beyond the grand entry foyer are graciously scaled living & entertaining rooms with oversized windows highlighting beautiful views of the private outdoors. These include the double height living/family room with impressive stone fireplace, chef's kitchen with vaulted breakfast nook, & formal dining room with elegant fireplace. The home's 4 generous bedrooms are all located on the 2nd level. The Master suite is breathtaking with spacious walk-in closet and luxurious bath. Additional features of this residence include the 2nd floor mezzanine game room, home gym, expansive outdoor mahogany deck, & heated outdoor pool. This home is only 9 miles north of Boston, accessible to the commuter rail to North Station, within ½ mile +/- of Ambrose School, & within close proximity to all the shops & restaurants of downtown Winchester.

Listed by Mark Doherty of Campion & Company Fine Homes Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

34 Everett Avenue Winchester MA 01890

Winchester, MA34 Everett Avenue

Price$2,799,999

Est. Mortgage: $/month

Open House

MLS Number 72650982

  • Single Family
  • Next Open House: Sun 07/12 1:30 pm. to 3:00 pm.
  • Garage 2
  • Parking Spaces 5
  • Total Parking Spaces 7

It's been almost 45 years since this iconic lakefront property has been available to own. For Winchester aficionados, you know the home in which we're referring to. From the moment you turn onto the highly acclaimed Everett Avenue this stately 6 bedroom, mediterranean style mansion, captures your eye and doesn't let it go until you approach. Once proudly featured as “THE” home on Everett Ave in the Boston Globe Magazine, “Top Spots to Live” addition, here is your chance to make it “YOUR” home. From the moment you enter into the foyer the water views will captivate you. 4 levels of living, including a walk-out basement with access to level green space overlooking the Mystic Lake. Boating, fishing, and fun right in your backyard! Stunning period detail can be found throughout including mahogany woodwork, coffered ceilings, and multiple fireplaces. Fall in love with this idyllic location. Walk to the Winchester Boat Club, Winchester Country Club, Winchester Center, AND the commuter rail.

Listed by Vita Realty Group and Philip J. Vita of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

92 Bacon Street Winchester MA 01890

Winchester, MA92 Bacon Street

Price$1,549,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72650066

  • Single Family
  • Garage 2
  • Parking Spaces 2
  • Total Parking Spaces 4
  • MLS Status Contingent

Motivated seller! This stately Colonial Revival has been beautifully maintained and is a charmer. Located at the corner of Bacon Street and Stratford Road, this property has ten rooms, six bedrooms and three and a half baths. Upon entering the front door, one can enjoy an enclosed porch. (partial screens in summer). The stunning center entrance hallway has a ten foot coffered ceiling with quartersawn oak. Natural light flows through the leaded glass windows in the Dining Room which has a built in china cabinet. A gas fireplace invites you into the Living Room. Through the pantry area is a spacious eat in kitchen.The inviting Den completes the first floor. The second floor has four bedrooms and two baths and the third, two bedrooms and a bath. The spacious two car garage faces Stratford Road for easy exiting. A good part of the backyard is patioed, perfect for shooting hoops and playing street hockey. There is a grassed area as well. Close to town, commuter rail, schools, and parks.

Listed by Carolyn Vernaglia of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

39 Myopia Road Winchester MA 01890

Winchester, MA39 Myopia Road

Price$2,349,000

Est. Mortgage: $/month

MLS Number 72651112

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Total Parking Spaces 12
  • MLS Status Active

If you are searching for privacy in a sought after enclave of Winchester this is the home for you. Large sunfilled 1st floor with a flexible floor plan. Enter into a gracious foyer with a dramatic curved staircase. The kitchen is open to family room with wide-planked hardwood floors. Huge 4 season sunroom w/ fireplace, Palladian windows and a series of glass french doors overlooking your private oasis & pool area. Formal living rm w/ marble fireplace. A sophisticated study w/ bay window & fireplace overlooking the back yard. Beautiful dining room perfect for entertaining large gatherings or intimate family meals. 2nd floor offers a private master bedroom suite w/ 4 additional bedrooms. Finished walk-out lower level w/ a large tiled bonus room, additional space for guest or au pair. Attached 2 car-garage. Close to Country Club, Boat Club & only 8 miles from Boston. Bring your design ideas and make this your forever home. House cannot be seen from street.

Listed by Leigh Ventura and David Hayes of Coldwell Banker Residential Brokerage - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

57 Grove Street Winchester MA 01890

Winchester, MA57 Grove Street

Price$1,259,900

Est. Mortgage: $/month

Open House

MLS Number 72635009

  • Single Family
  • Next Open House: Sun 07/12 11:00 am. to 1:00 pm.
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6

OPEN HOUSE SUNDAY 11AM - 1PM CDC Rules Apply. This beauty went under contract immediately before Covid really hit and 45 days later their financing fell thru. Now its your chance to own this Open Concept colonial in meticulous condition with an eye for detail throughout. A beautiful mixture of old charm with modern amenities. New kitchen and Family Room additions in the last 5 years. Gourmet kitchen with Viking Appliances, granite, SS, and center island with pendant lighting, Family room with separate mini split system, cathedral ceilings, over sized windows make this a treat to read, relax or entertain. Hardwood floors adorn the entire home, fireplaces in the living room and lower level family room which is perfect for extended family and includes separate laundry room and hobby room to enjoy your crafts. 3 spacious bedrooms and gorgeous master bathroom plus 2.5 additional baths throughout the home. Just in time for the new school year. Just down the street from McCall Middle.

Listed by John Demers of First Choice Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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 Hill Street Winchester MA 01890

Winchester, MA8 Hill Street

Price$799,000

Est. Mortgage: $/month

MLS Number 72634926

  • Single Family
  • Garage 1
  • Parking Spaces 4
  • Total Parking Spaces 5
  • MLS Status Active

PRIVATE SHOWINGS EASY, CALL TO SCHEDULE! This Like New single family home with Stoneham address offers the benefits of WINCHESTER SCHOOL SYSTEM! Located diagonally across from Winchester's Eugene Dr. & Keenan Dr. neighborhoods; & sitting on the TOWN LINES offering lower housing costs & real estate taxes! This beautiful home features many recent updates including brand new SS appliances, freshly painted interior, hardwood flooring on main level, new carpeting, oversized deck with direct access from kitchen, fenced-in rear yard & oversized shed ideal for storage. First floor open concept with maple/granite kitchen, w/ reverse osmosis water/ice maker filtration, gas cooking, island w/ seating & dining area; Formal dining room w/french doors, living room & half bath w/ laundry. Second level offers three spacious sunny bedrooms with two full baths and large en-suite master bedroom with walk-in closet.The lower level w/full bath with spacious media/FR and direct access to oversized garage

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

7 Conant Road Winchester MA 01890

MLS Number 72628630

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,651

Beautifully maintained 2-level 2-bedroom, 2.5-bath townhouse in the Willows. Spacious open living area features large windows and cozy fireplace. Eat-in kitchen with updated appliances. Hardwood floors throughout the unit. A giant master bedroom suite has walk-in closet and updated master bath with double vanities. The other bedroom has a walk-in closet can be used as home office. Central A/C and in-unit laundry including washer & dryer. Extra storage in the Basement, elevator in the building, and plenty of parking. Clubhouse with new exercise room and a heated pool for you to enjoy this summer. Convenient location to downtown Winchester shops, restaurants and commuter rail to Boston.

Listed by Derek Hui of Thread Real Estate, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

43 Grove Street Winchester MA 01890

Winchester, MA43 Grove Street

Price$2,199,000

Est. Mortgage: $/month

MLS Number 72629238

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Active

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 & high end 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, full bath &-plenty of space for gym. Looking to build an in-ground pool? This home has the perfect setting and yard to accommodate all your backyard needs. Don't miss this opportunity to customize some interior finishes!

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

83 Church Street Winchester MA 01890
Open House

MLS Number 72628015

  • Condo or Co-op
  • Next Open House: Sun 07/12 12:00 pm. to 1:30 pm.
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,669

  View our digital brochure Wonderful opportunity to be close to town, trains and shops and live in a beautiful sunny condo. Fabulous high ceilings and windows in large living room and dining room. Cozy siting area by the attractive fireplace is a perfect place to curl up with a book. Modern kitchen and updated baths. Master bedroom has private bath.Two additional bedrooms are on the second floor. This condo unit has a storage area and closet. Attractive views overlooking the gardens and green space that is the rear yard. This is a perfect opportunity to live in a fabulous condominium complex and be close to everything Winchester but also a quick train ride to Boston and affordable too.New driveway and walkways are being installed this summer as well as outlets in garage for electric cars

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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

57 Bacon Street Winchester MA 01890

Winchester, MA57 Bacon Street

Price$1,099,000

Est. Mortgage: $/month

MLS Number 72626892

  • Single Family
  • Garage 2
  • Parking Spaces 2
  • Total Parking Spaces 4
  • MLS Status Active

Best deal in town! Open house Sunday 6/28 12-1:30 Move right-in to this nicely updated single family home with huge fenced in back yard, close to Winchester center, Ginn field, mystic lake beach and walking trails, and Wedgemere train station direct to North Station!! This bright and sunny split entry home features a main level with updated eat-in kitchen w/ quartz countertops, formal dining room, living room with wood burning FP, Master BR with stylish new tiled bath, two additional spacious beds and add'l large renovated full hall bath. Newly refinished hardwood floors, Lower level features great family room loaded with windows, stone fireplace, updated half bathroom, direct access to 2-car attached garage and an abundance of storage space! Ambrose elementary school, new roof, central A/C...enjoy easy living in this great home & take advantage of all Winchester has to offer with this great home at an unbeatable price! Move in and enjoy !

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 2020
* 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. 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.