Winchester Homes for Sale

Colonial Home in Winchester MAWinchester MA real estate is popular for families and professionals who work in the greater Boston area. Types of homes in Winchester range from Colonials and Victorians to custom homes and newer construction properties. The community offers plenty of recreational opportunities and is located just 9 miles northwest of Boston. You may also be interested in browsing all available single-family homes for sale north of Boston.

View Winchester, MA Single-Family Homes for Sale

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

376 Cambridge Street Winchester MA 01890

Winchester, MA376 Cambridge Street

Price$1,006,893

Est. Mortgage: $/month

Open House

MLS Number 72897497

  • Single Family Detached
  • Next Open House: Sat 09/25 11:00 am. to 1:00 pm.
  • Bathroom 3
  • Rooms 6
  • Bedrooms 3

First time on the market this home is ready for its second owner! This home has been meticulously maintained and loved over the years. You will find well cared for original hardwood flooring throughout, along with original tiling to include Italian ceramic tiles. The open living room has a custom Mahogany mantel on the wood-burning fireplace and polished limestone hearth. The dining room has a large picture window for viewing the mature detailed landscaping. The eat-in kitchen leads to the rear yard & a spacious patio for outside entertaining & landscaping that must be seen to be appreciated. The lower level has a large family room complete with another wood-burning fireplace, ¾ bath, laundry room & direct access to the two-car garage. In the garage, you will find a cold storage room that has been filled with many homemade wines, sauces & more. Being centrally located to many great shopping experiences, major highways & T stations make this a commuters dream. Agent related to Sellers.

Listed by Catharine Bray and Michael Petrowski of Keller Williams Coastal Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

23 Lawson Road Winchester MA 01890

Winchester, MA23 Lawson Road

Price$1,559,000

Est. Mortgage: $/month

Open House

MLS Number 72898281

  • Single Family Detached
  • Next Open House: Sat 09/25 11:30 am. to 1:00 pm.
  • Village Near center
  • Bedrooms 3
  • Bathroom 3

Welcome to this picture perfect Cape filled with character and charm in TOP location close to the town center and schools.This sweet home home is perfect for the buyer looking to downsize or for a buyer or builder looking to expand. A beautiful sunlit foyer welcomes you & flows into a large family room with lots of windows and natural light, featuring an oversized fireplace and custom built-ins. A formal living room and dining room are joined by French doors. A lovely kitchen awaits with views of the picturesque yard & patio through the oversized windows. A full bath, mudroom and attached garage with direct access complete this floor. The second floor has a full rear dormer creating space for two generously sized bedrooms/ three rooms; the master consists of two rooms and works nicely as adj. home office space. The lower level offers a third bedroom, full bath and laundry. Plenty of storage throughout, Central A/C. This home is situated on a beautiful lot with an abundance of privacy!

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

12 Chestnut Street Winchester MA 01890

Winchester, MA12 Chestnut Street

Price$1,499,000

Est. Mortgage: $/month

Open House

MLS Number 72898196

  • Single Family Detached
  • Next Open House: Thu 09/23 12:00 pm. to 1:00 pm.
  • Bathroom 3
  • Rooms 9
  • Bedrooms 4

Welcome to Winchester! A gorgeous Colonial located on upper Chestnut Street. Walking distance to the Lincoln Elementary School and McCall Middle School. This feature-rich home with beautiful woodwork expands approximately 3,500 sq/ft and is situated on over a quarter-acre lot. Enter the foyer with original hardwood floors that flow nicely into a sitting room, family room, and formal dining room. Off the spacious eat-in kitchen, an open concept living area is complete with a projector and drop-down screen to watch football in a theater-like setting. On the second floor, you will find three spacious bedrooms and a smaller room perfect for a home office. The master features a separate room that could double as an office, nursery, or amazing walk-in closet. A finished 3rd floor provides bonus space for a playroom, home gym, or hobby room. There is more! An amazing backyard awaits for BBQs and a spacious garage and plentiful parking to boot! Do not miss this opportunity!

Listed by Nick Lento Group and David Beeching of Coldwell Banker Realty - Arlington

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

60 Emerson Road Winchester MA 01890

Winchester, MA60 Emerson Road

Price$1,600,000

Est. Mortgage: $/month

MLS Number 72896521

  • Single Family Detached
  • Village West Side
  • Bathroom 3
  • Bedrooms 4
  • Rooms 9

Welcome to this tastefully remodeled 4/5 bed home nestled into the hillside at the end of desirable Emerson Road! Enjoy the backyard oasis filled with peach and apple trees, nice lawn area and new deck perfect for outdoor entertaining. Enter the home through the welcoming foyer and fall in love with the sunny open floor plan. The spacious european designed kitchen offers an oversized island w/ seating, high end appliances with an abundance of storage & breakfast area w/ picture window. A formal dining room, sunny living room w/ historic fireplace & family room/ or 5th bed with a full bath and a laundry room complete the first level. The second floor offers 4 bedrooms w/ 2 bathrooms; a fabulous master suite w/ updated full bath and custom walk in closet, and an office/homework space w/ built in desks. Finished lower level with family room, fireplace, fun kids play area and plenty of storage. 2 car attached garage, central AC, all new windows & updated systems. Move right in and enjoy!

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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 Berkshire Drive Winchester MA 01890

Winchester, MA18 Berkshire Drive

Price$1,090,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72895354

  • Single Family Detached
  • Bathroom 3
  • Rooms 8
  • Bedrooms 4
  • Square Feet 2,626

This beautiful hardwood floored multi-level home has unlimited potential with its ample space and prime location on the West Side of Winchester. With its expansive bay window and fireplace, the living room offers a serene view of the neighborhood from the comfort of your couch or through the dining room. The dining room opens up to the enclosed porch w/ its 3 walls of windows that showcase the natural beauty of the wooded backyard. The spacious master bedroom includes an en-suite master bath and large walk-in closet. The 3 other bedrooms each feature double closets and offer plenty of opportunity. The lower level family room has direct access to the two car garage, laundry room, and basement. Offers due by 10am, Monday, 9/20.

Listed by Anne Spry of Barrett Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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 Ginn Road Winchester MA 01890

Winchester, MA34 Ginn Road

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72894624

  • Single Family Detached
  • Bathroom 5
  • Bedrooms 5
  • Rooms 15
  • Acreage 0.39

COOK THANKSGIVING DINNER IN YOUR BRAND NEW KITCHEN! New construction home with an estimated completion date of November 2021. Local master builder brings another winning design to Winchester. Showing off both vertical & horizontal siding and featuring a metal roof over the front porch. This home will be loaded with high tech bells and whistles for modern conveniences. Just shy of 6,000 square feet, there's plenty of space for the family to spread out on 4 different floors. The phenomenal master wing boasts a sitting-library-dressing room with gas fireplace, a separate bedroom with soaring ceilings, a to-die-for walk in closet and gorgeous bathroom. Start your day with a workout in your downstairs gym. Multiple locations to set up a home office. There's even a secondary master suite on the 1st floor, perfect for overnight guests. The hardscape features spectacular stone work including a fire pit for those up coming cooler evenings. 2-Car garage and ample parking.

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

8 Westland Avenue Winchester MA 01890

Winchester, MA8 Westland Avenue

Price$1,700,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72894282

  • Single Family Detached
  • Bathroom 3
  • Rooms 11
  • Bedrooms 4
  • Acreage 0.34

Sumptuously landscaped modern colonial radiates an ambiance of comfortable elegance throughout: high ceilings, gleaming hardwood floors, 3 fireplaces, & a spacious, versatile floor plan for everyday living & entertaining. The sensational living room has soaring ceilings, walls of windows, & an impressive wood burning fireplace. The large sun-splashed eat-in kitchen features custom cabinetry, peninsula seating, granite counters, ss appliances, & a vaulted ceiling w/skylight. The kitchen is open to the sunroom, & a circular flow connects all 1st floor rooms including a formal dining room, office, & half bath. 2nd floor has 4 bedrooms, 2 full baths, & features a primary bedroom w/cathedral ceilings, dramatic windows & fireplace. Lower level has a finished media/game room & playroom. Exterior amenities: a 2-tiered deck, koi pond, & treehouse. Two-car detached garage w/storage. Ambrose Elementary location; close to Winchester center w/two commuter rail stops. Welcome to your forever home!

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

19 Hancock Street Winchester MA 01890
Open House

MLS Number 72893699

  • Single Family Detached
  • Next Open House: Sun 09/26 2:00 pm. to 3:30 pm.
  • Bathroom 2
  • Bedrooms 5
  • Rooms 11

Attention investors and owner occupants! This Classic two family with craftsman details is located on quiet street in Winchester Highlands with 15,000 sf lot, could easily be converted to a single family. Walking distance to The Fells Reservation, perfect for hiking, biking, or walking your dog. Close proximity to downtown Winchester with shops, restaurants, Commuter Rail and more. First floor unit, 2 bed, 1 bath. Second floor unit, 3 bed, 1 bath. Both units feature sunny living rooms, large formal dining rooms, and hardwood floors throughout. The second floor could be converted to 4-5 bedrooms. Front covered porch and large rear deck, plus immense side yard offers potential for expansion. Includes giant driveway that can comfortably fit 6 cars, plus 2 garage spaces. ~Open House Sunday Sept 26th 2:00-3:30pm~

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

119 Forest Street Winchester MA 01890

Winchester, MA119 Forest Street

Price$2,349,000

Est. Mortgage: $/month

MLS Number 72893561

  • Single Family Detached
  • Village Fells area
  • Bathroom 6
  • Rooms 12
  • Bedrooms 5

Must see this fabulous +/- 6000 sf Colonial farmhouse! This newly constructed 5 bed, 4 full, 2 half bath home by premiere local builder is one of a kind & offers space & style that will impress! With the frontage on Bell Road, the location offers an abundance of privacy and side street access. From the moment you enter you will feel the quality & appreciate the beautiful craftsmanship; features include a stunning kitchen w/quartz counters, wide plank oak flooring, oversized island, Viking appliances w/ 48" fridge, 6 burner gas range along with a wet bar w/wine fridge & walk in pantry! Adjacent family room w/fplc, formal dining room, living room & stunning office w/ walls of windows, Amazing master suite w/ spa like bath, soaking tub & oversized marble shower. 4 additional spacious bedrooms /2 en-suite, 2 car garage w/2 charging outlets, direct entry to mudroom w/ bench, bead board trim & cubbies. Great lower level Media/Game/Home Gym. In wall speakers & smart locks, Don't miss!

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

384 Washington Street Winchester MA 01890

Winchester, MA384 Washington Street

Price$1,299,000

Est. Mortgage: $/month

MLS Number 72891009

  • Single Family Attached
  • Bathroom 2
  • Bedrooms 5
  • Rooms 11
  • Square Feet 4,104

No one strives for ordinary, so why do so with your home purchase? Quite possibly the most unique property offering in Winchester! This home lends itself beautifully to multi-generational or extended families, or those simply looking for some extra space and privacy. 384 Washington Street boasts 5 bedrooms, 2 living rooms, 2 dining rooms, a beautifully renovated kitchen, an additional kitchenette, and 2 full bathrooms. Who doesn't like 2 for the price of 1?! The front farmers porch is a true delight and the perfect place to sit and enjoy a morning cup of coffee. If you stay in your PJs a little longer and prefer more privacy, the fenced in (private) backyard with oversized patio is the perfect option! Located just over a 1/2 mile to Winchester Center. Walk to shops, restaurants, the commuter rail station, and more! Perhaps best of all, this home sits on the corner of Washington Street and Bates Road where the coveted Muraco Elementary School can be found.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

15 Vinson Circle Winchester MA 01890

Winchester, MA15 Vinson Circle

Price$2,399,000

Est. Mortgage: $/month

Price Changed

MLS Number 72890643

  • Single Family Attached
  • Bathroom 4
  • Rooms 7
  • Bedrooms 5
  • Acreage 0.98

For the first time in over 25 years presents the rare opportunity to acquire one of the most exclusive and private lots in Winchester. The 1 acre property sits on an immaculately manicured landscape. Laid out with a wide open floor plan, creating endless opportunity for any family. Floor to ceiling windows fill the home with an abundance of natural light. 4 bedrooms, 2.5 bathrooms and an attached in-law suite which includes a full bathroom, kitchen / cabinetry, with access from the garage and private exterior access. The kitchen includes four ovens, gas stove, a skylight and double sliding glass doors that leads to the back deck filling the room with natural light throughout the day. Two extra large sheds in backyard for storage. Four water fountains, gazebo with deck space, and a courtyard with grilling station make this property an entertainers dream. 3 min walk to Vinson Owen Elementary School. House also features a large indoor pool that's currently covered but can be reopened.

Listed by Kevin Diarbakerly of Christine Boncore

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

5 Upland Road Winchester MA 01890

Winchester, MA5 Upland Road

Price$850,000

Est. Mortgage: $/month

MLS Number 72890386

  • Single Family Detached
  • Bathroom 3
  • Rooms 11
  • Bedrooms 3
  • Square Feet 2,113

Perched up high proudly sits this lovely 1930s old style colonial. Fresh and pristine, this meticulously maintained 3 bed 2.5 bath home is filled with character, charm & quality craftsmanship. Hardwood floors throughout with ample living space and natural light fill the home. The first floor offers an updated kitchen, master bedroom, dining, substantial living room and enclosed front porch. Two oversized bedrooms with generously size closets and a full bath are upstairs. The versatile lower level offers a living space perfect for a den or home office, full bath, laundry and storage. There's a spacious well-manicured backyard and detached 1 car garage and plenty of parking. Live in as-is or create your own vision, this home offers a multitude of opportunities. Convenient location walkable to Lynch Elementary school, Horn Pond Reservation, Tri-Community Bike Path. Easy access to commuter rail and minutes to downtown shops and restaurants.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

5 A Fernway Winchester MA 01890

Winchester, MA5 A Fernway

Price$3,395,000

Est. Mortgage: $/month

Open House

MLS Number 72884501

  • Single Family Detached
  • Next Open House: Sat 09/25 1:00 pm. to 3:00 pm.
  • Village Myopia Hill
  • Bathroom 6
  • Rooms 12

EXCEPTIONAL FIND! BETTER THAN NEW, much improved and customized with designer fixtures and quality elegant,timeless finishes, allow for immediate easy living & enjoyment. Enter a stunning living-room with fireplace from the 2 story hall, elegant dining-room, 2 Bespoke customized home-offices.A fully equipped Gym for your convenience.Enjoy the Cooks kitchen with 6 Burner cooktop & large island, eat in area, family-room w/fireplace and deck all connect for entertaining family and friends. Custom 3 car garage connects to the mudroom. A gracious staircase leads to the owners suite with gorgeous bath and walk in closet. Guest room with ensuite bath, 2 Bedrooms share a bath, 5th BR used as a home office with walk in closet. Bonus walk up ready for your finish. Fantastic lower full walkout above ground level, w/ recreation/Br,1200 bottle Wine-cellar, Kitchenette by Bespoke,marble bath with walk in shower and more. Exclusive, much sought after "MYOPIA HILL" Winchester CC, golf course location.

Listed by Dorothea Feffer of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

4 Bellevue Avenue Winchester MA 01890

MLS Number 72881799

  • Single Family Detached
  • Bedrooms 4
  • Rooms 9
  • Bathroom 3
  • Square Feet 2,900

Spacious, updated custom colonial in the coveted Muraco school district is a must see. Located in a wonderful family neighborhood with convenient access to Boston. This home feels like a retreat, settled back from the road with loads of indoor/outdoor living and garden space on this oversized lot. The first floor features an open concept living space with a large entranceway with storage and closet, a cozy sitting room with fireplace, dining room, spacious living room and a second, bright family living space for kids or office.The kitchen is a chef's dream with custom cherry cabinetry, Sub-Zero fridge, and Wolf range and large island for breakfast or study time. Second floor has four bedrooms with towering ceilings and plenty of closet space. Master bedroom leads to ensuite with bath, shower and closet. Laundry area is off the hall. Wrap around deck provides extra outdoor living space. Two car, two story garage and garden storage round out this inviting, family focused property.

Listed by Carolyn Vernaglia of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

260 Forest Street Winchester MA 01890

Winchester, MA260 Forest Street

Price$1,100,000

Est. Mortgage: $/month

MLS Number 72882881

  • Single Family Detached
  • Bathroom 3
  • Rooms 15
  • Bedrooms 5
  • Acreage 0.42

This spacious Winchester single-family is available now! On the main floor, you will find a kitchen with granite countertops and stainless appliances, a dining room, a living room with fireplace, and a half bath - Truly a great space for entertaining. On the second floor, there is a master suite, three additional bedrooms, and a full bath. Large mudroom area off of the two-car garage which leads to the fifth bedroom, a laundry room, and stairway to the finished basement space. No Showings until open house. OFFERS DUE TUESDAY 9/14 BY 5PM

Listed by Mark Gullifer of Cameron Real Estate Group - Framingham

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

139 High Street Winchester MA 01890

Winchester, MA139 High Street

Price$979,000

Est. Mortgage: $/month

MLS Number 72879748

  • Single Family Detached
  • Bathroom 2
  • Rooms 6
  • Bedrooms 3
  • Acreage 0.51

Fantastic opportunity to live on the West Side of Winchester. This charming, well maintained cape sits high on a beautifully manicured oversized lot. Great potential to invest your own sweat equity or there is plenty of room to expand and build your dream home. Hard wood floors throughout. Three season porch. So much potential, bring your vision and creativity!! Sold "as is".

Listed by Carol Ciffolillo of William Raveis R.E. & Home Services

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

24 Border Street Winchester MA 01890

Winchester, MA24 Border Street

Price$538,234

Est. Mortgage: $/month

Active With Contract

MLS Number 72876889

  • Single Family Detached
  • Bathroom 1
  • Rooms 7
  • Bedrooms 3
  • Acreage 0.06

Great opportunity to have a Winchester address! This home is located on a corner fenced in back yard with a maintenance free private deck to enjoy summer days & evenings. The home features a newer heating system, hot water heater, 7 rooms, 3 bedrooms , 1 full bath and a pull down attic . Bring your ideas and put your personal touches to make it your very own. It is possible that there is hard wood under the carpet. Appliances include stove, refrigerator, and washing machine, Basement has washer and dryer hook ups. Convenient to major highways and public transportation.

Listed by Constance Doto of Connie Doto Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

254 Main Street Winchester MA 01890

Winchester, MA254 Main Street

Price$1,689,000

Est. Mortgage: $/month

MLS Number 72873085

  • Single Family Detached
  • Village Downtown location
  • Bathroom 3
  • Rooms 10
  • Bedrooms 4

Must see this stunning and very spacious home! Set on an oversized lot with great rear yard just outside the vibrant town center; this sprawling 10 room, 4 bedroom 2.5 bath home w/ 3 car garage will exceed your expectations! Recently renovated and expanded this great home has the look and feel of a colonial from the exterior yet offers a stunning redesigned open concept kitchen w/ great room addition on the rear w/soaring ceilings, amazing space and contemporary flair! The high end kitchen is the heart of the home with wonderful flow for entertaining, island seating and adjacent wine bar. Great room off kitchen with breathtaking space, vaulted ceilings, double gas fireplaces and sliders to spacious deck overlooking the rear yard. Pantry storage, mudroom & laundry all just off the kitchen. Formal dining, living room w/fplc. & sunroom/family room complete this floor. The second features 4 bedrooms, a grand master w/ vaulted ceilings & private bath plus 3 add'l bedrooms and full bath.

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

114 Main Street Winchester MA 01890

Winchester, MA114 Main Street

Price$849,900

Est. Mortgage: $/month

Active With Contract

MLS Number 72868918

  • Single Family Detached
  • Bathroom 2
  • Bedrooms 3
  • Rooms 7
  • Lot Description Paved Drive

Lovely 3 bedroom, 1.5 bath raised ranch home with gas fireplaces on each level. Move in condition! This home has been well maintained. Family room was added on with rubber roof. The lower level offers a large finished playroom with gas fireplace that leads to the garage or to the unfinished laundry room with exterior access. Patio in back with stairs that lead up to a large sprinklered backyard with storage shed. Front yard is sprinklered as well. Enjoy central air in the summer and 2 gas fireplaces in the winter! Perfect location to enjoy all that Winchester has to offer, approx. 1/2 mile to Wedgemere Commuter Rail and 1 mile to Winchester Center, the library and McCall Middle School. On public transportation route! Refrigerator, Washer, Dryer are gifts from the Seller.

Listed by Kristen Mulkerin of J. Mulkerin Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

9 Trinity Road Winchester MA 01890

Winchester, MA9 Trinity Road

Price$1,159,000

Est. Mortgage: $/month

Open House

MLS Number 72868665

  • Single Family Detached
  • Next Open House: Sun 09/26 2:00 pm. to 3:00 pm.
  • Bedrooms 3
  • Bathroom 3
  • Rooms 8

Welcome to Winchester! This mid-century Ranch single family home is ready to move-in. Gleaming hardwood floors throughout. A modern eat-in kitchen featuring stainless steel appliances & commercial hood. The dining room is perfect for entertaining & opens to the sunken living room w/ fireplace. A separate office/family room has new carpeting w/ plenty of natural sunlight. Master bedroom is spacious & has an en-suite bathroom. Two additional large bedrooms & full bathroom complete the main living area. A partially finished newly carpeted basement has a wonderful media room w/ fireplace, laundry room, half bath & plenty of storages! Exterior features includes an oversized enclosed heated patio with skylights and sliders for outdoor access. Nice sized lot with a storage shed and a one car garage. This home has much potential for expansion. Located on a quiet cul-de-sac, Vinson Own school district, and near Winchester Golf Club, Mystic Lakes. Wright-Locke Farm, Whipple Hill & so much more!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

282 High Street Winchester MA 01890

Winchester, MA282 High Street

Price$3,300,000

Est. Mortgage: $/month

MLS Number 72867636

  • Single Family Detached
  • Bathroom 5
  • Rooms 16
  • Bedrooms 6
  • Acreage 0.56

Stunning family compound setting built with pride & quality offered for first time.Once in a generation opportunity.Uniquely generous in size and scale.Light filled,modern all brick home abundant in space and comfort.Unrivaled privacy at end of cul-de-sac.Masterfully built staircase presents the two story great room with double sided fireplace.Spacious kitchen with island, double gas range, and 66" of refrigeration.Grand formal dining room,serving pantry,dinette,and fabulous living room make up the first floor common areas.Add a main level bedroom,seperate full and half baths,and large office complete the primary level.Upstairs,open primary suite complete with stone fireplace,ensuite bath,and dressing room.Three additional bedrooms,big full bath,and laundry on second level.Full,finished walkout basement with kitchen,living area,brick oven,fireplace,dinette,and additional 6th bedroom and bathroom ideally suited for in-law,au pair,or multigenerational suite.Rare,attached 4 bay garage.

Listed by Anthony Marino of Marino Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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 Fletcher Street Winchester MA 01890

Winchester, MA16 Fletcher Street

Price$1,199,900

Est. Mortgage: $/month

MLS Number 72865876

  • Single Family Attached
  • Village Flats
  • Bathroom 3
  • Rooms 11
  • Bedrooms 3

If you missed out on the 1st unit the 2nd is now complete & ready for you to move right in & enjoy this stunningly gut renovated townhome located in Winchester's desirable neighborhood, “The Flats”. This 3-bedroom, 2.5 bath unit w/ 2148 sq ft. of living space feels like a single-family home. The 1st floor is light-filled & impressive w/ hardwood floors, custom woodworking & wainscoting finish. The high-end kitchen offers a large seated island, granite counters, gas stove w/ direct vent hood & plenty of cabinets. There are 2 spacious bedrooms, full bath, office & laundry on the 2nd level. Walk-up to the primary bedroom suite on the 3rd floor, your own personal retreat. Stay organized easily w/ 2 custom closets, private full bath w/ luxurious tiled walk-in shower & glass door. The finished basement offers flex space that would be perfect as a family room or playroom & includes additional storage room. Coveted location for commuters, minutes to dining, shopping & top-rated schools.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

350 South Border Road Winchester MA 01890

Winchester, MA350 South Border Road

Price$1,095,000

Est. Mortgage: $/month

MLS Number 72862834

  • Single Family Detached
  • Bathroom 3
  • Rooms 7
  • Bedrooms 3
  • Acreage 0.35

This beautifully maintained 3 bedroom/2.5 bathroom split-level home it sited on a gorgeous large, flat backyard which includes an expansive two level outdoor deck that is an ideal space for outdoor dining and entertaining. The recently renovated kitchen has a large, granite island coupled with cathedral ceilings that opens up to the living & dining room thats perfect for entertaining. Other features include: beautiful hardwood flooring, skylights, Central A/C, oversized 2 car attached garage, large shed, finished lower level that walks out to a large deck. Lower level can easily add a 4th bedroom with a full bathroom - see floor-plan attached. Located just off 93 and in the heart of the Middlesex Fells Reservation where you can hike, bike, snow shoe or cross-country ski! 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 The David Green Group and David Green of Coldwell Banker Realty - Back Bay

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

63 Irving Street Winchester MA 01890

Winchester, MA63 Irving Street

Price$1,295,000

Est. Mortgage: $/month

MLS Number 72862034

  • Single Family Detached
  • Bathroom 3
  • Rooms 9
  • Bedrooms 4
  • Square Feet 2,587

 View the digital brochure This spacious four bedroom, two and a half bath Colonial is your perfect summer destination with a fully fenced back yard, beautiful 18' x 34' inground pool, patio, bar, hot tub, and a shed for all of your pool toys. Adjacent to the Tri-Community Greenway on a dead end street with a walking path to Muraco School and Leonard Field. Sun-filled living room with picture window, fireplace, and recessed lights. Kitchen with granite counters and a back yard view. Slider from the dining room leads to a wrap-around sun porch with a slider to the patio and pool area. The first floor also has a half bath, mud room, and attached garage. There's a large bedroom with a walk-in closet over the garage, plus three bedrooms and a full bath over the main house. Great attic storage. Finished lower level family room with stone fireplace, bar, full bath, and laundry. A mile to Winchester Center, shops, restaurants, and commuter rail, or Winchester Hospital and Middlesex Fells Reservation. Welcome Home!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

17 Wickham Road Winchester MA 01890

Winchester, MA17 Wickham Road

Price$1,299,999

Est. Mortgage: $/month

MLS Number 72856445

  • Single Family Detached
  • Bedrooms 3
  • Rooms 6
  • Bathroom 3
  • Lot Description Wooded,Paved Drive

Perfectly located on a quiet street in a highly desired area of Winchester. A custom and well built home perfect for entertaining now awaiting its new owners and the opportunity to update its 4227 sq. ft. of spacious living area to make it their own. Features include 2 fireplaces, large living and dining room, and spacious finished basement including a wine cellar. Only a few miles from Boston, close to major highways and Winchester commuter rail. Come experience everything Winchester has to offer including shops, restaurants, and top rated schools. Sold "as is".

Listed by Erin Nolan of Shibilia Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.86% last updated on Sep 16, 2021
* 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

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.