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Homes for Sale Winchester MA

Winchester, Massachusetts is 8 miles north of Boston. Winchester is child-friendly and home to lakes, parks, and trails. Winchester keeps its public spaces well maintained. Winchester is a family-friendly bedroom community. 

Discover Winchester Real Estate

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60 Emerson Road Winchester MA 01890

Winchester, MA60 Emerson Road

Price$1,600,000

Est. Mortgage: $/month

Open House

MLS Number 72896521

  • Single Family Detached
  • Next Open House: Sun 09/19 11:30 am. to 1:00 pm.
  • Village West Side
  • Bathroom 3
  • 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.

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18 Berkshire Drive Winchester MA 01890

Winchester, MA18 Berkshire Drive

Price$1,090,000

Est. Mortgage: $/month

Open House

MLS Number 72895354

  • Single Family Detached
  • Next Open House: Sun 09/19 11:30 am. to 1:00 pm.
  • Rooms 8
  • Bedrooms 4
  • Bathroom 3

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 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.

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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.

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8 Westland Avenue Winchester MA 01890

Winchester, MA8 Westland Avenue

Price$1,700,000

Est. Mortgage: $/month

Open House

MLS Number 72894282

  • Single Family Detached
  • Next Open House: Sun 09/19 12:00 pm. to 2:00 pm.
  • Bathroom 3
  • Rooms 11
  • Bedrooms 4

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.

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19 Hancock Street Winchester MA 01890

MLS Number 72893699

  • Single Family Detached
  • Bedrooms 5
  • Bathroom 2
  • Rooms 11
  • Acreage 0.34

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.

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.

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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.

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28 Elm Street Winchester MA 01890
Contingent

MLS Number 72891222

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,221

Location, location, location! This charming freestanding antique townhome offers 3 floors of living space with 2 bedrooms, 1.5 baths, and is located just steps from Winchester Center. This lovely residence includes loads of natural sunlight, an updated kitchen, stainless steel appliances, hardwood floors, updated windows, and systems. Nothing to do but move in! Enjoy a walk to Starbucks or stop into one of the newest trendy shops and restaurants in town. Take a ride on the Commuter Rail to go to work or enjoy a beautiful day or evening in Boston. This adorable home feels like a Beacon Hill brownstone with the warmth of a suburban neighborhood. Perfect for a young or downsizing couple. Includes 2 off-street parking spaces. Do not miss the opportunity to purchase this beautiful free-standing condominium with the benefit of no fees!

Listed by Beverly Dagostino 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.

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139 High Street Winchester MA 01890

Winchester, MA139 High Street

Price$979,000

Est. Mortgage: $/month

MLS Number 72891612

  • Land Residential
  • MLS Status Active
  • Acreage 0.51

Fantastic opportunity to live on the West Side of Winchester. Well maintained, beautifully manicured oversized lot. Great potential to build your dream home. Bring your vision and creativity!! Sold "as is". Complete rehab or tear down (house on property) Seller makes no representation or warrantee. Buyer to do due diligence.

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.

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400 Cross Street Winchester MA 01890
Open House

MLS Number 72891506

  • Condo or Co-op
  • Next Open House: Sun 09/19 1:30 pm. to 2:30 pm.
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,529

Welcome to this beautifully maintained townhouse that is move-in ready and conveniently located within a short distance to the very desirable Winchester Town Center! Numerous options for shopping and dining. Not to mention proximity and access to commuter rail, 93 and 95 highways. This spacious townhome is an end unit with three levels. Attached one car garage with interior access from the unit. First floor features a large bedroom with a full bathroom and have plenty of storage space. 2nd floor has an open concept living/dining room with fireplace and access to a private deck. Kitchen features updated stainless steel appliances, granite countertop and quaint eat-in kitchen perfect for morning coffee. 1/2 bath completes the second floor. 3rd floor has an oversized master bedroom with en-suite bathroom and two closets. 3rd floor laundry. A great home with lots of potential!

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.

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19 Hancock Street Winchester MA 01890

MLS Number 72891366

  • Multi-Family 2 Family
  • Total Parking Spaces 10
  • Year Built 1915
  • Bathroom 2
  • Units 2

Attention investors and owner occupants! Classic two family located on quiet street in Winchester Highlands, close to I-93, bus, and commuter rail. Walking distance to The Fells Reservation, perfect for hiking, biking, or walking your dog. Close proximity to downtown Winchester with shops, restaurants, 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. 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.

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.

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15 Vinson Circle Winchester MA 01890

Winchester, MA15 Vinson Circle

Price$2,599,000

Est. Mortgage: $/month

MLS Number 72890643

  • Single Family Attached
  • Bedrooms 5
  • Rooms 7
  • Bathroom 4
  • Square Feet 4,511

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.

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384 Washington Street Winchester MA 01890

Winchester, MA384 Washington Street

Price$1,299,000

Est. Mortgage: $/month

Open House

MLS Number 72891009

  • Single Family Attached
  • Next Open House: Sun 09/19 11:30 am. to 1:00 pm.
  • Rooms 11
  • Bathroom 2
  • Bedrooms 5

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

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