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Homes in Winchester MA

Winchester MA offers excellent access to metropolitan Boston making it a popular place to live. Single family homes are a sound solution to living eight miles from Boston. View frequently updated Winchester MA real estate listings below. You might also be interested in viewing all Arlington Area homes for sale.

Tour Single Family Homes in Winchester MA

Contact Sweeney & O'Connell Real Estate online or call 781.643.7478 with any questions or to schedule a private tour.

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3 Pilgrim Drive Winchester MA 01890

Winchester, MA3 Pilgrim Drive

Price$2,399,000

Est. Mortgage: $/month

MLS Number 72761553

  • Single Family Detached
  • Village West Side
  • Bathroom 5
  • Rooms 15
  • Bedrooms 5

Spectacular one of a kind home situated on a premiere lot offering almost an acre of level land! If you are looking to build a pool or tennis court or even both, this could be your chance! This home has been beautifully expanded and renovated by a top builder offering over the top quality and designer finishes creating this 6,000 sf masterpiece! This chic, custom designed home has an expansive floor plan w/space for the entire family to enjoy! First floor direct entry 2-car garage leads into great mudroom, gorgeous kitchen with induction stove, high end appliances, & quartz counters .. adjacent breakfast room plus family room w/ gas fplc, dining room, formal living w/ add'l fplc, First floor master suite w/ office / sitting room and lavish spa-like bath! Stunning second family room with walls of windows will for sure be your favorite room, overlooking gorgeous, expansive rear yard! Second floor offers 2nd master en-suite option lower level full walk out / use as gym/ media/ game room.

Listed by Kim Covino of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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.

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17 HOLLYWOOD Road Winchester MA 01890

Winchester, MA17 HOLLYWOOD Road

Price$1,399,900

Est. Mortgage: $/month

MLS Number 72760799

  • Single Family Detached
  • Village East Hill
  • Bathroom 5
  • Rooms 8
  • Bedrooms 5

You'll fall in love with this beautiful Custom Built Colonial in this coveted East Hill neighborhood. This attractive home is over 4500 SF & features 9 rooms, 5 bedrooms including dual Master Bedrooms, 5 Baths, open concept Kitchen & Family room, 1st Floor Master addition is spacious with a sizable walk in closet, built in office area and a premium bath en suite. Beautiful front to back Living Room with fireplace too! 2nd Floor offers 4 bedrooms, 2 baths & plenty of closet space. Lower Level includes another finished family room with fireplace & a walk out to a patio. 2 car garage. This home is perfect for modern family living & perfect for entertaining too. Easy access to major highways & only 8 miles to Boston. Enjoy the Middlesex Fells Reservation too! Close to the T & to downtown Winchester resplendent with Restaurants, Coffee bistros & unique shops. Don't miss this opportunity to live in one of Winchester's favorite neighborhoods. View floorplans & Matterport online.

Listed by Jan Triglione Team and Jan Triglione of Premier Realty Group, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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.

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1 Windsong Lane Winchester MA 01890

Winchester, MA1 Windsong Lane

Price$1,575,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72758770

  • Single Family Detached
  • Bathroom 4
  • Rooms 10
  • Bedrooms 5
  • Square Feet 4,875

This gorgeous ranch home was thoughtfully designed as an entertainer's dream, inside & out! Huge lower level is custom-built for sports lovers, featuring an exercise room w/ sauna, 3/4 bathroom, mini kitchen, gorgeous built-in bar, walk-in cedar closet & even a built-in ping pong table! Main level boasts a recently renovated chef's kitchen offering custom cabinets, silestone counters & Bosch appliances, including double dishwashers! Oversized kitchen includes both eat-in & bar seating as well as separate desk & mudroom spaces. In addition to 4 sizable bedrooms, enjoy a private master suite w/ ensuite bath. Spacious family room is highlighted by a marble fireplace & slider leading out to your new backyard oasis! Enjoy a heated pool w/ diving board, surrounded by bluestone patio w/ built-in fireplace. 2 car garage w/ circle driveway, located on quiet cul de sac in new VO district. Entertain all year long!

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

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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.

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5 Grant Road Winchester MA 01890

Winchester, MA5 Grant Road

Price$999,000

Est. Mortgage: $/month

MLS Number 72758868

  • Single Family Detached
  • Bathroom 3
  • Rooms 7
  • Bedrooms 3
  • Square Feet 2,592

This one-owner, three bedroom Ranch style home has been beautifully maintained and is close to major commuting routes. Located in the Muraco School District, you will enjoy its bright, open concept living room, which is perfect for entertaining. There is also a wood-burning fireplace and a large bow window which overlooks the front yard. The dining room leads to a large den which is adjacent to the spacious back-yard. Upon entering the two-car garage you have access to the finished lower level with a second fireplace. Don't miss this great opportunity!!

Listed by Nancy O'Herron and Sal Dipinto of Coldwell Banker Realty - Winchester

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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.

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49 Thornberry Road Winchester MA 01890

Winchester, MA49 Thornberry Road

Price$1,399,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72757514

  • Single Family Detached
  • Bathroom 3
  • Rooms 8
  • Bedrooms 4
  • Square Feet 2,600

COMPLETELY RENOVATED SINGLE FAMILY! A short drive to downtown where you'll find plentiful boutiques, restaurants, coffee shops and the Commuter Rail to North Station. Within the 4-year old Vinson Owen School district. The first floor features an open floor plan for today's modern lifestyle, with a fireplace living room, dining room, and kitchen boasting a top of the line SS appliance package and Quartz counters, a perfect place to host your family for the holidays. Hardwood floors throughout and plenty of natural light. Experience the great outdoors featuring 2 large composite decks and a spacious back yard for your children to play catch with Rover. 3 bedrooms and 2 bathrooms are located on the second floor, including the master with gorgeous en-suite bathroom. The lower level features another bedroom, a full bath, access to the exterior and family room with fireplace #2. Easy access to major highways and 7 miles from Boston.

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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.

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22 Mayflower Road Winchester MA 01890

Winchester, MA22 Mayflower Road

Price$1,275,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72754941

  • Single Family Detached
  • Bathroom 3
  • Rooms 8
  • Bedrooms 4
  • Square Feet 2,820

**Multiple offers, highest/best due on Friday November 20th at Noon** An exceptional opportunity abutting the Winchester Country Club. Renovate, expand or design your dream home. The options are endless for this never before offered home. Enjoy spectacular sunrises and long views from the 4 bedroom 2 -1/2 bath home. Absolutely gorgeous golf course lot with winter views of Boston. Come take a look at this Diamond in the rough!!

Listed by Ronald Buck of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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.

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2 Hastings Road Winchester MA 01890

Winchester, MA2 Hastings Road

Price$1,949,900

Est. Mortgage: $/month

MLS Number 72752353

  • Single Family Detached
  • Bathroom 4
  • Rooms 8
  • Bedrooms 5
  • Square Feet 4,036

This Pristine Colonial Home is located on a lovely cul de sac in a very desirable Winchester neighborhood close to the town forest. Upon entering this home, you will be captivated by all the attention to detail, wonderful scale with tall ceilings and the excellent flow that leads you to the magnificent custom designed chef's kitchen which is the heart of this home. No expense was spared in this dream kitchen with very high end appliances featuring Wolf, Thermador, Subzero and Fisher & Paykel, hand stained custom cabinetry and the 11 ft. center island which offers perfect function and ease for everyday living and entertaining. The second floor offers a wonderful master bedroom suite with a beautiful master bath that includes a BainUltra tub, a steam shower and a custom designed walk in closet plus three additional bedrooms. The family room, exercise area and and private guest suite is found in the nicely finished lower level. Professionally landscaped lot. Truly Special, Don't Miss It!

Listed by Ida M. Bianco of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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.

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7 Aristotle Drive Winchester MA 01890

Winchester, MA7 Aristotle Drive

Price$1,575,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72749464

  • Single Family Detached
  • Bathroom 4
  • Rooms 10
  • Bedrooms 5
  • Square Feet 3,652

Are you looking for an overall incredible home with a recently renovated chef's kitchen? This kitchen features: Wolf cooktop, SubZero refrigerator, double ovens, custom cabinets and farmers sink. The kitchen is open to a sunken family room with gas fireplace and access to a three seasons heated sun room. This is the perfect home for entertaining! First floor bedroom or home office makes this a fantastic option for guests or when working from home. Master bedroom with updated on-suite bathroom and 3 additional bedrooms with 1 full bathroom complete the second floor. The finished basement is a great space if you need to expand as there is plenty of room for playroom, media room/home gym, and features a bar with sink. Enjoy the attached 2 car garage and spacious corner lot with mature landscaping large enough for a pool. The home is a short distance to recently renovated Vinson Owen Elementary.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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

109 Cambridge Street Winchester MA 01890

Winchester, MA109 Cambridge Street

Price$1,275,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72745473

  • Single Family Detached
  • Bathroom 4
  • Rooms 9
  • Bedrooms 6
  • Square Feet 3,050

OPEN HOUSES CANCELLED THIS WEEKEND! This striking hip roof Colonial is located just 2-tenths of a mile to Ambrose School and 1 mile to Winchester Center. Expansive rooms on all three finished levels, high ceilings, numerous critical updates inside and out, and meticulously restored period details include a handsome vestibule, welcoming foyer with stunning staircase, built-ins, & newly refinished hardwood floors throughout. The open formal rooms include a coffered ceiling dining room, butler's pantry, and fireplaced grand living room that opens to the front covered porch for all those outdoor gatherings. Formal rooms connect to a large updated country kitchen w/granite and SS appliances and a mudroom out to the patio and level backyard beyond. 2nd and 3rd floor sleeping quarters include a spacious owner's suite plus five additional bedrooms, offering lots of options for work and learn-from-home needs. All bathrooms updated.

Listed by The Lorrie Parajeckas Group and Lorrie Parajeckas of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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.

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30 Winthrop Street Winchester MA 01890

Winchester, MA30 Winthrop Street

Price$1,199,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72745092

  • Single Family Detached
  • Bathroom 3
  • Rooms 7
  • Bedrooms 3
  • Square Feet 2,042

ANTIQUE COLONIAL FARMHOUSE BURSTING WITH VINTAGE CHARM! Walking distance to Winchester's highly acclaimed schools & town center bustling with coffee houses & shops. Conveniently located near The Fells Reservation for the hiking enthusiast, and a commuter's dream, with the train to Boston not far away. Built in 1830, this home features original wide pine floors, an incredible front porch perfect for relaxing with a book or sharing a laugh with neighbors & friends. Welcoming first floor boasts a cozy living room for movie night, a beautiful dining room with bay windows & secret Butler's pantry which could be easily converted to a home office to accommodate your working demands. The spacious kitchen with stainless appliances & granite counters offers a sun filled breakfast nook & plenty of room for baking cookies with the kids. Upstairs are 3 generous bedrooms & 2 full bathrooms. The professionally landscaped yard, private bluestone patio & 3 car garage complete this true Winchester gem.

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 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.