Winchester Luxury Homes

Known for its affluence and beauty, Winchester has some truly luxurious homes for sale. All priced over $800,000, you'll find a range of Winchester homes, from new construction mansions to contemporary condos- all with the finest features and amenities. 

Know exactly what you want? Use the options on the right to further refine your search.

Register to save your favorite homes in Cambridge, save your searches, and receive notification when a new listing matches your criteria.

 

39 Myopia Road Winchester MA 01890

Winchester, MA39 Myopia Road

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72574074

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Village Myopia
  • Year Built 1966

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: 3.6% last updated on Jan 23, 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 A VisitAsk A QuestionMore Details

16 Fenwick Road Winchester MA 01890

Winchester, MA16 Fenwick Road

Price$2,399,000

Est. Mortgage: $/month

MLS Number 72583824

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 2019
  • Full Bath 6

Spectacular New Construction home with great curb appeal! This gambrel colonial home features 5 bedrooms, & 5 baths & is currently under construction by top local builder; to be complete Dec/Jan. This beautiful home with ideal layout features an oversized 2 car garage, direct entry into mudroom a gorgeous kitchen with high end appliances, 9' center island, sliders to rear yard, adjacent family room, formal living and dining w/ butlers pantry. 1st floor guest bedroom suite w/adjacent full bath, or first floor office. Grand master with 2 rooms, huge walk in closet, and lavish bath~ finished third level offers 5th/6th bedroom and full bath. Designer finishes throughout and a top location close to Wedgemere train station and the town center! Ambrose school don't miss out! Call list agent for a private accompanied showing.

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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 A VisitAsk A QuestionMore Details

5 Dean Road Winchester MA 01890

Winchester, MA5 Dean Road

Price$2,235,000

Est. Mortgage: $/month

MLS Number 72582583

  • Single Family
  • Garage 3
  • Parking Spaces 6
  • Year Built 2019
  • Full Bath 5

BEAUTIFUL NEW CONSTRUCTION in Winchester's Muraco school district, recognized by the state for its outstanding 2019 MCAS achievement! This STUNNING 6-bedroom, 5-bath home with approx. 6125 sq. ft. of living space offers extraordinary comfort for the entire family, and the details throughout are absolutely exquisite. The sun-filled main level boasts a grand two-story foyer, living & dining rooms, gorgeous high-end kitchen w/ elegant cabinetry, large family rm. w/ fireplace, sitting rm., office area, + a guest bdrm & full bath. Second level has 4 spacious bdrms., including a fabulous master en-suite w/ soaking tub, striking tile, his/her sinks, + jetted shower; there are 2 more full baths, and laundry. Lower level offers GREAT spaces; exercise rm., playroom, media room, mudroom, + bedroom & full bath. The top floor is +900 sq. ft. of unfinished storage space. There's a 3 car garage, + terrific level back yard. Welcome home!

Listed by Anne Spry and Jane Byrne of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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 A VisitAsk A QuestionMore Details

14 Harrison Street Winchester MA 01890

Winchester, MA14 Harrison Street

Price$2,200,000

Est. Mortgage: $/month

MLS Number 72609731

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Village The Flats
  • Year Built 1905

Magnificent Dutch Colonial in highly desirable Winchester Flats neighborhood. Exquisitely renovated and expanded, this exceptional property blends traditional elegance with spectacular modern day features and upgrades. Impressive custom improvements include: three story addition, gourmet eat-in kitchen w/ oversized center island, dry bar, top of the line appliances, quartzite Taj Mahal countertops, walk-in pantry, spacious family rm w/ built-ins and gas fireplace, two car garage built in 2018, mudroom, 1st fl private office, master bedroom suite with generous closets and storage, luxurious marble bathroom with glass shower and soaking tub, full finished third floor, 2nd floor laundry/craft room, upgraded systems and custom storage throughout. Conveniently located a short distance from downtown Winchester shops/restaurants, train to Boston (15min ride to North Station) and elementary/middle/high schools. This is the ideal property to call home. - O.H.s 1/25 & 1/26 from 12-2:00 p.m.

Listed by McGlynn Splaine Team, Michele McGlynn and Jenny Splaine of Berkshire Hathaway HomeServices Commonwealth Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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 A VisitAsk A QuestionMore Details

12 Priscilla Lane Winchester MA 01890

Winchester, MA12 Priscilla Lane

Price$1,899,000

Est. Mortgage: $/month

MLS Number 72561811

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 2019
  • Full Bath 3

Beautiful NEW CONSTRUCTION Home on the East Side! Ready for occupancy late December/January~ This exquisite 5 bedroom 3.5 bath colonial features desirable open floor plan for today's family living! Thoughtfully designed with high-end finishes & details, this home offers an oversized 2-car garage, direct entry into mudroom, gourmet kitchen w/ island & Chefs appliances, family room with FP adjacent to kitchen & direct exterior access to patio. sun-drenched formal LR & DR with crown molding ~ Second floor features include master suite w/ double 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. Private rear yard w/ sliders from kitchen leading to patio. This home is located in sought after East side of town, convenient to the center, Lincoln school district, and great neighborhood!

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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 A VisitAsk A QuestionMore Details

326 Highland Avenue Winchester MA 01890

Winchester, MA326 Highland Avenue

Price$1,840,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72551945

  • Single Family
  • Garage 2
  • Parking Spaces 8
  • Year Built 1903
  • Full Bath 2

Close to Winchester Center, and one of the most beautiful homes you will ever see! Impressive both inside and out with detail and craftsmanship unlike any other & a floor plan ideal for both casual family living and formal entertaining! ~ Many updates include recent blown in insulation, central air, updated electrical, new roof, updated heating system, Situated proudly on a private, oversized lot with lovely LEVEL rear and side yards w/patio, decks and spacious 2 car garage; very close to the town center offering some of the most gorgeous custom hand milled woodwork you've ever seen~ Breathtaking bridal staircase with high ceilings & spectacular stained glass windows, from one room to the next, this home will impress. Formal Mahogany dining room with beamed ceilings and oversized fireplace, living and family rooms each w/ fireplaces~4 bedrooms, on second floor, Master with french doors to sunroom/enclosed balcony... must see!

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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 A VisitAsk A QuestionMore Details

10 Lawrence Street Winchester MA 01890

Winchester, MA10 Lawrence Street

Price$1,665,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72602146

  • Single Family
  • Garage 1
  • Parking Spaces 3
  • Year Built 1966
  • Full Bath 3

Wonderfully redesigned center entrance colonial in picture perfect setting in the Flats neighborhood! The home is currently about to enjoy the finish stages of redesign and development. Some features include: All new windows, electrical, plumbing, HVAC and fully insulated, New mud room area and 1/2 bath, Open kitchen concept with views of expansive and secluded backyard space right from the brand new island area, Master Suite with walk in closet and gorgeous brand new bath, Bonus basement area with kitchenette and full bath. Completion date roughly end of February. Price reflects $15k allotment for landscaping in the spring. Also, if buyer has interest, detached 2 car garage can be built for additional $100k.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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 A VisitAsk A QuestionMore Details

508 South Border Road Winchester MA 01890

Winchester, MA508 South Border Road

Price$1,649,900

Est. Mortgage: $/month

MLS Number 72483056

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 2020
  • Full Bath 4

This beautiful new construction, three level Colonial home is a must see, ready for a 6 week move in! Located across the street from Middlesex Fells Reservation, this is the perfect location for everything Winchester has to offer. This home will feature gorgeous finishes including eat-in kitchen with new quartz counters, stainless steel appliances and formal dining room. The spacious rooms through-out the home include a finished basement with full size windows, and finished 3rd floor with a 5th bedroom and bonus room! Property will have underground lawn irrigation, to help maintain the exterior of this gorgeous property!

Listed by Gary J. Litchfield and Brittany Gray of Mass. Real Estate Solutions, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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 A VisitAsk A QuestionMore Details

379 Main Street Winchester MA 01890

Winchester, MA379 Main Street

Price$1,599,000

Est. Mortgage: $/month

MLS Number 72536636

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Year Built 1846
  • Full Bath 3

Own a piece of Winchester history when you move into this handsome updated home with an open sunny floor plan. Imagine not needing your car for everything; only a 5-10 min walk to town center, train, and schools. The 21 x 15 kitchen flows into the spacious 21 x 21 skylit family room with gas fireplace and large screen TV. On the second floor there are 3 bedrooms and a laundry. At the end of the day, retreat to your fireplaced master suite with custom designed bathroom and walk-in closet. With 2 more bedrooms and a full bath on the 3rd floor you have options for more family bedrooms, an office, or a nanny suite. Of course there is AC and gas cooking and heating. Time to create your memories here.

Listed by Judith Ober of Berkshire Hathaway HomeServices N.E. Prime Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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 A VisitAsk A QuestionMore Details

516 South Border Road Winchester MA 01890

Winchester, MA516 South Border Road

Price$1,589,900

Est. Mortgage: $/month

MLS Number 72583994

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Year Built 2020
  • Full Bath 4

This gorgeous new Colonial home has finished basement and attic! Located across the street from Middlesex Fells Reservation, this is the perfect location for everything Winchester has to offer. This home will feature gorgeous finishes including eat-in kitchen with new quartz counters, stainless steel appliances and formal dining room. The spacious rooms through-out the home include a finished basement with full size windows, and finished 3rd floor with a 5th bedroom and bonus room! Property will have underground lawn irrigation, to help maintain the exterior of this gorgeous property!

Listed by Gary J. Litchfield and Brittany Gray of Mass. Real Estate Solutions, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.6% last updated on Jan 23, 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 A VisitAsk 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.