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.

 

282 High Street Winchester MA 01890

Winchester, MA282 High Street

Price$3,600,000

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: 2.78% last updated on Jul 22, 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

28 A Surrey Road Winchester MA 01890

Winchester, MA28 A Surrey Road

Price$3,450,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72866554

  • Single Family Detached
  • Bathroom 6
  • Rooms 14
  • Bedrooms 5
  • Acreage 0.73

Fabulous new construction opportunity awaits you in Winchester. Spectacular floorplan with 14 magnificent rooms, 5 bedrooms, 5 1/2 baths. Winchester luxury living encompassing choice materials and tasteful design by well known Master Builder from Winchester. Casual elegance with features such as beautifully appointed culinary grade kitchen, large finished family room and office with full bath in basement, primary bedroom with den, tasteful mudroom, heated 2 car garage with hydraulic car lift for 3rd auto, and more! Full wet bar with dishwasher in open basement with full bath. Bar height outdoor seating under porch leads to full, outdoor Kitchen. Exceptional 31,800 square foot lot capable of an optional pool and pool house with striking optics overlooking the Ledges of Winchester. Popular neighborhood. Unmistakable benefits of New construction in a classic New England town with TOP rated schools. Built with perfection as a goal, and excellence as a result for one lucky Buyer.

Listed by Anthony Marino of Marino Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

11 Fieldstone Drive Winchester MA 01890

Winchester, MA11 Fieldstone Drive

Price$2,000,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72854846

  • Single Family Detached
  • Bathroom 5
  • Rooms 15
  • Bedrooms 4
  • Acreage 0.63

This meticulously maintained rarely available contemporary style home is beautifully sited on a private cul-de-sac of similar homes. All 15 rooms are generously sized and offer flexible space for everyone. Grab your favorite book and relax by one of two wood-burning fireplace living spaces. Gather the family around the table in the eat-in Chef's kitchen that offers Sub-Zero & Thermador appliances. This property offers flexible work/life balance with two office spaces along with home gym and large play room with built-in study areas. Imagine sipping your favorite beverage while taking in the private wooded backyard on the wraparound deck with access from every living area including a private patio off the Master Bedroom Suite. In addition to the four large bedrooms and three full baths there is a separate living space with private entrance offering additional 1500 Sq ft of living-dining-sleep & full bath, perfect for extended family or Au-pair. Private showings only.

Listed by Sheila McDougall of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

237 High Street Winchester MA 01890

Winchester, MA237 High Street

Price$1,899,000

Est. Mortgage: $/month

MLS Number 72862556

  • Single Family Detached
  • Village West Side
  • Bathroom 4
  • Rooms 11
  • Bedrooms 4

Modern French-style, farmhouse surrounded by conservation & within the Vinson Owen district!! This new construction lovingly designed 4 bedroom, 3.5 bathroom home is ideal for raising a family & enjoying everything Winchester has to offer, including a bustling downtown & 2 commuter rails to Boston. Exquisite attention to detail featuring shiplap walls, a fireplace with floor to ceiling stone surround & many luxurious light fixtures. The spacious floor plan is comfortable for entertaining & allows several locations to accommodate a home office. The kitchen is adorned with top of the line SS Jenn Air appliances, Quartz counters, tile backsplash & pot filler. The elegant master suite boasts a custom Boston Closet, modern wallpaper & spa bathroom with heated floors, Quartz double vanities & a deep soaking tub. The walkout lower level accesses a sprawling back yard for hosting family BBQ's & gathering around the fire pit with friends. Easy access to major highways & 7 miles North of Boston.

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

27 Cabot Street Winchester MA 01890

Winchester, MA27 Cabot Street

Price$1,875,000

Est. Mortgage: $/month

MLS Number 72869967

  • Single Family Detached
  • Village Flats neighborhood
  • Bathroom 4
  • Rooms 10
  • Bedrooms 4

Once upon a time... this storybook-like french country tudor is an opportunity you won't want to miss! This special home is situated on one of the most beautiful lots in the desirable flats area of Winchester and has been lovingly cared for through the years. The sprawling first floor features a charming entry foyer, mudroom, beautiful oversized living room with fireplace leading to a charming brick screen porch; formal dining room w/ custom mill work and built ins, butlers pantry china cabinets, eat in kitchen & attached garage complete the main level. The second floor offers a large master suite with sitting area, full bath & walls of windows overlooking the private gardens; plus two additional spacious bedrooms and full bath. The third floor suite includes a bedroom and full bath. The lower level features a grand family room/ media room with fireplace and high ceilings, a summer kitchen, laundry and utility rooms. This home is a rare find and one you will want to make your own!

Listed by Kim Covino of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

13 Gershon Way Winchester MA 01890

Winchester, MA13 Gershon Way, Unit 13

Price$1,787,500

Est. Mortgage: $/month

MLS Number 72809921

  • Condo or Co-op
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,550

PRICE IMPROVEMENT for this PRISTINE 3 bed, 2.5 bath end unit townhome at Winchester's Winning Farm, a gold medal award winner from NAHB for best 55+ community in the US. The layout offers great flexibility for today's lifestyle with superior quality and charm. The first floor open concept features living room with gas fireplace and large windows to let in loads of natural light and great views. The dining room has coffered ceiling and door to outside deck. The office/den is accessed through double French doors. The custom chef's kitchen has high-end appliances, quartz countertops, and large island. The 1st fl master suite has walk-in closet with custom shelving, door to outside patio, and bathroom with double vanity, walk-in shower with bench, and separate soaking tub. The second floor has two large bedrooms, full bath with walk-in shower and loft/open space. There is a two-car attached garage and approx 1300 sq ft in basement with high ceilings that offers many options for future use

Listed by Tom Doherty of Gibson Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

37 Foxcroft Road Winchester MA 01890

MLS Number 72862200

  • Single Family Detached
  • Bathroom 4
  • Rooms 11
  • Bedrooms 5
  • Acreage 0.26

Classic Center Entrance Colonial in one of Winchester's most desired locations , walking distance to the center of town,public transportation , parks, schools and town tennis courts. This fabulous home offers three levels of living space and unfinished basement, lovely spacious eat-in kitchen overlooking a private backyard and brick patio, enjoy the formal dining room steps from the large living room featuring a beautiful fireplace, the kitchen offer two Thermador wall ovens, Thermador gas Stove, Amanda refrigerator, Adjacent to the kitchen is a half bath and laundry. Don't miss seeing this beautiful house!

Listed by Peggy Otis of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

28 Gershon Way Winchester MA 01890

Winchester, MA28 Gershon Way, Unit 28

Price$1,690,000

Est. Mortgage: $/month

Open House

MLS Number 72857591

  • Condo or Co-op
  • Next Open House: Mon 07/26 11:30 am. to 3:00 pm.
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,980

2021 Winner for BEST NEW 55+ COMMUNITY IN THE UNITED STATES. ONLY 2 HOMES REMAIN out of 29! Imagine luxurious finishes throughout: 10'+ ceilings, hardwood floors and plenty of natural light. This open concept plan has a 1st floor master suite with oversized walk-in closets and a great bathroom. The kitchen is adorned with ceiling height cabinets, Quartz countertops & island, a spacious pantry + top of the line SS appliance package. The dining room features a beautiful coffered ceiling. Just beyond, the room opens up to a 22' ceiling in the dramatic living room featuring a floor to ceiling fireplace. Abutting the covered porch, a wall of windows pours sunlight into this home. The 1st floor flex room can be a home office, a library or studio for your beloved hobbies. 1st floor also features a powder rm and laundry. Upstairs you'll find 2 additional spacious EN SUITE bedrooms and a bright open loft. 2 Car garage with electric car charging station.*SALES CENTER OPEN DAILY 11-4

Listed by The Marrocco Group of Coldwell Banker Realty - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

158 Cambridge Street Winchester MA 01890

Winchester, MA158 Cambridge Street

Price$1,499,000

Est. Mortgage: $/month

MLS Number 72864119

  • Single Family Detached
  • Bathroom 5
  • Rooms 12
  • Bedrooms 5
  • Acreage 0.26

Large Single Family that was auctioned recently. Seller is looking for a cash buyer to sell the memorandum of sale to. Property delivered in "as is" condition and not subject to vacancy or mortgage contingency in the sale. Lots of equity left of the table on this one. Only serious buyers inquire please. Offers due 7/17/21. Seller reserves the right to accept an offer prior

Listed by Arthur Deych of Red Tree Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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

49 Florence Street Winchester MA 01890

Winchester, MA49 Florence Street

Price$1,499,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72868153

  • Single Family Detached
  • Bathroom 3
  • Rooms 8
  • Bedrooms 4
  • Acreage 0.23

This thoughtfully designed home is a lovely, warm and truly inviting space. It is nicely situated on a corner lot in a great location and short walk to the downtown area. The floor plan was designed to allow for an abundance of natural light throughout. The house was renovated and expanded within the last year and has all new hvac, electrical, plumbing, insulation, windows, flooring, painting, etc. There is an absolutely perfect balance of interior and exterior living space. The first floor includes-living room, dining room, kitchen, half bath, mudroom and fireplaced living room. The second floor-3 bedrooms, 2 baths, a reading nook, and laundry. The third floor has an open area and 4th bedroom.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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.