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. 

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9 Grove Street, Winchester, MA

Price$4,499,000

Est. Mortgage: $/month

MLS Number 72254524

  • Single Family
  • Parking Spaces 10
  • Year Built 2017
  • Full Bath 6
  • Bathroom 8

True elegance so rarely experienced, this majestic historic home has been completely renovated and restored to its original grandeur, blending exquisite period details with luxurious modern amenities. Quality throughout with designer touches and high-end finish work, this 8bed/8bath 10,000SF+ home has been tastefully redesigned for today's lifestyle. This home features gourmet eat-in kitchen with Sub-Zero/Wolf appliances, french doors leading to deck, living room w/ coffered ceilings & FP, mahogany library & DR. Second floor boasts high ceilings, FP Master with spa bath & walk-in closet, en-suite beds and laundry with folding area. 3rd floor great for au-pair w/ 4 beds, full bath & add'l laundry area. Lower level features media room, kitchen/wet bar, game room, wine cellar, mirrored gym equipped w/ rubber flooring and spa bath w/ steam/sauna/rain shower. All new plumbing & heating, "Smarthouse" technology, 400amp electrical, surround sound, intercom system, 3/4 car garage. A must see!

Listed by Kim Covino of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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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6 Robinson Park, Winchester, MA

Price$3,099,000

Est. Mortgage: $/month

MLS Number 72387575

  • Single Family
  • Parking Spaces 4
  • Year Built 1949
  • Full Bath 4
  • Bathroom 5

STUNNING WATERFRONT PROPERTY ON UPPER MYSTIC LAKE! Meticulously maintained home with mature plantings and private dock. Thoughtfully designed for today's savvy buyer. Featuring a large fireplaced family room with cathedral ceilings & an oversized kitchen with a top of the line SS appliance package & granite counters, perfect for entertaining. The formal dining & living room complete the 1st floor. Upstairs houses a large master suite with walk in closet, full bath with shower and separate Jacuzzi. 3 other bedrooms, 2 full baths and laundry finish the 2nd floor. The upper level is just waiting for an inspiring artist to set up a proper studio! Plenty of natural light and dramatic water views from almost every room! Extremely peaceful and quiet location within a short drive to downtown, where you'll find plentiful boutiques, coffee shops, restaurants and the commuter rail to North Station. Within the Ambrose Elementary school, easy access to major highways and only 7 miles to Boston.

Listed by The Marrocco Group and Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

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$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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 Wagon Wheel Road, Winchester, MA

Price$2,900,000

Est. Mortgage: $/month

MLS Number 72402008

  • Single Family
  • Parking Spaces 10
  • Year Built 2015
  • Full Bath 5
  • Bathroom 6

This newly constructed home (2015), one of the largest in Winchester, sits on over an acre of land and boasts over 7,000 square feet of living space. There are 14 rooms, which include 5 bedrooms, as well as 6 bathrooms, and a heated three-car garage and finished basement. An outdoor entertaining area awaits, with an oversized, fence-in yard, resort style patio/deck, pool and hot tub. Upon entry to this home you'll be welcomed by a bright living space with a formal living room, dining room, office, and a massive open kitchen/living area with a gas fireplace. The second floor hosts the master suite, complete with a fireplace, bath and walk-in closet, as well as a nursery/library. Three additional generously sized bedrooms and a laundry room complete this level. The third floor offers a second full master suite. The finished basement with a full bathroom provides a versatile space for a gym, billiards room, theatre, or combination thereof and offers direct access to the pool area.

Listed by Travis Barfield of Compass

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$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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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54 Myopia Road, Winchester, MA

Price$2,850,000

Est. Mortgage: $/month

MLS Number 72323335

  • Single Family
  • Parking Spaces 6
  • Year Built 2000
  • Full Bath 5
  • Bathroom 7

This Colonial Revival masterpiece is a testament to one of MF Reynolds' finest renovation and expansion projects. Offering a quality of construction and materials exceeding that typically found in new builds, the floor plan was designed with a principal goal - to be first and foremost a family home designed around a central core dedicated to a large open plan kitchen and a generously proportioned family room. To the rear, a large patio overlooks lawns for children's activities and a woodland wonderland for exploration. Set upon Myopia Hill, in an estate setting of spectacular mature gardens, the property is surrounded by homes of similar architectural distinction. This family-friendly neighborhood provides ease of access to all Winchester offers: fine schools, children's activities and clubs, boat club, beach, golf course, and the community's Wright Locke Farm, to name a few. It is difficult to imagine that such privacy can be available within striking distance of Boston.

Listed by Jonathan Radford of Coldwell Banker Residential Brokerage - Boston - Newbury St.

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$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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 Central Green, Winchester, MA

Price$2,850,000

Est. Mortgage: $/month

MLS Number 72339037

  • Single Family
  • Parking Spaces 4
  • Village Rangeley
  • Year Built 1930
  • Full Bath 4

Georgian Colonial home short stroll to Winchester Center, private setting, close to parks and public schools. The home was taken down to the studs and rebuilt in 2008, the home owners moved back to their home in 2009. This home was renovated with the modern family in mind. Enjoy two private patios and gardens perfect for relaxing or entertaining. The gourmet kitchen offers a spacious island, two ovens plus warming oven, five burner gas stove, all top of the line appliances , plus area for casual dining and adjacent family room with a gas fireplace overlooking the pristine back yard. The home offers five spacious corner bedrooms, Master bedroom features a wood burning fireplace, two walk-in closets and master bathroom. In the basement there is a large room that was once a handball court, spacious enough for a media room. This home offers exquisite detail throughout, one of Winchester's Finest location. See the reasonable heating/cooling costs in attch.

Listed by Peggy Otis of Coldwell Banker Residential Brokerage - Winchester

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$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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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31 Swan Road, Winchester, MA

Price$2,399,999

Est. Mortgage: $/month

MLS Number 72410499

  • Single Family
  • Parking Spaces 10
  • Year Built 1929
  • Full Bath 3
  • Bathroom 5

What does it mean to have a Swan Road address? It means you've arrived! Give yourself the gift of owning 31 Swan Road. A stately Tudor style home with magnificent grounds, situated on one of the finest roads that Winchester has to offer. The stunning brick exterior, adorned with slate roof, will impress you from moment one. As you enter, the beautiful foyer will leave you breathless. The sunken living room with Bath Stone fireplace and hand crafted wood walls is something straight out of a magazine. Enjoy the opulence and grandeur of a time gone by, seamlessly combined with a sensible layout and amenities of today such as a renovated kitchen with Wolf, Viking, and SubZero appliances. The second level is home to four bedrooms, and 3 full baths, including the master suite drenched with natural light, thanks in part to the homes South facing direction. Should you venture off these park-like grounds you'll find yourself within walking distance to both Winchester Country Club and Boat Club.

Listed by Philip J. Vita of Leading Edge Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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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56 Lorena Road, Winchester, MA

Price$2,300,000

Est. Mortgage: $/month

MLS Number 72407613

  • Single Family
  • Parking Spaces 4
  • Year Built 2004
  • Full Bath 4
  • Bathroom 5

2017 custom renovation by Refined Renovations, this house is perfect for both work & play. A spacious, open concept 1st floor features a stunning, brand new true chefs kitchen w/2 islands & sub zero fridge, home office, mudroom, living room w/rock face fireplace & window seats. Formal dining room w/all new, butler's pantry. Kids and pets can play in the huge, private, fenced in backyard while the grownups relax on the deck. 2nd floor includes an all new laundry room w/sink & storage, MBR w/walk in closet, master bath has steam shower & soaking tub. 3 more good sized bedrooms & 2 baths complete this level. A finished 3rd floor includes skylights and storage.1100sf+ finished basement w/wet-bar, fireplace, exercise room & full bath lead out to a professionally landscaped yard featuring /hot tub, koi pond & waterfall, fire-pit and lighting. Less than a mile from town & 2 commuter stops. The Fells is around the corner and easy access to hwy & Boston.

Listed by Adam Shamus of Keller Williams Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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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4 Ravine Road, Winchester, MA

Price$2,299,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72348070

  • Single Family
  • Parking Spaces 6
  • Year Built 2001
  • Full Bath 5
  • Bathroom 7

UNBEATABLE LOCATION, SITUATED IN THE HEART OF DOWNTOWN WINCHESTER!!! Enter into the dramatic 2-story foyer featuring one of three Swarovski Crystal Chandeliers! Host a dinner party in the Chefs kitchen boasting granite counters, a 48"SUBZERO refrigerator, a 60"gas WOLF range & 2 BOSCH dishwashers. Step out into the pristine garden with built in BBQ and outdoor pizza oven! The dining room has built-in china cabinets, a fireplace and is surrounded with beautiful windows. 5 bed suites, each w/private bath. A Master bed fit for a King & Queen! Seamless flow throughout provides unparalleled luxury living on 4 levels. Gorgeous media room on lower level, featuring a home theatre and bar. Newly finished hardwood floors , and many rooms recently painted. Walk to the farmer's market on the common and explore Winchester's boutiques, restaurants & coffee shops or take the commuter rail to North Station for a day in the city. Within the Ambrose school district and 7 miles North of Boston.

Listed by The Marrocco Group and Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

$
$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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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6 Thornton Road, Winchester, MA

Price$2,199,000

Est. Mortgage: $/month

Open House

MLS Number 72406167

  • Single Family
  • Next Open House: Sat 20th 11:00 am - 12:30 pm
  • Parking Spaces 4
  • Year Built 2013
  • Full Bath 3

Prepare to be impressed by this well crafted 5 year old 14 room unconventional colonial with just under 7000 sqft of luxury living space, 5 bedrooms, & 3 1/2 baths. Large gourmet kitchen w/breakfast area, 2 tiered island, stainless steel appliances w/adjoining family room with fireplace, cathedral ceiling & glass sliding door to 2nd story deck. Large living room with fireplace & built-in bookcases, dining room with crown molding, wainscoting, chair rail & bay window, an office completes the first floor. The 2nd floor consists of spacious master bedroom with walk-in closet & spa like bath, 3 bedrooms, main bath, laundry room & sitting area. On the 3rd floor you will find a play room & 5th bedroom with en-suite & large closet. The finished lower level consists of large home gym & game room that exits to granite patio & expansive rear yard. A 2 car garage & dry storage under deck. A convenient Westside location in the VO school district close to parks, shopping, & public transportation.

Listed by Errico Team of Waterfield Sotheby's International Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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 Yale Street, Winchester, MA

Price$2,039,000

Est. Mortgage: $/month

Open House

MLS Number 72374672

  • Single Family
  • Next Open House: Sat 20th 11:00 am - 12:30 pm
  • Parking Spaces 10
  • Year Built 1906
  • Full Bath 3

Renovated 11 room Victorian home with inviting front porch offering the charm and character of historic Winchester, with all the amenities of today. This grand home was renovated in 2013 including roof, windows, heat, a/c, kitchen, baths, plumbing, electrical. Move right in and enjoy this great home with granite/ stainless kitchen w/white cabinetry, separate dining area, gas 2 sided FP & sunlit family room. Exterior sliders off the family room lead to a beautifully manicured level lot w/mature trees offering an abundance of privacy. Spacious brick patio great for outdoor entertaining. Welcoming entry foyer with original staircase leads to 2nd level offering 4 beds, 2 full baths & laundry room. 3rd level offers 3 sun drenched BR's & full bath. Master bed suite w/marble bathroom, Oversized steam shower w/body sprays/bench/surround sound! Radiant heat flooring & towel warmer. Custom built oversized 2 car garage w/ room above~one of the nicest yards in the flats!! Ambrose Elementary school

Listed by Kim Covino of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.9% last updated on Oct 11, 2018
* 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

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