Winchester Single Family Homes

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. You might also be interested in Medford MA single family homes or Lexington MA single family homes.

Tour Single Family Homes in Winchester MA

View the frequently updated Winchester MA real estate listings below. Contact Sweeney & O'Connell Real Estate or call 781.643.7478 for a tour of single family homes in Winchester MA.

9 Grove Street, Winchester, MA

Price$4,599,000

Est. Mortgage: $/month

MLS Number 72254524

  • Single Family
  • Bathroom 8
  • Full Bath 6
  • Bedrooms 8
  • Year Built 2017

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 RE/MAX Leading Edge

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Sweeney and O'Connell Real Estate
1189 Massachusetts Avenue
Arlington MA, 02476
Office: 781-643-7478

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* 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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14 St Thomasmore Drive, Winchester, MA

Price$3,199,000

Est. Mortgage: $/month

MLS Number 72262053

  • Single Family
  • Bathroom 7
  • Full Bath 6
  • Bedrooms 5
  • Year Built 2018

NEW CONSTRUCTION BY LOCAL MASTER BUILDER! The design of this spectacular home with the integrated floor plan that every modern, savvy buyer seeks truly is a masterpiece. Featuring 3 floors of finished living with volume control surround sound throughout each room. Within the 3-year old Vinson Owen school district. Located a short drive to downtown, where you'll find plentiful coffee shops, boutiques, restaurants, taverns & salons. The commuter rail with 2 Winchester locations is a short 15-20 ride to Boston's North Station. Do not miss out on this opportunity to own a true gem. Become a part of the Winchester community and experience all it has to offer!

Listed by Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

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Sweeney and O'Connell Real Estate
1189 Massachusetts Avenue
Arlington MA, 02476
Office: 781-643-7478

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* 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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10 Ledgewood Road, Winchester, MA

Price$2,995,000

Est. Mortgage: $/month

MLS Number 72198378

  • Single Family
  • Bathroom 7
  • Full Bath 4
  • Bedrooms 6
  • Year Built 2004

This grand estate is nestled into Winchester's most prestigious neighborhood, Ledgewood Estates, with beautifully wooded surroundings and rolling hills.This private compound has a large wooded backyard with a gunite pool, large outdoor mahogany deck and patio ideal for outdoor entertaining. Seldom does such a magnificent estate come on the market with such privacy and beauty. This estate lies 9 miles from downtown Boston or a short stroll to the commuter rail. This premier property has access to Fells reservation and is minutes away from the charming center of town and highly ranked schools.This exquisite residence features floor to ceiling French pella windows, ten foot ceilings, chunky crown moldings, 3 fireplaces, an enormous state of the art chef's kitchen, oversized island ideal for entertaining, large breakfast nook, custom white cabinets, stadium seating media room,3 car garage, screen porch.Custom designed with a sweeping open floor plan by award winning architect, Frank Olivia

Listed by Denise Petitti of RE/MAX Home Team

{$agent->Name}

Sweeney and O'Connell Real Estate
1189 Massachusetts Avenue
Arlington MA, 02476
Office: 781-643-7478

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* 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$2,950,000

Est. Mortgage: $/month

MLS Number 72166793

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

Decorative wrought iron gates open to a carriage driveway and reveal the spectacular mature gardens that create the estate setting for this Colonial Revival masterpiece. Set upon Myopia Hill, among homes of similar architectural distinction, it is difficult to imagine that such privacy can be available so close to the town of Winchester and within striking distance of the city of Boston. 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. This home is resplendent in architectural detail, both inside and out. 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.

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

{$agent->Name}

Sweeney and O'Connell Real Estate
1189 Massachusetts Avenue
Arlington MA, 02476
Office: 781-643-7478

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* 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 Aquinas Path, Winchester, MA

Price$2,879,000

Est. Mortgage: $/month

MLS Number 72240645

  • Single Family
  • Bathroom 7
  • Full Bath 6
  • Bedrooms 5
  • Year Built 2017

WELCOME TO AQUINAS PATH! HOME TO WINCHESTER'S NEWEST LUXURY DEVELOPMENT! ALMOST SOLD OUT! The ultimate in luxury living conveniently located 7 miles North of Boston. New construction by local master builder. The design of this spectacular home with the integrated floor plan that every savvy buyer seeks is truly a work of art. Three floors of finished living with volume control surround sound in every room. The kitchen-family room open concept, with oversized sliders to a stone patio, is the ultimate space for entertaining large crowds. Not 1, but 2 butler's pantries, and a second Cape Cod style covered Blue Stone patio, the only one in the neighborhood. The elegant master suite feels like a boutique hotel featuring a spacious fire placed sitting room with custom built-ins, a gorgeous Marble bathroom and, ladies...a to-die-for walk in closet! The lower level is home to a state of the art movie theatre and home gym with mirrored walls. THIS HOUSE IS A "10"! COME AND SEE FOR YOURSELF!

Listed by Monte Marrocco of Coldwell Banker Residential Brokerage - Winchester

{$agent->Name}

Sweeney and O'Connell Real Estate
1189 Massachusetts Avenue
Arlington MA, 02476
Office: 781-643-7478

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* 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 Saint Thomasmore Drive, Winchester, MA

MLS Number 72223149

  • Single Family
  • Bathroom 7
  • Full Bath 6
  • Bedrooms 5
  • Year Built 2017

Architecturally crafted Colonial located in one of Winchester’s premier locations! This magnificent 7,100+ sqft home with 3-car garage Features 10’ ceilings, an elegant formal dining room with built-ins and butler’s pantry, versatile first floor study with full bath, great room with gas fireplace and incredible millwork including expertly sited built-ins and coffered ceilings. Sunfilled kitchen boasts high end cabinet-fronted appliances and stunning cabinetry with quartzite countertops. Second floor offers 9’ ceilings, en-suite bedroom, Jack & Jill bedrooms, and a breathtaking master suite with a gas fireplace, His & Hers walk-in closets featuring a makeup vanity, custom shelving and plenty of storage. The spa-like master bath boasts heated marble floors, free standing jetted tub & large tiled shower. Third floor offers additional bedroom and full bath. Step outside of this cedar shingled home onto the deck overlooking the built-in grill and stone fire pit. Welcome home!

Listed by Marissa Waite of Barrett Sotheby's International Realty

{$agent->Name}

Sweeney and O'Connell Real Estate
1189 Massachusetts Avenue
Arlington MA, 02476
Office: 781-643-7478

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* 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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366 Main Street, Winchester, MA

Price$2,749,000

Est. Mortgage: $/month

MLS Number 72244192

  • Single Family
  • Bathroom 6
  • Full Bath 5
  • Bedrooms 5
  • Year Built 1853

Let us introduce to you 366 Main Street. Once described by Boston Magazine as an "Unassuming Palace". Originally built in 1853, this historic Winchester property has been brought back to life by a premier local developer and is anxiously awaiting its next loving owner. Enriched with period detail that cannot be replicated today, this 14 room mansion is located just 7 houses from Winchester Center. With stunning landscaped grounds, stately original exterior detail, and detached 4 car garage, you can truly live like royalty here. Do you love soaring ceilings, ornate woodwork and adorned mantels? How about an oversized designer kitchen? Or a master suite that would rival any 5-star accommodation? The flawless blend of new and old world design is possible, and this is proof! With 4 levels of finished space this home will wow you at every turn. 5 bedrooms in total including 2 en-suites, and the spectacular master with custom closets and marble drenched bathroom. Come tour this beauty today!

Listed by Philip J. Vita of RE/MAX Leading Edge

{$agent->Name}

Sweeney and O'Connell Real Estate
1189 Massachusetts Avenue
Arlington MA, 02476
Office: 781-643-7478

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* 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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47 WAINWRIGHT Road, Winchester, MA

Price$2,579,000

Est. Mortgage: $/month

MLS Number 72224619

  • Single Family
  • Bathroom 7
  • Full Bath 5
  • Bedrooms 5
  • Year Built 2007

GRACIOUS, CUSTOM RESIDENCE sited on a private lot, in a very desirable location. Quality construction, dramatic architecture, elegant details and lavish appointments. A perfect blend of formal space and comfort. The gourmet kitchen features a breakfast room that leads to an outdoor patio, perfect for entertaining family and friends. The Master Bedroom features a spa- inspired bath and walk in closets. 3 additional bedrooms with en-suite baths and walk in closets complete this lovely home. This is a unique buying opportunity for this type of quality that is only found in custom built homes. Here is your chance to make it yours!

Listed by Dorothea Feffer of Coldwell Banker Residential Brokerage - Winchester

{$agent->Name}

Sweeney and O'Connell Real Estate
1189 Massachusetts Avenue
Arlington MA, 02476
Office: 781-643-7478

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* 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

184 Ridge Street, Winchester, MA

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72263106

  • Single Family
  • Bathroom 5
  • Full Bath 4
  • Bedrooms 4
  • Year Built 2017

Perched atop the West Side Hill, on almost 1 acre, this east facing, sprawling new construction 4Beds 4.5Bath home will exceed your expectations! First floor features huge 30' kitchen with Thermador appliances, 10' center island, custom cabinets, dining area, pantry, mudroom, heated attached 3 car garage, year round sunroom overlooking sprawling "football field" sized back yard, family room off kitchen with natural stone fireplace, office, formal living w/ FP, dining room, butlers pantry, and a dramatic stairway to the second floor. Master is unlike anything you've seen..enter into a sitting room with fireplace, ballroom sized bedroom, lavish master bath with radiant heat floor, custom cabinetry, soaking tub and oversized shower with built in seat. 3 Add'l bedrooms with en-suite baths. Lower level w/ full windows & slider can easily be customized with another full bath/media room/gym;you design.. builder will create for you! Don't miss this spectacular home complete w/ HEATED DRIVEWAY!

Listed by Kim Covino of RE/MAX Leading Edge

{$agent->Name}

Sweeney and O'Connell Real Estate
1189 Massachusetts Avenue
Arlington MA, 02476
Office: 781-643-7478

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* 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

7 Ledgewood Road, Winchester, MA

MLS Number 72216690

  • Single Family
  • Bathroom 4
  • Full Bath 3
  • Bedrooms 4
  • Year Built 1946

Custom Shingle style estate in one of Winchester's most private areas; near town ctr, schools, train, Fells. Beautifully set back on rare acreage ideal for outdoor living Property incl 10% ownership half acre lot with tennis court. Pella Energy Star windows/drs, Wood Mode cherry built-ins, radiant heat wood flrs thru-out Gourmet kitchen w/quartz, 10 foot island, top line SS appliances, gas FP, Butler's pantry w/wine cooler. 1st & 2nd flr master suites & potential for 5th bedroom. Walk-up attic. Perfect family home, also amazing for entertaining for small or large gatherings.

Listed by Peggy Otis of Coldwell Banker Residential Brokerage - Winchester

{$agent->Name}

Sweeney and O'Connell Real Estate
1189 Massachusetts Avenue
Arlington MA, 02476
Office: 781-643-7478

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.94% last updated on Jul 13, 2017
* 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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