Winchester Real Estate

Just 15 minutes northwest of Boston is the beautiful town of Winchester, MA. When your kids are on summer vacation from Winchester's top-ranked public school system, have them spend time sailing at the Winchester Boat Club, keeping fit at the Winchester Swim and Tennis Club, or golfing at the Country Club. A quick trip on the Communter Rail's Purple Line will drop you right at the Fleet Center in central Boston, perfect for easy commuting to work or for an evening out. Don't miss out on D'Agostino's Deli, a famous local spot for subs, sandwiches, party trays, and more delicious deli wonders.

And Winchester real estate doesn't disappoint: find many new construction single-family homes, historic estates, luxurious condos, and more.

View currently listed real estate in Winchester below and contact Century 21 Advance Realty with any questions or to schedule a tour. You can also register with our site to save your favorite properties and receive notifications via email when a new listing matches your preferred criteria. 

11 Lorena Road Winchester MA 01890

Winchester, MA11 Lorena Road

Price$2,945,000

Est. Mortgage: $/month

MLS Number 72628997

  • Single Family
  • Garage 2
  • Parking Spaces 5
  • Total Parking Spaces 7
  • MLS Status Active

Steeped in history, 11 Lorena Road features 7,549 square feet of living space & is a quintessential New England home in both setting & style. Originally designed by renowned architect Miles Standish, a 1960s addition by Richard Wills of the elite Royal Barry Wills architecture firm-featured in Life Magazine in both 1938 & 1946 for his classic Cape Cod & Colonial home designs-added an early American pub w/ beautiful pine-paneled walls, full bar, fireplace & abundant seating as well as a country living room. In 1999 Richard's son, also of RBW, added an updated kitchen, family room & second floor bedrooms. All of this is set on 1.5+ acres of terraced land w/ patio spaces, embedded mill stones & spectacular gardens with a number of rare & unusual plantings including a certified Dawn Redwood that is one of the oldest in the US & believed to be from the original batch of seeds brought to the US from China by the Arnold Arboretum. Additional details abound in this unique, special home!

Listed by Anne Spry and Lesley Smith of Waterfield Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 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 Wagon Wheel Road Winchester MA 01890

Winchester, MA5 Wagon Wheel Road

Price$2,670,000

Est. Mortgage: $/month

MLS Number 72625592

  • Single Family
  • Garage 3
  • Parking Spaces 12
  • Total Parking Spaces 15
  • MLS Status Active

A Must Have Is This Majestic Brick COLONIAL Home With A Heated Three Car Garage Attached To The House With Plenty of Parking For Guests Also. On Over An Acre of Beautiful Professionally Landscaped Flower Beds and Green Grass. it includes 7,097 Square Feet Of Living Space, Huge Heated Pool, Year Round 10 Person Spa. 14 Rooms, 6 Bedrooms, 6 Full Bathrooms, Finished Basement. When you Enter the New Elegant Double Front Door Will Welcome You Featuring A Family Room With A Fireplace, Formal Living Room, Dining Room, Office, And The Gorgeous Kitchen on the First Floor. To The Second Floor You Have A Private Master Bedroom Area With a Fireplace, Heated Tile Bathroom Floor , A Large Walk In Closet and A Reading Room. Three Large Bedrooms Complete the Second Floor Including Walk In Closets in Each One. The Third Floor Offers A Great Living Area For Visitors And An Additional Master Suite. Built in 2015 it still Looks Like Brand New. A Must See And Buy for the Family.

Listed by J D J Elite Team, Deborah Byrne, Jack Lister and Joanne Vanstry of Berkshire Hathaway HomeServices Verani Realty

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 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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9 Ginn Road Winchester MA 01890

Winchester, MA9 Ginn Road

Price$2,499,000

Est. Mortgage: $/month

MLS Number 72633034

  • Single Family
  • Garage 2
  • Parking Spaces 6
  • Total Parking Spaces 8
  • MLS Status Active

Stunning Craftsman Colonial with a dreamy back yard in top neighborhood! Beautifully situated on one of the largest lots in the area, you will be proud to call this spectacular house your home! Gorgeous welcoming front porch with breathtaking entry, featuring a 180 gallon salt water fish tank, sleek designer kitchen w/ custom Bamboo cabinets, Lutron auto shades & LR w/stone/gas fireplace. Spacious 1st floor Master suite w/ spa like bath, soaking tub, walk in closet & sitting area w/ high ceilings & french doors to patio overlooking amazing back yard; outdoor entertaining at its finest! Offering a full kitchen with sink, fridge, built in gas grill w/ dining/ bar, TV and sun-setter auto.awning! Custom built w/top of the line everything, this home is a work of art with beautiful finishes and custom details throughout. 4/5 large bedrooms each w/ private baths,1st floor office, mudroom with lockers leads to 2 car garage, plus over 1200 sf add'l basement space avail for future game/media/gym

Listed by Kim Covino of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 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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39 Myopia Road Winchester MA 01890

Winchester, MA39 Myopia Road

Price$2,349,000

Est. Mortgage: $/month

MLS Number 72574074

  • Single Family
  • Garage 2
  • Parking Spaces 10
  • Total Parking Spaces 12
  • MLS Status Active

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

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 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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43 Grove Street Winchester MA 01890

Winchester, MA43 Grove Street

Price$2,199,000

Est. Mortgage: $/month

MLS Number 72629238

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Active

NEW CONSTRUCTION! This exquisite 5 beds 4.5 bth colonial features open floor concept for today's family living! Thoughtfully designed with a high-end finishes & details, this homes offers an oversized 2-car garage, direct entry into mudroom, gourmet kitchen w/ island & high end appliances, FR with FP & direct exterior access , formal LR & DR with crown moldings & wainscoting. Second floor features include master suite w/ 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. Great rear yard w/deck & sliders from kitchen. The lower level bonus space features spacious family room, full bath &-plenty of space for gym. Looking to build an in-ground pool? This home has the perfect setting and yard to accommodate all your backyard needs. Don't miss this opportunity to customize some interior finishes!

Listed by Kim Covino of Leading Edge Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 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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54 Wedgemere Avenue Winchester MA 01890

Winchester, MA54 Wedgemere Avenue

Price$2,199,000

Est. Mortgage: $/month

MLS Number 72638671

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Active

Enjoy life in this gorgeous Wedgemere Avenue home with spectacular backyard retreat! Updated throughout with custom high end finishes, wonderful chefs kitchen with Sub Zero/ Wolf appliances, sunny breakfast/dining area with a wall of windows overlooking expansive back yard featuring gorgeous patio & maintenance free heated POOL with in- floor cleaning system and auto cover! Inviting covered rear porch / outdoor living room complete with flat screen TV just steps from pool and kitchen. Enormous family room with gas fireplace, built in bookshelves & great storage. Stylish formal dining room with custom wainscoting, window buffet & china cabinet, front to back LR w/ fplc; Grand rooms, detailed moldings, new windows, new baths, great master suite with 2 walk in closets, spa like bath with oversized shower and soaking tub. Full third floor with 3 rooms and full bath, updated heating system, central air, new roof. 2 car detached garage with office above completes this great home!

Listed by Kim Covino of Leading Edge Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 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 Fox Hunt Lane Winchester MA 01890

Winchester, MA5 Fox Hunt Lane

Price$2,050,000

Est. Mortgage: $/month

MLS Number 72633001

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Active

Understated and unique luxury. This traditional brick colonial opens into an interior of simple, contemporary beauty. Situated on 1.2 acres that border the 13th fairway of the Winchester Country Club, the home's 300-foot elevation affords sweeping views across the Mystic Lake and into East Boston. A large deck and patio invite outside entertaining. Inside, the home mixes traditional and contemporary elements: an expansive living room with custom Butternut woodwork and vaulted ceiling; a kitchen/family room with a gas fireplace; a TV and billiards room; a master bedroom suite with a fireplace and attached office/dressing room. The second floor features two ensuite bedrooms, plus options for additional bedrooms. The walk-out lower level includes an indoor pool, greenhouse, and a fourth bedroom with a separate entrance, bathroom, and sauna.

Listed by Cynthia Houle and Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 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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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
  • Total Parking Spaces 6
  • MLS Status Active

Beautiful NEW CONSTRUCTION Home East Side of Winchester! Move right into 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

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$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 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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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
  • Total Parking Spaces 6
  • Year Built 2020

This beautiful new construction, three level Colonial home is a must see, ready for a 4 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: 3.33% last updated on Apr 2, 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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Lot 2 Forest Street Winchester MA 01890

MLS Number 72628681

  • Single Family
  • Garage 2
  • Parking Spaces 4
  • Total Parking Spaces 6
  • MLS Status Active

~New Construction in Winchester~ Under Construction for occupancy early summer. This 10 room, 5 bedroom home is the 1st of 3 brand new homes by prominent local builder. Thoughtfully designed with an open yet traditional feel. The 1st floor features open concept kitchen and family room w/fireplace, formal dining room, gorgeous kitchen with quartz counters & center island, 1/2 bath & mud room. The 2nd flr features 4 bedrooms all with walk-in closets, and a large laundry room with sink. The master bedroom has a luxurious bath with soaking tub, separate fully tiled walk-in shower, double sink vanity and private water closet . The 3rd floor has a bonus room plus a 5th bedroom w/full bath perfect for au-pair, in-law or teen suite. This home is perfect for the family looking for convenient access to the Middlesex Fells, Rt 93 and in the popular Muraco School District. Because this is New Construction and unoccupied, showings ARE allowed and we are adhering to Covid-19 showing guidelines.

Listed by The Synergy Group and Paul Cirignano of Leading Edge Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 2, 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.