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 Niles Lane Winchester MA 01890

Winchester, MA11 Niles Lane

Price$3,499,000

Est. Mortgage: $/month

MLS Number 72916261

  • Single Family Detached
  • Bathroom 6
  • Rooms 12
  • Bedrooms 5
  • Acreage 0.38

It's an end-of-season debut, the nicest renovation that Winchester has produced all year! If you've grown tired of cookie-cutter "new" construction, this is the home for you. PRIME location, one of the most sought-after streets in town. Quiet and beautiful with lake views plus your very own deeded parcel on the lake that provides you full water access. The interior stuns with a jaw-dropping layout & build-out, with quality well beyond the typical. You'll get giddy when you see the biggest kitchen/family room imaginable, complete with a wet bar, a second dishwasher & a beverage center. Light floods this house from every angle, it's spectacular. Entertain in the formal dining room and living room, flanked by a wall of glass leading to the patio and outside grilling area. Two primary bedroom suites offer options: one is massive with front and back balconies & lake views, plus dual walk-in closets. The other has a fabulous sitting room/study attached. Too much to mention, come see it!

Listed by Nancy S. Pallotta of Leading Edge Real Estate

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 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.

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32 Ledgewood Road Winchester MA 01890

Winchester, MA32 Ledgewood Road

Price$2,799,000

Est. Mortgage: $/month

MLS Number 72921941

  • Single Family Detached
  • Bathroom 4
  • Rooms 10
  • Bedrooms 5
  • Acreage 0.3

NEW CONSTRUCTION!! Must see this gorgeous 4/5 bedroom home with thoughtful design & high end finishes! This luxurious home is spacious and inviting, offering a grand open floor plan ideal for entertaining and modern day family living. The kitchen features an oversized island with seating/ double thick quartz countertops, high-end thermador professional appliances, wine bar w/ fridge, breakfast nook/morning dining area. Off the kitchen is a spacious family room with gas fireplace and direct exterior access w/ sliders leading out to the large deck & private rear yard. The first floor also has a formal dining room and 5th bed OR home office with 3/4 bath. The second level master suite is a DREAM, offering a 2 room suite; bedroom with separate sitting room, dual walk-in closets, lavish bath with tiled shower/glass enclosure, double vanities & soaking tub! Three additional beds incl. junior suite w/ bath, full hall bath and a laundry room finish this level.oversized 2 car garage & mudroom.

Listed by Kim Covino of Compass

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 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.

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119 Forest Street Winchester MA 01890

Winchester, MA119 Forest Street

Price$2,299,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72893561

  • Single Family Detached
  • Village Fells area
  • Bathroom 6
  • Rooms 12
  • Bedrooms 5

Just completed! Must see this fabulous +/- 6000 sf Colonial farmhouse! This newly constructed 5 bed, 4 full, 2 half bath home by premiere local builder is one of a kind & offers space & style that will impress! With the frontage on Bell Road, the location offers an abundance of privacy and side street access. From the moment you enter you will feel the quality & appreciate the beautiful craftsmanship; features include a stunning kitchen w/quartz counters, wide plank oak flooring, oversized island, Viking appliances w/ 48" fridge, 6 burner gas range along with a wet bar w/wine fridge & walk in pantry! Adjacent family room w/fplc, formal dining room, living room & stunning office w/ walls of windows, Amazing master suite w/ spa like bath, soaking tub & oversized marble shower. 4 additional spacious bedrooms /2 en-suite, 2 car garage w/2 charging outlets, direct entry to mudroom w/ bench, bead board trim & cubbies. Great lower level Media/Game/Home Gym. In wall speakers & smart locks.

Listed by Kim Covino of Compass

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 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.

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15 Vinson Circle Winchester MA 01890

Winchester, MA15 Vinson Circle

Price$1,999,000

Est. Mortgage: $/month

MLS Number 72911440

  • Single Family Detached
  • Bathroom 4
  • Rooms 9
  • Bedrooms 4
  • Acreage 0.98

Private 1 acre lot! Situated on one of the most beautifully manicured & exclusive lots in Winchester, this unique property offers endless opportunities to create your dream home! Dramatic open layout w/ walls of windows, soaring cathedral ceilings, featuring 4+ bedrooms, 3.5 bathrooms & including an attached in-law suite w/ a full bathroom, kitchen / cabinetry, & private exterior access. The updated chefs kitchen includes four ovens, gas stove, a skylight and double sliding glass doors that lead to the back deck overlooking the expansive, spectacular yard.Two extra large sheds in backyard for storage, a gazebo with deck space, and a courtyard with grilling station make this property an entertainers dream. This property is situated in a neighborhood that can support a 3M home; close to Vinson Owen elementary. Build equity and create the home of your dreams with a custom renovation & plenty room for a pool! Builders lined up and available to work directly with buyers!

Listed by Kim Covino of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 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.

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254 Main Winchester MA 01890

Winchester, MA254 Main

Price$1,659,000

Est. Mortgage: $/month

MLS Number 72873085

  • Single Family Detached
  • Village Downtown location
  • Bathroom 3
  • Rooms 10
  • Bedrooms 4

Amazing value!! Stunning and very spacious home! Set on an oversized lot with great rear yard just outside the vibrant town center; this sprawling 10 room, 4 bedroom 2.5 bath home w/ 3 car garage will exceed your expectations! Recently renovated and expanded this great home has the look and feel of a colonial from the exterior yet offers a stunning redesigned open concept kitchen w/ great room addition on the rear w/soaring ceilings, amazing space and contemporary flair! The high end kitchen is the heart of the home with wonderful flow for entertaining, island seating and adjacent wine bar. Great room off kitchen with breathtaking space, vaulted ceilings, double gas fireplaces and sliders to spacious deck overlooking the rear yard. Pantry storage, mudroom & laundry all just off the kitchen. Formal dining, living room w/fplc. & sunroom/family room complete this floor. The second features 4 bedrooms, a grand master w/ vaulted ceilings & private bath plus 3 add'l bedrooms and full bath.

Listed by Kim Covino of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 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.

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314 HIGHLAND Avenue Winchester MA 01890

Winchester, MA314 HIGHLAND Avenue

Price$1,550,000

Est. Mortgage: $/month

MLS Number 72916495

  • Single Family Attached
  • Bedrooms 4
  • Bathroom 4
  • Rooms 11
  • Square Feet 4,372

The grand residence is located in a private setting steps from Winchester Center. Large rooms throughout with multiple primary suites, & a grand 2 story great room that is the heart of this home. Eat-in kitchen with pantry that flows seamlessly to sunroom & 2 tiered decks. The yellow antique yellow-pine bar is a show stopper! Sunny library and cozy family room round out first floor. Large yard for kids & pets with an opportunity for gardening. A lower-level home office with a separate entrance. This is definitely not your average Winchester home but it sure does check all the boxes for the buyer looking for a very special home in a premier location. This residence is a commuter's dream a short distance from I93 (2.3miles). Call this one home!

Listed by Nancy Ciampa McLaughlin of Redfin Corp.

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$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 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.

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384 Washington Street Winchester MA 01890

Winchester, MA384 Washington Street

Price$1,299,000

Est. Mortgage: $/month

MLS Number 72891009

  • Single Family Attached
  • Bathroom 2
  • Rooms 11
  • Bedrooms 5
  • Acreage 0.13

No one strives for ordinary, so why do so with your home purchase? Quite possibly the most unique property offering in Winchester! This home lends itself beautifully to multi-generational or extended families, or those simply looking for some extra space and privacy. 384 Washington Street boasts 5 bedrooms, 2 living rooms, 2 dining rooms, a beautifully renovated kitchen, an additional kitchenette, and 2 full bathrooms. Who doesn't like 2 for the price of 1?! The front farmers porch is a true delight and the perfect place to sit and enjoy a morning cup of coffee. If you stay in your PJs a little longer and prefer more privacy, the fenced in (private) backyard with oversized patio is the perfect option! Located just over a 1/2 mile to Winchester Center. Walk to shops, restaurants, the commuter rail station, and more! Perhaps best of all, this home sits on the corner of Washington Street and Bates Road where the coveted Muraco Elementary School can be found.

Listed by Vita Realty Group and Philip J. Vita of Compass

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$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 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.

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384 Washington Street Winchester MA 01890

MLS Number 72890923

  • Condo or Co-op
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 4,104

No one strives for ordinary, so why do so with your home purchase? Quite possibly the most unique property offering in Winchester! This home lends itself beautifully to multi-generational or extended families, or those simply looking for some extra space and privacy. 384 Washington Street boasts 5 bedrooms, 2 living rooms, 2 dining rooms, a beautifully renovated kitchen, an additional kitchenette, and 2 full bathrooms. Who doesn't like 2 for the price of 1?! The front farmers porch is a true delight and the perfect place to sit and enjoy a morning cup of coffee. If you stay in your PJs a little longer and prefer more privacy, the fenced in (private) backyard with oversized patio is the perfect option! Located just over a 1/2 mile to Winchester Center. Walk to shops, restaurants, the commuter rail station, and more! Perhaps best of all, this home sits on the corner of Washington Street and Bates Road where the coveted Muraco Elementary School can be found.

Listed by Vita Realty Group and Philip J. Vita of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 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

17 Wickham Road Winchester MA 01890

Winchester, MA17 Wickham Road

Price$1,150,000

Est. Mortgage: $/month

Active With Contract

MLS Number 72900487

  • Single Family Detached
  • Bedrooms 3
  • Rooms 6
  • Bathroom 3
  • Acreage 0.23

Perfectly located on a quiet street in a highly desired area of Winchester. A custom and well built home perfect for entertaining now awaiting its new owners and the opportunity to update its 4227 sq. ft. of spacious living area to make it their own. Features include 2 fireplaces, large living and dining room, and spacious finished basement including a wine cellar. Only a few miles from Boston, close to major highways and Winchester commuter rail. Come experience everything Winchester has to offer including shops, restaurants, and top rated schools.

Listed by Erin Nolan of Shibilia Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 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.

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40 Elmwood Avenue Winchester MA 01890

MLS Number 72904607

  • Condo or Co-op
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,342
  • Complex Allegro

One of our latest unveilings is unit #2 ... quite possibly one of the best units in the entire building. The ONLY non-penthouse unit boasting (2) garage parking spaces. PLUS it has the LARGEST private patio offered at Allegro! A HUGE BONUS!! Picture yourself strolling Downtown for your morning cup of joe, then over for a quick visit to the farmers market to pick up some fresh items for dinner. Don't feel like cooking? We don't blame you! Out the door you go, AGAIN, to enjoy any one of the fabulous restaurants our town center has to offer. This is how you live when you live Allegro. This elegant brick building boasts units with in-unit laundry and easy one level living. Don't forget about the elevator and heated garage for your car. Condo fee includes trash service, landscaping, snow removal, property maintenance, PLUS HEAT & WATER!

Listed by Vita Realty Group, Michael Askjaer and Philip J. Vita of Compass

$
$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 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.