Real Estate in Winchester, Massachusetts

Winchester is renowned for its fine public school system, beautiful homes and easy access to Boston. Just eight miles northwest of Boston, and close to I93/95, it offers two commuter rail stations as well as bus service to the Wellington T station.  Its charming downtown center with brick sidewalks, lanterns and picturesque ponds is quintessential New England in feel, the perfect place to shop for real estate.

Settled in the early 1600's, the village was first known as Waterfield. The village atmosphere remains alive, fueled by the spirited civic pride of Winchester's residents. The citizens of the town take a deep interest in the management of the town's affairs and in its continued improvement and beautification. Residents enjoy its proximity to the Middlesex Fells and many recreational programs.

Popular events/places

• ENKA Fair (May)
• Annual Town Day (June)
• Griffin Museum
• Winton Club Cabaret
• Halloween Parade/Window Painting
• Jenks Senior Center
• Arthur Griffin Museum
• Winchester Cooperative Theater
• The Middlesex Fells
• Farmer’s Market
• Tree Lighting Ceremony

Recent Press:

• Voted TOP 12 PLACES TO LIVE: BOSTON MAGAZINE 2010.

Check out the Winchester Website

$2,165,000 Virtual Tour 15 Aristotle Dr Winchester, MA 5 Beds, 6 Baths, 6,504 Sq. Ft. 6000+ SF Smart Home! Kitchen w/granite, center island, SS appliances, HW, w/adjoining FR. Formal LR & DR. Mahogany library. Home Office & 2 half baths on 1st fl. 2nd level great room w/cathedral ceiling, gas FP & Surround Sound. Master suite w/vaulted ceiling & walk-in closets. 4 BR's, 2 full BA. Level 3 plumbed & wired. LL w/full bar, weight rm, sauna, gas FP, full BA, ample storage. Panoramic view, 3 car garage, CVAC, AC, AZAC molding, roof w/40 yr warranty, professional landscaping. View Details MLS # 71486021 Schedule a Showing Email a Friend

$2,000,000 2 Lowell Ave Winchester, MA 20,000 Sq. Ft. High end showroom/office space along with open warehouse/manufacturing area. Occupied by home design co and is built out with their first class building design concepts. There is 4,000 sf of showroom space on the first floor and 3,000 sf of office/open work station space above with 13,000 sf of warehouse/manufacturing remaining. The warehouse is split to include a 6,752 sf gym/work out space with separate entrance and bathrooms. The owner will lease/sell anywhere from 6752 sf to entire 20,000 sf View Details MLS # 71519769 Schedule a Showing Email a Friend

$1,999,900 Virtual Tour 11 Davey Lane Winchester, MA 5 Beds, 7 Baths, 5,970 Sq. Ft. PRISTINE AND LUXURIOUS! Custom Built, one owner elegant residence. High quality construction and finishes throughout. Spacious versitile floor plan, completed with timeless elegance and intricate details. Expansive decks. Screened porch and patio are surrounded by manicured grounds. Ideal for indoor and outdoor entertaining. Located on a cul de sac near the Fells. Easy Commute to Boston and Airport. View Details MLS # 71511733 Schedule a Showing Email a Friend

$1,939,900 Virtual Tour 30 ARLINGTON STREET Winchester, MA 5 Beds, 5 Baths, 4,982 Sq. Ft. LOCATION! LOCATION! LOCATION! Near the Winchester Country Club, fronts the Golfcourse, tranquil setting with views of the brook. Expansive Decks ideal for out door entertaining. The Residence is a New england Style Home with Exquisite Great Room, Fireplaced Reception Hall, Familyroomwith Stone Fireplace,2nd floor Sitting/Tv room.Lower Level walkout suite, media room and Bath. Flexable floorplan,Updated throughout to preserve the charm and character with all the amenities for today's life style. View Details MLS # 71050279 Schedule a Showing Email a Friend

$1,899,000 Virtual Tour 16 Stratford Rd Winchester, MA 7 Beds, 6 Baths, 5,630 Sq. Ft. Old World Charm meets Modern Living! Amazingly updated 1914 Ralph Vinal designed Grand Tudor. 14 rooms, 7 bedrooms, 5.5 baths including master and aupair suite. Easy living only begins to describe this house. Flowing first floor for Enteraining, lower level media room for "date night" and upper floors for private retreat. Huge Master with FP, custom closets, double vanity, steam shower, soaking tub, etc.creates a great escape. Chef's kitchen with all the best!. Gracious yard. Just Enjoy! View Details MLS # 71523374 Schedule a Showing Email a Friend

$1,849,999 Virtual Tour 15 Everett Avenue Winchester, MA 6 Beds, 6 Baths, 5,088 Sq. Ft. Looking for a home with a guest/au pair or office suite above the 2 car garage? Lovely Colonial Revival home by Architect Robert Coit, this house retains the grace and charm of a bygone era with modern amenities.Bright, sunny and spacious rooms complemented by beautiful details - hardwood floors, 4 fireplaces, pocket doors, wainscoting, leaded glass bookcases, french doors, stairway landing window seat and much more. Highly desirable neighborhood. Move right in! View Details MLS # 71519263 Schedule a Showing Email a Friend

$1,849,000 Virtual Tour 65 Myopia Road Winchester, MA 4 Beds, 5 Baths, 6,182 Sq. Ft. Stunning,expanded Colonial in the heart of Myopia Hill, two doors from the golf course w/just under 1 acre of level professionally manicured grounds, in ground gunite pool, new mahogany decking, patio with stylish pavers & stone walls, new glass attrium eat in kitchen area with cathedral ceilings & direct access to the rear yard, new brazilian cherry 1/2 bath off mud room, new cherry Master walk-in dressing room.An inviting open floor plan, great for entertaining.A superb, prestigious property! View Details MLS # 71489186 Schedule a Showing Email a Friend

$1,799,000 Virtual Tour 11 Hutchinson Rd Winchester, MA 7 Beds, 6 Baths, 6,500 Sq. Ft. Open layout w/ gourmet kitchen w/custom cherry cabinets, granite center island and SS appliances, large center island, huge walk in food & butler's pantry w/wet bar. Brazilian cherry floor and high ceilings throughout. Mudroom w/custom storage, open family/dining room, formal DR and LR. Second floor features not only a sumptuous master suite w/ sitting room & double WIC but a huge second master or in-law suite. High efficiency systems, young roof, huge fenced yard and 3 car garage. View Details MLS # 71480523 Schedule a Showing Email a Friend

$1,790,000 Virtual Tour 6 Aristotle Dr. Winchester, MA 5 Beds, 6 Baths, 6,280 Sq. Ft. Classic and Pristine Colonial w/ 3 car garage. Grand Entertaining Spaces. Huge Custom Kitchen with granite & Walk-in Pantry, Master Suite has custom built Walk-in Closet and renovated full bath. 4 other bedrooms on 2nd floor & laundry Rm. In addition, Lg 3rd level plumbed and wired attic, finished walk-out lower level complete with Mudroom, Exercise Room, Playroom and Bonus Room with Full Bath. HW floors throughout home. Beautiful landscaped yard. Gorgeous Home! Don't Miss this Opportunity! View Details MLS # 71497027 Schedule a Showing Email a Friend

$1,689,000 4 Blossom Hill Rd. Winchester, MA 5 Beds, 5 Baths, 5,600 Sq. Ft. Almost finished! Exquisite! Don't miss this wonderful new classic colonial located in a great neighborhood that's ideal for today's discriminating buyer. From the gracious Bay Windows to the stunning Cooks Kitchen, Elegant Dining Room, Fabulous family room, Gorgeous Master Suite with outstanding dressing room, 4 1/2 bathrooms, lower level rec room and office/exercise room, this wonderful home has it all. Bonus! State of the Art Hi-Efficiency Energy Star Construction! View Details MLS # 71435373 Schedule a Showing Email a Friend

$1,599,000 Virtual Tour 28 York Rd Winchester, MA 5 Beds, 6 Baths, 5,100 Sq. Ft. Custom Built New Construction - 5 bed, 5.5 bath Colonial. The moment you arrive you will appreciate the quiet cul-de-sac location. The beautiful stonework & elevated positioning complete the grand approach. Elegant mouldings, dark hard wood floors, high ceilings & chefs kitchen are just a few of the many amenities. A floor plan for today's lifestyle with family room off the kitchen & a living room that is sure to impress. All 2nd floor bed rms feature private baths! The true essence of luxury. View Details MLS # 71527509 Schedule a Showing Email a Friend

$1,549,900 Virtual Tour 3 McCall Road Winchester, MA 4 Beds, 3 Baths, 3,200 Sq. Ft. An exceptional home! This beautifully designed and decorated Garrison Colonial on Myopia Hill is waiting for your approval! With nicely proportioned sun-filled rooms, gorgeous millwork and family-friendly floorplan with open kitchen, eat-in area and family-room, this is a great opportunity to live in one of the prettiest neighborhoods in town. As a bonus, for casual entertaining, the large playroom on the lower level with surround sound system is perfect. The backyard is lovely---nice!!!! View Details MLS # 71479386 Schedule a Showing Email a Friend

MLS Listing Provided By: Listing Agent: Mary Errico Listing Office: Waterfield Sotheby's International Realty

$1,499,900 6 Thornton Rd Winchester, MA 5 Beds, 4 Baths, 4,975 Sq. Ft. Exquisite brand new 12 rm Colonial with approx 5000 sq ft of luxury livingspace to include 5 bdrms,spacious gourmet kitchen w/ breakfast rm, adjoining fireplaced FR w/ cathedral ceiling &sliders out to deck. LV rm w/ built in bkcases & 2nd frpl, DR w/ crwn moldings, chair rail, wainscoting & a 1st fl study. This remarkable home w/ its beautiful craftsmanship&stunning design also has 3.5 bths, finished 3rd fl, 2car garage,walkout lower level,spacious fenced yard & convenient West Side loc View Details MLS # 71442105 Schedule a Showing Email a Friend

$1,499,000 Virtual Tour 14 Herrick Street Winchester, MA 6 Beds, 5 Baths, 4,494 Sq. Ft. Location Location Turn of the century Grande Dame with beautiful detail and natural woodwork. All the charm and appeal of yesteryear but with modern amenities such as large gourmet kitchen and Family Room.Library plus sunroom plus sitting room on first floor.Laundry on second floor and three full floors of living space, Beautiful front and back porches and deck.Best of all there is a fabulous level back yard in one of the finest neighborhoods in Winchester and steps to the town center. View Details MLS # 71527237 Schedule a Showing Email a Friend

$1,450,000 7 Socrates Way Winchester, MA 5 Beds, 3 Baths, 5,343 Sq. Ft. Adjacent to Nutile Fields and one-half mile from Vinson Owen Elementary School, this charming, traditional 5300a 5-bedroom 3.5 bath New England-Styled Colonial, is a wonderfully warm and inviting family home which overlooks conservation land. There is an impressive a"Great Rooma" with 8a windows and a wood-burning stove as well as a spacious sun room, the kitchen and family dining area have been recently remodeled. Magnificently landscaped patio, pool area. View Details MLS # 71520525 Schedule a Showing Email a Friend

$1,399,000 Virtual Tour 11 Ridgefield Rd Winchester, MA 6 Beds, 5 Baths, 5,107 Sq. Ft. Elegant 6 bed Colonial once featured in "Better Homes and Gardens" magazine. Situated in the perfect neighborhood with direct access to the Town forest from the yard. Walk to Town & the commuter rail in minutes. This exceptional property will not disappoint. The spacious kitchen, living & dining rooms are ideal for those who like to entertain. The large master suite features a Romeo & Juliet balcony that overlooks the two-story sun room! Complete with au pair suite and direct exterior access. View Details MLS # 71513940 Schedule a Showing Email a Friend

$1,359,000 2 Stonefield Cir Winchester, MA 5 Beds, 4 Baths, 3,715 Sq. Ft. Come see this masterfully built modern colonial at Stonefield Estates. Built by the same builders that recently had a home featured on HGTV's "House Hunters." Abundant basement storage, sun-drenched living areas ALL ABOVE GRADE, CAD-5 wiring throughout. This handsome center-entrance colonial features well defined spaces for formal occasions as well as an open floor plan for easy entertaining and living. Beautiful bathrooms, bright kitchen, high ceilings and sharp looks define this like new gem. View Details MLS # 71528257 Schedule a Showing Email a Friend

$1,274,900 3 Emerson Road Winchester, MA 4 Beds, 4 Baths, 4,000 Sq. Ft. Beautiful NEW Executive home in top area. Walk to Ambrose School. 3-car garage (2 tandem). Flexible open plan allows for 4th bedrm. Sunny, southern exposure. Custom design w high ceilings and large windows. Sunken living rm w coffered ceiling and see-thru fireplace. Designer kitchen w Top of the line SS appliances and duel-fuel range. Large master w huge dressing rm/closet. Walk-in closets in all bedrms. Heated floors in 2nd flr baths. Large skylighted loft.300 sf basement storage View Details MLS # 71390401 Schedule a Showing Email a Friend

$1,169,000 Virtual Tour 2 Edgewater Pl Winchester, MA 3 Beds, 4 Baths, 3,335 Sq. Ft. A Royal Barry Wills Design. This beautiful custom built sprawling cape has three levels above ground in the rear. Situated in an exclusive 4 home cul-de-sac off of Everett Avenue.Grand and very spacious first floor with beautiful millwork, oversized bay windows, a sunken family room off the kitchen, office, and a sunroom allowing a seasonal glimpse of the Mystic Lakes. Two Master bedrooms on the second floor, each with its own full bath. Lower level offers two more bedrooms or add'l family room View Details MLS # 71518290 Schedule a Showing Email a Friend

MLS Listing Provided By: Listing Agent: Anne Spry Listing Office: Waterfield Sotheby's International Realty

$1,160,000 Virtual Tour 12 Plymouth Rd Winchester, MA 4 Beds, 4 Baths, 4,067 Sq. Ft. Custom built CE colonial w great flow. Wet bar in FP family rm, wainscotting dining rm, FP living rm, cathedral ceiling eating area in kitchen, 1st flr office & dog rm under staircase are a few of the special touches to this home. Lovely private fireplaced master suite w 2 walk-in closets & large master bath. The 2nd flr layout allows for sitting rm, laundry rm & walk-in closet to be reconfigured into a 5th bedrm. Basement includes the 4th fireplace in the gamerm, rec rm and workshop View Details MLS # 71479490 Schedule a Showing Email a Friend

$1,150,000 Virtual Tour 36 Foxcroft Road Winchester, MA 5 Beds, 5 Baths, 3,064 Sq. Ft. Gracious center entrance colonial (Gambrel Roof) located in the "flats". Walk to town , public transportation and the Ambrose Elementary School. Natural woodwork throughout the first floor plus french doors to the living room and dining room, Double sided fireplace in LR/Sunroom, new kitchen, new heating system as well as a five year old super store hot water tank. The big surprise is the exceptionally large backyard with parking for 4 plus cars. This home full of sunshine, a real gem. View Details MLS # 71483554 Schedule a Showing Email a Friend

$1,100,000 7 Wainwright Road, # 55 Winchester, MA 3 Beds, 4 Baths, 4,228 Sq. Ft. Sunny open floor plan w/cathedral ceilings & gleaming hardwood floors. 1st floor master suite with gas fireplace, sliders to deck & master bath. Gourmet kitchen has built-in wine cooler, trash compactor & oversized island w/granite countertop & customized cabinetry. Great work space for your culinary treats. Finished walkout lower level, great room w/fireplace & sliders to deck and wooded views, study area & more. This a"Ea" style unit at the Ledges is customized for todays living! A must see! View Details MLS # 71516637 Schedule a Showing Email a Friend

$995,000 5A Fernway Winchester - Wedgemere, MA 0.51 Acres None View Details MLS # 71524307 Schedule a Showing Email a Friend

$975,000 Virtual Tour 161 Cambridge St Winchester, MA 4 Beds, 4 Baths, 3,300 Sq. Ft. Pride of ownership in this 1854 Antique meticulously maintained and decorator perfect. High ceilings and detail of yesteryear blend with modern floor plan of large kitchen with sitting area and dining space plus mudroom and office area. Large family room with gas fireplace. Third floor suite has bath and built ins and skylight. Formal dining room will take your breath away. Private rear yard with deck. This is a truly extraordinary home. View Details MLS # 71487610 Schedule a Showing Email a Friend

$969,000 7 Pocahontas Dr Winchester, MA 6 Beds, 5 Baths, 4,046 Sq. Ft. Very rare find in Winchester located at end of private and quiet cul-de-sac. Separate entrance for extended living area consisting of two bedrooms and full bath perfect for in laws or au pair suite. This deceiving property offers fifteen rooms complimented by a very generous dining area and kitchen with attached glass enclosed sun room. Steps down a short path finds you standing in Mullin Field and across street from the newly renovated Vinson Owen school. All you can ask for in one package. View Details MLS # 71510802 Schedule a Showing Email a Friend

• Neighborhood Navigator
  • Winchester
  • Lexington
  • Medford
  • Melrose
  • Arlington
  • Reading
  • Wakefield
  • Woburn
  • Stoneham
  • Boston
  • Rockport
  • Gloucester