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

$139,900 63 Shore Rd, # 12 Winchester, MA Sq. Ft. Excellent opportunity to own your own office condo at Judkin Green in downtown Winchester. This garden studio office condo consists of 625 square feet of open space with a private bathroom and large storage room. Judkin Green is a professional building with 14 private office suites. One assigned parking space comes with the condo. Just a short walk to Winchester center and the train. View Details MLS # 71329083 Schedule a Showing Email a Friend

$258,900 283 Cross St, # 0 Winchester, MA 2 Beds, 2 Baths, 968 Sq. Ft. Don't miss out on an affordable opportunity to move into prestigious Winchester, noted for its exceptional school system. Move right into this beautifully renovated 2 bdrm, 1 1/2 bath duplex with an updated granite kitchen, upgraded Stainless appliances, spacious master bedroom with great closets, hardwood floors, newer roof and many more amenities. Full spacious basement (ready to be finished), W/D hookups. Public transportation & just minutes from Routes 93 & 95 View Details MLS # 71189291 Schedule a Showing Email a Friend

$299,800 971 Main St, # 971 Winchester, MA 2 Beds, 1 Bath, 990 Sq. Ft. Beautiful very well kept top floor spacious condo with a great open kitchen to livingroom great for entertaining. This unit has been renovated,kitchen with maple cab. a bath with jacuzzi tub,gleaming hardwood floors,fresh paint and new energy star windows with a brick exterior this is a great low maintenance building. The huge attic space has great potential for expansion. This area is close to the pond, parks,commuter rail and much more. This is priced for a quick sale so it won't last long. View Details MLS # 71293809 Schedule a Showing Email a Friend

$385,000 171 Swanton St, # 38 Winchester, MA 2 Beds, 3 Baths, 1,425 Sq. Ft. Very well maintained home at The Village. Nice unit located near the pool and club house and boasts beautiful front and back lawns. This home has an updated kitchen with granite countertops and custom stained oak cabinets, ceramic tile flooring and stainless steel appliances. The Living room and Dining room have cherry hardwood floors That surround the cozy fireplace. This home comes with newer Washer and Dryer. 24 HR NOTICE REQUIRED. SHOWINGS WEEKDAYS 6-8PM. WEEKENDS FLEXIBLE. View Details MLS # 71339297 Schedule a Showing Email a Friend

$389,000 Virtual Tour 12 James St Winchester, MA 3 Beds, 2 Baths, 1,548 Sq. Ft. The perfect starter ranch in the Vinson Owen school district! This three bedroom home is in very nice condition and a great value; just move in. Updated first floor bath, recently refinished hardwood floors throughout, fireplace livingroom, replacement windows, central air, updated heating system. There is a large, heated basement with half bath, perfect for a family room. Garage under with direct access to basement, private yard. Expansion possiblities for a second floor. View Details MLS # 71326942 Schedule a Showing Email a Friend

$389,000 7 Conant Rd, # 38 Winchester, MA 2 Beds, 3 Baths, 1,580 Sq. Ft. ***Fantastic Condo in Winchester, Updated Kitchen, Hardwood Floors,1580 Sq Ft, 2 Level Living. Unit has 2 Br/2.5 Baths plus office, Master Bath,Gas Fireplace,Great Balcony off Master Bedroom, Walk in closets, W/D Hookups.2nd Floor Laundry, Extra Storage in Basement. Pool, Club House and Fitness Center,Just 15 Min Walk to Downtown Winchester,Shopping and Fine dining,Commuter Rail just three stops from North Station, Downtown Boston, Condo Fee includes: Master Insurance, Cable TV, Trash Pickup*** View Details MLS # 71289017 Schedule a Showing Email a Friend

$395,000 171 Swanton Street, # # 68 Winchester, MA 2 Beds, 3 Baths, 1,442 Sq. Ft. Updated, quiet, townhouse. Eco-friendly renovations. Living room w/ built-in surround sound wiring, recessed lighting, f/p, skylights. Newer kitchen w/ granite, stainless, energy efficient appliances. New bath with high end finishes & Jacuzzi tab. Laundry in unit, walk-in closets, private patio, carport parking. Well maintained common areas include pool, tennis courts & club house. Close to town center, shops, restaurants, transportation. Move in ready. 1 year home warranty. View Details MLS # 71334269 Schedule a Showing Email a Friend

$399,900 30 Farrow St Winchester, MA 0.16 Acres FRESHLY DECORATED CHARMING CAPE IN LYNCH SCHOOL AREA, EASY WALK TO TOWN CENTER AND TRAIN TO BOSTON. JUST A BLOCK FROM BICYCLE PATH. NEWER HIGH EFFICIENCY HEATING SYSTEM WITH CENTRAL AIR CONDITIONING. GOOD CHILD SAFE YARD. HOME IS EASILY EXPANDABLE. MOVE-IN CONDITION AND READY FOR YOUR OCCUPANCY. There is a fully habitable small cape on the property. View Details MLS # 71338561 Schedule a Showing Email a Friend

$399,900 30 Farrow St Winchester, MA 3 Beds, 1 Bath, 1,521 Sq. Ft. FRESHLY DECORATED CHARMING CAPE IN LYNCH SCHOOL AREA, EASY WALK TO TOWN CENTER AND TRAIN TO BOSTON. JUST A BLOCK FROM BICYCLE PATH. NEWER HIGH EFFICIENCY HEATING SYSTEM WITH CENTRAL AIR CONDITIONING. GOOD CHILD SAFE YARD. HOME IS EASILY EXPANDABLE. MOVE-IN CONDITION AND READY FOR YOUR OCCUPANCY. View Details MLS # 71297489 Schedule a Showing Email a Friend

$445,000 79 Loring Avenue Winchester, MA 3 Beds, 2 Baths, 1,344 Sq. Ft. Move right in to this terrific Cape which boasts a newer heating system, newer roof, replacement windows, hardwood floors, fireplace and a great yard. A solid home close to park, playground, transportation and excellent schools. Enjoy a cozy evening by the fire, easy access to the Fells, trips to the library and all that Winchester has to offer from this delightful home! View Details MLS # 71338931 Schedule a Showing Email a Friend

$459,900 241 Forest Street Winchester, MA 2 Beds, 1 Bath, 1,055 Sq. Ft. Move quickly---this attractive ranch is in mint condition! Located on a nice corner lot, there is an additional driveway on the side street, Bellevue Avenue. Exquisitely updated with meticulous attention to detail, this solid home is in the Muraco School Distict, close to the Middlesex Fells Reservation and only minutes to Route 93. With a new kitchen, hardwood floors, double-paned windows and fireplaced combination living/dining room, it is a gem. Be sure to notice the beautiful stonework! View Details MLS # 71311188 Schedule a Showing Email a Friend

$469,900 8 Spruce St, # 8 Winchester, MA 5 Beds, 5 Baths, 2,373 Sq. Ft. 1989 Duplex to 2 unit Condex conversion perfect to extended or mufti-generation use. 6 Bedrooms, 5 Bathrooms make for convenient living with additional basement storage. Great home to raise large family. Walk to MURACO, Middle & High Schools, train station, center of town, playgrounds etc.. Appraised at $485K-listed at $469,900 for quick sale. FS by Owner/Broker who has partially moved out. Appraisal available upon request. Excluded items negotiable or will be removed. 2 rooms in basement. View Details MLS # 71329550 Schedule a Showing Email a Friend

$469,900 8 Spruce Winchester, MA 5 Beds, 5 Baths, 2,373 Sq. Ft. 1989 2F conv to 2 condex units perfect for extended or multi-generation family. 5 bedrooms, 5 bathrooms makes for convenient living with additional basement storage. Great home to raise a large family. Walk to MURACO school, MIDDLE AND HIGH SCHOOL, train station, center of town, playgrounds etc.. Home appraised at $485K - listed at $469,900 for quick sale. For Sale by Owner/Broker who has partially moved out. Appraisal available on request. Excluded items negotiable or will be removed. View Details MLS # 71326367 Schedule a Showing Email a Friend

$479,000 45-47 Holland St Winchester, MA 7 Beds, 3 Baths, 2,340 Sq. Ft. Fantastic opportunity to purchase a 2 family in the wonderful town of Winchester. Perfect investment opportunity for a contractor or a family looking to get help with the mortgage. Close to all Winchester has to offer including a short walk to the town center, shopping, train, schools, highways and close proximity to Boston. This home has separate entry ways, separate driveways, a nice, flat yard and plenty of space to raise a family or 2! Motivated seller !! View Details MLS # 71329544 Schedule a Showing Email a Friend

$479,000 160 Pond Street Winchester, MA 2 Beds, 2 Baths, 1,770 Sq. Ft. Superb 7 rm, 2+ BR brick beauty filled w/stunning array of fine architectural & custom features that reflect elegance & warmth in every detail. Kit w/granite counter, wainscot,copper backsplash; cath ceiling & designer lights in DR w/door to deck overlooking lrg yard.1st flr BR w/built-ins. FR w/2 walls of bkshelves. Elegant fplaced LR & full bath. Gorgeous staircase to 2nd flr sitting area, MBR, flex rm that could be 3rd BR,& 2nd full BA w/built-in seat. Nat wdwrk, hwd flrs, skylights, & more. View Details MLS # 71149805 Schedule a Showing Email a Friend

$489,000 20 Fells Rd Winchester, MA 3 Beds, 1 Bath, 1,175 Sq. Ft. Nestled next to the Middlesex Fells Conservation area with its 2575 acres of woodlands, close to Rte. 93, Winchester center, and in the Muraco School District, this Architect-updated colonial has it all! Fully renovated kitchen w/recessed lighting, ss appliances, built-ins, fireslate counters, & hardwood floor, brightly lit dining room w/French doors opening to a spacious deck, fireplaced living room. Three BR 1 BA. Partial basement w/storage. Private tiered yard. New furnace & water heater. View Details MLS # 71308636 Schedule a Showing Email a Friend

$555,000 116 Forest Street Winchester, MA 4 Beds, 2 Baths, 1,581 Sq. Ft. Now here's the charming and unique home you've been looking for! This home was built in the early 1900's and features fireplace, stainless steel appliances, hardwood floors, granite countertops and cathedral ceilings in the upstairs bedrooms. In-law or Au Pair potential on the first floor! This home is approximately 10 miles from Boston, easily accessible to the major highways, and in the highly sought after Muraco School District! Come see it today, you won't be disappointed. View Details MLS # 71326927 Schedule a Showing Email a Friend

$559,000 Virtual Tour 4 Palmer St, # 4 Winchester, MA 3 Beds, 3 Baths, 2,591 Sq. Ft. A beautiful spacious home in a top location near the Flats part of town, The larger of two townhouses, this home offers 3-4 bedrooms, 2 1/2 baths and a wonderful private fenced in yard with new brick patio... located near the tennis courts, Wedge Pond and the new sprinkler park... Easy access to the center, shops, school and the Train. Completely renovated, in move- in condition. The Master suite has a private bath with dressing area and a huge walk in closet. feels like a single family home. View Details MLS # 71334369 Schedule a Showing Email a Friend

$574,900 247 Forest St Winchester, MA 4 Beds, 3 Baths, 2,124 Sq. Ft. NEWLY RENOVATED KITCHEN AND LOWER LVG RM!! Wonderful 4 bedroom home in Muraco school district! Meticulously maintained by original owners. Absolute value for 4 bdrm 2.5 bath with Master bedroom and master bath. Dining room with sliders leading to back porch. Entire exterior just got a fresh coat of paint! 2 car garage leads directly into downstairs family rm. This house has great space and is move in ready. View Details MLS # 71308112 Schedule a Showing Email a Friend

$575,000 3-5-7 Spruce Street, # B Winchester, MA 4 Beds, 4 Baths, 3,300 Sq. Ft. Custom townhouse offering over 3300 sf ft of space. This unit has 4 spacious beadrooms, 3 1/2 baths with a 2 car garage under. A wonderful open floor plan with 9' ceilings, large living room. Granite kitchen with breakfast bar and high end appliances. Master suite with private bath and 2 spacious closets. 3rd floor offers 2 rooms great for teens or extended family with its own full bath. Sliding doors off dining room that leads to a sun drenched deck overlooking a very large fenced in back yard. View Details MLS # 71330923 Schedule a Showing Email a Friend

$579,900 79 Wendell Street Winchester, MA 3 Beds, 4 Baths, 2,184 Sq. Ft. Located on the sunny side of the street, this 1938 Colonial has beautiful gumwood woodwork in the living and dining rooms plus an up-to-date expansive combination kitchen/familyroom. This house has it all---hardwood floors, three and one-half baths, master suite with an extra room for a home office and a finished room in the basement for watching the Patriots. If you like to cook, the open floorplan lends itself to easy entertaining with doors to the deck right off of the large familyroom! View Details MLS # 71308097 Schedule a Showing Email a Friend

$589,000 9 Lockeland Rd Winchester, MA 3 Beds, 2 Baths, 2,218 Sq. Ft. Pristine Westside ranch with many custom features.Open floor plan with living room/dining room and family room with gas fireplace. This home has a private back yard and is set off the street. Attached two car garage.Spacious lower level with rec room and paneled office. Move right into this condo alternative and enjoy carefree living View Details MLS # 71198751 Schedule a Showing Email a Friend

$599,000 23 Pond Street, # 23 Winchester, MA 2 Beds, 3 Baths, 1,638 Sq. Ft. Graystone at Winchester, introducing new D-style "Green" residence.Spacious,sunny 2 bedroom,2 1/2 bath unit with loft and optional study.D floor plan 1638sq ft. Open floor plan with cathedral ceilings, fireplace and hardwood floors. Custom designed kitchen with granite counters and stainless steel appliances.First floor master suite with marble master bath.Private deck overlooking conservation land. Ready for delivery Spring 2012 View Details MLS # 71322954 Schedule a Showing Email a Friend

$619,000 Virtual Tour 83 Church, # 14 Winchester, MA 2 Beds, 3 Baths, 1,484 Sq. Ft. Much sought after in-town location! Welcoming pristine, sun filled unit. Beautifully maintained, new windows, new master bath. Large entertainment size fireplace living room with 12' ceiling and gorgeous staircase. Recently renovated brick building with elevator, basement storage and deeded garage. This unit is tastefully decorated and ready to move in. A feeling of being in the country, yet short walk to trains, town and shopping. Welcome Home! View Details MLS # 71329578 Schedule a Showing Email a Friend

$629,000 25 Pond Street, # 25 Winchester, MA 2 Beds, 3 Baths, 1,638 Sq. Ft. Graystone at Winchester, introducing new D-style "Green" residence.Spacious,sunny 2 bedroom,2 1/2 bath unit with loft and optional study.D floor plan 1638sq ft. Open floor plan with cathedral ceilings, fireplace and hardwood floors. Custom designed kitchen with granite counters and stainless steel appliances.First floor master suite with marble master bath.Private deck overlooking conservation land. Ready for delivery Spring 2012 View Details MLS # 71322959 Schedule a Showing Email a Friend

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