Winchester MA Real Estate & Homes for Sale
The median home value in Winchester, MA is $1,370,000.
This is
higher than
the county median home value of $567,300.
The national median home value is $219,700.
The average price of homes sold in Winchester, MA is $1,370,000.
Approximately 82.15% of Winchester homes are owned,
compared to 13.25% rented, while
4.6% are vacant.
Winchester real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you see a property you’re interested in, contact a Winchester real estate agent to arrange a tour today! $1,250,00026 New Meadows Winchester, MA 01890
ADDITIONAL INFORMATIONSunny Single Family home with detached garage on a corner lot with a large deck/yard with a firepit for entertaining and tons of parking. Open floor plan with wood burning fireplace, custom granite kitchen, 3 bedrooms, 1.5 baths on the 1st floor and 3 bedrooms (Master Suite with Jacuzzi) and 2 other bedrooms with a full bath on the 2nd floor. Partially finished walkout basement has a bedroom, sitting room, washer/dryer and gas boiler/60 gallon hot water storage tank. $2,699,0003 Alice Lane Winchester, MA 01890
ADDITIONAL INFORMATIONNEW 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 & modern day family living. The kitchen features an oversized island with seating/ double thick quartz countertops, high-end appliances, wine bar w/ fridge, breakfast nook/dining area. Off the kitchen is a spacious family room w/gas fireplace & direct exterior access w/ sliders leading to large deck or patio & private rear yard. The first floor also has a formal dining room and 5th bed OR home office with adj. 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 w/double vanities, oversized shower & soaking tub! Three additional beds incl. junior suite w/ bath, full hall bath & laundry room finish this level. Finished lower level media/ rec room w/ full bath, 2 car garage direct to great mudroom! 
ADDITIONAL INFORMATIONBeautiful 2br 2bath condominium on 2nd floor with 2 parking spaces at the sought after Willows in Winchester! This south-facing, filling with plenty of nature light, spacious corner unit boasts an open floor plan with living room, dining room and updated kitchen with tiled back-splash, granite countertops, garbage disposal, light fixtures and newer stainless steel appliances. Association amenities include an in-ground pool, exercise room & clubroom. Enjoy the summer at the heated inground/outdoor pool, exercise room, and gorgeous clubhouse. This good size condo has an open floor plan with plenty of natural light. A spacious fireplace living room with a sliding door access to the large balcony overlooking the quiet, fenced back common areas. This fabulous unit is in a convenient location to downtown Winchester shops, restaurants, and the commuter rail to Boston. OPEN HOUSE Sunday at 12:00 pm-2:30 pm! $829,00020 Border St Winchester, MA 01890
Open House: Tuesday, 5/24 4:00-7:00PM ADDITIONAL INFORMATIONSpectacular Custom Built home by a renowned Local Artisan. This beautiful home is situated on a quiet street among the 4 Sister Houses. The home truly features all the comforts- radiant floor heating, Central AC, Central Vac, whole-house and backyard audio, extensive built-ins with and astonishing amount of storage spaces. Charming details such as: old-growth wide pine floors, detailed moldings, graceful entry and incredible staircase, custom interior wood shutters, Douglas Fir interior doors, wine cellar, loft with lookout views, front & back porches, backyard arbor. Built with high-end quality materials - this home was built to last. Marvin Integrity solid wood windows, vented wood siding and roof, 2x6 construction, I-beam floor joists, 40 Yr shingles, cobblestone driveway, bone-dry basement, high-end hardware, light fixtures, and appliances. Conveniently located near 2 mile loop around Horn Pond, bike path, schools, commuter rail, Town CTR, restaurants, Whole Foods, Hospital, MBTA $1,075,00023 Stevens St Winchester, MA 01890
ADDITIONAL INFORMATIONWelcome to 23 Stevens-a bright, beautiful Colonial right in the heart of Winchester! The first floor of the home opens to a large entry foyer that leads into the spacious bay window living room. Stepping through the cased opening brings you to the bright fireplace dining room w/ built ins and another set of bay windows. From there, enjoy the eat-in kitchen with pantry and mudroom to patio. Moving up to the second floor, there are 3 large bedrooms, offering tons of flexibility for an office space, and a full bath. The third floor features a nook w/ a window overlooking the stairwell that offers tremendous potential for an upstairs laundry or kitchenette. Lastly, there is a beautiful skylit bedroom w/ connected bathroom that makes for a great getaway space, studio, or private office. The double width driveway gives you lots of space to accommodate guests & the spacious backyard is a rare find this close to town-plus it abuts public land, making it a kidâs (or kid at heartâs) wonderland! 
ADDITIONAL INFORMATIONMust-see premiere townhome in desirable Pepper Hill Estates! Completely renovated with an open living concept. Bright & sunny unit with all the modern conveniences you've been looking for! Gorgeous hardwood floors w/ added recessed lighting throughout. Updated chef's kitchen w/ custom cabinetry, breakfast bar & stainless steel appliances. Spacious dining room opens to the living room w/ custom built fireplace & access to exterior private deck. Family room is the perfect place to watch your favorite tv show or catch the next game. Half bath completes the first floor. Second floor has a spacious main bedroom w/ en-suite bathroom & an additional bedroom with full bathroom. Finished lower level with bedroom and full bathroom. Incredible access to Wright-Locke Farm, Mullin Field, McClennan Park, & Whipple Hill Reserve with ponds and trails. Conveniently located near Winchester Town Center, Arlington Heights and Lexington Town Center. You will not want to miss this opportunity! $4,175,00054 Johnson Rd Winchester, MA 01890
ADDITIONAL INFORMATIONPresenting a new construction masterpiece that's a refreshing break from the ordinary, it's extraordinary! This exceptional home was designed to be beautiful yet casual, where everyday living is fabulous! From the moment you step through the 8â arched handcrafted wrought-iron front doors you are struck by the impressive 20' soaring foyer, 10' ceilings, custom rift-sawn beams and massive floor-to-ceiling windows. Unparalleled construction, quality and craftsmanship from a master builder w/ 25 yrs experience are apparent. The striking architecture continues on all 4 finished levels leaving one wanting for nothing. Features include incredible kitchen w/ 2 islands, vaulted ceilings throughout, a 3 bay (6 car) garage, breathtaking breakfast nook, butlers & dry pantries, 1st fl study/inlaw, open finished attic, huge finished basement w/ natural light that feels like a 1st floor with game, exercise and media rooms. With excellent location & schools, this unequaled home is a must-see! $2,500,00018 Olde Village Dr Winchester, MA 01890
ADDITIONAL INFORMATIONThis custom-designed Contemporary with Mesh Technology is beautifully situated on a private lot close to the award winning Vinson Owen School. This home is undergoing a full-scale renovation, with substantial additions is completely reimagined and rebuilt with a June move in date. Soaring beamed ceilings in the open living areas are seamless to indoor-outdoor living. Spacious gathering places such as a gourmet kitchen, adjoining dining areas and living area with a gas fireplace Included are 3 en-suite bedrooms. Massive custom designed walk in closet in main bedroom with a peaceful sitting area that flows out to an outdoor porch. Bonus- exercise room with vaulted ceilings with convenient bathroom all on the main bedroom level. Lower level includes media room with a refrigerator sink and fireplace, and wine storage room and study-office that is accessible to the outdoors. 78 Beverly Rd., Arlington MLS #72976676 is an example of developer's work and finishes. $2,195,00022 Amberwood Drive Winchester, MA 01890
ADDITIONAL INFORMATIONStunningly renovated with curated items from around the world, you can tell from the start that this renovation project was done thoughtfully for peaceful moments. Multi-generational living at its best. The list of specialty finishes is long. The home exudes a hint of Asia mixed with eclectic colors in interesting places. The seamlessness of the project from space to space leaves you wishing you could just stay in one spot and breathe. However, this house is meant to be lived in, with space for a home office, playroom, kitchen that flows into an additional meal prep area, first and second floor primary. The house has been styled to live separately or together with the whole clan, the choice is yours. "The wing" has living, meal prep area, dining and primary bedroom along with a laundry room. Upstairs den and office. Front of the house has an office, living room and playroom plus four beds on the second floor with another laundry. Three car garage. It's all here - come and see it! $1,999,00019 Edgehill Rd Winchester, MA 01890
ADDITIONAL INFORMATIONBeautifully renovated 5 bedroom colonial home located in a top neighborhood! The double entry foyer welcomes you into this grand home filled with light, fresh updates and old world charm. The sun drenched living room is oversized with fireplace and walls of windows, flowing graciously into a stunning dining room with built in china cabinets, leaded glass windows, & extraordinary detail. Lovely new eat in kitchen with custom cabinetry, Fisher Paykel paneled fridge, built in bench seating, plus island & adjacent butler pantry w/great storage! Off the kitchen is a great family room w/ sliders to deck and expansive lush yard featuring a large patio w/many perennials & flowering trees. The second floor features an enormous primary suite w/ large bath, fireplace & custom wood shutters plus 2 additional bedrooms, office, laundry and full bath on this floor. The third offers two additional spacious bedrooms. The lower level has a great playroom, second laundry room and abundant storage. $1,299,00022 Glenwood Avenue Winchester, MA 01890
ADDITIONAL INFORMATIONMagnificent oversized lot! This spacious 4/5 bedroom home was recently updated and expanded & offers a new direct entry 2 car garage w/mudroom! Open airy kitchen with maple cabinets, gas cooking and granite counters w/ seating leads to dining room w/sliders to huge deck overlooking amazing fenced yard. A lovely living room w/ fireplace & picture window plus two additional bedrooms or office/bedroom and adjacent full bath complete the first floor. The second floor offers two large bedrooms plus an updated full spa-like bath w/ future expansion potential over the new garage & plenty of storage.This home has been tastefully updated and offers land like no other! The basement can be used as a playroom or media/ gym with further finishing / offering a solid poured concrete foundation & good ceiling height. Don't miss this special home in a great neighborhood w/ easy access to Lynch elementary school, and close proximity to the town center! $999,0001 Marshall Rd Winchester, MA 01890
ADDITIONAL INFORMATIONThis unique property provides a rare opportunity for contractors, builders, or homeowners to renovate this 5-bedroom Colonial into their dream home. Situated in a premier Winchester neighborhood conveniently located nearby schools, library, commuter rail and downtown shops and restaurants. Plenty of upside and possibilities here. The house is sits on a lot with a generous yard, leaving room for potential expansion. High ceilings and a lovely entry foyer greet you at the front door which leads to a welcoming living room with a wood burning fireplace with French doors leading to an adjacent screened porch. A traditional dining room, kitchen and powder room completes the first floor. The second floor offers four generously sized bedrooms and full bath. The third level comprises of the fifth bedroom, sitting room and half bath. Bring your builder and architect to develop and build your custom home. Property is being sold âAs Isâ, buyer is encouraged to do their own due diligence. $1,499,0008 Sachem Rd Winchester, MA 01890
ADDITIONAL INFORMATIONDonât miss this completely updated 4-bed/2-bath expanded Cape with 3200+ sqft of living space in Winchester. From the perfectly manicured lawn & gardens, step into the open kitchen/living/dining area. The kitchen offers stainless steel appliances & quartz countertops. The adjacent living room has custom built-ins & windows on 3 sides. Down the hall are an updated full bath & 1st-floor bedroom (or home office). A family room & mudroom complete the main floor. Upstairs are 3 large bedrooms with wood flooring & custom-cut area rugs. The updated full bath has marble counters & a walk-in glass shower. The lower level consists of a 1-car garage, finished basement (ideal for a rec room, home gym, office, or guest area) & laundry. Off the back is a private patio w upgraded exterior lighting for outdoor entertaining at any time of day. The fenced-in side yard offers the perfect amount of space for any activity. Ideally located only a short walk from the Ambrose School. This property has it all! $1,329,000380 Highland Ave Winchester, MA 01890
ADDITIONAL INFORMATIONRare opportunity to live on the corner of a private cul-de-sac in East Hill! Just minutes from Winchester Center, downtown shops, restaurants & the commuter rail. Captivating Cape has been updated w/ modern conveniences while still maintaining the integrity & charm of the original home. Beautiful craftsmanship throughout featuring gorgeous hardwood floors, custom built-ins, oversized wood burning fireplace, along w/ a sunny Florida room with access to the outdoor patio. Formal dining room is located near the update chef's kitchen. Kitchen features custom cabinetry, SS appliances, beamed ceiling, ample storage & space to eat-in. A cozy family room completes this level. Spacious main bedroom with custom California closets and ensuite bathroom. Three additional bedrooms and a full bathroom complete the second floor living. Outdoor patio surrounded by flower gardens, storage shed and a newly paved driveway. Move into this fabulous home on one of the most desired streets in Winchester! 
ADDITIONAL INFORMATIONShowings begin Friday May 20th. Delightful waterfront home nestled alongside Little Winter pond with fabulous views! This updated contemporary designed home features a stunning entry, vaulted ceilings and walls of windows showcasing the spectacular setting. Updated kitchen w/ adj dining room w/ built in bench flows into the living room w/fplc and family room flooded with natural light w/water views from the many windows & slider to the gorgeous new deck. The main level also offers 3 bedrooms and 2 full baths; awake each morning in the relaxing primary suite w/unsurpassed views, oversized walk-in closet & new bath. The lower level includes a large media room, bedroom, full bath and gym. There are water views from almost every room in this home! The wrap around deck is perfect for enjoying the scenery and for summertime bbq's. There is a lower patio on the water making it easy to canoe/kayak & fish from your own front yard! Enjoy living an active lifestyle in this very special home! 
Open House: Thursday, 5/26 4:00-6:00PM ADDITIONAL INFORMATIONExtensively rehabbed and updated two story Winchester townhome! Beautiful new kitchen with stainless steel appliances, shaker cabinets with dovetail slow close drawers. LED recessed lights. Harvey insulated dual pane windows. Just refinished gleaming oak hardwood floors. 2 new bathrooms with ceramic tile floors. Large living room with picture window. Bedrooms with double closets and mirrored doors. Huge 20'5 x 10'11 main bedroom. 3 new Mitsubishi ductless mini split systems for cooling as well as a new Advantage cast iron boiler (2017) for hot water baseboard heat. 40 gallon Rheem electric hot water heater (2015). Potential to finish large basement for multiple home offices, family room, media room or home fitness area. Great back yard with masonry patio and large storage shed. Quick closing possible if needed. Near McDonald Field for baseball and tennis, fitness centers, health care facilities and Horn Pond. $1,299,0008 Sunset Rd Winchester, MA 01890
ADDITIONAL INFORMATIONHello Winchester! Capacious 5-bed 4-bath home has open floor plan filled w/natural light. Entry foyer w/double coat closets flows into a welcoming wood-burning fireplaced living room & dining area w/expansive windows to enjoy the backyard view. Sunny kitchen has granite counters, ss appliances, island for entertaining, & peninsula overlooking cozy family room. 2 bedrooms & a full bath â great for guests or home office, complete the 1st floor. 2012 2nd story addition created front-to-back primary suite w/walk-in closets, double vanity & tiled shower w/glass surround. Two addâl bedrooms, main bath, & coveted laundry room w/sink completes the 2nd floor. Finished lower level has a bonus room, full bath, & storage. Mahogany front porch is a cheerful place for morning coffee. Relax on the rear deck and enjoy the natural habitat of delicate wood fern and the sound of the Aberjona River. See list of many updates! Convenient to 93, 128, & the Fells Res. Muraco School. $3,550,00010 Sheffield Rd Winchester, MA 01890
ADDITIONAL INFORMATIONRefined, elegant and turnkey, this Colonial Revival is on one of Winchesterâs premier streets. Steps to train, town, and the desirable Ambrose school. Designed for entertaining, working from home and multi-generational, family life, the 1st floor features a beautifully functional, customized chefâs kitchen, spacious living room, family room, dining room, a half bath, & mud room. The 2nd floor boasts a luxurious master suite w/ walk-in closets & large master bath/jacuzzi, plus 2 additional bedrooms & updated bathroom. The 3rd floor includes 3 large bedrooms, walk-ins & other large closets, plus 2 full bathrooms, currently configured w/ large studio/office & spacious study with lovely views of the Sheffield/Everett neighborhood. Fully finished basement with wet bar & wine cellar. New two-car garage, storage shed, patio/deck & sizeable lot. Renovations include kitchen extension, deck, wrap around porch, HVAC, windows, top grade electric & IT wiring, beautiful wood flooring, and more! 
ADDITIONAL INFORMATIONNicely renovated & GREAT price!! This unique 2 bed, 2 bath townhouse offers a different more spacious layout than many here in the association and is located on a nice side street with fenced in yard! This home offers a spacious open living/ dining room with hardwood floors and plenty of natural light. Many updates throughout including a beautiful kitchen with stainless steel appliances, quartz counters and trendy subway tiled back-splash; easy access to the private rear yard w/ patio, perfect for summertime BBQ's! The second floor offers 2 bedrooms including an expanded/oversized primary bedroom with private full bath and large closets. The second bedroom is also spacious with adjacent, updated full bath. The basement offers full expansion potential and is semi-finished with engineered flooring and would make a great family room or at home office/gym. All of this is just minutes from Winchester Center, The train, 7 miles from Boston! $1,349,90015 Garfield Ave Winchester, MA 01890
ADDITIONAL INFORMATIONRenovated inside and out, this great 4 bed 2 bath home w/ fenced in yard has immense curb appeal and a great level lot! This home has everything todays buyers are looking for with an open concept first floor flooded w/ natural light, new windows, high ceilings, hardwood floors, and central air! Kitchen w/ maple cabinets, island, gas cooking & plenty of storage/ prep space with sliders to fabulous deck & grassy yard; perfect for entertaining! Spacious family/ living room, mudroom & full bath complete the first floor. The second floor has 4 rooms, 3 spacious bedrooms plus office and spacious full bath. The third floor offers 2 rooms/ a perfect teen suite or add'l family room plus the 4th bedroom. Partially finished basement with a gym area/ storage /office w/ access to yard. This home is located in a great neighborhood w/ a completely fenced in flat yard with oversized storage shed, just minutes from Winchester center & Train, w/ quick easy access to highways & just 7 miles from Boston! 
ADDITIONAL INFORMATIONLovely 2 bed, 2 bath townhouse home on a nice side street with many recent upgrades & fenced in yard! This home offers a spacious open living/ dining room with hardwood floors and plenty of natural light. Many updates throughout including a beautiful kitchen with stainless steel appliances, quartz counters and trendy subway tiled back-splash; easy access to the private rear yard w/ patio, perfect for summertime BBQ's! The second floor offers 2 bedrooms including an oversized primary bedroom with private full bath and large closets. The second bedroom is also spacious with adjacent, updated full bath. The basement offers full expansion potential and is semi-finished with engineered flooring and would make a great family room or at home office/gym. All of this is just minutes from Winchester Center, The train, 7 miles from Boston! 
ADDITIONAL INFORMATIONFabulous single family alternative in Winchester Crossing. Built in 2004, this 3 floor, 1529 sqft unit offers 2 bedrooms and 2.5 bathrooms. The spacious open floor plan features a huge living room - dining room combination with 8+ foot ceilings and a private deck, all with plentiful natural light. The beautiful eat-in kitchen has ample storage (maple cabinets), modern appliances, and granite counter tops. The high-end master suite is a rare see. The home boasts shiny hardwood floors, luxurious bathrooms including jacuzzi tub, beautifully painted interior, and much more waiting for you to come and see. Do not miss the opportunity to own this unit! $1,149,00032 Cambridge St Winchester, MA 01890
ADDITIONAL INFORMATIONLooking to live in the idyllic Winchester community? Now you can! This charming move-in ready ranch is located just a short drive to the highly acclaimed Ambrose Elementary School, Winchester Boat Club and golf course. Featuring hardwood floors throughout its spacious open concept layout on the main floor, a beautiful kitchen with recessed lighting, granite countertops and an incredible island, this home has a modern touch while still maintaining its exquisite original design. Separated by beautiful French doors, an inviting living with fireplace plus a large family room with soaring cathedral ceilings offer beautiful spaces for relaxation and intimate gatherings. Finished lower level with additional bedroom and bath perfect for in-laws or an au pair suite. Two car garage, plenty of off-street parking and a beautiful deck and patio overlooking a peaceful and private backyard. This home truly has it all! $1,299,00021 Clearwater Rd Winchester, MA 01890
ADDITIONAL INFORMATIONAdorable 4 bedroom 2 bath cape in top East side neighborhood! Situated across from the fells, this nicely updated home is a nature lovers dream! Offering an optional first floor Master with adjacent full bath, plus additional bedroom or home office along with a formal living room w/ wood burning fireplace & bay window, an updated kitchen & dining room leading to great patio and large fenced in yard; side entry w/ mudroom & direct entry to one car garage. The second floor offers two large bedrooms w/ dormers, spacious closets and an updated full bath. Finish the basement for an additional family/game/rec room; expand the house down the road; or simply enjoy as it is. Move right in and enjoy this sweet house on a premiere lot in TOP location with Fells trails and acres of forest right across the street! $1,295,00035 Winthrop Street Ext. Winchester, MA 01890
ADDITIONAL INFORMATIONRare and unique opportunity. Walk to town from this Antique colonial with terrific views of town center off of Highland Ave. Rich with charm with historical significance. A treasure for the Buyer that seeks the unique and a non-cookie cutter Winchester abode. First level consisting of living room/den, dining room, vaulted family room, and kitchen. Front door entrance is part of an enclosed porch. Upper level includes 2 bedrooms and 1 bathroom. Terrific, open 2 car detached garage with ample storage and a renovated slab. Spectacular front and rear yards with space to plan potential expansion/addition. Superb stone wall work throughout landscape, and impressive granite apron at entrance. Quiet side street off of Washington Street. Runs between Highland Avenue and Davey Lane. A legacy residence with priceless historical charm.
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