Welcome to this well-maintained 1-bedroom, 1-bathroom condo in the highly desirable Winchester Parkview community. Offering comfortable living at an affordable price, this inviting home is located in a professionally managed building with excellent amenities, including elevator service, on-site management, and an in-ground swimming pool. The HOA fee covers heat, AC, hot water, and electricity, providing exceptional value and convenience. The unit also includes one designated parking space, along with 24-hour guest parking for visitors. Located in a highly sought-after school district known for its top-rated public schools, this property is just minutes from shopping, dining, and the town center. Commuters will appreciate the short walk to the commuter rail station, as well as easy access to major highways and downtown Boston. Don't miss this opportunity to own a bright, comfortable home in one of Winchester's most convenient and desirable communities.
An affordable, 3 bedroom, 1.5 bath townhome at the Residences at Winchester is ready for new owners to make their mark & memories! Located in a quiet neighborhood and part of the new Lynch Elementary School district, this home is part of a duplex and offers an efficient layout and some great perks. Enter to find a large living room with plenty of natural light, which seamlessly flows to the bright kitchen with gleaming black granite counters & a dining area, great for entertaining. Step upstairs to find 3 ample sized bedrooms and a radiant, updated full bath. Hardwood flooring throughout most of the unit, along with energy efficient Harvey windows. Downstairs in the partially finished basement is a sizeable family room, along with storage, and laundry. Enjoy the outdoors in a spacious, flat and private backyard that is maintenance-free because it's covered by the low HOA fee, along with water, sewer & trash removal! Take the opportunity and make Winchester home!
Located in the highly desirable Rangeley Estates - a location that puts everyday conveniences close with comfortable living. The main level is designed for everyday living & entertaining with a spacious fireplaced living room with built-in bookcase, separate family room with large closets, dining room opens to deck for easy indoor/outdoor entertaining, kitchen with island seating & stainless steel appliances, bedroom/office, bathroom with shower, & mudroom with storage. Hardwood floors extend throughout most of the first floor. Upstairs offers two bedrooms & full bath, including primary bedroom with skylight, large walk-in closet. Lower level provides valuable bonus space ideal for home office, gym, or playroom, plus laundry area & storage. Conveniently located near schools, shopping, restaurants, local amenities, train, parks, trails & outdoor recreation - this home offers a neighborhood setting with easy access to everything the area has to offer. A must see!
Winchester Single Family Home with Attached Garage. Completely rebuilt in 2019, 4 Bedrooms + 2 Home Offices & 3.5 Bathrooms across 2,750+ SF! Two "WFH Offices" with Door & Window for privacy. Open-Concept Kitchen: Quartz Island/Countertops & Stainless Steel Appliances. Induction cooking & Hood Venting. Open-Concept Flows into the Connected Dining Room & Sundrenched Living Room with Wood Burning Pellet Stove! Charming New England feature provides efficient winter heating bills! Glass Sliding Doors bring you Outside to a Large Deck with custom Motorized Awning. Multiple Zones: Forced Central Air + Heating. Mudroom & Storage! Thoughtful design: First Floor Bedroom Suite, 1BR/1BA. Upstairs 3 Large Bedrooms & Laundry Room. Finished Top Level Offers "Future" Expansion? The Unfinished Attic offers Epic Storage! The BACKYARD: Wowie a Tree House! Swing, Slide, Climbing Wall & 2 Sheds. Prime Location: Quiet street, walking distance to the new Lynch Elementary + Middle school + High school.
Classic curb appeal abounds at this expansive five-bedroom colonial in the desirable Winchester Highlands neighborhood. The sun-filled first floor features a gracious floor plan with a thoughtfully designed eat-in kitchen showcasing premium appliances including a Sub-Zero refrigerator and Fisher & Paykel DishDrawer. A dining room, living room with wood-burning fireplace, office, mudroom and powder room complete this level. Upstairs, the generous primary suite includes full bath and convenient laundry and is complemented by four additional bedrooms and a family bath. A walk-up attic provides flexible bonus space and storage, while the finished lower level offers a spacious family room, bonus room, and kitchenette with ADU potential. Enjoy the private backyard retreat complete with a fully fenced yard and pristine in-ground pool, plus two-car attached garage. An extraordinary opportunity to enjoy space, comfort, and refined living in one of Winchester’s most sought-after neighborhoods.
Thoughtfully reimagined with a designer’s eye, this beautifully renovated 4 bed, 3.5 bath home delivers refined living across 3 finished levels. Elevated finishes, including custom tile work, white oak flooring, & curated lighting set this home apart from the typical renovation. The heart of the home is a beautifully designed kitchen with an oversized island & seamless connection to the surrounding living spaces. A formal living room with fireplace, spacious den, sun-filled dining area, & inviting sunroom create an ideal layout for both everyday living & entertaining, while a first-floor bedroom & full bath offer flexibility for guests, or home office. Upstairs includes three spacious bedrooms, including a serene primary suite with spa-like bath & dual walk-in closets, plus second-floor laundry. The finished lower level expands your living space with room for a gym, playroom, or media retreat, complete with a half bath & mudroom. A turnkey home designed to fit the way you live today
15K LOT!! Move right into this beautifully updated 4 BR 3 BA open concept home w/stunning rear addition/primary bedroom suite! This impeccably maintained, nicely updated home has a bright & airy open layout w/ abundant natural light streaming through oversized windows. The main living area flows seamlessly from the spacious living room w/beautiful fireplace into the dining room & kitchen. The recently renovated kitchen includes high end appliances, a center island w/ seating & offers clear views of the back yard. Direct access through slider to oversized deck, patio & huge fenced yard with gorgeous perennials. The main floor bedroom wing offers 3 spacious BR's & 2 baths incl the 2 room primary w/office, spa like bath & walk in closet. LL offers add'l BR suite w/ full BA or family room, laundry & storage. Enjoy hardwood floors, central A/C & spacious 2-car garage. This home is perfect for family enjoyment or hosting large gatherings. Located in a vibrant neighborhood near the swim club
Lovingly maintained by the same family for more than 50 years, 38 Robinhood is filled with warmth and ready for its next chapter. This versatile home offers a flexible layout with a fireplaced family room, playroom, bedroom, or home office on the entry level, along with a half bath, laundry area, and direct access to the two-car garage. Upstairs, the sun-drenched living room flows into the open dining area with direct access to the oversized screened porch—perfect for relaxing or entertaining. The eat-in kitchen provides access to the patio and backyard, ideal for summer cookouts. The top floor also features three bedrooms with hardwood floors, a full bath, and a half bath. Conveniently located with easy access to all that Winchester has to offer, this cherished home is not to be missed.
Set back on a private, serene lot, this contemporary home offers peaceful nature views from nearly every window and a bright, open layout designed for effortless indoor-outdoor living. Cathedral ceilings, hardwood floors, two fireplaces, and French doors create inviting living and dining spaces that extend to decks and patios. The kitchen features teak cabinetry, stone counters, stainless appliances, an island, and a sunny window seat. A main-level primary suite with deck access, two walk-in closets, and a spa-like bath provides a calm retreat. Additional bedrooms offer flexibility for rest, work, or guests, while the full walk-out unfinished lower level—with abundant windows and slider—adds exceptional potential for an ADU, future living area, studio, or recreation space. Updated efficient heat pump heating and cooling, an oversized attached garage, professional landscaping, stone walls, sprinklers, and a cul-de-sac setting complete this distinctive property.
Move right into this beautifully updated Colonial set on a level, fenced corner lot. Designed for modern living, this 4-bedroom, 3.5-bath home offers a spacious floor plan with a warm, nature-inspired aesthetic throughout. The inviting family room impresses with a dramatic beamed ceiling, while the primary suite features a cathedral ceiling, walk-in closet & spa-like bath with an oversized shower, soaking tub & double vanity. A second en-suite bedroom, two additional bedrooms & full bath complete the second floor. The partially finished lower level provides flexible bonus space. Outdoors, enjoy a private sports court & expansive fenced yard, ideal for recreation & entertaining. An attached 2-car garage, including one heated bay, adds convenience. Ideally located adjacent to Town Forest walking trails and just minutes from Wedgemere Station, downtown Winchester, schools, parks, and commuter routes. A rare opportunity to enjoy comfort, recreation & convenience in a sought-after location.
Step into the welcoming foyer and take in the period detail: stained-glass windows, large bow windows, detailed moldings, and hardwood floors. The sun-drenched formal dining room is made for gatherings, and the updated kitchen with butler's pantry makes entertaining a pleasure. On the 2nd floor, the primary suite includes a private office and sleeping porch, along with two additional bedrooms, a full bath, and laundry. The 3rd floor offers two more bedrooms and a full bath, providing flexibility for any household. The large screened porch extends living space through the warmer months, providing a quiet spot to read, dine, or relax. The flat backyard is peaceful and private, with perennial gardens and a bluestone patio perfect for al fresco dining. A mudroom and two-car garage add everyday practicality. Set on a quiet, dead-end street, minutes from the trails of the Middlesex Fells, and close to Muraco Elementary, downtown Winchester, the commuter rail, shops, cafes, and restaurants.
Well-maintained brick Cape offering 1996 sq. ft. of comfortable living space and a flexible floor plan. The sought-after first-floor primary bedroom and full bath provide convenient one-level living, complemented by hardwood floors, a fireplaced living room, dining room, sunroom, and an inviting kitchen with exterior access to the deck. A vaulted family room adds valuable living space, while additional bedrooms upstairs accommodate family, guests, or home office needs. Situated on a beautiful level .30-acre lot with a paved driveway and attached garage, this home has been lovingly cared for over the years. Enjoy easy access to Winchester Center's shops, restaurants, parks, trails, and commuter rail. Just minutes from Boston and major routes, the location is ideal for commuters. Winchester is renowned for its top-rated schools, vibrant town center, and exceptional quality of life.
Exceptionally rare 1911 property, fully renovated on prestigious Rangeley Road, steps to town. Set on what is widely regarded as the most iconic street in Winchester, this 5 bedroom, 4.5 bath home captures the essence of the coveted Rangeley Estates lifestyle. Over 7,300 sq ft of total space & architectural character, blending classic design with modern luxury. Grand, sun drenched interiors & a beautifully scaled layout offer multiple living spaces, including a 1st floor office. The Chef’s kitchen opens to a dramatic family room with soaring ceilings and French doors leading to outdoor living. The large finished lower level features a spa style bathroom & a beautiful custom wine cellar. An elegant porch & stone paved half moon driveway, enhance the home’s presence, complemented by a 2-car garage and expansive driveway. Moments to Winchester center, Commuter rail, boutiques, dining and Top-rated schools. Private, discreet, an ideal home setting for an exceptional family living!
New construction 2019, this impressive 4-5-bedroom, 4.5-bath custom built East side colonial offers exceptional space and a highly sought-after floor plan. The chef's eat-in kitchen features a large center island, abundant cabinetry & sunny dining area that seamlessly blends w/ the spacious family room w built ins & fireplace. Sun-filled living and dining rooms are connected by a double-sided fireplace, creating ideal gathering spaces. The stunning oversized primary includes a beautiful bath w/ shower & soaking tub & large walk-in closet. 3 additional generously sized bedrooms and full bath complete the upper level. The finished lower level offers a media room with a 4th fireplace, a BR/Office, full bath & mudroom area. w/direct access to the garage.Enjoy the large yard and patio, perfect for outdoor entertaining. Conveniently located near Winchester center, parks, & commuter routes, this turn-key home combines modern construction, generous living space, and quality finishes throughout
This completely remodeled home is nestled on a dead end street off Brookside Road, offering a serene/ natural setting with unmatched privacy. This home offers 4 bedrooms, and 2.5 baths with three spacious finished levels. The completely reimagined open concept main floor features a stunning kitchen open to dining area and large family room, plus a separate living room, mudroom, half bath and enclosed sun porch. The second floor includes a generous primary suite with views of nothing but nature, a walk-in closet and all new private bath; three additional bedrooms, a full hall bath and second floor laundry complete this floor. The finished walkout lower level offers a fitness room and large recreation room/media/ playroom with walls of windows showcasing the beautiful setting. Conveniently located near the Fells, Tri-Community bike path, Leonard Field & Muraco School but set back in a uniquely private location. Rare opportunity to move into a fully renovated, modern home at great price!
Waiting for you to enjoy: your carefree home with cathedral ceilings, tall sunny windows, exterior deck, living room with fireplace, formal dining room, adjacent den/3rd bedroom, and kitchen with breakfast area! This "A" style Ledges condominium on a private cul-de-sac includes a FIRST FLOOR PRIMARY SUITE with generous bedroom, large closets and primary bath with double sinks, shower and tub. Spacious single floor living! Plus an upper floor with a loft office space overlooking the living room, and an attractive 2d bedroom with full bath. The unfinished walk-out basement gives you significant room to expand. Landscaping, exterior maintenance, snow removal all done for you while you enjoy the association clubhouse, outdoor pool, tennis court and walking trails in the adjacent Sucker Brook Conservation area. Just minutes from Boston via car or train from charming Winchester Center with its coffee shops, restaurants and outdoor summer dining, pharmacies, and Whole Foods Market all near.
Exceptional new construction offering approximately 6,000 sq ft of thoughtfully designed living space with 6 bedrooms, 7.5 baths, and a 3-car garage. A striking exterior showcases natural stonework, copper roof accents, copper gutters, and a welcoming covered porch. Inside, custom millwork, wide-plank hardwood floors, soaring ceilings, a floating staircase, and designer finishes create a timeless yet modern aesthetic. The chef's kitchen features Wolf & Sub-Zero appliances, custom cabinetry, and an oversized island, flowing seamlessly into the main living spaces. Expansive glass doors open to a covered outdoor patio area with a stunning stone fireplace. The luxurious primary suite offers a spa-inspired marble bath and oversized custom walk-in closet. The finished lower level includes a recreation room, wet bar, media space, home gym, and additional entertaining areas. Just moments away from Winchester's vibrant downtown center and the commuter rail, this home is a must see!
Welcomed by a convenient horseshoe driveway surrounded by thoughtfully designed gardens, 211 Forest has undergone a completely reimagined renovation. This curated family residence shows refined attention to detail and a designer’s eye at every turn. From the custom kitchen with bespoke cabinetry and premium hardware, AGA cast-iron range and Liebherr refrigerator to the sunporch filled with natural light, every space reflects intentional design. The living room is anchored by a wood-fired fireplace, while highlights include a 1,000-bottle wine room, home gym, outdoor barrel sauna for daily wellness, whole-house water filtration system with reverse osmosis drinking water, and Sonos surround sound inside and outside. Located in one of Winchester’s most desirable neighborhoods, imagine stepping out your door for a peaceful walk to a trailhead at The Fells or easily biking with your kids to the highly regarded Muraco Elementary School every day.
Easy living awaits at The Village, where this well-maintained, freshly painted, townhouse offers a functional layout, desirable amenities, and a convenient Winchester location. The main level features hardwood floors, an oversized living room with gas fireplace, an open dining area, and kitchen with direct access to a private patio overlooking the beautifully landscaped grounds. A half bath and generous closet space add convenience. Upstairs are 2 bedrooms including a spacious primary suite with walk-in closet and private bath, along with an additional full bath and in-unit laundry. Additional highlights include central air, carport with extra parking, ample storage, fresh interior paint, and custom closet systems. Enjoy access to the community pool, tennis court, clubhouse, and scenic grounds, all just minutes to Winchester Center, commuter rail, shops, restaurants, 2,600 acre Middlesex Fells, and major routes.
Huge Price Drop – Best Value in the Winchester School District! Beautifully maintained townhouse-style condex offering 3 levels of living in a prime Winchester location. This sun-filled home features 3 bedrooms, 2 full baths, 2 half baths, and a flexible third-floor suite perfect as a primary bedroom, guest space, or home office. Recent updates include a 2019 high-efficiency gas boiler, 2019 tankless hot water system, 2023 mini-split cooling system, 2025 new roof, insulated windows, updated kitchen and baths, and hardwood floors throughout. Enjoy a private exclusive-use yard with deck, patio, mature landscaping, storage shed, and 2 off-street parking spaces. Low $100/month condo fee. Ideally located next to Elizabeth C. McDonald Field with tennis courts, sports fields, walking paths, and a new playground, and just minutes to Winchester Center. A rare opportunity and one of the most affordable ways to enjoy top-rated Winchester schools.
Huge Price Drop – Best Value in the Winchester School District! Beautifully maintained townhouse-style condex offering 3 levels of living in a prime Winchester location. This sun-filled home features 3 bedrooms, 2 full baths, 2 half baths, and a flexible third-floor suite perfect as a primary bedroom, guest space, or home office. Recent updates include a 2019 high-efficiency gas boiler, 2019 tankless hot water system, 2023 mini-split cooling system, 2025 new roof, insulated windows, updated kitchen and baths, and hardwood floors throughout. Enjoy a private exclusive-use yard with deck, patio, mature landscaping, storage shed, and 2 off-street parking spaces. Low $100/month condo fee. Ideally located next to Elizabeth C. McDonald Field with tennis courts, sports fields, walking paths, and a new playground, and just minutes to Winchester Center. A rare opportunity and one of the most affordable ways to enjoy top-rated Winchester schools.
Must see this completely renovated & expanded stately brick home located just outside the town center offering the perfect blend of timeless charm & modern living. Thoughtfully re-designed with an open concept layout, the home features a custom high end kitchen that flows into a gorgeous oversized family room addition* w/ walls of windows overlooking a stunning private backyard. Formal LR and DR, mudroom, stylish 1/2 bath & home office/sunroom complete this floor. The second floor offers, three spacious bedrooms and two full baths including the most perfect primary suite w/gorgeous bath plus a sitting room; while the third-floor provides two additional rooms, ideal for guest or office space. Many updates include new hardwood floors, new high end Pella windows, updated electrical, heating and cooling systems finished lower level offers excellent recreation Enjoy the great landscaped yard with patio, lawn and sports court! For sure a favorite gathering spot for family and friends.
Turnkey-ready 4BR, 3 full bath home set on a beautifully landscaped .82-acre lot directly across from the Swim & Tennis Club, where the new owner receives immediate membership! Extensively renovated & thoughtfully designed, this home offers exceptional style & comfort throughout.The stunning 2026 kitchen features custom cabinetry, quartz countertops, center island, designer backsplash, updated lighting, SS appliances, & new hardwood flooring. A gorgeous primary suite, inviting screened porch, cozy gas fireplace, & functional mudroom add warmth & everyday convenience. All 3 bathrooms were tastefully refreshed in 2024 w/ new showers, vanities, fixtures, & tile. Additional improvements include a new roof, updated exterior siding, finished basement, refinished hardwood floors, freshly painted interior, custom closet systems, new washer/dryer, updated front entry tile, & extensive landscaping w/a new front walkway. Just steps from award winning VO elementary school and Wright Locke Farm.
Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient laundry add flexibility for guests or multigenerational living. Upstairs, the luxurious master retreat boasts a cozy gas fireplace, expansive walk-in closet, and spa-like bath, followed by another bedroom with an ensuite bath, and two additional bedrooms sharing a Jack and Jill bath. A finished basement provides versatile space for a gym, media room, or playroom. Enjoy a charming front porch, private back deck, durable Hardy Plank exterior, and attached two-car garage. Exceptional craftsmanship and timeless curb appeal make this a must-see home! Located within the Winchester School District
Enjoy living in sought-after Winchester, just minutes from Winchester Center, local shops, dining, parks, and commuter access. This beautifully updated two-bedroom condo at Parkview features a modern kitchen with stainless steel appliances, perfect for entertaining, fresh paint throughout, and a bright open-concept layout. Both generously sized bedrooms offer excellent closet space and flexibility for comfortable living. The living area opens to scenic views overlooking the duck pond and professionally maintained grounds, creating a peaceful setting to enjoy year-round. The building offers secure card-entry access, ample resident parking, and guest parking area off Swanton Street. The HOA includes heat, hot water, electricity,AC, and access to the in-ground pool, providing exceptional value and convenience. Unit comes with 1 storage unit in basement.
Winchester is located in Massachusetts. Winchester, Massachusetts has a population of 22,875. Winchester is more family-centric than the surrounding county with 48.34% of the households containing married families with children. The county average for households married with children is 35.9%.
The median household income in Winchester, Massachusetts is $184,844. The median household income for the surrounding county is $111,790 compared to the national median of $69,021. The median age of people living in Winchester is 42.4 years.
The average high temperature in July is 82.3 degrees, with an average low temperature in January of 19 degrees. The average rainfall is approximately 46.9 inches per year, with 52.7 inches of snow per year.
