This property is available to and priced for Income Eligible families in 100% of the moderate-income range. See attached application for eligibility requirements. Throughout the tenure of the current homeowner many upgrades have been made to this property. Roof, new porch, updated Electrical, kitchen cabinets, Gas furnace, DE leading, new brick chimney. The exterior of the home is being prepped at this time for brand new paint on siding and trim. Buyers must complete the application attached prior to any showings.
Classic Winchester Gambrel offering charm, space, and an ideal location close to town and the commuter rail. Tucked away on a quaint court shared with just one other home, this 3-bedroom, 2-bath property blends character with comfortable everyday living. The main level features an inviting fireplace living room, large dining room, full bath, beautiful kitchen with eating bar, and spacious family room with excellent potential for a playroom, media room, or au pair setup. The second level includes three bedrooms, an additional office/bonus room, and a second full bath. Additional highlights include basement laundry, 3-car parking, and garage storage. this property offers ample outdoor space for leisure and entertaining. This residence represents a unique opportunity to acquire a home of significance within a desirable Winchester location. A wonderful opportunity to enjoy Winchester living close to shops, restaurants, and commuting routes.
Set in one of the area’s most beloved neighborhoods, this charming 3 bedroom home blends warmth, comfort, and opportunity on a gorgeous corner lot surrounded by mature landscaping. Inside, an easy flowing layout is filled with abundant natural light, creating bright and inviting living spaces perfect for both everyday living and entertaining. Hard to find first floor bedroom could work as a home office as well. Hardwood floors add timeless character throughout, while the beautiful sun room offers a peaceful retreat to relax and unwind. Step outside to a large deck overlooking the yard, an ideal setting for summer dining, morning coffee, or gathering with friends. Additional highlights include a one car garage, new roof, irrigation well and a full basement ready for your future ideas, whether it’s a playroom, gym, office, or expanded living space. A lovingly maintained home in a quiet, tree-lined neighborhood.
Completely gut renovated in 2023, this stunning home overlooks conservation & offers serene views, privacy & lives like-new construction. The home was thoughtfully redesigned & opened up to feature dramatic soaring vaulted ceilings & an open floor plan, flooded with natural light. The designer kitchen is the centerpiece of the home, showcasing custom cabinetry, paneled appliances, oversized island w/gorgeous natural quartzite countertops, a farmers sink & beautiful details. The wood burning fireplace & wide-plank white oak flooring add warmth. Every space was carefully curated & hand picked, with no detail overlooked. The sunny lower level features a large family room w/ fireplace, full bath, custom laundry room & mudroom. Enjoy a spacious yard & patio perfect for outdoor entertaining & summer dinner parties. Located in a friendly, vibrant neighborhood w/ easy access to town & Boston, this turnkey home offers peaceful surroundings with unmatched convenience. Direct entry 2 car garage.
Freshly painted side-entrance Colonial offering space, flexibility, and a prime Winchester location. The expansive eat-in kitchen flows seamlessly into the dining area and family room, creating an ideal layout for everyday living and entertaining. The main level includes a bedroom or office, full bath, mudroom with laundry, and is well-suited for one-level living. Upstairs features three generously sized bedrooms and a full bath, including a spacious primary with a large closet and sitting area. Enjoy the outdoors from the deck overlooking a fenced yard and detached two-car garage. Bonus heated space above the garage offers endless potential for a gym, office, or retreat. Convenient to Rt. 93, Boston, Middlesex Fells, and Muraco School.
This affordable Colonial in the highly sought-after Muraco School district is brimming with potential and ready for your personal vision. An ideal starter home, it features a spacious backyard overlooking Davidson Park, creating a private and peaceful setting. Conveniently located near parks, bike trails, and public transportation, this home offers an exceptional combination of value, location, and opportunity. Whether you're a contractor, investor, or homeowner looking to build equity, this diamond in the rough is full of possibilities.
This extraordinary 6-bedroom, 6.5-bath luxury home offers approximately 7,400 square feet of impeccably crafted living space designed for sophisticated living and grand-scale entertaining. A dramatic open-concept floor plan is highlighted by soaring ceilings, a statement fireplace, and expansive walls of Pella windows that flood the interiors with natural light. The designer chef’s kitchen is outfitted with a top-of-the-line Thermador appliance suite, custom cabinetry, oversized island, and an elegant dry bar, seamlessly connecting to the home’s refined living and dining spaces. Exquisite custom millwork and premium finishes throughout showcase exceptional craftsmanship at every turn. A private main-level office provides a quiet and distinguished work-from-home setting. Media room and fitness studio provide exceptional versatility for recreation and entertainment. With an expansive deck overlooks meticulously landscaped grounds, creating a seamless indoor-outdoor entertaining.
Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming enclosed entry porch, leading to sun-filled living & dining rooms w/ bay windows. The updated expanded kitchen w/ pantry opens to a bright breakfast room & connects seamlessly to the spacious family rm w/ closets & sliders providing direct access to the expansive multi-tiered decks & private level fenced yard, perfect for entertaining. Upstairs you will find 3 large bedrooms & 2 full baths including a generous primary bedroom w/ walk-in closet. The lower level can be finished for add'l space & includes laundry & storage options. Don't miss this great home complete with EV charger!
This extraordinary European-inspired villa delivers the ambiance of a Tuscan retreat just 8 miles from Boston. Masterfully crafted with a blend of timeless elegance and modern design. A magnificent curved staircase welcomes you into the foyer, leading to sophisticated yet inviting spaces designed for everyday comfort and entertaining. At the heart of the home is a designer chef’s kitchen w/ high-end appliances and finishes, bespoke cabinetry, a fireplace, and adjoining mudroom. French doors open to an outdoor oasis w/ saltwater pool, lush landscaping and granite stone loggia. This home features a primary suite with a spa-like bath and walk-in closet and en-suite secondary bedrooms. The finished lower level w/ au pair suite and other flex space. Additional conveniences: first lvl radiant floor, heated driveway/walk for year-round ease. With its premier location and close proximity to all, this one of a kind home offers a lifestyle of luxury and convenience unlike anything on the market.
Timeless 1920 brick Tudor in the heart of the Flats neighborhood combines all of today’s modern amenities with classic architectural charm to create an exceptional home for modern living offering 6 bedrooms, 3 full and 2 half baths. A welcoming entry opens to a sun-filled living room with custom built-ins, fireplace, and French doors to a private office. The open dining room flows into a chef’s kitchen with oversized island, abundant storage, and adjoining family room ideal for everyday living and entertaining. A custom mudroom, walk-in pantry, and half bath complete the first floor. The primary suite offers ensuite bath and walk in closet. 3 additional bedrooms, a full bath and convenient laundry room complete the second floor. The third floor offers two additional bedrooms, a full bath and ample storage. The finished lower level includes recreation, gym, playroom space, half bath, second laundry room and unfinished storage. Manicured grounds, two-car garage, C/A and irrigation.
Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value. $300/mo HOA.
Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value. $300/mo HOA.
Timeless Victorian grandeur meets modern living in this iconic Winchester home situated on the corner of Wilson Street w/ easy access to Fells trails! This recently renovated sun-filled 6 BR 4 BA home offers nearly 5000 ft.² of beautifully scaled living spaces filled w/ extraordinary architectural charm & elegant details featuring a brand new state of the art gorgeous kitchen w/ Wolf & Sub Zero appliances. A stunning staircase showcases a wall of colorful leaded glass complimented by high ceilings, intricate millwork & dramatic details throughout. The expansive rebuilt wrap-around porch offers wonderful space to enjoy summer evenings & host gatherings. The great layout provides flexibility for entertaining, working from home or extended living needs. The striking façade & stately presence creates an unforgettable first impression ideally located near Winchester Center, commuter rail, shops, restaurants & top rated schools. located in one of Winchester's most sought after neighborhoods
Welcome to this sun-drenched newer construction & freshly updated 4 Bed 2.5 Bath luxury townhome, set on a quiet cul-de-sac with a private, professionally landscaped yard & secret garden. This spacious home lives like a free standing house with a thoughtful layout designed for both everyday living and entertaining. Highlights include soaring 9-foot ceilings, oversized windows & high efficiency heating system. The main level features an open concept living and dining area with a fireplace and chef’s kitchen, w/ dining peninsula opening to a lovely deck overlooking the private garden. Upstairs, four bright bedrooms include a serene primary suite with private balcony, walk-in closets, soaking tub & marble shower. The finished lower level is ideal for a home office, gym, family room or playroom and offers direct access to garage. Minutes to Winchester Center, top rated schools, commuter rail to Boston, & scenic trails, this turnkey home offers refined comfort and an exceptional lifestyle!
Welcome to this sun-drenched newer construction & freshly updated 4 Bed 2.5 Bath luxury townhome, set on a quiet cul-de-sac with a private, professionally landscaped yard & secret garden. This spacious home lives like a free standing house with a thoughtful layout designed for both everyday living and entertaining. Highlights include soaring 9-foot ceilings, oversized windows & high efficiency heating system. The main level features an open concept living and dining area with a fireplace and chef’s kitchen, w/ dining peninsula opening to a lovely deck overlooking the private garden. Upstairs, four bright bedrooms include a serene primary suite with private balcony, walk-in closets, soaking tub & marble shower. The finished lower level is ideal for a home office, gym, family room or playroom and offers direct access to garage. Minutes to Winchester Center, top rated schools, commuter rail to Boston, & scenic trails, this turnkey home offers refined comfort and an exceptional lifestyle!
Beautifully renovated oversized one-bedroom condo at Parkview Condominium featuring an open floor plan and private balcony overlooking a serene Japanese garden and duck pond. Spacious primary bedroom offers room for a king-size bed and includes a walk-in closet. Updated kitchen, bathroom, and flooring provide years of low-maintenance living. Amenities include swimming pool, cabana, picnic grounds, on-site laundry, and ample parking within a gated community. Conveniently located within walking distance to downtown Winchester and public transportation. Condo fee includes heat, hot water, A/C, electricity, water, and sewer.
Just moments from Winchester Center, this townhouse-style condo lives like a single-family, offering space, flow, and flexibility across four finished levels. The main living area is designed for how you actually live, with an open layout that brings the kitchen, dining, and living spaces together seamlessly. Coffered ceilings, wainscoting, and thoughtful updates add character, while the recently renovated kitchen with stainless appliances and clean, modern finishes anchors the space. Whether it’s a quiet night in or a house full of people, it all just works. Upstairs, the front-to-back primary suite offers custom closets and a beautifully updated bath with soaking tub and glass shower. The second level also includes another full bath and laundry. The top floor adds two well-proportioned bedrooms and a full bath. The finished lower level adds bonus space, while a patio extends living outdoors. Two deeded parking spaces and easy access to shops, dining, and commuter rail.
Truly one of a kind new construction blending timeless design with modern luxury, 8 Priscilla Ln offers 6,500± sq ft of thoughtfully designed living space. Elegant archways and a dramatic two-story living room create an immediate sense of scale and character. The chef’s kitchen features custom cabinetry, Thermador appliances, and an oversized island, flowing seamlessly into the main living and dining areas, while the oversized pantry completes the space. Three bedrooms—including the primary suite—feature en suite baths, with two offering spacious walk-in closets. The primary suite provides a spa-inspired bath and a generous walk-in closet. The expansive lower level, with impressive ceiling heights over 10 ft, offers flexible space for an au pair, media room, gym, or additional living area. Designed by Salt and Stone Co., with a two-car garage. Prime location under 1 mile to Winchester Center, commuter rail, and Lincoln Elementary.
Join me Saturday May 23rd 12-2pm for the 1st Open House at this amazing new price! Fabulous 11 room, 4 bedroom Colonial set on a beautiful lot on Winchester’s west side. The first floor offers a bright and sunny, open concept kitchen and family room which creates the perfect space for everyday living and entertaining and leads to a mud room, laundry, and home office . Completing the first floor is half bath off kitchen, a dining room and a front to back, fireplaced, living room with a peaceful screened in porch that creates a serene escape. An expansive deck that overlooks this magnificent property. Upstairs features a beautiful, new, primary en suite with custom walk- in closet. An additional 3 spacious bedrooms and a new full bath complete the second floor. Lower level includes a playroom, a fireplaced den and extensive storage. Close proximity to Vinson-Owen School, Winchester Swin and Tennis Club and Wright Locke Farm, as well as conservation and many walking trails.
Discover this picture perfect 4 BD 3.5 BA colonial in coveted Brooks neighborhood! This distinguished property offers a gourmet kitchen featuring sleek SS appliances, AGA dual fuel range w/ gas burners, center island & tall wine cooler w/sunny brkfst area. The family rm is an architectural focal point, boasting cathedral ceilings, skylights & a cozy fireplace. Natural light floods the home & continues into the formal dining room, breakfast nook, formal living room & home office. The primary suite offers a ensuite bath & large walk in closet. 3 additional bedrooms & a full bath complete the 2nd floor. The finished lower level w/ full bath offers great space for movie nights, kids play space or guest area & gym. This property is complete w/ a 2 car garage & gorgeous level lot. The back yard features an expansive deck, patio & fenced in yard. This home truly has it all! Sought after Brooks neighborhood is close to town, Wedgemere train station & Brooks town forest. Don't miss this one!!
Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves as the anchor for the expansive living and dining areas. The primary sanctuary is a true showstopper, featuring soaring ceilings and a boutique-style walk-in closet of legendary proportions. With six bedrooms and spa-inspired baths, there is plenty of space for multiple uses and configurations. From the lower-level recreation room with patio access to the proximity to Wedge Pond and the Middlesex Fells, this home is designed for indoor and outdoor leisure. Enjoy the convenience of nearby local shopping and easy access to the surrounding areas.
Classic turn-of-the-century Victorian filled with charm and character, ready for its next owner. 5 total bedrooms; 4 on the second floor and 1 on the 3rd floor, plus 3rd floor office. 1.5 baths, this well-maintained home awaits your finishing touches and features hardwood floors throughout, showcasing its timeless architectural details. Enjoy warm summer evenings on the inviting screened front porch. Recent exterior paint, roof and updated high-efficiency gas heating system ensures modern comfort.The large, fenced backyard is perfect for entertaining, play, or gardening, complemented by a detached oversized garage. Ideally located just a short distance to the 2,600-acre Middlesex Fells Reservation perfect for hiking, jogging and dog walking. Close to Winchester Center’s vibrant shops and restaurants, top-rated schools, and commuter rail to Boston. With easy access to Rt. 93, downtown Boston is just minutes away. A rare opportunity to own a classic Victorian in an exceptional location.
Must see! Beautifully renovated & expanded Cape offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr bedrm & full bath, plus a flexible suite w/ kitchenette, sitting room & full bath. Upstairs offers 3 add' bedrooms & a full bath. The finished lower level includes a family room, office, exercise space, bonus room w/ walkout, workshop, storage & cedar closet. Additional highlights include an oversized 2-car garage with EV charger, elevator lift, solar array, & direct access to the apartment featuring vaulted ceilings, gas fireplace, full kitchen, laundry & private deck. Set on an oversized level lot with mature landscaping, deck, patio & gazebo on a quiet cul-de-sac in the Lynch School district
Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz countertops, oversized island, 2 dishwashers & butler’s pantry w/ice maker & wine fridge flowing into formal DR & LR plus a fireplaced FMRM overlooking a meticulously maintained yard. Each oversized bedroom offers an en-suite bath, sitting area & walk-in closet, providing comfort & privacy throughout. The 1st flr includes a private office w/wet bar plus a lavish bedroom wing ideal for guests or multi-generational living. The 3rd floor suite features a full BA & 2 closets, while the finished lower level adds media/game/gym areas w/access to stunning heated pool, complimented by lush outdoor landscape
Set in one of Winchester’s most coveted neighborhoods, this distinguished Robert Coit-designed residence seamlessly blends timeless architecture with exceptional modern living. Rich in original detail and brimming with character, this 4-bedroom, 2.5-bath home is a true testament to enduring craftsmanship. Gracious living spaces are anchored by three fireplaces, creating warmth and elegance throughout. The expansive kitchen is a showpiece—generous in scale and thoughtfully designed for both everyday living and entertaining. A cypress-paneled den with a fireplace is located on the first floor. The top floor offers 1 room with sink and a large open gallery space, perfect for a home office. Outside, the property unfolds into spectacular, professionally curated gardens and lush landscaping, offering a private oasis that changes beautifully with the seasons. There is a full unfinished basement for additional space. Large welcoming front porch, close to the center and top-rated schools.

Winchester is located in Massachusetts. Winchester, Massachusetts 01890has a population of 22,875. Winchester 01890 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 01890 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 01890 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.