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49 Sheridan Circle, Winchester
$2,409,000
5 Beds ⋅ 5 Baths ⋅ 73534811 MLS
Like new, built in 2014, this exceptional home offers generous living space, a flexible floor plan, & quality finishes throughout. Situated on a large corner lot in a desirable Winchester neighborhood, the home features a spacious kitchen that opens to the family room w/ fireplace, creating the perfect gathering space. A sun-filled living room & formal dining room provide additional areas for entertaining & everyday living. The oversized primary suite includes a beautiful bath & 2 walk-in closets. Three additional large bedrooms, a full bath, & convenient second-floor laundry complete the 2nd level. The newly finished 3rd floor offers media/ bedroom w/full bath, providing excellent flexibility for guests, a home office, au pair suite, or potential in-law space. The finished lower level includes a rec room, full bath & abundant storage. Outside, enjoy the expansive yard w/ patio, fruit trees & plenty of space for recreation, gardening & more! Don't miss this one!

49 Sheridan Circle, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
15 Yale St, Winchester
$2,700,000
7 Beds ⋅ 4 Baths ⋅ 73510619 MLS
Beautifully renovated 5 bedroom, 11 room home w 2 home offices located in the desirable FLATS area of town. An inviting front porch welcomes you into this special home showcasing the charm & character of historic Winchester, with amenities and layout desired today. Magazine worthy kitchen/dining/ family room! Open concept first floor with 3 rooms directly overlooking gorgeous and private rear yard w/ deck, patio, mature landscape and an abundance of privacy. Oversized 2 car garage is a huge bonus and rarely found in this part of town! Second floor includes 3 beds, 2 full baths & laundry room. 3rd level offers 3 sun drenched oversized Bedrooms w/ full ceiling height & full bath. Primary bedroom suite w/ spa like bath; oversized steam shower w/body sprays/bench/surround sound, radiant flooring & towel warmer plus a large newly constructed walk in coset! Close to the center & train to Boston. Ambrose School*

15 Yale St, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
2 George Road Unit 2, Winchester
$680,000
3 Beds ⋅ 2 Baths ⋅ 73510206 MLS
Inviting 3 Bed 2 bath townhouse situated on one of the largest lots in the neighborhood offering a perfect blend of space and natural light. This home is in great condition with hardwood floors and an updated kitchen with direct access to the yard. The living room with picture window flows into an open concept dining area. Upstairs find three bedrooms and a full updated bath. The finished lower level with additional full bath and laundry adds flexibility for guests, home office, or additional living space. Enjoy the large outdoor lot for family enjoyment and gardening nicely positioned at the intersection of established neighborhoods, including surrounding single-family homes, this location offers both convenience and long-term value close to top rated schools, near Horn pond, Fells trails & close to commuter rail 2 stops to Boston, major routes, and Winchesters' vibrant downtown with many shops and restaurants. Don't miss out on this great value ~move in and enjoy.!

2 George Road Unit 2, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
36 Cambridge St, Winchester
$2,025,000
5 Beds ⋅ 5 Baths ⋅ 73544504 MLS
Welcome to 36 Cambridge Street—an exceptional 5-bed, 5-bathhome blending modern design with everyday comfort inWinchester’s sought-after Lincoln School District. The mainlevel features an open-concept great room, designer kitchenwith large island, walk-in pantry, and a convenient first-floorbedroom with full bath. A spacious mudroom completes theentry. Upstairs, the luxurious primary suite offers two walk-inclosets and a spa-inspired en-suite, along with two additionalbedrooms, full bath, and laundry room. Third floor features abedroom and full bathroom. The finished lower level providesversatile living with a full bath—ideal for media, play, or fitnessspace. Perfectly located near Winchester Center, commuter rail,and the Middlesex Fells, this home offers upscale living andunmatched convenience.

36 Cambridge St, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
24 Hinds Road, Winchester
$1,750,000
4 Beds ⋅ 3 Baths ⋅ 73529658 MLS
Welcome to the home that has it all! Where thoughtful upgrades meet effortless living. This tastefully updated open-concept home is designed for both quiet nights and grand entertaining. Enjoy one-level living with a stunning sun drenched family room, adjacent dining & renovated kitchen with direct outdoor access, ideal for hosting!The home features 4 generously sized bedrooms, and 3 full baths including the primary suite which is a true private retreat w/lavish oversized bath & private home office. The walk-out lower level features additional living space featuring a family/ game/media space w/ a full bathroom. Outside, you have your own backyard oasis! - enjoy the gazebo overlooking the in-ground pool which was fully transformed w/ a new saltwater system, heater, resurfacing & coping or gather around the fire pit patio for fun summer nights. Oversized garage & plenty of parking. Updated systems, renovated kitchen, and updated baths. Move right into your forever home in Winchester!

24 Hinds Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
105 Thornberry Rd, Winchester
$1,899,000
5 Beds ⋅ 3 Baths ⋅ 73523785 MLS
Perfectly situated on Winchester’s sought-after Westside, this beautifully updated Colonial offers 5 bedrooms, 2.5 baths, and exceptional indoor-outdoor living. A recent renovation transformed and expanded the first floor, featuring an updated kitchen with oversized mahogany topped center island, family room, dining room, mudroom, and half bath. The kitchen opens seamlessly to a spacious family room w/ fire place and a large deck overlooking the expansive backyard with private fire pit — ideal for entertaining. Flexible first-floor bedroom or home office. Upstairs includes a primary suite with walk-in closet and en-suite bath, plus three additional bedrooms and updated full bath. The walk-out finished lower level with fireplace offers space for a playroom, gym, media room, or office. 2-car attached garage. Abuts conservation land and the Winchester Swim & Tennis Club, close to Vinson-Owen Elementary, Whipple Hill trails, vibrant downtown Winchester, and major commuting routes.

105 Thornberry Rd, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
115 Church St, Winchester
$2,975,000
7 Beds ⋅ 6 Baths ⋅ 73512327 MLS
Distinguished Colonial Revival located in the desirable “Flats" neighborhood offering 5,888 SF with 7 bedrooms and 6 baths across three finished levels. Period details include a quartered oak foyer and staircase, bay windows, pocket doors, and decorative millwork. Chef's kitchen features a Viking gas range, Thermador refrigerator, and granite countertops. Family room has a wood-burning fireplace and built-ins. Formal living and dining rooms offer generous proportions and period character. Second floor hosts a primary with en suite bath, a second en suite bedroom, and two additional bedrooms served by a hall bath. Renovated third floor features wide pine floors, a full bath, and flexible space for offices or bedrooms. Recreation room has a wet bar, half bath, and a balcony. Situated on a .41-acre corner lot that boasts a large flagstone patio, a basketball court and driveway access from Wedgemere Avenue. Minutes to Winchester Center, commuter rail, schools, and conservation trails.

115 Church St, Winchester

Listing courtesy of Listing Agent: Jennifer Ryer from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
200 Swanton St Unit T34, Winchester
$1,800
1 Beds ⋅ 1 Baths ⋅ 73539000 MLS
Parkview Condominiums 1st flr Studio Suite with UTILITIES INCLUDED! Condo w/Patio view of the Gardens. Laundry room and Pool ; Avail 8/1! Close to Winchester Center and Purple line Train! View our 3D Tour - hardwood floors- PARKING! Patio that overlooks the Garden and the Pool!!! No pets, No smokers. First and Security. Application online.

200 Swanton St Unit T34, Winchester

Listing courtesy of Listing Agent: Catallo Team from Listing Office: Realty ONE Group Cosmopolitan.
41 Cross St, Winchester
$4,500
4 Beds ⋅ 2 Baths ⋅ 73533531 MLS
Available August 1st — a freshly painted side-entrance Colonial offering space, flexibility, and a prime Winchester location. The expansive eat-in kitchen flows into the dining area and family room, ideal for everyday living. The main level offers a bedroom or home office, full bath, and mudroom with laundry — perfect for one-level living. Upstairs are three generous bedrooms and a full bath, including a primary with a large closet and sitting area. Enjoy a deck overlooking a fenced yard, plus a detached two-car garage with bonus heated space above. Rent includes water, sewer, and landscaping; tenant pays electric and gas. Pets welcome (up to 2 dogs); no smoking. Minutes to Rt. 93, Boston, the Middlesex Fells, and short walk to Muraco Elementary School. Shown by appointment only.

41 Cross St, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
4 Lawrence St, Winchester
$3,070,000
6 Beds ⋅ 8 Baths ⋅ 73524328 MLS
A beautifully renovated and expanded Colonial in the Flats, blending old-world charm with modern living that suits a myriad of needs. The main home features high ceilings, restored original woodwork, and updated systems throughout. The kitchen invites the outdoors in with views of the private, tree-lined backyard with mature plantings, an expansive covered patio, and firepit for cozy evenings. The 2nd floor offers 4 beds and 3 baths, including a stunning primary suite with cathedral ceilings, marble bath, and sun deck access. A third-floor flex space adds a bar and bath. The bi-level in-law/au-pair suite is complete with full bath and kitchenette. Add a detached two-car garage with 2nd-story finished living area, bar, and full bath, and there are multiple offerings for autonomy, extended-stay guests, an au-pair, or teens seeking their own space. A rare opportunity to call this exceptional oasis home in the heart of the Flats, with Winchester Center and the commuter rail close by.

4 Lawrence St, Winchester

Listing courtesy of Listing Agent: Burbs to Boston from Listing Office: Compass.
7 Cliff Street, Winchester
$2,800,000
6 Beds ⋅ 4 Baths ⋅ 73509698 MLS
Gracious 1890 colonial on .3 acre lot on dead end overlooking Middlesex Fells. Close to I-93, town center, train, and top Winchester schools (Lincoln Elementary). Welcoming front porch leads to a beautiful foyer. First floor features a living room with wood FP and bookshelves, and a large family room with gas FP accessing a side porch, a back deck and the kitchen. Renovated kitchen has large island, built-in desk and casual eating area. Formal dining room, half bath, mudroom, and pantry at the back staircase complete the 1st floor. Upstairs, the primary suite showcases a tub, shower, double sinks, plus walk-in closet. 3 additional bedrooms share a tiled bath. 3rd floor has another full bath, 2 more bedrooms and an office for a variety of uses. Finished basement houses a large rec room, laundry and mechanical rooms, plus generous storage. Highlights include central air, 2 car garage plus 4 driveway spaces, rear deck, side porch, beautiful landscaping and sprinkler system. Offers 5/5 4p.

7 Cliff Street, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
10 Bonad Road, Winchester
$1,620,000
4 Beds ⋅ 3 Baths ⋅ 73530345 MLS
Welcome home to this sun-filled, south-facing 4-bed Colonial in a beloved Winchester neighborhood. Hardwood floors guide you from the gracious foyer into a spacious, fireplaced living room ideal for gatherings. The airy formal dining room flows seamlessly onto a private back deck overlooking a professionally landscaped, fully fenced yard—perfect for al fresco dining & entertaining. The updated chef's kitchen features stainless appliances & a generous island for everyday living. Upstairs, find 4 spacious bedrooms & a redone full bath boasting marble counters & custom tiled shower. The finished lower level provides exceptional flexibility w/ mudroom, full bath & ample flex space for a family room, gym & play area. Outside features a detached 1-car garage & 4-car driveway. Freshly painted inside & out. Fabulous location, blocks from Muraco Elementary, parks, playgrounds, the Fells & commuter routes. Move right in!

10 Bonad Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
200 Swanton St Unit 222, Winchester
$2,250
1 Beds ⋅ 1 Baths ⋅ 73521785 MLS
Available now 6/1, currently being painted and cleaned for first of the month occupancy. You’ll love this updated one-bedroom unit in the sought-after Parkview Complex, with its access to outdoor space, including private deck, and seasonal pool and barbeque area for residents and guests. Updated kitchen with stainless appliances, including dishwasher. Other building amenities include laundry room, resident and guest parking, elevator, air conditioning, and utilities included. Move right in and enjoy all that Winchester offers: Middlesex Fells, Tri-Community Bikeway, Farmer's Market, library, downtown shops and restaurants, commuter rail station, and easy access to downtown Boston. Credit check will be required by owner.

200 Swanton St Unit 222, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
6 Risley Rd Unit 1, Winchester
$7,400
3 Beds ⋅ 3 Baths ⋅ 73515767 MLS
This completely renovated, thoughtfully designed and very comfortable home is located in a lovely East Hill neighborhood. It features a wonderful floor plan with a living room, open kitchen to dining room, center island and leads to an inviting den with cathedral ceilings. The kitchen includes cathedral ceilings, pantry, granite counters and newer stainless-steel appliances. There is a large deck right off the kitchen perfect for entertaining. The master bedroom suite offers a closet with organization and a master bath with double vanities. The lower level features a finished basement with a granite fireplace. There are hardwood floors and lots of storage space found throughout plus an extra-large garage. You'll enjoy the fenced professionally landscaped level yard complete with an irrigation system. Pride of ownership is found throughout this home. This is NOT your typical rental home. Lincoln School. Easy access to all schools, commuter rail and all major routes. Don't Delay.

6 Risley Rd Unit 1, Winchester

Listing courtesy of Listing Agent: Ida M. Bianco from Listing Office: Coldwell Banker Realty - Lexington.
52 Charles Road Unit 52, Winchester
$4,000
3 Beds ⋅ 2 Baths ⋅ 73510403 MLS
Completely renovated 3-Bedroom townhouse in Winchester for rent. Situated on a cul-de-sac and quiet neighborhood, this 3-bedroom and 1.5 bathroom townhouse was completely renovated in 2020 with a modern kitchen and a very nice floor plan. The first floor has a spacious living room and an open concept kitchen and dining area. Kitchen is equipped with stainless appliances, Quartz counters and a slider that leads to a deck with spacious back yard. Second floor is with three bright and generous bedrooms and an upgraded full bath feathered with beautiful subway tiles and Quartz vanity. Full and finished basement can be set up as a home office or a home gym with its open and spacious space. Great opportunity to move into Winchester and take advantage of the great schools, cozy community and close proximity to Boston. The location is very convenient and close to schools, shopping and highway access.

52 Charles Road Unit 52, Winchester

Listing courtesy of Listing Agent: WINN Rental Team from Listing Office: WINN Real Estate & Consulting.
216 Highland Avenue, Winchester
$2,400,000
5 Beds ⋅ 4 Baths ⋅ 73511014 MLS
Welcome to this fully updated 5 BR, 3.5 BA Victorian showcasing elegant period detail throughout, including intricate woodwork, moldings, high ceilings & hardwood floors. The main level features a gourmet eat-in kitchen w/ quartz island & high-end stainless appliances, opening to a custom butler’s pantry w/ additional oven, sink & wine chiller. A sun-filled family room w/French doors leads to the patio, along w/ a fireplaced living room w/ built-ins, & formal dining room. Home includes 2 primary bedroom options, one on the 2nd floor & a private 3rd-floor primary suite w/ fireplace & full bath. The 2nd level also has 3 additional spacious bedrooms & two full baths, while the 3rd floor features a dramatic great room w/ beamed ceiling.Additional highlights include partially finished basement & newer heat & AC. Enjoy a wrap-around porch, patio & large fenced yard. Ideally located near town center, Middlesex Fells Reservation, Commuter Rail, Lincoln Elementary, Middle School, & Highschool.

216 Highland Avenue, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
12 Hancock St, Winchester
$1,310,000
3 Beds ⋅ 2 Baths ⋅ 73508959 MLS
This beautifully maintained home blends timeless craftsmanship with thoughtful modern updates. Architectural details, including stunning stained-glass windows, add warmth and personality throughout, and pair beautifully with the updated kitchen and baths. Spacious rooms, oversized windows, 9-foot ceilings, and a desirable layout create an airy, expansive feeling that lives larger than the square footage. The primary bedroom features a soaring cathedral ceiling, skylights, and a cozy window seat. Two additional spacious bedrooms and a home office offer flexible space for today’s lifestyle, with the possibility to add a 2nd full bath. Step outside from the fireplaced family room to a level, fenced backyard and patio, ideal for relaxing & entertaining. Just 0.6 miles or less to Winchester’s top-rated schools, the train to Boston, the Fells’ trails & forests, and vibrant shops and cafés, this home delivers classic character paired with exceptional amenities and convenience.

12 Hancock St, Winchester

Listing courtesy of Listing Agent: Elena Langlois from Listing Office: Compass.
71 Sargent Road, Winchester
$1,399,000
3 Beds ⋅ 4 Baths ⋅ 73501230 MLS
This bright and airy home unfolds into nearly 3,000 sq ft of beautifully designed living space, ideally set in a quiet, established Winchester neighborhood. Cherry cabinet kitchen with stainless steel appliances and skylight and a spacious family room with wet bar, The lowest level great room features a stunning floor-to-ceiling stone-faced gas fireplace with expansive western views. Two home offices and an exercise area offer flexibility for today’s lifestyle. Multiple rooms lead to a fabulous 1133 sq ft decking system. Additional highlights include a 4-zone irrigation system, solar panels, newer heat pumps, and mini splits for heat and central air. Convenient to the Middlesex Fells Reservation with miles of trails for hiking, biking, and outdoor recreation. Enjoy easy access to the Wedgemere Station commuter train. A perfect blend of suburban tranquility, natural surroundings, and commuter convenience, a short distance to Winchester Center shops, dining, and community amenities.

71 Sargent Road, Winchester

Listing courtesy of Listing Agent: Bob Bittelari from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
7 Conant Rd Unit 11, Winchester
$3,200
2 Beds ⋅ 3 Baths ⋅ 73524421 MLS
Available 8/1/2026! Highly Desirable The Willows Condominiums.... Sunny 2 bedrooms and 2.5 bathrooms second floor unit... Open layout living room, dining room, kitchen & sliding door leads to private deck.... In-unit laundry, Stainless Steel Appliances, Gas fireplace, Hardwood floors... Gas heating with Central AC... Spacious master bedroom with large walk-in closet and bathroom in suite... Generous second bedroom and family bathroom... The Condominiums has spacious Clubhouse with gym exercise facilities, inground outdoor pool, large entertainment space complete with kitchen... Easy access to Rt 93, Rt 95 & Boston… No Smoke, No Pets. First, last, plus security deposit prior of move in.

7 Conant Rd Unit 11, Winchester

Listing courtesy of Listing Agent: Yongcheng Wang from Listing Office: Phoenix Real Estate Partners, LLC.
11 Highlandview Ave Unit 11, Winchester
$4,450
3 Beds ⋅ 4 Baths ⋅ 73520108 MLS
Group Showings Tuesday May 26th 4-5PM only. Newer construction! Not your typical rental- This spacious townhouse is in great condition, offering 4 floors of space. Wonderful open first floor plan with lots of windows and sunlight overlooking its private fenced in yard and patio space. Hardwood floors, fully applianced maple kitchen. 2nd floor has 2 large bedrooms and a bonus living room space or home office & 1 full bath. 3rd floor primary suite with private bath and walk in closet. Great lower level family room with 1/2 bath and laundry room. Low utility costs. Move right in and start enjoying all that Winchester has to offer! Only 15 minutes from Boston. Large sunny rooms, central A/C. Beautiful fenced in yard!! don't miss this gem!

11 Highlandview Ave Unit 11, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
10 Viking Road, Winchester
$2,549,000
4 Beds ⋅ 4 Baths ⋅ 73518600 MLS
Discover this stunning, freshly updated 4 bedroom, 4 BA oversized brick ranch with open layout & soaring cathedral beamed ceilings on a gorgeous lot with new in-ground pool! The first floor boasts a spectacular custom kitchen with stainless steel appliances, high-end Monogram appliances, two dishwashers & oversized island with seating & rare granite countertops. Relax in the family room with walls of windows overlooking the resort style heated in-ground gunite pool & plenty of yard space. The thoughtfully designed bedroom wing features a sun-filled primary with en-suite marble bath, plus 3 add'l spacious bedrooms and full guest bath. An expansive mudroom provides seamless access to 2 car garage and add'l full bath. Fully finished lower level with exterior access is perfect for entertaining with game/media room, gym, full bath, generously sized laundry room & a custom-designed dog wash room! Outside, you will love the heated pool surrounded by lush landscape. Move right in & enjoy!

10 Viking Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
29 Pilgrim Dr, Winchester
$1,700,000
5 Beds ⋅ 3 Baths ⋅ 73491480 MLS
Beautifully updated home offers generous living spaces & a seamless, open flow. Sun-filled living &dining areas feature hardwood floors, elegant detailing, & a fireplace that creates an inviting atmosphere. The kitchen is thoughtfully designed with quartz countertops, custom cabinetry, stainless appliances, wine chiller, & large island that opens to the dining area, which flows into the family room with direct access outdoors - ideal for yard access & entertaining. French doors between the kitchen, dining, & family room help to create a quieter, more private setting for the bedroom & formal living areas. The primary suite provides a private retreat with a full bath, while three additional bedrooms & full bath complete this level. A finished walk-out lower level adds versatility with a fireplace playroom, 5th bedroom, full bath, & laundry - great for guests or multi-generational living. Landscaped grounds & inviting outdoor areas, complemented by an attached garage & ample parking

29 Pilgrim Dr, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
8 Richardson Street Unit 2, Winchester
$4,500
2 Beds ⋅ 2 Baths ⋅ 73488769 MLS
Beautiful, high end two story condo for rent; close to everything Winchester has to offer! This unique penthouse dulpex condo offers all the space of a single family home with an open concept floor plan featuring high end finishes and hardwood floors throughout. Enjoy a private entrance, a stunning living room w/ high ceilings, a beautiful gas fireplace and high end buit ins; chefs kitchen w/adjacent dining area, pantry/ office area & sliders to deck. Two generous/ oversized sized bedrooms upstairs perfect for sharing if need be; with a stunning designer bath and great closet space. 3 balconies and a unique private roof deck, easy to access with full stairs; perfect for entertaining! This home is not your average rental; the quality/craftsmanship is like no other! Two off- street parking spaces, laundry in unit & fully applianced! This home is ready to enjoy, move right in! Just minutes to the town center, train to Boston, Middlesex Fells & a few miles from Cambridge & downtown Boston!

8 Richardson Street Unit 2, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
50 Oxford Street, Winchester
$3,500,000
5 Beds ⋅ 4 Baths ⋅ 73515077 MLS
**OFFER ACCEPTED OPEN HOUSE CANCELED** Set on an oversized lot w/ a stunning in-ground pool, jacuzzi, pool house & expansive level lawn, this exceptional home blends luxury, privacy, & modern living. Expanded & extensively renovated top-to-bottom, the home features an open layout w/ designer kitchen, spacious family room & oversized attached 2-car garage. Walls of windows & French doors overlook the spectacular private yard, creating seamless indoor-outdoor living. The chef’s kitchen offers double islands, custom cabinetry, & high-end Wolfe & Sub-Zero appliances. Flexible 1st flr w/ potential bedrm & adjacent full bath, oversized dining rm, & high ceilings throughout. The beautiful primary suite features vaulted ceilings & full bath. Generously sized secondary bedrooms & large hall bath w/ soaking tub & separate shower complete the second floor. Finished LL w/ gym/media rm, abundant storage & new systems including electrical, plumbing & windows complete this rare Flats offering!

50 Oxford Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
40 Foxcroft Rd, Winchester
$3,450,000
6 Beds ⋅ 5 Baths ⋅ 73485774 MLS
40 Foxcroft Road presents exceptional new construction in the highly desirable Flats of Winchester. This 6BR, 4.5BA residence spans 6,460 sqft and showcases thoughtfully curated design with an open concept floor plan ideal for modern living and entertaining. The sun-filled living room features soaring vaulted ceilings with exposed wood beams and a gas fireplace, framed by expansive Pella windows. The chef’s kitchen is appointed with a premium Thermador appliance package and an elegant dry bar with integrated lighting. Custom millwork throughout adds warmth and architectural detail. A home office is located on the main level. The luxurious primary suite offers a custom walk-in closet with built-in lighting and a spa-inspired bath with steam shower. The top level offers two additional bedrooms ideal for guests or play space. The finished lower level includes a media room and home gym. A spacious deck overlooks the backyard, creating the perfect setting for outdoor entertaining.

40 Foxcroft Rd, Winchester

Listing courtesy of Listing Agent: The Boston ONE Team from Listing Office: Serhant.
6 Alden Lane, Winchester
$1,275,000
3 Beds ⋅ 2 Baths ⋅ 73520993 MLS
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.

6 Alden Lane, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
2 Gershon Way Unit 2, Winchester
$1,936,000
3 Beds ⋅ 3 Baths ⋅ 73496895 MLS ⋅ ['Winning Farm'] BLDG.
Welcome to Winning Farm of Winchester —an award-winning 55+ community and one of Winchester’s most sought-after addresses for effortless, elevated living. This meticulously maintained and lightly lived-in 3-bedroom, 2.5-bath townhome offers 2,306 sq ft of thoughtfully designed living, showcasing fine craftsmanship & timeless finishes throughout. Sun-drenched interiors highlight gorgeous hardwood floors, soaring ceilings, & an open-concept first floor ideal for both everyday living & entertaining. The main-level primary suite provides convenience & privacy, creating a seamless single-level living option, while additional bedrooms and flexible spaces upstairs offer room for guests, a home office, or hobbies. The home’s inviting layout is complemented by abundant natural light and a warm, welcoming feel in every room. Set within a beautifully maintained community known for its charm and lifestyle, residents enjoy a peaceful setting with close proximity to shops, dining, and major routes.

2 Gershon Way Unit 2, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
56 Yale Street, Winchester
$2,830,000
5 Beds ⋅ 4 Baths ⋅ 73491616 MLS
Gracefully appointed in the sought after "Flats" this stunning Colonial has been superbly expanded & transformed into 4 levels of living space, offering a perfect blend of timeless details with well thought-out quality renovations. The front entry makes a striking first impression! Inside every turn is rich w/ detail- fireplace LR, elegant dining rm, crown molding, wainscoting, HW flrs & an exquisite built-in cabinet. The award-winning kitchen is nothing short of spectacular, with 2 walk-in pantries, wet bar & many outstanding features. You'll love the sunken family rm, adjoining mud rm, & bath. French doors extend the living space to a serene outer setting featuring mahogany deck & an alfresco kitchen. The luxurious primary suite is a stunner w/ spa-like marble bath, steam shower, walk-in closet & unique nursery/office. The finished lower level,2c gar, EZ access to the commuter rail & center of town complete this distinctive home. A rare offering & wonderful opportunity!

56 Yale Street, Winchester

Listing courtesy of Listing Agent: Patricia Fitzgerald from Listing Office: Brad Hutchinson Real Estate.
7 Wainwright Road Unit 30, Winchester
$1,350,000
3 Beds ⋅ 4 Baths ⋅ 73513982 MLS ⋅ ['The Ledges'] BLDG.
This three bedroom condo in Winchester offers 2025 kitchen and bath updates with a thoughtfully designed, expansive layout across multiple levels. Hardwood floors span the first level with a den and open living and dining area ideal for everyday living and entertaining. The second floor features a generous primary suite with walk-in glass shower and stackable laundry, plus an additional bedroom and full bath. The lower level adds a bedroom, full bath, and office, providing flexible space for guests or work from home. New front windows in 2025 enhance natural light. Enjoy treetop views from the private deck, perfect for watching the sunset. Set within a beautifully landscaped community surrounded by lush greenery, this home blends space, comfort, and modern updates in Winchester.

7 Wainwright Road Unit 30, Winchester

Listing courtesy of Listing Agent: Karen S. Garrett from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
200 Swanton St Unit 538, Winchester
$250,000
1 Baths ⋅ 73496212 MLS

200 Swanton St Unit 538, Winchester

Listing courtesy of Listing Agent: Michael Masci from Listing Office: North Atlantic Realty Group.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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