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$1,525,000
4 Beds ⋅ 4 Baths ⋅ 73404362 MLS
This stately home near the Flats blends original character with modern-day living, 8' ceilings and awaits your personal touches. The living room features stunning woodwork, a fireplace, and French doors leading to a window-lined sunroom-ideal for a home office or playroom. The large circular floor plan connects the living room with a formal dining room, family room, half bath and newer kitchen. There’s plenty of space for multiple chefs and friends to gather in this oversized kitchen- the heart of the home. The second floor has a primary suite, 2 more generous bedrooms, closets throughout and a full bath. The third floor offers a 4th bedroom, a "bonus" room, another full bath and storage. The unfinished basement includes a laundry room and the opportunity to expand. Set on a .25 acre corner lot, this home offers a 2-level detached garage, a tranquil deck and patio-all in a thriving, sought-after neighborhood near VO Elementary, parks, trails, and the 20-minute commuter train to Boston

5 Thornton Road, Winchester

Listing courtesy of Listing Agent: Lynne Russo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$3,450,000
5 Beds ⋅ 5 Baths ⋅ 73334029 MLS
Experience the timeless charm of this stunning English Tudor in Winchester’s coveted Flats neighborhood. Set on an oversized lot with mature landscaping, this home is undergoing a full renovation and expansion by Mark Stephen Development, blending classic elegance with modern luxury. The reimagined design features two fireplaces, an expansive family room, living room, dining room, first- and second-floor studies, a butler’s pantry, and a walk-in pantry, all centered around a breathtaking chef’s kitchen. The home offers 5 bedrooms and 4.5 bathrooms, including a luxurious primary suite being created as part of the addition. A front courtyard adds charm, while a backyard patio will provide the perfect setting for outdoor entertaining and relaxation. Premium finishes and custom millwork details will elevate the design, with opportunities for buyers to explore personalization.  A rare opportunity to own a masterfully redesigned home in one of Winchester’s most sought-after neighborhoods!

58 Wedgemere Ave, Winchester

Listing courtesy of Listing Agent: Mark Donnellan from Listing Office: Advisors Living - Winchester.
$2,150
1 Beds ⋅ 1 Baths ⋅ 73415025 MLS
*NO FEE! $$$ PRICE BREAK and ALL UTILITIES INCLUDED!!!! Ground Level with Private Entrance. NO STAIRS! Lovely terrace level unit at Parkview available 9/1. This well cared for home includes dishwasher, on site laundry, parking,Situated in an very convenient location, near everything! Enjoy the beautifully landscaped common area with pool, cabana and picnic table. Super Value with ALL UTILITIES INCLUDED make this a must see!. Sorry No pets. Appointment Required

200 Swanton St Unit T23, Winchester

Listing courtesy of Listing Agent: David Divecchia from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$710,000
2 Beds ⋅ 2 Baths ⋅ 73380836 MLS ⋅ ['Wedgewood Place Condominium'] BLDG.
Back on Market - buyer got cold feet. Welcome to Wedgewood Place at 666 Main Street in Winchester Center - a perfect blend of small-town charm and urban convenience. This desirable and well-maintained 2 bed/2 bath home comes with 1 covered parking. Enjoy a spacious open-concept layout with a wood-burning fireplace, screened-in balcony overlooking courtyard & pool, and updated kitchen and guest bath. The oversized primary suite offers a walk-in closet, en-suite bath, and an additional vanity area. Additional features include new floors throughout, central air, extra storage, shared outdoor pool, professional management, and shared laundry on the same floor (in-unit laundry can be installed). A great elevator building in an unbeatable location. Everything that Winchester Centre has to offer is right at your doorstep - shops, restaurants, grocery stores, parks, commuter rail & more. Easy access to I-93 & I-95.

666 Main St Unit 206, Winchester

Listing courtesy of Listing Agent: Sveta Vakhitova from Listing Office: Berkshire Hathaway HomeServices Warren Residential.
$740,000
3 Beds ⋅ 1 Baths ⋅ 73416532 MLS
Turn-key 3-bed condo offers effortless living just moments from downtown Winchester, Muraco School, & Middlesex Fells—nothing to do but unpack your bags & settle in. The main level offers a spacious entry area that functions well as a mudroom or sitting room, along with a sunny living room, dining room, & renovated kitchen featuring granite counters, center island, ss appliances, Sub-Zero fridge, & adjacent laundry. The first-floor bedroom offers flexible use & could double as an office, den, or playroom. The full bathroom has been tastefully updated. Two bedrooms upstairs, including a primary with a double closet. Outside, enjoy a freshly painted exterior, fenced yard with generous patio. Additional highlights include hardwood floors throughout, central A/C, replacement windows, updated electrical, plenty of storage & low condo fee. Whether you're downsizing, just starting out, or seeking a flexible layout, this home delivers ease, comfort, & convenience in a top Winchester location.

15 Governors Ave Unit 1, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Advisors Living - Winchester.
$635,000
2 Beds ⋅ 1 Baths ⋅ 73415414 MLS
2 Bedroom at Church Place in Winchester Center! Move-in ready and filled with natural light, this beautifully maintained 2BR 1 BA condo is ideally located in the heart of the center. Perfect for down-sizers or anyone seeking easy living w/ access to top-rated schools & all the conveniences right outside your door. This bright and airy unit offers an open floor plan with high ceilings & beautiful arched windows in every room. The spacious kitchen offers plenty of cabinetry and a great open feel. Generous closet space, in-unit laundry, and low-maintenance living including trash and snow removal make this home as practical as it is charming. Take the elevator up to your private entrance hall or use a quick set of stairs. Enjoy stunning views of the town and unbeatable convenience, just a short stroll to the commuter rail, library, shops, and popular restaurants. Rare offering with two deeded parking spaces just steps from the building's side entrance. A true gem in a sought-after location

115 Washington Street Unit 2A, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,950
2 Beds ⋅ 1 Baths ⋅ 73403379 MLS
Welcome to this beautifully home in a prime Winchester location! Recently gut renovated and in pristine condition, this unit is truly move-in ready.The open floor plan features gleaming hardwood floors, a spacious living area, and a stunning chef’s kitchen with granite countertops, stainless steel appliances, new cabinetry, and a charming breakfast nook with wet bar. Enjoy the convenience of in-unit laundry, a private deck overlooking the manicured shared backyard, and generous attic storage. Just a short stroll to Winchester Center and minutes from the commuter rail, public transportation, and highway access, this location is perfect for commuters.

37-39 Spruce Street Unit 37, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$868,000
3 Beds ⋅ 2 Baths ⋅ 73365747 MLS
Lovingly cared for by its original owners for nearly 70 years, this charming ranch-style home rests proudly on a desirable corner lot in a welcoming, established neighborhood. Offering 3 comfortable bedrooms, 1.5 bathrooms, and two fireplaces, the home is filled with warmth, character, and exciting potential for new owners to make it their own. The yard comes alive each spring with vibrant perennial gardens and fresh mint, creating a wonderful outdoor space with plenty of room to relax, entertain, or garden. Convenient off-street parking for four vehicles and a handy storage shed add even more functionality to the property. The partially finished, heated basement—with its vintage bar, cozy fireplace, and half bath—was once the lively heart of family gatherings and celebrations, and is ready for a fresh vision. Full of history, heart, and possibilities, this well-loved home is ready to begin its next chapter. Offers due by Tuesday May 6th at noon.

235 Cross Street, Winchester

Listing courtesy of Listing Agent: Melanie Lentini from Listing Office: Leading Edge Real Estate.
$690,000
2 Beds ⋅ 2 Baths ⋅ 73391455 MLS ⋅ ['Wedge Pond Condominium'] BLDG.
Buyer's cold feet gives you a second chance to own a well-maintained 2-bed, 1.5-bath townhouse-style condo offering scenic views of Wedge Pond. The main level features hardwood floors, a spacious living area, half bath, and a kitchen with granite countertops and stainless steel appliances. Upstairs offers two bedrooms and a full bath. The finished lower level provides versatile space for a family room, home office, or gym. Additional highlights include in-unit laundry and deeded parking. Conveniently located near Winchester Center, the commuter rail, shops, restaurants, and parks. This is a rare opportunity for pond-side living in one of Winchester’s most desirable locations.

50 Lake St Unit B, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$9,400
5 Beds ⋅ 5 Baths ⋅ 73387468 MLS
Fabulous rental opportunity with full wing of an additional in-law suite for multi-generational living at its best. Beautiful designers’ grade high-end finishes throughout! Features separate side entry with inviting south-facing covered porch, a dramatic two-story foyer/ceiling, and the main kitchen that flows into an additional meal prep kitchen area with integrated appliances – Thermador brand, with beautiful quartz countertops, backsplashes, with counter and bar seating area. Both first & second floor en-suite primary bedrooms with luxury tubs & exudes eclectic chic. "The wing" has living, meal prep area, dining and first-floor primary ensuite bedroom, laundry room, second floor den & an office. Front of the house has a kitchen, office, living room and playroom plus four beds on the second floor with another laundry. Multiple accesses with good flows to the large deck and beautiful backyard. Three car garage. Energy efficient solar feature! Available 8/1.

22 Amberwood Dr, Winchester

Listing courtesy of Listing Agent: Anita Lin from Listing Office: Coldwell Banker Realty - Lexington.
$1,510,000
5 Beds ⋅ 3 Baths ⋅ 73416499 MLS
Charming turn-of-the-century 5-bedroom Gambrel-style home in move-in condition, blending classic character with modern updates. This spacious residence features a beautifully updated interior with central air, a stunning primary suite with private bath, custom closet system, and generous living spaces throughout. The detached 2-car garage adds convenience, while the location offers unbeatable lifestyle perks—just a short stroll to the 2,600-acre Middlesex Fells Reservation. Enjoy easy access to Winchester Center’s shops, restaurants, top-rated schools, and public transportation, including the commuter rail to Boston. Quick access to Rt. 93 puts downtown Boston just minutes away. Basement features small home office with direct access to Beacon Hill style back yard.

155 Highland Ave, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Advisors Living - Winchester.
$3,174,500
6 Beds ⋅ 5 Baths ⋅ 73401615 MLS
Just 3 years young, this pristine masterpiece is nestled in a sought-after neighborhood just footsteps from the Town Forest and within walking distance of Wedgemere Station and Downtown Winchester. Step into the first floor and be captivated by the soaring ceilings. The showstopping kitchen features a SubZero fridge, a Bertazzoni 48” range, and a full eat-in area. This space flows into the family room, where a beamed ceiling and a cozy fireplace create an inviting atmosphere. For guests, a 1st-floor bedroom with a full bath is readily available. The formal living room stands out with its elegant coffered ceiling. Retreat to the primary, a true sanctuary with vaulted ceilings, dual walk-in closets, a dressing room, and a spa-like bath. The 3rd floor and lower level offer boundless potential. A home office, media room, game room, gym, bedrooms, you name it—you get it! Homes like this are rare, where smart technology meets modern luxury, and this one is ready to welcome its new owner.

18 Wickham Road, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
$2,800
2 Beds ⋅ 2 Baths ⋅ 73385712 MLS
Available September 1, 2025! Don’t miss this charming and spacious 6-room duplex townhouse—ready for you to move right in! This well-maintained home features a bright and airy living room and formal dining area, perfect for relaxing or entertaining. The renovated kitchen boasts granite countertops, modern finishes, and a walk-out to your private fenced yard—ideal for seamless indoor-outdoor living. Upstairs, you'll find a generously sized master bedroom complete with an en-suite master bath featuring a stand-up shower. The partially finished basement offers a large family room or playroom, plus in-unit laundry and extra storage space for added convenience. The property also includes two off-street parking spaces. Convenient to all that Winchester has to offer. This home offers the perfect blend of space, comfort, and location. This is a rare opportunity to enjoy a townhouse lifestyle. No access until early July.

273 Cross St Unit 273, Winchester

Listing courtesy of Listing Agent: Jessie Xu from Listing Office: Phoenix Real Estate Partners, LLC.
$1,850
2 Beds ⋅ 1 Baths ⋅ 73421401 MLS
Spacious two bedroom apartment with eat-in kitchen, shiny wood floors and freshly painted interior. Features include gas heat, washer and dryer, basement storage, and two reserved parking spaces in addition to a 1 car garage. Great location close to walking trails, public transit, schools, and easy highway access. Enjoy all the amenities that Winchester offers. ***Showings start on Monday, 8/25/25***

26 Swanton Unit 1, Winchester

Listing courtesy of Listing Agent: Vantage Point Team from Listing Office: William Raveis R.E. & Home Services.
$825,000
3 Beds ⋅ 3 Baths ⋅ 73406431 MLS ⋅ ['The Village In Winchester'] BLDG.
Turn-key end-unit townhouse in Winchester’s sought-after community! Sun-filled open layout with wood floors, quartz kitchen countertops, modern cabinets, and stainless appliances. Two renovated baths feature designer tile and sleek fixtures. Enjoy high-efficiency HVAC with Energy Recovery Ventilation, radiant-heated floors, water filtration, and in-unit laundry. Step outside to a private patio overlooking a professionally maintained yard. Attached garage with two extra off-street parking spaces and generous storage. Community amenities include a pool, tennis court, and clubhouse in a lush, welcoming neighborhood. Minutes to Winchester Center shops, cafés, commuter rail, parks, and the brand-new Lynch Elementary School opening this fall. Move right in and enjoy effortless living!

171 Swanton St Unit 64, Winchester

Listing courtesy of Listing Agent: Xiaoli Xie from Listing Office: JKS Boston Realty LLC.
$2,350,000
6 Beds ⋅ 5 Baths ⋅ 73387723 MLS
Gracious and fully restored, this stunning 6-bedroom, 4.5-bath Victorian blends timeless elegance with luxurious modern updates. Rich with sumptuous period details and soaring 9' ceilings, the inviting first floor features a grand marble foyer with custom built-ins and a sweeping staircase. The formal living room offers a stately fireplace, while the chef’s kitchen—complete with expansive quartz island and Thermador appliances—opens to a refined dining area and warm, light-filled family room with gas fireplace and custom built-ins. The serene primary suite boasts a spa-like bath and private dressing room. Five additional bedrooms provide versatility for guests or offices. Enjoy a bonus room, full bath & mudroom on the walk-out lower level. Fully fenced level yard. Ideally located near Winchester Center, the Boat Club, Country Club, commuter rail, and just 10 miles to Boston.

107 Cambridge Street, Winchester

Listing courtesy of Listing Agent: Stephen Stratford from Listing Office: William Raveis R.E. & Home Services.
$2,218,500
5 Beds ⋅ 5 Baths ⋅ 73380423 MLS
Experience breathtaking Boston skyline views from nearly every room in this exquisitely maintained dream home—your own private oasis of serenity and style. Thoughtfully expanded in 2020, it features a new en-suite with a private bath and a dramatically enlarged, open-concept kitchen ideal for entertaining. With 5 bedrooms and 5 beautifully appointed baths—including four en-suites—this home blends elegance with comfort. The grand dining room boasts a cathedral ceiling and fireplace, while the inviting living room offers a second fireplace for cozy evenings. The luxurious primary suite is a spa-like retreat with radiant-heated floor. Premium upgrades include Hunter Douglas electric shades, Ethan Allen interiors, tiered decks, central A/C, central vacuum, and a two-car garage. Located near top-rated schools and the MBTA, it offers the perfect balance of peaceful living and city convenience.

17 Wagon Wheel Road, Winchester

Listing courtesy of Listing Agent: Yifei Wang from Listing Office: Dreamega International Realty LLC.
$6,500
4 Beds ⋅ 3 Baths ⋅ 73419427 MLS
Modern 4-Bedroom Townhouse for Rent in Prime Winchester Location Available now! This stunning 2021-built townhouse offers modern living at its finest with 4 spacious bedrooms, 2.5 stylish bathrooms, and a bright, open-concept layout perfect for relaxing or entertaining. Enjoy the convenience of an attached garage, a large fenced backyard, and high-end finishes throughout. Located just steps from Winchester High School and within walking distance to the town center and public library, you'll have easy access to top-rated schools, shops, restaurants, and local amenities. Don't miss out on this exceptional rental opportunity schedule a showing today!

72 Holland St Unit 72, Winchester

Listing courtesy of Listing Agent: Yuanming Cheng from Listing Office: Dreamega International Realty LLC.
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 73407616 MLS
Have you ever dreamed of owning a house with a white picket fence? Here it is! Eight rooms, four bedrooms, 2.5 baths. Corner lot with backyard patio, shed and one car garage. The large living room with many windows and a fireplace opens to the dining room. French doors from the dining room lead to a room that can be used as a family room, play room for the kids, or another bedroom. The pine-paneled, eat-in kitchen is modest yet efficient. The kitchen flows to back entrance, where a half bath is located. Central air conditioning on the second floor and heated floors in the full baths offer comfort in all seasons. The white picket fence and a perennial garden of hosta and day lilies border the property. The new, state-of-the-art Lynch Elementary School, slated to open this Fall, is just around the corner. The Horn Pond Recreation Area, with scenic walking trails, is also close by. Convenient to major highways. Plenty of storage in attic and spacious basement.

70 Woodside Road, Winchester

Listing courtesy of Listing Agent: Carolyn Vernaglia from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$2,500,000
5 Beds ⋅ 5 Baths ⋅ 73377775 MLS
*** OPEN HOUSE CANCELLED**** OFFER ACCEPTED Presenting 12 Olde Lyme Rd, where classic Colonial charm meets modern style + convenience. Nestled at the end of a private cul-de-sac, and just a short walk to the coveted Vinson-Owen school, this 5-bedroom, 4.5-bath home has been expanded with purpose and thoughtfully renovated in 2017. The redesign includes high-end finishes and exquisite updates throughout, with no area left untouched. Offering the versatility of a 1st OR 2nd-floor primary suite, this home will meet the demands of any buyer. The large kitchen/open family room overlooks Sucker Brook woods and a stunning, newly landscaped backyard, perfect for entertaining. Second level features 3 bedrooms, 2 full baths, + an updated laundry room with a full staircase to approx. 600 SF unfinished walk-up attic space. Lower level features a guest/au pair suite with walk out access + an expansive movie room/play area.

12 Olde Lyme Rd, Winchester

Listing courtesy of Listing Agent: Mary Beth McGillicuddy from Listing Office: Engel & Volkers, South Shore.
$720,000
2 Beds ⋅ 2 Baths ⋅ 73405870 MLS ⋅ ['Winchester Lakeside Condominium'] BLDG.
Immerse yourself in the vibrant heart of Winchester Center with this exquisite 2-bedroom, 1.5-bathroom condominium! Step into the open-concept living and dining area, where a modern touch meets downtown flair. A rare freestanding wood-burning fireplace accentuates the space, offering warmth and a touch of classic charm. Delight in the recently renovated kitchen, designed for both style and utility. The unit boasts two expansive rooftop patios, offering boundless possibilities. Whether you envision a tranquil retreat under the stars or a sophisticated dining area overlooking the vibrant town center, these outdoor spaces are sure to inspire. Practical features include abundant storage, in-unit laundry, ensuring convenience, and one off-street parking space. This prime location allows you to walk to the BRAND NEW commuter rail, grocery store, restaurants, shops, and everything our idyllic town center has to offer—enhancing the ease of daily life!

29 Vine Street Unit 7, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
$1,062,350
3 Beds ⋅ 2 Baths ⋅ 73387071 MLS
Located in a beautiful neighborhood, this thoughtfully renovated 3-bed, 2-bath home with a custom built free standing office/cottage/gym/ movie house, blends timeless charm w/ modern comfort. Sunlight pours into the open living spaces, highlighting original details & gleaming refinished hardwood floors. The inviting living room features a cozy fireplace w/ built ins, the dining room is perfect for gatherings. A bright family room boasts vaulted ceilings & skylights, creating an airy, welcoming atmosphere. Central AC ensures year-round comfort. Outside, the custom-built cottage offers a space for everybody with tall ceilings, custom cabinetry & window seat, AC/ heat, a spacious king-size loft & ethernet connection--ideal as a home office, gym, or studio. Many thoughtful upgrades have been made to this picturesque home. Enjoy the level, fenced-in yard, perfect for entertaining, gardening, or play. Close to downtown Winchester, schools, The Fells, Leonard field & new playground!

8 Garfield Avenue, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,330,000
3 Beds ⋅ 3 Baths ⋅ 73362145 MLS
Location, location, location! Rare opportunity to own this stunning Italianate home, in a desirable neighborhood, steps from Town Center! This property has been lovingly owned & maintained by the same family for 70+ years and is now ready for new owners. Prepare to fall in love with the charm and period details of this circa 1870 historic home, the first house built on Hillside Ave. The 1st floor offers a gracious living room with fireplace, spacious dining room with ample windows and 2 covered porches for outdoor enjoyment, family room with marble fireplace & wood-burning stove, and a bright and cheery kitchen with a generous pantry. The 2nd floor offers 3 bedrooms, home office, and 2 bathrooms. Special features include high ceilings, Victorian hanging front stairwell, screened-in porch, mudroom, central AC, back staircase, walk-up attic and more. Bring your creative design ideas and personalize this home to make it yours. Close to schools, commuter rail, the Fells, and conveniences!

14 Hillside Ave, Winchester

Listing courtesy of Listing Agent: Seeme Moreira from Listing Office: Coldwell Banker Realty - Lexington.
$1,240,000
4 Beds ⋅ 3 Baths ⋅ 73394873 MLS
Unlock the potential of this tri-level home in one of Winchester’s sought-after neighborhoods! Set on a 20,000 sq ft lot, this 4 bed, 2.5 bath, 1966-built home offers 2,116 sf of living space, a 2 car garage, & endless possibilities for renovation or redevelopment. The main level features a formal living room, dining room, & kitchen leading to a deck overlooking the backyard. A cozy family room with fireplace & half bath on the next level. The lowest level offers great space for a guest suite, office, or playroom. Upstairs are four bedrooms & two full baths. While the home awaits cosmetic updates, its strong bones, flexible floor plan, & prime location present a rare opportunity to create something truly special. Enjoy easy access to Winchester’s town center, commuter rail, Vinson Owen School & Wright Locke Farm, all while tucked away on a quiet residential street. Ideal for investors, developers, or end users. Buyers to perform due diligence regarding development or expansion options.

3 Socrates Way, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Advisors Living - Winchester.
$1,820,000
4 Beds ⋅ 4 Baths ⋅ 73385735 MLS
Ideally located in one of Winchester’s most desirable neighborhoods, this classic Colonial blends timeless design with thoughtful updates. At the heart of the home, the beautifully updated kitchen features a generous center island, opening to a spacious family room with a slider leading to a large deck overlooking the expansive, level backyard - perfect for summer entertaining. Just off the kitchen, a well-proportioned dining room flows seamlessly into an oversized living room with a wood-burning fireplace, creating a natural setting for both formal occasions and relaxed gatherings. Upstairs, the serene primary suite offers an en-suite bath and walk-in closet, complemented by three additional bedrooms and an updated full bath. The finished lower level provides versatile space for play, fitness, or a home office. Enjoy close proximity to the vibrant shops and restaurants of downtown Winchester, top-rated schools, major commuting routes, and the Winchester Swim and Tennis Club.

109 Thornberry Rd, Winchester

Listing courtesy of Listing Agent: Andrew Martini from Listing Office: Compass.
$2,700,000
5 Beds ⋅ 5 Baths ⋅ 73404798 MLS
Welcome to this truly distinctive home nestled on a lush landscaped lot in historic & highly sought after Rangeley Estates neighborhood. Just moments from downtown Winchester, this hidden gem offers a unique blend of privacy and convenience! This stunning home boasts 5 bedrooms & 4 full baths, seamlessly blending original charm with modern amenities. Step inside to discover sun-filled rooms and a thoughtfully designed floor plan, featuring a family room addition off the updated kitchen, formal dining and living rooms and a sun room w/walls of windows overlooking the gorgeous grounds. 3 spacious bedrooms on the second floor with 2 tastefully updated baths including the primary. The 3rd floor includes 3 rooms, 2 bedrooms, a home office and full bath. The level lot & mature landscape provide a serene backyard oasis. The property includes free standing two-car garage, large driveway & patio. This home is a rare gem that offers an unparalleled living experience with its prime location!

34 Rangeley Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,175,000
4 Beds ⋅ 3 Baths ⋅ 73384584 MLS
Charming multi-level home in close proximity to Winchester Center, public transit, Lincoln Elementary, and McCall. The main level offers an open floor plan with beautiful hardwood floors, bay windows, a skylit eat-in kitchen, and abundant natural light. Perfect for entertaining, the living and dining rooms flow seamlessly to a spacious yard, relaxing patio, and mature gardens. The top floor includes 3 generously sized bedrooms and 2 baths, including a primary suite with walk-in closet and private bath. A few steps down, enjoy a cozy family room, additional bedroom, mudroom, laundry, and half bath. A truly move-in ready home in a prime location!

163 Main St, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$3,000
2 Beds ⋅ 1 Baths ⋅ 73413482 MLS
(No Broker Fee Needed) 2-Bedroom apartment in a desirable Winchester neighborhood for rent. Situated at a quiet street, this two-bedroom and one-bathroom in a two-family house setting has a nice floor plan and decent flow. Hardwood floor throughout. It has a spacious eat-in kitchen with a pantry and with stainless appliances, granite counter tops and a side door that leads to the big and bright backyard. Two bright generous bedrooms are with high ceiling and fans. Features also include front porch, storage shed, and large flat backyard. Full basement provides tons of storage space. Great opportunity to move into Winchester and take advantage of the great schools, cozy community and close proximity to Boston. Two off-street parking are included. Very convenient location and close to Winchester Town Center, schools, shopping and Rt. 93 and 95.

38-40 Florence Street Unit 40, Winchester

Listing courtesy of Listing Agent: WINN Rental Team from Listing Office: WINN Real Estate & Consulting.
$640,000
2 Beds ⋅ 2 Baths ⋅ 73400097 MLS ⋅ ['Wedge Pond Condominium'] BLDG.
Enjoy the best of Winchester living in this spacious 2-bed, 1.5-bath townhouse at Wedge Pond Condominium, set along scenic Wedge Pond. The main level features hardwood floors, a sunny living room, dining room with charming bow window, half bath, and renovated kitchen with updated appliances. Upstairs offers two bedrooms and a full bath. The finished lower level provides flexible space for a family room, home office, or guest bedroom, plus laundry and storage. Large closets throughout offer ample storage. Extend your living outdoors with garden views and a serene pondside setting. One deeded parking space included. Unbeatable location—walk to downtown shops, Packer Tennis Courts, new Lynch School, McCall, WHS, commuter rail, and Tri-Community Bike Path. Easy access to 95 and 93. A great fit for a variety of lifestyles, low-maintenance home, offering comfort, flexibility, and a prime location.

60 Lake St Unit I, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Advisors Living - Winchester.
$790,001
3 Beds ⋅ 2 Baths ⋅ 73392883 MLS
Looking for the ideal first home or a peaceful place to settle into your next chapter? This charming 3-bedroom, 2-bath home, nestled at the end of a quiet dead-end street, was completely remodeled in 2009. Step inside to a warm and welcoming space with a practical layout—everything you need without the fuss. Whether you're just getting started or looking to simplify, this move-in-ready home is a smart and comfortable choice. This home features hardwood floors, kitchen with granite countertops and stainless steel appliances, a wonderfully manicured fenced in yard, perfect for gardening. All this just steps away from Mamadou's Artisan Bakery, Swanton Street Diner, Middlesex Fells Reservation and walk to downtown Winchester/Commuter line.

9 Emerson Ct, Winchester

Listing courtesy of Listing Agent: The Serrano Team from Listing Office: Leading Edge Real Estate.

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