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$950,000
2 Beds ⋅ 2 Baths ⋅ 73386306 MLS ⋅ ['6-8 Francis Circuit Condominium Trust'] BLDG.
Submerge yourself in historic elegance in this meticulously detailed Victorian home, brimming with classic design. Located on one of Winchester’s most serene and desirable cul-de-sacs, this stunning gem overflows with rich architectural details. Inside, you'll find three stately fireplaces, two oversized pocket doors, exquisite antique leaded light fixtures, stained glass, gleaming hardwood floors, soaring ceilings, and sun-drenched rooms with grand windows throughout. The unique layout features handsome fireplaces in both living and dining rooms, a charming updated kitchen, 2 en-suite bedrooms (another fireplace!), a private office, and laundry room. Enjoy a chat with a friend on the spacious front porch or dinner al fresco on the secluded patio, surrounded by gorgeous gardens. The detached garage has room for a car and storage. A short stroll to Winchester's award-winning schools, the quintessential downtown, boutiques, eateries, commuter rail, the Fells, and more.

6 Francis Circuit Unit 6, Winchester

Listing courtesy of Listing Agent: Katherine Waters Clark from Listing Office: Compass.
$680,000
2 Beds ⋅ 2 Baths ⋅ 73381805 MLS ⋅ ['The Willows'] BLDG.
Fantastic opportunity to own a freshly updated 2 bed 2 bath condo in Winchester—one of Massachusetts’ top-rated school districts. Located in the desirable Lynch Elementary district, which will open a brand-new school building this fall. This move-in ready home has just been freshly painted, with brand-new kitchen appliances and new carpeting throughout. The open-concept living and dining area connects to a private balcony facing the interior courtyard. The spacious primary suite features a walk-in closet and en-suite bath. A second bedroom and full bath provide flexibility for guests, family, or home office use. Additional highlights include in-unit laundry and two outdoor parking spaces. The community offers fantastic amenities, including a fitness center, clubhouse with event space, and a beautiful outdoor pool—perfect for summer. A rare combination of location, schools, and lifestyle!

7 Conant Rd Unit 23, Winchester

Listing courtesy of Listing Agent: Xin Cui from Listing Office: Hooli Homes Boston.
$1,280,000
5 Beds ⋅ 4 Baths ⋅ 73374220 MLS
This COMPLETEDLY GUTTED AND REBUILT IN 2015 5B3.5B colonia-preserving a portion of original foundation, is located in a quiet neighborhood yet just minutes to Town Center, Elementary & High School, Town beach, Horn Pond, Fells Reservation, commuter rail station/Bus 134 to Wellington T. The architect-designed home features hardwood flooring throughout, high ceiling & abundant natural light. 1st floor offers a spacious LR with side exit & open-concept kitchen/dining area with elegant white cabinetry, granite countertops, Kenmore Pro Series SS appliances & adjacent laundry area with a half bath. Upstairs, primary suite boasts a walk-in closet & a stylish en suite bath. Two extra well-sized bed share 2nd full bath. 3rd floor provides a generous family recreation area with vaulted ceiling, 2 more bed perfect for guest rooms or home offices & another full bath. Unfinished basement provides ample storage/expansion. Cute garden area at back yard. Enjoy easy commute to Boston or Cambridge.

18 Hemingway St.,, Winchester

Listing courtesy of Listing Agent: Julia and Joanne (Guozhen) Team from Listing Office: Keller Williams Realty-Merrimack.
$3,600
3 Beds ⋅ 2 Baths ⋅ 73398993 MLS
(All is just repainted, brand new kitchen floor and countertops - Ready to rent out) 3-Bed / 2 Full-bath apartment in a desirable Winchester neighborhood for rent. Situated at a quiet street, this three-bedroom and two-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. Two bright generous bedrooms are with high ceiling and fans on the second floor. One big bedroom with a full bath and a fridge is on the third floor. Features also include front enclosed 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 2, Winchester

Listing courtesy of Listing Agent: WINN Rental Team from Listing Office: WINN Real Estate & Consulting.
$1,226,000
3 Beds ⋅ 3 Baths ⋅ 73382207 MLS
Tucked into the desirable Winchester Highlands and abutting the Middlesex Fells, 8 Ware Road offers space, comfort, and a flexible footprint. This well-maintained ranch features 3 bedrooms on the main level, including a primary suite with full bath, plus a finished basement with a spacious family room, walk-out sliding patio door, large flex space, & bonus 4th bedroom. The kitchen includes modern cherry cabinets, and hardwood floors run throughout much of the main level. Two fireplaces add charm, and the finished lower level spans the full footprint of the house. With 3 full bathrooms, updated heating, 2024 central air, a large deck, and patio, this home is move-in ready with room to grow. Enjoy the peace of a wooded setting with quick access to I-93 and downtown Winchester. A rare chance to own a versatile home in one of Winchester’s most sought-after neighborhoods. Open for tours Saturday & Sunday, 11:30–1:30pm.

8 Ware Rd, Winchester

Listing courtesy of Listing Agent: Alex Navarro from Listing Office: Coldwell Banker Realty - Beverly.
$1,115,000
3 Beds ⋅ 2 Baths ⋅ 73382039 MLS
Welcome to 48 Winford Way, a three bed, two bath Cape on a lovely level lot with a family room addition and a garage. A perfect starter home or downsizer with a full bath on each floor. Living room with large windows and a fireplace, dining room with an impressive chandelier and built-in china cabinet, eat-in kitchen with quartz countertops, tiled backsplash, and pantry closet. First floor family room with a view of and slider to a stone patio and the beautiful back yard. First floor bedroom is a pass-through and is currently used as an office. First and second floor bathrooms are tiled with tub and shower. On the second floor, the primary bedroom is spacious and easily fits a king bed, while the second upstairs bedroom has eaves storage access on both sides. Updated windows, Buderus heating system, sprinkler system, hardwood floors, and a full basement to finish or use for storage. All this just over a mile to Wedgemere train station. Enjoy all that Winchester has to offer!

48 Winford Way, Winchester

Listing courtesy of Listing Agent: Rebecca Brennan from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,280,000
4 Beds ⋅ 2 Baths ⋅ 73380011 MLS
Don't miss your opportunity to own on Canterbury Road! This sun-drenched, 4-bedroom home with hardwood flooring offers an open and classic layout. Enjoy the spacious living room with built-ins, four, second floor bedrooms, and an expansive .37 acre lot. The versatile family room provides flexible space for a home office, playroom, or guest space! Imagine evenings on the covered porch or patio, taking in sunsets and seasonal Mystic Lake views. This well-preserved home awaits your personal touches. With an unfinished full basement and attic, there's plenty of room for growth, storage and potential. Winchester town center and West Medford village are each a pleasant, single mile away. Enjoy the restaurants, parks, shops and 3 convenient Commuter Rail stations for a quick 14-minute train ride to Boston. Welcome Home!

25 Canterbury Road, Winchester

Listing courtesy of Listing Agent: Lynne Russo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,551,000
3 Beds ⋅ 5 Baths ⋅ 73375416 MLS ⋅ ['The Ledges'] BLDG.
Welcome to The Ledges, Winchester’s premier townhouse community! This extraordinary F Style corner unit is truly one of a kind with soaring ceilings, sun-filled spaces, and rare flat backyard space with two decks. A landscaped courtyard leads to a gracious foyer and transitions into an expansive open layout. The chef’s kitchen opens to the dining rm and features ss appliances, granite countertops and a raised bar for casual seating. The living room, framed by gorgeous atrium windows, centers around a striking double-sided gas fireplace + wet bar, connecting to the adjacent family room. Built-ins add warmth and function, while glass sliders extend the living space outdoors. The primary suite offers a sitting room with fireplace, two walk-in closets, and a spa-like bath. A second en-suite overlooks the front garden, while an upstairs third suite is ideal for guests or a home office. Lower level includes two finished rooms, a full bath, and additional unfinished space for future expansion

7 Wainwright Road Unit 13, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Advisors Living - Winchester.
$1,390,000
4 Beds ⋅ 3 Baths ⋅ 73367556 MLS
Set on a generous, beautifully landscaped lot, this meticulously maintained home showcases numerous recent upgrades, and offers both comfort and style. The newly renovated kitchen features upscale appliances and custom quartz countertops, perfect for everyday living and entertaining alike.Hardwood floors, two fireplaces, a sunlit living room, and a separate family room create inviting spaces throughout. Newer windows and doors enhance natural light, while the elegant dining room opens to a large porch that overlooks the expansive, fenced backyard, ideal for gatherings and outdoor enjoyment. The home is conveniently located near Wright-Locke Farm, Mullen Field, Winchester Country Club, and Vinson-Owen School. It also offers easy access to public transportation, including Alewife Station and 20 minutes to downtown Boston.

26 Ridge St, Winchester

Listing courtesy of Listing Agent: Dream Team from Listing Office: Dreamega International Realty LLC.
$2,200,000
4 Beds ⋅ 4 Baths ⋅ 73381978 MLS
NEWER CONSTRUCTION 4 bed 3.5 bath colonial located in a great neighborhood right outside Winchester center! Enjoy all the area has to offer just outside your door including restaurants, shops, schools, train to Boston, the Tri-Community bike path, Horn Pond, Packer tennis courts & Wedge pond! This warm and welcoming, gently lived in home showcases 3900sf of space on 3 levels with 4 large bedrooms, 3.5 baths, 2nd floor laundry & 2 car garage. Thoughtfully crafted by top local builder w/ high ceilings, hardwood floors & an open floor plan featuring a spacious kitchen w/center island, custom cabinetry & stainless appliances leading to dining room & family room w/ wall of sliders out to great patio & yard. Upstairs you'll find 4 spacious bedrooms, including the primary suite w/ 2 walk-in closets and a beautiful en-suite bath w/ oversized shower & double vanity sinks. The finished lower level offers a large media/playroom plus storage. A direct entry two-car garage completes this home

4 Fairfield Pl, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,160,000
4 Beds ⋅ 4 Baths ⋅ 73374158 MLS
Ideally located in a very desirable neighborhood that abuts the town forest and surrounded by cul-de-sacs, this elegant well-designed 4-bedroom, 3.5-bathroom colonial home has been meticulously maintained by the original owners and features a spacious layout with ample room for comfortable living. The floorplan is thoughtfully designed, with a nice flow from one room to the next. The family room showcases vaulted ceilings with skylights, enhancing the abundant natural light and the sense of openness and volume. Each of the four bedrooms provides a generous amount of space; especially the serene primary bedroom ensuite with a walk-in closet. The finished lower level allows for additional living space, perfect for a home gym and recreation area. Stepping outside, the oversized deck offers a tranquil setting for relaxing, enjoying meals and entertaining. The home's location on a dead-end street, provides a peaceful setting. Walk to Wedgemere Station and Winchester Center. A MUST-SEE!

19 Sussex Rd, Winchester

Listing courtesy of Listing Agent: Ida M. Bianco from Listing Office: Coldwell Banker Realty - Lexington.
$4,300
2 Beds ⋅ 1 Baths ⋅ 73368860 MLS
Enjoy this beautiful renovated home right outside Winchester center! Direct entry unit completely updated all new with gorgeous kitchen & bath, hardwood floors, new heating system with central air, new windows, electric, very high ceilings, washer & dryer in unit, 2 car parking driveway in rear, exclusive patio area great for grilling! beautifully finished lower level offers a large room/ additional space for family /media room, plus storage room. garden shed & landscape included~ Move right in and enjoy this sweet and highly efficient home and enjoy all downtown Winchester has to offer including restaurants, coffee shops, retail stores & the train to Boston!!

67 Church Unit 67, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,400,000
3 Beds ⋅ 3 Baths ⋅ 73368856 MLS
Discover this stunning, flats location ~ fully gut-renovated 3-bedroom, 2.5 bath home~ perfectly situated close to downtown Winchester! With its breathtaking design, this residence boasts a thoughtful layout; the open-concept first floor has high ceilings and an abundance of natural light. The thoughtfully selected finishes, tiles, and fixtures add a touch of elegance and sophistication throughout. The stunning kitchen features a dining island & gas cooking. You will love the space this home has between the large bedrooms, spacious baths and the walkout lower level. A nice patio and yard await outside. Enjoy the convenience of being just steps away from Winchester center where you will find the commuter rail train, great restaurants, shops, the library, parks & more! Only 7 miles from Boston, this home an ideal location for commuters. Experience the perfect blend of suburban tranquility and urban accessibility.. Don’t miss the opportunity to call this beautiful property your new home!

20 Fletcher Street Unit 20, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,500,000
5 Beds ⋅ 4 Baths ⋅ 73365882 MLS
Classic architecture meets modern luxury in this Royal Barry Wills Colonial on an oversized lot in Winchester’s beautiful Flats neighborhood. This meticulously renovated 5-bedroom home features a chef's kitchen with custom cabinetry, granite surfaces, center island, beverage cooler & built-in china cabinet. Natural light floods the expansive family room, featuring custom built-ins & oversized windows framing views of the large Azek deck & backyard. A living room with fireplace, elegant dining room & large mudroom with built-ins and half bath complete this level.The primary suite offers a private retreat with soaring cathedral ceilings, dual closets & a luxurious bath with an oversized tiled shower. 4 additional bedrooms, including one en-suite, plus a marble-appointed hall bath complete the second floor. The lower level offers a fireplaced recreation room, fitness space & storage. A 2-car attached garage on a picturesque, tree-lined street near the newly built Lynch Elementary School.

17 Harrison Street, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,675,000
3 Beds ⋅ 4 Baths ⋅ 73386110 MLS ⋅ ['The Ledges'] BLDG.
Welcome to The Ledges—an exceptional custom-designed “E” style end-unit townhouse offering over 10 rooms of refined living space and a distinctive layout found in no other unit. Thoughtfully maintained and tastefully updated, this residence features an expansive open floor plan with cathedral ceilings, elegant crown molding, and a gourmet chef’s kitchen equipped with premium appliances. The first floor includes formal living and dining rooms, a built-in office, and a luxurious primary suite with dual walk-in closets, a spa-like bath, and direct access to a private deck overlooking a tranquil wooded setting. The second level offers a spacious bedroom, full bath, and additional office or flex space. The fully finished walk-out lower level, complete with custom built-ins and access to a serene, tree-lined common outdoor area, provides the ideal space for guests/extended family. Located near the clubhouse, pool, and tennis courts, with convenient access to Winchester Center & major routes!

7 Wainwright Road Unit 55, Winchester

Listing courtesy of Listing Agent: Ngoc Anh Goldstein from Listing Office: Leading Edge Real Estate.
$1,635,000
4 Beds ⋅ 3 Baths ⋅ 73384904 MLS ⋅ ['35 & 37 Rumford Street Condominium'] BLDG.
This sun-filled 2012 townhouse, with its spacious layout, backyard oasis & attached garage, lives like a single-family home. Spend weekends lounging on the private deck, unwinding under the pergola, or playing on the lush, fenced lawn. Inside, the inviting open layout is made for gathering—whether around the gas fireplace on cozy evenings or at the kitchen island while entertaining friends. High ceilings & hardwood floors create an airy, elegant feel, while the porch & backyard invite connection to the outdoors. Retreat upstairs to a tranquil primary suite w/spa-like bath or escape to the skylit top-floor office or family room. The roomy basement offers space to dream-whether a home gym, playroom, or creative studio. Tucked in a welcoming neighborhood just ½ mile to the new Lynch School (opening Fall 2025), and located close to Winchester HS, shopping & eateries, Winchester Center & commuter rail (20 mins to Boston), this home offers the perfect blend of comfort, privacy, & convenience

35 Rumford St Unit 35, Winchester

Listing courtesy of Listing Agent: Elena Langlois from Listing Office: Compass.
$1,540,000
4 Beds ⋅ 3 Baths ⋅ 73381093 MLS
This lovingly maintained Colonial home is ideally situated just a 1/2 mile from Vinson-Owen Elementary School. Featuring all 4 bedrooms on the second floor, the layout includes a spacious primary w/ an en-suite bath as well as a fully updated hall bath. The main level offers an elegant family room w/ soaring ceilings, a cozy fireplace, recessed lighting & a slider leading to the deck. The adjacent eat-in area flows seamlessly into a beautifully appointed kitchen with quartz counters, stainless steel appliances, a stylish tile backsplash & recessed lighting. A separate formal dining room & generously sized living room—complete w/ HW floors & a second fireplace—provide ample space for entertaining. The partially finished lower level offers a versatile bonus space w/ walk-out access to a new patio & fully enclosed backyard. Set on a picturesque 1/2-acre lot adorned w/ perennials, this home offers the perfect blend of comfort, convenience & charm-an exceptional opportunity in Winchester!

21 Johnson Rd, Winchester

Listing courtesy of Listing Agent: Stefanie Clifford from Listing Office: Keller Williams Realty Boston Northwest.
$1,050,000
4 Beds ⋅ 2 Baths ⋅ 73353927 MLS
Welcome to this oversized Cape in a lovely west side neighborhood of Winchester. Opportunity for a little TLC or a significant renovation, the flexible layout of this 1952 gem offers many possibilities. Attention savvy buyers, contractors and builders! Sited on a 10,703sf lot within the Vinson-Owen school district. First floor offers living room, dining room, kitchen, sunroom/porch, 2 bedrooms and a bath. Second floor has 2 large bedrooms and a full bath. Family room and laundry are in the walk-out lower level. 2-car garage under. Great location for commuting to Rt 2, Rt 3, 128, 93 and the Commuter Rail. Sold AS-IS. Buyers please do your own due diligence. Seller and Seller’s agent make no warranties or representations. This property offers TREMENDOUS OPPORTUNITY to make your forever home. Sellers prefer closing at end of June.

61 Westland Avenue, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,924,000
4 Beds ⋅ 4 Baths ⋅ 73384193 MLS
Rare opportunity on a peaceful cul-de-sac. This extraordinary 4-bedroom, 4-bathroom home is nestled in one of Winchester's most sought-after neighborhoods. For the first time ever, this meticulously maintained residence is available on a street where properties rarely change hands. Bathed in abundant natural light, the thoughtfully designed floor plan showcases generously sized living spaces that flow seamlessly from room to room. Each of the 4 bedrooms offers scale and closet space; the primary is large enough for a full sitting area and boasts 2 walk-in closets. The family room offers a wall of windows with sliding glass doors and a gas fireplace which flows into the oversized kitchen, with a full dining area and an attached deck. The formal dining room and living room offer more entertaining options, & the enormous windowed and walk-out basement is ideal for a rec-room, gym or yoga studio. Storage galore, upstairs laundry, an oversized two car garage, all in pristine condition!

5 Hastings Rd, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Advisors Living - Winchester.
$1,430,000
6 Beds ⋅ 3 Baths ⋅ 73332625 MLS
Perfectly situated just moments from the vibrant heart of Winchester, this Mansard-roofed beauty offers a harmonious blend of refined style and comfort. A spacious front porch overlooking a sizable side yard invites you to relax and enjoy the energy of the nearby town center. Inside, the main level blends form and function; expansive living spaces are complemented by a mudroom, home office, and half bath, all centered around a kitchen and family room with a fireplace designed for gathering. Upstairs, generous bedrooms span two floors, including a private suite with its own staircase—ideal for added privacy or a future primary. Treasured by past owners who found it the perfect place to grow and gather, this unique home exudes character inside and out. A truly special offering, ready to support your next move and future vision.

189 Mystic Valley Pkwy, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
$3,000
2 Beds ⋅ 2 Baths ⋅ 73397002 MLS
Move in ready 6 rooms, 2 beds, 1.5 baths townhouse in a Duplex AVAILABLE NOW! Set in the desirable west side of Winchester. Family Room in lower level with a space that can be used in many ways with brand new carpet. Hardwood floors throughout main levels. Two large bedrooms on the second floor including a primary with a walk in closet and a secondary closet. Sizable storage space and exclusive use washer and dryer. Landscaped private yard with patio, perfect for relaxing and entertaining. Minutes from Winchester Center with 2 MBTA Stations to Boston, restaurants and dining. Located in the Vinson Owen School district within Winchester's top rated schools. Off street parking for 4+ cars. No pets and no smoking. Rent includes Water, Sewerage. Tenant responsible for Oil, Electric, bringing refuse to transfer station and snow removal.

7 Ridge St Unit 7, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.
$2,200,000
6 Beds ⋅ 4 Baths ⋅ 73376080 MLS
Nestled in the highly sought-after "heart" of Winchester Center, this Newer Construction single-family (slightly attached) home offers space & finishes you typically find in 2.5M+ homes! With 10' ceilings and high end finishes throughout, this stunning 5-6 bedroom, 3.5 bath home is just two blocks from the vibrant town center, train station, schools, restaurants & shops! 5190 total sf w/ 3900sf above grade PLUS 1289sf in BSMT can be finished. The first floor features a bright, welcoming kitchen, a gorgeous dining room & stunning family room, along w/ mudroom, walk in pantry & 1/2 bath. On the second floor, you'll find a luxurious primary suite complete with two walk-in closets, laundry & full bath plus 2 or 3 additional bedrooms, including a versatile bonus room w/ soaring ceilings & separate entrance..ideal for extended family or guests. The third floor adds more space with two additional large bedrooms and a full bath. NEW 32k Solar panel system supplies almost all power for the home

20 Elm Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$3,000
2 Beds ⋅ 1 Baths ⋅ 73398442 MLS
Available for 8/1 move-in! Enjoy the best of in-town living with this charming two-story rental, just a short walk to downtown Winchester, commuter rail, library, restaurants, coffee shops & the scenic trails of the Fells. Bursting with character, this home features classic moldings, soaring ceilings, & gleaming hardwood floors. Enjoy the convenience of your own private entrance, a beautifully renovated kitchen & bathroom, & ductless mini-splits for efficient summer cooling. The shared outdoor space includes a fenced backyard and patio with BBQ area. Generous basement storage & in-unit laundry. Two off-street parking spaces in the driveway as well!

189 Washington St Unit 3, Winchester

Listing courtesy of Listing Agent: Paul Hryb from Listing Office: Maloney Properties, Inc..
$4,200
3 Beds ⋅ 2 Baths ⋅ 73397975 MLS
Beautifully Updated Home in Winchester Muraco School District! Welcome to this charming and sun-filled home tucked away on a quiet cul-de-sac, set on over half an acre of fully fenced land. Located in one of Winchester’s most desirable neighborhoods and within the top-rated Muraco School District, this home offers the ideal blend of comfort, space, and location. Inside, enjoy a bright, open layout with brand-new hardwood floors, renovated bathrooms, and a new deck—perfect for relaxing or hosting guests. The spacious kitchen features polished granite countertops and stainless steel appliances, while energy-efficient Andersen windows fill the home with natural light throughout. Upstairs, hardwood floors extend across generously sized bedrooms, and the finished walk-out basement, complete with a cedar closet, adds extra space not included in the official living area. Don’t miss this rare rental opportunity in one of Winchester’s most sought-after areas!

30 Bellevue Ave Unit 30, Winchester

Listing courtesy of Listing Agent: Nancy Zhang Zhenning from Listing Office: Fairview Partners International LLC.
$2,350
1 Beds ⋅ 1 Baths ⋅ 73387388 MLS
Immaculate, king-sized, 1 bedroom apartment on top floor of brick building just steps to Winchester Center and Commuter Rail. Heat and hot water included. Dishwasher /disposal, over-the-stove microwave, newly carpeted, central A/C and 1 car, assigned garage parking spot with automatic door opener. Laundry in building. Storage unit included. Available now or July-September 1st. No pets/no smoking.

35 Vine Street Unit 401, Winchester

Listing courtesy of Listing Agent: Jill Shanley from Listing Office: CJL Rentals & Property Management Co., Inc..
$3,295
2 Beds ⋅ 2 Baths ⋅ 73380505 MLS
LOCATION! LOCATION! LOCATION! Enjoy the tranquil beauty and gorgeous views! Sit on the patio and watch the swans float by. Walk to public transportation including the commuter rail to Boston. Easy access to all major routes. Shop the downtown boutiques and dine in the some truly great restaurants. Hardwood floors throughout (except kitchen and bathrooms) and a finished family room in the basement. 2 bedrooms, 1.5 baths, plenty of storage and in-unit laundry. Just steps to the beach, tennis courts, farmers market and the downtown shops. Deeded parking at your door. Electric baseboard heat - 6 zones, Come see all that Winchester offers besides its fabulous schools. Whether you are downsizing or first time buyers - this has everything you are looking for. Trash/recycling picked up at your door 3 times a week. Mail delivered to your door

50 Lake Street Unit O, Winchester

Listing courtesy of Listing Agent: Sheri O'Connor from Listing Office: Plunkett Properties.
$4,300
2 Beds ⋅ 3 Baths ⋅ 73371815 MLS
Much sought after location! Sun filled, 2 bed, 2.5 bath condo in the former Wyman School. This lovely slate roofed, brick, elevator building has generous, well-appointed hallways. When you enter the apartment, you’ll be wowed by a living room with 12’ ceilings, huge windows with custom insulated blinds and French doors that open to a Juliet balcony. Lovely woodworking is seen in the deep crown molding and custom cabinets, gas fireplace. Adjacent kitchen/dining room and half bath. Great entertaining floor plan. A handsome staircase leads to the upper level, which boasts a King sized en-suite with hardwood floors, great light, recently renovated main bath, and a walk-in closet. The laundry is on the 2nd level! The guest BR has a large closet, skylite and it's own private bath. Hardwood floors everywhere except the baths. Beautifully manicured grounds. 1 car garage plus an extra parking space. Large storage cage in basement. Walk to Winchester restaurants, shops and train to Boston.

83 Church Unit 9, Winchester

Listing courtesy of Listing Agent: Diane Plunkett from Listing Office: Plunkett Properties.
$2,800
2 Beds ⋅ 1 Baths ⋅ 73370561 MLS
1ST FLOOR! REMODELED 2 Bedroom apartment in 2 family boasts beautifully restored hardwood floors, high celings and great versitile floor plan. Beautiful full bath, fully applianced kitchen featuring ceramic tile floors and quartz countertops. 2 Car off street parking available, plus exclusive use of back porch. Common use of backyard can include use of grill and gardening as well. Prime location just 1 mile from Winchester Hospital, and less than 1 mile to DOWNTOWN WINCHESTER featuring fantastic resturants and shops. Within close proximity to major traveling routes. Rent includes basic cable and internet!

13 Oak Street Unit 1, Winchester

Listing courtesy of Listing Agent: Chuha & Scouten Team from Listing Office: Leading Edge Real Estate.
$8,000
5 Beds ⋅ 4 Baths ⋅ 73345673 MLS
Walk to town and schools from this spacious 11 room, 5 bedroom, 3.5 bath home! Open floor plan and high ceilings. Bonus rooms/ home office space. Delightful and bright sun porch. New kitchen with classic white cabinetry and quartz countertops. Two car attached garage and mud room. New heating and central air. Ample off street parking. Available July 1, 2025

271 Washington Unit 1, Winchester

Listing courtesy of Listing Agent: Julia Marino from Listing Office: Archambault Real Estate.
$2,100
1 Beds ⋅ 1 Baths ⋅ 73384063 MLS
Bright and sunny 1 bedroom and 1 bathroom condo in Winchester Park View. close to shopping, restaurants, town Center and walking to commuter train. Easy access to all major highways. Rental fee Including heat, electricity, hot water and a lot of more... Available 06/01.

200 Swanton St Unit 428, Winchester

Listing courtesy of Listing Agent: Wei Wang from Listing Office: WW Real Estate LLC.

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