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$4,200
2 Beds ⋅ 1 Baths ⋅ 73517313 MLS
DOWNTOWN WINCHESTER! Enjoy this beautiful recently renovated home right outside Winchester center! Direct entry 2 bedroom unit completely updated all new high end 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/ w 10' ceilings/ additional space for family /media room, office plus a large storage room. Garden shed for bike storage & landscape included~ Move right in and enjoy this sweet and highly efficient home ~ enjoy all downtown Winchester has to offer including summer farmers markets, concerts, fairs, restaurants, coffee shops, retail stores & the train to Boston!! You will love living here!

67 Church Unit 67, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,300,000
5 Beds ⋅ 4 Baths ⋅ 73526416 MLS
Welcome to this distinctive home set on a lush landscaped lot in Winchesters historic and highly sought after Rangeley Estates neighborhood. Just moments from the town Center, this hidden gem offers a rare opportunity to renovate, expand & create your dream home in one of the towns premier locations. Rich in character and timeless appeal the sun-filled home features, five bedrooms, 3.5 baths, gleaming hardwood floors, updated electrical, updated heating and a newer roof; beautiful perennial gardens and mature landscape surround the property~ the level backyard is stunning with flowering perennial gardens & specimen trees showcasing the ideal setting. The first floor offers high ceilings, spacious rooms & an oversized screen porch plus sunroom with walls of windows & 2 fireplaces. The second level offers 3 large bedrooms & 2 baths including the primary suite w/ full bath. The third floor offers 2 additional bedrooms & another full bath. Detached 2 car garage and oversized driveway.

30 Rangeley Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,793,000
5 Beds ⋅ 5 Baths ⋅ 73499151 MLS
The most idyllic setting in town! This beautifully renovated and expanded Colonial blends timeless charm with modern sophistication. Perfectly sited on an 18,000 sq ft lot abutting conservation land, it offers exceptional privacy in one of the town’s most coveted neighborhoods. This stunning home features 5+ bedrooms and 4.5 baths, with new windows, updated systems, an expanded kitchen, and beautifully appointed baths throughout. The elegant kitchen overlooks a large, level backyard with direct access to a bluestone patio—ideal for entertaining—set against acres of serene conservation. The second floor offers a gracious primary suite with bath, plus four additional bedrooms and two full baths. The finished lower level features high ceilings, a fireplace, full bath, sauna, and direct yard access.

74 Wedgemere Avenue, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$657,500
3 Beds ⋅ 1 Baths ⋅ 73517006 MLS
This affordable Colonial in the highly sought-after Muraco School district is brimming with potential and ready for your personal vision. An ideal starter home, it features a spacious backyard overlooking Davidson Park, creating a private and peaceful setting. Conveniently located near parks, bike trails, and public transportation, this home offers an exceptional combination of value, location, and opportunity. Whether you're a contractor, investor, or homeowner looking to build equity, this diamond in the rough is full of possibilities.

55 Brookside Ave., Winchester

Listing courtesy of Listing Agent: Michael Rauseo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$2,650,000
5 Beds ⋅ 4 Baths ⋅ 73506730 MLS
Exquisite home nestled in sought after Winchester neighborhood! This breathtaking home checks all the boxes on the wish list! Welcoming sun-filled entry foyer, soaring ceilings, gleaming hardwood floors & open concept flow. Inviting living room w/gas fireplace. Fabulous gourmet kitchen complete w/ Viking appliances, walk-in-pantry, dining area, coffee/wet bar & wine chiller. Sliding doors open to deck w/ serene wooded views overlooking level fenced in backyard. Elegant dining room, Family room w/stone fireplace adjacent to in-law or home office suite w/lush bath & separate entrance. Second floor offers luxurious master suite featuring spa-like marble bath w/oversized shower & soaking tub, dressing room, office nook & private deck retreat. 3 additional generous sized bedrooms w/ensuite baths & laundry room. Lower level features a spacious media/game room that opens to backyard & mudroom w/ direct access to oversized 2 car garage/work space. Highest quality systems & finishes throughout!

21 Bellevue Avenue, Winchester

Listing courtesy of Listing Agent: Giordana Fioravanti Smith from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,280,000
3 Beds ⋅ 2 Baths ⋅ 73522338 MLS
Classic Winchester Gambrel offering charm, space, and an ideal location close to town and the commuter rail. Tucked away on a quaint court shared with just one other home, this 3-bedroom, 2-bath property blends character with comfortable everyday living. The main level features an inviting fireplace living room, large dining room, full bath, beautiful kitchen with eating bar, and spacious family room with excellent potential for a playroom, media room, or au pair setup. The second level includes three bedrooms, an additional office/bonus room, and a second full bath. Additional highlights include basement laundry, 3-car parking, and garage storage. this property offers ample outdoor space for leisure and entertaining. This residence represents a unique opportunity to acquire a home of significance within a desirable Winchester location. A wonderful opportunity to enjoy Winchester living close to shops, restaurants, and commuting routes.

2 Eaton Ct, Winchester

Listing courtesy of Listing Agent: Robert Ellington from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$4,800
2 Beds ⋅ 3 Baths ⋅ 73530776 MLS
Don't miss this opportunity to lease a beautifully appointed 2-bedroom, 2.5-bath townhome-style condo in the sought-after White Horse Commons community. Spanning 1,560sqft, this home features gleaming hardwood floors, a warm fireplace, and an abundance of natural light. The open kitchen offers generous counter and cabinet space, while in-unit washer/dryer, central A/C, and a full appliance suite make everyday living effortless. The partially finished lower level provides excellent flex space — perfect for a home office or gym. Enjoy private outdoor living on your deck, ideal for warm-weather entertaining. Set in one of Winchester's most coveted neighborhoods, you're moments from the charming boutiques, restaurants, and vibrant energy of Winchester Center — one of Greater Boston's most desirable suburban towns. Easy access to Routes 3 & 93 and the Winchester MBTA Commuter Rail, with the beauty of the Middlesex Fells Reservation right at your doorstep.

22 Grove Pl Unit 6, Winchester

Listing courtesy of Listing Agent: The McLaren Team from Listing Office: Compass.
$2,600,000
6 Beds ⋅ 5 Baths ⋅ 73516849 MLS
Timeless 1920 brick Tudor in the heart of the Flats neighborhood combines all of today’s modern amenities with classic architectural charm to create an exceptional home for modern living offering 6 bedrooms, 3 full and 2 half baths. A welcoming entry opens to a sun-filled living room with custom built-ins, fireplace, and French doors to a private office. The open dining room flows into a chef’s kitchen with oversized island, abundant storage, and adjoining family room ideal for everyday living and entertaining. A custom mudroom, walk-in pantry, and half bath complete the first floor. The primary suite offers ensuite bath and walk in closet. 3 additional bedrooms, a full bath and convenient laundry room complete the second floor. The third floor offers two additional bedrooms, a full bath and ample storage. The finished lower level includes recreation, gym, playroom space, half bath, second laundry room and unfinished storage. Manicured grounds, two-car garage, C/A and irrigation.

47 Yale Street, Winchester

Listing courtesy of Listing Agent: Molly Nolan Byrne from Listing Office: Coldwell Banker Realty - Belmont.
$5,500
4 Beds ⋅ 3 Baths ⋅ 73512558 MLS
Spacious 4-bedroom, 2.5-bath townhouse ideally located within walking distance to the town center, schools, and commuter rail. This well-maintained home features beautiful hardwood flooring throughout, a bright and functional layout, and generous living space perfect for everyday living and entertaining. Enjoy outdoor living with a private deck and a fenced-in yard. Additional highlights include a two-car garage and ample storage. Conveniently situated for easy access to shopping, dining, and transportation, this home offers comfort, space, and an unbeatable location.

44 Spruce Unit 2, Winchester

Listing courtesy of Listing Agent: Dylan Archambault from Listing Office: Archambault Real Estate.
$3,100,000
6 Beds ⋅ 6 Baths ⋅ 73468691 MLS
This exceptional Everett Avenue residence stands among the street’s most distinguished offerings, commanding a premier setting on over half an acre. Renovated in 2023-2025, timeless architecture is seamlessly married to today’s most coveted amenities. Hallmark architectural details abound. Balusters, soaring ceilings, coffered rooms, original crown moldings, mantels, and decorative trim are beautifully preserved, elevated by the warm glow of restored hardwood floors. Generous, light-filled rooms unfold with grace and scale throughout. A newly designed chef's kitchen, new baths, walk-in pantry w/laundry and a classic butler’s pantry with wine refrigerator are some of the highlights. Anchoring the home is an expansive family room, framed by floor-to-ceiling windows overlooking a park-like lawn. A rare offering where architectural pedigree, thoughtful architecture and renovation, and exceptional land converge.

27 Everett Ave, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
$2,150,000
5 Beds ⋅ 4 Baths ⋅ 73527768 MLS
OFFER DEADLINE TUESDAY JUNE 9, 12PM. Beautifully appointed 5BR, 2 full/2 half bath home with 3,136 sq ft of thoughtfully designed living space on a flat, fully fenced .34 acre lot. Renovated kitchen with quartz countertops and luxury appliances. Expansive and bright living room with custom built-ins, window seating, and gas fireplace. The main living level also offers 3 spacious bedrooms and a serene primary suite with a walk-in closet and private en suite bath. Fully refreshed entry-level offers another bedroom, includes a custom mudroom off the 2-car attached garage, half bath, and laundry room. Completed with an oversized media room with walkout access. Generous, manicured yard with expanded patio--perfect for everyday living and entertaining outdoors. New systems, flexible layout, abundant natural light, and thoughtful updates throughout. Extra outdoor storage with included shed. Minutes from the Middlesex Fells Reservation, top-rated schools, and vibrant downtown Winchester.

22 Hollywood Rd, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$5,500
4 Beds ⋅ 3 Baths ⋅ 73502072 MLS
Spacious 4-bedroom, 2.5-bath townhouse ideally located within walking distance to the town center, schools, and commuter rail. This well-maintained home features beautiful hardwood flooring throughout, a bright and functional layout, and generous living space perfect for everyday living and entertaining. Enjoy outdoor living with a private deck and a fenced-in yard. Additional highlights include a two-car garage and ample storage. Conveniently situated for easy access to shopping, dining, and transportation, this home offers comfort, space, and an unbeatable location.

42 Spruce Unit 1, Winchester

Listing courtesy of Listing Agent: Dylan Archambault from Listing Office: Archambault Real Estate.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.
$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.

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