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20 Amberwood Dr, Winchester
$15,000
6 Beds ⋅ 7 Baths ⋅ 73496587 MLS
New construction 6 bedrooms and 7 full baths, 2 Car garage. Located in a highly desirable neighborhood just steps from VO Elementary School. The expansive 1st floor welcomes you with soaring ceilings and an elegant layout, including a sophisticated living room, family room, and private home office. The chef’s kitchen is a true centerpiece, boasting premium Thermador appliances, custom cabinetry, and a large island that flows seamlessly to an oversized deck—perfect for entertaining or relaxing. Upstairs, the 2nd floor offers spacious ensuite bedrooms, the luxurious primary suite with a walk-in closet and direct access to a private deck. Additional highlights include a butler’s pantry, mudroom, central air, and a tankless water heater for comfort and efficiency. The finished walkout lower level provides versatile space for a gym, entertainment area, and additional suite.

20 Amberwood Dr, Winchester

Listing courtesy of Listing Agent: Wei Wang from Listing Office: WW Real Estate LLC.
2 Winchester Place Unit 5, Winchester
$1,450
1 Beds ⋅ 1 Baths ⋅ 73543351 MLS
CLEAN 1 BEDROOM APARTMENT LOCATED IN WINCHESTER CENTER. NO WASHER OR DRY IN BUILDING NO SMOKING IN BUILDING GOOD CREDIT AND REFERENCES REQUIRED

2 Winchester Place Unit 5, Winchester

Listing courtesy of Listing Agent: Deborah L. Leavitt from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
21 Willowdale Road, Winchester
$2,170,000
5 Beds ⋅ 4 Baths ⋅ 73534988 MLS
New construction 2019, this impressive 4-5-bedroom, 4.5-bath custom built East side colonial offers exceptional space and a highly sought-after floor plan. The chef's eat-in kitchen features a large center island, abundant cabinetry & sunny dining area that seamlessly blends w/ the spacious family room w built ins & fireplace. Sun-filled living and dining rooms are connected by a double-sided fireplace, creating ideal gathering spaces. The stunning oversized primary includes a beautiful bath w/ shower & soaking tub & large walk-in closet. 3 additional generously sized bedrooms and full bath complete the upper level. The finished lower level offers a media room with a 4th fireplace, a BR/Office, full bath & mudroom area. w/direct access to the garage.Enjoy the large yard and patio, perfect for outdoor entertaining. Conveniently located near Winchester center, parks, & commuter routes, this turn-key home combines modern construction, generous living space, and quality finishes throughout

21 Willowdale Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
63 Dunster Lane, Winchester
$825,000
2 Beds ⋅ 1 Baths ⋅ 73532111 MLS
Bring your vision and your tool box to 63 Dunster Lane! This 1910 bungalow is a 1208 square foot fixer-upper that sits on a 8300 square foot lot. If you're a savvy investor or a contractor/builder this is a great opportunity to completely renovate/rebuild in a highly desirable Winchester neighborhood.

63 Dunster Lane, Winchester

Listing courtesy of Listing Agent: John Ferolito from Listing Office: Keller Williams Realty.
41 Sunset Road, Winchester
$1,700,000
3 Beds ⋅ 2 Baths ⋅ 73520906 MLS
Completely gut renovated in 2023, this stunning home overlooks conservation & offers serene views, privacy & lives like-new construction. The home was thoughtfully redesigned & opened up to feature dramatic soaring vaulted ceilings & an open floor plan, flooded with natural light. The designer kitchen is the centerpiece of the home, showcasing custom cabinetry, paneled appliances, oversized island w/gorgeous natural quartzite countertops, a farmers sink & beautiful details. The wood burning fireplace & wide-plank white oak flooring add warmth. Every space was carefully curated & hand picked, with no detail overlooked. The sunny lower level features a large family room w/ fireplace, full bath, custom laundry room & mudroom. Enjoy a spacious yard & patio perfect for outdoor entertaining & summer dinner parties. Located in a friendly, vibrant neighborhood w/ easy access to town & Boston, this turnkey home offers peaceful surroundings with unmatched convenience. Direct entry 2 car garage.

41 Sunset Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
14 Bradford Rd Unit 14, Winchester
$620,000
3 Beds ⋅ 2 Baths ⋅ 73538704 MLS ⋅ ['Residences At Winchester'] BLDG.
An affordable, 3 bedroom, 1.5 bath townhome at the Residences at Winchester is ready for new owners to make their mark & memories! Located in a quiet neighborhood and part of the new Lynch Elementary School district, this home is part of a duplex and offers an efficient layout and some great perks. Enter to find a large living room with plenty of natural light, which seamlessly flows to the bright kitchen with gleaming black granite counters & a dining area, great for entertaining. Step upstairs to find 3 ample sized bedrooms and a radiant, updated full bath. Hardwood flooring throughout most of the unit, along with energy efficient Harvey windows. Downstairs in the partially finished basement is a sizeable family room, along with storage, and laundry. Enjoy the outdoors in a spacious, flat and private backyard that is maintenance-free because it's covered by the low HOA fee, along with water, sewer & trash removal! Take the opportunity and make Winchester home!

14 Bradford Rd Unit 14, Winchester

Listing courtesy of Listing Agent: Cook Real Estate Partners from Listing Office: Keller Williams Elite.
2 York Road, Winchester
$2,255,000
4 Beds ⋅ 4 Baths ⋅ 73537657 MLS
Move right into this beautifully updated Colonial set on a level, fenced corner lot. Designed for modern living, this 4-bedroom, 3.5-bath home offers a spacious floor plan with a warm, nature-inspired aesthetic throughout. The inviting family room impresses with a dramatic beamed ceiling, while the primary suite features a cathedral ceiling, walk-in closet & spa-like bath with an oversized shower, soaking tub & double vanity. A second en-suite bedroom, two additional bedrooms & full bath complete the second floor. The partially finished lower level provides flexible bonus space. Outdoors, enjoy a private sports court & expansive fenced yard, ideal for recreation & entertaining. An attached 2-car garage, including one heated bay, adds convenience. Ideally located adjacent to Town Forest walking trails and just minutes from Wedgemere Station, downtown Winchester, schools, parks, and commuter routes. A rare opportunity to enjoy comfort, recreation & convenience in a sought-after location.

2 York Road, Winchester

Listing courtesy of Listing Agent: Katie Tully from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
70 Grove St, Winchester
$1,160,000
3 Beds ⋅ 2 Baths ⋅ 73537575 MLS
Well-maintained brick Cape offering 1996 sq. ft. of comfortable living space and a flexible floor plan. The sought-after first-floor primary bedroom and full bath provide convenient one-level living, complemented by hardwood floors, a fireplaced living room, dining room, sunroom, and an inviting kitchen with exterior access to the deck. A vaulted family room adds valuable living space, while additional bedrooms upstairs accommodate family, guests, or home office needs. Situated on a beautiful level .30-acre lot with a paved driveway and attached garage, this home has been lovingly cared for over the years. Enjoy easy access to Winchester Center's shops, restaurants, parks, trails, and commuter rail. Just minutes from Boston and major routes, the location is ideal for commuters. Winchester is renowned for its top-rated schools, vibrant town center, and exceptional quality of life.

70 Grove St, Winchester

Listing courtesy of Listing Agent: Maija Sawyer from Listing Office: William Raveis R.E. & Home Services.
6 Hancock St, Winchester
$1,170,000
5 Beds ⋅ 2 Baths ⋅ 73510153 MLS
Classic turn-of-the-century Victorian filled with charm and character, ready for its next owner. 5 total bedrooms; 4 on the second floor and 1 on the 3rd floor, plus 3rd floor office. 1.5 baths, this well-maintained home awaits your finishing touches and features hardwood floors throughout, showcasing its timeless architectural details. Enjoy warm summer evenings on the inviting screened front porch. Recent exterior paint, roof and updated high-efficiency gas heating system ensures modern comfort.The large, fenced backyard is perfect for entertaining, play, or gardening, complemented by a detached oversized garage. Ideally located just a short distance to the 2,600-acre Middlesex Fells Reservation perfect for hiking, jogging and dog walking. Close to Winchester Center’s vibrant shops and restaurants, top-rated schools, and commuter rail to Boston. With easy access to Rt. 93, downtown Boston is just minutes away. A rare opportunity to own a classic Victorian in an exceptional location.

6 Hancock St, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
886 Keene Rd, Winchester
$220,000
2 Beds ⋅ 1 Baths ⋅ 73474841 MLS
Your lucky day! Buyers financing fell through so this awsome home is on the market again! Welcome to 886 Keene Rd, a lovingly maintained home where timeless 1875 charm meets thoughtful modern updates. Set on a generous 0.47-acre lot, this property offers space, privacy, and a sense of calm that’s increasingly hard to find.From the moment you arrive, the home makes a warm first impression with classic appeal. A fenced-in front yard creates a welcoming buffer from the road—perfect for pets, gardening, or simply enjoying your own outdoor space. The seller added new gutters to the home. Inside, the home feels cozy and comfortable, offering two well-proportioned bedrooms and a recently remodeled bathroom that adds modern convenience without sacrificing character. The layout is efficient and inviting, ideal for year-round living, a weekend retreat, or a low-maintenance lifestyle. A one-car garage provides both vehicle protection and valuable storag. the septic failed but is still operational

886 Keene Rd, Winchester

Listing courtesy of Listing Agent: Rosemarie Ledogar from Listing Office: R. D. Ledogar Real Estate.
9 Wilson St, Winchester
$1,950,000
4 Beds ⋅ 4 Baths ⋅ 73537143 MLS
Step into the welcoming foyer and take in the period detail: stained-glass windows, large bow windows, detailed moldings, and hardwood floors. The sun-drenched formal dining room is made for gatherings, and the updated kitchen with butler's pantry makes entertaining a pleasure. On the 2nd floor, the primary suite includes a private office and sleeping porch, along with two additional bedrooms, a full bath, and laundry. The 3rd floor offers two more bedrooms and a full bath, providing flexibility for any household. The large screened porch extends living space through the warmer months, providing a quiet spot to read, dine, or relax. The flat backyard is peaceful and private, with perennial gardens and a bluestone patio perfect for al fresco dining. A mudroom and two-car garage add everyday practicality. Set on a quiet, dead-end street, minutes from the trails of the Middlesex Fells, and close to Muraco Elementary, downtown Winchester, the commuter rail, shops, cafes, and restaurants.

9 Wilson St, Winchester

Listing courtesy of Listing Agent: Elena Langlois from Listing Office: Compass.
15 Thornberry Rd, Winchester
$1,360,000
4 Beds ⋅ 3 Baths ⋅ 73529811 MLS
Located on a level corner lot in the desirable Vinson Owen School district and nearby Winchester Swim & Tennis Club, this ranch-style home offers abundant space and a flexible floor plan. The main level features three bedrooms, a full bath, hardwood floors, and a fireplace living room that flows into the dining area and kitchen. A heated sunroom/mudroom with skylights and exposed beams connects to the kitchen, garage, driveway, and backyard deck. A standout feature is the impressive two-story addition with a private entrance, first-floor sitting area, and second-floor bedroom suite with cathedral ceilings, abundant natural light, small kitchenette, and a full bath. The finished lower level has a full bath and two flexible rooms ideal for a family room, office, or gym. Complete with an attached garage, central AC, large deck, and professional landscaping with irrigation, this home offers exceptional space and flexibility in one of Winchester's most sought-after neighborhoods.

15 Thornberry Rd, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
18 Grayson Rd, Winchester
$1,738,000
3 Beds ⋅ 3 Baths ⋅ 73526595 MLS
OPEN HOUSES ONLY Discover this meticulously maintained 3 bed colonial just steps from Muraco Elementary and the Middlesex Fells. Rich hardwood floors flow through the formal dining room into the oversized, fireplaced living room ideal for entertaining. The beautifully appointed kitchen features a sunny breakfast area with access to a private deck. Upstairs, you'll find 2 spacious bedrooms and a primary suite that boasts a walk-in closet and a stunning en-suite bath with clawfoot tub. From the driveway, enter a newly renovated basement space including mudroom and ample flex space for exercise room or media/play space. Recent updates include a new furnace, water heater and expanded driveway to accommodate additional parking spaces. 1 car garage. Central air, insulated windows and doors, and a programmable thermostat to reduce annual energy costs. Fabulous location, steps from the Tri-Community bike path, hiking trails, Leonard Field, playgrounds and tennis courts

18 Grayson Rd, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
200 Swanton St Unit 228, Winchester
$330,000
1 Beds ⋅ 1 Baths ⋅ 73459781 MLS ⋅ ['Parkview Condos'] BLDG.
Welcome to Parkview Condos! This one bed one bath, bright unit features an open layout with peaceful views overlooking the pond. The low HOA fee includes heat, hot water, electricity, and air conditioning—an exceptional value. Highlights include a spacious living area, updated kitchen with new stainless steel appliances, a large bedroom with new flooring and excellent closet space, freshly painted throughout all rooms, and on-site laundry. Enjoy community amenities such as an in-ground pool, clubhouse, landscaped grounds, and on-site security. Conveniently located near shopping, schools, restaurants, and major highways. Bedroom and livingroom was virtually staged.

200 Swanton St Unit 228, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: REMAX Andrew Realty Services.
200 Swanton St Unit T37, Winchester
$2,675
2 Beds ⋅ 1 Baths ⋅ 73539019 MLS
Available now! Bright and spacious terrace-level 2-bedroom apartment offering exceptional value with heat, hot water, electricity, and air conditioning all included in the rent. This well-maintained home features an updated kitchen with dishwasher, generous living space, ample closet storage, and comfortable bedrooms. Enjoy the convenience of one assigned parking space included, with the option to obtain an additional parking pass through the HOA (fee applies). Residents also have access to the swimming pool. Conveniently located near shopping, restaurants, public transportation, and major commuter routes. Storage in basement.

200 Swanton St Unit T37, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: REMAX Andrew Realty Services.
303 Washington Street, Winchester
$1,367,500
6 Beds ⋅ 2 Baths ⋅ 73526417 MLS
Pleased to present this meticulously maintained and nicely updated two family home in the heart of Winchester! Each spacious unit is one level & features seven rooms including 3 large bedrooms, living room w fplc, dining room w/wainscoting, sunroom, kitchen & updated baths. The generously sized flowing rooms are highlighted by high ceilings, oversized windows, beautiful original woodwork and timeless architectural details; seamlessly blended with thoughtful updates throughout. This home presents an exceptional opportunity for investors, owner occupants w/ an income unit or for multi generational living. Enjoy the private landscaped back yard shaded by mature trees, perfect for relaxing or outdoor gatherings. Ideally located close to town, schools, shops, restaurants, commuter rail, and all Winchester has to offer. The special property combines character space and convenience all in one of the areas most desirable locations, a rare opportunity not to be missed!

303 Washington Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
307 Cross Street, Winchester
$1,730,000
5 Beds ⋅ 5 Baths ⋅ 73508927 MLS
Thoughtfully reimagined & expanded in 2019, this sophisticated colonial offers 5-6 bedrooms & 5 baths with a beautiful open floor plan - perfect for a growing family or multi-generational living. A striking granite kitchen with crisp white cabinetry, premium stainless appliances & oversized island flows seamlessly into the dining area - ideal for everyday living & refined entertaining. A fireplaced living room, office, bedroom & full bath complete this main level. Upstairs, two spacious bedrooms & a family bath complement a serene primary suite with spa-like bath amenities. The 3rd level offers an additional primary suite with luxurious soaking tub & flexible bonus space to use how you choose. A finished walk-out lower level with wet bar, bath, family room, exercise & play space adds further appeal. Acoustic windows enhance comfort throughout. Enjoy the one car garage, fully fenced yard, patio & deck - just moments to parks, town center, major routes, & Winchester's top-rated schools.

307 Cross Street, Winchester

Listing courtesy of Listing Agent: Dara Singleton from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
67 Church Unit 67, Winchester
$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.
30 Rangeley Road, Winchester
$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.
74 Wedgemere Avenue, Winchester
$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.
55 Brookside Ave., Winchester
$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.
21 Bellevue Avenue, Winchester
$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.
2 Eaton Ct, Winchester
$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.
22 Grove Pl Unit 6, Winchester
$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.
47 Yale Street, Winchester
$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.
44 Spruce Unit 2, Winchester
$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.
27 Everett Ave, Winchester
$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.
22 Hollywood Rd, Winchester
$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.
42 Spruce Unit 1, Winchester
$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.
49 Sheridan Circle, Winchester
$2,409,000
5 Beds ⋅ 5 Baths ⋅ 73534811 MLS
Like new, built in 2014, this exceptional home offers generous living space, a flexible floor plan, & quality finishes throughout. Situated on a large corner lot in a desirable Winchester neighborhood, the home features a spacious kitchen that opens to the family room w/ fireplace, creating the perfect gathering space. A sun-filled living room & formal dining room provide additional areas for entertaining & everyday living. The oversized primary suite includes a beautiful bath & 2 walk-in closets. Three additional large bedrooms, a full bath, & convenient second-floor laundry complete the 2nd level. The newly finished 3rd floor offers media/ bedroom w/full bath, providing excellent flexibility for guests, a home office, au pair suite, or potential in-law space. The finished lower level includes a rec room, full bath & abundant storage. Outside, enjoy the expansive yard w/ patio, fruit trees & plenty of space for recreation, gardening & more! Don't miss this one!

49 Sheridan Circle, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

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

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