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$1,775,000
5 Beds 4 Baths 73389326 MLS
Your very own private oasis tucked away in a cul-de-sac-like neighborhood just mins. to Winchester Center! Set on a deep, tree-lined lot, this stunning home offers 5 beds, 3.5 baths, & over 3,000 sq. ft. The versatile floor plan offers ground-level entry w/ a 2 car garage, 2 bedrooms (which can also function as work/play space,) & full bath/laundry area. The upper level is the heart of the home – The spacious living room w/ a wood-burning F/P & vaulted ceilings flows effortlessly into the open-concept dining area. The gourmet kitchen, anchored by a large center island, offers timeless finishes including sleek cabinetry, quartz, & S/S appliances. An oversized family room w/ abundant natural lighting completes the main living area. The opposite wing features 3 bedrooms & 2 full baths, including the primary w/ a newly renovated ensuite offering a soaking tub & dual sinks. Completing this retreat-like property is a swimming pool w/ pool house & 2 composite decks for summertime gatherings!

19 Pilgrim Dr, Winchester

Listing courtesy of Listing Agent: Gorfinkle Group from Listing Office: eXp Realty.

$2,890,000
5 Beds 5 Baths 73398676 MLS
Exceptional colonial on Myopia Hill showcasing an expansive rear family room addition, perfectly situated on an idyllic lot surrounded by lush gardens & mature landscape. This stately residence offers a true private oasis just minutes from all conveniences. Rich in finish, elegant in design w/ stunning living areas, large scale rooms & 4 fireplaces creating warm inviting spaces for every day living & entertaining. The custom kitchen leads to dramatic family room w/vaulted ceiling & walls of windows w/ fireplace & access to expansive patio w/ breathtaking views; seamlessly blending indoor & outdoor living. A formal dining room just off the kitchen provides an ideal space for hosting. This thoughtfully designed home includes 5 large beds & 4.5 baths, including the primary suite w/ beautiful bath & large walk in closet. A separate in-law apartment / guest suite offers flexibility & privacy for extended stays. Finished basement w/ family room, game room & gym plus 2 car direct entry garage

21 Fernway, Winchester

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

$2,175,000
6 Beds 4 Baths 73385985 MLS
Step into timeless elegance with this Colonial Revival, a true celebration of classic architecture, refined style, and exceptional craftsmanship. From the moment you arrive, the home's rich character makes a striking first impression, setting the stage for everything that follows. Inside, you’ll discover a harmonious blend of historic charm and modern comfort. Gleaming hardwood floors, intricate leaded glass cabinetry, and exquisite moldings whisper stories of a bygone era. High ceilings and sunlit rooms create a sense of airy sophistication, while cozy window seats invite you to unwind. The gracious, flowing layout features 6 spacious bedrooms and 3.5 baths, w/space for family, guests, or home office needs. For warm-weather evenings, the expansive screened-in porch is perfect for al fresco dining or simply soaking in the peaceful surroundings. Outside, enjoy a lush, level yard ideal for gardening & sports. Close to town, Fells, schools and trains!

9 Prospect St, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Advisors Living - Winchester.

$1,160,000
4 Beds 3 Baths 73385500 MLS
Set in the coveted Muraco School District, this classic 1915 Colonial offers the perfect blend of character and modern comfort. Featuring 4 bedrooms and 2.5 baths, the welcoming main level boasts an open-concept layout with an eat-in kitchen (granite countertops, stainless steel appliances), a dining room with charming built-ins, a spacious living room, and a convenient powder room with laundry. A mudroom leads to the private, fenced-in yard with a patio—ideal for outdoor entertaining.Upstairs, you’ll find three sunlit bedrooms and a full bath on the second floor, while the third floor offers a serene primary suite complete with a private bath and walk-in closet. Hardwood floors run throughout, and the finished basement adds valuable bonus space. All this in a fantastic location within walking distance to Leonard Field and the scenic trails of the Middlesex Fells Reservation.

518 Washington St, Winchester

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

$2,215,000
5 Beds 4 Baths 73395357 MLS
Situated in a coveted Winchester neighborhood, this classical five-bedroom home unfolds across 3 levels above grade—boasting sunlit living & dining spaces framed by walls of windows overlooking lush greenery, a chef’s kitchen appointed with an expansive butcher-block island & dual fuel oven & a serene primary suite featuring a private bath & walk-in closet. 2 additional bedrooms occupy the second floor, while the top level offers two more bedrooms & a full bath—ideal for guests. Outside, entertain on the porch, rear deck or patio in the private, landscaped yard. A detached two-car garage complements the classical exterior. The mostly finished basement adds versatile living space, including a cozy family room, office with above-grade windows & a wine-cellar nook with storage. Mere moments from Wedgemere station, bike trails, golf club, Ginn Field playground, Mystic Lake, Shannon Beach, Winchester Center & I-93, this move-in-ready home delivers style, space & location—a rare opportunity!

4 Winslow Rd, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.

$770,000
2 Beds 1 Baths 73376518 MLS ['White Horse Commons'] BLDG.
Looking to downsize or just live more modestly?Welcome to the sought-after White Horse Commons Condominiums, The perfect opportunity to enjoy the lovely town of Winchester and keep costs down. Near Symmes corner, downtown Winchester & Wedgemere train station, this wonderful 2 bedroom, 1 bathroom end unit lives and feels like a single home with windows on all three sides. The kitchen offers a sliding door out to a lovely private deck and yard space- perfect for relaxing and entertaining. The bright living and dining rooms feature many windows, vaulted ceilings and a beautiful fireplace w/ custom built-ins. Enjoy central air, 1 detached garage space, and a designated guest parking spot. Set back from the road w/ privacy & mature landscaping. The full basement could be finished for added space if needed. Ideal for commuters, just minutes to the train station, I-93, Route 128, the airport and downtown Boston! Don't miss this wonderful home located close to the entry of white horse commons!

22 Grove Place Unit 4, Winchester

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

$3,745,000
7 Beds 8 Baths 73371665 MLS
Stately elegance resides on one of the most desirable streets in the “Flats". This sprawling home details fine craftsmanship & modern finishes that a home of this caliber warrants. Sprawling open concept kitchen w/ impressive coffered ceilings, eat-in dining along w/ an adjoining family rm w/gas fireplace, dining room, and a formal living room make this the perfect space for entertaining. 7 bedrooms w/ 5 baths & 3 (1/2) baths. Primary bedroom boasts jack & jill walk in closets. Walk up 3rd floor offers yet additional living space. Lower level provides a myriad of options from media room, gym, bonus living area and a wine cellar. 2 car garage with possibility for a lift and an abundance of available storage, EV charging system, garage vacuum, along with a heated driveway, whole house generator and solar panels. Backyard equipped with play area, cabana, basketball court and gas hookup for grill. Easy access to the quaintness of Winchester Center.

25 Wedgemere Ave, Winchester

Listing courtesy of Listing Agent: Prestige Homes Realty Team from Listing Office: Prestige Homes Real Estate, LLC.

$3,000
2 Beds 1 Baths 73391346 MLS
Tucked away in the rear of the complex and facing a peaceful courtyard, this sparkling clean 2-bedroom, 1-bath unit offers the perfect blend of comfort, convenience, and charm. Accessible via a quiet side street, this home is ideal for anyone looking for tranquility without sacrificing location. Open-concept first floor with a non-working fireplace. Bonus loft space for a home office. Private basement with laundry. Freshly painted throughout. Heat & hot water included. Assigned off-street parking. Landscaping, trash removal, and snow removal included. Minutes to Winchester Center, seasonal farmers’ market, commuter rail (only 3 stops to North Station), and scenic trails. Easy access to major highways. NO PETS | NO SMOKING. Tenants pays for electric, gas for cooking, and internet. Heat and hot water is included in rent.

247 Washington St Unit 13, Winchester

Listing courtesy of Listing Agent: Brooke Zarbano from Listing Office: Regatta Realty.

$4,200
3 Beds 3 Baths 73398289 MLS
Winchester 3BR Townhome $4,200/mo | Available July 15Welcome to The Village at Winchester, a scenic condo community near conservation land and the Aberjona River.This spacious 1,834 sq ft townhome features: 3 bedrooms, 2.5 baths Fireplace in the living room Dining area with skylight and access to a private patio In-unit laundry, hardwood floors Garage + 2 driveway parking spacesEnjoy community amenities like a pool, tennis courts, clubhouse, and beautifully maintained grounds. Just a short walk to Winchester Center, commuter rail, shops, and restaurants. Located in the top-rated Winchester school district. Available July 15 $4,200/monthMessage to schedule a tour!

171 Swanton St Unit 41, Winchester

Listing courtesy of Listing Agent: Jerry Song from Listing Office: Greatland Real Estate LLC.

$1,627,000
5 Beds 4 Baths 73391568 MLS
Move right into this 5 b/r 4 bth colonial steps to Ambrose School! This picture perfect colonial features high ceilings,hdwd floors & an open first floor plan that creates an airy, welcoming atmosphere.The bright kitchen equipped with ss appliances & charming banquette seating is perfect for casual family meals; step outside to the deck overlooking the spacious yard or into the beautiful diningroom making it perfect for entertaining.The living room features beautiful built-in cabinetry, a cozy fireplace for gathering around, & french doors that lead to a versatile space perfect for a game room, music room, or playroom. 2nd floor includes 3 bedrooms; 2 full baths and plenty of windows for natural light.Space abounds in the 3rd floor with 2 sun splashed bedrooms with treetop views of the backyard & school field. A shared full bth completes this floor.The lower level maximizes living space, incl. a mudroom area, rec room & home office space.So much space & charm in an unbeatable location!

32 Oneida Road, Winchester

Listing courtesy of Listing Agent: Stephanie Mcgowan from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$2,425,000
4 Beds 5 Baths 73364169 MLS
Indulge in modern luxury with this stunning home, set on a double 1/2 acre lot. This 4 bedroom, 4.5-bathroom home seamlessly blends chic style with an abundance of functional space. The architectural design is dramatic, showcasing soaring ceilings, a stunning contemporary fireplace, state of the art kitchen & sun filled living room which opens to a fabulous deck, creating a perfect indoor-outdoor space. The gourmet kitchen features a sleek design w/ a large island, high end appliances, & stylish open shelving. Upstairs, the lavish primary suite features a spa like bath & large custom closet. The 3 additional bedrooms offer ensuite baths. The walk out LL family room w/ wet bar is the perfect space to unwind. This property also features a 2 gar attached garage, mud room, office & laundry room. The double lot offers many possibilities ~ level w/ patio. This home is located near conservation trails, top-rated schools & Boston offering a lifestyle of convenience, luxury & tranquility!

15 Churchill Road, Winchester

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

$1,149,000
4 Beds 3 Baths 73360866 MLS
This beautifully renovated, light-filled condo blends classic charm with modern updates in an ideal Winchester location. Completely gutted and converted in 2017, the home features an open-concept layout, highlighted by a spacious kitchen with granite countertops and a generous island—perfect for casual dining and entertaining. The finished basement adds versatile living space, while the primary bedroom offers a walk-in closet for optimal storage.With four bedrooms and two full baths, this home provides room to grow, all set on a charming side street just moments from shops and major roadways. Enjoy outdoor living on the private patio with newer custom fencing, surrounded by peace and convenience in equal measure.

83 Canal Unit 83, Winchester

Listing courtesy of Listing Agent: Mary O'Hagan from Listing Office: Barrett Sotheby's International Realty.

$2,635,000
5 Beds 6 Baths 73342518 MLS
Newly constructed 5,366 sq ft luxury home with attached 2 car garage! Featuring 5 bedrooms, 4 full and 2 half bath, and 4 levels of living, discover thoughtful elegance at every turn . The designer kitchen offers high-end appliances including a gas stove, double oven, and wet-bar with beverage fridge. Featuring an open-concept, the kitchen effortlessly flows into the sun-drenched living and dining areas, with home office, first floor bedroom, and large mudroom nearby. Ascend to the 2nd floor to find the spacious primary suite with walk-in closet, stunning bath with soaking tub, and attached deck, along with 3 other bedrooms and laundry. The 3rd floor features a bonus room with 1/2 bath, along with additional flexible space in the finished basement. Outside, the beautifully landscaped yard with cozy fire pit and patio creates the ultimate oasis. Winchester center and commuter rail less than 1 mile away. Don’t miss the chance to make 8 Chestnut home!

8 Chestnut St, Winchester

Listing courtesy of Listing Agent: The McLaren Team from Listing Office: Compass.

$1,300,000
3 Beds 2 Baths 73390030 MLS
Enter into the serene in this inviting Colonial, where timeless architecture meets thoughtful updates. High ceilings and sun-splashed, spacious rooms - accented by multiple bay windows and rich wood floors - create a light, airy feel. Featuring a cook’s kitchen with light cherry cabinets, gas cooktop with vented hood, generous storage, and a breakfast nook nestled in a five-window bay overlooking the backyard. Entertain in the expansive dining room, which comfortably accommodates a table for eight and showcases two built-in china cabinets. The first-floor family room is conveniently located off the kitchen, while the living room has cozy seating and custom-built bookcases and integrated storage. Upstairs, a third-floor loft-like area offers flexibility - perfect as a guest suite, home office, or studio. Updates include both full bathrooms, HVAC system, windows, and roof. Outside, enjoy a professionally landscaped and fenced yard, complete with a stone patio and storage shed.

49 Lincoln Street, Winchester

Listing courtesy of Listing Agent: Vantage Point Team from Listing Office: William Raveis R.E. & Home Services.

$1,650,000
3 Beds 4 Baths 73373998 MLS
One of the most picturesque homes in Winchester is now available! An iconic Mid-Century Modern originally designed by renowned architect Don Davis. Thoughtfully updated for today’s lifestyle, this architectural gem blends timeless design with modern functionality. The bold exterior opens into a dramatic living room featuring soaring cathedral ceilings, a statement fireplace, and custom built-ins. A sculptural African mahogany staircase anchors the space with warmth and elegance. Floor-to-ceiling glass doors seamlessly connects the interior to a lush, professionally landscaped backyard and patio—perfect for effortless indoor-outdoor living and entertaining. Inside, a sleek kitchen and beautifully updated bathrooms combine form and function, complemented by gorgeous hardwood floors, expansive storage, and new windows throughout. The finished lower level includes a stylish family room and a half bath. Two-car garage features EV charger, durable protective flooring, storage. Don’t miss it!

50 Johnson Road, Winchester

Listing courtesy of Listing Agent: Robert Ellington from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$2,690,000
4 Beds 4 Baths 73370908 MLS
Situated in the prestigious Myopia Hill neighborhood, this exceptional sprawling ranch offers a rare combination of timeless elegance & modern comfort. Set on a lush, private acre, offering nearly 4,500 sq ft of beautifully maintained living space designed for both everyday living & grand-scale entertaining. Exquisite custom woodwork, built-ins & moldings lend sophistication throughout. Well-appointed kitchen offers abundant cabinetry, a dedicated pantry, separate laundry room-combining practicality w/classic charm. At the heart of the home, a spectacular great room w/soaring, beamed cathedral ceilings, an inviting space for gatherings. Generously sized rooms & an intuitive layout provide ample flexibility to tailor the home to your own lifestyle. Expansive grounds (once w/curated gardens) with a water feature koi pond, a breathtaking outdoor oasis! Don’t miss your chance to own this remarkable home in one of Winchester's most coveted enclaves-with endless potential & enduring appeal.

34 Swan Road, Winchester

Listing courtesy of Listing Agent: Laurie Cappuccio from Listing Office: Classified Realty Group.

$1,207,500
3 Beds 2 Baths 73381698 MLS
Charming, fully renovated colonial in a prime Winchester neighborhood! The sunny front porch welcomes you in, leading to a bright bow front living room w/ high ceilings, that flows into the dining room & beautifully updated kitchen w/ stainless appliances & custom cabinetry w/ generous counter space. Off the kitchen, there’s a half bath and a bonus room—great as an office, playroom, or casual dining nook. Step outside to a fully fenced-in private backyard with a spacious new deck, ideal for entertaining, barbecues or relaxing. Upstairs you'll find three bedrooms, all with high ceilings and beautifully refinished hardwood floors, plus a fully renovated full bath with double vanity sinks and modern fixtures. The finished basement adds even more flexible living space. With major updates including a new roof, siding, A/C, and electrical, this home is truly move-in ready. Conveniently located near the Fells, Tri-Community bike path, Leonard Field & Muraco School. Don't miss this great home!

18 Brookside Avenue, Winchester

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

$6,800
4 Beds 4 Baths 73380452 MLS
This 4-bed,3.5-bath custom-designed and built in 2012 townhouse feels like a single family. Step onto the welcoming farmer’s porch into an open, airy layout with natural light streaming through large windows. It features gleaming wood floors and a chef’s kitchen with stainless steel appliances, granite countertops, custom cabinets, and a beautifully designed kitchen island. Living room has a stunning gas fireplace with a large TV above, and direct access to the rear deck and landscaped, fenced backyard. The 2nd floor boasts a massive main bedroom with a walk-in closet and en-suite bath with double vanities and a rain shower. 2 additional spacious bedrooms with excellent closet space and another full bath complete this level. The oversized 3rd floor includes a full bath, ideal for an office, guest room, or au-pair suite. Enjoy 3-zone heating and cooling with smart thermostats, and an attached garage. This property is perfect for making memories!

37 Rumford St Unit 37, Winchester

Listing courtesy of Listing Agent: Alina Wang Team from Listing Office: Coldwell Banker Realty - Lexington.

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