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LAKEFRONT! Nestled on the serene shores of the Mystic Lakes just 7 miles from Boston, close to the center & steps to Wedgemere train station/ 2 stops to North Station! A truly one-of-a-kind opportunity to enjoy peaceful waterfront living so close to Boston! This extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room! Located in one of Winchester’s most sought-after neighborhoods, the home blends high ceilings, rich original details, and a flowing floor plan ideal for both everyday living and elegant entertaining. The 2 room primary suite features a sitting room w/ fireplace, spa-like bath, and BR w/ picture window & stunning lake views. 4 bedrooms on the second floor plus 2 on the 3rd offer space for all. Step outside to a welcoming deck, level lawn, and lakeside fire pit..perfect for hosting or unwinding. Enjoy direct access to the lake for paddle-boarding, kayaking, and fishing direct rom your back yard.

6 Beds ⋅ 4 Baths ⋅ 73390942 MLS

LAKEFRONT! Nestled on the serene shores of the Mystic Lakes just 7 miles from Boston, close to the center & steps to Wedgemere train station/ 2 stops to North Station! A truly one-of-a-kind opportunity to enjoy peaceful waterfront living so close to Boston! This extraordinary 5-bedroom, 3.5-bath shingle style home offers rare privacy, timeless elegance & sweeping water views from every room! Located in one of Winchester’s most sought-after neighborhoods, the home blends high ceilings, rich original details, and a flowing floor plan ideal for both everyday living and elegant entertaining. The 2 room primary suite features a sitting room w/ fireplace, spa-like bath, and BR w/ picture window & stunning lake views. 4 bedrooms on the second floor plus 2 on the 3rd offer space for all. Step outside to a welcoming deck, level lawn, and lakeside fire pit..perfect for hosting or unwinding. Enjoy direct access to the lake for paddle-boarding, kayaking, and fishing direct rom your back yard.

9 Lakeview Terrace, Winchester

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

$3,295,000

Introducing 2 Atherton Road, an exceptional new construction residence offering over 6,100 sq. ft. of beautifully designed living space with 6 bedrooms, 6.5 baths, and a 3-car garage. A dramatic entry with soaring ceilings and a striking staircase sets the tone for the home’s sophisticated interiors. Designed for both everyday living and entertaining, the open-concept main level showcases an impressive oversized living and dining space that flows seamlessly into the chef’s kitchen, featuring a Thermador appliance package, wine chiller, wet bar, and custom finishes. The adjoining family room is anchored by an electric fireplace, while a private home office and first-floor guest suite add versatility to the floor plan. Upstairs, four bedrooms each feature private en-suite baths, including a spacious primary retreat with a beautifully appointed bath and oversized custom walk-in closet. The finished lower level expands the living space with a media room ideal for movie nights, an additional bedroom, and full bath. Outdoors, a private fenced backyard and patio create the perfect setting for relaxing and entertaining. Pella windows and thoughtfully selected finishes can be found throughout. Ideally situated in a desirable Winchester neighborhood just down the street from Ambrose Elementary School and moments from downtown Winchester’s restaurants, shops, cafés, and commuter rail service to Boston’s North Station. A sophisticated new construction offering that combines space, style, and an exceptional Winchester location.

6 Beds ⋅ 7 Baths ⋅ 73563095 MLS

Introducing 2 Atherton Road, an exceptional new construction residence offering over 6,100 sq. ft. of beautifully designed living space with 6 bedrooms, 6.5 baths, and a 3-car garage. A dramatic entry with soaring ceilings and a striking staircase sets the tone for the home’s sophisticated interiors. Designed for both everyday living and entertaining, the open-concept main level showcases an impressive oversized living and dining space that flows seamlessly into the chef’s kitchen, featuring a Thermador appliance package, wine chiller, wet bar, and custom finishes. The adjoining family room is anchored by an electric fireplace, while a private home office and first-floor guest suite add versatility to the floor plan. Upstairs, four bedrooms each feature private en-suite baths, including a spacious primary retreat with a beautifully appointed bath and oversized custom walk-in closet. The finished lower level expands the living space with a media room ideal for movie nights, an additional bedroom, and full bath. Outdoors, a private fenced backyard and patio create the perfect setting for relaxing and entertaining. Pella windows and thoughtfully selected finishes can be found throughout. Ideally situated in a desirable Winchester neighborhood just down the street from Ambrose Elementary School and moments from downtown Winchester’s restaurants, shops, cafés, and commuter rail service to Boston’s North Station. A sophisticated new construction offering that combines space, style, and an exceptional Winchester location.

2 Atherton Rd, Winchester

Listing courtesy of Listing Agent: Peter Kasseris from Listing Office: Serhant.

$2,999,000

Capture the seasons from the stunning rear porch! Must see this move in ready waterfront gem! Perfectly sited at the end of Wedgemere on Winter Pond, offering over 80 feet of direct water frontage w/ expansive yard and breathtaking views from nearly every room. Located in the exclusive Flats neighborhood, this home presents a rare opportunity to enjoy water activities such as kayaking, paddle-boarding, fishing, ice skating and hockey all while being just minutes from Winchester Center and the train to Boston; homes like this rarely come to market. Custom designed and lovingly owned by the original family, this home is now ready for its next chapter. Offering a beautiful flowing layout w/ gleaming hardwood floors, large rooms, featuring floor-to-ceiling bay windows with stunning views, 5 bedrooms, 2 full & 2 half baths, 4 fireplaces, a walk-out lower level rec room, & a gorgeous fenced yard with steps to the water. Truly a special setting that seamlessly combines privacy, views & accessibility in Winchesters TOP neighborhood!

5 Beds ⋅ 4 Baths ⋅ 73548103 MLS

Capture the seasons from the stunning rear porch! Must see this move in ready waterfront gem! Perfectly sited at the end of Wedgemere on Winter Pond, offering over 80 feet of direct water frontage w/ expansive yard and breathtaking views from nearly every room. Located in the exclusive Flats neighborhood, this home presents a rare opportunity to enjoy water activities such as kayaking, paddle-boarding, fishing, ice skating and hockey all while being just minutes from Winchester Center and the train to Boston; homes like this rarely come to market. Custom designed and lovingly owned by the original family, this home is now ready for its next chapter. Offering a beautiful flowing layout w/ gleaming hardwood floors, large rooms, featuring floor-to-ceiling bay windows with stunning views, 5 bedrooms, 2 full & 2 half baths, 4 fireplaces, a walk-out lower level rec room, & a gorgeous fenced yard with steps to the water. Truly a special setting that seamlessly combines privacy, views & accessibility in Winchesters TOP neighborhood!

10 Dartmouth Street, Winchester

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

$2,995,000

A distinctive new construction home where exceptional scale, thoughtful design, and refined finishes come together. Offering approximately 6,500 sq ft of beautifully finished living space, 8 Priscilla Ln was designed to feel impressive yet inviting. Soaring ceilings, graceful archways, and a dramatic two-story living room establish the home's architectural character, while an open, flowing layout is equally suited for everyday living and entertaining. At the heart of the home, the chef's kitchen features custom cabinetry, Thermador appliances, an oversized island, and a spacious walk-in pantry. The primary suite is a true retreat with a spa-inspired bath and generous walk-in closet, while multiple additional bedrooms offer the privacy of en suite baths. Downstairs, ceilings exceeding 10 feet elevate an expansive finished lower level with tremendous flexibility for a media room, gym, au pair or guest accommodations, or additional living space. Designed by Salt and Stone Co. and complete with a two-car garage, this is a home defined by craftsmanship, presence, and details rarely found in new construction.

5 Beds ⋅ 6 Baths ⋅ 73574330 MLS

A distinctive new construction home where exceptional scale, thoughtful design, and refined finishes come together. Offering approximately 6,500 sq ft of beautifully finished living space, 8 Priscilla Ln was designed to feel impressive yet inviting. Soaring ceilings, graceful archways, and a dramatic two-story living room establish the home's architectural character, while an open, flowing layout is equally suited for everyday living and entertaining. At the heart of the home, the chef's kitchen features custom cabinetry, Thermador appliances, an oversized island, and a spacious walk-in pantry. The primary suite is a true retreat with a spa-inspired bath and generous walk-in closet, while multiple additional bedrooms offer the privacy of en suite baths. Downstairs, ceilings exceeding 10 feet elevate an expansive finished lower level with tremendous flexibility for a media room, gym, au pair or guest accommodations, or additional living space. Designed by Salt and Stone Co. and complete with a two-car garage, this is a home defined by craftsmanship, presence, and details rarely found in new construction.

8 Priscilla Lane, Winchester

Listing courtesy of Listing Agent: The Pezzano Group from Listing Office: Rise Signature Homes.

$2,249,000

Built in 2021, this stunning home is ready for its next owners to enjoy. Its elevated setting provides a peaceful retreat with multiple areas for outdoor living, including a charming front porch. Inside, thoughtful design and exceptional attention to detail are evident throughout. The expansive open-concept kitchen, living and dining areas offer an ideal setting for entertaining, complemented by two gas fireplaces and central air. The luxurious primary suite features soaring ceilings, a walk-in closet, spa-like bath and private balcony. Three additional bedrooms offer generous proportions and ample closet space, while a conveniently located laundry room completes the second level. The ground floor provides a flexible living space ideal for guests, an au pair suite, or a recreation room. A whole-house generator offers added peace of mind. Ideally located approximately an equal distance to both Winchester and Arlington centers.

5 Beds ⋅ 4 Baths ⋅ 73574117 MLS

Built in 2021, this stunning home is ready for its next owners to enjoy. Its elevated setting provides a peaceful retreat with multiple areas for outdoor living, including a charming front porch. Inside, thoughtful design and exceptional attention to detail are evident throughout. The expansive open-concept kitchen, living and dining areas offer an ideal setting for entertaining, complemented by two gas fireplaces and central air. The luxurious primary suite features soaring ceilings, a walk-in closet, spa-like bath and private balcony. Three additional bedrooms offer generous proportions and ample closet space, while a conveniently located laundry room completes the second level. The ground floor provides a flexible living space ideal for guests, an au pair suite, or a recreation room. A whole-house generator offers added peace of mind. Ideally located approximately an equal distance to both Winchester and Arlington centers.

11 Locke St, Winchester

Listing courtesy of Listing Agent: Lesley Smith from Listing Office: Barrett Sotheby's International Realty.

$2,199,000

This distinguished residence on one of Winchester's most notable streets is a celebration of grand proportions, exquisite period craftsmanship, and timeless architectural beauty. High ceilings, four fireplaces, original hardwood floors, and beautifully scaled rooms create a sense of elegance that is increasingly difficult to find. The grand dining room is full of original details, anchored by a large fireplace and a big picture window that fills the room with natural light. A gracious living room offers another fireplace, beautiful hardwood floors, and impressive ceiling height, providing an elegant setting equally suited to intimate evenings and large-scale entertaining. A handsome first-floor study and south-facing sunroom offer quieter retreats, while the original butler’s pantry, complete with its own marble sink and original cabinets, speaks to the home’s history and the gracious way in which it was designed to be lived in. Six bedrooms + three full baths provide exceptional flexibility across the upper levels, with generous proportions and architectural details continuing throughout the home. Bonus space on the top floor and in the partially-finished basement provides room for a second home office, media room, gym or in-law space. The large patio offers privacy and entertaining space, while the grassy backyard has ample room to play. A rare three-story garage, originally designed with both chauffeur's quarters and a greenhouse, presents intriguing possibilities for the next owner. Set along prestigious Everett Avenue, in the Ambrose School District, it's a quick stroll to the town center, bus to Alewife, or Wedgemere Train Station. This residence offers an opportunity to become the next steward of a home whose craftsmanship, scale, and character simply cannot be replicated today.

6 Beds ⋅ 5 Baths ⋅ 73588192 MLS

This distinguished residence on one of Winchester's most notable streets is a celebration of grand proportions, exquisite period craftsmanship, and timeless architectural beauty. High ceilings, four fireplaces, original hardwood floors, and beautifully scaled rooms create a sense of elegance that is increasingly difficult to find. The grand dining room is full of original details, anchored by a large fireplace and a big picture window that fills the room with natural light. A gracious living room offers another fireplace, beautiful hardwood floors, and impressive ceiling height, providing an elegant setting equally suited to intimate evenings and large-scale entertaining. A handsome first-floor study and south-facing sunroom offer quieter retreats, while the original butler’s pantry, complete with its own marble sink and original cabinets, speaks to the home’s history and the gracious way in which it was designed to be lived in. Six bedrooms + three full baths provide exceptional flexibility across the upper levels, with generous proportions and architectural details continuing throughout the home. Bonus space on the top floor and in the partially-finished basement provides room for a second home office, media room, gym or in-law space. The large patio offers privacy and entertaining space, while the grassy backyard has ample room to play. A rare three-story garage, originally designed with both chauffeur's quarters and a greenhouse, presents intriguing possibilities for the next owner. Set along prestigious Everett Avenue, in the Ambrose School District, it's a quick stroll to the town center, bus to Alewife, or Wedgemere Train Station. This residence offers an opportunity to become the next steward of a home whose craftsmanship, scale, and character simply cannot be replicated today.

42 Everett Ave, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.

$1,870,000

Space where you need it, flexibility where you want it. This extensively renovated 5-bedroom Colonial offers a rare combination of a first-floor bedroom, two upstairs suites, finished lower level, attached 2-car garage, and nearly 1/3 acre, all just minutes from Winchester Center. Sophisticated and comfortable, the home features beautifully scaled living spaces and a versatile floor plan designed for everyday living and entertaining alike. The sun-filled main level offers hardwood floors and thoughtful architectural details, with a spacious eat-in kitchen featuring an island, abundant prep space, and seamless access to the patio and private backyard. A formal dining room, oversized fireplaced living room, mudroom, half bath, and first-floor bedroom provide exceptional flexibility. Upstairs are two impressive suites with cathedral ceilings, walk-in closets, and private baths, along with two additional bedrooms, a full bath, and laundry. The finished lower level offers a spacious family room with fireplace and ample storage. An attached 2-car garage completes this exceptional home, conveniently located near Winchester Center’s shops, restaurants, commuter rail, and major routes.

5 Beds ⋅ 4 Baths ⋅ 73545952 MLS

Space where you need it, flexibility where you want it. This extensively renovated 5-bedroom Colonial offers a rare combination of a first-floor bedroom, two upstairs suites, finished lower level, attached 2-car garage, and nearly 1/3 acre, all just minutes from Winchester Center. Sophisticated and comfortable, the home features beautifully scaled living spaces and a versatile floor plan designed for everyday living and entertaining alike. The sun-filled main level offers hardwood floors and thoughtful architectural details, with a spacious eat-in kitchen featuring an island, abundant prep space, and seamless access to the patio and private backyard. A formal dining room, oversized fireplaced living room, mudroom, half bath, and first-floor bedroom provide exceptional flexibility. Upstairs are two impressive suites with cathedral ceilings, walk-in closets, and private baths, along with two additional bedrooms, a full bath, and laundry. The finished lower level offers a spacious family room with fireplace and ample storage. An attached 2-car garage completes this exceptional home, conveniently located near Winchester Center’s shops, restaurants, commuter rail, and major routes.

79 Grove St, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.

$1,799,999

Welcome to 30 Allen Road, a beautifully situated Colonial in one of Winchester’s most desirable and walkable neighborhoods. Ideally located within easy reach of top-rated schools, shops, restaurants, and the commuter rail, this inviting home offers the space, character, and flexibility today’s buyers are looking for. The first floor features a spacious kitchen equipped with a Sub-Zero refrigerator and GE Monogram range top, opening directly to a wonderful family room with vaulted ceilings, skylights, and a gas fireplace. A bright sunroom with radiant heat provides an inviting space for year-round enjoyment, while the elegant living room offers a classic wood-burning fireplace. A formal dining room and convenient half bath complete the main level. Upstairs, the second floor offers three bedrooms, including a private primary suite, along with one additional full bath. The top floor provides two additional rooms, including a fourth bedroom and a versatile bonus space ideal for a recreation room, home office, guest space, or playroom. Outside, the property enjoys a peaceful, wooded setting with a fenced yard offering privacy and plenty of room for outdoor enjoyment. A single-car garage adds convenience and valuable storage. With its exceptional location, generous bedroom count, flexible living spaces, and charming combination of classic and modern amenities, 30 Allen Road offers a wonderful opportunity to enjoy all that Winchester has to offer.

4 Beds ⋅ 3 Baths ⋅ 73577229 MLS

Welcome to 30 Allen Road, a beautifully situated Colonial in one of Winchester’s most desirable and walkable neighborhoods. Ideally located within easy reach of top-rated schools, shops, restaurants, and the commuter rail, this inviting home offers the space, character, and flexibility today’s buyers are looking for. The first floor features a spacious kitchen equipped with a Sub-Zero refrigerator and GE Monogram range top, opening directly to a wonderful family room with vaulted ceilings, skylights, and a gas fireplace. A bright sunroom with radiant heat provides an inviting space for year-round enjoyment, while the elegant living room offers a classic wood-burning fireplace. A formal dining room and convenient half bath complete the main level. Upstairs, the second floor offers three bedrooms, including a private primary suite, along with one additional full bath. The top floor provides two additional rooms, including a fourth bedroom and a versatile bonus space ideal for a recreation room, home office, guest space, or playroom. Outside, the property enjoys a peaceful, wooded setting with a fenced yard offering privacy and plenty of room for outdoor enjoyment. A single-car garage adds convenience and valuable storage. With its exceptional location, generous bedroom count, flexible living spaces, and charming combination of classic and modern amenities, 30 Allen Road offers a wonderful opportunity to enjoy all that Winchester has to offer.

30 Allen Road, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.

$1,699,000

Built in 2019 and perfectly positioned near downtown Winchester and the commuter rail, this 5 bed, 3.5 bath Colonial offers a bright, open layout with oversized windows, newly installed custom interior shutters and great natural light throughout. The large living room flows into the dining room, making the first floor great for everyday living and entertaining. The kitchen features a 2025 Thermador appliance package and oversized breakfast nook, with access to the deck, patio and fully fenced yard. Exterior work and fencing were completed in 2022, with mature evergreens and the newer fence creating a private and serene outdoor setting. Upstairs, the spacious primary suite includes a walk-in closet and en-suite bath with soaking tub and standing shower. Two additional bedrooms, a Jack-and-Jill bathroom and laundry room complete the second floor, with two more bedrooms and a full bath on the third. Ample storage throughout the home, including custom closets and additional storage tucked under the eaves on the third floor. Solar panels with Tesla Powerwalls and a HEATED DRIVEWAY are great added features. The unfinished basement with 8'+ ceilings offers excellent potential for future living space.

5 Beds ⋅ 4 Baths ⋅ 73568493 MLS

Built in 2019 and perfectly positioned near downtown Winchester and the commuter rail, this 5 bed, 3.5 bath Colonial offers a bright, open layout with oversized windows, newly installed custom interior shutters and great natural light throughout. The large living room flows into the dining room, making the first floor great for everyday living and entertaining. The kitchen features a 2025 Thermador appliance package and oversized breakfast nook, with access to the deck, patio and fully fenced yard. Exterior work and fencing were completed in 2022, with mature evergreens and the newer fence creating a private and serene outdoor setting. Upstairs, the spacious primary suite includes a walk-in closet and en-suite bath with soaking tub and standing shower. Two additional bedrooms, a Jack-and-Jill bathroom and laundry room complete the second floor, with two more bedrooms and a full bath on the third. Ample storage throughout the home, including custom closets and additional storage tucked under the eaves on the third floor. Solar panels with Tesla Powerwalls and a HEATED DRIVEWAY are great added features. The unfinished basement with 8'+ ceilings offers excellent potential for future living space.

30 Farrow St, Winchester

Listing courtesy of Listing Agent: Carlisle Group from Listing Office: Compass.

$1,599,000

Set on a quiet cul-de-sac in a sought-after Winchester location, 4 Harrington Road is a picture-perfect home that combines timeless appeal with thoughtful updates and an easy, comfortable layout. Just moments from downtown Winchester, multiple commuter rail stations, local schools, and more, the location offers the perfect balance of convenience and neighborhood charm. The first floor is warm and welcoming, featuring a renovated kitchen with breakfast bar, a formal dining room, and a fireplaced family room that opens to a beautiful three-season sunroom. Overlooking the expansive, level backyard, the sunroom is a standout space for morning coffee, casual gatherings, or simply enjoying the outdoors. A full bathroom and dedicated home office add flexibility to the main living level. Upstairs, three bedrooms and a full bathroom provide comfortable accommodations, with the primary bedroom offering direct access to the bath. The lower level presents an opportunity to create additional living space tailored to your needs. A fireplaced room offers a natural starting point for a future family room, while a separate bonus room with laundry could become a playroom, home gym, or creative retreat. With its inviting character, versatile spaces, and exceptional location close to everything Winchester has to offer, 4 Harrington Road is one you will not want to miss!

3 Beds ⋅ 2 Baths ⋅ 73590582 MLS

Set on a quiet cul-de-sac in a sought-after Winchester location, 4 Harrington Road is a picture-perfect home that combines timeless appeal with thoughtful updates and an easy, comfortable layout. Just moments from downtown Winchester, multiple commuter rail stations, local schools, and more, the location offers the perfect balance of convenience and neighborhood charm. The first floor is warm and welcoming, featuring a renovated kitchen with breakfast bar, a formal dining room, and a fireplaced family room that opens to a beautiful three-season sunroom. Overlooking the expansive, level backyard, the sunroom is a standout space for morning coffee, casual gatherings, or simply enjoying the outdoors. A full bathroom and dedicated home office add flexibility to the main living level. Upstairs, three bedrooms and a full bathroom provide comfortable accommodations, with the primary bedroom offering direct access to the bath. The lower level presents an opportunity to create additional living space tailored to your needs. A fireplaced room offers a natural starting point for a future family room, while a separate bonus room with laundry could become a playroom, home gym, or creative retreat. With its inviting character, versatile spaces, and exceptional location close to everything Winchester has to offer, 4 Harrington Road is one you will not want to miss!

4 Harrington Road, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.

$1,529,000

Classic East Hill center-entrance Colonial offered for the first time in decades, blending timeless character with gracious everyday living. The front-to-back living room features a beamed ceiling and gas fireplace, creating a warm and inviting gathering space. The dining room is accented by built-in china cabinets, while the eat-in kitchen offers stone counters, stainless steel appliances, recessed lighting, and access to a delightful three-season enclosed porch with cathedral ceiling, skylights, and jalousie windows. A main-level office with windows on three sides and a half bath add flexibility. Upstairs, the primary suite includes a private bath, sitting room, and laundry, complemented by two additional bedrooms and a full bath. A large deck, beautifully maintained yard, central air, and two-car detached garage complete this special East Hill home.

3 Beds ⋅ 3 Baths ⋅ 73562422 MLS

Classic East Hill center-entrance Colonial offered for the first time in decades, blending timeless character with gracious everyday living. The front-to-back living room features a beamed ceiling and gas fireplace, creating a warm and inviting gathering space. The dining room is accented by built-in china cabinets, while the eat-in kitchen offers stone counters, stainless steel appliances, recessed lighting, and access to a delightful three-season enclosed porch with cathedral ceiling, skylights, and jalousie windows. A main-level office with windows on three sides and a half bath add flexibility. Upstairs, the primary suite includes a private bath, sitting room, and laundry, complemented by two additional bedrooms and a full bath. A large deck, beautifully maintained yard, central air, and two-car detached garage complete this special East Hill home.

20 Sargent Rd, Winchester

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

$1,299,000

Welcome to 8 North Gateway, a spacious, rambling six-bedroom home offering an exceptional opportunity to create something truly special in a desirable location close to Winchester Center and Boston. Deceiving from the street view, this spacious home w/ multiple additions offers a versatile floor plan and generous living spaces, with future expansion potential. The first floor features easy living with a large primary bedroom suite addition including a full bath, w/ adjacent laundry plus 2 additional rooms which could serve as bedrooms, or home offices. A beautiful oversized family room with walls of glass, vaulted beamed ceilings w/sliders to patio is a must see, along with an inviting screen porch, a formal dining room, living room w/ fireplace & kitchen w/ craftsman cabinetry. Upstairs, you’ll find three additional bedrooms and a full bath, providing flexibility for family, guests. A large unfinished basement offers additional space and would be easy to finish into a media/game room or playroom. A sizable corner lot offers plenty of space for outdoor enjoyment and entertaining, while the friendly neighborhood and convenient location create a wonderful place to make home. For commuters, easy access to Boston and major routes adds to the appeal. A great opportunity to make this cherished family home your own...add your personal touch & transform 8 N.Gateway into the home of your dreams! Contact us today for a private showing!

6 Beds ⋅ 3 Baths ⋅ 73584820 MLS

Welcome to 8 North Gateway, a spacious, rambling six-bedroom home offering an exceptional opportunity to create something truly special in a desirable location close to Winchester Center and Boston. Deceiving from the street view, this spacious home w/ multiple additions offers a versatile floor plan and generous living spaces, with future expansion potential. The first floor features easy living with a large primary bedroom suite addition including a full bath, w/ adjacent laundry plus 2 additional rooms which could serve as bedrooms, or home offices. A beautiful oversized family room with walls of glass, vaulted beamed ceilings w/sliders to patio is a must see, along with an inviting screen porch, a formal dining room, living room w/ fireplace & kitchen w/ craftsman cabinetry. Upstairs, you’ll find three additional bedrooms and a full bath, providing flexibility for family, guests. A large unfinished basement offers additional space and would be easy to finish into a media/game room or playroom. A sizable corner lot offers plenty of space for outdoor enjoyment and entertaining, while the friendly neighborhood and convenient location create a wonderful place to make home. For commuters, easy access to Boston and major routes adds to the appeal. A great opportunity to make this cherished family home your own...add your personal touch & transform 8 N.Gateway into the home of your dreams! Contact us today for a private showing!

8 North Gateway, Winchester

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

$1,299,000

Custom-built and thoughtfully designed for comfortable one-level living, this spacious ranch offers a flexible floor plan, ample living spaces, and convenient access to the walking trails and recreational amenities of nearby Horn Pond. The main level features a gracious formal living room with a wood-burning fireplace, an elegant dining room with custom paneling, and an updated eat-in kitchen with direct access to the picturesque backyard. Three generously sized bedrooms and a full bath complete the main level. Upstairs, a fourth bedroom is complemented by an unfinished storage room with excellent potential for a fifth bedroom, home office, or additional living space.The walkout lower level adds even more flexibility with a family room featuring a second fireplace, half bath, dedicated laundry room, mudroom, and direct access to the oversized two-car garage. Two additional storage areas provide the opportunity to create a home office, gym, playroom, workshop, or finished living space. With substantial square footage throughout, there is plenty of room to adapt the home to your needs. Beautiful custom moldings, well-proportioned rooms, abundant natural light, and a well-designed floor plan add warmth and character throughout. Recent improvements include a new roof, spray foam insulation, updated windows, and newer appliances. Outside, the park-like backyard is a true retreat, highlighted by a spectacular 20' x 40' in-ground pool, patio area, and exceptional privacy while abutting the Lynch School fields. Just moments from the Horn Pond Recreation Area, enjoy convenient access to walking trails, scenic views, playgrounds, fishing, and year-round outdoor recreation. With the newly constructed Lynch Elementary School nearby, along with shopping and major commuting routes, this home offers an ideal blend of privacy, recreation, and everyday convenience.

4 Beds ⋅ 2 Baths ⋅ 73574477 MLS

Custom-built and thoughtfully designed for comfortable one-level living, this spacious ranch offers a flexible floor plan, ample living spaces, and convenient access to the walking trails and recreational amenities of nearby Horn Pond. The main level features a gracious formal living room with a wood-burning fireplace, an elegant dining room with custom paneling, and an updated eat-in kitchen with direct access to the picturesque backyard. Three generously sized bedrooms and a full bath complete the main level. Upstairs, a fourth bedroom is complemented by an unfinished storage room with excellent potential for a fifth bedroom, home office, or additional living space.The walkout lower level adds even more flexibility with a family room featuring a second fireplace, half bath, dedicated laundry room, mudroom, and direct access to the oversized two-car garage. Two additional storage areas provide the opportunity to create a home office, gym, playroom, workshop, or finished living space. With substantial square footage throughout, there is plenty of room to adapt the home to your needs. Beautiful custom moldings, well-proportioned rooms, abundant natural light, and a well-designed floor plan add warmth and character throughout. Recent improvements include a new roof, spray foam insulation, updated windows, and newer appliances. Outside, the park-like backyard is a true retreat, highlighted by a spectacular 20' x 40' in-ground pool, patio area, and exceptional privacy while abutting the Lynch School fields. Just moments from the Horn Pond Recreation Area, enjoy convenient access to walking trails, scenic views, playgrounds, fishing, and year-round outdoor recreation. With the newly constructed Lynch Elementary School nearby, along with shopping and major commuting routes, this home offers an ideal blend of privacy, recreation, and everyday convenience.

253 Pond St, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.

$1,295,000

This Ledges "A" Style townhouse condo offers extensive single floor living with a spacious first floor primary suite as well as a separate second floor suite and loft area. The main bedroom is truly vast. The first floor den can be used as a third bedroom. The home is move-in ready with all new oak hardwood floors throughout the finished areas! Entirely freshly painted in Moore's attractive Simply White. With cathedral ceilings, tall sunny windows, exterior deck, living room with fireplace, formal dining room, den/3rd bedroom, and kitchen with breakfast area, the home offers a lovely balance of airy open living and generous private spaces. Only bathrooms and kitchen are tiled. The home is located on a private cul-de-sac, with attached two-car garage offering convenient safety in snowy and icy weather! Enormous walk-out basement with high ceilings should you wish to expand your domain! Except for the front garden, all landscaping, exterior maintenance, snow removal done for you while you enjoy the association clubhouse, outdoor pool, tennis court and walking trails in the adjacent Sucker Brook Conservation area. Just minutes from Boston via car or train from charming Winchester Center with its coffee shops, restaurants and outdoor summer dining, pharmacies, and Whole Foods Market all near.

3 Beds ⋅ 3 Baths ⋅ 73580454 MLS ⋅ ['The Ledges'] BLDG.

This Ledges "A" Style townhouse condo offers extensive single floor living with a spacious first floor primary suite as well as a separate second floor suite and loft area. The main bedroom is truly vast. The first floor den can be used as a third bedroom. The home is move-in ready with all new oak hardwood floors throughout the finished areas! Entirely freshly painted in Moore's attractive Simply White. With cathedral ceilings, tall sunny windows, exterior deck, living room with fireplace, formal dining room, den/3rd bedroom, and kitchen with breakfast area, the home offers a lovely balance of airy open living and generous private spaces. Only bathrooms and kitchen are tiled. The home is located on a private cul-de-sac, with attached two-car garage offering convenient safety in snowy and icy weather! Enormous walk-out basement with high ceilings should you wish to expand your domain! Except for the front garden, all landscaping, exterior maintenance, snow removal done for you while you enjoy the association clubhouse, outdoor pool, tennis court and walking trails in the adjacent Sucker Brook Conservation area. Just minutes from Boston via car or train from charming Winchester Center with its coffee shops, restaurants and outdoor summer dining, pharmacies, and Whole Foods Market all near.

7 Wainwright Rd. Unit #47, Winchester

Listing courtesy of Listing Agent: Felicity F. Tuttle from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$1,195,000

Introducing 4 Stone Ave, a charming 3 bed, 1.5 bath Colonial Style home, one block from Muraco School, and minutes from the Middlesex Fells Reservation, offering over 2,575 acres of pristine woodlands, reservoirs, and scenic trails perfect for outdoor recreation. Beautiful updates complement the home’s original oak woodwork, including stained oak Harvey windows with tilt in sashes. The spacious front foyer opens into the living room with a wood burning fireplace. The formal dining room leads out to a serene private rear deck, overlooking a fully fenced yard with native plantings. The sizable kitchen highlights electric cooking, a built in microwave, and peninsula providing additional seating. A side addition added a large front to back family room with abundant natural light, providing even more livable space on the first floor. A private home office with classic French door completes this level. Upstairs, you’ll find a 2021 renovated full bathroom, three sizable bedrooms, and extensive storage space including 25FT attic closet. The walk out basement offers W/D, an above grade, finished room perfect for a home gym or office, and unfinished storage space. A one car garage, off street parking for 3 additional cars and cost efficient solar panels add everyday practicality. Just minutes from vibrant Winchester Center, this home offers access to local shops, cafés, highly rated restaurants, two MBTA commuter rail stations and Winchester’s acclaimed public school system, along with easy access to I-93, Route 128 and Route 3.

3 Beds ⋅ 2 Baths ⋅ 73582171 MLS

Introducing 4 Stone Ave, a charming 3 bed, 1.5 bath Colonial Style home, one block from Muraco School, and minutes from the Middlesex Fells Reservation, offering over 2,575 acres of pristine woodlands, reservoirs, and scenic trails perfect for outdoor recreation. Beautiful updates complement the home’s original oak woodwork, including stained oak Harvey windows with tilt in sashes. The spacious front foyer opens into the living room with a wood burning fireplace. The formal dining room leads out to a serene private rear deck, overlooking a fully fenced yard with native plantings. The sizable kitchen highlights electric cooking, a built in microwave, and peninsula providing additional seating. A side addition added a large front to back family room with abundant natural light, providing even more livable space on the first floor. A private home office with classic French door completes this level. Upstairs, you’ll find a 2021 renovated full bathroom, three sizable bedrooms, and extensive storage space including 25FT attic closet. The walk out basement offers W/D, an above grade, finished room perfect for a home gym or office, and unfinished storage space. A one car garage, off street parking for 3 additional cars and cost efficient solar panels add everyday practicality. Just minutes from vibrant Winchester Center, this home offers access to local shops, cafés, highly rated restaurants, two MBTA commuter rail stations and Winchester’s acclaimed public school system, along with easy access to I-93, Route 128 and Route 3.

4 Stone Ave, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.

$1,000,000

Storybook charm meets relaxed, easy living in this inviting Winchester Colonial, ideally located near the natural beauty of the Fells Reservation, Muraco Elementary, and convenient commuter routes. Set on a lovely lot with mature plantings, the property offers a private-feeling outdoor setting, a detached two-car garage, and pretty, original architectural details throughout. Inside, natural light fills the freshly painted interior. The fireplaced living room with wood stove flows seamlessly into the updated kitchen and dining room, creating an easy connection for everyday living and entertaining. The dining room opens to a bright, welcoming sunroom - an ideal spot for morning coffee, reading, or enjoying views of the surrounding yard. Upstairs, two generously sized bedrooms are joined by a third bedroom with a walk-up to additional attic storage, and a charming full bath. The lower level provides even more versatility with a finished bonus room, laundry, plentiful storage and exterior access. Thoughtfully maintained and move-in ready, this home combines timeless architectural character with smart updates and practical spaces designed for today’s lifestyle.

3 Beds ⋅ 1 Baths ⋅ 73581744 MLS

Storybook charm meets relaxed, easy living in this inviting Winchester Colonial, ideally located near the natural beauty of the Fells Reservation, Muraco Elementary, and convenient commuter routes. Set on a lovely lot with mature plantings, the property offers a private-feeling outdoor setting, a detached two-car garage, and pretty, original architectural details throughout. Inside, natural light fills the freshly painted interior. The fireplaced living room with wood stove flows seamlessly into the updated kitchen and dining room, creating an easy connection for everyday living and entertaining. The dining room opens to a bright, welcoming sunroom - an ideal spot for morning coffee, reading, or enjoying views of the surrounding yard. Upstairs, two generously sized bedrooms are joined by a third bedroom with a walk-up to additional attic storage, and a charming full bath. The lower level provides even more versatility with a finished bonus room, laundry, plentiful storage and exterior access. Thoughtfully maintained and move-in ready, this home combines timeless architectural character with smart updates and practical spaces designed for today’s lifestyle.

23 Stone Ave., Winchester

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

199 Washington Street Unit 199, Winchester

$975,000

Enjoy being just a few blocks from Winchester Center in this spacious condo with unique separate guest suite or home office. This single family alternative features 3 bedrooms on the main level and a fourth tucked away in the back of the second floor along with a 3rd bath and kitchenette. Come in the back door from the 1-car garage, or 3 parkings spaces in the driveway, straight into the large, remodeled kitchen with dining area. Appreciate the large windows in the living room. Charming details complement modern improvements. The primary suite is large enough to have an office setup within the space. Primary and hall bath have been updated. Looking for outdoor space? Whether you love the Middlesex Fells, want to have friends over for al fresco dining or do a little gardening, this is the home for you. Condo expenses are split between the 2 units. Town Center, schools, commuter rail, restaurants, shopping and the farmers market are all just a few blocks away. Boston and Cambridge are less than 9 miles away from this spot conveniently located to 93 and 95.

4 Beds ⋅ 3 Baths ⋅ 73573734 MLS

Enjoy being just a few blocks from Winchester Center in this spacious condo with unique separate guest suite or home office. This single family alternative features 3 bedrooms on the main level and a fourth tucked away in the back of the second floor along with a 3rd bath and kitchenette. Come in the back door from the 1-car garage, or 3 parkings spaces in the driveway, straight into the large, remodeled kitchen with dining area. Appreciate the large windows in the living room. Charming details complement modern improvements. The primary suite is large enough to have an office setup within the space. Primary and hall bath have been updated. Looking for outdoor space? Whether you love the Middlesex Fells, want to have friends over for al fresco dining or do a little gardening, this is the home for you. Condo expenses are split between the 2 units. Town Center, schools, commuter rail, restaurants, shopping and the farmers market are all just a few blocks away. Boston and Cambridge are less than 9 miles away from this spot conveniently located to 93 and 95.

199 Washington Street Unit 199, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$829,000

Sunlit, pristine and perfectly located in the center of town ! This second floor unit features a fully renovated white kitchen (2019) with new appliances, seamlessly flowing into an open, inviting living space. Step directly out onto your private roof deck overlooking tranquil views of Wedge Pond...the ultimate spot for morning coffee or evening relaxing. The two bedroom, two bath unit also offers your own washer dryer for your convenience. Enjoy this turn-key convenience with a covered deeded parking space, an additional storage unit, and access to a beautiful in-ground pool. Close to shopping, local dining, schools, commuter rail and highways. Move in living doesn't get better than this. Schedule a showing now and don't miss out.Complete with Anderson windows and doors, mirrored dining room wall which reflects the view of the deck, custom molding and fireplaced living room.

2 Beds ⋅ 2 Baths ⋅ 73559598 MLS

Sunlit, pristine and perfectly located in the center of town ! This second floor unit features a fully renovated white kitchen (2019) with new appliances, seamlessly flowing into an open, inviting living space. Step directly out onto your private roof deck overlooking tranquil views of Wedge Pond...the ultimate spot for morning coffee or evening relaxing. The two bedroom, two bath unit also offers your own washer dryer for your convenience. Enjoy this turn-key convenience with a covered deeded parking space, an additional storage unit, and access to a beautiful in-ground pool. Close to shopping, local dining, schools, commuter rail and highways. Move in living doesn't get better than this. Schedule a showing now and don't miss out.Complete with Anderson windows and doors, mirrored dining room wall which reflects the view of the deck, custom molding and fireplaced living room.

666 Main Street Unit 207, Winchester

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

$799,000

$5000 Closing Costs Credit to Buyer closing by Oct. 31st. Best Value in Winchester! Charming and Spacious Custom Built Mid-Century Bungalow offers a terrific opportunity to live in Winchester! Do you want to send your children to the award-winning public schools? Need an in-law apt.? Generously sized, sun-drenched, freshly painted rooms with high ceilings and hardwood floors, beautiful architectural details, and two fireplaces. A private, flat backyard perfect for growing gardens and outdoor fun. A fully finished lower-level creates excellent 2nd living space for your needs. In-town location convenient to the Boston Commuter Rail and all picturesque downtown Winchester offers. Come See this sweet, unspoiled Mid-Century home on a dead-end street!

4 Beds ⋅ 2 Baths ⋅ 73542597 MLS

$5000 Closing Costs Credit to Buyer closing by Oct. 31st. Best Value in Winchester! Charming and Spacious Custom Built Mid-Century Bungalow offers a terrific opportunity to live in Winchester! Do you want to send your children to the award-winning public schools? Need an in-law apt.? Generously sized, sun-drenched, freshly painted rooms with high ceilings and hardwood floors, beautiful architectural details, and two fireplaces. A private, flat backyard perfect for growing gardens and outdoor fun. A fully finished lower-level creates excellent 2nd living space for your needs. In-town location convenient to the Boston Commuter Rail and all picturesque downtown Winchester offers. Come See this sweet, unspoiled Mid-Century home on a dead-end street!

84 Oak Street, Winchester

Listing courtesy of Listing Agent: John E. Magazzu from Listing Office: Charlesgate Realty Group LLC.

$619,000

Great opportunity to live on a quiet side street conveniently located near the town center and Elizabeth C. McDonald Field, featuring tennis courts, ball fields, basketball courts, and a playground. This well-maintained 3-bedroom, 3.5-bath townhouse offers 1,225 sq. ft. of comfortable living space. The charming home features high ceilings and a functional multi-level layout with a bright living area, spacious kitchen, two generously sized bedrooms, and a large office. Numerous updates were completed in 2023, including hardwood flooring, a finished attic, five ductless mini-split AC units, and renovated bathrooms. A new roof was installed in 2024. Additional updates include a high-efficiency gas boiler and hot water system installed in 2019. Conveniently located within walking distance to the newly built Lynch Elementary School and Winchester High School, with easy access to local shops, restaurants, and major routes. A wonderful opportunity to enjoy comfortable living in highly desirable Winchester!

3 Beds ⋅ 4 Baths ⋅ 73571573 MLS

Great opportunity to live on a quiet side street conveniently located near the town center and Elizabeth C. McDonald Field, featuring tennis courts, ball fields, basketball courts, and a playground. This well-maintained 3-bedroom, 3.5-bath townhouse offers 1,225 sq. ft. of comfortable living space. The charming home features high ceilings and a functional multi-level layout with a bright living area, spacious kitchen, two generously sized bedrooms, and a large office. Numerous updates were completed in 2023, including hardwood flooring, a finished attic, five ductless mini-split AC units, and renovated bathrooms. A new roof was installed in 2024. Additional updates include a high-efficiency gas boiler and hot water system installed in 2019. Conveniently located within walking distance to the newly built Lynch Elementary School and Winchester High School, with easy access to local shops, restaurants, and major routes. A wonderful opportunity to enjoy comfortable living in highly desirable Winchester!

23 Shepard Ct Unit 23, Winchester

Listing courtesy of Listing Agent: Ning Sun from Listing Office: United Real Estate, LLC.

$319,000

Best Price 1 Bedroom at The Parkview in Winchester! An exceptional opportunity to own in Winchester at an accessible price point! This first-floor, one-bedroom Terrace level at The Parkview offers an unbeatable combination of convenience, affordability, and practical living. Positioned on the ground level for easy direct access, the unit features peaceful views of the scenic duck ponds and mature, green landscaping. Step inside to an efficient open-concept layout where the kitchen features a functional peninsula and brand-new, never-used stainless steel appliances. All inclusive monthly HOA fee. Perfect for budget-conscious buyers, investors, or downsizers, completely covers your major monthly utility expenses: heat, hot water, electricity, water/sewer, and central air conditioning. In an era of rising utility costs, this structure provides total peace of mind and simplified monthly budgeting. Residents also enjoy access to the community pool, outdoor picnic grounds, and ample open parking. The location provides premium convenience, situated just minutes from vibrant Winchester Center with its local shops, cafes, highly rated restaurants, and two MBTA commuter rail stations for a straightforward commute. Enjoy everything Winchester has to offer, from the acclaimed public school system to the nearby trails of the Middlesex Fells Reservation, alongside quick access to Route 3 and I-93. If you have been searching for a smart entry into a high-demand market or a turn-key rental property with highly predictable expenses, this unit delivers outstanding utility and location for the price. ~DIRECTIONS TO UNIT~ park in lot to the right and walk to the rear of the building (the part with the duck ponds) it is a terrace level with its own door unit T-14

1 Beds ⋅ 1 Baths ⋅ 73580409 MLS ⋅ ['Parkview'] BLDG.

Best Price 1 Bedroom at The Parkview in Winchester! An exceptional opportunity to own in Winchester at an accessible price point! This first-floor, one-bedroom Terrace level at The Parkview offers an unbeatable combination of convenience, affordability, and practical living. Positioned on the ground level for easy direct access, the unit features peaceful views of the scenic duck ponds and mature, green landscaping. Step inside to an efficient open-concept layout where the kitchen features a functional peninsula and brand-new, never-used stainless steel appliances. All inclusive monthly HOA fee. Perfect for budget-conscious buyers, investors, or downsizers, completely covers your major monthly utility expenses: heat, hot water, electricity, water/sewer, and central air conditioning. In an era of rising utility costs, this structure provides total peace of mind and simplified monthly budgeting. Residents also enjoy access to the community pool, outdoor picnic grounds, and ample open parking. The location provides premium convenience, situated just minutes from vibrant Winchester Center with its local shops, cafes, highly rated restaurants, and two MBTA commuter rail stations for a straightforward commute. Enjoy everything Winchester has to offer, from the acclaimed public school system to the nearby trails of the Middlesex Fells Reservation, alongside quick access to Route 3 and I-93. If you have been searching for a smart entry into a high-demand market or a turn-key rental property with highly predictable expenses, this unit delivers outstanding utility and location for the price. ~DIRECTIONS TO UNIT~ park in lot to the right and walk to the rear of the building (the part with the duck ponds) it is a terrace level with its own door unit T-14

200 Swanton St Unit T14, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.