luxury properties for sale Winchester, United States

Rare waterfront living on the Mystic Lakes. This exceptional, secluded residence offers a lifestyle centered around nature, relaxation, and creating generations of memories. Filled with natural light and stunning water views, the home features spacious living and dining areas ideal for everyday living and entertaining. The family room showcases a dramatic picture window overlooking the water with access to a deck perfect for gatherings. A well-appointed kitchen and dedicated home office add comfort and functionality. Upstairs are more than four spacious bedrooms including a beautiful primary suite retreat. A third-floor artist studio and expansive basement workshop offer exceptional flexibility. For the car enthusiast there is a four car garage . Enjoy decades of memories and a legacy lifestyle steps to the water invite kayaking, paddleboarding, boating, fishing, and year-round enjoyment of this extraordinary waterfront setting. Convenient to Cambridge and beyond.

Perched high atop an Arlington Hill, this custom home invites a slower rhythm. Think sunsets from the farmer’s porch, chirping birds in the garden, and light that moves beautifully throughout every space. Built in 2008 and thoughtfully elevated since, its construction and solar efficiency shine in both form and function. Soaring ceilings in the entryway and a natural sense of balance reflect throughout the open floor plan. The kitchen invites gatherings with friends and family, opening seamlessly to a deck and dreamy side yard. The main level offers a harmonious balance between connection and retreat, while upstairs features four bedrooms, including a primary suite with spacious sitting area and bathroom featuring a soaking tub, with laundry room nearby. An unfinished lower level is ripe with potential, third-floor attic offers additional opportunity for expansion and the two car garage keeps life organized. Set on a quiet cul-de-sac, lifestyle and location align, just minutes to the bike path and Mass Ave!

Adorned with timeless details and character at every turn, 82 Richfield Road is a truly distinguished property that has been meticulously cared for by the same owners for nearly 30 years. Original wood detailing and archways immediately set the stage upon entry into the foyer, with its elegant staircase, and into a sophisticated library with rows of built-in bookshelves, beamed ceilings and electric fireplace. The main level continues to an updated kitchen with high-end appliances, double oven, granite counters, large center island and a versatile wet bar with additional storage before leading into a formal dining room and an oversized living room with wood-burning fireplace. The second floor features three bedrooms, a modern full bath and an office, but it does not end there. A fully finished third level has two additional bedrooms with cathedral ceilings and a full bath with double vanity. Enjoy the outdoors on your back patio, covered side porch or on the nearby bike path.

Rare opportunity in the heart of West Medford! This traditional Colonial, set on a large private lot, offers exceptional potential for developers, investors, or buyers with vision. Currently zoned GR, the property presents the strong possibility for 2 units with street frontage on both Sharon and Sherman Streets. Historic Commission approval for removal has already been obtained by the owners. Ideally located with easy access to Cambridge, Boston, and Tufts University, while also convenient to the MBTA Commuter Rail with direct access to North Station. Enjoy nearby shops, restaurants, and the vibrant West Medford neighborhood. Whether restoring the existing home or pursuing redevelopment, this is a unique opportunity in a prime location.

Perched high above the treetops on a horseshoe street in coveted Jason Heights, life here feels calmer, prettier and deeply connected to nature. With Menotomy Rocks Park at the end of the street, morning walks, birdwatching, skating on the pond and sunset strolls become part of your daily rhythm. Thoughtfully redesigned, this gracious 1930’s home beautifully blends timeless charm with today’s modern lifestyle. The sunny kitchen is the heart of the home, featuring crisp white cabinetry, an island, SS appliances and seamless flow into the dining room. A fireplaced living room invites cozy evenings while the screened slate porch and outdoor hot tub feel like a private retreat! Upstairs are four spacious bedrooms including a primary suite with spa-like bath and custom walk-in closet + a very cool teen suite that feels like a treehouse with bedroom, sitting room and remodeled bath. Owned solar panels, a 2023 roof and 12,000+ square feet make this spot ideal + just mins to the amenities that the Center has to offer!

Terrific Lexington home! This pristine Colonial on a side street has been meticulously maintained by the current owners and it shows! From pretty hardwood floors to newer systems, replacement windows throughout, newer roof, insulation added, renovated baths, AC added with mini-splits, and so much more. Enjoy the welcoming living room with cozy fireplace, formal dining room, remodeled kitchen and powder room leading to 3 good size bedrooms and an updated bath on the second level. You’ll appreciate the bonus flexible living space in the finished lower level family room, office area, full bath and storage. Enjoy summer activities and relax on the deck in your private backyard. A welcoming home in a quiet Lexington neighborhood with easy access to the bike path, Great Meadows trails, swimming at the Arlington Res Beach, shopping, restaurants and public transportation. Welcome to your new home!

Set in an idyllic location abutting Robbins Farm/Skyline Park, this exceptional three bedroom, two and a half bath home offers a rare combination of privacy, beauty and modern convenience. Inside, a stunningly renovated kitchen anchors the home, complemented by a sweet mudroom, full bath and the warm inviting living room with fireplace and charming dining. Upstairs, three well-appointed bedrooms and a full bath are surrounded by serene treetop views from every window, creating a peaceful retreat. The semi finished basement offers added versatility with a 1/2 bath, ideal for a home office, playroom, or workout space. Great storage in huge attic and basement. From your backyard, enjoy breathtaking sunrises, front-row views of seasonal fireworks and direct access through your own private gate to the park’s beloved sledding hill, playground, and park activities - an extension of your own outdoor space. Close to Brackett School, Mass. Ave. busses, and all the shops and eclectic eateries of the Heights and Center.

A rare gem in Jason Heights, this Craftsman style Colonial blends timeless character with exceptional craftsmanship and thoughtful renovation. Rich in detail, from the original inglenook and stained-glass windows to custom built-ins throughout, the home feels both elegant and deeply inviting. A gracious porch and welcoming foyer lead to a beautifully renovated kitchen overlooking extraordinary gardens, seamlessly connected to the dining room with stunning chandelier and an intimate den. Sunlight pours through expansive windows, framing serene views in every direction. The second floor features a luxurious primary suite with dressing area, custom storage, soaking tub, and separate shower, along with two additional bedrooms and a beautifully appointed bath with claw-foot tub. The walk-out lower-level impresses with a dramatic family room opening to a screened porch, patios and enchanting established gardens. Multiple decks, extraordinary woodland garden, and an unbeatable location!

Nestled in Arlington's coveted Jason Heights neighborhood, this distinguished five bed, three bath residence offers over 4,000 square feet of timeless elegance, architectural character, and exceptional living space. Filled with natural sunlight, the home showcases beautiful hardwood floors, original period craftsmanship, elegant moldings, and a striking fireplace that anchors the main living area. Generous rooms and a versatile floor plan provide the perfect setting for entertaining, working from home, or accommodating extended family, while preserving the warmth and charm of a bygone era. Outside, an expansive yard offers a peaceful retreat for gardening, recreation, or outdoor gatherings, while a detached one-room summer cottage presents endless possibilities as a studio, home office, or private sanctuary. Just moments from Menotomy Rocks Park and its scenic walking trails, this rare offering presents an opportunity to own a truly special home in one of Arlington's most treasured neighborhoods.

Full of charm, beautiful woodwork, and thoughtful modern updates, this stunning three bedroom, one and a half bath home in Medford’s Lawrence Estates neighborhood offers the perfect blend of timeless character and modern comfort. Rich hardwood floors and classic architectural details create a warm and inviting atmosphere throughout the home. Designed for today’s lifestyle, the home features a finished lower level offering flexible living space, along with a wonderful mudroom and bright office filled with natural sunlight. The updated full bathroom includes radiant heated floors, adding an extra touch of comfort and luxury. Thoughtful updates throughout enhance the home’s charm while preserving its unique character. Outside, the lush backyard provides a private retreat perfect for relaxing or entertaining, complete with an in-ground sprinkler system. 31 Whittier Rd is a truly special home offering warmth, functionality, and timeless appeal in one of Medford’s most admired neighborhoods.

A beautifully maintained home in an exceptional West Medford location, offering the perfect blend of charm, comfort and convenience. Tucked away on a side street just moments from West Medford Square, the commuter rail, parks, shops, restaurants and easy access to Boston, this inviting home is sure to delight. Bright, open and airy spaces create a warm and welcoming feel throughout, including a wonderful family room open to kitchen, three comfortable bedrooms, flexible guest or work-from-home space, plus sliders to a great deck and private yard perfect for relaxing, gardening and entertaining. An attached garage adds everyday convenience, while thoughtful updates throughout, including central air, newer windows, custom shades and low-maintenance shingle style vinyl siding, make living easy. Full of character, natural light and meticulously cared for inside and out, this move-in-ready home balances timeless appeal with modern functionality. Enjoy visiting nearby Fells and Mystic River!

28 years ago, the owners searched for just the right house to make their home and if these walls could talk, they’d tell a story of love, laughter and beautiful, real life moments. Architecture and artistry converge in a striking '09 addition, creating a unique turret-style den, with cozy fireplace, an intimate feel and easy connection to the kitchen framed by windows. Step outside and it's even more magical - a blend of patio, play space, and perennial gardens feels like quiet escape, almost like being on vacation. The main level was designed with purpose, every space enjoyed, from the fireplaced living room to countless holidays around the dining table. A little office doubles as a pantry connects to the lower level, offering flexible media/play space with direct garage access. Upstairs, the primary suite features a gorgeous bath, two additional bedrooms, a main bath with laundry, + walk-up attic. Set across town greenspace and surrounded by mature trees, this gem is just minutes to Skyline Park and Brackett!

This thoughtfully designed home offers space, comfort, and versatility for today’s lifestyle. The first floor features an open layout with formal and informal living areas, including a living room, dining room, and kitchen with warm wood cabinets, granite counters, stainless steel appliances, island with breakfast bar, built-in desk, and dining nook. The living room has a gas fireplace, custom built-ins, and deck access, perfect for entertaining or relaxing. A first-floor bedroom and full bath provide flexible living options for guests or multigenerational needs. Upstairs, the primary suite includes a tray ceiling, walk-in closet, and en-suite bath, alongside three bedrooms, full bath, and laundry room. The finished third floor offers bonus space for a family room, gym, or extra bedroom. High-efficiency systems, a low-maintenance exterior, abundant natural light, and a desirable neighborhood make this home ideal for modern living.

If you lived here, you would have the Minuteman Bikeway at one end of your street and the 183-acre Great Meadows at the other. Public transportation, restaurants and shopping are only a couple of blocks away and Wilson Farm is down the street. This charming 1925 Colonial with welcoming front porch features an open first floor that includes a family room with vaulted ceiling and sliders to a deck and level yard, a playroom or study with built-ins plus an open living room, dining room and kitchen. Upstairs, find three bedrooms, an updated bath with tub and separate glass shower and a walk-up unfinished attic. With a separate entrance, former second kitchen, full bath and three additional rooms including a music/exercise room, the lower level can fulfill many needs as a possible in-law apartment, in-house office or additional personal space. Recently updated kitchen appliances, furnace and hot water tank, front & rubber roof and new deck complete the picture. Welcome home!

Discover this exceptional Arlington Heights home, offering space, style, and an unbeatable location near schools, shops and dining. A thoughtfully designed floor plan balances openness with distinct living areas, ideal for both everyday living and entertaining. The elegant library with custom built-ins creates a refined space for work or study, while the spacious kitchen flows seamlessly into the dining area, featuring built-in appliances, ample storage, and tasteful finishes. The inviting living room is perfect for gatherings, while the serene primary suite offers a luxurious retreat with a soaking tub, walk-in shower, and generous closet. A second private en suite bedroom is ideal for guests or teens, complemented by three additional bedrooms and a full bath. The lower level provides versatile space with a media room, fitness/play area, and access to patios, garden and a sports court! With ample room to expand, whether an ADU, pool, or garden, this home offers comfort and opportunity!

Have you been debating whether to tackle an addition or simply move? This stunner makes a compelling case for hitting the easy button. Set in the type of neighborhood where little ones learn to ride bike, this Heights gem blends location, new construction and energy efficiency with ease. Built in 2026, the thoughtfully designed layout reflects how people truly live today. At its heart, the kitchen steals the show with quartz counters, an island and tasteful brass accents, flowing seamlessly into the fireplaced living room, where glass doors open to a deck and perfectly sized yard. The mid-level features four spacious bedrooms, including a luxurious owner's suite with walk-in closet and spa-like bath, while the top floor offers an additional two room suite. Live with ease thanks to the attached two car garage, mudroom entry and finished lower level ideal for a gym, playroom or teen hangout. All in a coveted Dallin School location, just a stroll to Arlington Heights cafés, bikeway and the 77 bus to Cambridge!

Sometimes you can’t quite express what it is you love about a home, it just feels right. Interesting architecture and a sense of soul converge in this artist’s retreat. Tucked on a cul-de-sac near Tufts, with the MBTA Green Line T, Whole Foods and Fells trails just a short stroll away, this is where lifestyle and location truly align. Behind the beauty, the home was stripped to the studs in 2016 and rebuilt with all new energy-efficient systems, wiring, plumbing, windows and bathrooms. A 2018 kitchen remodel sets the tone for casual yet refined living on the open-concept main level. A flight up, you'll find a subway-tiled bath along with three spacious bedrooms, including a suite, pre-plumbed for future bathroom along with an office and separate dressing room. A treehouse-esque playspace on the top level feels worlds away, as it includes a bedroom and separate creator's loft. With enough classic charm to check all the boxes, and more than enough style, it’s the one you can’t wait to come home to!

Thoughtfully restored and beautifully updated, this exceptional property offers a rare opportunity to enjoy a piece of history in one of New England’s most historic towns. Ideally located adjacent to the Minuteman Bikeway and moments to Lexington Center, top-rated schools, the Waldorf School, Adams playground, and tennis and pickleball courts, this home blends convenience with privacy. Curated perennial gardens, fenced yard and multi-level mahogany deck create an ideal setting for entertaining or relaxing in a private garden oasis. Inside, grand ceilings, curved archways, rich millwork, hardwood floors and abundant natural light create bright, inviting living spaces. Open layout connects updated kitchen with island and separate butler's pantry to dining and fireplaced family room. Flexible bedroom layout includes a spacious primary suite with spa bath plus third-floor suite ideal for guests, office or extended living. Central air, gym and EV-ready garage complete this special home.

Tucked on a sunny corner lot in sought-after East Arlington, this storybook home blends charm, flexibility, and convenience. This two bedroom, one and a half bath home features a spacious living room, and a dining room just off the kitchen, perfect for easy, everyday meals and casual entertaining, and a dedicated home office, along with a bright, functional layout. A spacious kitchen with stainless steel appliances anchors the home, complemented by hardwood floors throughout and abundant natural light. A two car driveway adds everyday ease. Ideally located just moments to Somerville, Cambridge, and the best of East Arlington shops, restaurants, and bike paths. This home offers the perfect balance of comfort and connection. A true condo alternative.

Welcome to this well-maintained three-bedroom, one-and-a-half-bath home in one of Lexington’s most desirable neighborhoods. Lovingly cared for by its original owner, this property offers hardwood floors throughout all primary rooms & a thoughtful blend of charm & modern comfort. A front-to-back living room with a fireplace provides an inviting space for gatherings, formal dining rm for holiday gatherings while the well-appointed eat-in kitchen opens to a light-filled family room with direct access to the deck—perfect for summer barbecues. Upstairs, you’ll find a large multi-closet primary bedroom with direct access to full bath & two other spacious bedrooms. This is a wonderful opportunity to own a home that has been cherished for decades & is ready for it's next chapter. Conservation land & walking trails are at the end of the dead end street. Recent improvements: exterior painting & staining 2025, new windows 2024, new composite deck 2022, new fence 2021 & new oil tank 2019.

An exceptional newly constructed residence set within one of Lexington’s most coveted neighborhoods. Overlooking an expansive manicured lawn with ample space for a potential pool, the property abuts conservation land, offering a rare blend of privacy and seamless connection to the surrounding natural landscape. Soaring 10-foot beamed ceilings, rich hardwood floors and oversized windows create a dramatic sense of volume and light. Thoughtfully designed open-concept living features a chef’s eat-in kitchen complemented by a walk-in pantry, an elegant formal dining room and a spacious living room complete with wet bar, ideal for both everyday living and refined entertaining. Six en-suite bedrooms , Main-Level space suitable for a seventh bedroom or home office , Three car garage , Mudroom , Lower Level provides additional flexibility for a game room or fitness area. Just blocks from Lexington Center, offering access to all the town's amenities and major commuter routes.

A rare opportunity offering exceptional flexibility for living and working under one roof. This distinctive brick home features a versatile layout with generous living spaces, including a welcoming living room, dining room, kitchen and a comfortable family room with exterior access. The kitchen offers a functional dining area and flows easily for everyday living or entertaining. The layout presents options for a first-floor primary suite and additional bedrooms, while the lower level includes a walk-out space with a fireplace—ideal for recreation or extended use. With ample parking, an attached garage, and a prominent corner setting, the property is well-suited for a variety of lifestyles. This home has a special permit allowing a portion of the home may be used for a professional office, offering a unique live/work possibility. Floor plans available for both work from home office setting and as an expanded Cape. The 26,007 lot offers endless expansion opportunities.

Desirable Meriam Hill/Lexington Center location! You'll fall in love with this updated and expanded Cape with flexible living options that provide an ideal opportunity to live in historic Lexington just steps to the Minuteman Bike Path and vibrant downtown Lexington Center with restaurants, shops and more. Enjoy an updated kitchen with quartz countertops, a sun filled family room with cathedral ceiling leading to a private deck and the spacious backyard, an ample living room with fireplace, remodeled baths, newly refinished hardwood floors, freshly painted interior and a flexible floor plan with a first floor bedroom and office. Add all of this to the bonus potential living space in the unfinished lower level and you have a true rare find!