Recently Sold Winchester Highlands Homes

Charming turn-of-the-century 5-bedroom Gambrel-style home in move-in condition, blending classic character with modern updates. This spacious residence features a beautifully updated interior with central air, a stunning primary suite with private bath, custom closet system, and generous living spaces throughout. The detached 2-car garage adds convenience, while the location offers unbeatable

Pirani & Wile Group Advisors Living - Winchester

Located in a beautiful neighborhood, this thoughtfully renovated 3-bed, 2-bath home with a custom built free standing office/cottage/gym/ movie house, blends timeless charm w/ modern comfort. Sunlight pours into the open living spaces, highlighting original details & gleaming refinished hardwood floors. The inviting living room features a cozy fireplace w/ built ins, the dining room is perfect

Kim Covino Compass

Looking for the ideal first home or a peaceful place to settle into your next chapter? This charming 3-bedroom, 2-bath home, nestled at the end of a quiet dead-end street, was completely remodeled in 2009. Step inside to a warm and welcoming space with a practical layout—everything you need without the fuss. Whether you're just getting started or looking to simplify, this move-in-ready home is a

Rodrigo Serrano Leading Edge Real Estate

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.

Rodrigo Serrano Leading Edge Real Estate

Great Two-Family Home in a Desirable Location! This well-maintained two-family property features a total of 4 bedrooms and 2 full bathrooms, with beautiful hardwood floors throughout. Each unit offers spacious living areas filled with natural light. The basement includes laundry hookups with washer and dryer included. Enjoy the convenience of 6 off-street parking spaces—a rare find! Situated just

Wei Wang WW Real Estate LLC

Don't miss this rare opportunity to own a charming home with an expansive yard on a quiet cul-de-sac street! This lovely 3-bedroom ranch is meticulously maintained and situated in the sought-after Muraco school district. The main floor features an eat-in kitchen, formal dining room, and a sun-filled living room with a fireplace, perfect for relaxing or entertaining. Gleaming hardwood floors run

Andersen Group Realty Keller Williams Realty Boston Northwest

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

Kim Covino Compass

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

Vantage Point Team William Raveis R.E. & Home Services

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

Kim Covino Compass

Tucked into the desirable Winchester Highlands and abutting the Middlesex Fells, 8 Ware Road offers space, comfort, and a flexible footprint. This well-maintained ranch features 3 bedrooms on the main level, including a primary suite with full bath, plus a finished basement with a spacious family room, walk-out sliding patio door, large flex space, & bonus 4th bedroom. The kitchen includes modern

Alex Navarro Coldwell Banker Realty - Beverly

Discover this beautiful split-level home featuring 4 spacious bedrooms and 2 bathrooms. The open floor plan seamlessly connects the inviting living room, dining area, and well-equipped kitchen, perfect for entertaining. Natural light floods the sunroom, offering a tranquil retreat that leads directly to a new deck ideal for outdoor relaxation. The main level boasts 3 bedrooms and a bathroom.

Robert Ellington Better Homes and Gardens Real Estate - The Shanahan Group

Delightful ranch, well maintained and located conveniently near the major routes. The kitchen is spacious and opens to the comfortable dining area with large built in hutch. It has been updated and features a tile backsplash, stainless steel appliances and recessed lighting. The living room is fireplaced and is nicely appointed with hardwood floors. Easy one level living with two first floor

Michael Barrett Barrett, Chris. J., REALTORS®

This charming home is move-in ready with many updates throughout, situated on a large fenced in level lot close to parks, the bike path, Muraco school & more! The interior of the home is flooded with sunlight & period details featuring open airy spaces and generously sized rooms that flow throughout the home, making each room easily accessible and enjoyable. The main floor has a lovely living

Kim Covino Compass

OFFER ACCEPTED - Open Houses CANCELED This stunning, sun-filled home welcomes you with a front porch facing southwest for sunset views! Move right in and enjoy so many updates - new windows, new kitchen, new shared bath, new heating and cooling systems, new exercise/mudroom, new landscaping and so much more!!! With fabulous detail and a focus on energy efficiency, this home will win your heart

Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

Nestled on a peaceful street surrounded by trees, this beautifully updated Cape home offers a perfect blend of comfort and character. Located just moments from the scenic Middlesex Fells Conservation Area, you'll have miles of trails for outdoor exploration right at your doorstep. With a commuter-friendly location, this home is ideal for those seeking both tranquility and convenience. A welcoming

Andersen Group Realty Keller Williams Realty Boston Northwest

Welcome home to this architect designed 3 plus bedroom, four bath custom cape! Spacious rooms within a contemporary layout plus amenities like central air, 1st floor laundry room, direct indoor access to a 2-car garage, and delightful wooded back yard are more outstanding details. The kitchen & family room at the back of the house will be everyone’s favorite gathering spot. The eat-in kitchen

Andrea O'Reilly Keller Williams Realty Evolution

Introducing 74 Hillcrest Parkway! This spacious, modern 5-bedroom home is nestled across the breathtaking Middlesex Fells Reservation on one of Winchester's most picturesque streets! First floor seamlessly blends living, dining, & kitchen areas. Living room has wood burning fireplace & custom built-in shelves. Dining room offers delightful space for cozy gatherings and the spacious eat-in kitchen

Ann Hogstadius RE/MAX Real Estate Center

Nicely updated home in desirable Muraco district! This home has been meticulously maintained & features many recent updates including newer windows, central air conditioning & updated systems. Enjoy the sun drenched spaces from the spacious living room w/ fplc & bay window to the charming dining room w/ china cabinet, sunny eat-in kitchen, office, plus 3 season porch & 1/2 bath complete the first

Kim Covino Compass

Nestled in a desirable neighborhood, this home offers the opportunity to embrace the timeless elegance of the mid-century era. Lovingly maintained in its original condition, the ranch style provides the coveted option for one-level living. Enter the main level into the fireplaced living room, with large picture window and hardwood floors. Adjacent to the kitchen is the dining room with hardwood

Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group

Welcome to this charming Colonial, thoughtfully maintained by its owners! Nestled on a peaceful, tree-lined street, this beautifully updated colonial home exudes warmth and character. Featuring a recently updated roof (2022), new triple pane energy efficient windows with transferable lifetime warranty (2018), and fresh interior and exterior paint, this home is move-in ready and full of charm.

Andersen Group Realty Keller Williams Realty Boston Northwest

Exquisite 6-bed, 6.5-bath residence offers 6,300 sq ft of sophisticated design and luxurious features. The chef’s kitchen boasts dual islands, quartz countertops, Viking appliances, and a sunny breakfast nook perfect for entertaining. The family room with a gas fireplace opens to a deck and landscaped yard for seamless indoor-outdoor living. The first floor includes a guest bedroom or office with

Monte Marrocco Coldwell Banker Realty - Lexington

Nestled at the end of a peaceful cul-de-sac in Winchester, this charming 3-bedroom, 1.5-bath home is a must-see. Recently updated with fresh paint, modern flooring, stylish lighting fixtures, and updated stainless steel appliances in the kitchen, it blends comfort with convenience. The living room features a cozy wood-burning fireplace, perfect for chilly evenings. The walk-out basement offers

Gayle Winters Compass

Welcome to this impeccably maintained & beautifully updated Colonial on large lot near the town center. This home blends charm w/ modern convenience, featuring 3 spacious bedrooms & 1.5 baths w/ a great floor plan. The first level features a sun-drenched living room that flows into an inviting dining room; updated kitchen overlooks the rear yard & is equipped w/ ample storage, stainless steel

Kim Covino Compass

DON'T MISS THIS ONE! Ideal location at Waterfield Square - This spacious one bedroom is a diamond-in-the-rough waiting for your upgrades. High ceilings and huge windows bring in lots of sun and light. Open floor plan. Lots of closet space. Washer & Dryer in unit. Deeded parking, basement storage, tennis court, picnic area with grill, fire pit, located across from the North Reservoir and

Diane Plunkett Plunkett Properties

Beautifully renovated home with open concept main living area including elegantly updated kitchen with quartz countertops, professional grade range and wine refrigerator. Primary suite includes cathedral ceilings and oversized (8' high) sliders opening up to private balcony with views of Leonard Pond. His and hers closets and private bath with double sinks and radiant heat make this the perfect

Amanda Armstrong Compass

Discover this rare multi-family gem in a highly desirable Winchester neighborhood, offering endless possibilities for savvy investors, owner-occupants, or multi-generational living. Situated on a large, flat, private lot with a detached two-car garage and ample off-street parking, this home perfectly balances charm, function, and convenience. The first-floor unit includes two bedrooms, a bright

Nancy Pallotta Advisors Living - Winchester

Exceptionally designed & meticulously maintained 2015 Contemporary Colonial. Elegant farmers porch welcomes you into a magnificent layout w/ exquisite mouldings, wainscotting, oak hardwoods, custom fixtures/millwork, & plantation shutters. Spectacular, open-concept main level boasts dual island, granite/stainless chef’s kitchen w/ 2 ovens, butler’s pantry, built-in buffet, walk-in pantry, &

Cam Chesley Keller Williams Realty Boston-Metro | Back Bay

Welcome to this well-maintained two-unit multi-family home, perfect for investors or owner-occupants seeking a spacious living arrangement with rental income potential. Each unit boasts two well apportioned bedrooms and dedicated in-home office areas, ideal for today’s work-from-home lifestyle. Enjoy the convenience of off-street parking along with two garage bays, ensuring easy access for you

Anne Spry Barrett Sotheby's International Realty

This thoughtfully updated home combines historic charm and modern style. The oversized, beautifully landscaped lot showcases established plantings, charming stone paths, and terraced gardens - the perfect oasis for relaxing family time and outdoor entertaining. Inside, the hub of this 5 BR, 3,5 BA home is the large, open-concept kitchen and family room, featuring a cathedral ceiling, gas

Jay Smith Brad Hutchinson Real Estate

Exquisitely renovated down to the studs and close to completion w/ over 3,000 sq ft in a great neighborhood! The home offers 4 Bedrooms + Loft, 3 full and 2 half baths w/ designer tile, 6"wide hardwood floors on all 3 living levels. First floor has an open floor plan and great flow for entertaining. Large eat-in Kitchen with island, Quartz counters and SS appliances. Stepdown to a huge living

Lisa Simmons William Raveis R.E. & Home Services

Your wait is over! Brand New Townhouse with a stylish flair has just been completed and is ready for YOU to call it HOME! Located just minutes away from all the amenities in Winchester and major highways. This flexible use floor plan offers an open floor plan on the 1st floor with a spacious well appointed kitchen, dining area, living room, mudroom and half bath. The 2nd floor features the

Bill Copithorne Keller Williams Realty Boston Northwest