Recently Sold Winchester Highlands Homes

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

A Brand New Townhouse with a modern stylish feel has just been completed and is ready for a new owner to make it their Home! Located just minutes away from all the amenities in Winchester Center you could not ask for a more convenient location. You will be wowed as you cross the farmer's porch into the well designed open 1st floor that features a custom FP in the living room, built-in bench

Bill Copithorne Keller Williams Realty Boston Northwest

Welcome to your sprawling retreat nestled on an expansive lot, offering unparalleled versatility for recreation and relaxation. This magnificent property boasts 27,952 square feet lot with an inground pool. Whether you're hosting barbecues by the cabana, or enjoying a morning swim, this outdoor oasis offers endless possibilities for lifelong memories. The 4,234 square foot home, proudly owned and

Anne Spry Barrett Sotheby's International Realty

Aah, the beautiful summer weather is here. We wait all year for this, and the level yard at 19 Kenwin Rd is sunny and lush and ready for you to enjoy your outdoor living. Sited on more than a quarter acre, this 9-room 3-bed 2-bath colonial is located just a mile to vibrant Winchester Center, and one block to Middlesex Fells Reservation, a 2,575 acre natural haven. The main floor has 5 rooms

Judy Weinberg Leading Edge Real Estate

Lovingly maintained family home on a gorgeous oversized lot with beautiful perennial gardens, and an abundance of privacy bound by beautiful mature landscape. This custom built 4 bedroom home is awaiting your personal touch. Create the home of your dreams with this extraordinarily spacious layout featuring a rear family room addition plus glass enclosed heated sunroom overlooking the beautiful

Kim Covino Compass

Cherished home located on a quiet side street in Winchester Highlands, close to the popular Fells Reservation. Flexible layout perfect for today's living with 5 beds & 3.5 baths. The 1st floor features a formal living room with fireplace, expansive family room & open concept dining room/kitchen with new appliances, cherry cabinets and beverage cooler. Two 1st floor bedrooms and a full bath

Paul Cirignano The Synergy Group

Don’t miss this meticulously maintained, beautifully renovated home~ move right in & enjoy! This great home is situated on an adorable lot with patio, perfectly sized yard & garage. High ceilings throughout w/ a large sun drenched living room which flows seamlessly into the dining room, featuring sliding glass doors opening to a charming 3-season sunroom. The large eat-in kitchen offers cherry

Kim Covino Compass

Welcome to this charming renovated home on a lush oversized lot in a super convenient location near Muraco School. This updated 3-bedroom, 2.5-bathroom home w/ A/C offers a perfect blend of modern finishes & original old world detail. Inside you'll find a beautifully renovated, open concept kitchen with stainless steel appliances, quartz counters, pantry & plenty of prep space open to a dining

Kim Covino Compass

Welcome to your next home! Classic 1930s Colonial nestled just steps away from the serene Middlesex Fells Reservation. Convenient access to 93 & 95, minutes from downtown Boston & within close proximity to town center, commuter rail & schools. Plenty of upside and possibilities here. Live in as-is or create your own vision for this lovely 3 bed, 1 bath home. Upon entry, a lovely foyer invites you

Pirani & Wile Group Advisors Living - Winchester

Presenting Winchester’s newest luxury new construction home, 4 Abby Road. The first floor features a formal dining room, fireplaced family room, and an eat-in kitchen with a gorgeous island & wet bar. The large mudroom, conveniently located off the garage, provides seamless access to the home. Additionally, a private home office just off the mudroom makes a serene space for work or study. The

Philip Vita Compass

Introducing 19 Churchill Road! This inviting home offers 3-4 bedrooms, 2 bathrooms, and 2 levels of spacious living area. The cozy living room and family room each boast a wood-burning fireplace, perfect for creating a warm and inviting atmosphere for every member of the family. The dining room is ideal for hosting intimate gatherings, while the eat-in kitchen offers a delightful space for casual

Philip Vita Compass

OPEN HOUSE CANCELLED! Welcome to this adorable 4 bed, 2.5 bath home with a fenced in yard! ~10K seller credit!! This property features a large family room with a beautiful fireplace, an attached sunroom or perfect home office, spacious dining room & updated kitchen w/ gleaming hardwood floors and high ceilings throughout the home. For guests, or a 1st floor primary option there is a first floor

Kim Covino Compass

A home like no other for the true nature lover! Feel the love at 22 Fells Road perched up high on a pretty street in the Highlands area of Winchester that is tucked away yet close to area amenities. A true sanctuary that one can only dream of just steps from The Middlesex Fells Reservation (bike or hike on endless trails that go on for miles) & offers the most magnificent sunsets from the treetop

Nancy McLaughlin Redfin Corp.

This spacious home with thoughtful design details was carefully maintained through the years by original owner/builder. On first floor, be welcomed to a large living room with fireplace (plenty of space for multiple seating zones/uses), the dining room has custom built in storage that can be removed, half bath, enclosed porch and beautifully designed kitchen with eating area and bright sunny

Elizabeth Darby Berkshire Hathaway HomeServices Commonwealth Real Estate

Charming 1930's Cape with arched doorways, built-ins, period details and several recent updates. Located in the desirable "Highlands" section of Winchester and within walking distance of the Muraco Elementary School, Leonard Field, the Fells Reservation and Winchester Hospital . Enjoy spacious rooms with several improvements including a striking remodeled eat in kitchen with white cabinets,

Judith Moore Barrett Sotheby's International Realty

Modern luxuries & exquisite finishes! This impeccably renovated 5 BR 3 ½ BA home showcasing infinite high-end details is located just outside the Middlesex Fells. The centerpiece is the expansive chef’s kitchen featuring custom cabinetry, marble countertops/island, 6-burner Wolf cooktop, double ovens, Sub-Zero fridge, beverage center & dining area. The open floor plan seamlessly connects the

Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

Lovely 4 bedrooms, 2 baths unit. The updated three level unit features a great layout, front porch and a beautiful foyer welcome you upon entry to the property. Plenty of windows bringing in great light and gorgeous hardwood floors throughout. Elegant living room with gas log fireplace. Spacious kitchen with reset lighting and view to a private fenced backyard. Spacious back porch, great place to

Waterfield Square Condominium, located across from the North Reservoir and the Middlesex Fells Reservation, miles of hiking and bike trails. This turnkey unit has large new windows with remote driven blinds and faces the reservoir on the sunny side of the building. The floor plan is open and the high ceilings make it feel spacious. Designated one parking space and storage in the common basement