Homes for Rent near Winchester High School

Experience luxury living in this beautifully renovated 2-level townhome in the coveted Willows at Winchester community. This rare 3 bed, 2.5 bath residence offers an open layout with gleaming hardwood floors, a chef’s kitchen, dining area, and a spacious living room with gas fireplace and access to a private deck — perfect for entertaining. Upstairs features all bedrooms, including a luxurious

William Natoli Compass

No equal. Stunning, newer construction luxury Penthouse available for rent. Elevator access steps from private, heated, two (2) car garage parking completes the 2,900 square feet of open, fabulous, three (3) bedroom, two and half (2-1/2) bath space. Ten (10') foot ceilings throughout this airy, bright, light filled remarkable residence. Exquisite hardwood floors compliment the generous white trim

Anthony Marino The Marino Group Collection

Welcome to 7 Conant Road! This unit offers a spacious open floor plan with 1,338 square feet, featuring two bedrooms and two full bathrooms, including a roomy primary suite. Enjoy open concept living with nice flow from the kitchen to the living room & dining area. Updated & move-in ready, the bedrooms are large, complete with generous closet space. This rental showcases modern charm with an

Kim Covino Compass

Location, Location, Location!! This beautifully updated 2 bedroom 2.5 bath conveniently located in Winchester Center. Recently renovated, this unit boasts a stunning kitchen with farmer sink, high end stainless appliances, custom cabinetry and pantry. First floor offers living room w/ fireplace and large dining room with hardwood throughout. 2 spacious bedrooms and 1.5 baths complete the second

Kim Covino Compass

This beautifully maintained one-bedroom condo at Parkview offers exceptional value in Winchester—one of Massachusetts’ most desirable towns. Conveniently located within the building, this bright and inviting unit features a stylish kitchen with granite countertops and modern cabinetry, plus a renovated bathroom with contemporary finishes. Enjoy peaceful views from the private balcony. The

Alex Wang Hestia

A grand home with a perfect mix of serenity and entertaining spaces. The main level has endless possibilities with its ability to provide cozy living areas and also an open concept with great flow. Fully equipped modern kitchen with tons of storage and island, Formal dining room with custom built ins, french doors to separate or open up spaces, front to back fireplace between the massive family

Sheri O'Connor Plunkett Properties

A rare find! Newer construction rental home/ attached single family/ featuring 5 bedrooms & 4 baths over 4 finished levels, close to Winchester center and Muraco Elementary School. This great home features large spacious rooms, a sunny granite kitchen w/ maple cabinets, hardwood floors/ open concept w/ family room & a gas fireplace w/ sliders that lead to a spacious deck overlooking a fenced in

Kim Covino Compass

Welcome to this charming, sun-filled 2-bed, 2-bath home in the heart of Winchester. With nearly 900 sq. ft. of living space, it blends classic New England charm with modern convenience. The house comes fully furnished—down to the silverware, linens, and decor—so you can simply unpack and relax. Enjoy hardwood floors, a bright living room, a modern kitchen with upgraded counters, and a private

William Dynan Keller Williams Realty Evolution

Sunny 2-Bedroom in Winchester! Beautifully maintained 5-room apartment featuring 2 bedrooms, 1 bath, and parking for 2 cars. This first-floor unit offers gleaming hardwood floors throughout, a bright kitchen with dishwasher and spacious pantry, and a dining room with built-in cabinet and charming chandelier. Two generously sized bedrooms with closets, a full bath, and both front (enclosed) and

Danielle Storella Berkshire Hathaway HomeServices Commonwealth Real Estate

Experience refined New England living in this elegant single-family home in Winchester, Massachusetts—an enclave of luxury just eight miles north of Boston and minutes to Cambridge. This light-filled, impeccably maintained residence blends sophistication and comfort with open living and entertaining spaces. The gourmet kitchen with stainless steel appliances and granite countertops flows into a

Helen Stefan Gibson Sotheby's International Realty

Grand and masterfully crafted home on this private road abutting 2200 acre Fells conservation land. This spacious home has 6 bedrooms, and 5 bathrooms. The stunning foyer welcomes you to the sprawling first floor. The custom work throughout each sun filled room is exquisite. Gourmet kitchen with top of the line appliances. Generous sized rooms to entertain guests. A private home office with built

Dylan Archambault Archambault Real Estate

Spacious top floor 1 bedroom with private deck with stunning pond views. Convenient location to public transportation, shopping and restaurants. Heat, hot water and electricity included. Laundry and extra storage in the building. 1 parking spot. No smoking and no pets.

Brunna Henrique Keller Williams Realty Boston-Metro | Back Bay

An elegant property on one of Winchester's most beautiful residential side streets, facing the Middlesex Fells, with breathtaking seasonal views of the reservoir. Feels like a wooded retreat! Features 4 BR, 3 full BA; granite & stainless kitchen; a huge open-concept living area with 10ft+ ceilings, grand fireplace & wet bar; secluded screened patio, deck. Hardwood floors, designer light fixtures.

Robyn Bonnett Coldwell Banker Realty - Lexington

Great two bedroom with hardwood floors, super sunny, updated kitchen and bath, in unit laundry, central A/C, good size bedrooms, one off street parking spot. Great location. 9/1 move in no pets.

Kristen Day RE/MAX Realty Plus

FURNISHED ONLY 3 MONTH WINTER RENTAL. If you’ve been thinking of a kitchen renovation or addition but dread the chaos of construction, or maybe you're visiting one of our world renowned hospitals, our stunning 5-bedroom, 3.5-bathroom, 3,500-square-foot home in the coveted Muraco school district is available for a 3-month winter rental (January through March) while my family snowbirds in Florida.

Michael Gilbert Stuart St James, Inc.

Single Family Home Rental in Winchester. NO BROKERS FEE. Available 11/1 or 11/15. Completely rebuilt from ground up in 2019 w/Attached 1 Car Garage. 4 Beds, 3.5 baths & 3500SF w/ 2 dedicated home offices. Modern kitchen w/Quartz Countertops, Stainless Steel Appliances & Venting for cooking. Open concept has an Island connecting dining & living spaces. Sundrenched Living Room offers a wood burning

Collin Bray Century 21 Cityside

No Broker Fee! Large Sun-filled Windows, Contemporary, Minimalist, and Modern Design. A truly rare opportunity to rent this magnificent single-family home in one of Winchester’s most desirable neighborhoods. The home was ground-up construction in 2010 with over 3,500 square feet of living space. Its open concept, large loft-style office / second living room area, four bedrooms, three and a half

Frank Celeste Gibson Sotheby's International Realty