Winter Hill Homes for Sale

SPECIAL 3.75% FINANCING! LESS THAN A QUARTER MILE TO THE GREEN LINE! VICTORIAN 3 FAMILY CHARMER with GROWTH potential! INCLUDES DETACHED 2 STORY 856 SQ FT CARRIAGE HOUSE W/ LOFT which can be a FOURTH unit ADU (incl structural plans, sprinkler plans & contractor est). Units 1, 2, & 3 VACANT 6/30/2026 ($3600 Unit 1 potential rent / $3200 Unit 2 potential rent/ $2700 Unit 3 potential rent). Classic

Steve Bremis Steve Bremis Realty Group

Perched atop the historic crest of Winter Hill, this 2 bed/ 1 bath residence lives within a magnificent Mansard Victorian, a testament to the architectural grandeur of Somerville’s storied past. Inside, the heritage of the home meets modern grace. Soaring 10-foot ceilings and expansive windows bathe the open-concept living space in natural light, creating an airy sanctuary. The kitchen, finished

Patti Brainard Compass

A stylish, move-in-ready lifestyle condo in one of Somerville’s most vibrant urban neighborhoods. This updated home features new flooring, fresh paint, a 100% new kitchen with new countertops, new cabinets, and new stainless steel appliances, plus new AC units, an updated bathroom, and an updated electrical panel. Enjoy in-building laundry, pet-friendly living, and bike storage for added

John Dean Engel & Volkers Boston

Rare opportunity to own a well-located 4-unit property in the highly desirable Winter Hill neighborhood. Ideal for investors or developers looking to capitalize on strong rental demand and future long-term upside with rents currently below market. The property features a total of 6 bedrooms and 4 bathrooms across the four units, providing flexible living arrangements and consistent rental appeal.

Shane Marrion Benoit Real Estate Group ,LLC

Introducing a fully renovated and stabilized massive 6-unit building in the extremely desirable Winter Hill neighborhood of Somerville! This 8,060 sq foot building is nestled on a tree-lined one-way street and is directly across from the new Gilman Square green line stop and has a gross rent roll of $20,400 per month! The building has undergone extensive renovations including kitchen/bath/laundry

Lior Rozhansky Keller Williams Realty Evolution

NEW CONSTRUCTION...LAST UNIT LEFT...EXCLUSIVE USE ROOF DECK AND STUNNING PANORAMIC VIEWS OF BOSTON WITH A NON TANDEM GARAGE SPOT. Skylight, big windows, breakfast bar and designer bath...Less than a half to the Green Line!... Fantastic quality, incredible value...Stunning Sun Splashed Luxurious top flr unit has a beautiful livinig room with 9 ft clngs, skylight & custom paneled walls. Wide plank

Steve Bremis Steve Bremis Realty Group

A rare Somerville two-family on a quiet street in the heart of Gilman Square and at a price point that works for value-add buyers and owner-occupants alike. The 1st floor offers true flexibility: configure it as a 1 bed/1 bath or expand to 2 bed/1 bath with the existing pocket doors. Upstairs, you’ll find a spacious 4 bed/2 bath unit with both bathrooms completely gut renovated in 2015. Super

Sage Jankowitz Cambridge Sage Inc.

Fully gut-renovated two-family just ~0.3 mi to Gilman Square, offering a rare blend of design, flexibility, and location in one of Somerville’s most exciting neighborhoods. Thoughtfully curated with a well-balanced unit mix, Unit 1 features 2 beds/2 baths with private outdoor space and an effortless single-level layout. Unit 2 spans the upper levels with 3 beds/3 baths, offering a more expansive

Margie Gundersheim Commonwealth Standard Realty Advisors

Welcome to 355 Medford Street, Unit 1 an exceptional opportunity to own a spacious 2-bedroom, 1-bath condominium in one of Somerville's most convenient locations. Priced to sell this home offers outstanding value for buyers seeking comfort, convenience, and easy access to everything the city has to offer.This well-appointed condo features a functional floor plan, generously sized bedrooms,

Kurt McLaughlin Greater Investments

Discover elevated urban living at 115 Thurston Street, a stylish 3-bedroom,2-bath penthouse condo in Somerville’s desirable Winter Hill neighborhood. This newer construction residence combines modern architecture with sophisticated finishes, featuring sun-filled interiors,9-foot ceilings, custom millwork and an open-concept layout designed for contemporary living.The designer kitchen features

Laura DeLuca Compass

Presenting a distinguished multi-family at 7 Stickney Ave, Somerville, MA. This expansive 1920 residence offers approx. 2,600 sq ft across three levels with two generously sized, recently updated apartments. The home features seven sun-filled bedrooms plus flexible bonus rooms ideal for home offices, walk-in closets, or mudrooms. Many rooms are freshly painted, with a mix of hardwood, tile, and

Suzanne Hickey Best Deal Realty, LLC

OPEN HOUSE Sunday 6/28 between 12pm-2pm-Tastefully renovated open floor concept with 3br/2 baths Condo on 2nd fl in Winter Hill area of Somerville - Features include new kitchen with new cabinets, quartz countertop, new stainless steel appliances including gas stove & microwave, master suite with attached full bath, good sized bedrooms, hardwood flooring throughout, Tile flooring in baths, ample

Maha Krishnakumar LPT Realty, LLC

Welcome to 232 Pearl street Somerville MA. Don’t miss the opportunity to own a fantastic Two-Family Home located close to Magoun Square and just steps from the new Green Line, dinning, bars and bike path. First floor (Unit 1) has 3 rooms, 1 bedroom, 1 bathroom, living room and Kitchen. Second floor (Unit 2) has 6 rooms 3 bedrooms, 1 bathroom, kitchen, dining and living room. Off-street parking

Arlindo Neto Cameron Real Estate Group

This distinctive building offers strong curb appeal and undeniable character. Located on a tree-lined street, the property features six 1-bedroom, 1-bath units, making it an ideal addition to any investor’s portfolio. Front and back porches enhance tenant appeal. The building is equipped with central heat and hot water, providing efficiency and convenience. Paved driveway. Situated in a prime

Maggie Dee + Charles Cherney Team Compass

Discover an incredible opportunity for OWNER OCCUPIED HOME WITH INCOME on a prime corner lot at the end of a quiet dead-end street in one of Somerville’s most sought-after neighborhoods! This beautifully maintained triple-decker offers three spacious units, two will be delivered VACANT, each with 3 bedrooms and 1 bath—perfect for investors or savvy owner-occupants. Units 1 and 2 will be delivered

Melissa Meyer Lawton Real Estate, Inc

Top-floor gut-renovated 2-bed, 2-bath condominium at 174 Walnut Street offering approx. 1,345 SF of bright, stylish living. This third-floor home features an open living/dining layout, hardwood floors, high ceilings with skylights, oversized windows, recessed lighting, central air, and clean modern finishes throughout. The kitchen includes white shaker cabinetry, quartz counters, stainless steel

Kirsten McEleney KM Real Estate Group

Beautiful gut-renovated 3-bed, 2-bath condominium at 174 Walnut Street offering approx. 1,532 SF of bright, single-level living. This second-floor home features an open living/dining layout, hardwood floors, oversized windows, recessed lighting, central air, and clean modern finishes throughout. The designer kitchen includes white shaker cabinetry, quartz counters, waterfall island with seating,

Kirsten McEleney KM Real Estate Group

Sunny top-floor 3-bedroom condo on a quiet cul-de-sac in Winter Hill. Hardwood floors, recessed lighting, and oversized windows create a warm and inviting living space filled with natural light. The front bedroom features bay windows and a ceiling fan. The living room includes a decorative mantel, ceiling fan, and mini-split. Thoughtfully designed floor plan with all three bedrooms separated from

Maggie Dee + Charles Cherney Team Compass