Winter Hill

Probably most famous for its association with Whitey Bulger and the notorious Winter Hill Gang, this neighborhood in eastern Somerville is experiencing a slow but steady revitalization. The neighborhood has a strong Catholic flavor from its early mix of Irish and Italian immigrants, and is home to a variety of eateries including old-school Italian establishments like Mamma Lisa’s and Leone’s, plus more adventurous fare like the Ethiopian restaurant Fasika, and a Mediterranean gem called Sarma.

Browse Winter Hill real estate below. Contact us to ask questions or schedule a tour. 

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137 Sycamore, Somerville, MA

MLS Number 72289406

  • Single Family
  • Parking Spaces 6
  • Year Built 2002
  • Full Bath 3
  • Bathroom 4

Welcome to 137 sycamore street. This sophisticated yet elegant custom colonial was seamlessly built with a blend of fine craftsmanship and modern function. Upon entering the property you are struck by the gorgeous formal living room and 14ft ceilings with deeply detailed crown molding. The foyer leads down thru the wet bar to the formal dining room and into a true chef's kitchen! This bright and sunny space boasts an oversized island, viking 6 burner range with double ovens, thermador cooktop, subzero fridge, and an additional double wall oven! Unwind in the unique round family room with wood burning fireplace and built ins with access out to your massive mahogany deck offering views of boston. The second level offers a stunning master suite with cathedral ceiling, sitting area, double walk in closets and a bathroom with a spa-like bathtub, separate shower and double sinks all done in marble. This masterpiece has so much more to offer. Truly a tremendous value, come take a look!

Listed by Jacqueline Veri and Dustin Leclair, Century 21 Commonwealth

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RE/MAX Destiny: Cambridge
907 Massachusetts Avenue
Cambridge MA, 02139
Office: 617-576-3800

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$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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18 Dartmouth, Somerville, MA 02145

MLS Number 72284153

  • Multi-Family 3 Family
  • Bedrooms 9
  • Year Built 1910

Amazing Location!! Potential Cash Cow!! Oversized 3 Family with GARAGE PARKING with potential to expand. Perfect owner occupant, long term hold or exchange opportunity. Grab a HUGE piece of Somerville before the Green Line Extension comes to town! All Tenants are TAW and rents are well below market. Units have flexible layouts, high ceilings and hardwood floors. Basement provides a great opportunity for additional expansion of living space. Located on a gorgeous tree-lined one way street close to Winter Hill Brewing Company, Sarma and many more great restaurants and shops, as well as short distance to buses that bring you to Davis, Sullivan and Lechmere T stops!

Listed by Ted Billings and Fayth Kestenbaum, RE/MAX Leading Edge

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RE/MAX Destiny: Cambridge
907 Massachusetts Avenue
Cambridge MA, 02139
Office: 617-576-3800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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43 Derby Street, Somerville, MA 02145

MLS Number 72339245

  • Multi-Family 3 Family
  • Bedrooms 10
  • Year Built 1910

WOW! GUT REHABBED, SPRINKLERED 3 FAMILY! PERFECT FOR INVESTORS OR OWNER OCCUPANTS! Incredible and rare 3 family in prime location featuring beautiful gleaming hardwood floors throughout, high end fixtures and trim, modern tiled baths and recessed lighting throughout. Many windows and abundant natural sunlight, central A/C and potential for parking. All New Plumbing and electrical, HVAC. Full basement, all utilities separate, tenants pay. Tandem parking for $200/month. Gross annual rent is $117,360 with room for upside potential. Short distance to Assembly Row, Cambridge, downtown Boston and major transportation routes. Projected rents for 9/1/2018 higher. See attached proforma. Condo docs attached it is currently 3 Condominiums but can be turned back in to a 3 family at closing upon request..

Listed by Nicholas Spagnola, Adam Garcia and Louis Rubino, Spagnola Real Estate & Consulting, Inc.

{$office->Name}

RE/MAX Destiny: Cambridge
907 Massachusetts Avenue
Cambridge MA, 02139
Office: 617-576-3800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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172 Pearl Street, Somerville, MA
Open House

MLS Number 72349924

  • Single Family
  • Next Open House: Sun 24th 12:00 pm - 2:00 pm
  • Parking Spaces 4
  • Year Built 1890
  • Full Bath 3

Welcome home -- this absolutely charming and updated Single family Colonial is awaiting its new owners! This loved and cared for home features six bedrooms, three full bathrooms over four floors of living area. Enjoy pulling into your private driveway, walking past your white stone backyard and right into your kitchen. This is such an easy home to access, the layout is great with a nice flow to it. You'll find gorgeous turn of the century hardwood floors throughout, high ceilings and large eat-in kitchen. The basement has been refinished with livingroom, kitchen and bedroom -- makes for a nice in-law suite or teenager getaway. The second floor has three good sized bedrooms, full bath and great office or infant room. The attic, is finished with two bedrooms with great sunlight and good sized closets. Let's not forgot about the gorgeous wraparound front porch that is great for hanging a hammock or enjoying late night city views. Short walk to T (Sullivan) - OPEN HOUSE SUNDAY 24TH 12-2PM

Listed by Leland E. Dimeco, Boston Green Realty

{$office->Name}

RE/MAX Destiny: Cambridge
907 Massachusetts Avenue
Cambridge MA, 02139
Office: 617-576-3800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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68 Fremont Street, Somerville, MA 02145
Open House

MLS Number 72319624

  • Condo or Co-op
  • Next Open House: Sun 24th 12:00 pm - 1:30 pm
  • Bathroom 2
  • Year Built 1910
  • Full Bath 2

LAST UNIT AVAILABLE. DON'T MISS OUT ON OUR OPEN HOUSE THIS SATURDAY. Luxurious Two Bed Two Bath Unit Boasting a beautiful kitchen with Quartz countertop, Stainless Steel Appliances, Thor Professional Grade Range if you love to cook. Just 6 minutes to Down Town and 2 minutes from 93 and Assembly Row, and few steps to Public Transportation. Built In Speakers in your Living Room & Master Suite to create that Home Theater Experience, RiNG DOOR BELL as part of your Tech Package. Spacious Master with California style build in closet and large windows. Beautiful hardwood floors with a spacious floor plan. Love outdoor space? Come see the beautifully landscaped private yard that comes with this unit, along with a Large storage room.

Listed by Mike Tokatlyan, Contempo Builders, Inc.

{$office->Name}

RE/MAX Destiny: Cambridge
907 Massachusetts Avenue
Cambridge MA, 02139
Office: 617-576-3800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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49 Temple Street, Somerville, MA 02145
Active With Contract

MLS Number 72345206

  • Condo or Co-op
  • Bathroom 1
  • Year Built 1910
  • Full Bath 1
  • Bedrooms 2

Location, location. Very close to 93,1 mile from Sullivan Square Orange line-under a mile to the upcoming Green Line Gilman Square Stop, close to Union Square, very close to bike path, steps from the bus stop. Close to some of the best restaurants in Greater Boston such as Sarma, LaBrasa and Winter Hill Brewery. Only a few blocks from Foss Park, Somerville's largest park. Proximity to Assembly Square (5 minute walk). Deeded off street parking and a lovely side yard for additional outdoor space. Outstanding Chef's kitchen with Bosch Stove, glass tile backsplash, stainless steel appliances, recessed lighting, solid Butcher Block counter, wine refrigerator, tile floor with sliding glass doors to private outdoor deck. Hardwood floors, brand new windows, laundry in unit, gas heat (2012) 9 foot high ceilings and storage space. 100% owner occupied, professionally managed, pet friendly.

Listed by Penny G. McKenzie, Northrup Associates

{$office->Name}

RE/MAX Destiny: Cambridge
907 Massachusetts Avenue
Cambridge MA, 02139
Office: 617-576-3800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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326 Broadway, Somerville, MA 02145
Open House

MLS Number 72346348

  • Condo or Co-op
  • Next Open House: Sun 24th 11:00 am - 1:00 pm
  • Bathroom 1
  • Year Built 1970
  • Full Bath 1

Fantastic opportunity to own on Winter Hill. Spacious corner two bedroom condo features fully applianced kitchen with new dishwasher and range, generously sized living room and bedrooms with new carpet. New roof in 2016 and a new electric sub-panel to be added prior to closing. Fresh paint throughout. Off street deeded parking space. Fantastic location, just minutes to Rt 93, the New Assembly Row, and convenient to Sullivan Square T/ busses, Gilman Square (potential green line extension). Bus Stop near building with line to Davis, Leachmere, and Sullivan Square. Laundry in building and professionally managed.

Listed by James Major, Century 21 North East

{$office->Name}

RE/MAX Destiny: Cambridge
907 Massachusetts Avenue
Cambridge MA, 02139
Office: 617-576-3800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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40 Evergreen Avenue, Somerville, MA 02145

MLS Number 72331659

  • Rental
  • Date Available 09/01/2018
  • Bedrooms 4
  • Year Built 1900
  • Pets Yes w/ Restrictions

AVAILABLE SEPT.1ST... STUNNING brand NEW high-end gut renovated home in this two-family Victorian townhouse. This sprawling open concept 4 bedroom / 3.5 bath DUPLEX is over 2,200 square feet with a finished basement, and a private wrap-around outdoor deck. Features include open chef's kitchen with breakfast island, granite countertops, stainless steel appliances, master bedroom suite with walk-in closets and en-suite bathroom with double vanity sink, soaking tub and separate glass-enclosed shower stall, game / family room, washer / dryer, original wood staircase, cathedral ceilings, exposed beams, skylights, hardwood floors, central heating / cooling, marble bathrooms, LED lighting, generous customized closet, storage space, 2 off street parking spaces. Conveniently located in close proximity to Downtown Boston, Harvard, MIT, restaurants, shopping, public transportation, I-93 and Assembly Square!

Listed by Vincent C. Lee, Supreme Property Solutions

{$office->Name}

RE/MAX Destiny: Cambridge
907 Massachusetts Avenue
Cambridge MA, 02139
Office: 617-576-3800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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17 Bond, Somerville, MA 02145

MLS Number 72346269

  • Rental
  • Date Available 07/01/2018
  • Bedrooms 4
  • Pets Yes w/ Restrictions

This exceptional duplex apartment on Bond St in Winter Hill neighborhood of Somerville features: - 2 Floors of living space - 2 Bathrooms - Hardwood Floors - Front Deck - 2 Refrigerators (1 on each floor!) - Driveway parking available for rent Great location right off Broadway just a short ride to Tufts.

Listed by Louis Gordon, Revolution Realty, LLC

{$office->Name}

RE/MAX Destiny: Cambridge
907 Massachusetts Avenue
Cambridge MA, 02139
Office: 617-576-3800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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17 Bond, Somerville, MA 02145

MLS Number 72346279

  • Rental
  • Date Available 07/01/2018
  • Bedrooms 5
  • Pets Yes w/ Restrictions

This exceptional duplex apartment on Bond St in Winter Hill neighborhood of Somerville features: - 2 Floors of living space - 2 Bathrooms - Hardwood Floors - Front Deck - 2 Refrigerators (1 on each floor!) - Driveway parking available for rent Great location right off Broadway just a short ride to Tufts.

Listed by Louis Gordon, Revolution Realty, LLC

{$office->Name}

RE/MAX Destiny: Cambridge
907 Massachusetts Avenue
Cambridge MA, 02139
Office: 617-576-3800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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315 Broadway, Somerville, MA 02145

MLS Number 72351743

  • Rental
  • Year Built 2018
  • Bedrooms 2
  • Pets Yes w/ Restrictions

Available Now or anytime July or August 1st. Flexible move-in date. Brand New Stylish 2 Bedrooms, 2 Bathrooms unit in Modern Building located in Center of Winter Hill, Somerville. Contemporary open kitchen with quartz counters, built-in breakfast bar, stainless steel appliances, high ceiling, extra large windows, brilliant hardwood floors, spacious closet design and modern bathroom, Laundry room on every floor level and option for in-unit laundry. Garage parking space is available. Pet friendly with restriction. Easy access to Assembly Row, Tufts University, Cambridge, Downtown Boston, McGrath highway, Route 93, Route 90 Mass Pike, Storrow Drive.

Listed by Daniel S. Lee, Town Property Group

{$office->Name}

RE/MAX Destiny: Cambridge
907 Massachusetts Avenue
Cambridge MA, 02139
Office: 617-576-3800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

8 Howe Street, Somerville, MA 02145

MLS Number 72338036

  • Rental
  • Date Available 09/01/2018
  • Bedrooms 2
  • Pets Yes w/ Restrictions

Spacious 2 Bdr. apartment with hardwood floors, updated kitchen , large livingroom, office, Central Air & washer/ dryer. Private deck, Some Basement storage.Bathroom has no Tub but a stall shower.Convenient Commuter Location to Rte. 93, downtown Boston, Broadway bus routes into Davis, Lechmere,Assembly, Sullivan & Union Squares. Pick up Green, Red & Orange Lines. Nice neighborhood with easy walking access to Pharmacies, Banks and Coffee Shops . A very Nice Apartment to call Home!

Listed by Michael Brandon, William Raveis R.E. & Home Services

{$office->Name}

RE/MAX Destiny: Cambridge
907 Massachusetts Avenue
Cambridge MA, 02139
Office: 617-576-3800

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 4.57% last updated on Jun 21, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

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