Gilman Square: a Perfect Place to Buy or Sell a Home
Gilman Square is in the Winter Hill section of Somerville. Thanks to the recent arrival of the Gilman Square green line T stop, we are seeing a lot of gentrification in this part of Somerville. It's definitely more affordable than some more "mature" markets in Somerville like Davis and Porter Squares. I feel like there is a real community feeling in this part of Somerville with lots of residents who have been here for a long time, which I really love. It's also right by Somerville High School and has excellent access to Rt-93 and is quite close to the Union Square area of Somerville, too.
What is your specific real estate need in Gilman Square?
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Selling a Single Family in Gilman Square · Selling a Condo in Gilman Square · Selling a Multi-Family in Gilman Square · Selling a Development Opportunity in Gilman Square
Buying a Single Family in Gilman Square · Buying a Condo in Gilman Square · Buying a Multi-Family in Gilman Square · Buying a Development Opportunity in Gilman Square
Selling a single family in Gilman Square
Demand for single families in the Gilman Square section of Somerville has gone up tremendously. I still remember back in 2018 what the market looked like in Gilman Square. Back then there was new green line T and it wasn’t totally clear when it would be coming.
Most buyers weren’t interested in owning a single family in Somerville that required bus, car or bike transportation to work. Homes sat and great deals could be had. That has all changed over the past 7 years. Now with the green line T stop in play, plus the Somerville community path extension, we are seeing droves of first time home buyer push into Gilman Square.
With the new demand comes increased prices and more importantly a new host of buyer expectations. It’s my goal to help walk you through what those expectations look like for your single family, to ensure you get the best possible price and terms. If you are curious to understand what needs to be done to your specific property, give me a ring at 617-833-7457!
Selling a condo in Gilman Square
While demand for Gilman Square condos has risen exponentially compared to where this market was even 7 years ago, it’s important to recognize that Somerville condo buyers often will start by targeting the more hot areas of Somerville first - places like Davis Square, Porter Square, and Union Square.
So since Gilman Square is more of a secondary market in the eyes of many Somerville condo buyers, it’s important to make sure you provide serious value with your Gilman Square condo when compared to similar units in other parts of Somerville. You need to be able to provide more quality, more space and at a lower price in order to get strong offers and good terms here. It is totally doable but it requires a lot of preparation and strategic pricing. I can help you navigate the entire process from A to Z, just give me a buzz at 617-833-7457.
Recent condo I helped a client sell in Gilman Square:
55 Montrose St, Unit 2: I worked with my developer client to purchase a 2-family in Somerville, close to the Gilman Square green line T stop and then convert into two luxury condos. We sold the upstairs unit to a young professional couple. This is a very prime location on a quiet street, one block to the T and community path, with all the bells and whistles - a private deck, luxury kitchen, 3 beds and 2 full bathrooms, plus off-street parking.
Selling a multi-family in Gilman Square
The Gilman Square multi-family market is what I consider “up and coming”. As a result, it is pivotal that proper preparation is done to your units in order to maximize resale values. You have to remember, multi-family buyers in Somerville are looking throughout Somerville and often times Cambridge too.
In other parts of Somerville, buyers will see higher rental prices and lower cap rates, so if your goal is to get the highest price possible, you want to demonstrate that you have great units with nice flows that check a lot of renter boxes. The more you can check those renter boxes, the more we can argue for higher rent prices. And the higher rent prices your units can attract, the more willing buyers will be to pay a premium price for an up and coming area within Somerville.
We also have to consider a potential owner-occupant play. With the new green line T stop in play, I have run into quite a few owner-occupant buyers that are either young professional couples or young professional families who are looking to move into an up and coming section of Somerville. For properties with the right layout, right features, and right square footage, position your property as an owners unit + rental unit can attract the highest prices in some scenarios.
Regardless of your multi-family set-up in Gilman Square, I am here to help. Just give me a call and we can sort it out - 617-833-7457!
Recent multi-family I helped a client sell in Gilman Square:
11 Madison St: My seller client owned her 2-family in Gilman Square Somerville for many decades but was managing from out-of-state. She needed someone who was a true expert on the local Somerville multi-family market to come in and help guide her. Both units were in horrible shape and required substantial work. I actued as a mini-GC and completely transformed the property, then we staged it and sold it for a very high price per a square foot. She was extremely happy with the outcome!
Selling a development opportunity in Gilman Square
Developments in Gilman Square have increased with the newer green line T and Somerville Community Path extension now in place. Specifically for properties in complete disrepair OR those properties that sit on large lots (think 5k+ sized lots) OR large multi-families with at least 3,500 square feet of living area.
All of these scenarios provide opportunities to either condoize existing structures OR create an addition to increase square footage OR demolish properties and build many units on a lot. These type of scenarios are all attractive to developers and because price per a square footage numbers tend to be a little bit lower in Gilman Square, Somerville developers are often more intrigued in a place like Gilman Square to explore an offer more seriously.
If you think you have a Gilman Square development opportunity on your hands, give me a ring and I can give you my thoughts!
Buying a single family in Gilman Square
If you’re thinking of buying a single family in Gilman Square, I think you’re targeting an awesome area in Somerville that has a true community like feel. I love the Gilman Square area for purchasing a single family home because you can often find nicely sized lots, and great price per a square foot - sometimes as low as around $500/sq ft.
So if you want to get a great bang on your bucket, be minutes to the Gilman Square green line T stop as well as Rt-93, I think this is a great place to buy in.
In terms of pricing, small 3-bed single families with less than 1,500 square feet typically go for around $1M. Larger single families with 2,000+ square feet can occasionally be found starting around $1.2M and can go up to $1.7M+ for gut renovated luxury versions.
If you need to be in Somerville but don’t have a Davis Square or Union Square budget, this is a prime area to target. Just reach out and we can talk through your specific needs at 617-833-7457!
Buying a condo in Gilman Square
There are quite a few price buckets when I think about condos in Gilman Square. As of this writing (end of 2025), the lowest price point are for investor grade 1-bed/1-bath units. Typically these start at around $400k and will have low-end appliances in older brick buildings. On the high end, you can expect to pay around $650k for a really nice 1-bed.
2-beds typically start around $600k in Gilman Square - these will typically be investor grade units in brick buildings with some work required. Often they are dated and don’t have central a/c or laundry in-unit. On the high end, I have seen 2-bed/2-bath units in Gilman Square go for as high as $900k, these can be stunning Victorian multi-family condo conversions with lots of period details like original fireplaces, stained glass, original woodwork, etc. They often have extra high ceilings 9’ or even 10’ and lots of square footage - I often see 900 to 1,100+ square feet. These can be excellent and unique buys and a great value for Somerville in my opinion.
3-beds typically start around mid $700s for investor grade units with perhaps 1,200ish square feet and completely gut renovated 3-bed units can go all the way up to $1.3M for more like 1,800+ square feet with new everything.
4-bed+ condos typically start around $1.1M and can go up to $1.4M - the range will depend on where precisely they are located in Gilman Square, how large the units are, how many bedrooms the units have, and the finishes throughout.
If you are considering a Gilman Square purchase, give me a call to talk through your options at 617-833-7457!
Buying a multi-family in Gilman Square
Gilman Square multi-families tend to land in pretty clear cut buckets for the most part. First you have your 2-families that generally land in the $1M to $1.35M range. The low end range tends to be closer to 2,000 square feet and in need of some updating throughout. The high-end range tends to be closer to 3,000 square feet and tends to be totally or very close to totally updated and turn-key.
3-families in Gilman Square tend to start at around $1.4M most typically around 3,000 sq ft with some work required and go up to $1.7M for very large multis over 4,000 square feet.
Gilman Square has seen some excellent appreciation over the last few years and if you are thinking of investing this can be a nice area to target. Give me a call and I am happy to chat through your options - my cell is 617-833-7457.
Recent multi-families I’ve helped clients buy in Gilman Square:
55 Montrose St: My developer client was looking to do a condo flip in Somerville. We were able to secure this 2-family a block from Gilman Square at an excellent price at a time when interest rates were low and competition was extremely high for 2-families. This property was ultimately converted into two luxury condos and the owner sold one and is currently renting out the other unit.
31 Marshall St: My buy and hold investor client was looking for a cashflowing asset with long term potential. This attached 3-family was a few blocks to the new Gilman Square green line T stop and it was listed in the dead of winter. The result? Low buyer interest overall and a chance for my client to secure an outstanding deal well below market rate. We quickly identified that all three units were combined well over $1,500/mo under market rate. We quickly rose rents to market and this unit is now a cash cow!
10 Stickney Ave: My client was looking for a property with cash cow potential that needed some work. We found it in this massive 3-family a block to Gilman Square. It needed some work but we were able to get it at $140k under asking. Once all work is completed and units are rented up, I predict this would to bring in between $11k and $12.5k/mo to start, with lots of rental growth over the long haul.
Buying a development opportunity in Gilman Square
There are definitely strong buying opportunities in and around Gilman Square, driven in large part by the typically lower prices compared to other sections of Somerville. In particular, around Gilman Square I look for both single families and multi-families that are either on lots of over 5,000 square feet OR properties in total disrepair.
Gilman Square already offers among some of the lowest price per a square foot for livable square footage, compared to other parts of Somerville and when you add in properties in total disrepair, you’re often looking at buying opportunities with low price points and good margins.
If you are looking for a development opportunity in Gilman Square, let me know what you are looking for and I will keep you on my radar. My cell is 617-833-7457.
Read more about the selling and buying services that I can provide here:
Above are samples of properties I’ve helped clients sell or buy. Read more about my past work here.
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