Chester Real Estate

Summer revolves around the water. Chester Race Week takes over the bay every August, with more than 120 boats a day racing on five courses, and the Chester Yacht Club has been the centre of it since 1902. The Rope Loft on the Front Harbour serves seafood on a deck over the moored boats.

The Chester Playhouse, a 183-seat theatre restored and reopened in 2023, runs theatre, music, comedy and movies through the year. Chester Golf Club is a par-70 seaside course looking out over the islands. The free provincial ferry runs to the Tancook Islands every day, and Oak Island is about 20 minutes away at Martin’s Point, with guided tours on weekends from May to October.

Yes, and that is a big part of its charm. A real share of homes here are summer and second homes, so the village is at its busiest from June to September, with Race Week in August as the high point, and much quieter in winter.

Plenty of people do live here all year, and Halifax is about an hour away. If you are buying to live here year round, ask me what a particular road is like in February.

Yes, and Chester is more straightforward about it than most. A municipal licence is required and there is no fee for it, one per property. You need a valid occupancy permit, no open work orders relevant to the rental, $2,000,000 in liability insurance, a site sketch and all PIDs. Allow about 30 days.

The rule that used to catch people is gone. Since 4 July 2025 the municipal by-law says short-term rentals are not governed by it and no development permit is required. If you were told otherwise, that advice is out of date.

Two things that do still apply: the provincial registration under the Short-term Rentals Registration Act is mandatory on top of the municipal licence, renews by 1 April each year, and does not transfer when the property sells. And a 3 percent marketing levy on guests is coming in by by-law. The published version gives a 1 January 2027 start date, so confirm the current position with the Municipality before you build it into a budget.

No, and this is worth knowing before you pay a premium for the address. Chester Yacht Club membership is separate from property ownership. On the guest side, a member may sign in one guest while present at the club, and a guest may be signed in a maximum of three times per season regardless of which member signs them in. The cap is on the guest, not the member, so knowing several members does not multiply it.

Chester Race Week runs every August and is billed as Canada's largest keelboat regatta. The grounds are open to the public during the day; the evenings are wristband only.

The ferry runs daily, year round, from Chester on the William G. Ernst, and it is foot passenger only. Four round trips Monday to Thursday, six on Friday, and only two on Saturday and two on Sunday. There is no fare; the province removed ferry fees in 2021.

A replacement is planned that would carry 18 cars and land at Blandford instead of Chester, cutting the crossing to about 30 minutes. It is still under construction as of the Province's December 2025 five-year plan and no in-service date has been published. If you buy out there, assume your mainland landing point may change and do not plan around a date nobody has committed to.

Internet is the other one. Mainland Chester is complete on fibre. The Tancook islands are getting Bell fibre too, by submarine cable from Blandford, which the Province said in August 2026 should be finished early this fall. Until it is live, ask about the specific civic address, and about the provincial satellite rebate.

Inside the village, yes. The Village of Chester has its own Land Use By-law, in force since 9 May 2025, with design controls in the Core and Outer Village overlays on things like siding, roof shapes, window area and attached garages. They are a big part of why the village looks the way it does.

Heritage registration here is voluntary, so an older house is not automatically restricted. If you are planning exterior changes, find out which side of the overlay boundary the property sits on before you write an offer.

Yes. The federal ban applies only inside Census Metropolitan Areas and Census Agglomerations, and the Municipality of the District of Chester is in neither, so it does not reach here. The Act is currently set to expire 1 January 2027.

Hubbards is the one place to be careful. The HRM boundary runs through that area, and a property on the Halifax side sits inside the Halifax CMA where the ban does apply. A Hubbards mailing address settles nothing. Check which municipality the PID is assessed in.

Nova Scotia's 10 percent non-resident deed transfer tax is separate and it does apply, with an exemption if you move here and file proof of residency within a year of closing. For closings before 6 August 2026 that window was six months. Detail is in Buying From Away.

I can. I’m Doug Mills, a REALTOR® with Royal LePage Atlantic. I live on St. Margarets Bay, work out of the Royal LePage Atlantic office on Main Street in Mahone Bay, and buy and sell along the South Shore from Peggy’s Cove to Liverpool. A lot of Chester’s best waterfront sells before it’s ever advertised, so tell me early what you’re after.

Call or text me at +1 902-410-3740, or email doug@dougmills.ca.

Chester carries the highest concentration of high-end property on the shore, and frontage, exposure, water depth and mooring move the price far more than square footage.

As a rough guide, under $600K is off the water: a village house, or something out toward Chester Basin and New Ross. $600K to $1M buys a good house in the village, or water views without full frontage. $1M to $2M buys real frontage on the Front or Back Harbour, and estates, deep frontage and islands start around $2M. The price bands and current listings are further up this page.

Outside the village, almost everything has its own well and septic system, waterfront included. Inside the village it varies by street, so check the specific property.

Make your offer conditional on a water test, for quality and for how much the well delivers, and on a septic inspection. Ask how old the septic system is too, because replacing one is a real cost and it belongs in the conversation before you firm up.

About an hour to downtown Halifax, roughly 66 km on Highway 103, and plenty of people commute.

Bayers Lake, with Costco and the big-box stores, is about 50 minutes. Halifax Stanfield airport is an hour and a quarter or more, and Mahone Bay is 25 minutes along the shore.