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Four-Season Cottages For Sale on Lake Simcoe

174 four-season cottages for sale on Lake Simcoe right now, from $0K to $16M. Updated through the day from the MLS®.

Lake Simcoe marketMedian $1.25M173 for sale+14 new this week~57 days on marketMarket stats
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174 four-season cottages for sale on Lake Simcoe
47 Parkside Drive, Oro-Medonte26 photos$1,700,000Waterfront cottage3 bed · 3 bath · 2000-2500 sq ft47 Parkside DriveRural Oro-Medonte, Oro-MedonteGarage · 6 parking · Lot 108.1 x 208 ftCourtesy of: LPT REALTY183 Lakeshore Road W, Oro-Medonte49 photos$2,850,000Waterfront cottage4 bed · 7 bath · 3500-5000 sq ft183 Lakeshore Road WRural Oro-Medonte, Oro-MedonteGarage · 7 parking · Lot 97.7 x 217 ftCourtesy of: RE/MAX CROSSTOWN REALTY INC.311 - 90 Orchard Point, Orillia33 photos$639,900Resort condo1+1 bed · 2 bath · 1000-1199 sq ft311 - 90 Orchard PointOrilliaMaint. fee $750/mo · Garage · 1 parkingCourtesy of: Royal LePage Quest605 - 80 Orchard Point Road, Orillia44 photos$609,000Resort condo1+1 bed · 2 bath · 900-999 sq ft605 - 80 Orchard Point RoadOrilliaMaint. fee $745/mo · Garage · 1 parkingCourtesy of: RE/MAX RIGHT MOVE171 Lake Drive N, Georgina50 photos$1,550,000Waterfront cottage4 bed · 3 bath · 2500-3000 sq ft171 Lake Drive NHistoric Lakeshore Communities, GeorginaGarage · 7 parking · Lot 69.6 x 196.6 ftCourtesy of: SOTHEBY'S INTERNATIONAL REALTY CANADA1031 Wisker Avenue, Innisfil50 photos$2,888,000Waterfront cottage5 bed · 3 bath · 2500-3000 sq ft1031 Wisker AvenueLefroy, InnisfilGarage · 10 parking · Lot 138.3 x 141.2 ftCourtesy of: FOREST HILL REAL ESTATE INC.2289 Lakeshore Road E, Oro-Medonte48 photos$1,690,000Waterfront cottage3 bed · 3 bath · 2000-2500 sq ft2289 Lakeshore Road ERural Oro-Medonte, Oro-MedonteGarage · 5 parking · Lot 60 x 213 ftCourtesy of: RE/MAX HALLMARK CHAY REALTY104 Hedge Road, Georgina38 photos$1,995,000Waterfront cottage4 bed · 3 bath · 1500-2000 sq ft104 Hedge RoadSutton & Jackson's Point, Georgina4 parking · Lot 138 x 122.8 ftCourtesy of: SOTHEBY'S INTERNATIONAL REALTY CANADA3589 Riva Avenue, Innisfil37 photos$1,499,000Waterfront cottage3 bed · 3 bath · 1500-2000 sq ft3589 Riva AvenueRural Innisfil, InnisfilGarage · 4 parking · Lot 26 x 77 ftCourtesy of: CENTURY 21 ATRIA REALTY INC.11 - 4 Paradise Boulevard, Ramara46 photos$548,000Resort condo3+1 bed · 2 bath · 1400-1599 sq ft11 - 4 Paradise BoulevardBrechin, RamaraMaint. fee $710/mo · 1 parkingCourtesy of: RE/MAX COUNTRY LAKES REALTY INC.8 Shangri-La Lane, Georgina24 photos$2,688,000Waterfront cottage4+1 bed · 6 bath · 3500-5000 sq ft8 Shangri-La LaneKeswick South, GeorginaGarage · 7 parking · Lot 79.7 x 224.3 ftCourtesy of: BEST UNION REALTY INC.309 - 375 Sea Ray Avenue, Innisfil21 photos$479,000Resort condo1+1 bed · 2 bath · 600-699 sq ft309 - 375 Sea Ray AvenueRural Innisfil, InnisfilMaint. fee $572/mo · Garage · 1 parkingCourtesy of: YOUR HOME SOLD GUARANTEED REALTY INTERCITY PLUS INC.

Listing data © PropTx MLS®. Information deemed reliable but not guaranteed.

Market snapshot

Lake Simcoe cottage market today

Based on 173 homes for sale right now (asking prices). Updated through the day.

Get recent sold prices
Median asking price$1.25MRange $239K – $16M
Homes for sale173+14 new this week
Typical days on market57Room to negotiate
Median price / sq ft$670From listed size ranges

Homes by price

Under $700K42
$700K–$1M28
$1M–$1.5M44
$1.5M–$2M32
$2M–$3M17
$3M+10

By style

StyleFor saleMedian price
Waterfront cottage173$1.25M
Cottage134$1.41M
Resort condo39$548K
Log home5$1.73M

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Lake Simcoe

Four-season cottages on Lake Simcoe

Right now there are 174 four-season cottages for sale on Lake Simcoe. Asking prices run from $0K to $16M, and the middle listing is $1.24M. Most are in Ramara, Georgina, Innisfil and Brock.

Lake Simcoe is the big, open lake just north of the city, and owning on it feels different from owning in the Shield lakes farther north. Read the full Lake Simcoe guide.

A four-season cottage has a proper foundation, insulation, a heated water line and a road that is maintained in winter. Those same features make it easier to finance and insure, and they keep the door open to living there full time later.

Common questions

How many four-season cottages are for sale on Lake Simcoe?

There are 174 listings right now, taken straight from the MLS® and updated through the day. New ones are added the day they come on the market.

How much do four-season cottages on Lake Simcoe cost?

Asking prices run from $0K to $16M, with a median of $1.24M. Frontage, shoreline, exposure, road access and the building itself account for most of the spread.

Where on Lake Simcoe are these four-season cottages?

Most of today's listings are in Ramara, Georgina, Innisfil and Brock. Use the map above to see exactly where each one sits on the lake.

Can I get new four-season cottages on Lake Simcoe sent to me?

Yes. Save this search or ask for listing alerts and new four-season cottages on Lake Simcoe are emailed to you the day they hit the MLS®, along with price drops. It is free and you can stop anytime.

Sold history

Lake Simcoe sold prices by year

1087 cottages, homes and lots on Lake Simcoe have sold through the MLS® since 2013, 175 of them in the past 12 months. Sold prices are for members. Joining is free.

See what Lake Simcoe cottages actually sold for

Free members see sold prices, sale-to-asking ratios and every sold listing on the lake.

YearSalesMedian soldAverageLowestHighestSold vs. askingMedian days
2026 to date158
2025160
202489
202336
202285
2021142
2020164
201993
201879
201770
20164
20152
20135

Sold data from the PropTx MLS®, for sales reported on the board. Private and exclusive sales are not included. Figures are a guide, not an appraisal. Information deemed reliable but not guaranteed.

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