HouseSigma’s Calgary PriceWatch has tracked a clear pattern through 2026 so far: homes are selling for less than they did a year ago, taking longer to move, and closing at bigger discounts off list.
For most sellers, that softening market means accepting a bid below expectations and waiting a few weeks longer than planned. But for a smaller group, often at the higher end of the market, it has meant something more punishing: many months or even years of no sale, terminated listings, relistings, and dramatic price reductions before a buyer finally came through.
Below are HouseSigma’s picks of Greater Calgary’s 10 most painful home sales of 2026 so far, based on MLS data on sales between January 1 and April 23. The list is a combination of three rankings: biggest dollar discount off final list price, longest total time on market across all listing attempts, and highest number of repeated listings before the sale closed. The first property is ranked at the top as it appears on two of these lists, making it (in our opinion) the most painful sale of the year to date.
1. 340 West Chestermere Drive: $1,800,000
This is the only property to appear in two of our categories: it is the most-relisted home to sell in 2026 so far, and it is third in the longest total listing period rankings. This beautifully renovated, four-bedroom Chestermere detached home moved in and out of the market across eight listing attempts between January 2024 and March 2026, accumulating 639 days on the market before a buyer finally agreed to $1.8 million. The seller bought the home for $1.06 million in April 2022, so at $1.8 million the sale represents a paper gain — but it’s well below the seller’s original target of $2.2 million.
Details: $1,800,000 | 4+1 bed, 4 bath | 2,971 sq ft | Built 1979 | Sold March 4, 2026
2. 1118 Premier Way SW, Calgary: $4,800,000
The biggest dollar discount of 2026 so far: $550,000 off the final asking price on this grand, 2014-built Calgary detached home. The seller’s first listing went up in May 2025 at $5.89 million and was terminated in December after 200 days without a buyer. The home was relisted in February this year at $5.35 million and sold 63 days later for $4.8 million, 10.3% below that final ask and more than a million bucks off the original target.
Details: $4,800,000 | 4+1 bed, 6 bath | 5,059 sq ft | Built 2014 | Sold April 17, 2026
3. 175 Pumpvalley Court SW, Calgary: $1,600,000
This detached Calgary home, built in 1991, closed 18% below its $1.95 million asking price after three consecutive listings beginning in April 2025. The first two were terminated without a sale — 36 days on the first attempt (priced at $2,595,000), 132 days on the second ($2,190,000). The third listing ($1,950,000) finally closed in late February 2026 at $350,000 below ask, the second biggest dollar loss of 2026 so far.
Details: $1,600,000 | 3+2 bed, 5 bath | 3,815 sq ft | Built 1991 | Sold February 27, 2026
4. 1212 Montreal Avenue SW, Calgary: $3,150,000
This attractively renovated Calgary detached house, built in 1983, tried and failed to sell twice in 2023 (listed at $3.72M) and 2024 ($3.42M) before finally moving in March 2026. The two earlier listings combined for 406 days on market through those abandoned attempts. The seller returned in September 2025 with a $3,499,000 list price and closed five months later for $349,000 below ask.
Details: $3,150,000 | 5+1 bed, 7 bath | 4,726 sq ft | Built 1983 | Sold March 5, 2026
5. 178125 240 Street W, Rural Foothills County: $2,925,000
Four listings and a whopping 905 active days on the market, this is the longest total time of any sale in Greater Calgary in 2026 so far. The Rural Foothills County property with a ranch and a three-bedroom house was first listed in June 2023 for $2,999,000 and bounced through two listing expirations. The third listing, beginning April 2025 at a barely reduced price of $2,990,000, finally closed in January 2026 at $2.925 million. A rare tale where the seller held out for the right buyer who eventually showed up to pay close to full ask, so the pain paid off.
Details: $2,925,000 | 3+1 bed, 3 bath | 1,680 sq ft | Built 1979 | Sold January 26, 2026
6. 703 Green Haven Place, Rural Foothills County: $1,525,000
Another Rural Foothills County acreage, this one a 2024-build. The home was listed in April 2024, starting at $1,719,900, and spent the next 21 months cycling through three expired listings before finding a buyer in mid-January 2026, after 649 active days on market. The final listing went up on January 5, 2026 and sold within 16 days.
Details: $1,525,000 | 3+1 bed, 4 bath | 2,900 sq ft | Built 2024 | Sold January 21, 2026
7. 426-255 Les Jardins Park SE, Calgary: $479,900
A two-bedroom, 977-square-foot Calgary condo built in 2022, this is the only condo on our list. The unit sat on the market for 633 active days across three listings: an April 2024 listing at $529,900 that expired on December 31, a January 2025 listing that expired on June 30, and a third listing from July 2025 that finally sold on January 23, 2026. For a building completed just a few years ago, that represents a substantial share of the unit’s post-construction life spent listed.
Details: $479,900 | 2 bed, 2 bath | 977 sq ft | Built 2022 | Sold January 23, 2026
8. 196 Wolf Hollow Park SE, Calgary: $515,000
A 2020-built rowhome in SE Calgary that went through seven listings across eight months before selling, second only to our #1 entry. The seller started fresh in late June 2025 after an earlier attempt that terminated after just six days, then cycled through six more listings averaging just over four weeks each. The property closed in February 2026 at $515,000.
Details: $515,000 | 3+1 bed, 4 bath | 1,313 sq ft | Built 2020 | Sold February 13, 2026
9. 96 Belmont Terrace SW, Calgary: $673,000
A 2017-built Calgary detached house that went through seven listings in just six months between August 2025 and February 2026. Four of those listings ended and were immediately replaced with a new MLS number on the same or next day, a pattern that effectively resets the “days on market” counter shown in public listing pages and is a common tactic for properties struggling to attract offers. The home finally sold for $673,000 on February 6, 2026.
Details: $673,000 | 3 bed, 3 bath | 1,937 sq ft | Built 2017 | Sold February 6, 2026
10. 103 Masters Heights SE, Calgary: $565,000
Seven listings in the six months between August 2025 and February 2026, averaging just 22 days each, gives this small bungalow the shortest average listing duration of any property in our top 10. In five of the seven listings, each listing ended and restarted on the same or next day with a new MLS number — the same pattern seen on 96 Belmont Terrace, above. The home sold in mid-February 2026 for $565,000, closing out more than six months of near-constant listing activity.
Details: $565,000 | 1+2 bed, 3 bath | 1,002 sq ft | Built 2016 | Sold February 18, 2026
HouseSigma’s Greater Calgary market infographics track the higher-level statistics, while these 10 properties are what those numbers look like up close, for the sellers who felt them most.
Find Calgary-region homes for sale on our Map Search page, where you can filter for price, property type, and much more. Plus, keep your eye on our Alberta blog page to stay up to date with market trends, sales data, and remarkable listing stories.