37 Cypress Bay

Windsor Park, Winnipeg

65.1

Good

Overall 65.1

Compared with neighbourhood average

1,038 sqft (bottom 38%)

Built in 1958 (3 yrs older than avg)

Located in a high-income area

with median household income of ~97k

Transit 92.0

3-min walk to transit with 5 nearby routes

Within 500m: 3 schools, 1 shop, 4 parks, and 1 sports facility nearby

Living Area

Below average

5% smaller than neighborhood avg.

Year Built

Below average

3 yrs older than neighborhood avg.

Mother tongue

English · 72%French · 12%

Past 10 years Windsor Park sales snapshot (~80% of all data)

Sold Count

1,217

Median price

395k

$/sqft

$375/sqft

Avg build year

1961

Need help understanding this property?

Buying a home is more than a transaction. Our Winnipeg real estate agents provide market insights, pricing analysis, and neighbourhood expertise to help you decide with confidence.

Usually replies in a few minutes

Property score

65.1 is composed by the two sections below.

Property Score

54.0Fair
Living Area1,038 sqft52Fair
Year Built195843Low
Lot Size6,003 sqft81Excellent
Neighbourhood Sales Activity42Low

Community Score

81.7Excellent
Household Income83Excellent
Education Level63Fair
Housing Stress93Excellent
Core Housing Need100Excellent
Employment Health83Excellent

Neighbourhood Sales

Windsor Park

How to read: Share of sales in each ~$50k price band for “windsor park” (Detached houses (non-condo), 2024). The tallest band is the mainstream budget range; multi-year view shows how that band shifts over time.

Market Conditions · WinnipegSeller's Market
Buyer'sBalancedSeller's

Sales-to-New-Listings

64.6%

1,196

sold

1,852

new listings

Manitoba Real Estate Association March public data on New Listings and Properties Sold across Manitoba

Sold Above Asking

65%

Majority sold above asking

68 of 104 sold above asking · Manually compiled from MLS Winnipeg sold listings, May 4 – May 10, 2026

With a Sales-to-New-Listings ratio of 64.6% and 65% of homes selling above asking price, demand is clearly outpacing supply. Buyers are competing, which is putting upward pressure on prices.

Area census snapshot

Dissemination area (DA) — Statistics Canada 2021 Census · Area: #46110591

Community deep dive

$97K

Median household income

$105K

Average household income

4%

Low income (LIM-AT)

0.2

Income inequality (Gini)

2.6

P90 / P10 ratio

25%

Single-person households

29%

Families with children

Population, labour & age

Population (2021)869
Labour force participation rate71%
Median age38.8
Avg household size2.5
Unemployment rate6%
Population density2715 / km²

Households & income

Low income (LIM-AT, % pop.)4%
Single-person households25%
Couple families with children29%
Median household income (2020)$97K

Housing

Renter households2%
Condominium dwellings2%
Median dwelling value (owners)$324K

Diversity, education & language

Immigrants (share of pop.)15%
Visible minority19%
Bachelor's or higher (25–64)32%
Mother tongue (1st)English · 72%
Mother tongue (2nd)French · 12%

Figures are for the census dissemination area containing this listing location; sources and margins may apply per Statistics Canada.

Rankings

Living Area

around average
1,038 sqft
0255075100
Same streetBottom 16%Same areaBottom 38%CitywideBottom 30%
Same street · Cypress Bay
#53 / 63
Bottom 16% · Avg 1,587 sqft
Same area · Windsor Park
#2,037 / 3,307
Bottom 38% · Avg 1,091 sqft
Citywide · Winnipeg
#136,159 / 194,458
Bottom 30% · Avg 1,342 sqft

Tax-Assessed Value

above average
383k
0255075100
Same streetBottom 49%Same areaTop 18%CitywideTop 43%
Same street · Cypress Bay
#32 / 63
Bottom 49% · Avg 583.5k
Same area · Windsor Park
#607 / 3,307
Top 18% · Avg 354.2k
Citywide · Winnipeg
#83,630 / 194,458
Top 43% · Avg 390.1k

Year Built

around average
1958
0255075100
Same streetTop 48%Same areaBottom 36%CitywideBottom 39%

Lot Size

around average
6,003 sqft
0255075100
Same streetBottom 37%Same areaTop 39%CitywideTop 31%

To see this property on a map next to nearby houses—and compare year built, living area, assessed value, and lot size in detail—open the neighbourhood analysis page.

Transit & Walkability

Nearby stops, routes & transit score

Nearby Amenities

Dining, education, healthcare, shopping & more

37 Cypress Bay — 13 amenities found within 500 m, across 6 categories, including 3 education (nearest 141 m), 1 shopping (nearest 120 m), 4 parks (nearest 284 m).

Search radius
🏫Education3
🛒Shopping1
🌳Parks4
💪Sports1
Worship3
🏛️Government1

Crime & Safety

Windsor Park · WPS public data · 2026

Annual incidents

17

2026

vs. city avg

-42%

relative to avg

Year-over-year

-94%

vs. prior year

Primary type

Property

47%

Sales History

Sold 1/2019CA$300k–350k
Sold price

Same street

Bottom 17%

Same area

Bottom 46%

City-wide

Bottom 42%

Related homes

Highlights & common questions: 37 Cypress Bay, Winnipeg

Key Characteristics & Ideal Buyer Profile

This is a 1958-built home with a living area of 1,038 square feet on a 6,003-square-foot lot. Its main appeal lies in the balance it offers within the Windsor Park neighborhood. While the property is smaller than the average home on its street, it sits on a lot that is typical for the community. The assessed value is notably higher than the average for Windsor Park, suggesting the home or its location carries a premium compared to nearby properties. A key feature is the practical land-to-living-space ratio: the lot is generous relative to the house, offering potential for outdoor expansion, landscaping, or future additions. This property is best suited for buyers who prioritize a solid location in an established area over raw square footage. It would work well for first-time homeowners looking for a manageable footprint, downsizers who want a single-floor layout without a huge yard, or anyone who values the land more than the interior size and is willing to invest in updates.

Five Possible FAQs

1. How does this home's size compare to others nearby?
On its street, it’s smaller than most — roughly in the bottom 16% for living area. However, in the wider Windsor Park community, it’s close to the average size. If you’re looking at other homes for sale in the immediate area, expect most to be slightly larger inside.

2. Is the assessed value a good indicator of market price?
The assessed value is above average for Windsor Park, which reflects local demand. That said, it’s below the street average and close to the city-wide norm. Keep in mind that assessments are for tax purposes and can lag behind actual market conditions, especially if the home needs updates.

3. What does the land size allow for?
At 6,003 square feet, the lot is typical for the neighborhood and slightly below the street average. It’s roomy enough for a decent backyard, gardening, or a garage, but not oversized. If you’re hoping to add a suite or expand the house, check local zoning — the lot is functional but not generous.

4. Is the 1958 construction a concern?
Homes from this era are common in Windsor Park and across the city. This one is about average age for its community. You’ll likely want to look at the condition of major systems (roof, furnace, windows, foundation) since 1958 homes can vary widely — some are well-maintained, others need significant updating.

5. How does this property stack up against other Windsor Park listings?
It’s competitively priced for the area, with a land size that’s in line with neighborhood norms. The interior is on the smaller side, so it may appeal more to buyers who value lot or location over indoor square footage. Compared to similar-priced homes, it’s likely a fair deal for a solid, unflashy starter or downsizer.

Radar charts, rankings, and side-by-side layouts work best on a larger screen. Open this page on a desktop browser for the full experience.