For saleExcellent Deal

DetachedOn market 54 daysIncreased +$500,009

5576 Middlebury Dr, Mississauga

Mississauga, ON · L5M 5G8 · MLS® W13791082Updated November 9, 2026

$1,499,999Est. $7,369/mo mortgage

Bedrooms: 4
Bathrooms: 3
Living space: 2500–3000sq ft
Parking spaces: 4

Type Detached
Lot 25.995 acres
Garage Yes
Basement Finished, Full

What you should know

5576 Middlebury Dr is a 4-bedroom, 3-bathroom detached home in Mississauga, listed for $1,499,999. It has 2500-3000 sq ft of living space.

Welcome to 5576 Middlebury Drive, a beautifully updated 4+1 bedroom, 4-bath family home in the heart of highly sought-after Central Erin Mills.
Situated in one of the area's most family-friendly pockets, the home offers outstanding walking access to schools from elementary through high school.
Extensively updated inside and out, with major improvements completed in 2022 and 2024, this spacious home combines modern style with the warmth and functionality of an established family residence.

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1 Upcoming Open House at 5576 Middlebury Dr

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Sunday, November 152:00 PM – 4:00 PMIn person · no booking neededAdd to Google Calendar (opens in a new tab)Apple / Outlook (.ics)

4 Bed, 3 Bath Detached Home in Mississauga

About 5576 Middlebury Drive

Welcome to 5576 Middlebury Drive, a beautifully updated 4+1 bedroom, 4-bath family home in the heart of highly sought-after Central Erin Mills. Situated in one of the area's most family-friendly pockets, the home offers outstanding walking access to schools from elementary through high school. Middlebury Public School (4 min walk), Thomas Street Middle School (1 min walk), and highly regarded John Fraser Secondary School (13 min walk), and Aloysius Gonzaga Catholic Secondary school (17 min walk)..no need to cross a main road. Upstairs, the home offers a highly desirable 4-bedroom layout featuring two rarely found ensuite bedrooms, providing exceptional comfort, privacy and flexibility for growing or multi-generational families. Extensively updated inside and out, with major improvements completed in 2022 and 2024, this spacious home combines modern style with the warmth and functionality of an established family residence. Engineered hardwood flooring flows throughout the main and second levels, creating a seamless and sophisticated look. The bright, modern eat-in kitchen provides a welcoming centre for everyday family life and entertaining. The home has also benefited from a substantial list of recent improvements, including a new furnace (2025), heat-pump A/C system (2023), appliances (2022), extensive window and patio door upgrades (2018), including triple-pane windows, and professionally completed interlock (2024). Buyers can move in with confidence knowing that many of the home's major updates have already been completed. Outside, the property offers a deep lot and the added privacy of having no neighbours directly behind - a desirable feature in this established neighbourhood. Parks, green spaces and recreational amenities are woven throughout the community, while Erin Mills Town Centre, Credit Valley Hospital, Erin Meadows Community Centre, public transit, major commuter routes and highways are all within easy reach. Make this beautiful home your own!

4 bedrooms, 3 bathrooms, about 2,500 sq ft, works out to roughly $600 per square foot. Chat with Zara if you'd like a deeper read on whether this detached fits your budget and timing.

Inside 5576 Middlebury Dr

Every detail from the listing, in one place.

Type: Detached
Style: 2-Storey
Living space: 2500-3000 sq ftas stated on the listing
Parking: 4 spacesYes garage
Basement: Finished, Full

Features & systems

Parking & garage

Garage: Yes
Parking spaces: 4

Interior

Basement: Finished · Full

Lot & land

Lot size (sqft): 4542

Listing & possession

Property style: 2-Storey
Property class: Detached

5576 Middlebury Dr Price & Sale History

Earlier listings of this property, list-price changes, and the most recent annual property tax on the listing.

—IncreasedPrice increasedThis listingMLS® W13791082+$500,009 (50.0%)$1,499,999
Sep 16, 2026For saleListedThis listingMLS® W13791082$999,990

Sourced from MLS®. Includes earlier listings of this property on record.

What's it worth?

How 5576 Middlebury Dr Compares to the Mississauga Market

Zara compares it with recent sales of similar homes nearby. It's a guide, not an appraisal.

Zara’s estimate

Excellent Deal· based on 3,813 recent sales

Value your own home →How accurate are Zara’s estimates?

Summitly estimate, not from TRREB, the MLS® or the listing brokerage. Not an appraisal. How it works

Mississauga market, last 90 days

Median sold price: $872,500
Average sold price: $952,158
Average days on market: 34
Homes sold: 2,167

Closed sales on the TRREB MLS®.

Full Mississauga market report

Recently sold nearby in Mississauga

Sold prices are shown free to signed-in members, as board rules require.

6 nearby sales vs. this home

Closed sales from MLS®, compared with this home's asking price.

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Home	Sold price	$ / sqft	% of asking	Sold
This home5576 Middlebury Drive 4 bd · 3 ba · 2,500 sqft	$1,499,999asking	$600	—	—
1016 Red Pine Crescent 4 bd · 3 ba · 2,500 sqft
7018 Cadiz Crescent 3 bd · 2 ba · 1,100 sqft
1617 Trotwood Avenue 4 bd · 5 ba · 3,500 sqft
3257 Sir Johns Homestead 4 bd · 2 ba · 1,500 sqft
6772 Dolmage Court 3 bd · 2 ba · 1,500 sqft
1149 Mesa Crescent 4 bd · 3 ba · 2,500 sqft

1016 Red Pine Crescent
4 bd · 3 ba · 2,500 sqft
7018 Cadiz Crescent
3 bd · 2 ba · 1,100 sqft
1617 Trotwood Avenue
4 bd · 5 ba · 3,500 sqft
3257 Sir Johns Homestead
4 bd · 2 ba · 1,500 sqft
6772 Dolmage Court
3 bd · 2 ba · 1,500 sqft
1149 Mesa Crescent
4 bd · 3 ba · 2,500 sqft

Living in Mississauga: Location & Amenities

Transit, schools, parks and everyday places near this home. Select any place to open it on Google Maps.

Costs, Mortgage & Rental Return for 5576 Middlebury Dr

What it could cost each month, today's rates from our mortgage partner, and what it could return as a rental.

Mortgage: $7,369; 20% down · 25 years · 5.5% assumed
Property tax: $825; 0.66% mill rate · ON
Total per month: $8,194; Before utilities, insurance and fees

Figures are Summitly estimates for illustration only — not from TRREB or the MLS® feed, and not a mortgage approval, appraisal, or financial advice.

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Monthly cost

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Down payment

Rate (%)

Years

An estimate, not a quote. Utilities and insurance are extra.

Affordability calculator

Estimated monthly payment

$7,369

/mo

based on the purchase price of $1,499,999

Down payment20%

$300,000 cash

Amortization25 yr

$1,199,999 financed

Rate5.50%

$1,010,714 total interest

Principal54%$1,199,999

Interest46%$1,010,714

20% down · 25-yr amortization · 5.50% rate. Principal & interest only — taxes, condo fees, and insurance not included.

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Figures are Summitly estimates for illustration only — not from TRREB or the MLS® feed, and not a mortgage approval, appraisal, or financial advice.

Rental income potential

Est. monthly rent

low–high

Gross yield

rent × 12 ÷ price

Cap rate (est.)

net of tax + fees

Summitly AI estimate for discussion only — not from TRREB or the MLS® feed, and not an appraisal or investment advice. Yield and cap rate are derived from the estimated rent versus the asking price.

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Listing brokerage: RE/MAX ESCARPMENT REALTY INC., BrokerageMLS® W13791082 · Listing data last updated November 9, 2026

Listing data comes from the Toronto Regional Real Estate Board (TRREB) and is deemed reliable but not guaranteed. Shown on Summitly by Coldwell Banker Summit Realty, Brokerage, which is not the listing brokerage. The information provided herein must only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate and may not be used for any commercial purpose or any other purpose. © 2026 Toronto Regional Real Estate Board. All rights reserved.

Mortgage financing is arranged through Mortgage Squad Advisors. Summitly is the technology platform that powers this site. Estimated values, AI insights, calculator results, and rental projections shown on this page are generated by Summitly and are not provided by, reviewed by, or sourced from TRREB, the MLS®, or the listing brokerage; they are not appraisals or opinions of value. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by the Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The Coldwell Banker® name and logo are trademarks of Coldwell Banker Real Estate LLC.

For sale· listed Sep 15· $600/sq ft

Estimated monthly mortgage$7,369/moMortgage only · 20% down · 5.5% assumed

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5.0 · Google rating for Coldwell Banker Summit Realty, Brokerage · as of September 2026

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