Welcome to 445 Kennedy Circle, Milton, located in the desirable Cobban neighbourhood. This detached two-storey home offers 4 bedrooms, 4 bathrooms, approximately 2,114 sq. ft. of living space, and a single-car garage. The home features 10-foot ceilings on the main floor, 9-foot ceilings on the second floor, hardwood flooring on the main level and stairs, and an open-concept living and dining area. The kitchen boasts quartz countertops, a large centre island with a breakfast bar, and ample natural light. A fireplace adds warmth to the living space, while the main-floor laundry provides everyday convenience. The property also features a separate basement entrance and a legal basement with 2 bedrooms, a full bathroom, a kitchen, and separate laundry facilities, offering potential for additional living arrangements or rental income, subject to applicable requirements. Enjoy a fully fenced backyard, ideal for outdoor relaxation. Conveniently located close to schools, parks, shopping, everyday amenities, and major highways, including Highways 401 and 407. An excellent opportunity for families and buyers seeking additional space and flexibility.
4 bedrooms, 4 bathrooms, about 2,000 sq ft, works out to roughly $663 per square foot, the bed-to-bath ratio is generous. Chat with Zara if you'd like a deeper read on whether this detached fits your budget and timing.
Inside 445 Kennedy Cir W
Every detail from the listing, in one place.
Type
Detached
Style
2-Storey
Living space
2000-2500 sq ftas stated on the listing
Parking
2 spacesYes garage
Basement
Apartment, Separate Entrance
Features & systems
Parking & garage
Garage
Yes
Parking spaces
2
Interior
Basement
Apartment · Separate Entrance
Lot & land
Lot size (sqft)
0
Listing & possession
Property style
2-Storey
Property class
Detached
445 Kennedy Cir W Price & Sale History
Earlier listings of this property, list-price changes, and the most recent annual property tax on the listing.
For saleListedThis listingMLS® W14131726$1,325,000
Sourced from MLS®. Includes earlier listings of this property on record.
What's it worth?
How 445 Kennedy Cir W Compares to the Milton Market
Zara compares it with recent sales of similar homes nearby. It's a guide, not an appraisal.
Independent mortgage broker · OAC · rates subject to change and underwritingMortgage Squad →
Referral disclosure: Summitly may refer you to Mortgage Squad Advisors, an affiliated mortgage partner. You are free to choose any lender or mortgage professional.
Monthly cost
Enter a rate to see the monthly cost
An estimate, not a quote. Utilities and insurance are extra.
Affordability calculator
Estimated monthly payment
$6,509
/mo
based on the purchase price of $1,325,000
$265,000 cash
$1,060,000 financed
$892,798 total interest
Principal54%$1,060,000
Interest46%$892,798
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.
For homeowners nearby
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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.
Similar homes for sale nearby in Milton
Other 3–4 bed homes for sale in Milton around $1.3M.
Average days on market32Homes sold in about 32 days on average.
Sale-to-list ratio97.7%On average, homes sold below asking.
Active listings576Homes for sale here right now.
Median vs prior 90 days+1.7%Compared with May 3 – Aug 1, 2026: prices up.
Based on 575 sales from Aug 1 – Oct 30, 2026 (448 in the prior 90 days). Aggregate MLS® figures for closed sales; individual sold prices are shown only to signed-in members.
445 Kennedy Cir W is listed at $1,325,000 (MLS® W14131726). Summitly updates the price as soon as the MLS® record changes.
Is $1,325,000 a good price for 445 Kennedy Cir W?
Summitly rates it Fair Price: the asking price is Within 3% below to 5% above Zara's estimate, an estimate built from recent sales in Milton. The rating is an automated opinion, not an appraisal; "What's it worth?" on this page shows how it is worked out. See Zara's estimate
Has the price of 445 Kennedy Cir W changed?
No — 445 Kennedy Cir W is still listed at its original asking price of $1,325,000.
How many bedrooms and bathrooms does 445 Kennedy Cir W have?
445 Kennedy Cir W has 4 bedrooms and 4 bathrooms, with about 2,000–2,500 square feet of living space. It is a detached home in Milton.
Is 445 Kennedy Cir W close to transit?
The nearest rapid-transit station is Milton GO Station (Milton GO), about 4.3 km in a straight line. Distances are straight-line, not walking routes; check the transit agency for routes and schedules.
How much would the monthly mortgage be on 445 Kennedy Cir W?
About $6,509 a month — principal and interest on $1,325,000 with 20% down ($265,000), a 25-year amortization and an assumed 5.5% interest rate. The mortgage calculator on this page lets you change the down payment, amortization and rate.
How does 445 Kennedy Cir W compare with other homes in Milton?
Its asking price of $1,325,000 is about 44% above the median sold price in Milton over the last 90 days, $920,000, across 575 closed sales on the TRREB MLS®. A city median mixes every type and size of home, so the comparable sales on this page are the closer guide.
Has 445 Kennedy Cir W been sold before?
Summitly has no earlier MLS® sale or lease of 445 Kennedy Cir W on record from the last two years. Older records aren't shown under TRREB rules.
Where is 445 Kennedy Cir W?
445 Kennedy Cir W is in Milton, ON. Schools, transit, parks and shops nearby are under Location & lifestyle on this page.
How long has 445 Kennedy Cir W been on the market?
445 Kennedy Cir W was listed today (October 30, 2026).
What is the price per square foot of 445 Kennedy Cir W?
About $530 to $663 per square foot: the asking price of $1,325,000 over the 2,000–2,500 sq ft the listing gives as its size range.
Does 445 Kennedy Cir W have parking or a garage?
Yes — the listing gives 2 parking spaces. Garage: Yes.
