This semi detached, 4 level back split may be the opportunity you've been looking for. Priced as one of the cheapest freehold homes in Orangeville, this could be your chance as a first time buyer to enter the market. Maybe you're an investor looking for a flip? Perhaps you'd like to earn some rental income? Maybe you're looking for a place to raise a family? The open concept main floor has an updated kitchen, while the upper level has 3 bedrooms and an updated 4 piece washroom. The ground floor has a spacious rec room with a kitchenette, 3 piece washroom and walk out to the back yard, while the basement has it's own entrance from the foyer, with a large rec room, a second kitchenette and another 3 piece washroom. Live upstairs and rent the lower level! Rent it all out! Live in the whole house yourself! With the right due diligence, the possibilities with this home are endless. Walking distance to both public and catholic elementary schools, as well as public high school.
3 bedrooms, 3 bathrooms, about 1,500 sq ft, works out to roughly $387 per square foot, the bed-to-bath ratio is generous. Chat with Zara if you'd like a deeper read on whether this semi-detached fits your budget and timing.
Inside 27 Madison Ave
Every detail from the listing, in one place.
Type
Semi-Detached
Style
Backsplit 4
Living space
1500-2000 sq ftas stated on the listing
Parking
3 spaces
Basement
Finished, Separate Entrance
Features & systems
Parking & garage
Parking spaces
3
Interior
Basement
Finished · Separate Entrance
Lot & land
Lot size (sqft)
0
Listing & possession
Property style
Backsplit 4
Property class
Semi-Detached
27 Madison Ave Price & Sale History
Earlier listings of this property, list-price changes, and the most recent annual property tax on the listing.
For saleListedThis listingMLS® W14152568$580,000
Sourced from MLS®. Includes earlier listings of this property on record.
What's it worth?
How 27 Madison Ave Compares to the Orangeville 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
$2,849
/mo
based on the purchase price of $580,000
$116,000 cash
$464,000 financed
$390,810 total interest
Principal54%$464,000
Interest46%$390,810
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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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 Orangeville
Other 2–3 bed homes for sale in Orangeville around $580K.
Average days on market34Homes sold in about 34 days on average.
Sale-to-list ratio97.4%On average, homes sold below asking.
Active listings164Homes for sale here right now.
Median vs prior 90 days+1.9%Compared with May 9 – Aug 7, 2026: prices up.
Based on 133 sales from Aug 7 – Nov 5, 2026 (119 in the prior 90 days). Aggregate MLS® figures for closed sales; individual sold prices are shown only to signed-in members.
Questions About 27 Madison Ave
How much is 27 Madison Ave listed for?
27 Madison Ave is listed at $580,000 (MLS® W14152568). Summitly updates the price as soon as the MLS® record changes.
Is $580,000 a good price for 27 Madison Ave?
Summitly rates it Excellent Deal: the asking price is 10% or more below Zara's estimate, an estimate built from recent sales in Orangeville. 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 27 Madison Ave changed?
No — 27 Madison Ave is still listed at its original asking price of $580,000.
How many bedrooms and bathrooms does 27 Madison Ave have?
27 Madison Ave has 3 bedrooms and 3 bathrooms, with about 1,500–2,000 square feet of living space. It is a semi-detached home in Orangeville.
How much would the monthly mortgage be on 27 Madison Ave?
About $2,849 a month — principal and interest on $580,000 with 20% down ($116,000), 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 27 Madison Ave compare with other homes in Orangeville?
Its asking price of $580,000 is about 22% below the median sold price in Orangeville over the last 90 days, $739,000, across 133 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 27 Madison Ave been sold before?
Summitly has no earlier MLS® sale or lease of 27 Madison Ave on record from the last two years. Older records aren't shown under TRREB rules.
Where is 27 Madison Ave?
27 Madison Ave is in Orangeville, ON. Schools, transit, parks and shops nearby are under Location & lifestyle on this page.
How long has 27 Madison Ave been on the market?
27 Madison Ave was listed today (November 5, 2026).
What is the price per square foot of 27 Madison Ave?
About $290 to $387 per square foot: the asking price of $580,000 over the 1,500–2,000 sq ft the listing gives as its size range.
Does 27 Madison Ave have parking or a garage?
Yes — the listing gives 3 parking spaces.
Does 27 Madison Ave have a basement, and is it finished?
The listing describes the basement as: Finished, Separate Entrance.
