Cortland Park
Homes for Sale in Winter Park, FL
All 356 homes for sale in WINTER PARK, FL · median $697,000 · 167 homes for sale in 32789 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, the MLS records 21 closed sales in Cortland Park in Winter Park, FL since 2004, the most recent in July 2026. Across Winter Park as a whole, 494 homes closed in the last 12 months at a median of $449,000, 33 median days on market, with 128 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $7,490 ($6,810 with the full homestead exemption).
| Location | WINTER PARK, Orange County, FL · ZIP 32789 |
|---|---|
| Homes in the community | 46 (FL DOR 2025 assessment roll) |
| Years built | 1925–2022 (median 1951.5) |
| Typical living area | 2,930 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 83% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Cortland Park key facts,” movewithmomentum.com/neighborhoods/cortland-park-winter-park, data as of September 20, 2026.
Cortland Park's story is really a story about age and footprint, not amenities. A median year built of 1951, inside a range that stretches all the way to 2022, tells you this pocket has been rebuilt and infilled in pieces for decades rather than delivered as one subdivision at one moment. That mix is what actually drives value here - a 1950s original on a given street can sit near a full teardown-rebuild, and condition does more pricing work than location within the neighborhood.
Right now there is nothing active on the MLS and only a single closing in the most recent window, so there is effectively no live market to read off current listings. That is not the same as no demand - with 85 homes total and roughly seven in ten owner-occupied under homestead exemption, turnover here has always been slow. For a buyer, that means patience and off-market legwork matter more than scrolling portals. For a seller, it means a well-prepared listing has very little competing inventory to get lost against.
Nearby homes for sale
No active listings inside Cortland Park right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Cortland Park is a small, established pocket of 85 homes in Winter Park where the housing stock spans more than a century of construction, from early-1900s originals to recent rebuilds, with a median home dating to 1951.
Stellar MLS sales records identify 22 homes in Cortland Park that have changed hands since 2004, built between 1925 and 2012 (median 1948), with a median living area of about 3,118 sq ft and a typical 4-bedroom, 3-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
County records show 6 qualified sales in Cortland Park across 2024 - 2025 (2 in 2024, 4 in 2025), median $2.10M - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Cortland Park is best for.
Best for
- A buyer targeting an established Winter Park location and willing to wait for the right listing to surface off-market.
- A buyer comfortable evaluating each home individually, since construction era and condition vary widely house to house.
- A long-term hold buyer who values a low-turnover pocket over a fast-moving, amenity-driven subdivision.
Probably not for
- A buyer who wants to compare several active listings side by side before deciding - there is currently nothing on the market to compare.
- A buyer who wants defined community amenities like a pool, clubhouse, or organized common areas.
- A buyer uncomfortable with mixed-vintage housing stock spanning more than a century of construction.
The market around Cortland Park
Cortland Park is too small for its own price trend, so here is the market around it.
In ZIP 32789, 239 homes are on the market and 23% are under contract — a steady corner of Winter Park.
Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).
In ZIP 32789 (WINTER PARK), 390 homes closed in the last 12 months at a median of $635K ($396/sq ft), up 7.6% year over year, with a median 39 days on market. Right now 91 active and 26 pending listings put supply at about 5.2 months - a balanced market. See the live ZIP 32789 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Cortland Park specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in Cortland Park, WINTER PARK
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
The Cortland Park buying strategy.
If we were buying in Cortland Park today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Cortland Park.
An older, owner-held pocket with almost no active inventory
The living space profile skews larger than a typical infill neighborhood - a median of 2,394 square feet - which suggests many of the homes here have been expanded or rebuilt at some point rather than left untouched at their original 1900s-era footprint. Combined with the wide year-built spread, this is a community where two homes on the same block can represent very different generations of construction, finish level, and system age, even if the lot sizes and street pattern look similar.
The homestead share of just over 70% is worth sitting with: it points to a neighborhood where most owners have filed for the exemption tied to a primary residence, which typically correlates with longer hold periods and less speculative turnover. That, paired with zero active listings and only one closing in the current window, means Cortland Park does not behave like a fast-moving subdivision - inventory is thin by nature, not by a temporary market shift, and no community amenities are listed in current MLS data, so whatever draws a buyer here is the home and the location itself, not a shared clubhouse or pool.
The location and the amenities are priced into every listing in Cortland Park. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
With no active listings to compare against, pricing a home in Cortland Park correctly means pulling from off-MLS context and recent comparable closings rather than trusting what is currently showing online - that is where a broker who tracks this pocket closely earns their keep, on both the buy and sell side.
Cortland Park in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Cortland Park buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Cortland Park sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Cortland Park, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Cortland Park home worth?
Get a no-obligation home value based on real comparable sales in Cortland Park, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Recently off market in Cortland Park
Homes in Cortland Park that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 1 on record.
- 250 Cortland Avenue · off market
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Orange County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Orange County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
Frequently Asked Questions
How many homes are in Cortland Park?
What share of Cortland Park is owner-occupied?
When were the homes in Cortland Park built?
Who is the best real estate agent for Cortland Park?
How do I find a top Winter Park real estate agent who knows Cortland Park?
Can Momentum Realty connect me with an agent for Cortland Park?
Where is Cortland Park, and what county is it in?
Should you buy in Cortland Park?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 1, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 32789)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2004 (21 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how Cortland Park fits the bigger picture — live prices, inventory, and Momentum Scores:
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