Maitland Shores
Homes for Sale in Winter Park, FL
All 394 homes for sale in Winter Park, FL · median $636,250 · 169 homes for sale in 32789 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of November 2026, Maitland Shores 1St Add in Winter Park, FL has 1 home for sale. As of November 2026, the MLS records 14 closed sales in Maitland Shores 1St Add in Winter Park, FL since 2005, the most recent in March 2015. Across Winter Park as a whole, 887 homes closed in the last 12 months at a median of $499,000, 37 median days on market, with 326 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $8,320 ($7,650 with the full homestead exemption).
Maitland Shores 1st Addition is a small, established pocket of 103 homes with a build era spanning 1925 to 2024, and a median year built of 1991 - meaning the housing stock is a genuine mix of older construction and newer builds rather than a single-era subdivision. Median living area runs large at 3,363 square feet, which points to a community of substantial homes rather than starter product.
Current inventory is essentially nonexistent - one active listing and no closings recorded in the current window. That is not enough data to read a market trend; it means pricing here has to be built listing by listing, based on the specific home's age, condition, and size rather than any community-wide pattern. A homestead share of 71% also tells us most homes are owner-occupied under Florida's tax exemption, which tends to support steadier turnover than an investor-heavy pocket.
Figures in this note are as of July 22, 2026. The live market numbers elsewhere on this page update nightly and are newer.
The 60-Second Overview
A small, low-turnover community in Winter Park where large-format homes spanning nearly a century of construction sit on a single shared amenity - a park - rather than a resort-style package.
Stellar MLS sales records identify 71 homes in Maitland Shores that have changed hands since 2004, built between 1925 and 2025 (median 1997), with a median living area of about 3,534 sq ft and a typical 4-bedroom, 3.5-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.
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 Maitland Shores is best for.
Best for
- Buyers seeking a larger-format home and comfortable evaluating an individual property on its own merits
- Long-term owner-occupants who value stability over frequent resale activity
- Buyers open to a mix of older and newer construction rather than a uniform build era
Probably not for
- Buyers who want a resort-style amenity package beyond a shared park
- Anyone relying on recent comparable sales or active inventory to shape an offer
- Buyers seeking new or near-new construction exclusively, given the wide build-year spread
The market around Maitland Shores
Maitland Shores 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), 111 homes closed in the last 12 months at a median of $627K ($396/sq ft), down 21.6% year over year, with a median 42 days on market. Right now 34 active and 4 pending listings put supply at about 3.7 months - a buyer's market. See the live ZIP 32789 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Maitland Shores specifically. Momentum Research analysis of MLS records.
Homes For Sale Right Now in Maitland Shores
Live MLS inventory for Maitland Shores. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Maitland Shores listings as of 2026-11-12, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2015. Tap any home to ask about it.
Life at Maitland Shores
- Park · reported on 1 of 1 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Dommerich Elem · Elementary
- Maitland Middle · Middle
- Winter Park High · High
Zoned schools reflect the assignments reported on recent Maitland Shores listings and can change; always confirm with Orange County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Maitland Shores address.
Shop the zone: Homes zoned for Winter Park High High School
The Maitland Shores buying strategy.
If we were buying in Maitland Shores 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 Maitland Shores.
A Deep Mix of Eras, A Shallow Market
With only 103 homes total and construction dates ranging from 1925 to 2024, Maitland Shores 1st Addition does not read like a typical single-phase subdivision. The median year built of 1991 sits roughly in the middle of that range, which means buyers here are choosing between genuinely older construction, mid-century-plus rebuilds, and newer infill - each with different maintenance and system-age considerations that a size or price comparison alone won't surface.
The median living area of 3,363 square feet is substantial for the area, suggesting this community skews toward larger-format homes rather than compact or entry-level product. Combined with a 71% homestead share, the pattern is one of longer-term ownership rather than rapid resale - which explains why active inventory is thin. A single active listing and no recorded closings in the current window mean there is no reliable trend line right now; each transaction here has to be priced against the specific home, not a community average.
The location and the amenities are priced into every listing in Maitland Shores. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community this thin on active listings and closings, there is no shortcut through comparable sales data - pricing a home here requires digging into the individual property's age, condition, and square footage against the broader Winter Park and Orange County market. We do that work directly rather than leaning on a stale average, and we tell clients plainly when the data does not support a confident number yet.
Maitland Shores in 15 seconds.
Tools for a Maitland Shores 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 Maitland Shores sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Maitland Shores, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Maitland Shores home worth?
Get a no-obligation home value based on real comparable sales in Maitland Shores, 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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Should you buy in Maitland Shores?
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: November 12, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2005 (14 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.
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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.