Maitland Shores
Homes for Sale in Winter Park, FL
All 364 homes for sale in Winter Park, FL · median $684,500 · 158 homes for sale in 32789 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 1 closed sale in Maitland Shores Second Add in Winter Park, FL, the most recent in December 2015. 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).
The current MLS snapshot for Maitland Shores Add carries no pricing history and no listed amenities, which tells you as much as any number would: this is a quiet, low-turnover pocket where activity has not generated a data trail recently. That absence of a track record is itself the market condition here, not a gap in our research.
For a buyer or seller, that means the usual shortcuts, comparable sales, posted community features, do not apply cleanly. Any decision on value or fit has to be built from the individual home and its immediate street, not from a neighborhood-wide pattern that simply is not present in the current feed.
Nearby homes for sale
No active listings inside Maitland ShoresHomes for Sale in Winter Park, FL 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
Maitland Shores Add sits within Winter Park in Orange County, an established address without a recent run of MLS activity to draw broad conclusions from. The name points to a platted, water-adjacent section of the city rather than a master-planned or amenity-driven community.
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.
County records show 4 qualified sales in Maitland Shores across 2024–2025 (2 in 2024, 2 in 2025), median $615,000 — 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 Maitland Shores is best for.
Best for
- A buyer targeting a particular home in Winter Park regardless of neighborhood-level data
- Someone comfortable doing property-specific diligence rather than leaning on published comps
- A buyer or seller who values a quiet, low-turnover setting over an amenity-driven one
Probably not for
- A buyer who wants a documented pricing history before making an offer
- Someone shopping specifically for listed community amenities
- A buyer who needs recent neighborhood comparables to feel confident in a number
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, 244 homes are on the market and 25% are under contract — a steady corner of Winter Park.
Across Orange County, 5,909 homes are active and 1,877 pending (24% 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 Maitland Shores specifically. Momentum Research analysis of MLS records.
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 Community With No Data Trail
Every neighborhood we cover gets read the same way: what does the current MLS feed actually show. Here, it shows no active or recent listings carrying pricing or amenity detail, and no community features identified. That is not unusual for small, established plats that turn over infrequently, it simply means the story has to be told home by home.
If you are looking at a specific address in Maitland Shores Add, the right approach is a direct evaluation of that property, its lot, its condition, its position relative to Winter Park's surrounding streets, rather than leaning on neighborhood-level statistics that do not currently exist in the feed.
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 pocket like this, where the public data is thin, the value we add is direct legwork: pulling whatever comparable activity exists nearby in Winter Park, walking the property itself, and being straightforward about what we do and do not know before you commit to a number.
Maitland Shores 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 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.
See all homes for sale in Winter Park →
Should you buy in Maitland Shores?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2015 (1 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.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Maitland Shores Add fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Maitland Shores
Where is Maitland Shores?
Maitland Shores is a community in Winter Park, Orange County, Florida, ZIP 32789.
Are there homes for sale in Maitland Shores right now?
No active listings inside Maitland Shores at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Maitland Shores have an HOA or CDD?
No HOA is on record for Maitland Shores in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
Explore more neighborhoods near Maitland Shores with Momentum Realty’s local guides.