Regency Oaks
Homes for Sale in Winter Garden, FL
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
Regency Oaks Ph 02 A-C is a mid-2000s subdivision in Winter Garden, with homes built between 2003 and 2008 and a median living area right around 2,483 square feet. That size profile is the real story on price here: these are substantial homes, and what separates one closing from the next is condition and updates, not floor plan gymnastics. With a median build year of 2005, the housing stock is now at the age where kitchens, roofs, and HVAC either have been addressed or are on the buyer's near-term list, and that shows up in the spread between asking prices.
This is a thinly traded snapshot — only two closings in the current window across 216 homes — so treat any single sale as a data point, not a trend. About 68% of homes here carry a homestead exemption, which tells you the bulk of the neighborhood is owner-occupied and turnover is measured. For sellers, that means low competing inventory but also a patient market; for buyers, it means you may wait for the right home rather than pick from many at once.
The 60-Second Overview
Regency Oaks Ph 02 A-C is an established, larger-home enclave in Winter Garden's Orange County footprint, built out over a five-year stretch in the mid-2000s and now settled into low-turnover ownership.
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.
The setting & the homes.
Aerial and on-site photos of Regency Oaks. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Regency Oaks
Regency Oaks
Regency OaksPhotos from Stellar MLS listings in Regency Oaks; content deemed reliable but not guaranteed.
Who Regency Oaks is best for.
Best for
- Buyers wanting a larger, established mid-2000s home who will wait for the right listing
- Long-hold owner-occupants comfortable in a low-turnover, owner-heavy neighborhood
- Buyers budgeting for near-term systems updates on a roughly twenty-year-old home
Probably not for
- Shoppers who need many homes on the market to compare at once
- Buyers seeking new construction or the latest floor plans
- Anyone needing to price a purchase off deep recent-sales data
The market around Regency Oaks
Regency Oaks is too small for its own price trend, so here is the market around it.
In ZIP 34787, 932 homes are on the market and 29% are under contract — a steady corner of Winter Garden.
Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).
ZIP and county figures describe the wider market, not Regency Oaks specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in Regency Oaks Ph 02 A-C, Winter Garden
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 October 2026 through October 2026. Deemed reliable but not guaranteed.
Regency Oaks on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
The Regency Oaks buying strategy.
If we were buying in Regency Oaks 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 Regency Oaks.
A condition-driven resale market
With 216 homes built in a tight 2003–2008 band, this is a cohesive community rather than a patchwork of eras. The median living space near 2,483 square feet points to two-story homes with room to spread out, and because everything is roughly the same vintage, buyers are effectively comparing maintenance histories more than architecture. A home with a newer roof and updated systems will read very differently on price than a comparable floor plan that has deferred those items.
The 68% homestead share signals a neighborhood held largely by long-term owners, which historically keeps inventory tight. That works two ways: sellers face little direct competition when they do list, but buyers should be prepared to move decisively when a well-kept home appears, since options at any given moment are limited.
The location and the amenities are priced into every listing in Regency Oaks. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a low-turnover community with few active listings, pricing lives or dies on condition-adjusted comparisons, not headline averages. We track the mid-2000s systems questions that actually move value here — roof, HVAC, kitchen age — and we help sellers position honestly and buyers underwrite the work a given home still needs.
Regency Oaks 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 Regency Oaks 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 Regency Oaks sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Regency Oaks, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Regency Oaks home worth?
Get a no-obligation home value based on real comparable sales in Regency Oaks, 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 homes for sale in Regency Oaks on the map →
Frequently Asked Questions
How many homes are in Regency Oaks?
What share of Regency Oaks is owner-occupied?
When were the homes in Regency Oaks built?
Who is the best real estate agent for Regency Oaks?
How do I find a top Winter Garden real estate agent who knows Regency Oaks?
Can Momentum Realty connect me with an agent for Regency Oaks?
Should you buy in Regency Oaks?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Regency Oaks with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 5, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (3 streets, ZIP 34787)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2014 (16 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 Regency Oaks Ph 02 A-C fits the bigger picture — live prices, inventory, and Momentum Scores: