About Regency Oaks Neighborhood
Regency Oaks sits east of Daniels Road in southwestern Winter Garden, accessed via Stone Crest Boulevard inside the Stone Crest master community. M/I Homes developed the subdivision over a two-year period from 2003 through 2005, delivering 163 single-family homes on a sidewalk-lined street grid threaded with community ponds and water features. The mix of architectural styles — Cape Cod, Florida vernacular, ranch, contemporary, Mediterranean, and bungalow — gives the streetscape variation that's atypical of production builds from that era.
Floor plans range from cozy 1,350-square-foot three-bedroom designs to roughly 3,600-square-foot five-bedroom homes with bonus rooms, jack-and-jill baths, and formal living areas. Two- and three-car garages are standard. Owner's suites typically feature separate tubs and showers, dual vanities, and walk-in closets. Some homes back to pond views, and a number include private screened-in pools — a desirable feature given that the community pool is shared across Stone Crest's five sub-neighborhoods.
The community is non-gated, which keeps HOA dues lower than the gated alternatives in the area while still delivering shared Stone Crest amenities and the quiet residential character that comes with an off-arterial location. Daniels Road handles the through-traffic; Regency Oaks itself stays internal. The neighborhood is roughly 2 miles south of historic Plant Street and about the same distance north of the SR-429 / SR-50 interchange, putting most West Orange destinations within a 10-minute drive.
📊 Quick Facts
🏡 What Makes Regency Oaks Distinct
- Range of floor plans in one subdivision. Few 163-home communities cover 1,350 to 3,600 sq ft. First-time buyers, downsizers, and growing families can all find a fit on the same street grid.
- Stone Crest amenities without Stone Crest's gate. Regency Oaks residents access the shared pool, tennis courts, playground, and scenic park while paying non-gated HOA dues.
- Architectural variety from a single builder. M/I delivered six distinct elevation families here, so the streetscape doesn't read as cookie-cutter the way some early-2000s production neighborhoods do.
- Pond and water-feature lots. Internal ponds give a meaningful number of homes water views without requiring a lakefront premium.
- Established trees. Twenty-plus years of canopy growth puts Regency Oaks ahead of newer Winter Garden builds on shade and curb appeal.
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Regency Oaks Location & Connections
Regency Oaks sits on the east side of Daniels Road in southwestern Winter Garden, tucked inside the Stone Crest master community. The location splits the difference between historic downtown to the north and the SR-50 retail/highway corridor to the south, with Winter Garden Village at Fowler Groves and the AdventHealth Winter Garden hospital campus both within a short drive. Daniels Road handles north-south traffic; SR 429 and Florida's Turnpike are reached within minutes via SR-50.
🏘️ Adjacent Neighborhoods & Areas
- Cobblestone — adjacent subdivision
- Foxcrest — sister neighborhood within Stone Crest
- Grove Park — sister neighborhood within Stone Crest
- Grovehurst and Glynwood — the other two sister neighborhoods completing the five-community Stone Crest master association
- Conservation land bordering portions of the master community, plus a Winter Garden fire station nearby for emergency response coverage
Stone Crest is a five-neighborhood master association (Glynwood, Regency Oaks, Grovehurst, Foxcrest, Grove Park) sharing a pool, tennis courts, playground, and scenic park managed by Sentry Management. Each sub-neighborhood retains its own HOA for internal common areas.
🚗 Detailed Commute Times
- Downtown Orlando: ~25 minutes (~16 miles via SR-50 or SR-429 / I-4)
- UCF Campus: ~35 minutes (~28 miles)
- Walt Disney World: ~18 minutes (~10 miles via SR-429)
- Universal Orlando: ~22 minutes (~15 miles)
- SeaWorld Orlando: ~25 minutes (~17 miles)
- Cocoa Beach: ~75 minutes (~70 miles via SR-528)
- Lake Nona Medical City: ~35 minutes (~25 miles)
- Historic Downtown Winter Garden / Plant Street: ~6 minutes (~2.5 miles via Daniels Road)
✈️ Airport Access
- Orlando International Airport (MCO): ~30 minutes (~22 miles via SR-429 and SR-528)
- Orlando Sanford International Airport (SFB): ~45 minutes (~35 miles via SR-429 and I-4)
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Regency Oaks Amenities & Lifestyle
Day-to-day life in Regency Oaks centers on the shared Stone Crest amenities and the short drive into either historic downtown Winter Garden or the SR-50 retail belt. The combination of an established 20-year-old community, sidewalks along every street, and pond-side walking routes gives the neighborhood the kind of mature feel that newer 34787 builds are still years away from delivering.
🏊 Neighborhood & Stone Crest Amenities
Regency Oaks residents have access to the shared Stone Crest master amenity package alongside neighbors from Glynwood, Grovehurst, Foxcrest, and Grove Park:
- Community pool with adjacent parking
- Tennis courts adjacent to the pool area
- Children's playground
- Scenic park / waterfront park near the main entrance
- Internal community ponds and water features
- Sidewalks throughout the neighborhood
Master-community amenity access is managed by Sentry Management. For access cards, residents contact Sentry directly through their sub-neighborhood HOA.
🛍️ Shopping & Services
Winter Garden Village at Fowler Groves — the area's 80-plus store open-air lifestyle center — sits roughly 3 miles south on Daniels Road, anchoring most everyday shopping with Target, Best Buy, Whole Foods, Ross, and a long restaurant lineup. Historic Plant Street handles boutique and specialty retail.
For comprehensive shopping information: View our Winter Garden Shopping Guide →
🍽️ Restaurants
Dining splits between the Winter Garden Village restaurant cluster and the historic downtown core. Plant Street Market and Crooked Can Brewery anchor downtown's food-hall scene; the Edgewater Hotel Tasting Room handles brunch and tasting menus a few blocks away.
For comprehensive restaurant information: View our Winter Garden Restaurants Guide →
🎭 Arts & Culture
Historic downtown anchors the cultural scene with the Garden Theatre, the Winter Garden Heritage Museum, the Central Florida Railroad Museum, and SOBO Art Gallery.
For comprehensive arts & culture information: View our Winter Garden Arts & Culture Guide →
🏃 Health & Wellness
AdventHealth Winter Garden on Fowler Grove Boulevard is the closest full-service hospital, roughly 3 miles south of Regency Oaks. Health Central Hospital in neighboring Ocoee provides a secondary full-service option to the east.
For comprehensive health & wellness information: View our Winter Garden Health & Wellness Guide →
🌳 Parks & Recreation
Newton Park on Lake Apopka sits at the downtown lakefront for sunset views and the West Orange Trail terminus. The 128-acre Oakland Nature Preserve sits minutes west.
For comprehensive parks & recreation information: View our Winter Garden Parks & Recreation Guide →
⚽ Sports & Athletics
The West Orange Country Club handles private golf, tennis, and pickleball. The West Orange Trail draws cyclists straight through downtown for recreational riding, and the shared Stone Crest tennis courts give residents on-site play without a club membership.
For comprehensive sports & athletics information: View our Winter Garden Sports & Athletics Guide →
🎉 Fun Things to Do
The Winter Garden Farmers Market draws crowds to Plant Street every Saturday, and Fridays on the Plaza brings free live music to the Plant Street Pavilion each week.
For comprehensive events & activities information: View our Winter Garden Events & Things To Do Guide →
🎓 Schools
Regency Oaks is likely zoned for Orange County Public Schools — verify current attendance zones with the OCPS School Locator before relying on this for a purchase decision:
- Elementary: Maxey Elementary or Tildenville Elementary (the SR 50 / Daniels Road corridor cluster per the Winter Garden hub mapping)
- Middle: SunRidge Middle
- High: West Orange High
Note: OCPS attendance zones change periodically. Always verify current zoning at ocps.net before making a school-based decision.
For comprehensive school information: View our Winter Garden Schools Guide →
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How Regency Oaks Compares
Regency Oaks competes most directly against other established M/I-era subdivisions in southwestern Winter Garden and against newer non-gated 34787 builds. The value proposition is established trees, a wider floor-plan range than typical for the price, and shared master-community amenities — all without the higher dues that come with a gate.
| Feature | Regency Oaks | Newer 34787 Builds | Gated Winter Garden Options |
|---|---|---|---|
| Year Built | 2003–2005 | 2018–present | Varies (2005–present) |
| Home Size Range | ~1,350–3,600 sq ft | ~1,800–3,200 sq ft | ~2,200–4,500 sq ft |
| Gated | No | Mixed | Yes |
| Tree Maturity | Established (20+ years) | Young / developing | Varies |
| CDD Fee | No | Often yes | Varies |
| Shared Amenities | Stone Crest master (pool, tennis, playground, park) | Varies by build | Resort-style typical |
| HOA Dues | Lower (non-gated) | Mid | Higher (gated) |
💡 Value Proposition: Regency Oaks delivers shared master-community amenities and a wide range of M/I floor plans inside a non-gated 20-year-old streetscape — meaningfully lower HOA dues than the gated alternatives nearby, with established trees and pond-side lots that newer 34787 builds can't match.
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Regency Oaks HOA & CDD Information
Regency Oaks has its own sub-neighborhood HOA — managed by Lighthouse Property Management — that handles common areas internal to the subdivision. Separately, the Stone Crest Master Association — managed by Sentry Management — handles the shared amenity package available to all five sub-neighborhoods (Glynwood, Regency Oaks, Grovehurst, Foxcrest, Grove Park). Both layers of dues apply.
The community does not carry a Community Development District (CDD) assessment, which is a meaningful cost advantage versus many newer Winter Garden and Horizon West subdivisions that bundle CDD fees on top of HOA dues.
💰 HOA Fees & Management Contacts
HOA fees and management company contact information often change. Please contact us and we will provide the current Regency Oaks sub-neighborhood HOA fee, the Stone Crest Master Association fee, the combined payment schedule, and direct contact information for both Lighthouse Property Management and Sentry Management. We can also check whether there are any current or upcoming special assessments at either layer.
📋 What HOA Fees Cover
- Stone Crest master amenities — pool, tennis courts, playground, scenic park
- Master-community common-area landscaping and maintenance
- Regency Oaks sub-neighborhood common areas, ponds, and water features
- Internal sidewalk and street lighting upkeep where applicable
- Architectural review and covenant enforcement
- Master association insurance and reserve funding
- Sentry Management amenity access cards (master)
📚 More Information
For background on how Florida HOAs and CDDs operate, see our explainers on What's an HOA? and What's a CDD?
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David Myers
