Under Construction. UPDATE: Ahead of schedule with an estimated completion is FEB 2026. Please see attached package for full renderings and finishes. 166 Hammock Preserve Loop offers one of the finest new construction custom homes in Winter Garden, FL. Built by AR Homes—celebrating over 40 years of luxury homebuilding—this Carrabelle model sits in the highly sought-after Oakland Park community. Boasting 3,186 sq ft of impeccably crafted living space, the two-story open-concept floor plan features four spacious bedrooms and four full baths, including a breathtaking second-floor primary suite complete with a generous walk-in closet, spa-inspired en-suite with dual vanities, and an oversized shower. Located on the first floor, a versatile flex room and dedicated guest suite accommodate growing families or visiting guests, while designer details—dramatic ceiling accents, high-end appliance package in the gourmet kitchen, and expansive living and dining areas—elevate the home’s luxurious feel. Outdoor living shines with a covered lanai, cabana, and open-air courtyard complete with fireplace, and an optional in-law or guest suite above the garage provides additional flexibility. Set amid tree-lined streets, scenic walking trails, and community events—from holiday festivals to yoga in the park and Bike & Dine gatherings—this property delivers an unparalleled lifestyle close to downtown Winter Garden’s boutique shopping, fine dining, and top-rated schools. Offered with a unique turnkey leaseback option for immediate returns or available for outright purchase, 166 Hammock Preserve Loop represents both an exceptional luxury residence and a sound investment in Central Florida’s strongest housing market. Photos shown are of a previously completed Carrabelle build for demonstration; contact us today for details, pricing, and customization options.
- Built in 2025
- 3 garage spaces
- $494.35/sqft
- Lot size: 6,914 sqft
- 319 days on market
- Directions: 1. Start from I-4 W in Orlando, FL 32806 2. Head southwest on I-4 W for 5.7 miles 3. Use the right lane to take the Miami exit (0.8 miles) 4. Keep right, following signs for Florida’s Turnpike N/Ocala, and merge onto Florida’s Turnpike (Toll road, 13.0 miles) 5. Use the right 2 lanes to take Exit 272 for FL-50 E toward Winter Garden (Toll road, 0.6 miles) 6. Merge onto W Colonial Dr (0.6 miles) 7. Turn left onto S Tubb St (0.3 miles) 8. Turn right onto E Oakland Ave (0.5 miles) 9. Turn left onto Winters Landing Dr (0.2 miles) 10. Continue straight onto Cyn Crk Trl (423 feet) 11. Turn right onto Eaglecrest Dr (148 feet) 12. Turn right again, and the destination will be on the left (0.1 miles) 166 Hammock Preserve Loop, Oakland, FL 34787
- County: Orange
- Geo subdivision: OAKLAND PARK
Nearby Schools
Tildenville Elem
Lakeview Middle
West Orange High
Features
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Exterior
Utilities
Structure
Pets, Accessibility & Amenities
Community Info
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Let's get in touch!
Let's get in touch!

Niles Harrison Pfeiffer
Central Florida REALTOR®
- Source: Stellar MLS
- MLS #: O6283425
Listing updated: January 6, 2026 at 6:46PM
Listing provided by: A.J. Lash, CORCORAN PREMIER REALTY
Last checked 0 seconds ago
Listing provided by: A.J. Lash, CORCORAN PREMIER REALTY
Last checked 0 seconds ago
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