Forest Hills Homes with Private Pool type

Forest Hills Homes with Private Pool type

Welcome to Forest Hills, a hidden gem nestled in the heart of Winter Park, Florida. This enchanting subdivision is renowned for its picturesque landscapes, friendly community atmosphere, and proximity to the vibrant culture of downtown Winter Park. With its lush greenery and serene surroundings, Forest Hills offers a tranquil retreat while still being just a stone’s throw away from the bustling city life.

One of the standout features of homes in Forest Hills is the availability of private pools, making them perfect for families and individuals who cherish outdoor living. Imagine stepping out into your own backyard oasis, where you can soak up the Florida sun, host summer barbecues, or enjoy a refreshing dip after a long day. These homes are designed to provide both comfort and luxury, with spacious layouts that seamlessly blend indoor and outdoor living.

Living in Forest Hills means embracing a lifestyle filled with convenience and leisure. The subdivision is conveniently located near top-rated schools, lush parks, and a variety of shopping and dining options. Whether you’re strolling through the charming streets of Winter Park, enjoying a scenic boat ride on the nearby lakes, or exploring the local art scene, there’s always something to do.

In Forest Hills, you’re not just buying a home; you’re investing in a lifestyle. With its beautiful homes featuring private pools and a community that feels like family, this subdivision is the perfect place to call home. Discover the magic of Forest Hills and envision the life you’ve always dreamed of in this idyllic Winter Park neighborhood.

Newest Forest Hills Homes with Private Pool type

$479,900
4 Beds ⋅ 3 Baths ⋅ Forest Hills SubDv. ⋅ 34690 Zip Code
Welcome to true waterfront living in this beautifully remodeled 4-bedroom, 3-bath home with direct Gulf access, incredible privacy, and upgrades throughout. Located along a scenic bend of the river, the backyard overlooks a private island preserve, so there are no rear neighbors—just peaceful water views and frequent visits from dolphins, manatees, and local wildlife. The home has remained high and dry during recent storms, offering added peace of mind. Inside, the split floorplan includes two private en suites on opposite sides of the home, making it perfect for multigenerational living, guests, or anyone who wants extra privacy. The brand-new kitchen features updated appliances, a Moen motion-sensor faucet with WiFi controls, and a clean, modern design. Major improvements include a 2025 whole-home Halo water treatment system, Uponor PEX plumbing, propane tankless water heater, new doors and windows, added attic insulation, and a generator-ready electrical setup. Outside, enjoy the heated pool with new 2024 pump and heat pump, a gravity overflow drain, private dock, and 10,000-pound boat lift with new stainless-steel cables. Additional features include an EV charging outlet, commercial-grade garage door opener, rebuilt garage door, WiFi-controlled sprinkler system supplied by a private well, ADT security system, Ring doorbell, garage camera, 2018 roof, and 2018 HVAC system. This move-in-ready home combines modern updates, waterfront privacy, and the relaxed Florida lifestyle buyers are looking for. Schedule your private showing today!

1166 Chancellor Drive, Holiday
$4,950,000
4 Beds ⋅ 7 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code
Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury living. Showcasing his signature aesthetic, the home emphasizes sleek architectural lines, refined finishes, and a seamless connection between indoor and outdoor spaces. Expansive walls of glass flood the interior with natural light and create a striking façade that embodies its contemporary elegance. The main living areas are designed for both entertaining and everyday living. A dramatic two-story living room is anchored by designer furnishings, which extend throughout the home, while the spacious dining area comfortably accommodates large gatherings. The adjacent family room continues the modern aesthetic with a built-in media wall, sleek fireplace, textured design elements, and a triple sliding door connecting the indoor and outdoor spaces. Ready for any caliber of chef, the kitchen boasts Thermador appliances, along with extensive cabinetry and countertop space, soft-close drawers, a waterfall edge island, generously sized pantry, and reverse osmosis water filtration. A private home theater on the main level offers a true cinematic experience with surround sound, custom seating, and blackout shades, along with a stylish wet bar, providing additional space for entertaining. The home’s Crestron automation system is discreetly integrated, allowing full control of lighting, climate, and technology from a single interface. Upstairs, a striking floating staircase leads to a gallery-style landing overlooking the living space below. For those exhausting days, you can instead take a ride on the elevator. The expansive primary suite features a sitting area, a custom closet, and terrace access. The spa-inspired primary bath includes dual rain showers with body sprays, a soaking tub, and dual vanities with elegant finishes. Additional second-floor amenities include a fitness room with steam shower and sauna, an additional en-suite bedroom, one of the two laundry rooms, and access to an upper-level terrace overlooking the landscaped grounds and pool. Two en-suite guest bedrooms are conveniently tucked away on the first floor for maximum privacy. Offering four bedrooms, five full bathrooms, and two half baths, the home delivers both comfort and sophistication at every turn. Thoughtfully integrated automated shades provide effortless privacy, while the advanced air purification systems and whole-home water softener complement the home's advanced smart features. This residence is offered fully furnished with curated Restoration Hardware pieces, including custom-selected furniture, lighting, rugs, and artwork that enhance its cohesive design. Outdoor living is equally impressive, with covered lanai spaces enhanced by automated roll-down screens, designer furnishings, a summer kitchen with gas grill and ventilation, and tranquil poolside views. The property also includes a split, three-car garage with a large driveway protected by a gated entrance. Completing this extraordinary dwelling is its location in the heart of Winter Park. This lakeside residence sits minutes from Park Ave Shopping, Rollins College, AdventHealth, multiple Botanical Gardens and Museums, well-rated grade schools, and highway access. Schedule your private showing today and experience the Winter Park lifestyle firsthand.

231 Chelton Circle, Winter Park
$3,235,000
5 Beds ⋅ 6 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code
This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately introduces the home’s refined aesthetic, offering a direct line of sight to the gorgeous herringbone white oak floors in the great room and the sparkling pool just beyond the full glass doors. Anchored by a sleek linear gas fireplace with custom built-ins and floating shelves, the great room provides an inviting yet sophisticated gathering space. The open-concept chef’s kitchen is a showpiece in both form and function. Outfitted with Wolf and Sub-Zero appliances, it boasts an eight-burner range with one-and-a-half ovens, an oversized Sub-Zero French door refrigerator with a freezer drawer, a built-in microwave drawer, and a walk-in pantry featuring a wine and beverage tower. Marble counters in all baths continue the home’s commitment to refined finishes. The main level primary suite is a serene retreat with a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub framed by dramatic four-by-ten-foot porcelain slabs, a custom walk-in closet, and a private water closet. A flexible fifth bedroom with an ensuite bath offers the perfect option for an office or den. A striking glass-railed staircase leads to the second level, where a spacious lounge area opens to a private covered patio. Three additional ensuite bedrooms, each with custom closet systems, complete the upstairs living quarters. Designed for indoor-outdoor living, the expansive covered lanai includes a summer kitchen with a grill, hood vent, refrigerator, sink, and a dedicated half bath. Overlooking lush landscaping with tropical Clusia hedges and Foxtail palms, the brand-new pool is finished with designer tile that lends a stylish, resort-quality flair. Additional highlights include a spacious storage closet under the staircase, oversized two-car garage, 500-gallon propane tank for easy generator connection, stone paver driveway and durable metal roof. Wonderfully located in a picturesque neighborhood, the property is just minutes from the boutiques and dining of Park Avenue, top-rated public and private schools and offers convenient access to downtown Orlando, the attractions, as well as area airports. A rare opportunity to own a newly constructed home of such quality and craftsmanship in one of Winter Park’s most sought-after neighborhoods.

1821 Englewood Road, Winter Park
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