Forest Hills Homes 

Forest Hills is a charming residential enclave nestled within the scenic city of Winter Park, FL, offering an exquisite real estate landscape. This community boasts a diverse array of homes, ranging from elegant single-family residences to luxurious estates, catering to various preferences and lifestyles. Each home exudes character and comfort, reflecting the area's rich history and architectural heritage.

Residents of Forest Hills enjoy an enviable location, with an abundance of nearby attractions and amenities to explore. The community's proximity to Winter Park's renowned cultural hub provides easy access to museums, art galleries, and theaters. The lush green spaces of Central Park and Mead Botanical Garden offer serene escapes for outdoor enthusiasts. Additionally, the charming Park Avenue district, with its upscale boutiques and dining options, adds to the allure of the area.

Convenience is a hallmark of life in Forest Hills, as residents have an array of nearby amenities at their fingertips. The community benefits from close proximity to essential services such as supermarkets, healthcare facilities, and schools. Furthermore, the Winter Park Village shopping center is just a stone's throw away, providing a one-stop destination for shopping, dining, and entertainment. With its blend of historic charm, modern convenience, and access to local attractions, Forest Hills stands as a captivating choice for those seeking a well-rounded and vibrant living experience in Winter Park, FL.

Available Forest Hills Homes For Sale

$3,395,000
5 Beds ⋅ 6 Baths ⋅ O6437722 MLS
Perfectly positioned in the heart of Old Winter Park, the quaint Forrest Hills neighborhood is lined with charming cobblestone streets that wind around Lake Sue. This custom home, designed and built by the celebrated Z-Properties, pairs timeless New England character with modern sensibilities. Every detail is intentional in this iconic design—nothing has been sacrificed. Situated on a 0.25-acre lot, a private courtyard welcomes you through a solid wood arched gate and along a slate pathway to the front door. Cedar shake detailing, a block wall surrounding the property, and classic architectural elements add to the style and charm of this Hamptons-inspired home. The residence features five bedrooms and five-and-a-half baths, including a first-floor primary suite and a dedicated guest house. Spanning 4,018 square feet, the home offers a thoughtfully designed floor plan with the primary suite on the first floor, while additional bedrooms and flexible living space are located upstairs. The guest house includes two ensuite bedrooms and a living room with vaulted ceilings and exposed wood beam details. Inside, a generous foyer welcomes you, where neutral-hued pine floors anchor the home and set a warm, inviting tone. Volume ceilings enhance the open floor plan, while an architectural skylight with transom windows floods the living room with natural light. A wall of custom built-in storage ensures everything has its place. The transition to the dining room is framed by backlit glass built-ins, while the centerpiece is a custom buffet accented by designer wall coverings and elegant lighting, creating a truly stunning entertaining space. Glass doors open to a covered lanai with tongue and groove ceiling a summer kitchen with pellet grill and bar seating, all overlooking the sparkling pool. A turf grass surround minimizes maintenance while providing year-round beauty. The lanai connects to separate guest house featuring 2 ensuite bedrooms and living space. The center courtyard is intimate, offering incredible privacy for this special place. The kitchen is beautifully appointed with paneled appliances, a Thermador chef's range with pot filler, and a stunning marble center island with counter seating. A butcher block work surface provides additional prep space, while a floor-to-ceiling wall of paneled cabinetry maximizes storage and organization. A breezeway drop zone with a built-in desk creates a functional everyday workspace, complemented by a separate laundry room. This home doesn't miss a beat. With an exceptional location, thoughtfully considered design, and award-winning builder, it offers the very best of Winter Park living. Zoned for Audubon K–8 and Winter Park High School, nationally recognized for its International Baccalaureate program, the home is just minutes from Rollins College, downtown Orlando, Park Avenue, and the area's beautiful parks. This exceptional property perfectly captures the timeless lifestyle that makes Winter Park so special.

160 W Rockwood Way, Winter Park

Courtesy of PREMIER SOTHEBY'S INTL. REALTY

$4,950,000
4 Beds ⋅ 7 Baths ⋅ O6414890 MLS
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

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

$3,075,000
5 Beds ⋅ 6 Baths ⋅ O6345085 MLS
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

Courtesy of PREMIER SOTHEBY'S INTL. REALTY

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