5 Beds ⋅ 6 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

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

$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

$3,075,000

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

Start Your Search

Orange County › Winter Park › Forest Hills

Forest Hills, Winter Park

Forest Hills is a neighborhood in south Winter Park, in the 32789 zip code, built mostly in the 2010s. Homes are block and stucco. Most homes fall between about 2,300 and 5,800 square feet under air, the median lot is roughly a third of an acre, and a two car garage is standard.

Most of Forest Hills carries no mandatory HOA.

Lake Chelton Park, Bonnie Burn Park and KEYA ACADEMY sit inside the subdivision.

What the homes are

Built Mostly built in the 2010s, with homes from 1925 to 2026.
Construction Block and stucco. Shingle roofs are near universal.
Style Mediterranean, Traditional, Contemporary. Predominantly two story.
Size Most homes fall between about 2,300 and 5,800 square feet under air.
Bedrooms Four bedrooms is the most common plan, then five.
Garage A two car garage is standard.
Lot The median lot is roughly a third of an acre.
HOA Most of the neighborhood carries no mandatory HOA. Confirm on a specific parcel before relying on it.

Where Forest Hills is

Forest Hills, centered at 28.580017, -81.349415. Drag to explore.

Street level, inside the neighborhood. Drag to look around.

Drive times below are measured on the road network from the center of Forest Hills, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving to	Time	Miles
Downtown Orlando	18 min	4.9
Walt Disney World	33 min	25.4
Orlando International Airport	30 min	13.0
Universal Orlando	26 min	13.4

Public schools nearby

Audubon Park Elementary School 5 min, 1.2 mi
Baldwin Park Elementary School 6 min, 1.9 mi
Park Maitland School of Winter Park 8 min, 1.8 mi
Winter Park High School 9 min, 2.7 mi

Private schools nearby

Baldwin Oaks Academy 3 min, 1.0 mi
KEYA ACADEMY 4 min, 1.0 mi
Halo ABA Academy 7 min, 1.7 mi

Parks and recreation

Lake Chelton Park 1 min, 0.2 mi
Bonnie Burn Park 2 min, 0.5 mi
Beeman Park 6 min, 1.6 mi
Blue Jacket Park 3 min, 0.8 mi

Groceries and errands

Greater Lifestyle Foods 7 min, 1.3 mi
Publix Super Market at Hollieanna Shopping Center 8 min, 1.6 mi
Wild Fork Meat & Seafood Market, Winter Park 8 min, 1.6 mi
The Ancient Olive Gourmet of Winter Park 11 min, 2.0 mi

Useful local links

Nearest is not the same as zoned. The schools above are the closest ones to Forest Hills by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Orange County Public Schools before it matters to a decision.

Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Forest Hills actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 6 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated September 2026.

Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.

What homes sold for in Forest Hills

$3,175,000Median sale price

$736Median per square foot

62 daysMedian days to contract

6Homes sold in 12 months

Sale prices ran from $1,350,000 to $3,600,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

By size

Home size	Sales	Median price	Median $/sq ft	Median days
3,000 sq ft and up	6	$3,175,000	$736	62 days

Larger homes usually show a lower price per square foot. That is normal and it is why a price per foot taken from the whole neighborhood should never be applied straight to one house.

Homes priced right sold far faster

Median days to go under contract. Shorter is better.

Never reduced 2 sales, closed at 95.6% of asking10 days

Reduced at least once 4 sales, closed at 94.4% of the reduced price102 days

Sellers who priced correctly and held their number went under contract in a median 10 days. Sellers who had to reduce took 102 days and still closed at 94.4% of their already reduced price, after a typical cut of $90,000. Opening high costs time and money, in that order.

How buyers paid

Cash 4 sales67%

Conventional 2 sales33%

Cash was 67% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.

Questions about a specific home in Forest Hills, or want to know what yours would sell for?
Call or text Brenden Rendo at 407-616-9019 or send a message.

About this data. Source is the Stellar MLS feed for Forest Hills in Winter Park, Orange County, covering closed sales from 25 September 2025 through 20 September 2026, refreshed monthly and current as of September 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.