Windsor Hill Real Estate

Windsor Hill Real Estate

Welcome to Windsor Hill, a picturesque subdivision nestled in the heart of Windermere, Florida, within the vibrant Orange County. This charming community is the epitome of suburban living, offering residents a serene environment surrounded by lush landscapes and tranquil waters. Windsor Hill is designed for those who appreciate the finer things in life, combining elegance with comfort.

As you drive through the tree-lined streets of Windsor Hill, you will be greeted by beautifully crafted homes that showcase a variety of architectural styles. Each residence is thoughtfully designed, featuring spacious layouts, modern amenities, and inviting outdoor spaces perfect for entertaining or enjoying a peaceful evening under the stars. The community fosters a strong sense of camaraderie, making it easy to forge lasting friendships with neighbors.

Windsor Hill is not just about beautiful homes; it’s also about a lifestyle. Residents have access to a range of amenities, including serene walking trails, sparkling lakes, and well-maintained parks, perfect for family outings or leisurely strolls. The community is conveniently located near top-rated schools, shopping centers, and dining options, ensuring that everything you need is just a stone's throw away.

Moreover, Windermere's charm extends beyond Windsor Hill. With its rich history and picturesque surroundings, residents can enjoy a variety of recreational activities, from boating on the nearby lakes to exploring local boutiques and cafes.

Experience the perfect blend of tranquility and convenience at Windsor Hill, where your dream home awaits in one of Florida's most desirable communities. Come discover the lifestyle you've always envisioned!

Newest Listings in Windsor Hill

9615 Windy Ridge Road, Windermere
$5,300,000
6 Beds ⋅ 7 Baths ⋅ O6449197 MLS
A palm-framed pool and spa, a balcony-connected game room and a dedicated theater give this Mediterranean-inspired estate a distinctive rhythm of outdoor relaxation and evenings at home. Set on 2.5 fully fenced acres with a private gated entrance, the residence welcomes you along a fountain-centered circular drive to 12-foot iron cathedral-style doors. Inside, marble flooring with decorative inlays flows through most first-floor living areas, while soaring ceilings and a two-story mitered glass window frame views toward the pool and covered terrace. A grand two-story marble staircase rises from the formal living room to an iron-railed interior balcony, with an elevator providing additional access between floors. Beneath coffered ceilings, the kitchen’s curved breakfast bar creates a gathering spot connected to the family room, where an entertainment center and sliding glass wall doors lead to a covered poolside terrace with a fireplace. An elaborately decorated vaulted ceiling gives the formal dining room its own character, complemented by a wine cellar with capacity for 500 bottles. Six oversized bedroom suites include two primary suites and a 19' × 25' suite configured as an executive office with a full bathroom. Decorative ceilings continue through the bedroom spaces, while an elaborate bathroom pairs separate vanities with a tub and walk-in shower. A separate study and mirrored 20-foot fitness studio provide spaces for work and exercise, while a 29' × 29' theater with reclining lounge chairs and tiered seating platforms gives movie nights their own dedicated setting. Upstairs, the 41-foot billiards, game and media room combines a refreshment bar with space for game tables and a pool table, opening through sliding glass walls to a covered stone balcony overlooking the grounds. The 45-foot pool’s shallow beach-style landing, raised spa and expansive terrace invite afternoons outdoors, with broad lawns and a sand volleyball area extending the recreation. Four oversized garages and abundant storage add practical space, while the acreage offers potential to expand the residence or build a detached guesthouse, subject to applicable approvals. Approximately 15 minutes from restaurants, hotels, shopping, Universal Studios and Disney attractions, this estate brings distinctive architecture and varied recreation together for an inviting experience at home.

9615 Windy Ridge Road, Windermere

9548 Crown Prince Lane, Windermere
$1,395,000
4 Beds ⋅ 4 Baths ⋅ O6407352 MLS
Virtually Staged. Nestled on a rare half-acre lot in one of Windermere’s most sought-after communities, Windsor Hills, this FULLY RENOVATED luxury home delivers the ultimate move-in-ready, like-new lifestyle buyers are searching for. Featuring 4 spacious bedrooms, 4 beautifully updated bathrooms, and a highly desirable open-concept layout, every inch of this residence has been meticulously redesigned with today’s modern buyer in mind. The stunning chef’s kitchen is a true showpiece, appointed with brand-new premium Thermador appliances, custom cabinetry, designer finishes, and elegant lighting that elevate the entire living experience. Wide-plank luxury vinyl flooring flows seamlessly throughout the home, combining sophistication with durability and low-maintenance living. Designed for both everyday comfort and entertaining, the flexible floor plan includes an oversized upstairs BONUS ROOM, with a built-in-closet and a full bathroom, ideal for a home theater, game room, executive office, fitness studio, or private guest retreat/in-law suite. Major upgrades provide exceptional value and peace of mind, including a 2021 roof, dual high-efficiency HVAC systems (2 units/ 2026), new water heater, upgraded sliding glass doors, and an epoxy-coated garage. The expansive backyard offers endless possibilities to create your dream outdoor oasis, resort-style pool, or entertaining space. Located just minutes from the renowned Butler Chain of Lakes, championship golf courses, upscale dining, shopping, and top-rated schools, this exceptional property combines luxury, privacy, and convenience in one of Central Florida’s most desirable locations. Rarely does a fully updated home with this level of quality, land, and location become available. Some photos have been virtually staged. Furnishings shown are for illustrative purposes only and are not included in the sale.

9548 Crown Prince Lane, Windermere

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