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8168 Boat Hook Loop Unit 707, Windermere
$290,000
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
Back On The Market! Like New Home! Welcome to this Move-In Ready condo in the Desirable Town of Windermere! Located across the street from Lakeside Village, you'll enjoy easy access to grocery stores, shops, and dining options. 15 Minute Drive to Disney and short distance to Universal Studios, Epic, Sea World, and Discovery Cove, this location offers unparalleled convenience. ORIGINAL OWNER and Gently Lived In, Like a New Condo! This charming condo is nestled in a community with the BEST POOL in town, making every day feel like a resort stay. Inside, you'll find BRAND NEW LUXURY VINYL FLOORING in the spacious open floor plan. The Primary Bedroom is tucked away on one side for privacy, with the additional bedrooms on the opposite side. The Oversized Walk-In Closet off the Primary Suite provides ample storage space. The galley kitchen is a chef’s dream, featuring 42-inch cabinets with extra drawer space, stainless steel appliances, and granite countertops—perfect for preparing your favorite meals. Additionally, the condo is equipped with a newer A/C and WATER HEATER for added peace of mind. Meticulously maintained by the original owner, this home has been lovingly cared for. Relax and unwind on the screened-in lanai, perfect for sipping your morning coffee or enjoying a peaceful evening. Outdoor enthusiasts will love the abundance of activities available, including walking around the pond, strolling down the dock to the lake, biking, playing volleyball or tennis, and enjoying the pool with friends. Stay fit with the fitness center, or play billiards in the clubhouse. The community also hosts regular events for added enjoyment. With an onsite management company, 24-hour security, and concierge trash pick up, you can experience stress-free living and peace of mind. Don’t miss out—call today to schedule your private viewing of this amazing home!

8168 Boat Hook Loop Unit 707, Windermere

105 Pine Street, Windermere
$2,285,000
5 Beds ⋅ 6 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code
One or more photo(s) has been virtually staged. On a serene over half acre lot in the heart of historic downtown Windermere this fabulous one-of-a kind multi-generational home is a short distance from the charming boutiques, eateries, coffee shops, local wine shop, brewery, the weekly farmers market, food trucks and Windermere Library. The main home was meticulously expanded and redesigned in 2023. The casita was built new in 2024. The fabulous ADA-accessible casita with its own private entrance is 1,246 square feet, ideal for hosting friends, family or aging parents. This casita boasts a generously sized great room with plastered Kiva fireplace and built-in bookcases, large kitchen with plastered hood vent, custom tile, porcelain concrete countertops, honed marble island top, coffee station, Café Matte white/brushed bronze refrigerator, 30-inch double oven with six-burner gas cooktop, soft close custom cabinets and drawers, 39-inch iron door, custom stonework walls and floating shelves. The spacious bedroom has a walk-in custom closet & en-suite bath with dual vanities, marble countertops and edgeless walk-in shower. Additional amenities include yellow pine wood ceiling beams, hickory wood flooring, 11½-inch baseboards, solid knotty alder wood doors, custom reclaimed pine closet barn door, and 10-12-foot vaulted ceilings. The main home features four spacious bedrooms, 4.5 baths, a large laundry room, theater-game room and office with 4,450 square feet. The spacious great room has a cozy fireplace, decorative wood beam ceiling and opens to the gourmet kitchen. This kitchen is a chef’s dream featuring stainless steel appliances including Bosch double ovens, Viking gas cooktop, walk-in pantry, Cambria countertops, farmhouse sink, custom cabinetry and oversized island with breakfast bar. The spacious owner’s suite with pool views has two walk-in custom closets and spa-like bath with a freestanding solid stone soaking tub, separate oversized walk-in shower and dual solid stone sinks designed with luxury and relaxation in mind. The large theater-game room has sliding glass doors leading to the covered lanai and private fenced yard. You will enjoy entertaining outside with your sparkling, heated saltwater pool with spa and summer kitchen. A large three-car RV garage joins the casita to the main home. This garage with soaring ceiling has room for two car lifts and RV parking with a 50-amp plug, epoxy flooring and storage racks. This home was thoughtfully designed with optimal storage and custom finishes. Amenities and renovations include new roof, exterior paint, gutters, LVP flooring, custom built-in closets, aluminum fenced yard, pool-spa, two Generac generators, security cameras, termite bond, three tankless water heaters, irrigation well, 10-12-foot ceilings throughout and custom closets in all rooms to keep you organized. Residents of the Town of Windermere enjoy exclusive access to the town’s private boat ramp, giving access to the Butler Chain of Lakes as well as the town’s private pickleball/tennis courts. Golf carts are welcome in this charming town. No HOA restrictions. Location is a short commute to top-rated schools, major highways, upscale shopping, Orlando’s renowned attractions and world-class golf courses.

105 Pine Street, Windermere

13463 Bonica Way, Windermere
$1,778,500
5 Beds ⋅ 6 Baths ⋅ Tildens Grove Ph 02 SubDv. ⋅ 34786 Zip Code
Luxury Living in Tilden’s Grove – Stunning 5-Bedroom Mediterranean Style Estate in Windermere, FL Welcome to this exquisite 5-bedroom, 5.5-bathroom estate nestled in the highly sought-after 24 hr guard gated community of Tilden’s Grove in Windermere, Florida. This beautifully updated residence offers an unparalleled blend of elegance, modern upgrades, and resort-style living. Step inside to discover brand-new cabinetry throughout the home, adding a fresh and modern touch to every space. The chef’s kitchen is a dream, featuring a spacious bar and wine cellar, perfect for entertaining guests. The living room boasts a brand-new Anderson window, flooding the space with natural light and offering serene views of the lush surroundings. On the second floor, a spacious bonus room with newly built-in wardrobes provides flexible living space, ideal for a media room, home office, or additional guest suite. The beautifully renovated laundry room adds both style and functionality to daily living. Designed for year-round enjoyment, the heated salt water pool and spa is a true retreat, complemented by a brand-new screen enclosure for ultimate privacy and comfort. The home also features new HVAC units, ensuring energy efficiency and modern climate control. Located in the charming Tilden’s Grove community, this home offers luxury, privacy, and convenience in one of Windermere’s most desirable neighborhoods. Don’t miss the opportunity to make this exceptional property yours! Schedule your private showing today!

13463 Bonica Way, Windermere

7736 Brofield Avenue, Windermere
$549,000
3 Beds ⋅ 2 Baths ⋅ Lake Sawyer South Ph 04 SubDv. ⋅ 34786 Zip Code
Welcome to your private tropical paradise, backing onto protected conservation land with no rear neighbors! This immaculate, energy-efficient home, built in 2012, features a custom heated saltwater pool & oversized Jacuzzi, perfect for relaxation or entertaining. Recent pool upgrades include a new pool heater (2023), new pump (2024), and resealed drains (2024). The travertine deck, oversized screened-in patio, and lush tropical landscaping create a serene resort-like retreat. Step inside to discover the beautiful engineered hardwood flooring, triple high sliders leading to the covered travertine-paved patio, and double-pane windows for energy efficiency. The chef’s kitchen boasts stainless steel appliances, granite countertops, and cherry wood cabinetry with crown molding. The elegance continues in the primary suite, featuring custom built-in cabinets and a spacious walk-in closet. Recent home improvements include a brand-new HVAC system (2024) and a new water heater (2023) for peace of mind. Located in the highly desirable Enclave at Berkshire Park, this community offers open green spaces, walking/biking trails, a pool, playground, tennis and basketball courts, and dog care stations—all meticulously maintained. Enjoy low HOA fees, excellent Wi-Fi for remote work, and top-rated schools. Situated on a quiet, no-drive-through circle, you can watch Disney fireworks from your front porch nightly! Just 10 minutes to Disney, 5 minutes to Publix and dining, and 10 minutes to Winter Garden Village shopping, this home is perfect for families looking to embrace the relaxed Florida lifestyle. Don't miss out on this peaceful, poolside paradise—schedule your showing today!

7736 Brofield Avenue, Windermere

14143 Ancilla Boulevard, Windermere
$410,000
4 Beds ⋅ 3 Baths ⋅ Edens Hammock SubDv. ⋅ 34786 Zip Code
Nestled in the heart of Windermere’s desirable Summerport community, 14143 Ancilla Blvd offers a peaceful retreat surrounded by lush greenery, shimmering lakes, and serene conservation views. This charming corner-unit townhome is perfectly positioned to enjoy the best of Florida living, with scenic walking trails, a nearby playground, and open green spaces just steps away. Inside, the home features a thoughtfully designed layout with spacious interiors bathed in natural light. The open-concept living and dining areas flow seamlessly into a modern kitchen with ample storage and sleek finishes, creating an inviting space for entertaining or everyday living. The main-floor master suite provides a private sanctuary with a walk-in closet and en-suite bathroom, while the second floor boasts three additional bedrooms and a versatile loft area. Outside, the private patio offers the perfect spot to relax and take in the tranquil surroundings. With its proximity to top-rated schools, shopping, dining, and world-class attractions like Disney, this home combines convenience with a serene lifestyle. Whether you’re enjoying morning coffee on the patio or exploring the community’s amenities—including a pool, sports courts, and playgrounds—this property is designed for both comfort and connection to nature. Don’t miss your chance to make this stunning home yours—schedule your private tour today!

14143 Ancilla Boulevard, Windermere

407 W 1st Avenue, Windermere
$2,625,000
6 Beds ⋅ 6 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Exceptional lakefront opportunity on the BUTLER CHAIN of Lakes! Nestled on the pristine shores of Wauseon Bay, this rare lakefront property offers an unparalleled opportunity to create the ultimate luxury retreat on the coveted Butler Chain. Set on a pristine, oversized lot (~1.26 acres) in one of the area’s most sought-after locations, this FENCED property offers a rare opportunity to create your dream home. This solid BLOCK home boasts breathtaking WATER views, a grand, tree-lined driveway with private GATE, and a setting that exudes elegance and privacy. While the residence itself could use some updating, the setting is nothing short of spectacular offering a picturesque backdrop, mature landscaping, and a premier location that enhances both value and vision. Featuring a spacious layout with soaring ceilings and panoramic lake views, this home is ready to be transformed into a masterpiece. The prime waterfront location offers direct access to the Butler Chain known for renowned boating, fishing, and water sports, making it an ideal sanctuary for lake lovers. Whether you envision a modern showpiece or a timeless estate, this property presents the perfect canvas to bring your vision to life. The home features 6 bedrooms, 5.5 baths (4 en-suite baths), a 3-car garage, 14 X 60 SALTWATER and heated pool/spa with screen-enclosure, two fireplaces (natural gas), a dock for your watercraft along with a floating swim dock, and a sitting area by the water that’s perfect for a cozy night by the fire. Upstairs you’ll find the primary suite along with 3 other bedrooms and 3 en-suite baths. The PRIMARY suite faces the water and features a fireplace, dual sinks, a garden tub, separate shower, and two walk-in closets. The downstairs area includes two additional rooms, 1.5 baths, a formal dining area, living area, a sitting area with a wood burning fireplace overlooking the pool and lake, as well as a bar, which is perfect for entertaining your guests. The kitchen is spacious in size and includes STAINLESS appliances. UPDATES: 5 ton AC 2023, 3.5 ton AC 2016, PebbleTec pool finish 2015, upstairs gas fireplace 2016, tankless water heater 2016, septic field (front of home) 2016. The Butler Chain of Lakes is one of Central Florida’s most prestigious and sought-after freshwater lake systems, located in Windermere and Southwest Orlando. This chain consists of 13 interconnected lakes, known for their crystal-clear waters, sandy bottoms, and exceptional boating, fishing, and waterfront living. Enjoy a rare combination of luxury, recreation, and natural beauty, all while being just minutes from Disney, golf courses, upscale shopping, fine dining, and top-rated schools. Windermere is a GOLF CART friendly community where you’ll find a brewery, coffee shop, dining, a Farmer’s Market, tennis courts, parks, a boat ramp, and more. Opportunities like this are rare, don’t miss the chance to transform this hidden gem into a one-of-a-kind lakefront estate!

407 W 1st Avenue, Windermere

9501 Hempel Cove Boulevard, Windermere
$1,325,000
4 Beds ⋅ 5 Baths ⋅ Lake Down Cove SubDv. ⋅ 34786 Zip Code
Original owners, first time on the market and meticulously maintained! Located on a quiet cul-de-sac you will find a generous 1.14-acre lot with mature trees providing ample shade for this Georgia brick faced two-story home. A flexible floorplan as well as a lovely outdoor oasis is perfect for entertaining family and guests. The home offers 4,789’ square feet of living space, features high ceilings on both floors, double crown moulding, four bedrooms, three full bathrooms, two half baths and a large media room to enjoy theater style movies. As you enter the open foyer with 21’ ceilings and a curved wooden staircase, you will find to the right a formal living room, and to the left, a formal dining room. Moving on to the heart of the home you find the kitchen, a dining area and family room all open to each other, creating a perfect space for entertaining with a stunning view overlooking the large paver lanai, open pool and expansive backyard. The Thermador Appliance Suite makes the kitchen a chef’s dream, the suite includes: a dual-fuel range with six burners and a griddle, two ovens, wood paneled refrigerator and freezer columns, and drawer microwave. You will appreciate having two islands, a walk-in pantry for extra storage and the custom Shuler cabinetry with quartz countertops to complete the look. The formal living and family room feature premium Berber carpet with waterproofing installed. The laundry room is located off of the kitchen with easy access to the main garage and a spacious oversized workshop ideal for woodworking, golf simulator, work out room or preferred hobbies. As you ascend the curved staircase you will find the four bedrooms and a separate living area. Enter the spacious primary bedroom with fireplace and primary ensuite bathroom offering his and hers custom closets, separate vanities, and a shower that’s a breeze to clean. Two additional upstairs bedrooms share a Jack-and-Jill bath with separate private vanities, while the fourth bedroom is an ensuite. Finishing off the upstairs is the living space with custom cabinets that could easily be converted to a fifth bedroom. Outside, the pool area is surrounded by a paver deck perfect for entertaining friends and family. There is an easily accessible designated pool bathroom and an outdoor shower. This home blends comfort and functionality, offering everything you need for easy living and outdoor enjoyment and entertainment.

9501 Hempel Cove Boulevard, Windermere

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34786 Windermere FL Homes for Sale

34786 At a Glance

The 34786 zip code covers Windermere, an upscale town in Southwest Orange County, Florida, on the Butler Chain of Lakes.
Communities: Isleworth, Keene's Pointe, the historic Town of Windermere, Windermere Downs, Lake Butler Sound, and Reserve at Lake Butler Sound.
Schools (zoning is address-specific, so confirm via OCPS Find My School): Olympia High and Windermere High; Gotha Middle and Bridgewater Middle; and Windermere Elementary.
Lifestyle & landmarks: the Butler Chain of Lakes, Isleworth and Keene's Pointe golf, and the historic Town of Windermere's brick streets and Friday market.
Access: Conroy-Windermere Road, Apopka-Vineland Road (CR 535), Winter Garden- Vineland Road, and SR 429.

34786 Zip Code Homes For Sale By Price Range

Browse Windermere Properties by Price Category
Property Type Price Range Bedrooms Area
34786 Condos & Townhomes Under $600,000 2-3 34786 Windermere, FL
34786 Single-Family Homes $600,000-$1,000,000 3-4 34786 Windermere, FL
34786 Move-Up & Gated Homes $1,000,000-$2,500,000 4-5 34786 Windermere, FL
34786 Lakefront & Isleworth Estates Over $2,500,000 5-8+ 34786 Windermere, FL

34786 Market Data

Current market conditions for Windermere's 34786 zip code, calculated from Orange County MLS data. Sale price and days on market cover homes that closed in July 2026; active listings is a current count.

Active Listings
236
Median Sale Price
$839,500
Homes Sold (July)
70
Average Days on Market
54

Windermere 34786 Community Highlights

Butler Chain of Lakes

A dozen connected spring-fed lakes prized for water-skiing, boating, and some of Central Florida's finest lakefront estates.

Isleworth & Keene's Pointe

Guard-gated golf communities with championship courses, home to executives and athletes.

Historic Town of Windermere

The small incorporated town keeps its canopy oaks, unpaved sand-brick streets, and a popular Friday farmers market.

Top-Rated Schools

Zoned mainly to Olympia and Windermere High, Gotha and Bridgewater Middle, and Windermere Elementary (zoning is address-specific).

Luxury & Estates

Gated estates and custom lakefront homes range well into the multimillions, among the highest-value in Orange County.

Prime Location

Minutes from Dr. Phillips' Restaurant Row, Disney, and SR 429 for the whole metro.

Frequently Asked Questions About 34786 Windermere

Where is the 34786 zip code?

34786 is Windermere, an upscale town in Southwest Orange County, FL, on the Butler Chain of Lakes between Dr. Phillips, Winter Garden, and Walt Disney World, about 20 minutes from downtown Orlando.

What schools serve the 34786 zip code?

Because 34786 spans several OCPS attendance zones, the assigned schools depend on the exact address. Use the OCPS Find My School locator to confirm. The area is zoned mainly to Olympia and Windermere High; Gotha and Bridgewater Middle; and Windermere Elementary.

What is Isleworth?

Isleworth is a guard-gated luxury golf community in 34786 on the Butler Chain of Lakes, known for championship golf and multimillion-dollar estates owned by executives and athletes.

Is there lakefront real estate in 34786?

Yes. Windermere is built around the Butler Chain of Lakes, with some of Central Florida's most sought-after lakefront estates in Isleworth, Keene's Pointe, and Lake Butler Sound.

Why is Windermere so desirable?

Windermere combines the Butler Chain of Lakes, guard-gated golf communities, a historic small-town core, top-rated schools, and a prime location near Dr. Phillips and Disney.

How far is 34786 from Walt Disney World?

Windermere 34786 is roughly 15 minutes from Walt Disney World via Winter Garden-Vineland Road and SR 429.

Explore Nearby Zip Codes

32836 Lake Buena Vista

Disney-adjacent gated and lakefront communities, southeast of Windermere

32819 Dr. Phillips

Upscale Dr. Phillips and Bay Hill, east of Windermere

34787 Winter Garden

Historic downtown and Horizon West new communities, northwest of Windermere

34734 Gotha

Small historic community with large lots, north of Windermere

32835 Orlando

The master-planned MetroWest community, northeast of Windermere

Windermere Homes for Sale

Every active listing in Windermere, not just this zip code

View All Orange County Zip Codes

Complete guide to all Orange County areas

Your 34786 Windermere Real Estate Experts

Brenden Rendo and his team specialize in Windermere 34786. We track the market every week with ORRA and Stellar MLS data, and we know the gated and lakefront communities: Isleworth, Keene's Pointe, the Butler Chain, and the historic Town of Windermere. Buyers get help with lakefront and gated-community due diligence, luxury and estate analysis, and school zoning; sellers get pricing built on a real comparative market analysis, not a Zillow Zestimate.

Prefer to talk? Call (407) 616-9019, contact our team, or register for free market reports.