Windermere Homes with Deed Restrictions Community Features

Windermere Homes with Deed Restrictions Community Features

Welcome to Windermere, Florida – a picturesque gem nestled in Orange County that perfectly marries small-town charm with modern conveniences. Known for its stunning lakes and lush landscapes, Windermere boasts a vibrant community that is rich in history and culture. With its beautiful tree-lined streets and friendly neighbors, the town offers a serene escape from the hustle and bustle of city life, making it an ideal place for families and individuals alike.

One of the unique features of Windermere is its array of homes within deed-restricted communities. These neighborhoods not only provide a sense of security and exclusivity but also maintain high standards for property upkeep, ensuring that the community remains beautiful and well-preserved. Residents can enjoy amenities such as community parks, walking trails, and recreational facilities, fostering a sense of togetherness and active living.

Windermere is also conveniently located near major highways, making it easy to access nearby attractions like Walt Disney World, Universal Studios, and the vibrant downtown Orlando. With its top-rated schools, diverse dining options, and a variety of shopping experiences, Windermere truly has something for everyone.

Whether you are looking for a cozy family home or a luxurious estate, Windermere's deed-restricted communities offer a safe and inviting environment to call home. Experience the best of Florida living in Windermere, where community spirit thrives and every day feels like a vacation. Come discover your dream home in this idyllic town today!

Newest Windermere Homes with Deed Restrictions Community Features

5 Beds ⋅ 7 Baths ⋅ Bellaria SubDv. ⋅ 34786 Zip Code

BELLARIA ESTATE. Toll Brothers-built Spanish/Mediterranean estate on a 0.76-acre homesite in Bellaria, Windermere's 64-home, 24-hour guard-gated enclave off Lake Butler Road. Built in 2014 and offering 5 bedrooms, 6 baths, 1 office, and 5,667 sq ft across two stories, with block-and-stucco construction, a tile roof, and mature, tree-lined landscaping framing a paver drive and 3-car garage. LIVING SPACES. The plan is designed around everyday living and entertaining alike, with generous formal and casual gathering areas, an open kitchen at the heart of the home, and a first-floor primary suite. Upstairs, the secondary bedrooms and bonus space give family and guests room of their own. OUTDOOR LIVING. Out back, the covered lanai opens to a heated pool and spa with a full summer kitchen, all set against the privacy of the oversized lot, a true year-round Florida outdoor room. LOCATION. Zoned for Windermere Elementary, Bridgewater Middle, and Windermere High, and minutes to Winter Garden Village, Downtown Windermere, Disney, and the 429 for a quick run to the airport or downtown Orlando. Quarterly HOA covers the manned gate, and community park. SHOWINGS. Private showings by appointment. Pre-approval or proof of funds requested prior to scheduling.

13322 Bellaria Circle, Windermere

3 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code

Welcome to your new home! This beautifully maintained, newly listed 3-bedroom, 2-bathroom, third-floor condo is located in the highly desirable Lakeside at Lakes of Windermere community. Offering a perfect blend of comfort, style, and convenience, this move-in-ready home is an exceptional opportunity in one of Central Florida’s most sought-after areas. Step inside to discover a thoughtfully designed interior featuring no carpet throughout, making everyday living and maintenance a breeze. The well-appointed kitchen showcases stainless steel appliances, stone countertops, a stylish backsplash, and abundant cabinet space. Ceiling fans throughout the home, including on the private balcony, add an extra level of comfort and convenience. A washer and dryer are also included. Residents of Lakeside at Lakes of Windermere enjoy an array of resort-style amenities, including a sparkling community pool, spacious fitness center, and beautifully maintained grounds—creating a welcoming environment to relax, entertain, and enjoy the Florida lifestyle. The location is truly hard to beat! Lakeside Village Center is directly across the street, putting everyday conveniences just steps from your front door. Just minutes from Walt Disney World, major highways, highly regarded schools, shopping, dining, and the charming community of Windermere, this condo offers an incredible combination of lifestyle and location. Whether you're searching for a primary residence, vacation home, or investment property, this exceptional condo checks all the boxes. Come see why this Lakeside at Lakes of Windermere gem deserves to be at the top of your list!

8156 Boat Hook Loop Unit 623, Windermere

5 Beds ⋅ 7 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

Expansive golf course and water views abound from this impressive Keene’s Pointe estate residence, located on the 3rd green of the renowned Jack Nicklaus Signature Golf Course. Be welcomed by a grand foyer that flows seamlessly into a formal dining room: a refined, inviting space that blends timeless architectural character with luxury finishes. Framed by exposed wood beams, arched wall details, and wrought iron accents, the room feels warm yet grand. Nearby, the living room offers a more relaxed ambiance that elevates everyday living while providing a sophisticated backdrop for entertaining. An expansive primary bedroom and bathroom suite, office, and pool bath are located off the foyer. The chef’s kitchen feature stainless steel appliances—including a double oven and built in refrigerator—that create a seamless, upscale workflow, while the adjacent breakfast nook provides a sunlit place to enjoy morning coffee. A secondary suite on the first floor is perfect for visiting guests. Three upstairs bedroom suites share a common space for homework or socializing and a large bonus room with bar and balcony is a favorite place to entertain friends. A designated home theater is perfect for relaxing while enjoying favorite shows. Outside is a summer kitchen, fireplace, and lounge area for enjoying the Florida weather. The large resort-style pool and spa with waterfall complete the setting. Home is located across the street from the golf course driving range. Residents of Keene’s Pointe enjoy a sought-after country club lifestyle, with optional membership to the Golden Bear Club offering championship golf, tennis, dining, and a vibrant social calendar—making this one of Central Florida’s most desirable places to call home.

8142 Tibet Butler Drive, Windermere

4 Beds ⋅ 3 Baths ⋅ Lakes/Windermere Ph 02a SubDv. ⋅ 34786 Zip Code

WATER-VIEW SETTING + NIGHTLY MAGIC KINGDOM FIREWORKS + PRIME WINDERMERE LOCATION! Welcome to 12909 Cragside Lane, a beautifully renovated 4-bedroom, 2.5-bath, 2,460-square-foot single-story home in Lakes of Windermere. Located directly across from a neighborhood pond and fountain, the home offers a uniquely Central Florida setting with nightly views of the Magic Kingdom fireworks just steps from your front door. The exceptional location also provides convenient access to highly regarded public and private schools, childcare, Horizon West amenities and Walt Disney World. This move-in-ready home has been extensively updated, with many of the major expenses of homeownership already completed. Improvements include a new roof, HVAC system, water heater, Resideo smart WiFi thermostat, interior and exterior paint, hard-surface flooring throughout with no carpet, light fixtures and ceiling fans — all in 2021; new refrigerator, range/oven, dishwasher, washer and dryer, backyard fencing, paver outdoor-living area and gazebo in 2023; new kitchen countertops and guest-bath flooring, countertop, sinks and faucets in 2025; and refreshed front and rear landscaping and AT&T Fiber wiring in 2026. The fencing, paver improvements, gazebo and landscaping were reviewed and approved through the community HOA architectural-review process. Inside, the bright and spacious floor plan features an open kitchen and family room along with additional flexible living spaces ideal for a home office, recreation, entertaining or additional gathering space. Crown molding, architectural details and updated finishes complement the extensive mechanical and cosmetic improvements throughout. The fenced backyard provides an inviting extension of the living space with its paver patio, gazebo and refreshed landscaping, while the covered front porch faces toward the peaceful pond and fountain setting. Lakes of Windermere offers a community pool, parks, playgrounds, tennis and basketball courts, sidewalks and recreational spaces. The location is especially convenient to Sunset Park Elementary, Horizon West Middle School and Windermere High School, with Windermere Preparatory School also nearby, along with multiple daycare and early-learning options approximately a mile from the home. Shopping, dining and recreation throughout Horizon West are close at hand, while Walt Disney World and Magic Kingdom are just minutes away. With its water-view setting, nightly Disney fireworks, extensive renovations, newer roof and major systems, hard-surface flooring throughout, upgraded outdoor living spaces, excellent school access, fiber connectivity and highly convenient Windermere location, 12909 Cragside Lane offers an exceptional combination of lifestyle, location and move-in-ready condition.

12909 Cragside Lane, Windermere

5 Beds ⋅ 5 Baths ⋅ Windermere Trls Ph 5b SubDv. ⋅ 34786 Zip Code

Set against a natural preserve, this Windermere home combines a flexible floor plan, thoughtful upgrades, and a backyard setting that feels removed from the everyday. Natural light fills the main living spaces, while distinctive ceiling beams in the dining room add warmth and character. A full bedroom and bathroom on the first floor provide flexible space for guests, extended stays, a private office, or everyday living. Upstairs, the spacious primary suite features two custom walk-in closets designed for exceptional storage and organization. Paid-off solar panels provide added energy efficiency without an additional solar payment, while fresh front landscaping enhances the home’s curb appeal. Step outside to a backyard framed by preserve views, local wildlife, and an added sense of privacy. The home’s mid-street position also creates a more tucked-away setting from the neighborhood entrances. Conveniently located in the Windermere and Horizon West area, the home offers easy access to shopping, dining, major roadways, and Walt Disney World. It brings together comfortable living, useful spaces, energy-conscious features, and a natural backdrop that is increasingly difficult to find.

9155 Outlook Rock Trail, Windermere

3 Beds ⋅ 3 Baths ⋅ Summerport Edens Hammock SubDv. ⋅ 34786 Zip Code

Virtually Staged. There is something truly special about coming home to Summerport and this move-in-ready townhome captures that feeling perfectly. From the moment you arrive, the inviting front porch offers a peaceful spot to sit back and watch the sunset over Ancilla Pond. Inside, the functional main level features a highly desirable first-floor primary suite. The bright kitchen connects seamlessly to a private, fenced patio area. Upstairs, you will find an additional bedroom, a versatile loft area, and a secondary bedroom featuring a charming alcove that makes a wonderful home office or study nook. Out back, enjoy ultimate privacy with an attached garage accessed by a rear road and extended driveway. Because the property backs up to the tranquil marshland of Walsh Pond there are no rear neighbors and you are also just steps from the community playground! Summerport features resort-style amenities, including scenic walking paths, small lakes, a clubhouse pool, a fitness center, a fishing dock, volleyball, and a sand beach area right next to the tennis and basketball courts. Unbeatable Location & Convenience: * Top-Rated Schools: Just a short drive to Keene’s Crossing Elementary, Bridgewater Middle and Windermere High School. Elite private options like Windermere Preparatory School and Foundation Academy are also nearby. * Moments from Disney World and all major theme parks. * Easy Commute: Quick access to SR-429, SR-408, and the Florida Turnpike makes driving a breeze. * Shopping & Dining: Minutes from local restaurants, grocery stores, and the popular Winter Garden Village. Low-Maintenance Living, the HOA fully maintains the exterior including the lawn, exterior painting and roof replacements (new roof installed in 2022), allowing for a truly easy lifestyle. Schedule your showing today!

14077 Ancilla Boulevard, Windermere

5 Beds ⋅ 7 Baths ⋅ Lake Cawood Ests Rep SubDv. ⋅ 34786 Zip Code

5 Bed 6 bath custom built home in gated community, 1.02 acre lot with private well for all water supply, NO water or sewer bill. Private Basketball court, overside Pool and Spa, Outdoor Kitchen hookup, granite Counter tops, built in double stainless-steel Oven, built in range. Master Bedroom 1st floor. This house also contains 2 suites, 1 on 1st Floor and another located at the 2nd floor with large screen enclosed balcony leading to the bonus room above the garage. 2nd floor also contain 2 open view lofts and theatre room. New roof in June 2023. Great location with easy access to Hwy 429, 408 and Florida Turnpike, with Schools, Supermarket, and Shopping Centers nearby. This property is also available for rent. Call today to schedule a viewing.

13503 Lake Cawood Drive, Windermere

5 Beds ⋅ 5 Baths ⋅ Lake Davis Reserve A & B SubDv. ⋅ 34786 Zip Code

A rare opportunity to own one of just 18 custom estate homes in this exclusive Windermere enclave of Lake Davis Reserve. Set on more than half an acre, this impressive five-bedroom residence spans over 4,600 square feet, offering a remarkable sense of privacy and seclusion while remaining right in the heart of Windermere. From the moment you enter through the custom iron doors, the craftsmanship and attention to detail are unmistakable. Expansive living spaces, beautiful wood-look porcelain flooring, custom millwork and thoughtfully designed lighting create a home that feels luxurious yet exceptionally comfortable. Custom-designed fireplaces throughout the home provide striking focal points and give each living space its own sense of character and warmth. The chef's kitchen features abundant cabinetry, generous counter space, a large prep island, granite countertops, water softener and a vented cooktop, all opening seamlessly to the main living areas. The spacious primary suite is conveniently located on the first floor and offers a true private retreat, complete with its own custom fireplace, oversized walk-in shower and soaking tub. Additional generously sized bedrooms ensure everyone enjoys ample space, while upstairs, a large flex room with custom built-in cabinetry provides an ideal setting for entertaining, relaxing or movie nights. A dedicated gym adds even more versatility to the floor plan. Outside, the home's sense of privacy becomes even more apparent. A covered lanai, with wiring for remote-controlled screens, opens to a secluded backyard retreat framed by mature tropical landscaping. Completed in 2022, the heated saltwater pool features a PebbleTec finish, multicolor LED lighting, dual sun shelves and an illuminated pergola waterfall. An extended pool deck, outdoor audio, summer kitchen with natural gas, exterior bathroom and app-controlled pool and landscape lighting create an exceptional environment for entertaining or simply enjoying the Florida lifestyle in complete comfort. As evening approaches, the west-facing backyard provides beautiful sunset views in front of your patio gas fireplace. That feeling of seclusion is what makes Lake Davis Reserve so special. Despite its peaceful, private setting, the home sits in the heart of Windermere, with Windermere Preparatory School, Windermere High School and zoning for Windermere Elementary all close by. Disney, SR-429 and premier shopping and dining are just minutes away. Opportunities to purchase in Lake Davis Reserve are exceedingly rare, with only 18 custom estate homes behind its gates. Beautiful in photographs and even better in person, this is a home that simply needs to be experienced. The privacy, scale, custom finishes and atmosphere are difficult to fully capture in photographs. If your buyers are looking for luxury, security and seclusion without sacrificing the convenience of Windermere living, 5526 Marleon Drive deserves to be at the top of their viewing list.

5526 Marleon Drive, Windermere

5 Beds ⋅ 4 Baths ⋅ Royal Estates SubDv. ⋅ 34786 Zip Code

Welcome to this beautifully appointed corner-unit townhome in the highly sought-after area of Windermere, Florida! Ideally located just 15 minutes from Walt Disney World, Hamlin Town Center, and an incredible selection of shopping, dining, entertainment, and everyday conveniences, this home offers the perfect combination of comfort, location, and lifestyle. As a desirable corner unit, the home provides added privacy and an abundance of natural light throughout. Featuring 5 bedrooms and 3.5 bathrooms, this spacious townhome offers a thoughtfully designed open-concept floor plan perfect for both everyday living and entertaining. The first floor includes a dedicated office, ideal for working from home, along with generous living and dining spaces that flow seamlessly into the kitchen. One of the home's standout features is the beautiful in-law suite, complete with its own private entrance, providing an ideal space for extended family, guests, or additional flexibility. Upstairs, the spacious primary suite offers a peaceful retreat along with a versatile loft area that can be used as a secondary living space, playroom, media area, or home gym. With three additional bedrooms upstairs, there is plenty of room for everyone. A two-car garage provides ample parking and storage, while the home's prime Windermere location puts you close to everything Central Florida has to offer. Whether you're looking for a primary residence, multigenerational living, or a fantastic investment opportunity, this townhome is a must-see!

9021 Via Di Canti, Windermere

3 Beds ⋅ 2 Baths ⋅ Summerport Ph 05 SubDv. ⋅ 34786 Zip Code

Don’t miss the opportunity to make this beautiful home in the highly sought-after Summerport community your own! Known for its A-rated schools, picturesque surroundings, and outstanding amenities. This well-maintained 3-bedroom, 2-bath home features a versatile office/den, offering flexible space to accommodate a home office, or guest room. The home features vinyl flooring throughout with no carpet, providing a clean, stylish, and low-maintenance living environment. The kitchen is equipped with a natural gas stove, perfect for those who enjoy cooking with gas. Recent improvements include a newer roof, newer A/C system, and freshly painted exterior, offering added comfort and peace of mind. From the moment you enter the welcoming foyer, you’ll appreciate the bright and open floor plan. Two secondary bedrooms are conveniently located toward the front of the home, providing separation and privacy from the primary suite. Continue down the hallway to the spacious formal living room and flexible additional living space, perfect for adapting to your family’s needs. The private primary suite offers a relaxing retreat with a walk-in closet, dressing area, and ensuite bathroom featuring dual sinks and a spacious standing glass shower. The kitchen seamlessly connects to the bright family and dining areas, creating an inviting space filled with natural light and perfect for everyday living and entertaining. The natural gas stove adds an extra touch of convenience for the home chef. Sliding glass doors open to the covered porch, extending the living space outdoors and overlooking the spacious backyard—an ideal setting for relaxing, entertaining, or enjoying the Florida lifestyle. Summerport offers an impressive array of resort-style amenities, including a community pool, fitness center, parks, playgrounds, fishing pier, and scenic walking trails. The community’s desirable location provides easy access to Windermere, Winter Garden, and Clermont, with an abundance of shopping, dining, entertainment, recreation, and highly rated schools nearby. Commuters will appreciate the convenient access to major roadways, including Highway 429, the Florida Turnpike, SR 408 (East-West Expressway), and I-4, making it easy to travel throughout Central Florida. Walt Disney World and many of Orlando’s world-renowned attractions are also just a short drive away. For Disney enthusiasts, enjoy the added bonus of being just minutes from Walt Disney World, with the opportunity to catch the nightly fireworks from select areas within the community. With vinyl flooring throughout and no carpet, a natural gas stove, a newer roof, newer A/C, freshly painted exterior, flexible living spaces, spacious backyard, desirable location, and exceptional community amenities, this home offers an outstanding opportunity in Summerport. Schedule your private showing today and come see all this home has to offer!

4844 Flint Road, Windermere

3 Beds ⋅ 3 Baths ⋅ Lakes Of Windermere Lake Reams Townhomes Phase 3 SubDv. ⋅ 34786 Zip Code

Beautiful end-unit townhome in Windermere featuring the larger floor plan in the Lake Reams Townhomes community. This well-maintained 3-bedroom, 2.5-bath home offers plenty of natural light and a spacious open-concept kitchen, dining, and living area combo. The kitchen features granite countertops, tiled travertine back splash 46" wood cabinetry, and ceramic tile flooring, with kitchen and laundry appliances included. Upstairs, feel the new plush padded carpeting in the bedrooms, hallway and stairs. The spacious primary suite includes dual vanities, quartz counter top, a large walk-in closet, and walk-in shower. The guest bathroom also has a tub and shower, a single sink with a quartz counter top. Outside, enjoy a private Vinyl fenced in courtyard leading to an oversized rear-entry 2-car garage. The HOA provides low-maintenance living and includes exterior and roof maintenance, landscaping, exterior pest control, and access to the community’s Junior Olympic-size pool. Located approximately 5 minutes from Walt Disney World’s Magic Kingdom, with the added fun of being able to hear and see the Magic Kingdom fireworks each evening. Convenient to Lakeside Village, Horizon West, Winter Garden Village, shopping, dining, major roadways, and highly rated local schools. A great opportunity to enjoy a spacious Windermere townhome in an incredibly convenient location.

8641 Brookvale Drive, Windermere

3 Beds ⋅ 3 Baths ⋅ Ashlin Park Ph 2 SubDv. ⋅ 34786 Zip Code

Get ready to move into one of the best homes and areas right now! Located in the thriving, serene, and highly sought-out Windermere, this dream home is one of a kind! One would never believe it, but this home is an end-unit turnkey luxury town home! Just being able to see the stunning fireworks from Disney from your beautiful home is a dream come true! The schools in Windermere are all outstanding as well, be grateful for the fact that you are living in a tranquil area with some of the best schools in Florida! Filled with several upgrades such as siding all over the garage, a summer kitchen completely fenced with vinyl fence, a filter for the water system throughout the whole house, and this is only for outside the house! This is a dream home through and through! Now entering the newly painted dream home, one will notice the wide-open floor plan with ceramic tile throughout the first floor. The kitchen has granite countertops with splash backs and stainless-steel appliances while being surrounded by several windows, take in the natural light as you cook and enjoy some great meals. Having a separate laundry room as well as a half bathroom on the first floor, enjoy the peacefulness the home brings! Going upstairs to the second floor, see the three bedrooms and two bathrooms! Both bathrooms have granite countertops as well! The master bedroom has a walk-in closet and lots of room! Don’t let this opportunity pass by, a luxurious home located in an excellent area could be yours today!

11734 Water Run Alley, Windermere

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