Windermere Homes with Sidewalks Community Features

Windermere Homes with Sidewalks Community Features

Welcome to Windermere, Florida—a picturesque town nestled in the heart of Orange County, known for its stunning lakes, lush landscapes, and an inviting community atmosphere. Just a stone’s throw from the bustling city of Orlando, Windermere offers the perfect blend of serene suburban living and convenient access to urban amenities. With its charming streets lined with majestic oak trees and vibrant gardens, it’s no wonder that this area is a sought-after destination for families and professionals alike.

One of the standout features of Windermere is its commitment to community living, exemplified by the abundance of homes with sidewalks. These pedestrian-friendly pathways create a welcoming environment for residents to stroll, jog, or bike through the neighborhood while enjoying the fresh air and beautiful surroundings. Imagine taking an evening walk with your family, greeting friendly neighbors, or enjoying a leisurely bike ride to one of the local parks. The sidewalks not only enhance the aesthetic appeal of the area but also foster a sense of community and connection among residents.

Windermere is also home to a variety of recreational activities, including nearby golf courses, lakes for boating and fishing, and scenic parks perfect for picnics and outdoor gatherings. With top-rated schools, boutique shops, and delightful dining options, this charming town truly has something for everyone. Experience the warmth and vibrancy of Windermere, where community spirit thrives and every day feels like a vacation. Come discover your dream home in this enchanting locale and embrace the lifestyle you’ve always wanted!

Newest Windermere Homes with Sidewalks Community Features

$3,999,000
5 Beds ⋅ 6 Baths ⋅ O6445244 MLS
Keene’s Pointe – 24-hour gated/attended community in Windermere, Florida. Experience refined luxury in this exceptional golf-front estate perfectly positioned along the 17th fairway of The Golden Bear Club. Fully renovated, architecturally refined and intentionally designed by Ashley Martin Home. From the moment you enter, an inviting foyer opens to a spacious living room framed by 12-foot ceilings, expansive windows, and views of the course, filling the home with natural light and warmth, as well as a functional dining room with built-in cabinetry, perfect for entertaining. Designed with both elegance and functionality in mind, the home features wide-plank hardwood flooring throughout, custom drapery and shades, and extensive upgraded lighting and finishes. The private office is a standout, complete with rich built-in cabinetry and a wood-accent ceiling that creates a sophisticated workspace. The primary suite is a true retreat, accessed through a private vestibule-style entrance offering a serene escape. Inside, enjoy access to the outdoors, a spa-inspired bath with a freestanding tub, an oversized walk-in shower, and a spacious custom walk-in closet with built-ins. The chef’s kitchen is thoughtfully appointed with built-in refrigeration and dishwasher, an appliance garage, a large center island, Butler’s pantry with wine refrigeration, and a generous breakfast nook. A mud area with built-ins adds everyday convenience, while the family room showcases custom built-ins for effortless living. The home offers a versatile and spacious layout, including two ensuite bedrooms with walk-in closets on the main level, and two additional bedrooms upstairs connected by a shared bath. The second floor also features a loft with built-ins that can easily function as a fifth bedroom, playroom or media room, along with a bonus space overlooking the golf course—currently used as a gym, but ideal for a game room or lounge. Outdoor living is equally impressive, featuring a saltwater pool and spa, fire pit, cabana with summer kitchen, and a private putting green. The fenced yard and retractable screened lanai create a seamless indoor-outdoor experience, while a convenient exterior-access half bath serves the pool area. Additional highlights include a well-appointed laundry room with stacked washer and dryer, and a four-car garage with high ceilings and custom flooring, and much more! This turn-key home can be purchased fully furnished and decorated. Conveniently located to shopping, dining, expressways, tourist attractions, and top-rated public and private schools, this is a rare opportunity to own a meticulously designed, luxury estate that blends comfort, style, location, and stunning golf course views into one extraordinary residence.

6120 Greatwater Drive, Windermere
$2,350,000
4 Beds ⋅ 6 Baths ⋅ O6444548 MLS
SINGLE STORY LIVING and PRIVATE PEDESTRIAN-GATED ACCESS to WINDERMERE PREPARATORY SCHOOL from within the community distinguish this custom Waterstone home. Built in 2014 and located behind a staffed, guard-gated entrance, the residence offers approximately 4,169 square feet, four bedrooms, four full baths, two half baths, and a three-car garage. Two stately palms welcome you to the beautifully landscaped 0.44-acre homesite, while landscape lighting highlights the grounds after sunset. From the moment you enter, the view opens to the CENTRAL COURTYARD, SALTWATER POOL, and SPA. Direct access from the kitchen, family room, and primary suite makes the courtyard part of daily life. Covered lanais, generous lounging areas, a summer kitchen with a full-size motorized screen, and an outdoor fireplace provide space to gather and dine outdoors. The courtyard has been freshly painted, and the travertine pavers were recently sealed. Inside, soaring ceilings, tray details, crown molding, and expansive windows bring light and courtyard views into the living spaces. The kitchen features Wolf and Sub-Zero appliances, rich wood cabinetry, dual islands, bar seating, and a concealed walk-in pantry. The spacious primary suite includes hardwood flooring, a sitting area, two expansive custom walk-in closets, and a bath with a soaking tub, oversized rainfall shower, and generous vanity space. An adjoining flex room can serve as a home office, gym, or private retreat. Additional features include two newer air-conditioning units serving the multizone HVAC system, a sound system throughout the indoor and outdoor living areas, a whole-house Lorex camera system, a porte-cochère, and an expansive paver driveway. Waterstone is near Windermere High School, with convenient access to Winter Garden Village, Lakeside Village, Walt Disney World, and major Orlando routes. Schedule a private showing to experience this distinctive Windermere courtyard home.

11532 Waterstone Loop Drive, Windermere
$1,488,000
4 Beds ⋅ 4 Baths ⋅ O6440411 MLS
Welcome to 12721 Jacob Grace Court, an exceptional residence nestled within the highly sought-after gated enclave of Tildens Grove in Windermere. Ideally positioned on a quiet cul-de-sac, this remarkable property sits on over a half-acre homesite with serene conservation and pond views, offering a rare combination of privacy, space, and natural beauty. From the moment you enter, you are greeted by an inviting floor plan filled with abundant natural light and elegant finishes throughout. Just past the two-story foyer, executive home office and formal living room, the expansive main living areas are thoughtfully designed to flow seamlessly, creating the perfect setting for both everyday living and sophisticated entertaining. The heart of the home is the beautifully renovated kitchen, featuring generous cabinetry, quality appliances, and ample counter space, all overlooking the main living and dining areas with stunning private views. The primary suite serves as a tranquil retreat, complete with a spa-inspired bath and spacious walk-in closet. Additional second floor bedrooms provide balcony access and flexibility for family, while a first-floor bedroom and bonus room offer an ideal layout for a private guest sanctuary. Step outside and discover one of the home’s most captivating features—a sprawling backyard with a two-story screen enclosure that is anchored by a resort-style pool, spa and expansive entertaining areas set against conservation and water views. Residents of Tildens Grove enjoy a premier lifestyle with gated access, tree-lined streets, tennis courts, playground and proximity to top-rated schools, boutique shopping, dining, golf, and all the attractions that make Windermere one of Central Florida’s most desirable locations.

12721 Jacob Grace Court, Windermere
$405,000
4 Beds ⋅ 3 Baths ⋅ O6444644 MLS ⋅ 14350 BLDG.
Come be wow'd by this 4/2.5 bedroom water view townhome that faces Bluebird Pond and garden area from front porch with primary bedroom on main level. Primary bedroom has views of and access to an additional private back porch. Primary bath offers stand alone shower, generous walk in closet and granite counters. Three secondary bedrooms upstairs with views of Bluebird Pond also have access to separate loft space as additional living room, playroom, game room, study, den or library. Any chef would enjoy cooking in this kitchen with views of and access to private back porch, generous granite counter space, large pantry, stainless steel appliances with new microwave and tall cabinets. Half bath downstairs has been remodeled and is just off the living room and kitchen area. Laminate wood floors throughout downstairs and crown molding in the living and dining areas. Entire interior, including ceilings, has been freshly painted. Brand new carpet in upstairs rooms. Roof is 2022, A/C is 2026, Hot water heater is 2026 as well. Two car garage with covered access to home and amble driveway space plus additional guest parking in front of home. From the photos you will see you are walking distance (less than .3 miles) to Foxtail Coffee, Marcos Pizza, Kelly's Ice Cream, the dog park, children's playground, and Keene's Crossing Elementary School. The community offers (also within walking distance) community pool, tennis and pickleball courts, fitness centers, clubhouse, and many miles of walking trails. You simply can't beat this location, zoned A rated schools, and 15 min to Disney theme parks, easy access to major thoroughfares, international airport, fine dining, entertainment, etc.

14350 Bridgewater Crossings Boulevard, Windermere
$540,000
4 Beds ⋅ 2 Baths ⋅ S5158063 MLS
This 4-bedroom, 2-bath pool home in the gated community of Eden Isle offers approximately 2,020 square feet of single-story living with an open floor plan, high ceilings, and plenty of space for both everyday living and entertaining. Step outside and enjoy your own private Florida retreat featuring a screened-in pool and a fully fenced backyard; ideal for relaxing, entertaining, or enjoying the Florida sunshine. The spacious primary suite features an en-suite bathroom with a soaking tub, separate shower, double vanity, and plenty of room to unwind. Major improvements provide added peace of mind, including a roof replaced in 2022, HVAC system replaced in 2021, and a new hot water heater. Eden Isle residents enjoy access to a community playground and private community boat ramp on Lake Speer, making it easy to enjoy the Florida lifestyle both on and off the water. Conveniently located in sought-after Windermere with easy access to shopping, dining, entertainment, major roadways, and Central Florida's world-famous attractions. Schedule your private showing today!

13738 Eden Isle Boulevard, Windermere
$1,598,000
4 Beds ⋅ 4 Baths ⋅ O6443650 MLS
Set on 0.54 acre at the end of a quiet cul-de-sac in the Reserve at Lake Butler Sound, 6533 Cartmel Lane offers single-story living within one of Windermere’s established guard-gated communities. Mature landscaping, a paver driveway and a substantial architectural entry frame the residence, while the private pool opens to an expansive backyard that gives the property a notable sense of space and privacy. Inside, high ceilings and generous natural light shape a thoughtfully arranged split-bedroom floor plan. The primary suite is positioned apart from the secondary bedrooms, creating a more private retreat within the home. Just beyond the bedroom, a bonus room offers a flexible extension of the suite, suited to a sitting room, study or quiet reading space. The principal living areas are distinct yet connected, allowing the home to feel open without sacrificing definition. Generous windows bring natural light throughout, while the formal dining area and multiple gathering spaces create an easy progression from one room to the next. Outdoor living is centered around the screened lanai and pool, both overlooking the broad rear lawn. The scale of the homesite gives the exterior a sense of openness, while the three-car garage provides additional parking and storage. A tile roof completes the home’s architectural profile. Reserve at Lake Butler Sound was conceived as a gated residential community of luxury homes, shaped by consistent architectural and landscape standards intended to preserve a cohesive and harmonious setting. Controlled access established landscaping and a carefully maintained residential environment contribute to a sense of privacy, permanence and distinction. Approximately six minutes away, downtown Windermere offers a refined small-town setting defined by tree-lined streets, local parks, neighborhood dining and the popular Friday farmers' market. Just beyond the community, a public boat ramp provides access to Lake Butler and the interconnected Butler Chain of Lakes, while several of Central Florida’s notable golf courses are within easy reach. Walt Disney World, Universal Orlando, Sand Lake Road, downtown Orlando and Orlando International Airport are approximately 20 to 30 minutes away. With its single-story design, generous homesite and setting within one of Windermere’s established luxury communities, 6533 Cartmel Lane offers a refined expression of Central Florida living, defined by privacy, space and convenient access to the area’s lakes, golf, entertainment and travel connections.

6533 Cartmel Lane, Windermere
$586,542
3 Beds ⋅ 3 Baths ⋅ TB8551016 MLS ⋅ 3 BLDG.
Under Construction. Enjoy convenient, low-maintenance living in this two-story townhome featuring a private paver courtyard and two-car garage, perfectly located in the heart of Windermere. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. This Cawood floor plan features interior finishes from the AW Collection Coastal, blending clean lines and neutral tones and textures. Design upgrades include 42" cabinets, quartz countertops, tiled backsplash, pendant lighting and stainless steel appliances. Ideally situated, you’re just 30 minutes from Orlando International Airport and 15 minutes from world-famous Disney theme parks. The community is also zoned for great schools and is minutes from downtown Winter Garden, where charming streets, local history, shopping, dining, and community events create a vibrant lifestyle. Residents will also enjoy a community pool and playground area. With its prime location and practical design, this townhome delivers the perfect blend of convenience, comfort, and Central Florida living. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

13317 Lush Lime Alley, Windermere
$2,995,000
6 Beds ⋅ 9 Baths ⋅ O6434168 MLS
Set on nearly an acre within the prestigious guard-gated community of Bellaria, this remarkable estate combines grand-scale living, exceptional flexibility, and an unbeatable location. Impressive curb appeal creates an immediate sense of arrival, enhanced by a spacious U-shaped driveway and an oversized three-car garage. Beyond the entry, a dramatic formal living room welcomes you with soaring two-story ceilings, abundant natural light, and an elegant bar area complete with a wine refrigerator. The expansive kitchen serves as the heart of the home, featuring a massive center island, extensive cabinetry, generous prep space, and a full suite of stainless steel appliances. A formal dining room provides a refined backdrop for special occasions, while the adjoining breakfast nook offers a relaxed setting for everyday meals. The sprawling first-floor primary suite is a private retreat with impressive proportions and separate his-and-hers walk-in closets. Its spacious bathroom features dual vanities, an oversized walk-in shower, and a soaking tub designed for relaxation. An additional guest suite on the main level provides comfort and privacy for visitors, while a dedicated formal office creates an ideal space for working from home. Upstairs, five additional bedrooms provide tremendous flexibility for family and guests. A spacious loft offers another casual gathering area, while the separate bonus room could easily be transformed into a private home theater, game room, fitness studio, or additional entertainment space. With six bedrooms, multiple living areas, and thoughtfully designed spaces throughout, the home is exceptionally well suited for both everyday living and large-scale entertaining. Outside, an expansive covered patio extends the living space and features a full summer kitchen, making it ideal for dining, entertaining, and enjoying Florida’s year-round sunshine. The enormous backyard offers remarkable possibilities, with ample room to create a custom resort-style pool. Bellaria’s prime location places you just minutes from Winter Garden Village, charming Downtown Windermere, Restaurant Row, world-renowned theme parks, and an outstanding selection of shopping, dining, and entertainment. Offering extraordinary space, privacy, and potential in one of Windermere’s most sought-after gated communities, this impressive estate presents a rare opportunity to create the ultimate luxury lifestyle.

13101 Bellaria Circle, Windermere
$369,000
3 Beds ⋅ 3 Baths ⋅ O6348704 MLS ⋅ Venetta Way BLDG.
Virtually Staged. Welcome home to this beautifully refreshed 3-bedroom, 2.5-bath end-unit townhome in one of Windermere’s most sought-after communities. Offering the added privacy of an end-unit location, a peaceful conservation backdrop, and a private courtyard, this home delivers the perfect blend of comfort, convenience, and easy Florida living. Freshly painted throughout with brand-new carpet, the home feels bright, clean, and move-in ready from the moment you walk through the door. The inviting layout is filled with natural light and offers plenty of space to relax, entertain, and enjoy everyday life. All three bedrooms are located upstairs, including a spacious primary suite featuring a walk-in closet, dual-sink vanity, and upgraded frameless-glass walk-in shower. Step outside to your private courtyard—a versatile outdoor space perfect for morning coffee, weekend gatherings, or unwinding at the end of the day. Beyond the courtyard, the rear of the home overlooks a conservation area, creating a peaceful natural setting with no immediate rear neighbors. It’s a rare combination of privacy and convenience. And there’s more to look forward to—a new roof is coming soon, adding another layer of value and peace of mind for the next owner. Ideally located near A-rated schools, parks, shopping, dining, and everyday conveniences, this Windermere townhome puts you close to everything while giving you a private place to call home. Come see why this one is worth making your next move!

12934 Vennetta Way, Windermere
$489,900
3 Beds ⋅ 2 Baths ⋅ S5157827 MLS
Welcome to 13535 Bramham Lane, a spacious and airy 3-bedroom, 2-bath, single-story home offering plenty of room to spread out and make it your own. Freshly painted throughout, the home features tile flooring in the main living areas with carpeting in the bedrooms. The versatile floor plan includes living and dining areas along with a spacious great room, providing multiple spaces for entertaining, relaxing, and everyday living. The kitchen features granite countertops and stainless steel appliances and opens to the great room, creating a comfortable gathering space at the heart of the home. Outside, nicely landscaped grounds create a welcoming first impression, while the charming front porch is perfect for morning coffee or enjoying the Florida weather. A back patio provides additional outdoor living space for grilling, entertaining, or simply relaxing. Complete with a two-car garage, this home offers a wonderful combination of space, comfort, and flexibility. Located within a gated community featuring sidewalks throughout, residents can enjoy a neighborhood setting designed for walking and outdoor living, along with a community pool. It's so close to Disney that you can hear the train whistle!

13535 Bramham Lane, Windermere
$649,000
4 Beds ⋅ 4 Baths ⋅ O6442193 MLS
Welcome to your beautiful corner lot home in the sought after Berkshire Park community of Windermere! Don’t miss the opportunity to own this thoughtfully designed 4 bedroom, 3.5-bath home with a bonus room and 3-car garage, offering an ideal blend of space, comfort, and functionality. Major updates include a new roof installed in 2022 and a new AC system installed in 2025, providing added peace of mind for the next owner. A brick-paver driveway and charming walkway welcome you to the inviting front porch, perfectly positioned along a quiet, tree-lined street. Step inside to a spacious foyer featuring soaring ceilings and an open, airy feel that continues throughout the main living areas. The formal dining room flows seamlessly into the open concept kitchen and family room, creating an ideal space for both everyday living and entertaining. The kitchen features a large center island, granite counters, stainless steel appliances, ample cabinetry, and a dedicated eat-in area, while the family room opens to a screened in patio overlooking the generously sized backyard making a wonderful setting for morning coffee, outdoor dining, or relaxing with family and friends. The main level owner’s suite offers convenience and privacy with dual vanities, tub, shower, and walk in closet. Your well appointed laundry room provides direct access to the spacious three-car garage. Upstairs, a versatile bonus room serves as the perfect media room, playroom, home office, or additional gathering space. Three generously sized bedrooms and two full bathrooms complete the second floor, providing plenty of room for family and guests. Residents of Berkshire Park enjoy community amenities including a beautiful neighborhood pool and playground, all within the highly desirable Windermere area. The close proximity to Disney World, shopping, restaurants, and "A" rated schools make this an unbeatable location. With its spacious floor plan, prime Windermere location, 3-car garage, newer roof, newer AC, and inviting outdoor living space makes this a home you won’t want to miss. Be sure to click on the virtual tours.

13324 Jervey Street, Windermere
$379,900
3 Beds ⋅ 3 Baths ⋅ S5157627 MLS ⋅ 8 BLDG.
LIVE IN OR INVEST WHERE OTHERS DREAM OF VACATIONING!!! Amazing opportunity in Windermere, one of Central Florida’s most desirable locations, just minutes from the magic of Walt Disney World and located in a highly rated school zone! This beautiful 3-bedroom, 2.5-bath townhouse offers the perfect combination of location, comfort, and lifestyle, featuring a spacious and functional layout plus a private fenced backyard, ideal for relaxing, entertaining, and enjoying the Florida lifestyle. Experience a beautiful community surrounded by nature and exceptional amenities, including a community pool, playground, walking trails, scenic lakes, and lush green spaces. Conveniently located near highly rated schools, shopping, dining, major roadways, and Central Florida’s world-famous attractions. Whether you’re looking for your next home or an investment opportunity in one of the Orlando area’s most sought-after locations, this is an opportunity you don’t want to miss!. LIVE IT. INVEST IN IT. LOVE WINDERMERE !!!

8608 Brookvale Drive, Windermere
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