Winter Park Homes with Clubhouse Community Features

Winter Park Homes with Clubhouse Community Features

Welcome to Winter Park, Florida – a picturesque city that effortlessly combines charm, culture, and community spirit. Nestled just north of Orlando, Winter Park is renowned for its stunning tree-lined streets, beautiful parks, and vibrant arts scene. With its rich history and a delightful mix of boutiques, cafes, and galleries, this city offers a unique blend of small-town feel and urban sophistication. Residents enjoy a plethora of outdoor activities, from strolling along the serene shores of Lake Virginia to exploring the scenic trails of the nearby parks.

One of the standout features of Winter Park is its inviting homes with clubhouse community amenities, perfect for those seeking a lifestyle that emphasizes both comfort and connection. These communities are designed to foster a sense of belonging, offering residents access to luxurious clubhouses equipped with state-of-the-art fitness centers, sparkling swimming pools, and versatile gathering spaces for social events. Imagine hosting a barbecue with neighbors or unwinding after a long day in a beautifully landscaped setting.

The homes themselves boast modern designs and spacious layouts, ideal for families or those looking to downsize without sacrificing quality. With a variety of styles and sizes available, you’re sure to find the perfect fit for your lifestyle.

In Winter Park, you’re not just buying a home; you’re investing in a vibrant community where neighbors become friends, and every day feels like a getaway. Discover the charm of Winter Park and experience the exceptional living offered through its clubhouse communities today!

Newest Winter Park Homes with Clubhouse Community Features

$147,000
1 Beds ⋅ 1 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code
Virtually Staged. LOCATION, CONVENIENCE, AND EASY LIVING IN WINTER PARK! This move-in-ready first-floor, 1-bedroom, 1-bath condo features an open living and dining area, wood flooring throughout the main living areas, tile flooring in the primary bedroom, a private screened-in balcony, a fully equipped kitchen, and a stackable washer and dryer. Conveniently located near UCF, Rollins College, Valencia College, Park Avenue, and Downtown Orlando, with easy access to shopping, dining, and major highways. Community amenities include two pools, a tennis court, fitness center, and clubhouse. HOA includes water, trash, internet, pest control, exterior maintenance, and grounds care. A great opportunity to enjoy a low-maintenance lifestyle in a highly convenient Winter Park location.

285 Lewfield Circle Unit 285, Winter Park
$750,000
4 Beds ⋅ 4 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code
Gated Community | Dual Primary Suites | Main-Level Living | Located in Winter Park’s gated Hawks Crest community, this two-story home pairs a spacious open floor plan with a private backyard setting and a layout that offers exceptional versatility. The main level includes the primary suite, dedicated study, laundry room, kitchen, and principal living areas, making day-to-day living possible without the need for stairs. The gourmet kitchen features quartz countertops and 42-inch cabinetry, while 8-foot interior doors add height and proportion throughout. Large sliding glass doors open to an oversized screened and covered patio with eastern exposure, morning sun, and no rear neighbors. Built in 2020, the home also offers the advantages of newer construction, complemented by a tile roof. Upstairs, the 4-bedroom, 3.5-bath floor plan includes three bedrooms, one serving as a second primary suite, along with a large bonus room and separate loft. Hawks Crest is set along Lake Howell and offers a clubhouse, fitness center, community pool, splash pad, parks, walking trails, grilling and picnic areas, and a pier with lake access. Park Avenue, shopping, dining, recreation, and major roadways are all within convenient reach.

1287 Verdant Glade Place, Winter Park
$1,050,000
2 Beds ⋅ 2 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code
Experience effortless Winter Park living in Whispering Waters, a premier 55+ lakefront community beautifully situated along the shores of Lake Osceola and just a short stroll from Park Avenue. Priced below appraised value, this rare third-floor mid-century modern condo offers exceptional value and a truly turnkey lifestyle. Filled with natural light, the thoughtfully designed floor plan features spacious living and dining areas overlooking tranquil waterfall ponds and lush, beautifully maintained grounds. A versatile bonus space provides the perfect setting for a home office, den, or creative retreat. The expansive owners suite is designed for relaxation, featuring a private sitting area, dual closets, direct access to the pool, and a spa-inspired bath complete with a jetted tub. The generously sized secondary bedroom offers a cozy reading nook and dual closets, providing comfort and flexibility for guests. Enjoy effortless, worry-free living with secure underground parking, a deeded parking space, and convenient elevator access. Even better, monthly association dues include electricity, air conditioning, heat, water, sewer, and trash—making everyday living remarkably simple. Step outside your door and enjoy everything that makes Winter Park so special, from the acclaimed shops and restaurants of Park Avenue to Rollins College and Winter Parks historic nine-hole golf course. With its prime lakefront setting, exceptional location, and low-maintenance lifestyle, this is a rare opportunity to own a piece of one of Central Florida’s most desirable communities. Discover the best of Winter Park living at Whispering Waters—schedule your private showing today.

311 E Morse Boulevard Unit 4-5, Winter Park
$189,900
2 Beds ⋅ 2 Baths ⋅ Whisperwood Condo SubDv. ⋅ 32792 Zip Code
This charming 2-bedroom, 1.5-bath condo offers a desirable townhome-style layout with spacious living areas and thoughtful storage throughout. The community features deluxe vinyl fencing installed by the HOA, along with a clubhouse and a community pool, providing great amenities for residents to enjoy. Inside, you’ll find the convenience of an in-unit washer and dryer combo, ample storage under the stairs, and a large carport with an attached storage shed. The spacious primary bedroom opens directly to a generous private balcony—perfect for relaxing or unwinding after a long day. Ideally located just 15 minutes or less from UCF, Rollins College, Valencia East, and Full Sail University, and only 20 minutes from Orlando International Airport. Whether you’re a first-time homebuyer, student, investor, or looking to make your move into Winter Park, this home delivers affordability, convenience, and excellent potential.

7468 Canford Court Unit 24, Winter Park
$770,000
4 Beds ⋅ 3 Baths ⋅ Preserve At Hawks Crest SubDv. ⋅ 32792 Zip Code
Virtually Staged. Welcome to one of the most uniquely positioned homes in the highly sought-after gated community of Hawk’s Crest. This former Meritage model home sits on a premium corner lot just steps from the clubhouse and resort-style amenities, and is one of the few corner homes in the community permitted to have a private fenced backyard. With more than 2,100 square feet of thoughtfully designed, energy-efficient living space, the home showcases an impressive collection of upgrades and finishes selected to highlight the best Hawk’s Crest has to offer. From the moment you enter, high ceilings and an inviting entryway set the tone. As a former model, the home features upgraded interior doors, cabinetry, baseboards, bathroom vanities, and custom details throughout. The expansive kitchen is designed for both everyday living and entertaining, featuring 42-inch cabinetry, granite countertops, double ovens, a walk-in pantry, stainless steel appliances, and a large center island with pendant lighting overlooking the living and dining spaces. The spacious owner’s suite offers a true retreat with an oversized walk-in closet and en-suite bath featuring dual vanities and a walk-in shower. Three additional bedrooms, two full bathrooms, and a generous laundry room with a utility sink and custom built-in drop zone provide plenty of space, storage, and everyday functionality. Outside, the covered lanai opens to a private fenced backyard surrounded by lush landscaping and complete with a fire pit, an ideal setting for entertaining, pets, or simply enjoying the outdoors. Hawk’s Crest residents enjoy an impressive collection of amenities including a resort-style pool, clubhouse, fitness center, splash pad, playgrounds, dog park, virtual guard gate, and access to Lake Howell. Former model home. Rare fenced corner lot. Extensive upgrades. And one of the shortest walks to the clubhouse in the entire community. This is an opportunity that truly stands apart in Hawk’s Crest.

2286 Marsh Sedge Lane, Winter Park
$254,000
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village SubDv. ⋅ 32792 Zip Code
Virtually Staged. LIVE THE WINTER PARK LIFESTYLE! STYLE, SPACE & LOCATION—THIS ONE HAS IT ALL! Welcome to Cedarwood Village, where easy living meets one of Winter Park’s most desirable locations, just minutes from the charm, dining, shopping, and entertainment of Downtown Winter Park and Park Avenue. This beautifully maintained 2-bedroom, 2-bath residence with an enclosed bonus room offers a spacious, light-filled floor plan designed for both comfortable everyday living and entertaining. Vaulted ceilings enhance the open living and dining areas, while the generously sized kitchen features newer appliances, abundant cabinet and counter space, plus room for a cozy breakfast table. Retreat to the oversized primary suite, complete with two large closets and sliding glass doors opening to the bonus room. The renovated primary bath adds a touch of luxury with an updated vanity and impressive custom walk-in shower. The guest bedroom offers its own sliding glass doors leading to the front patio, creating a bright and inviting space for family or overnight guests. The updated guest bath adds convenience with a washer and dryer neatly tucked away in the closet. One of the home's best features is the enclosed bonus room, offering valuable additional living space that's perfect for a home office, den, reading retreat, hobby room, or simply a relaxing place to unwind. Enjoy the Florida lifestyle without leaving the neighborhood! Cedarwood Village offers a sparkling community pool, two tennis courts, and clubhouse for residents to enjoy. And then there’s the LOCATION! Shopping, restaurants, medical facilities, and everyday conveniences are all close by, with easy access to major roadways and the boutiques, sidewalk cafés, restaurants, parks, and unmistakable charm of Park Avenue and Downtown Winter Park just minutes away. More than a home—it’s a Winter Park lifestyle. Come see why Cedarwood Village is such a special place to call home!

2477 Tahoe Circle Unit 2477, Winter Park
$675,000
4 Beds ⋅ 3 Baths ⋅ Meadows At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to a premier opportunity in the the coveted Winter Park. This beautifully maintained 4-bedroom, 2.5-bathroom home is located in The Meadows – an alcove in the gated Hawks Crest community – and offers buyers a turn-key opportunity to crack into the Winter Park market. With 1,770 square feet of thoughtfully designed living space, this home strikes the perfect balance between functionality and flow, featuring a living/dining combination anchored by the kitchen in the heart of the home. The central dining configuration is equally suited for quiet evenings or effortless entertaining, while the living room offers versatility as a spacious indoor retreat, or an indoor-outdoor oasis, complimented by the glass sliders. Before entering the primary suite, find three secondary rooms - two guest bedrooms and an office - along with a full guest bathroom and a powder bath, making every day living hassle-free and providing ample privacy. In the primary en-suite, unwind and enjoy the pleasures of a spacious retreat featuring an over-sized walk-in shower. This home is only 4 years young, so newer appliances and core components provide peace of mind, and an upgraded Tesla level 2 charger makes it fully equipped to suit every homeowner's needs. This home is just a short walk to the community amenities which include a clubhouse, pool, fitness center, turf lawn with a putting green, playground, dog park, and a private community dock on to Lake Howell. The 24-hour gated community provides peace of mind, all within easy reach of A-rated Seminole County schools (Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High), major employment corridors, the Orlando International Airport, and everything that Orlando has to offer. This is the kind of opportunity that doesn't come along often. Contact us to schedule your private tour today!

1122 Wildmeadow Run, Winter Park
$115,000
1 Beds ⋅ 1 Baths ⋅ Golfside Villas Condo SubDv. ⋅ 32792 Zip Code
Virtually Staged. ***Welcome to this exceptionally well-maintained 1-bedroom, 1-bathroom condominium ideally located in Winter Park! Lovingly cared for by its longtime owner, this home offers a wonderful combination of comfort, functionality, and convenience. *WASHER AND DRYER LOCATED IN UNIT* Inside, you'll find a spacious, thoughtfully designed layout featuring a generous living area, an oversized bedroom, and a large bathroom. The charming kitchen offers ample cabinet and counter space, creating an inviting space for both everyday living and entertaining. Step outside to your private balcony, the perfect place to enjoy your morning coffee or relax at the end of the day. The home's separate exterior entrance adds an extra level of convenience and privacy. Enjoy low-maintenance living with HOA dues that cover water, trash, exterior maintenance, and roof replacement. The community recently completed a roof replacement, providing added peace of mind for the new owner. Residents also enjoy access to the community pool, perfect for cooling off on warm Florida days. Conveniently located near UCF, Valencia College, Waterford Lakes Town Center, Orlando International Airport, major highways including SR 408 and SR 417, shopping, dining, and entertainment, this home is also zoned for highly desirable schools. Whether you're a first-time homebuyer, someone looking to downsize, or an investor seeking a well-maintained property in a prime East Orlando location, this condominium offers an outstanding opportunity. Schedule your private showing today!

1000 S Semoran Boulevard Unit 302, Winter Park
$230,000
2 Beds ⋅ 2 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code
ATTENTION ** SELLER OFFERING A $5,000 CREDIT TOWARDS BUYER'S CLOSING COSTS OR INTEREST RATE BUY DOWN!! A GEM! Tucked away in a private, sought after community and so conveniently located in breathtaking Winter Park. Here’s a beautifully maintained, upgraded and move-in ready home. With 2 large bedrooms and 1.5 bathrooms, this unit spans 1,219 square feet, providing an ideal space for cozy living. Enjoy the benefits of a peaceful and friendly community, with well-manicured grounds and a welcoming atmosphere. This charming home has been tastefully updated with upgraded laminate flooring, a renovated kitchen with granite countertops, newer cabinets and a stylish backsplash. The floor plan offers a dining & family room open combination which looks out on the porch and brings in plenty of natural light. Both nicely sized bedroom suites are on the second floor and have a shared & updated bathroom. Ample storage on the back patio for your bike and all your extra toys allowing you to enjoy your weekends. This is an extremely well managed community with an onsite manager taking pride in the community and care for their residents. Four Seasons community provides super amenities including a cubhouse with library, a renovated fitness center, 3 swimming pools, tennis courts, a laundry facility steps away and shuffleboard. Walk to Cady Way Park with tennis courts, baseball and soccer fields, playgrounds, community pool and Cady Way Trail. Minutes to Advent Health Winter Park Hospital, shopping on Park Avenue, Rollins College, Valencia, Full Sail and UCF. This pet friendly community and charming condo has everything you need! Great opportunity to own in FOUR SEASONS condominiums where LOCATION, LOCATION, LOCATION is prime!

200 Saint Andrews Boulevard Unit 2904, Winter Park
$169,900
1 Beds ⋅ 1 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
PRICE ADJUSTMENT! Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping! One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional Built-in Closets, Vanity and Mirrored Closets and updated Bath, accessible for Guests and close to Master! Updated Windows! Private Balcony! Owner is providing a One-Year Home Warranty and a $3,000 Flooring Credit. Make this affordable Unit your own!

1500 Gay Road Unit 4D, Winter Park
$729,995
4 Beds ⋅ 3 Baths ⋅ Landings At Hawks Crest SubDv. ⋅ 32792 Zip Code
Nestled within the gated community of Hawks Crest, this meticulously maintained two-story residence showcases over $70,000 in luxurious builder upgrades, blending timeless design, modern comfort, and effortless Florida Living. This stunning home presents an exceptional opportunity to enjoy one of Winter Park's most desirable lifestyle communities. A welcoming entry opens to light-filled interiors where soaring ceilings, elegant finishes and a thoughtfully designed open-concept floor plan create a seamless flow throughout the home. Luxurious white ceramic tile spans the entire first floor, enhancing the home's bright and airy feel while providing both beauty and durability. The gourmet kitchen serves as the centerpiece of the home, featuring upgraded cabinetry, quartz countertops, stainless steel appliances, abundant storage and an expansive peninsula with bar seating. Spacious living areas and generously sized bedrooms provide comfort and flexibility for a variety of lifestyles. Upstairs, plush carpeting creates a warm and inviting retreat, while the primary suite offers a private sanctuary complete with a large walk-in closet and a spa-inspired bath. Additional bedrooms provide ample space for family, guests, a home office or a fitness room. Sliding glass doors extend the living space to a covered lanai, creating an inviting setting for outdoor dining, morning coffee or relaxed evenings enjoying Florida's year-round climate. Residents of Hawks Crest enjoy an exceptional collection of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, playgrounds, dog park, scenic trails and private access to Lake Howell. The community is also conveniently located near local favorites, including Kelly's Ice Cream, Foxtail Coffee and Park Maitland Preschool. Ideally situated just minutes from Park Avenue, downtown Maitland, major highways, and top-rated schools, this exceptional home offers effortless access to Central Florida's finest shopping, dining and cultural attractions. Despite its convenient location, the community maintains a sense of privacy and tranquility.

1418 Lone Feather Trail, Winter Park
$310,000
2 Beds ⋅ 2 Baths ⋅ Aloma Park SubDv. ⋅ 32792 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 5781 Shale Court in Winter Park, a 2-bedroom, 2-bath home designed for comfortable everyday living. This one-story residence offers a practical layout with space for relaxing, dining, and hosting guests. The two-bedroom configuration provides flexibility for residents, visitors, a home office, or a hobby room, while two full bathrooms add convenience for daily routines. Outdoor living includes a covered and screened patio, creating a comfortable space to enjoy fresh air, outdoor dining, or quiet downtime while staying shaded and protected from the elements. Located in Winter Park, the home is close to shopping, dining, parks, schools, and everyday conveniences. The area offers access to nearby destinations such as Winter Park Village, Park Avenue, local recreation, and major roadways connecting to Maitland, Orlando, and surrounding Central Florida communities.

5781 Shale Court, Winter Park
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