Winter Park Homes with Awning(s) Exterior Features

Winter Park Homes with Awning(s) Exterior Features

Welcome to Winter Park, Florida—a picturesque city nestled in Orange County that perfectly blends small-town charm with urban sophistication. Renowned for its stunning lakes, lush parks, and vibrant cultural scene, Winter Park is a haven for those seeking a serene lifestyle without sacrificing convenience. Just a short drive from downtown Orlando, this enchanting city boasts an array of boutique shops, gourmet dining, and world-class art galleries, making it a vibrant community for residents and visitors alike.

One of the standout features of homes in Winter Park is their unique architectural style, with many properties showcasing delightful awnings that enhance both aesthetic appeal and functionality. These charming exterior features not only add character to the homes but also provide shade and protection from the Florida sun, creating inviting outdoor spaces for relaxation and entertainment. Imagine sipping your morning coffee under a beautifully designed awning, or hosting friends for an evening barbecue in your backyard, all while enjoying the gentle breeze and warm sunshine that Winter Park is known for.

With a diverse selection of homes available—from historic bungalows to modern masterpieces—there’s something to suit every taste and lifestyle. Whether you’re drawn to the tree-lined streets of the historic district or the contemporary developments near the lakes, Winter Park offers a welcoming community that feels like home.

Explore the possibilities of living in this enchanting city, where every day feels like a vacation, and your dream home awaits under the inviting embrace of a charming awning. Welcome to Winter Park, where life is beautiful, and community is everything!

Newest Winter Park Homes with Awning(s) Exterior Features

4 Beds ⋅ 3 Baths ⋅ Quail Run SubDv. ⋅ 32792 Zip Code

Welcome home to this beautifully maintained 4-bedroom, 3-bath pool home, tucked away at the end of a quiet cul-de-sac in Winter Park's Quail Run! From the moment you step inside, vaulted ceilings and abundant natural light create a bright, open, and inviting atmosphere. Fresh interior paint and 5-inch baseboards add a crisp, polished finish throughout. Designed with both everyday living and entertaining in mind, the home offers formal living and dining rooms along with an upgraded kitchen that opens seamlessly to the large family room. The kitchen features granite countertops, stainless steel appliances, a built-in pantry, and an expansive breakfast bar perfect for casual dining and gathering with family and friends. The primary suite offers a relaxing retreat, complete with a stylish barn door leading into the spacious bath that features his-and-hers wardrobes, dual vanities, a large custom built-in storage closet, soaking tub, walk-in shower, and private water closet. Bedroom closets throughout the home are equipped with storage systems for added organization. The renovated pool bath provides convenient direct access to the outdoor living area. An interior laundry room offers additional cabinet storage, and the washer and dryer convey. Step outside and discover an incredible amount of versatile living and entertaining space. The HUGE Florida room is fully paved and features vinyl sliding windows plus its own mini-split system, allowing you to enjoy the space comfortably in a variety of seasons. Beyond it, the fully paved patio leads to a beautiful newer pool surrounded by travertine, lush landscaping, and a tranquil water feature. An additional outdoor paved entertaining pad/pergola combination overlooks the expansive, fully sodded and fenced backyard, creating a peaceful setting for relaxing, hosting, or enjoying Florida living year-round. The property also offers exceptional parking and storage flexibility with an additional paved parking area beside the driveway as well as another paved pad tucked behind the white PVC privacy fence. Additional features include an irrigation system supplied by a well, and an architecural shingle roof, complete with gutters and downspouts. With its spacious layout, impressive outdoor living areas, beautiful pool, abundant natural light, and peaceful cul-de-sac setting, this Winter Park home offers the perfect combination of comfort, functionality, and Florida lifestyle!

4599 Whimbrel Place, Winter Park

3 Beds ⋅ 3 Baths ⋅ Vilasa Twnhms SubDv. ⋅ 32789 Zip Code

Enjoy luxury living and premium sought-after location at Vilasa Homes, the newest construction in Winter Park, FL 32789. Walk to Park Avenue lifestyle, arts and culture- a mini-version of Manhattan’s Central Park, brick streets, historic neighborhoods, area’s hottest restaurants, shopping and the prestigious Rollins College. The finishes for this 2-estory townhome personally selected by one of the nation’s top interior designers. Carefully selected design team of Nasrallah Architectural Group, Ted Maines Interiors and Jordan Builders. Alys Beach inspired incorporating wood accents, architectural stairway, wrought iron and two-story ALL block construction all steps away from downtown Winter Park. Energy-saving features such as Pella double pane windows and extra insulation. Home is prewired for surround sound, cameras, alarm system, etc. Beautifully appointed-engineered wood flooring throughout from Daltile/Mohawk, recessed lights, level 4 wall finishes, 13-foot ceilings on the main floor, and 10-foot ceilings upstairs. This unit has been thoughtfully upgraded with a top modern package worth $40k. Chef’s gourmet kitchen is complete with high-end 18” flat panel cabinetry, 2.5” mitered Quartz countertops, double waterfall Quartz island, Thermador appliances, and beautiful Quartz backsplash. 6 burner Thermador SS gas cooktop, built-in butlers bar in dining room, staircase lighting are all additional upgrades. Spacious primary retreat on second floor with loft area perfect for office, Peloton or game room all wired with internet and electrical. Primary bedroom includes two separate his and hers closets with custom shelving and organizers. Generous closet and storage spaces. Relax in your garden tub and oversized walk-in shower, Quartz countertops, designer tile, Koehler fixtures/bathroom accessories and custom lighting treatments. Two more stately suites that can be used for exercise, office or bedrooms. Automated, remote window coverings. 2-car garages featuring insulated steel garage doors and additional storage. The Swoope townhomes each have an enlarged backyard measuring approx. 40ft x 20ft, including 8ft x 8ft covered patio slab which extends from the sliding doors. Each unit includes privacy fencing and landscaping. Owners maintain own backyard. Convenient and minutes from Hillstones, Whole Foods, Trader Joe's, Park Avenue restaurants and shopping! Top rated-9 hole Winter Park Golf Course, Casa Feliz, Morse Museum, water sports, Rollins, and churches are all a short stroll away.

504 W Swoope Avenue, Winter Park

4 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 01 SubDv. ⋅ 32792 Zip Code

Welcome to turnkey Winter Park living! This beautifully maintained 4-bedroom + office, 2,092 SF pool home features brand-new living room flooring, a roof only 4 years old, newer A/C, NO HOA, and a private in-ground pool. Step inside to a bright, open-concept layout with abundant natural light, granite countertops, modern appliances, generous cabinet space, and a cozy wood-burning fireplace. The spacious primary suite offers pool views, while the oversized enclosed Florida room/lanai creates the perfect setting for entertaining and year-round indoor/outdoor living. Outside, enjoy a fully fenced and landscaped backyard, private pool, irrigation system, attached 2-car garage, and additional parking. Vacant and move-in ready—bring your furniture and start enjoying the Florida lifestyle! Ideally located in the desirable Winter Woods/Lake Howell area, with convenient access to SR-417, I-4, SR-436, Howell Branch Road, Downtown Orlando, Winter Park shopping and dining, UCF, Orlando International Airport, parks, golf courses, and highly regarded Seminole County schools. Pool. No HOA. Major updates. Prime Winter Park location. Move-in ready. This home delivers the space, lifestyle, and convenience today’s buyers are looking for.

2217 Sussex Road, Winter Park

4 Beds ⋅ 5 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

Virtually Staged. Brand new Roof and HVAC systems in 2025 and all new windows 2026. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and modern comfort. This captivating 4-bedroom, 4-bathroom home exudes warmth and sophistication, creating an inviting haven for discerning buyers. Sunlight floods every room, highlighting the home’s refined details and creating a luminous, welcoming atmosphere. Step inside to find luxurious plank flooring flowing through the entryway, family room, and guest bedrooms, complemented by polished marble in the formal living room and opulent primary suite. The interior showcases meticulous craftsmanship with recessed lighting, custom cabinetry, and coffered ceilings that add architectural charm. The heart of the home is a gourmet chef’s kitchen, a culinary dream featuring sleek custom cabinetry, a stylish farmhouse sink, a practical pot filler, and top-of-the-line appliances, perfect for both everyday meals and grand entertaining. Outside, a covered lanai invites relaxation. The sparkling pool, featuring a tranquil waterfall, soothing hot tub, and private pool bath creates a private oasis perfect for unwinding or hosting gatherings. The meticulously landscaped backyard, framed by lush greenery, offers a serene retreat for outdoor enjoyment. Soaring vaulted ceilings enhance the airy, open feel throughout the home. Located near the esteemed Rollins College and vibrant Park Avenue, this property is nestled in a charming neighborhood, offering both prestige and access to Winter Park’s finest dining, shopping, and cultural attractions. With a paved parking area, a two-car garage, and dual-zone AC for year-round comfort, this exquisite home is as practical as it is beautiful. Don’t miss the opportunity to own this Winter Park masterpiece, where timeless elegance meets modern luxury. Schedule a showing today and step into a lifestyle of comfort, sophistication, and unparalleled charm at 952 Moss Ln; this true gem is ready to become your forever home.

952 Moss Lane, Winter Park

2 Beds ⋅ 2 Baths ⋅ Orangewood Park SubDv. ⋅ 32789 Zip Code

Virtually Staged. Enjoy the best of Winter Park living from this charming 2-bedroom, 2-bath home just minutes from Park Avenue, Baldwin Park, Mills 50, Downtown Orlando, local parks, shopping, and dining. The home offers a versatile layout with a bonus room that can be used as an office, den, playroom, or additional living space, plus a second bedroom with a built-in Murphy bed for added flexibility. Outside, the circular driveway provides convenient parking, while the fenced yard and separate hobby/storage shed add both privacy and functionality. The home has also seen several important improvements, including a newer roof from 2021, A/C replaced in 2025, updated electrical systems, new security system and a new fence. A great opportunity to own a well-located Winter Park home with flexible living space and many of the major updates already completed.

2825 Mulford Avenue, Winter Park

6 Beds ⋅ 5 Baths ⋅ Waters Edge At Hawks Crest SubDv. ⋅ 32792 Zip Code

Welcome to luxury living in Hawks Crest, Winter Park’s only guard-gated community. This exceptional six-bedroom Del Rio floor plan sits on one of the neighborhood’s most coveted premium lots, featuring a larger lot line, wooded HOA land behind the property, and serene views toward Lake Howell. The thoughtfully designed floor plan offers two primary suites, one on each level, plus a dedicated office, a theater room, a loft, and a three-car tandem garage with built-in shelving and a workbench. Designer finishes include Restoration Hardware and Pottery Barn chandeliers, plantation shutters, crown molding, motorized blinds, app-controlled LED trim lighting, and custom built-ins throughout the home. The resort-style backyard features a saltwater, solar-heated pool, expansive pool deck, motorized Sunpro awnings, landscape lighting, and lanai market lights—perfect for entertaining or relaxing in complete privacy. Additional upgrades include a custom entertainment center with an electric fireplace, a Sony theater system and projector in the media room, a water softener, gutters, and extensive custom storage solutions by Inspired Closets throughout the home. The hot tub, Paradise Grill, and custom workout equipment are also available for negotiation, offering the opportunity to make this already exceptional home truly turnkey for your lifestyle. Hawks Crest residents enjoy an impressive collection of community amenities, including a resort-style pool, splash pad, clubhouse, fitness center, playground, putting green, and a private dock on Lake Howell. With highly regarded private schools nearby—including Park Maitland School, The Geneva School, Trinity Preparatory School, and The Master’s Academy—along with the exceptional shopping and dining of Park Avenue, this coveted Winter Park location truly offers the best of convenience, lifestyle, and luxury. Every box has been checked. From the premium homesite to the designer finishes, custom upgrades, resort-style pool, and thoughtful details throughout, this is a home where everything has already been done—just move in and enjoy.

1257 Wading Waters Circle, Winter Park

2 Beds ⋅ 1 Baths ⋅ Olympia Heights SubDv. ⋅ 32789 Zip Code

Welcome home to this charming 2-bedroom, 1-bathroom gem nestled in the heart of Winter Park AND College Park. This charming single-story concrete-block home blends timeless character with everyday convenience. It has a dimensional-shingle roof, and a full-length driveway leading to a covered carport deliver lasting value and practical, protected parking with an attached laundry & storage room. Located just minutes away from Downtown Orlando, Disney, Universal and Advent Health, this sought-after location offers convenience and comfort. This home boasts not only a prime location but also a cozy ambiance that will make you feel right at home. With its Terrazzo floors adding warmth and character, and the spacious fenced-in backyard providing privacy and room for outdoor activities, this property is ideal for those seeking the perks of Winter Park and College Park living as well as the fun outgoing, Orlando attractions.

1941 Oglesby Avenue, Winter Park

3 Beds ⋅ 2 Baths ⋅ Fairview Heights Rep SubDv. ⋅ 32789 Zip Code

Opportunity awaits in this 3-bedroom, 2-bath concrete block home located in the established Fairview Heights area of Winter Park. Offering 1,344 square feet of living space on a 6,460-square-foot lot, this single-story residence features a functional floor plan with tile flooring throughout the main living and dining areas. A covered rear entry leads to a brick paver patio and a fully fenced backyard with mature trees, providing space for entertaining, pets, or outdoor enjoyment. According to the seller, the roof was replaced approximately 10 years ago and the HVAC system approximately 6 years ago. Buyers are encouraged to verify all information and permits. The property is currently tenant-occupied on a month-to-month lease and may be delivered vacant at closing with a minimum of 30 days' notice, or continue as an investment opportunity. No HOA. Conveniently located near shopping, dining, parks, major roadways.

310 Granada Drive, Winter Park

5 Beds ⋅ 4 Baths ⋅ Grand Pines SubDv. ⋅ 32792 Zip Code

Very nice duplex property. No HOA. Located on a cul-de-sac. This property has a 3 bedroom 2 bath with a 2 car garage on one side and a 2 bedroom 1 bath with a 1 car garage on the other side. Both currently rented and tenant occupied. The 3/2 tenant is on a month to month lease for $2,000 per month and the 2/1 is on a 1 year lease at $1,500 per month. There are many options for you with this purchase. You can keep both sides rented, you could live in one side and rent the other or you can even split the property into two separate parcels and sell one side, as has already been done in this neighborhood. Both units have granite counters and fenced in yards.

5427 Peaco Place, Winter Park

1 Beds ⋅ 1 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code

ANOTHER 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. Make this affordable Unit your own!

1500 Gay Road Unit 4D, Winter Park

4 Beds ⋅ 4 Baths ⋅ Tantum Add SubDv. ⋅ 32789 Zip Code

Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.

922 N Pennsylvania Avenue, Winter Park

5 Beds ⋅ 6 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a large, elevated corner lot in a quiet and secluded area in the Via’s of Winter Park. This residence has been significantly enhanced inside and out by the current owner. The home features 5,200 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms ensuite, 1 half bathroom, 3 car garage, pool, patio and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler’s pantry. Past the foyer you are led to a spacious and grand formal living room with 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef’s kitchen includes newly painted custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women’s dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine iron French doors, white oak tongue and grove hardwood floors, renovated master bath and two ensuite baths, two new HVAC home units and a new garage mini-split air conditioner. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It’s also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. One or more rooms virtually staged

2228 Azalea Place, Winter Park

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