Winter Park Homes with 2 Car Garage Garage Description

Winter Park Homes with 2 Car Garage Garage Description

Welcome to Winter Park, Florida – a picturesque city renowned for its stunning landscapes, vibrant culture, and welcoming community. Nestled just north of Orlando, Winter Park is a hidden gem that boasts a unique blend of historic charm and modern amenities. With its tree-lined streets, beautiful lakes, and an array of parks, this city is perfect for those who appreciate nature and outdoor activities.

One of the highlights of Winter Park is its thriving arts scene, featuring the renowned Charles Hosmer Morse Museum of American Art, which houses the world's most extensive collection of Tiffany glass. The city also offers a delightful selection of boutique shops, gourmet restaurants, and lively cafes that cater to every palate. Additionally, the Winter Park Farmer's Market is a must-visit, showcasing local produce and artisanal goods every Saturday morning.

For families and individuals looking to settle down, Winter Park offers a variety of housing options, including homes with two-car garages. These spacious residences provide ample room for vehicles, storage, and recreational activities, making them an ideal choice for those who value convenience and functionality. Whether you're a busy professional, a growing family, or someone who simply enjoys the extra space, homes with true two-car garages in Winter Park are designed to meet your needs.

Living in Winter Park not only means enjoying a beautiful home but also being part of a community that values art, culture, and outdoor living. Experience the charm and warmth of Winter Park, where your dream home awaits!

Newest Winter Park Homes with 2 Car Garage Garage Description

1830 Gladiolas Drive, Winter Park
$375,000
3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code
Welcome to 1830 Gladiolas Drive, a beautiful 3 bedroom, 2 bathroom home in Winter Park’s Garden Lake Estates community. This move-in ready home features a 2023 AC, a 2022 water heater, a 2020 roof, and a brand new freshly painted interior. Inside, the spacious open living and kitchen area is the heart of the home. The thoughtful layout keeps everyone connected, whether you’re cooking, hosting friends, or settling in for a quiet evening. Natural flow between the spaces makes the home feel open and welcoming. The primary suite is a private retreat. It’s generously sized and has a large walk-in closet, so you have plenty of room for your wardrobe and a calm place to start and end your day. Outside, the expansive rear patio extends your living space into the Florida outdoors. It’s ready for morning coffee, weekend barbecues, or dinner under the stars. Beyond it, the big backyard gives you room to play, garden, or add the features you’ve been dreaming of. Functional, inviting, and close to everything in Winter Park, this home is ready for its next chapter with several major updates already completed. This home is a great opportunity for someone looking to add their own personal touch.

1830 Gladiolas Drive, Winter Park
1021 Princess Gate Boulevard, Winter Park
$410,000
3 Beds ⋅ 2 Baths ⋅ Howell Estates Rep SubDv. ⋅ 32792 Zip Code
Welcome to this 3-bedroom, 2-bath pool home in the established Howell Estates neighborhood of Winter Park! Situated on a spacious 0.31-acre lot, this single-story residence offers 1,318 square feet of living space with a split-bedroom layout and a combination of tile and luxury vinyl flooring. The living room features built-in cabinetry with a granite countertop, while the kitchen offers stone countertops, a tile backsplash, and a closet pantry. The primary suite includes dual closets and a private bathroom with a walk-in shower. Sliding glass doors from the dining area open to a covered lanai and screened-in pool, creating an inviting setting for outdoor relaxation and entertaining. The spacious, fenced backyard offers additional room to enjoy the outdoors. Other highlights include a brand-new water heater, a 2018 roof, a 2024 HVAC system, and no HOA fees. Conveniently located near Howell Branch Road and Semoran Boulevard, the property provides access to shopping, dining, parks, and everyday essentials throughout the Winter Park area. With its private pool, generous lot size, and convenient location, this home offers a wonderful opportunity to enjoy Florida living. Schedule your private showing today!

1021 Princess Gate Boulevard, Winter Park
1735 Demetree Drive, Winter Park
$1,050,000
4 Beds ⋅ 3 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code
Beautifully maintained Winter Park pool home with a 2026 whole-home repipe, 2019 roof, and 2022 A/C in the desirable Waterbridge neighborhood. Discover the charm of established Winter Park living in this inviting single-story home, situated on a beautifully landscaped 0.36-acre lot in the sought-after 32789 ZIP code. Spacious living areas, abundant natural light, and two inviting fireplaces, including a fireplace in the living room and a distinctive stone fireplace in the primary suite, create a warm and welcoming atmosphere. Step outside to your private swimming pool, surrounded by mature landscaping, offering the perfect setting for relaxing or entertaining. Additional features include a tankless water heater, updated pool equipment, and access to Waterbridge neighborhood tennis courts. An exceptional Winter Park location. Enjoy convenient proximity to AdventHealth Winter Park Hospital, the Winter Park VA Clinic, and Winter Park High School, along with easy access to downtown Winter Park's iconic Park Avenue, renowned restaurants, boutique shopping, Rollins College, Mead Botanical Garden, and downtown Orlando. Combining valuable improvements, single-story convenience, private pool living, and an established neighborhood setting, 1735 Demetree Drive offers the character, comfort, and lifestyle that make Winter Park, Florida, such a desirable place to call home.

1735 Demetree Drive, Winter Park
624 Dunraven Drive, Winter Park
$620,000
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 05 SubDv. ⋅ 32792 Zip Code
Welcome to this charming Winter Park home, featuring classic terrazzo floors and wonderful natural light. This home boasts a cozy wood-burning fireplace that serves as a focal point in the kitchen and living room, creating a warm and welcoming atmosphere. Culinary enthusiasts will delight in the kitchen's features, including an island with a breakfast bar, storage and power, elegant pendant lights, soft-close drawers and cabinets, and a stylish tile backsplash. Granite countertops and stainless-steel appliances, including a brand-new gas range, complete the culinary experience. The separate family room, with beautiful laminate flooring, offers an additional living space, perfect for relaxation or entertaining. From here, step into the enclosed lanai, where windows wrap around the entire space, offering lovely views and access to the fenced, landscaped backyard. This home also offers generous storage closets for all your needs. The primary bedroom offers a walk-in closet and ensuite bathroom with a granite counter vanity with soft-close drawers and cabinets. The remaining bedrooms share a hall bath with a dual sink granite vanity and a tub/shower combination. Located in a tremendous area, this home is just a short distance from the vibrant communities of Winter Park and Baldwin Park, and within walking distance to Winter Park High School. Other updates include a newer water heater (2024) and newer windows and doors (2020). Don't miss the opportunity to make this lovely home your own!

624 Dunraven Drive, Winter Park
1631 Hillcrest Avenue, Winter Park
$4,500,000
5 Beds ⋅ 6 Baths ⋅ Ellno Willo SubDv. ⋅ 32789 Zip Code
Brand new construction (2023) on a beautifully sized .29± acre lot in the heart of Winter Park. This 5BR/5.5BA estate offers an open-concept layout with high ceilings, abundant natural light, and premium finishes throughout. Every bedroom features its own en-suite bath. Resort-style pool and putting green anchor the outdoor living space, perfect for Florida's year-round lifestyle. Detached garage offers flexible storage, workshop space, plus room for a private home gym. Minutes from Park Avenue's shops, dining, and top-rated schools. Top quality construction and unbeatable location. Schedule your private showing today.

1631 Hillcrest Avenue, Winter Park
1825 Whitehall Drive, Winter Park
$3,195,000
4 Beds ⋅ 6 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code
1825 Whitehall Drive announces itself in stone. Twin gables of whitewashed natural stone, a stately brick entry, and striking black-framed windows define its European-inspired architecture in Winter Park’s coveted Kenilworth Shores. Brand-new and awaiting its first owner, this expansive custom residence offers over 4,300 square feet of timeless character and bespoke craftsmanship. Inside, natural light moves across wide-plank engineered white oak floors. Grand entertaining spaces meet intimate rooms, rich in architectural elegance. Architectural symmetry defines the great room, where a soaring fluted terrazzo fireplace is framed by custom walnut cabinetry and brass picture lights. Expansive glass opens to the lanai, while a sitting room features a custom bar with brass mesh cabinetry, illuminated shelving, glazed tile, and wine refrigeration. The kitchen is a masterpiece, and you'll know it the moment you walk in. A Taj Mahal quartzite island commands the room, framed by floor-to-ceiling bespoke cabinetry, illuminated reeded glass, and a sculptural fluted hood. Sweeping waterfall edges meet a custom fluted wood base. A 48-inch Viking gas range, double ovens, and separate refrigerator and freezer columns complete the kitchen. Beyond, a windowed butler’s pantry offers quartzite countertops, illuminated shelving, and beverage refrigeration. Opening to the pool, the dining room invites memorable dinners that linger long after the last guest should have left. And then there's the first-floor primary suite—where luxury becomes personal. Vaulted ceilings with stained oak beams bring warmth and architectural character, while the bathroom is a destination in itself. Brass-inlaid marble floors, lilac-veined stone, a quartzite double vanity, and makeup station introduce a spectacular wet room with four rainfall showerheads, two handheld showers, and a sculptural fluted soaking tub. An oversized, fully customized walk-in closet features built-in cabinetry and elegant glass-front displays. Just off the foyer, the library is a room you'll fall in love with. Color-drenched walls, a stained oak-plank ceiling, custom built-ins, and brass-lit shelving create an intimate retreat, enclosed in glass with doors to a secluded side patio. The mudroom, plum-cabinetry laundry, and plaster-inspired powder bath complete the level. Upstairs, a light-filled loft opens to an uncovered terrace with checkerboard stone flooring, made for sunset conversations beneath the stars. Three bedrooms each feature an en-suite bath and custom closet. A jewel-box powder bath and vaulted bonus room, ideal for a cinema or game lounge, complete the level. Outside, a covered lanai with stained tongue-and-groove ceiling features a summer kitchen in whitewashed brick, fluted cabinetry, and leathered granite. French-pattern Talya leathered stone frames the PebbleTec pool, tanning ledge, inset spa, and calming waterfall—a setting made for sunlit afternoons, entertaining, and memorable evenings. Custom-built by Structure Redevelopment, LLC, this residence reflects a passion for distinctive architecture, superior craftsmanship, and uncompromising detail. Among Kenilworth Shores' distinguished residences and lakefront estates, it places you moments from Park Avenue’s restaurants, boutiques, and cafés, Rollins College, and the Chain of Lakes. Schedule your private showing today.

1825 Whitehall Drive, Winter Park
1458 Lone Feather Trail, Winter Park
$650,000
4 Beds ⋅ 3 Baths ⋅ Landings At Hawks Crest SubDv. ⋅ 32792 Zip Code
Virtually Staged. Set within the guard-gated community of Hawk’s Crest, this inviting single-story residence offers a beautifully maintained open floor plan with more than 1,700 square feet of comfortable living space and approximately $15,000 in luxurious recent upgrades. Fresh interior paint and neutral finishes create a bright, welcoming atmosphere, complemented by ceramic tile flooring throughout the main living areas and new carpeting in the bedrooms. At the heart of the home, the spacious kitchen features gray cabinetry, a new range and oven, stainless steel appliances, generous counter space, an expansive center island and a large pantry, opening seamlessly to the dining and living areas. The primary suite offers a spacious retreat with a walk-in closet and an en-suite bath featuring dual vanities and a walk-in shower, while additional bedrooms provide flexibility for family, guests or a home office. Sliding glass doors extend the living space to the screened lanai, enhanced with updated decking and an inviting setting for outdoor relaxation. Beyond the lanai, the fully fenced backyard, featuring newly installed fencing and landscaping, offers additional privacy and ample space for outdoor enjoyment. Residents of Hawk’s Crest enjoy resort-style amenities, including a community pool, clubhouse, fitness center, splash pad, playgrounds, dog park and private access to Lake Howell, along with the convenience of Park Maitland Preschool, Kelly’s Ice Cream and Foxtail Coffee at the community entrance. Ideally positioned near Winter Park’s renowned shopping, dining and everyday conveniences, this home offers an exceptional opportunity to enjoy the Hawk’s Crest lifestyle.

1458 Lone Feather Trail, Winter Park
1681 Woodland Avenue, Winter Park
$2,629,000
5 Beds ⋅ 5 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code
Under Construction. A striking interpretation of Modern Tudor design brings a fresh architectural presence to one of Winter Park’s charming brick streets. Newly built, this stunning residence pairs a distinctive façade with interiors that feel both richly detailed and effortlessly livable. From the marble mosaic foyer to the private poolside retreat, each space offers its own expression of luxury, creating a home with character, warmth, and a beautiful sense of arrival. Beyond the entry, the spacious living area unfolds beneath shiplap ceiling details that lend texture and architectural depth. A statement wall with an electric fireplace anchors the room, establishing an inviting setting for quiet evenings and lively gatherings alike. The kitchen takes center stage with Taj Mahal countertops and a full suite of Thermador appliances. A built-in paneled refrigerator preserves the cabinetry’s seamless appearance, while a spacious walk-in pantry provides ample storage beyond the main kitchen. Positioned downstairs, the primary suite offers a peaceful retreat with a spacious closet and a beautifully composed spa bath featuring dual vanities, a freestanding soaking tub, and a separate shower with a rain showerhead and marble mosaic tile. A second downstairs guest suite adds exceptional versatility, a rare feature for the area, providing comfortable accommodations for visitors or a space for a private office. Providing comfortable accommodations for visitors or an inspiring space for a private office. Upstairs, three additional bedrooms, each with a walk-in closet, offer room for family and guests. A spacious loft introduces another place to gather, unwind, or create a dedicated media or recreation space, while the upstairs laundry room brings convenience to daily routine. Outdoors, a covered lanai with a summer kitchen sets the scene for alfresco dining and entertaining space. Lush landscaping surrounds the pool and spa, creating a beautiful backdrop for entertaining or simply enjoying the Florida lifestyle. Energy efficient doors and windows complete the home’s thoughtful collection of features. The location places neighborhood favorites within easy reach, with Phelps Park and the YMCA just a walk away and Park Avenue’s shops, restaurants, and cafés a short golf cart ride from home. Distinctive in its architecture and generous in its design, this residence offers a compelling opportunity to enjoy brand-new construction amid the established charm of Winter Park.

1681 Woodland Avenue, Winter Park
8061 Pleasant Pine Circle, Winter Park
$750,000
5 Beds ⋅ 4 Baths ⋅ Enclave At Aloma SubDv. ⋅ 32792 Zip Code
Welcome to this great 5 bedroom, 3 and a half bathroom almost 3500 square foot Winter Park home! The home not only has these spaces but also is in excellent condition with; new interior paint, new carpet, 2 heating and cooling systems replaced in 2024! The open concept center island kitchen has upgraded counters, 42" cabinets and a double convection oven! Downstairs there is a formal living and dining room, an open concept kitchen, nice warm low maintenance ceramic tile, a convenient downstairs bedroom that would also be a great office/craft/game/guest room!! Upstairs are the other private bedrooms and a huge bonus theater/media/entertainment space.. The oversized primary bedroom is upstairs for complete privacy and has a well appointed bathroom as well as two walk in closets!! Come home and relax in your fenced back yard that has a peaceful forest behind it, set up a hammock and.... This fine gated community is located so close to so much, The University of Central Florida, Winter Park, Downtown Orlando, Trinity Preparatory Academy, The Masters Academy, The Geneva School, the Space Coast, Cocoa Beach and more!!

8061 Pleasant Pine Circle, Winter Park
1751 Glencoe Road, Winter Park
$3,390,000
5 Beds ⋅ 7 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code
Set along a picturesque brick street in Winter Park’s coveted Lake Sue District, this extraordinary residence delivers the scale, craftsmanship, and thoughtful design rarely found in such a desirable location. Positioned on an expansive homesite with an impressive architectural façade and meticulously curated landscaping, the home makes an unforgettable first impression before revealing an interior designed for both elevated entertaining and everyday living. A dramatic foyer with soaring 22-foot ceilings introduces an exceptional floor plan. To one side, a color-drenched private office is enveloped in custom trim work, while the formal dining room opposite features floor-to-ceiling windows and an elegant coffered ceiling. Beyond, the expansive living room is anchored by a stone-wrapped fireplace and framed by arched built-in shelving with integrated LED lighting. Natural wood beams add warmth and architectural character, creating a space that feels equally refined and inviting. The chef’s kitchen is a statement in both beauty and performance, showcasing custom cabinetry, quartz countertops, a professional Wolf gas range, and an oversized paneled Sub-Zero refrigerator. Overhead beams bring dimension to the space, while the adjoining breakfast nook, with custom built-in bench seating offers a charming setting for casual dining. A generously sized butler’s pantry and laundry room provide exceptional storage and functionality. Privately positioned on the main level, the primary suite opens directly to the covered lanai. Its spa-inspired bath is finished in beautiful marble and features dual vanities with floating mirrors, an expansive wet room with a freestanding soaking tub, and a fully customized wardrobe by award-winning Idelli Closets. Upstairs, a spacious loft creates an additional living area surrounded by four generously proportioned bedroom suites, each complete with a private bath and walk-in closet. A second laundry room adds convenience to the upper level. The outdoor setting rivals a private resort. A magazine-worthy summer kitchen anchors the expansive covered lanai, while retractable screens allow for comfortable year-round entertaining. Beyond, a heated pool and spillover spa are complemented by marble decking and additional green space. Just moments from Lake Sue, Park Avenue, Rollins College, East End Market, and zoned for highly sought-after Audubon Park School, this remarkable residence presents an exceptional opportunity to experience one of Winter Park’s most compelling homes.

1751 Glencoe Road, Winter Park
2219 Winter Woods Boulevard, Winter Park
$479,999
3 Beds ⋅ 3 Baths ⋅ Winter Woods Unit 01 SubDv. ⋅ 32792 Zip Code
This 3-bedroom, 2.5-bath home offers approximately 1,776 square feet of living space on a spacious 0.24-acre lot. The two-story floor plan provides flexible living arrangements, while the generous yard offers outdoor space for relaxing, gardening, or entertaining. Additional features include central air conditioning and garage parking. Recent improvements include new roof, new HVAC, new water heater and much more.

2219 Winter Woods Boulevard, Winter Park
1737 Indiana Avenue, Winter Park
$1,399,900
4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
WELCOME to this farmhouse-inspired residence combines timeless architectural character with modern luxury and thoughtful design. ***A welcome front porch leads to an impressive two-story foyer and bright, open floor plan designed for comfortable living and effortless entertaining. A private fourth bedroom with a full bath is located near the entry, offering flexibility as a guest suite, home office, study, or secluded retreat. ***KITCHEN & MAIN LIVING AREAS: The gourmet kitchen serves as the heart of the home, featuring quartz countertops, custom cabinetry, and a premium Bosch appliance package with a 36-inch electric cooktop. Open to the spacious living and dining areas, it creates a seamless setting for everyday living and entertaining. ***PRIMARY SUITE & UPSTAIRS SPACES: The first-floor primary suite provides a peaceful retreat with a spa-inspired bath, dual vanities, a freestanding soaking tub, and a generous walk-in closet with custom shelving. A nearby laundry area adds convenience and efficiency. Upstairs, a spacious bonus room with a closet can function as a fifth bedroom, media room, game room, home office, creative studio. Two additional bedrooms feature walk-in closets and share a beautifully appointed bathroom with dual sinks. A second laundry room with a sink and abundant natural light adds further convenience. ***OUTDOOR LIVING: The covered lanai overlooks a sparkling pool and beautifully landscaped backyard, creating for the outdoor relaxation and entertaining. The entire covered porch features a motorized retractable screening system, allowing the space to be fully screened in. Low-maintenance artificial turf keeps the backyard looking lush and green year-round without the need for mowing, while an additional mosquito repellent system enhances outdoor enjoyment. ***LOCATION: Perfectly positioned near Winter Park's acclaimed shopping, fine dining, beautiful parks, and vibrant cultural attractions, this exceptional location also offers effortless access to I-4 and Downtown Orlando, Winter Park Village, Publix, Trader Joe's, and much more, making it easy to enjoy everything Central Florida Lifestyle. Make an appointment today before this beautiful, amazing home is gone!!!

1737 Indiana Avenue, Winter Park
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