Winter Park Homes with Contemporary Architectural style

Winter Park Homes with Contemporary Architectural style

Welcome to Winter Park, Florida—a charming city known for its picturesque landscapes, vibrant arts scene, and a rich history that dates back to the late 1800s. Nestled just north of Orlando, Winter Park offers a unique blend of small-town charm and urban sophistication, making it a sought-after destination for both residents and visitors alike. With its stunning lakes, lush parks, and tree-lined streets, the city is a haven for outdoor enthusiasts and those who appreciate the beauty of nature.

One of the standout features of Winter Park is its diverse architectural landscape, particularly the contemporary homes that grace its neighborhoods. These residences showcase sleek lines, open floor plans, and an abundance of natural light, perfectly marrying form and function. Contemporary architecture in Winter Park often emphasizes sustainable living, with energy-efficient materials and designs that harmonize with the surrounding environment.

Whether you’re drawn to the modern aesthetic or the allure of a vibrant community, Winter Park’s contemporary homes offer a lifestyle that is both stylish and comfortable. Imagine sipping your morning coffee on a sun-drenched patio, surrounded by the serene beauty of your thoughtfully designed home.

With a thriving local culture, including art galleries, boutique shops, and renowned dining options, Winter Park is more than just a place to live—it’s a lifestyle choice. Explore the contemporary homes available in this enchanting city, and discover why Winter Park is the perfect place to call home. Experience the harmonious blend of modern living and timeless charm that awaits you in this Florida gem!

Newest Winter Park Homes with Contemporary Architectural style

$2,190,000
3 Beds ⋅ 4 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Experience a rare expression of design-forward lakefront living on Lake Sylvan in the heart of Old Winter Park. Fully remodeled through a comprehensive, down-to-the-studs transformation, virtually every major component is new—giving this approximately 2,400-square-foot residence the quality, systems and finishes of a modern custom home. Framed by mature live oaks and sweeping 180-degree water views, the home combines refined craftsmanship and extraordinary lakefront serenity with warm European Contemporary architecture influenced by Belgian design and Organic Modern principles. Expansive, minimalist-profile windows frame the water from nearly every principal living space, while a dramatic 12-foot sliding glass wall connects the open living area to approximately 1,500 square feet of additional outdoor living. Multiple terraces, an integrated outdoor kitchen and beautifully landscaped surroundings create an exceptional setting for waterfront entertaining or quiet mornings beneath the oak canopy. Inside, natural wood, matte black accents, architectural lighting and tactile materials establish a cohesive, warm and inviting aesthetic. Custom white oak wall panels made in Spain, hand-cut white oak beams and architectural transitions, a textured brick feature wall, built-in Sonos audio and a dedicated entertaining bar reflect the attention given to every detail. The European-inspired kitchen features full-height cabinetry incorporating materials imported from Portugal, extensive integrated pantry storage, a Thermador appliance suite with a 36-inch range and griddle, and a Miele steam oven. Positioned at the heart of the living area, the kitchen creates an effortless setting for everyday life and entertaining, always with the lake close at hand. Each of the home’s three bedrooms includes a private en-suite full bath, with an additional powder room serving the common areas. A flexible lake-view office—currently used as a fitness and sauna studio—offers an inspiring setting for work, wellness or creative pursuits. The primary suite opens through nearly eight feet of accordion-style glass doors to a private rooftop terrace, inviting morning coffee, yoga, sunbathing or evening movies beneath the sky. Beyond its architectural design, the comprehensive transformation includes a new roof and roof components, electrical wiring, plumbing and piping, four-zone HVAC system, windows, stucco, drywall, flooring, kitchen and bathrooms. The result combines the character, proportions and established setting of an Old Winter Park home with the quality, efficiency and peace of mind expected from a modern custom residence. Turnkey, distinctive and intimately connected to the water, this exceptional home brings together architectural vision, modern livability and the coveted Winter Park lifestyle on the shores of Lake Sylvan.

1420 Aloma Avenue, Winter Park
$399,900
3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code
Welcome home to this beautifully maintained, nearly new Pulte Townhome in the heart of Winter Park! Built in 2023, in the gated community of Grayson Square, this stylish two story residence offers 3 bedrooms, 2.5 bathrooms, and an attached one car garage, combining modern design with everyday convenience. The open-concept main living area is perfect for entertaining, featuring elegant quartz counter-tops, Whirlpool stainless steel appliances, ample cabinet space, and a large island overlooking the living and dining areas. Enjoy the upgraded smart home technology, high speed internet and cable already included into the low HOA, making working from home and streaming effortless. Upstairs, you will find a spacious primary suite complete with a generous walk-in closet and a private en-suite bathroom designed for comfort and relaxation. Two additional bedrooms provide plenty of room for family, guests. or a dedicated home office. Also to note is that there are no direct rear neighbors, allowing you to enjoy peaceful outdoor views on the back covered patio. The community is beautifully maintained and offers a resort-style pool and cabana and sidewalks for evening strolls. One of the homes most desirable features is the one thing you need the most but comes unseen is the 10 year transferable Pulte home warranty. Located just minutes from Winter Parks renowned shopping, dining, entertainment, parks and top commuter routes like 417, you'll enjoy easy access to everthing Central Florida has to offer while coming home to a quiet, friendly neighborhood. If your looking for a modern, energy efficient home with premium finishes and virtually maintenance free simple living, this is the one youve been waiting for!

2017 Canny Cove, Winter Park
$510,000
3 Beds ⋅ 3 Baths ⋅ Villas Of Aragon Condo SubDv. ⋅ 32789 Zip Code
Excellent Winter Park location! This 3 bedroom 2.5 bath quad-condo LIVES LIKE A PRIVATE 2-STORY HOME, with attached oversized 2 car garage, private patio and back fenced area. (The unit is attached to another only by a common garage wall.) Priced below market value to be sold AS-IS for the seller's convenience and TLC needed. ** One Year AHS Home Warranty included.** Nestled between Denning Dr and Orlando Ave, this home is an easy walk to the vibrant charm of Park Avenue, and close to the Winter Park Library, SunRail, and Rollins College. Publix and restaurants are just down the street! The first floor is tiled, with foyer entry, and comfortable family/dining/kitchen living area complete with fireplace. Sliding doors lead to a private patio. Upstairs, the large primary suite is a nice retreat with high ceilings, double walk in closets, double vanity and ample sized shower. Two more bedrooms and another bath complete the 2nd floor. High end washer and dryer are included in the attached garage, and a full wall workshop is in the garage too. Call to see it today!

1061 Aragon Avenue Unit 1061, Winter Park
$2,275,000
4 Beds ⋅ 5 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code
This WINTER PARK POOL HOME is set on a corner lot with entrances from both Palmer Avenue and Temple Drive. Located within Winter Park's exclusive J Kronenberger community, this luxury property is tucked away approximately a half mile to Winter Park's YMCA, Phelps Park & the lovely Kraft Azalea Garden, and approximately 1.5 miles to Park Avenue's restaurants, boutiques and farmer's market. The floor plan offers 4 bedrooms, 4.5 bathrooms & a home office/bonus room. The bedrooms are organized in a triple split plan arrangement that frames the open-concept gathering areas. Three bedrooms have private ensuite bathrooms, the 4th bedroom is placed directly next to the hall bath, and the office/bonus room sits adjacent to the guest half bath...everyone has a bathroom! Multiple exits lead out to the backyard, seamlessly merging the indoor and outdoor spaces. Mature hedges provide natural privacy for the open-air pool, spacious pool deck and backyard lawn. Additionally, a backyard paver path provides access to the property's 2-car detached garage. There is plenty of parking for year-round entertaining with the front half circle drive and the rear 2-car garage with multi-car driveway. This home uses natural gas to fuel the range, tankless water heater and outdoor firepit on the pool deck. Recent updates include outdoor perimeter lighting, rear fence, privacy hedges & irrigation. Prime real estate within Winter Park’s historic tree-lined streets.

1271 Palmer Avenue, Winter Park
$920,000
4 Beds ⋅ 3 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code
Experience refined Florida living in this exceptional single-story residence, ideally situated on a quiet cul-de-sac within an intimate gated community in one of Winter Park's most desirable locations. Impeccably maintained, this elegant home offers over 3,000 square feet of thoughtfully designed living space with 4 bedrooms, 3 full baths, a private office, and a desirable three-way split floor plan that provides both privacy and flexibility. Designed for comfortable everyday living and effortless entertaining, the home features formal living and dining rooms, a spacious family room, and a bright breakfast area. The stunning gourmet kitchen is the heart of the home, showcasing timeless white cabinetry, quartz countertops, abundant prep space, a convenient butler's pantry, and an open flow to the main living areas. The generous primary suite offers a spacious walk-in closet and a luxurious retreat, while quality finishes and meticulous attention to detail are evident throughout. Enjoy year-round outdoor living on the private screened lanai, perfect for relaxing or entertaining. Additional highlights include a three-car garage, a durable tile roof, and a fully paid solar energy system, keeping the average monthly electric bill under $100. Combining elegance, energy efficiency, and an outstanding location, this move-in-ready home offers the perfect balance of luxury, comfort, and convenience.

1492 Via Sangro Pl, Winter Park
$525,000
3 Beds ⋅ 4 Baths ⋅ Quarters At Winter Park Condo SubDv. ⋅ 32789 Zip Code
Beneath mature oak trees in The Quarters at Winter Park, this townhome-style condominium presents a rare opportunity to own a spacious, architecturally distinctive residence in one of Winter Park's most established communities. Priced to reflect its as-is condition, the home offers exceptional potential for a buyer ready to personalize the space. A gated brick courtyard and covered front porch lead to light-filled living and dining areas featuring engineered hardwood flooring and a wrought-iron staircase. The kitchen offers granite countertops, a gas range and opens to the family room, where a gas fireplace and skylight create a welcoming gathering space. A private screened courtyard connects the residence to the detached two-car garage. Upstairs, the primary suite spans more than 300 square feet and features a custom walk-in closet and dual-sink en-suite bath. Two additional bedrooms include one with a private en-suite bath and another with access to a balcony overlooking the tree-lined street. Ideally just minutes from Park Avenue, Rollins College and Seven Oaks Park, this residence offers the opportunity to renovate and customize a home in one of Winter Park's most sought-after communities. Sold as is, with an inspection report available upon request.

1134 Washington Avenue Unit 13C, Winter Park
$255,000
3 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Rare end units like this don't come around often! Welcome to 2450 Grand Teton Circle, tucked away in the well-maintained, established community of Cedarwood Village in Winter Park. This 3-bedroom, 2-bath home is filled with natural light thanks to its end-unit location, and the open layout makes it easy to relax, entertain and enjoy everyday living. The spacious living and dining areas flow together nicely, while the kitchen offers plenty of room to cook, gather, and stay connected with family and friends. Over the past several years, this home has been thoughtfully updated, giving the next owner peace of mind. Major improvements include a new roof, skylights, HVAC system, water heater, kitchen appliances, washer and dryer, updated LED lighting, and fresh interior paint. Both bathrooms have been beautifully remodeled, the home has been replumbed by the HOA, and the primary closet has been enhanced with custom shelving. Additional updates include new flooring in the secondary bedrooms, updated window blinds, and thoughtful finishing touches throughout. The private screened lanai has been transformed into a cozy outdoor retreat with fresh paint, a ceiling fan, new screens and screen door, string lighting, and decorative greenery—making it the perfect place to enjoy your morning coffee or unwind after a long day. Life here is easy. Cedarwood Village is a beautifully maintained, established community featuring a community pool and Clubhouse for your special events, tennis courts, and pickleball courts. The HOA has also recently repainted the exterior of the buildings, helping keep the neighborhood looking fresh and inviting. Best of all, this home is value priced, giving you an incredible opportunity to own in desirable Winter Park without the premium price tag. You're just minutes from Winter Park's shopping and dining, Full Sail University, UCF, major employers, and convenient access to SR-417 and downtown Orlando. If you've been looking for a move-in-ready home in a fantastic location with years of thoughtful updates already completed, this rare end unit is definitely worth a look!

2450 Grand Teton Circle Unit 2450, Winter Park
$465,000
3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the highly desirable Winter Park area. Combining comfort, style, and an unbeatable location, this charming residence offers the perfect opportunity for homeowners seeking a move-in-ready property in one of Central Florida's most sought-after communities. Step inside to discover a bright and inviting floor plan designed for both everyday living and entertaining. The well-appointed kitchen features stainless steel appliances, granite countertops, and ample cabinetry, creating a functional and stylish space for preparing meals and gathering with family and friends. The home's well-maintained interior reflects pride of ownership throughout, offering a warm and welcoming atmosphere from the moment you arrive. The spacious living areas and comfortable bedrooms provide plenty of room to relax and unwind, while the thoughtful layout maximizes both comfort and convenience. Whether you're hosting guests, working from home, or simply enjoying a quiet evening in, this home is designed to fit a variety of lifestyles. Located in the heart of Winter Park, you'll enjoy easy access to the area's renowned dining, shopping, parks, and cultural attractions. Spend weekends exploring the boutiques and cafés along Park Avenue, enjoying a scenic boat tour through Winter Park's picturesque lakes, or visiting nearby gardens, museums, and recreational trails. With convenient access to Downtown Orlando, major employers, top-rated schools, and world-famous attractions, this location offers the perfect balance of suburban charm and urban convenience. Don't miss this opportunity to own a well-cared-for home in one of Central Florida's premier neighborhoods. Schedule your private showing today and discover everything this wonderful Winter Park property has to offer!

3641 Hawthorne Lane, Winter Park
$1,725,000
6 Beds ⋅ 6 Baths ⋅ Lake Florence Preserve SubDv. ⋅ 32792 Zip Code
Welcome to an exceptional lakefront home in the gated community of Lake Florence Preserve, where luxury, space, and lifestyle come together in the heart of Winter Park. This stunning 6-bedroom, 5+ bath pool home sits on the shores of private, Lake Florence, offering a rare opportunity for true waterfront living. Step inside to a grand two-story entry with soaring 10-foot ceilings and an open-concept layout designed for effortless entertaining. Natural light fills the expansive living, dining, and kitchen spaces, highlighting the home’s high-end finishes and thoughtful design. At the center of the home is a chef’s kitchen featuring an oversized 11’ x 5’ island, gas range with vent hood, premium Samsung and GE appliances, and an impressive 10’ x 4’ walk-in pantry, perfect for hosting or daily convenience. With six generously sized bedrooms, including a private in-law suite, this home offers flexibility for multigenerational living or guests. Upstairs, the spacious primary suite boasts lake views, a large ensuite bath, and dual walk-in closets. You’ll also find a versatile 19’ x 18’ game room with a 17' wide balcony overlooking the pool and lake, along with an oversized second-floor laundry room. Outdoor living is where this property truly shines. Enjoy direct access to Lake Florence from your private dock with electric boat lift, ideal for boating, jet skiing, or peaceful sunset cruises. The backyard is designed for relaxation and entertaining, complete with a saltwater pool, fully fenced yard, tiki hut featuring an outdoor kitchen and outdoor shower fitted with hot and cold water. Additional highlights include a 3-car garage, tankless water heater, custom closets throughout, and upgraded lighting and ceiling fans. Ideally located just minutes from SR 436, the 417, and only 15 minutes to Park Avenue, this home offers both convenience and exclusivity within a sought-after gated community. This is a rare opportunity to own a true lakefront retreat. Schedule your private showing today.

2914 Reef Knot Place, Winter Park
$5,500,000
4 Beds ⋅ 5 Baths ⋅ Sylvan Park SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportunity to own a thoughtfully curated custom home by renowned builder Floridian Custom Homes, brought to life in collaboration with Winter Park Design, Brianna Michelle Interior Design and Signature Landscape. Offering 4,775 heated square feet of expertly crafted living space, this four-bedroom plus office, four-and-one-half-bath home blends timeless architecture, elevated finishes and effortless lakefront living. Designed with an open-concept floor plan ideal for everyday living and entertaining, the home showcases stunning European white oak hardwood flooring throughout all main living areas and bedrooms. The heart of the home is the spectacular chef’s kitchen, featuring two oversized islands, custom-designed wood cabinetry, an expansive walk-in pantry, and a premium Sub-Zero and Wolf appliance package highlighted by a 48-inch, eight-burner range. The private first-floor primary suite serves as a luxurious retreat, complete with an expansive walk-in closet and a spa-inspired bath adorned with marble tile shower walls and flooring. Also on the main level is a versatile office/den with a built-in closet. Upstairs, an expansive media/family room provides additional gathering space, accompanied by a dedicated office and three generously sized secondary bedrooms, each featuring en-suite baths and walk-in closets. The fourth bedroom offers exceptional flexibility and may easily serve as a secondary primary suite, ideal for guests or multigenerational living. Designed to embrace seamless indoor-outdoor living, expansive glass sliders extend from the gathering and dining rooms to a covered lanai overlooking the resort-style custom pool. Retractable screens create a setting for year-round enjoyment, while the fully equipped summer kitchen and generous lounge and dining areas make entertaining effortless. Expertly designed by Signature Landscape, the pool features a sun shelf, LED lighting and elegant travertine limestone decking, all surrounded by lush professional landscaping, Zoysia grass and privacy hedging for a serene outdoor setting. Additional notable features include a Brava slate tile roof and a striking custom glass front entry door, further elevating the home’s exceptional curb appeal. Ideally just minutes from the vibrant shops and dining of Park Avenue, this remarkable residence also offers convenient access to major roadways, leading area hospitals and top private schools, all within an A-rated school district. An exceptional opportunity to enjoy luxury lakefront living in one of Central Florida’s desirable settings.

313 Sylvan Drive, Winter Park
$490,000
4 Beds ⋅ 2 Baths ⋅ Cedar Ridge SubDv. ⋅ 32792 Zip Code
Virtually Staged. Discover space, comfort, and flexibility in this beautifully updated 4-bedroom, 2-bath home in the highly desirable Cedar Ridge community of Winter Park with no HOA. Offering approximately 2,250 square feet of living space, this home also features a versatile flex room ideal as a nursery, home office, guest suite, media room, or private retreat. The 2025 remodeled kitchen offers abundant cabinetry and pantry storage, while the renovated bathrooms feature stylish, modern finishes. Ceramic tile flows throughout most of the home, with warm wood-look flooring in three bedrooms for added comfort. Enjoy peace of mind with major improvements already completed, including a 2024 roof, 2023 whole-home replumbing, and 2023 electrical panel replacement with generator hookup. These significant updates allow you to focus on enjoying your new home instead of tackling major projects. Step outside to an oversized, fully fenced backyard shaded by two magnificent mature oak trees, creating a private setting for relaxing, entertaining, or family gatherings. A side-entry two-car garage adds both curb appeal and everyday convenience. Conveniently located just minutes from Baldwin Park, UCF, shopping, dining, parks, and Seminole County schools, this Cedar Ridge home offers exceptional space, recent major updates, and the convenience of an established Winter Park neighborhood with no HOA.

2008 Houndslake Drive, Winter Park
$435,000
4 Beds ⋅ 3 Baths ⋅ Trinity Bay SubDv. ⋅ 32792 Zip Code
Welcome to 8433 Commander Cove, ideally situated on a quiet cul-de-sac in the highly sought-after Trinity Bay community. Upon entering this spacious home you're greeted by soaring vaulted ceilings, a formal dining area, and a stunning cathedral-style front window that fills the space with natural light. The separate enclosed kitchen offers functionality and charm, with French doors leading to a covered, tiled lanai. Step outside and enjoy a large patio surrounded by mature trees and lush landscaping—an ideal setting for morning coffee, outdoor entertaining, and family barbecues. The inviting family room showcases vaulted ceilings, a grand brick fireplace, and a versatile bonus den/office with a window, perfect for working from home or additional living space. Conveniently located off the family room is an indoor laundry area and half bath. The first-floor primary suite offers privacy and comfort, featuring a dual-vanity bathroom and private French door access to the covered lanai. Upstairs, you'll find three generously sized bedrooms, each equipped with ceiling fans and ample closet space, along with a second dual-vanity full bathroom. Whether you're a first-time homebuyer or looking for room to accommodate a growing family, this home offers exceptional value and functionality. Residents of Trinity Bay enjoy access to a community pool, community playground, and a private neighborhood boat ramp with access to the Lake Burkett and Lake Martha Chain of Lakes, where boating, water skiing, fishing, and other recreational activities are welcomed. Don't miss this opportunity to own a beautiful home in one of the area's most desirable neighborhoods!

8433 Commander Cove, Winter Park
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