Winter Park, FL Houses for Sale

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  $5,950,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,448 Sq Ft

  1181 Via Capri, Winter Park, FL 32789

  Under Construction. Situated on one of the choicest streets in Winter Park on a large and lovely lot will soon be a Phil Kean Design Group new construction project.Enjoy a world class location along with award winning Architecture and Design.Construction is expected to be complete in mid 2026.A Phil Kean Design Group representative can be available for a sit down to discuss complete

  Brad Grosberg PHIL KEAN REAL ESTATE LLC

  1181 Via Capri, Winter Park, FL 32789
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  $4,250,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 3,413 Sq Ft

  1120 Palmer Ave, Winter Park, FL 32789

  Spectacular Phil Kean Design Group whole home remodel coming soon.Miami/Coral Gables Cottage meets Winter Park Elegance.On a street of Winter Park estates this home will be a charming and sophisticated addition.Currently under construction and being reimagined for the 2026 International Builders Show "Show Home Remodel".This home will be available for occupancy in February

  Brad Grosberg PHIL KEAN REAL ESTATE LLC

  1120 Palmer Ave, Winter Park, FL 32789
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  $5,549,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,096 Sq Ft

  698 N New York Ave, Winter Park, FL 32789

  Under Construction. Rare, new construction opportunity in the heart of Winter Park just 1 block from Park Avenue being built FG Schaub Custom Homes, known for grand open spaces and superior craftsmanship. No expense was spared in designing this Transitional, two-story residence with 5 bedrooms, 5.5 bathrooms, an office, elevator and sauna. As you enter into the grand two story foyer, you will be

  Laura Earl CORCORAN PREMIER REALTY

  698 N New York Ave, Winter Park, FL 32789
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  $1,275,000 New Construction

  • 4 Beds
  • 3 Baths
  • 3,710 Sq Ft

  5236 Lake Howell Rd, Winter Park, FL 32792

  Experience the best of Winter Park living in this stunning new custom-built pool home situated on a generous .29-acre lot just 1.9 miles from Park Avenue. Designed with a modern aesthetic and built to the highest standards, this 4-bedroom, 3-bath residence is a true showcase of craftsmanship and luxury. Step inside to discover a stunning vaulted great room where the kitchen, living, and dining

  Troy Hensley BHHS FLORIDA REALTY

  5236 Lake Howell Rd, Winter Park, FL 32792
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  $1,390,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,253 Sq Ft

  501 Lakeview Ave, Winter Park, FL 32789

  Under Construction. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting facade you’ll find an airy two-story layout featuring four bedrooms and 4 1⁄2 baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright loft that easily flexes as a

  Marie Ledbetter COLDWELL BANKER RESIDENTIAL RE

  501 Lakeview Ave, Winter Park, FL 32789
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  $1,390,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,253 Sq Ft

  525 Lakeview Ave, Winter Park, FL 32789

  Under Construction. Renderings available soon. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting facade you’ll find an airy two-story layout featuring four bedrooms and 4 1⁄2 baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright

  Marie Ledbetter COLDWELL BANKER RESIDENTIAL RE

  525 Lakeview Ave, Winter Park, FL 32789
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  $4,750,000 New Construction

  • 4 Beds
  • 5.5 Baths
  • 3,850 Sq Ft

  1150 Via Salerno, Winter Park, FL 32789

  In the heart of Winter Park’s coveted Vias neighborhood, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Designed and developed by Steve and Jodie Warrick Konold of Scout & Co., the 3,850 sf layout offers 4 bedrooms & 5.5 baths, wrapped in the intentional privacy of a luxury retreat. Beyond its terraced walkway and

  Padgett McCormick KELLY PRICE & COMPANY LLC

  1150 Via Salerno, Winter Park, FL 32789
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  /75

  $3,895,000 New Construction

  • 5 Beds
  • 7 Baths
  • 4,055 Sq Ft

  1820 Glencoe Rd, Winter Park, FL 32789

  Discover the ultimate in luxury real estate in Winter Park, Florida with this Dutch West Indies–inspired custom home built by FG Schaub Custom Homes. Ideally located just minutes from Park Avenue’s upscale dining and shopping, Rollins College, and the cultural charm of downtown Winter Park, this residence combines timeless architecture with modern elegance. Offering over 4,055 square feet of

  Laura Earl CORCORAN PREMIER REALTY

  1820 Glencoe Rd, Winter Park, FL 32789
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  $1,649,900 New Construction

  • 4 Beds
  • 4 Baths
  • 2,743 Sq Ft

  1780 Mizell Ave, Winter Park, FL 32789

  Discover modern luxury living in this newly constructed, architect-designed residence by Gary Hancock, ideally located in the heart of Winter Park. Offering nearly 2,800 square feet of thoughtfully planned living space, this four-bedroom, four-bath home combines timeless architecture with premium finishes for an elevated lifestyle experience.Step inside to 10-foot ceilings on both levels,

  Megan Byers PREMIER SOTHEBY'S INTL. REALTY

  1780 Mizell Ave, Winter Park, FL 32789
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  $1,201,000 New Construction

  • 5 Beds
  • 3 Baths
  • 2,618 Sq Ft

  1807 Magnolia Ave, Winter Park, FL 32789

  Under Construction. Scheduled to start in September 2025 with estimated completion in March 2026. New construction in the City of Winter Park! This home has been thoughtfully designed, but there is still time to make personalized finish selections if desired. This deep 56 x 157 lot is Winter Park's best kept secret, located in a quiet pocket of 32789. The huge backyard will be ~55-ft deep once

  Kristen Hamilton LOMBARDO TEAM REAL ESTATE LLC

  1807 Magnolia Ave, Winter Park, FL 32789
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  $3,150,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,553 Sq Ft

  541 W Canton Ave, Winter Park, FL 32789

  Timeless elegance meets boutique craftsmanship at 541 W Canton Avenue—an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Located just steps from Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm.From its dormer windows

  Bianca Rey KELLER WILLIAMS WINTER PARK

  541 W Canton Ave, Winter Park, FL 32789
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  $2,295,000 New Construction

  • 4 Beds
  • 4 Baths
  • 3,005 Sq Ft

  1760 Bryan Ave, Winter Park, FL 32789

  Pre-Construction. To be built. Welcome to an architectural masterpiece that redefines modern luxury and comfort. Situated in the heart of Winter Park, this newly built custom residence by Valdara Homes offers an unparalleled lifestyle of sophistication, comfort, and style. Every detail of this striking two-story home has been meticulously crafted, featuring clean lines, expansive walls of glass,

  Harif Hazera PREMIER SOTHEBY'S INTL. REALTY

  1760 Bryan Ave, Winter Park, FL 32789
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  $3,490,000 New Construction

  • 4 Beds
  • 6 Baths
  • 4,205 Sq Ft

  1910 Glencoe Rd, Winter Park, FL 32789

  Under Construction. Stunning architectural masterpiece built by LUIH homes nestled in the heart of prestigious Winter Park. This brand-new construction embodies the perfect fusion of contemporary design, timeless elegance, and exceptional quality offering 4 bedrooms, 4 full bathrooms, 2 half bathrooms, and over 4,200 square feet of thoughtfully designed luxury living space. As you step through

  Julie Christensen COMPASS FLORIDA LLC

  1910 Glencoe Rd, Winter Park, FL 32789
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  $4,950,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 6,406 Sq Ft

  1660 Palmer Ave, Winter Park, FL 32789

  New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1660 Palmer Ave, Winter Park, FL 32789
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  $1,644,900 New Construction

  • 4 Beds
  • 5 Baths
  • 2,812 Sq Ft

  607 Ellen Dr, Winter Park, FL 32789

  Step into refined living at 607 Ellen Drive, a brand-new two-story modern minimalist home by award-winning Lazarus Winter Park. With 2,812 square feet, this stunning residence offers four bedrooms, a dedicated office, and a luxurious first-floor primary suite. Light oak wide-plank floors and glass stair railings create a sleek, airy aesthetic. Expansive sliding glass doors fully open to a private

  Doug Addeo COMMUNITY REALTY ASSOCIATES

  607 Ellen Dr, Winter Park, FL 32789
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  /11

  $2,119,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 2,964 Sq Ft

  785 N Phelps Ave, Winter Park, FL 32789

  Under Construction. Completion December 2025, Nestled in the heart of Winter Park, this luxurious custom-built home seamlessly blends elegance, functionality, and thoughtful design. Boasting 5 bedrooms, 3.5 bathrooms, and 2,964 sq/ft of unparalleled living space, every detail has been meticulously crafted for modern living. From the moment you step inside, an elegant gallery entrance welcomes you

  Leighton Hope COMPASS FLORIDA LLC

  785 N Phelps Ave, Winter Park, FL 32789
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  /11

  $1,759,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,172 Sq Ft

  1660 Walnut Ave, Winter Park, FL 32789

  Under Construction. Elegant and modern new construction home perfectly situated in beautiful Winter Park. Scheduled for completion in December 2025, this brand new construction home offers a perfect blend of luxury, comfort, and contemporary design. With 4 spacious bedrooms, 3.5 beautifully appointed bathrooms, and 2,172 square feet of meticulously crafted living space, this home is built to

  Julie Christensen COMPASS FLORIDA LLC

  1660 Walnut Ave, Winter Park, FL 32789
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  $545,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,170 Sq Ft

  5255 Seminole Ave, Winter Park, FL 32792

  Price Improvement!!Great opportunity!This stunning 4-bedroom, 3-bath home in one of the most desirable locations—Winter Park! NO HOA! this property features fully permitted updates including Electrical (2024), Plumbing (2024), Water Heater (2024), Roof (2024), and HVAC (2024).Designed with abundant windows for natural light and tile flooring throughout, this home combines style and

  Nohora Gomez COLDWELL BANKER RESIDENTIAL RE

  5255 Seminole Ave, Winter Park, FL 32792
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  $1,800,000 New Construction

  • 5 Beds
  • 4 Baths
  • 3,246 Sq Ft

  2260 Mulbry Dr, Winter Park, FL 32789

  Pre-Construction. To be built. Price Improvement!!! Your Dream Home Is Ready To Be Built!! Pre-Construction Opportunity! Build-to-Suit! Buyers who act now can still pick finishes and style! Build your custom dream home with renowned Konkol Homes in one of Central Florida’s most desirable areas! This nearly 1/4-acre lot is perfectly situated near Baldwin Park, East End Market, Audubon Park K-8,

  Farah Bloom KELLER WILLIAMS WINTER PARK

  2260 Mulbry Dr, Winter Park, FL 32789
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  $8,500,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,564 Sq Ft

  2661 Vía Tuscany, Winter Park, FL 32789

  CALLING HIGHEST AND BEST BY 4/30/2025!! Introducing a Unique, Stunning Modern HomeA groundbreaking architectural masterpiece, this one-of-a-kind residence is built with reinforced concrete, steel, and iron framing, featuring floor-to-ceiling glass walls with no traditional windows. Designed to exceed Florida’s strictest building codes, this home follows commercial-grade

  Prescilla Vazquez PV LUXURY GROUP PA

  2661 Vía Tuscany, Winter Park, FL 32789
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  $1,249,000

  • 4 Beds
  • 3.5 Baths
  • 2,596 Sq Ft

  1835 Lake Sue Dr, Orlando, FL 32803

  Built in 2019 by David Weekley, this Craftsman-style residence blends modern design with timeless character in the heart of Beeman Park. Inside you’re welcomed by an inviting office with French doors, perfect for working from home. Engineered hardwood floors flow throughout the main level, leading to a bright, open concept living space. The kitchen is a chef’s dream with quartz countertops,

  Jenny Lake FANNIE HILLMAN & ASSOCIATES

  1835 Lake Sue Dr, Orlando, FL 32803
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  $795,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,296 Sq Ft

  805 Nottingham St, Orlando, FL 32803

  One or more photo(s) has been virtually staged. Coveted Orwin Manor uniquely positioned between the charm of College Park and the luxury of Park Avenue offers one of its best for you today. Step into a home that feels like it was lifted from a Thomas Kinkade painting—where light dances across tree-lined streets, neighbors wave from their porches, and the mailman strolls by with letters delivered

  Angela Worachek REAL BROKER, LLC

  805 Nottingham St, Orlando, FL 32803
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  $1,250,000 Open Sun 1PM - 5PM

  • 3 Beds
  • 2.5 Baths
  • 2,707 Sq Ft

  3632 Upper Union Rd, Orlando, FL 32814

  Charming and Rare David Weekley Home on Oversized Manor Lot in Baldwin ParkWelcome to 3632 Upper Union Road, Orlando, FL 32814, a beautifully maintained 3-bedroom, 2.5-bath David Weekley Village Home on a rare oversized Manor lot in the heart of Baldwin Park.This 2,707 sqft home exudes classic charm with its Victorian-inspired elevation, inviting full-length front porch, and one of

  Stephen Hachey FLAT FEE MLS REALTY

  3632 Upper Union Rd, Orlando, FL 32814
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  /20

  $308,000

  • 3 Beds
  • 2 Baths
  • 1,076 Sq Ft

  1074 Hamlet Dr, Maitland, FL 32751

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that blends comfort, convenience, and an unbeatable location. From the moment you step inside, you’ll notice the inviting layout featuring a spacious living area filled with natural light and a functional kitchen equipped with newer stainless steel appliances—perfect for everyday living and entertaining alike. The home sits on a

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  1074 Hamlet Dr, Maitland, FL 32751
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  $739,000

  • 3 Beds
  • 2.5 Baths
  • 1,936 Sq Ft

  3074 Stanfield Ave, Orlando, FL 32814

  This Baldwin Park gem features a NEW roof and a prime location! Welcome to this beautiful two-story home located in the heart of highly sought-after Baldwin Park! As you approach this home, you will notice that it has a charming and spacious covered front porch and a fully fenced front yard. Upon entering the home, you will discover that the home has a thoughtfully designed living space. This

  Jenny Lake FANNIE HILLMAN & ASSOCIATES

  3074 Stanfield Ave, Orlando, FL 32814
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  $294,000

  • 3 Beds
  • 2 Baths
  • 1,146 Sq Ft

  1040 Hamlet Dr, Maitland, FL 32751

  This beautifully maintained three-bedroom, two-bath residence features an inviting open floor plan, perfect for both entertaining and everyday living. Recently painted with a fresh interior, the home radiates warmth and brightness throughout. Enjoy modern comforts with a brand-new air conditioning system installed just six months ago, ensuring a cool and comfortable atmosphere year-round. The

  Bianca Botelho RE/MAX ASSURED

  1040 Hamlet Dr, Maitland, FL 32751
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  $1,097,000

  • 3 Beds
  • 3 Baths
  • 2,460 Sq Ft

  1901 Lake Sue Dr, Orlando, FL 32803

  One story, 3-bedroom, 3 bath, RENOVATED home with resort-style backyard and screened lap pool is ready to move in to. It features a modern kitchen with a marble Breakfast bar and marble countertops. An Open floor plan with lots of natural light flowing throughout. The huge primary Bedroom suite with sitting area and private bath, his and hers closets, opens to the screened pool and spa. A

  Pamela Stewart REALCOM REAL ESTATE SERVICES INC

  1901 Lake Sue Dr, Orlando, FL 32803
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  $575,000

  • 3 Beds
  • 2 Baths
  • 1,538 Sq Ft

  113 Gem Lake Dr, Maitland, FL 32751

  Must remodel this 1939 home that was moved from Park Avenue many years ago but now rests in Maitland bordering Winter Park. This home is a piece of history with character but in need of some TLC. Beautifully arched high ceiling along with a fireplace in the formal living room. The Florida room is surrounded by glass sliding doors that open to a wooden patio with French doors, countless windows,

  Darryl Donkel HOME WISE REALTY GROUP, INC.

  113 Gem Lake Dr, Maitland, FL 32751

Showing Results 201 - 228, Page 6 of 6