4-Bedroom Homes for Sale in Winter Park, FL

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  $3,499,500

  • 4 Beds
  • 5.5 Baths
  • 4,635 Sq Ft

  1391 Richmond Rd, Winter Park, FL 32789

  Welcome to 1391 Richmond Road, a true work of art and a surreal living experience now on the market. The most discerning buyer will fall in love with the optimal location, an unusually private lot right in the heart of Winter Park, a short stroll to Park Avenue along the stunning shores of Lake Virginia. This handcrafted Georgian style home, designed to emulate New York City townhouse living was

  Julie Bettosini STOCKWORTH REALTY GROUP

  1391 Richmond Rd, Winter Park, FL 32789
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  $539,500

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft

  8162 Lazy Bear Ln, Winter Park, FL 32792

  *20K PRICE DROP* 4 bedroom, 2 bath home set on a perfectly manicured 1/4 acre corner lot, located in the new Winter Park gated community Enclave at Aloma. Open floor plan is enhanced by the Hardwood Floors throughout living areas, volume ceilings, light and bright kitchen, family room with lots of windows, and slider that opens onto the spacious lanai. Energy efficient double pane insulated

  Elio Serpa AUTHENTIC REAL ESTATE TEAM

  8162 Lazy Bear Ln, Winter Park, FL 32792
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  $409,900

  • 4 Beds
  • 4 Baths
  • 1,934 Sq Ft

  3128 Patel Dr, Winter Park, FL 32792

  Don't miss this income producing duplex just minutes from University Ave and the UCF area! The seller has just completed replacing the roof of this duplex. The separate units are 2 bedroom, 2 bath on each side and include ceramic tile/laminate flooring, spacious living room, kitchen with appliances, spacious closets, ceiling fans, washer/dryer hookups, and spacious fenced back

  Keith Race FUSILIER MANAGEMENT GROUP

  3128 Patel Dr, Winter Park, FL 32792
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  $550,000

  • 4 Beds
  • 3 Baths
  • 1,805 Sq Ft

  2627 Ambergate Rd, Winter Park, FL 32792

  This beautiful and remodeled home is turnkey and ready to move in, fully furnished.Investors -- You will love the cash flow upside with this property.Updated Roof, AC, Exterior Paint, Patio, Garage, Driveway, Fence, Sprinkler System, Lighting, Flooring, Kitchen, and much more.You will enjoy entertaining your guests with this large saltwater pool with cabana, as well as yard space for

  Ryan Minadie COLDWELL BANKER RESIDENTIAL RE

  2627 Ambergate Rd, Winter Park, FL 32792
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  $795,000

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft

  1740 Anzle Ave, Winter Park, FL 32789

  PROPERTY AS-IS - DEMO AND NEW-BUILD PLANS APPROVED*Property with all demo permits and build plans approved ready for a new build*Nestled in the heart of Winter Park’s coveted 32789 ZIP code, this stunning new possibility offers the epitome of luxury living in one of Central Florida’s most coveted neighborhoods. The current structure has been approved for demolition so you

  Felipe Robayo GOYAL & DECOSTER REALTY

  1740 Anzle Ave, Winter Park, FL 32789
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  $4,650,000 New Construction

  • 4 Beds
  • 5.5 Baths
  • 3,720 Sq Ft

  702 Via Bella, Winter Park, FL 32789

  Welcome to 702 Via Bella, an impressive 2025 English Cottage Estate by Floridian Custom Homes that captures the essence of timeless architecture exemplifying transitional elegance and true artisan craftsmanship. Located in one of Winter Park’s most desirable residential corridors, warmth & beauty abound in this 4 bedroom, 6 bath residence spanning 3,720 sf conditioned and 4,535 sf total under

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  702 Via Bella, Winter Park, FL 32789
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  $888,050 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,662 Sq Ft

  Lot #21 Karolina Ave, Winter Park, FL 32789

  Pre-Construction. To be built. Step into a life where charm meets convenience in the heart of Winter Park. This brand-new 4-bedroom, 3.5-bath, 2,662 sq. ft. home is situated on a 6,748 sq. ft. lot and is a thoughtfully designed masterpiece, blending elegant country charm with the comfort and functionality today’s homeowners crave.One of three consecutive custom builds — each with its own

  Laura Hope COMPASS FLORIDA LLC

  Lot #21 Karolina Ave, Winter Park, FL 32789
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  $864,020 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,662 Sq Ft

  1835 Karolina Ave, Winter Park, FL 32789

  Pre-Construction. To be built. Experience the best of Winter Park living at 1835 Karolina Ave — one of only three brand-new, custom-built homes on this highly coveted block. This beautiful 4-bedroom, 3.5-bath Prairie elevation home offers 2,662 sq. ft. of thoughtfully designed living space on a 6,748 sq. ft. lot. It combines distinctive architectural character with a prime location—only 6 minutes

  Laura Hope COMPASS FLORIDA LLC

  1835 Karolina 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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  $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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  $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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  $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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  $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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  $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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  $889,000 Open Sun 12:01PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  2514 Tuscarora Trail, Maitland, FL 32751

  Lakefront Dommerich pool home in one of Central Florida’s most coveted school zones! This 4-bedroom, 2.5-bath beauty offers nearly 3,000 sq. ft. of spacious living, zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High. Enjoy a private pool, stunning lake views, and plenty of space to gather, entertain, and relax—right in the heart of one of Maitland’s most desirable

  TOM NOELKE EXP REALTY LLC

  2514 Tuscarora Trail, Maitland, FL 32751

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