Winter Park, FL Houses for Sale

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  $899,000

  • 3 Beds
  • 2.5 Baths
  • 1,314 Sq Ft

  251 Glenridge Way, Winter Park, FL 32789

  The true value of this property lies in its expansive 10,675 sq ft lot, nestled among multi-million dollar homes. Whether you're looking to build your dream home or expand upon the existing structure, this is a rare opportunity in a highly sought-after location. A full set of building plans are attached to this listing as well as survey.The existing home is a charming 3-bedroom, 3.5-bath

  Russ Razzani RAZZANI INTERNATIONAL REALTY

  251 Glenridge Way, Winter Park, FL 32789
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  $999,000

  • 3 Beds
  • 1 Bath
  • 1,045 Sq Ft

  674 W Comstock Ave, Winter Park, FL 32789

  Beautiful Winter Park historic home that's been totally gutted and renovated. Comes complete with new doors, windows, AC, roof, water heater and gas furnace. Impeccable landscaping as well as larger than usual lot. The home is in short walking distance to all of the amenities that Winter Park brings. Close to the community center. Close to downtown Winter Park. Close to the New England Ave

  Frank Baker, Jr KELLER WILLIAMS WINTER PARK

  674 W Comstock Ave, Winter Park, FL 32789
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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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  $3,895,000 New Construction

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

  1820 Glencoe Rd, Winter Park, FL 32789

  Welcome to your dream home—a masterfully designed, Dutch West Indies-inspired custom residence that blends timeless elegance with modern luxury. Built by FG Schaub Custom Homes, this home features five bedrooms, five full bathrooms, two half bathrooms, and a dedicated home office, all thoughtfully designed for comfort and sophistication within 4,055sqft. of living space.Stepping into the

  Laura Earl CORCORAN PREMIER REALTY

  1820 Glencoe Rd, Winter Park, FL 32789
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  $1,575,000 New Construction

  • 5 Beds
  • 4 Baths
  • 2,895 Sq Ft

  1473 Berkshire Ave, Winter Park, FL 32789

  Under Construction. Brand-New 2025 Mediterranean Luxury in Historic Winter ParkIntroducing 1473 Berkshire Avenue — a just-completed luxury residence nestled on one of Winter Park’s most peaceful, tree-lined, and century-old streets. This two-story Mediterranean masterpiece delivers the perfect blend of timeless architecture and contemporary design, offering 5 bedrooms, 4 bathrooms, and nearly

  Milena Fernandes GOLDEN GROUP REALTY LLC

  1473 Berkshire Ave, Winter Park, FL 32789
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  $1,695,000 Open Sat 12PM - 2PM

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

  1780 Mizell Ave, Winter Park, FL 32789

  Experience the height of modern luxury in this newly constructed home, masterfully designed by esteemed architect Gary Hancock and ideally in the heart of Winter Park. Offering nearly 2,800 square feet of refined living space, this four-bedroom, four-bath residence seamlessly blends timeless design with high-end finishes, creating an elevated lifestyle. Enter to soaring 10-foot ceilings on both

  Megan Byers PREMIER SOTHEBY'S INTL. REALTY

  1780 Mizell Ave, Winter Park, FL 32789
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  $1,200,000 New Construction

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

  1807 Magnolia Ave, Winter Park, FL 32789

  Under Construction. Scheduled completion March 2026. New construction in the City of Winter Park! There is still time to make personalized finish selections. This deep 56 x 157 lot is Winter Park's best kept secret, located in a quiet pocket of 32789. This property is centrally located, less than 10 minutes to Park Ave, and zoned for Orange County schools: Dommerich Elementary, Maitland Middle,

  Kristen Hamilton LOMBARDO TEAM REAL ESTATE LLC

  1807 Magnolia Ave, Winter Park, FL 32789
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  $2,590,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,138 Sq Ft

  185 Sylvan Blvd, Winter Park, FL 32789

  Under Construction. Brand-new, meticulously crafted residence built by renowned builder LUIH Homes offering 3,138 square feet of thoughtfully designed living space. As you arrive, the home's stunning architectural facade and detached two-car garage make a striking first impression. Inside, every detail has been carefully curated to offer both sophistication and functionality. Soaring ceilings and

  Christopher Christensen COMPASS FLORIDA LLC

  185 Sylvan Blvd, 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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  $4,100,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 4,782 Sq Ft

  1782 Pine Ave, Winter Park, FL 32789

  Under Construction. UNDER CONSTURCTION.....Step into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiece in the heart of City of Winter Park. Exquisite Interior Features that are offered starts with entering the grand foyer with 10ft high ceiling and the flex room and formal dining to your left and

  Prentice Williams EXP REALTY LLC

  1782 Pine Ave, Winter Park, FL 32789
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  $1,775,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,950 Sq Ft

  1702 Arbor Park Dr, Winter Park, FL 32789

  Under Construction. Modern elegance and timeless sophistication define 1702 Arbor Park Dr, a meticulously crafted new construction home in the heart of Winter Park, FL. Spanning 2,950 square feet, this 4-bedroom, 3.5-bathroom residence also features a dedicated office and a conditioned attic that can serve as a fifth bedroom, offering flexible living space to meet various needs. Designed for

  Christopher Christensen COMPASS FLORIDA LLC

  1702 Arbor Park Dr, Winter Park, FL 32789
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  $5,200,000 New Construction

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

  1660 Palmer Ave, Winter Park, FL 32789

  Experience refined luxury in this newly constructed 2024 Hamptons-style residence, a seamless blend of elegance and modern sophistication. A remote-operated gated entrance opens to a grand circular driveway and private motor court, setting the stage for this exceptional estate. The two-story foyer impresses with a glass-paneled staircase that wraps around a temperature-controlled wine room and a

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1660 Palmer Ave, Winter Park, FL 32789
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  $1,664,900 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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  $2,389,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 4,506 Sq Ft

  2412 Chantilly Ave, Winter Park, FL 32789

  An architectural tour de force in the heart of Winter Park. Designed by a premier builder of boutique homes and crafted with no detail spared, this 5-bedroom, 6.5-bathroom estate offers over 4,500 square feet of bold yet elegant living. A soaring 28-foot foyer sets the tone with dramatic scale, introducing the home through double-height French doors into expansive interiors showcasing

  Ahmad Hassan COMPASS FLORIDA LLC

  2412 Chantilly Ave, Winter Park, FL 32789
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  $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 September 2025, Nestled in the heart of Winter Park, this luxurious custom-built home seamlessly blends elegance, functionality, and thoughtful design. Boasting 5 bedrooms, 4.5 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

  Leighton Hope COMPASS FLORIDA LLC

  785 N Phelps Ave, Winter Park, FL 32789
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  $1,599,900 New Construction

  • 5 Beds
  • 4 Baths
  • 3,312 Sq Ft

  1417 Miller Ave, Winter Park, FL 32789

  Under Construction. New construction, single family home from FG Schaub Custom Homes, featuring five bedrooms and four bathrooms with custom curated finishes within a 3312sqft., open floor plan. Approaching the home, you'll notice the gorgeous Transitional design and spacious front porch with tongue and groove ceilings. Upon entering, you will be treated to extensive natural light, hardwood

  Laura Earl CORCORAN PREMIER REALTY

  1417 Miller 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 is currently under construction 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,

  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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  $699,900

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft

  2338 Tuscarora Trail, Maitland, FL 32751

  With over $60k in upgrades, this beautiful 4-bedroom, 2-bathroom lakeside retreat is tucked away in the highly sought-after Dommerich Hills community! Enjoy living next to the tranquil waters of Lake Waumpi and a peaceful conservation area, offering a rare blend of natural beauty and everyday comfort. Surrounded by mature trees and set on over a 1-acre lot, the backyard is a true sanctuary,

  Megan Hedrick Mark Spain Real Estate

  2338 Tuscarora Trail, Maitland, FL 32751
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  $775,000

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

  3074 Stanfield Ave, Orlando, FL 32814

  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 light-filled home blends charm and functionality. Step inside to

  Jenny Lake FANNIE HILLMAN & ASSOCIATES

  3074 Stanfield Ave, Orlando, FL 32814
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  $1,550,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,550 Sq Ft

  2781 Stanfield Ave, Orlando, FL 32814

  This beautifully updated 3 bedroom, 2.5 bath one-story David Weekley “Brames” model with coastal elevation offers refined design, spacious living, and a rare level of luxury in the highly sought-after Baldwin Park community. With a desirable split floorplan and custom upgrades throughout, this turnkey residence delivers effortless living and elevated style in one of Orlando’s premier

  Erin Woodward WEICHERT REALTORS HALLMARK PROPERTIES

  2781 Stanfield Ave, Orlando, FL 32814
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  $669,900

  • 3 Beds
  • 2 Baths
  • 1,938 Sq Ft

  489 Penny Ln, Maitland, FL 32751

  Presenting 489 Penny Lane located in the sought after Gated Community known as Brittany Gardens. Upon arrival you will be impressed with the front yard garden featuring landscape lighting, flagstone accents, lush landscaping and a paver driveway. The inviting front porch offers a welcoming and visually appealing space where you will transition from outdoors into modern luxury in this beautifully

  Erin Tompkins COLDWELL BANKER RESIDENTIAL RE

  489 Penny Ln, Maitland, FL 32751
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  $799,000

  • 4 Beds
  • 2.5 Baths
  • 3,377 Sq Ft

  1621 Sunnyside Dr, Maitland, FL 32751

  Motivated seller. Bring me an offer. Amazing home on a double lot that can be sub-divided. this is an opportunity to live in one of the best neighborhoods in the Winter Park / Maitland area. The true value of this property lies in its expansive 100x135 sized lot, nestled among multi-million dollar homes. Whether you're looking to build your dream home or expand upon the existing structure, this

  Troy Eggleston OUTLET REALTY

  1621 Sunnyside Dr, Maitland, FL 32751
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  $709,990

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft

  1655 Sunnyside Dr, Maitland, FL 32751

  Welcome to this one-of-a-kind vintage charmer in the heart of Maitland, Florida! Nestled on a beautifully landscaped corner lot, this 3-bedroom, 2-bathroom historic cottage offers 1,418 square feet of thoughtfully designed living space. Just minutes from downtown Maitland and the vibrant energy of Winter Park, you’ll love the perfect blend of convenience and character this home

  Joseph Sipp KELLER WILLIAMS WINTER PARK

  1655 Sunnyside Dr, Maitland, FL 32751
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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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  $1,350,000

  • 3 Beds
  • 2.5 Baths
  • 2,960 Sq Ft

  3308 Middlesex Rd, Orlando, FL 32803

  This breathtaking Spanish-style home, winner of First Place for Design by the American Society of Interior Designers in 2020, is a true masterpiece. Designed by HGTV Designer of the Year John McClain, it blends modern luxury with timeless charm.The magazine-worthy kitchen—featured on Southern Living’s website—boasting Sherwin William's 2021 color of the year, the custom Urbane Bronze

  Julie Bettosini STOCKWORTH REALTY GROUP

  3308 Middlesex Rd, 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
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  $409,900

  • 3 Beds
  • 2 Baths
  • 1,885 Sq Ft

  2625 Queen Mary Place, Maitland, FL 32751

  Auction Property. Located in desirable Brittany Gardens, this home offers spacious living areas and a smart, open floorplan — perfect for customization and renovation. Step inside to find a large great room, ideal for entertaining. The generously sized master suite features a luxurious bathroom with a soaking tub, separate shower enclosure, and dual vanities. Additional bedrooms are

  Wade Stafford ALL FLORIDA PROPERTY GROUP,INC

  2625 Queen Mary Place, Maitland, FL 32751

Showing Results 201 - 232, Page 6 of 6