Homes for Sale near Winter Park High

• 

  

  

  /90

  $2,875,000

  • 8 Beds
  • 6 Baths
  • 7,000 Sq Ft

  1860 Via Contessa, Winter Park, FL 32789

  Step into your dream home in Winter Park! This stunning 7,000 SF residence, nestled on a peaceful street in the coveted Vias neighborhood, offers ample space across three levels, making it an ideal choice for those who crave both room to spread out and a welcoming atmosphere. Gorgeous hardwood floors flow throughout the main living areas, enhancing the home's inviting, warm ambiance. The

  Sylvester Harding SIERRA REALTY GROUP LLC

  1860 Via Contessa, Winter Park, FL 32789
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  /41

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 2,447 Sq Ft

  2612 Lafayette Ave, Winter Park, FL 32789

  ***SELLER IS OFFERING $10,000 IN CONCESSIONS TOWARDS CLOSING COSTS***This exquisite residence offers sophistication and comfort without HOA constraints. Its fresh stucco facade and welcoming patio lead to a beautifully landscaped oasis. Inside, recessed lighting illuminates a captivating accent wall and a step-down entertainment area, perfect for relaxation or gatherings. The kitchen features

  Maoline Herrera EXP REALTY LLC

  2612 Lafayette Ave, Winter Park, FL 32789
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  /6

  $99,000

  • Studio
  • 1 Bath
  • 537 Sq Ft

  3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792

  Attention investors! Take a look at this great opportunity to purchase a Cozy Condo located in Winter Park, FL. This studio condo features beautiful tile floors and lots of closet space. First-floor unit with open patio. Minutes away from Downtown Winter Park, expressway, downtown Orlando, Full Sail, and the University of Central Florida. This community offers a pool, tennis court, and clubhouse.

  Lynda Cheros OAKSTRAND REALTY

  3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792
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  /6

  $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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  /15

  $425,000

  • Land
  • 0.11 Acre
  • $3,863,636 per Acre

  786 W Canton Ave, Winter Park, FL 32789

  Incredible opportunity for the right family. This is a 49x96 Perfectly high and dry lot with a tree to shade your backyard. Nestled in the highly sought after City of Winter Park amongst million dollar homes. LOCATION LOCATION LOCATION! A perfect home site for your future custom dwelling. Bring your imagination creativity and builder to take a look. What a Winter Park sweet spot. Lots in this

  Laurie Cash Cain CHARLES RUTENBERG REALTY ORLANDO

  786 W Canton Ave, Winter Park, FL 32789
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  /20

  $220,000

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft

  3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792

  This unit was restored, with new kitchen cabinets, new ceramic tile in kitchen, living room, dining room and 2ndbathroom. It has been impeccably maintained. Walking distance from Full Sail and only 6.9 miles to UCF.Spacious bedrooms and baths and very comfortable layout. Lovely screened patio off living room. Complexoffers pool, and club house. A/C unit is brand new, installed on

  Manny Celi YOUNG REAL ESTATE

  3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792
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  /11

  $198,000

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft

  3060 George Mason Ave Unit 12, Winter Park, FL 32792

  Welcome to your new home in Winter Park!Completely remodeled unit with luxury finishes, ceramic floors, modern bathrooms, brand new kitchen with steel appliances and a nice quartz counter. Community amenities include pool, tennis and playground. Great Schools - zoned for Winter Park HS. Just minutes to Full Sail, UCF & Valencia. Don’t miss out on this gem!

  Adriana Sanchez AGENT TRUST REALTY CORPORATION

  3060 George Mason Ave Unit 12, Winter Park, FL 32792
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  /2

  $415,000

  • Land
  • 4.62 Acres
  • $89,827 per Acre

  2210 N Goldenrod Rd, Azalea Park, FL 32807

  This is a large wooded 4.66 acre plot with 334' frontage on N. Goldenrod Road. Due to some of the property being wet, flood insurance is required. 1.65 acre is dry and developable.

  Michelle Sanderson CHARLES RUTENBERG REALTY ORLANDO

  2210 N Goldenrod Rd, Azalea Park, FL 32807
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  /19

  $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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  /27

  $700,000

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft

  865 S Pennsylvania Ave, Winter Park, FL 32789

  LOCATION, LOCATION, LOCATION...Desirable Winter Park "College Quarter" Historic District...Come take a tour of this wonderfully updated Bungalow with lots of windows for natural light, original hardwood floors, beautiful crown molding, and high ceilings. Did I mention the location, Walk to Park Ave, Rollins College, Hannibal Square, Mead Gardens, and Lake Virginia. Looking to "House Hack" then

  Jose Vega LPT REALTY, LLC

  865 S Pennsylvania Ave, Winter Park, FL 32789
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  /2

  $2,450,000

  • 5 Beds
  • 5.5 Baths
  • 4,010 Sq Ft

  1771 Taylor Ave, Winter Park, FL 32789

  Custom Winter Park home completed in 2019 by FG Schaub Custom Home Builder. Contemporary Florida living awaits in this newly built home, boasting a spacious open floor plan spanning over 4,000 square feet with five bedrooms and five-and-a-half baths. Delight in the stunning gourmet kitchen, gas cooktop, oversized island and an extended walk-in pantry with cabinets. Distinctive features include

  Michelle Hochfelder PREMIER SOTHEBY'S INTL. REALTY

  1771 Taylor Ave, Winter Park, FL 32789
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  /2

  $2,995,000

  • Land
  • 3.45 Acres
  • $868,116 per Acre

  1427 N Semoran Blvd, Orlando, FL 32807

  Prime location, 3.45 acres on SR 436 with 600' frontage. Current zoning is PD-C (Planned development with most C1 uses). Possible uses are office, retail or mixed uses, Medical (excluding drug and alcohol rehabs), restaurants. Most C1 uses permitted with some exceptions. Allowable 45,000 sf buildout. See the Land Use table attached for extensive allowable uses in highlights.0.72 acres wetland

  Shahrzad Shamsaee SHAHRZAD REALTY LLC

  1427 N Semoran Blvd, Orlando, FL 32807
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  /6

  $170,000

  • Land
  • 0.18 Acre
  • $944,444 per Acre

  861 High St, Orlando, FL 32803

  Great location with great schools! Corner lot, Zoned R-2! Demolition was completed on prior structure. Survey is available. Do not miss out on this excellent opportunity!

  Terry Horne CHAMPIONSGATE REALTY

  861 High St, Orlando, FL 32803
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  /2

  $419,900

  • 3 Beds
  • 2 Baths
  • 1,405 Sq Ft

  616 Ellendale Dr, Winter Park, FL 32792

  Desirable Winter Park Estates - close to everything! Beautifully updated 3 Bedroom 2 Bath POOL home which is located in a highly desirable school district! Updated Contemporary Kitchen has newer Cabinetry, newer Stainless-Steel appliances, and Granite countertops which connect with the open Living room. Dining area extends to the generous size Family room - Ideal for Entertaining. The home

  David Ruiz CENTRAL REALTY

  616 Ellendale Dr, Winter Park, FL 32792
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  /2

  $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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  /2

  $499,000

  • Land
  • 0.13 Acre
  • $3,838,462 per Acre

  621 Symonds Ave, Winter Park, FL 32789

  Great opportunity for a R-2 lot in heart of downtown Winter Park - opportunity to purchase adjacent lot at 631 Symonds and combine

  Emily Williams FANNIE HILLMAN & ASSOCIATES

  621 Symonds Ave, Winter Park, FL 32789
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  /2

  $499,000

  • Land
  • 0.13 Acre
  • $3,838,462 per Acre

  631 Symonds Ave, Winter Park, FL 32789

  Great R-2 lot in the heart of downtown Winter Park - lot next door 621 Symonds also available for purchase and opportunity to combine.

  Emily Williams FANNIE HILLMAN & ASSOCIATES

  631 Symonds Ave, Winter Park, FL 32789
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  /2

  $435,000

  • Land
  • 1.33 Acres
  • $327,068 per Acre

  9318 Trevarthon Rd, Orlando, FL 32817

  Rare opportunity to own 6.35 acres along the Econlockahatchee River with all 4 lots. Each lot is price separately. This property is close to Valencia Community College - East, University of Central Florida, 408 and 417. Call today for more information.

  Cathy Marino CATHY S. MARINO REALTY, INC.

  9318 Trevarthon Rd, Orlando, FL 32817
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  /2

  $372,000

  • Land
  • 1.53 Acres
  • $243,137 per Acre

  9316 Trevarthon Rd, Orlando, FL 32817

  Rare opportunity to own 6.35 acres with all 4 lots (each lot price separately). This location is close to Valencia Community College, University of Central Fla., 408 and 417. Call today for more information.

  Cathy Marino CATHY S. MARINO REALTY, INC.

  9316 Trevarthon Rd, Orlando, FL 32817
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  /2

  $508,000

  • Land
  • 1.79 Acres
  • $283,799 per Acre

  9314 Trevarthon Rd, Orlando, FL 32817

  Rare opportunity to own 4 contiguous lots for a total of 6.35 acres. Eash lot is priced separately. The total for all 4 lots is 1.8 million. Located on the shores of the Econlockahatcee River. Location is close to Valencia Community College East Campus, University of Central Florida, 408 and 417. Please call for additional information.

  Cathy Marino CATHY S. MARINO REALTY, INC.

  9314 Trevarthon Rd, Orlando, FL 32817
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  /2

  $485,000

  • Land
  • 1.7 Acres
  • $285,294 per Acre

  9312 Trevarthon Rd, Orlando, FL 32817

  Opportunity to own 6.35 acres (all 4 lots) along the Econlockahatee River. This property is close to the 408, 417, Valencia Community College and UCF. Seller is selling all 4 lots together. Call for more information.

  Cathy Marino CATHY S. MARINO REALTY, INC.

  9312 Trevarthon Rd, Orlando, FL 32817
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  /25

  $512,100 New Construction

  • 2 Beds
  • 2.5 Baths
  • 1,390 Sq Ft

  905 Lake Baldwin Ln, Orlando, FL 32803

  Under Construction. Welcome to the Summerlyn on Homesite 2 - Welcome to a residence where modern design meets timeless elegance. This beautifully crafted 2-bedroom townhome with loft and private garage, built by award-winning David Weekley Homes, offers a sophisticated retreat just steps from the charm of Baldwin Park. The thoughtfully designed floor plan blends comfort and style, with seamless

  Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  905 Lake Baldwin Ln, Orlando, FL 32803
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  /12

  $4,750,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,211 Sq Ft

  1525 Granville Dr, Winter Park, FL 32789

  Under Construction. Just steps from the boutiques and fine dining of Park Avenue, this brand-new bespoke estate by acclaimed builder Vimaro Homes delivers a rare combination of architectural sophistication and thoughtful design. Perfectly positioned on an oversized 0.34-acre lot, the residence encompasses over 5,200 square feet of refined living space, crafted with the finest materials and an

  Julie Christensen COMPASS FLORIDA LLC

  1525 Granville Dr, Winter Park, FL 32789
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  /22

  $606,616 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,163 Sq Ft

  1824 Liphock Alley, Orlando, FL 32803

  First-floor Extra Suite with private bath for guests. Open kitchen, dining area & great room create central living space. Waterfall-edge central island offers prep & dining space in kitchen. Primary suite with detailed ceiling adds character. Primary spa bath with dual sinks & sleek finishes. Upstairs laundry room near bedrooms adds convenience.

  

  K. Hovnanian Homes

  Builder

  1824 Liphock Alley, Orlando, FL 32803
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  /44

  $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 elegance and artisan craftsmanship. In one of Winter Park’s desirable residential corridors, warmth and beauty abound in this four-bedroom, six-bath residence spanning 3,720 square feet or air conditioned and 4,535 square feet total under

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  702 Via Bella, Winter Park, FL 32789
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  /11

  $614,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,932 Sq Ft

  4301 Roush Ave, Orlando, FL 32803

  Under Construction. Stunning 3-bedroom, 2.5-bath townhome on a desirable corner homesite, built by award-winning David Weekley Homes. This home offers an open layout with expansive windows, abundant natural light, and a versatile loft. The spacious owner's retreat features a large walk in closet and spa-like bath. Enjoy the convenience of being just minutes from Baldwin Park amenities including

  Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  4301 Roush Ave, Orlando, FL 32803
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  /15

  $599,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,560 Sq Ft

  2566 Cavanaugh Dr, Orlando, FL 32817

  Move-In Ready! Discover comfort and style in this beautifully designed Newcastle plan featuring 4 bedrooms, 2.5 baths, and a 2-car garage. Soaring 9'4" ceilings on the first floor create an airy, open-concept living space with tile flooring through the 1st floor main living areas, and window blinds throughout for added privacy. The versatile front living room is perfect as a home office or den,

  Stephen Wood LANDSEA HOMES OF FL, LLC

  2566 Cavanaugh Dr, Orlando, FL 32817
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  /18

  $3,950,000 New Construction

  • 5 Beds
  • 5 Baths
  • 3,183 Sq Ft

  850 Juanita Rael, Winter Park, FL 32789

  Pre-Construction. To be built. This is that house. Location, Architecture and Layout. Designed on one level on an oversized corner lot on the North side of Winter Park which allows an ease of in and out on a quiet and lovely location. This mid-century Frank Lloyd Wright inspired home could be one of Phil Kean’s best work yet, and certainly a unique addition to the Old Winter Park landscape.

  Brad Grosberg PHIL KEAN REAL ESTATE LLC

  850 Juanita Rael, Winter Park, FL 32789
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  /3

  $1,390,000 New Construction

  • 5 Beds
  • 4 Baths
  • 3,465 Sq Ft

  1505 Cole Rd, Orlando, FL 32803

  Under Construction. This new David Weekley home in Audubon Park combines easy elegance with the streamlined versatility to adapt to your family’s lifestyle changes through the years. Cherish your relaxing sunsets and breezy weekends from the shaded bliss of your covered front porch, and backyard lanai. Your awe-inspiring Owner's Retreat provides a glamorous way to begin and end each day with a

  Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  1505 Cole Rd, Orlando, FL 32803
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  /19

  $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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  /35

  $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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  /2

  $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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  /13

  $1,800,000 New Construction

  • 5 Beds
  • 4 Baths
  • 3,723 Sq Ft

  1201 Tanager Dr, Orlando, FL 32803

  Under Construction. Stunning architectural masterpiece by renowned builder LUIH Homes, perfectly positioned in the highly sought-after Audubon Park neighborhood. This exceptional residence spans nearly 3,800 square feet of expertly designed living space, set on a generous 0.26-acre lot. From the moment you arrive, the home commands attention with a bold double-door entry and striking curb appeal

  Christopher Christensen COMPASS FLORIDA LLC

  1201 Tanager Dr, Orlando, FL 32803
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  /29

  $429,500 New Construction

  • 3 Beds
  • 2 Baths
  • 1,588 Sq Ft

  726 Eldridge St, Orlando, FL 32803

  Don’t miss this incredible opportunity to own a stunning BRAND-NEW 3-bedroom, 2-bathroom home in the highly desirable Lake Barton Shores community—just minutes from BALDWIN PARK! This beautifully crafted residence offers a modern open-concept layout, energy-efficient systems, and premium finishes throughout, creating the perfect blend of style and functionality. Nestled in a fast-growing area,

  Emidio Dinardo CENTURY 21 WOLF'S CROSSING REALTY

  726 Eldridge St, Orlando, FL 32803
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  /61

  $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 Open Sat 11AM - 1PM

  • 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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  /59

  $1,599,900 Open Sat 12PM - 2PM

  • 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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  /25

  $619,800 New Construction

  • 6 Beds
  • 4 Baths
  • 2,952 Sq Ft

  2420 Gresham Dr, Orlando, FL 32807

  New house built in 2023, Beautiful house, built for a large family, 6 bedrooms and 4 bathrooms, the kitchen, dining room and living room have the open concept. The kitchen has a super large counter for those who love to cook and value space, the appliances are of a unique style, Two master bedrooms, 9.4-foot ceiling, Bright and open Family Room, Office Room, Bonus room, the whole driveway has

  Pedro Leon ATIDOT INVESTMENT, LLC

  2420 Gresham Dr, Orlando, FL 32807
• 

  

  /16

  $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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  /49

  $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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