Winter Park, FL Homes for Sale

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  $995,000

  • 2 Beds
  • 1.5 Baths
  • 1,374 Sq Ft

  2260 Hawick Ln, Winter Park, FL 32792

  This Winter Park investment opportunity is prime for Developers, Builders, & Investors for redevelopment. The Hawick Lane property is currently vacant as the home and trees are recently demo'ed. The future development of three (3) fee simple single family lots (50’ wide) is the highest and best use of this land. The total land area is approximately 19,698sf. (150ft street frontage by 140ft lot

  Michael Rasmussen DAVEN REAL ESTATE INC

  2260 Hawick Ln, Winter Park, FL 32792
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  $215,000

  • 1 Bed
  • 1 Bath
  • 772 Sq Ft

  700 Melrose Ave Unit K32, Winter Park, FL 32789

  Discover Winter Park Gardens, an exclusive 55+ community nestled in the heart of historic Winter Park! Welcome to your private oasis at this one-bedroom, one-bathroom condo on the tranquil third floor, accessible by elevator. Enjoy sweeping views of the pool and beautifully landscaped courtyard from your unit, which includes a spacious storage closet in the foyer. Convenience is key with elevator

  Erica Diltz BALDWIN PARK REALTY LLC

  700 Melrose Ave Unit K32, Winter Park, FL 32789
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  $179,900

  • 3 Beds
  • 2 Baths

  7340 Daniel Webster Dr, Winter Park, FL 32792

  This is a 3 bedroom and 2 bathroom condo. This condo has had everything replaced. Don't miss out on this opportunity. Call listing agent today for more information and to schedule a showing.

  Robert Castro RE/MAX - City Centre Realty

  7340 Daniel Webster Dr, Winter Park, FL 32792
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  /35

  $306,900

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft

  2384 Sun Valley Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to your dream home in beautiful Winter Park, Florida! This charming 3-bedroom, 2-bath corner unit is just half a mile from Casselberry Commons, offering shopping, dining, and everyday convenience right at your doorstep.Enjoy peace of mind with a new roof (2023), new thermostat and fan (2024), and updated AC ducts and insulation

  Yvette Hernandez THE REALTY EXPERIENCE POWERED BY LRR

  2384 Sun Valley Cir, Winter Park, FL 32792
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  $449,000

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  311 E Morse Blvd Unit 7-2, Winter Park, FL 32789

  Enjoy sunrise views over Lake Osceola from this Whispering Waters jewel box located just steps from Park Avenue. This fully renovated, one-bedroom, one-bathroom condo offers 900 ft2 of single-story, ground-floor, corner-unit living. The 2018 full renovation was extensive and included new electrical re-wiring and plumbing. The scope of the renovation extended to creating new conditioned space,

  Padgett McCormick KELLY PRICE & COMPANY LLC

  311 E Morse Blvd Unit 7-2, Winter Park, FL 32789
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  $2,070,000

  • 6 Beds
  • 3.5 Baths
  • 3,554 Sq Ft

  2234 Via Luna, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. NEW IMPROVED PRICING! Newly Renovated Partially Furnished Home in the Beautiful Via’s of Winter Park! Privately located on a large wrap around corner lot. It is meticulously maintained with eye-catching curb appeal with mature magnolia trees and beautiful landscaping with newly installed lighting to illuminate at night. This stunning 6 bedroom and

  Iram Hashmi LOKATION

  2234 Via Luna, Winter Park, FL 32789
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  /90

  $2,750,000 Open Sat 1PM - 3PM

  • 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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  $625,000

  • 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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  $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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  $429,900

  • 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 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 yard.The property is currently rented on a month to month basis at

  Keith Race FUSILIER MANAGEMENT GROUP

  3128 Patel Dr, Winter Park, FL 32792
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  /25

  $284,900

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft

  2335 Inagua Way, Winter Park, FL 32792

  Rare opportunity in beautiful Winter Park - Move in ready 3 bed 2 bath townhome for under $300,000. Super low HOA at only $92/month. Spacious split plan with new roof, newer AC, new carpet in bedrooms, freshly painted, tile, inside laundry, atrium off living room and open floor plan. Patio with storage room and shed. Front entrance & parking area with beautiful pavers. Townhome is on

  Marion McGrath ABSOLUTE REALTY GROUP, LLC

  2335 Inagua Way, 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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  $370,000

  • 3 Beds
  • 2 Baths
  • 1,283 Sq Ft

  780 Baffie Ave, Winter Park, FL 32789

  Great opportunity to live in Winter Park in the Dubsdread Golf Community. This 3 bedroom, 2 bath home is situated on a deep lot (50 x 140) with 1283 sq. ft., Bamboo hardwood floors in several rooms, split bedroom floor plan, large kitchen with tile floors, and oak cabinets, and the dining room has a tongue and groove wood ceiling. The primary bedroom has Bamboo floors, tongue and groove wood

  Melissa Woodman FANNIE HILLMAN & ASSOCIATES

  780 Baffie 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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  $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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  /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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  $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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  $2,450,000

  • 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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  $500,000

  • 4 Beds
  • 3 Baths
  • 2,035 Sq Ft

  2920 Abbey Ct, Winter Park, FL 32792

  Welcome home to the Winter Park Pines with tree lines streets, sidewalks on both sides of the street and a mailman that delivers to your door. This spacious 4-bedroom, 3-bath home offers the ideal canvas for customization, nestled in one of Winter Park’s most desirable neighborhoods. This diamond in the rough—brimming with charm and just waiting for your personal touch! Step inside through a

  Amy Turner KELLER WILLIAMS WINTER PARK

  2920 Abbey Ct, Winter Park, FL 32792
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  $6,500,000

  • 6 Beds
  • 5.5 Baths
  • 5,759 Sq Ft

  887 Georgia Ave, Winter Park, FL 32789

  Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1-acre lot. Exuding timeless charm with a subtle New England ambiance, this residence represents the best of historic Winter Park living—all within walking distance to Park Avenue.This stately 6-bedroom, 5.5-bathroom home

  Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  887 Georgia Ave, Winter Park, FL 32789
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  $475,000

  • Land
  • 0.16 Acre
  • $2,968,750 per Acre

  1414 Bessmor Rd, Winter Park, FL 32789

  ?? Land for Sale – Build Your Dream Home in Winter Park! Just minutes from Park Avenue!Discover the perfect opportunity to build your custom home in one of Central Florida’s most desirable neighborhoods! This prime homesite is nestled among newly built luxury residences and offers the ideal canvas for your future home.The owner has already completed the heavy lifting — the previous

  Miranda Azer PARKVIEW REAL ESTATE

  1414 Bessmor Rd, Winter Park, FL 32789
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  $765,000

  • 4 Beds
  • 3 Baths
  • 3,020 Sq Ft

  2144 Ridge Dr, Winter Park, FL 32792

  CURRENTLY REMODELLING!! Welcome to 2144 Ridge Drive, a beautifully updated home nestled in the heart of Winter Park, Orlando.This spacious 4 bedroom, 3 bathroom residence offers a bright, open floor plan perfect for both relaxing and entertaining. The chef-inspired kitchen features high-end appliances and ample counter space, while the expansive master suite provides a serene retreat with a

  sahil rama EXP Realty LLC

  2144 Ridge Dr, Winter Park, FL 32792
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  $874,900

  • 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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  $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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  $210,000

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit C202, Winter Park, FL 32789

  This property located in a peaceful community and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can

  Hoover Yap PRIMESTATE REALTY, INC.

  1695 Lee Rd Unit C202, 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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  $1,450,000 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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  /6

  $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 Open Sun 11AM - 1PM

  • 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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  /12

  $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 11AM - 1PM

  • 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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  $469,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2949 Clever Ln, Winter Park, FL 32792

  Welcome to this stunning former model townhome built in 2023, ideally located in the highly sought-after gated community of Grayson Square in Winter Park, Florida. This beautifully designed residence offers a blend of modern finishes and functional layout, with the first floor featuring a completely open floor plan bathed in natural light. The spacious kitchen boasts quartz countertops, upgraded

  Joseph Sipp KELLER WILLIAMS WINTER PARK

  2949 Clever Ln, Winter Park, FL 32792
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  /2

  $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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