Homes for Sale near Maitland Middle School

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  $1,215,000

  • 6 Beds
  • 4 Baths
  • 2,284 Sq Ft

  726 and 720 N Pennsylvania Ave, Winter Park, FL 32789

  Welcome to this exceptional duplex, a rare gem in Winter Park offering unmatched flexibility and investment potential. Whether you’re looking for a turnkey rental property, a multigenerational living solution, or a home with a private in-law or student suite, this property delivers! Each spacious unit boasts 3 bedrooms and 2 bathrooms, designed with a modern, elegant aesthetic. With dual living

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  726 and 720 N Pennsylvania Ave, Winter Park, FL 32789
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  $250,000

  • Land
  • 0.26 Acre
  • $961,538 per Acre

  1130 Mechanic St, Maitland, FL 32751

  This 0.26 acre cleared lot is ready for you to create the home of your dreams! Nestled among majestic oak trees, it provides a serene and private setting while maintaining easy access to everything you need. Enjoy the perfect blend of a peaceful, country-like atmosphere right in the heart of the city. Located less than a mile from Maitland Community Park, you'll have access to sports courts,

  Richard Palmano PALMANO GROUP RE BROKERAGE LLC

  1130 Mechanic St, Maitland, FL 32751
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  $2,499,000

  • 4 Beds
  • 5 Baths
  • 4,875 Sq Ft

  2550 Venetian Way, Winter Park, FL 32789

  "The richness of an artist is the fusion of influences that have shaped his life and work", ~ Fernando Botero. WELCOME HOME to 2550 Venetian Way, located in the historic and renowned city of Winter Park, accessing the Maitland/Winter Park CHAIN OF LAKES! This custom modern/contemporary 2008 build, derives it's over 4800 sq/ft of essence and uniqueness by fusing vibrant colors and eloquence with

  Brian Rotenberger COMPASS FLORIDA LLC

  2550 Venetian Way, Winter Park, FL 32789
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  $1,999,993

  • 6 Beds
  • 4 Baths
  • 3,853 Sq Ft

  1451 Lyndale Blvd, Winter Park, FL 32789

  **Luxurious Winter Park Estate with Detached TWO bedroom Guest House** RENOVATED POOL HOME with NO HOA! TWO Primary Bedrooms located on the main floor! Welcome to a world of unparalleled luxury and elegance in the heart of historic Winter Park, FL. This exquisitely renovated two-story pool home, set on a sprawling corner lot, offers a rare opportunity to experience the pinnacle of

  Christopher Soucy REALTY ONE GROUP MVP

  1451 Lyndale Blvd, Winter Park, FL 32789
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  $3,990,900

  • Land
  • 7.82 Acres
  • $510,345 per Acre

  1250 N Maitland Ave, Maitland, FL 32751

  Exceptional opportunity for commercial developers, residential builders, or those seeking a private estate within the City of Maitland, Orange County. This rare offering includes approximately ±8 acres of usable land comprising multiple contiguous parcels and rights-of-way. The property is designated as a Traditional Neighborhood and zoned RS-2.A previously submitted Planned Development

  Armando Gonzalez AG REALTY SERVICES LLC

  1250 N Maitland Ave, Maitland, FL 32751
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  $64,000

  • Land
  • 0.08 Acre
  • $800,000 per Acre

  25 People St, Eatonville, FL 32751

  This unique commercial lot located in a Redevelopment AREA in the heart of The Historic Town of Eatonville. This area is going thru a major redevelopment phase, with the expansion of 1-4 this area looking expand go within the next few years. Buyer is responsible for due diligence.

  Knorlene O'Brien Martin KELLER WILLIAMS RLTY,BREVARD

  25 People St, Eatonville, FL 32751
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  /19

  $510,000

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

  2627 Ambergate Rd, Winter Park, FL 32792

  Price Reduced !! This beautiful and remodeled home is turnkey and ready to move in!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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  /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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  $265,000

  • Land
  • 0.27 Acre
  • $981,481 per Acre

  0 Mechanic St, Maitland, FL 32751

  Unlock the Potential of Your Dream Property in Maitland, Florida!Discover a prime opportunity to build your vision in the heart of Maitland, a charming and thriving community just minutes from downtown Orlando. This vacant land offers a blank canvas for your dream home or investment property. Nestled in a highly desirable area, you'll enjoy easy access to top-rated schools, tranquil parks,

  Cheree Graham KELLER WILLIAMS REALTY AT THE PARKS

  0 Mechanic St, Maitland, FL 32751
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  $1,450,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,565 Sq Ft

  1807 Yorkshire Dr, Winter Park, FL 32792

  Under Construction. Location, location, location! Nestled in Winter Park, this home is convenient to the best in shopping, dining and entertainment! The two-story Easterly design hosts four bedrooms, four full bathrooms, one half baths, study and sits on an oversized homesite. The open concept living area flows beautifully from the family room and dining room to the kitchen with laminate floors

  Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  1807 Yorkshire Dr, Winter Park, FL 32792
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  $975,000 New Construction

  • 3 Beds
  • 3 Baths
  • 1,875 Sq Ft

  870 Carver St, Winter Park, FL 32789

  Welcome to 870 Carver Street, a versatile three-bedroom, three-bath residence offering privacy, thoughtful design, and two distinct living experiences in the heart of Winter Park. With 1,875 square feet under air, the property includes a 1,209-square-foot, two-bedroom, two-bath main home and a 666-square-foot, one-bedroom, one-bath garage apartment, ideal for multigenerational living, rental

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  870 Carver St, Winter Park, FL 32789
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  $2,350,000 New Construction

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

  2412 Chantilly Ave, Winter Park, FL 32789

  Step into a world of modern elegance in this newly completed estate in the heart of Winter Park. Masterfully constructed, this five-bedroom residence with six full and one half baths spans over 4,500 square feet of luxurious design and comfort. From the moment you enter the soaring foyer, light pours through expansive windows that frame every angle of the open floor plan, creating a seamless

  Josh Hill THE AGENCY ORLANDO

  2412 Chantilly Ave, Winter Park, FL 32789
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  $7,200,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 5,939 Sq Ft

  550 Palmer Ave, Winter Park, FL 32789

  Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff

  John McDade FANNIE HILLMAN & ASSOCIATES

  550 Palmer Ave, Winter Park, FL 32789
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  $5,300,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,738 Sq Ft

  1302 Raintree Place, Winter Park, FL 32789

  An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired

  Rikhil Amin FANNIE HILLMAN & ASSOCIATES

  1302 Raintree Place, Winter Park, FL 32789
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  $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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  $4,250,000 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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  $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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  $2,935,000 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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  $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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  $1,759,000 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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  $6,600,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,636 Sq Ft

  2661 Vía Tuscany, Winter Park, FL 32789

  CALLING HIGHEST AND BEST BY 09/26/2025!! SELLER FINANCING AVAILABLE WITH VERY ATTRACTIVE TERMSIntroducing 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

  Prescilla Vazquez PV LUXURY GROUP PA

  2661 Vía Tuscany, Winter Park, FL 32789

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