Homes for Sale near Maitland Middle School

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  /30

  $440,000

  Open Sat 9AM - 7PM $21K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,264 Sq Ft

  2052 Leanne Ct, Winter Park, FL 32792

  Welcome to 2052 Leanne Ct, a home that exudes warmth and elegance. The living room is graced with a cozy fireplace, perfect for those chilly evenings. The kitchen is a chef's dream, boasting all stainless steel appliances for a sleek, modern look. The primary bedroom is a haven of comfort with double closets for ample storage. The primary bathroom is a sanctuary with double sinks, providing ample

  Karen Albright OPENDOOR BROKERAGE LLC

  2052 Leanne Ct, Winter Park, FL 32792
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  /20

  $308,000

  • 3 Beds
  • 2 Baths
  • 1,076 Sq Ft

  1074 Hamlet Dr, Maitland, FL 32751

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that blends comfort, convenience, and an unbeatable location. From the moment you step inside, you’ll notice the inviting layout featuring a spacious living area filled with natural light and a functional kitchen equipped with newer stainless steel appliances—perfect for everyday living and entertaining alike. The home sits on a

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  1074 Hamlet Dr, Maitland, FL 32751
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  /63

  $965,000

  • 4 Beds
  • 3.5 Baths
  • 2,407 Sq Ft

  2112 Chippewa Trail, Maitland, FL 32751

  LONG AWAITED ARRIVAL IN DESIRABLE MAITLAND SUBDIVISION This beautiful, impeccably maintained and updated four bedroom three and a half bath pool home absolutely has it all! Perfectly located in Maitland’s much sought after Dommerich neighborhood and walking distance to top rated elementary and middle schools. This attractive split-floor plan offers four spacious bedrooms and three full baths on

  Laura Heidrich COLDWELL BANKER REALTY

  2112 Chippewa Trail, Maitland, FL 32751
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  /67

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 3,174 Sq Ft

  1420 Magnolia Ave, Winter Park, FL 32789

  On a picturesque brick street in Winter Park, this beautifully designed modern traditional pool home blends timeless architecture with thoughtful, high-end finishes throughout. Built in 2015 and offering over 3,100 square feet, the home features four bedrooms, three full baths, and a flexible three-story layout designed for everyday living and effortless entertaining. A welcoming front porch

  Audra Wilks PREMIER SOTHEBY'S INTL. REALTY

  1420 Magnolia Ave, Winter Park, FL 32789
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  /32

  $1,299,000

  New Construction $126K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,046 Sq Ft

  1870 Walker Ave, Winter Park, FL 32789

  This new residence, thoughtfully designed by Michael Wenrich, captures the timeless elegance and refined simplicity reminiscent of the iconic coastal architecture of Alys Beach. Clean architectural lines, graceful curves, and abundant natural light combine to create a home that feels sophisticated and inviting. Inside, gorgeous chevron-patterned wood floors flow throughout the main living areas,

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1870 Walker Ave, Winter Park, FL 32789
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  /47

  $439,900

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft

  1140 S Orlando Ave Unit H3, Maitland, FL 32751

  Virtually Staged. RARE LAKEFRONT opportunity to Live right on LAKE MAITLAND! Sip your morning coffee with one of the most premier views in the entire community! BONUS: It's on the main FIRST floor, so NO STAIRS! Just a pure unencumbered view of Lake Maitland right from your living room! And only a few steps to the dock or community pool!! This unit has the EXTRA HALF BATHROOM and has been

  Chris Schiffermiller UNITED REAL ESTATE PREFERRED

  1140 S Orlando Ave Unit H3, Maitland, FL 32751
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  /25

  $427,400

  $23K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft

  220 Alpine Dr, Maitland, FL 32751

  Opportunity in the Maitland / Winter Park area! This one-owner home, held by the same family since the 1960s, is ideally located near shopping, dining, parks, and major roadways, providing convenient access throughout Central Florida.The property offers potential for renovation, expansion, or redevelopment, with a lot that provides space for future improvements. Ideal for homeowners,

  Beth Hathaway PREMIUM PROPERTIES R.E SERVICE

  220 Alpine Dr, Maitland, FL 32751
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  /47

  $349,000

  • 2 Beds
  • 1.5 Baths
  • 816 Sq Ft

  1140 S Orlando Ave Unit F11, Maitland, FL 32751

  This luxury condominium is in the established complex of Lake Maitland Terrace which sits on the shores of Lake Maitland, Winter Park Chain of Lakes. This immaculately maintained complex includes 11, 2-story, mid-century modern buildings sprawled across several acres, creating beautiful green space and picturesque views across the lake. This unit is special. A complete renovation with every

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1140 S Orlando Ave Unit F11, Maitland, FL 32751
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  /5

  $195,000

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft

  4756 Tangerine Ave Unit 4756, Winter Park, FL 32792

  Discover the potential of this 2-bedroom, 2-bath end-unit condominium located in the desirable Wrenwood Condominium community in Winter Park, Florida. Offering 1,058 square feet of living space, this home presents an excellent opportunity for buyers seeking affordability, convenience, and the chance to add their own personal style. Inside, you'll find ceramic tile flooring throughout, knockdown

  Ada Sanchez HOME BUYER HELPER REAL ESTATE LLC

  4756 Tangerine Ave Unit 4756, Winter Park, FL 32792
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  /70

  $3,995,000

  Open Sun 2PM - 4PM

  • 5 Beds
  • 5.5 Baths
  • 4,483 Sq Ft

  1600 Legion Dr, Winter Park, FL 32789

  Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor

  Brian Teach COLDWELL BANKER REALTY

  1600 Legion Dr, Winter Park, FL 32789
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  /38

  $1,175,000

  $25K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,469 Sq Ft

  1404 Border Dr, Winter Park, FL 32789

  Experience the perfect blend of modern luxury, thoughtful design, and an unbeatable Winter Park location in this stunning custom residence built in 2023 by acclaimed builder Odin Homes. Showcasing over two years of gentle ownership, this exceptional home lives like new and offers a rare opportunity to own a move-in-ready custom home without the wait of new construction. Designed with

  Brian Hyser THE AGENCY FL

  1404 Border Dr, Winter Park, FL 32789
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  /39

  $1,599,000

  $51K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 3,400 Sq Ft

  541 Manor Rd, Maitland, FL 32751

  Tucked between the shores of Lake Nina and Lake Maitland, this beautifully reimagined California ranch blends modern design with effortless everyday living in one of Maitland’s most desirable locations. Completely remodeled in 2022, the home showcases a fresh, sophisticated aesthetic with thoughtfully curated finishes throughout. The light-filled interior offers seamless flow between living

  Sarah Tomlinson COMPASS FLORIDA LLC

  541 Manor Rd, Maitland, FL 32751
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  /4

  $2,099,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,865 Sq Ft

  938 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. Welcome to The Enclave, an exclusive boutique community in the heart of Winter Park featuring just 23 thoughtfully crafted residences by FG Schaub Custom Homes. Nestled beneath mature oak canopies and surrounded by lush natural beauty, this private enclave offers the perfect balance of tranquility, sophistication, and walkable convenience. Ideally located just

  Laura Earl CORCORAN PREMIER REALTY

  938 Enclave Place, Winter Park, FL 32792
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  /37

  $1,324,000

  $25K PRICE DROP

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

  802 Hamilton Place Ct, Winter Park, FL 32789

  Built in 2018, this beautifully designed 4-bedroom, 3.5-bath home offers 2,843 square feet of refined living in a prime Winter Park location, walking distance to Park Avenue and the renowned Winter Park 9 golf course. Thoughtful architectural details set it apart, including shiplap ceilings in the living room and kitchen, decorative ceiling finishes in the bedrooms, and a striking tile staircase

  Jacob Theisen FLORIDA CAPITAL REALTY

  802 Hamilton Place Ct, Winter Park, FL 32789
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  /38

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  1600 Alabama Dr Unit 402, Winter Park, FL 32789

  Nestled along one of Winter Park's most cherished brick-lined streets, this elegantly appointed two-bedroom, two-bath residence at the prestigious Alabama offers a rare opportunity to experience the very best of lakeside luxury living. With 1,574 square feet of thoughtfully designed interior space, this exceptional unit captures the timeless charm and sophistication that have made the Alabama one

  Kelly Price KELLY PRICE & COMPANY LLC

  1600 Alabama Dr Unit 402, Winter Park, FL 32789
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  /75

  $1,495,000

  • 4 Beds
  • 4 Baths
  • 2,756 Sq Ft

  1581 Magnolia Ave, Winter Park, FL 32789

  Beautifully updated with a refined, welcoming feel, this two-story home sits on a charming brick-lined street in the heart of Winter Park, just minutes from the shops, dining and parks that make the area desirable. Natural light fills this home, with four bedrooms and four full baths with custom details throughout including wonderful wood flooring throughout the first level. The well designed

  Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

  1581 Magnolia Ave, Winter Park, FL 32789
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  /54

  $1,395,500

  $100K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,566 Sq Ft

  755 Cranes Ct, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Exceptional value meets timeless elegance in this incredible home nestled in the heart of Maitland, privately situated on a cul de sac within an exclusive gated enclave of custom residences. The Saltwater pool has a brand new sparkling finish! Perfectly positioned between Lake Sybelia and Lake Catherine, this one owner estate offers a rare blend of

  Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

  755 Cranes Ct, Maitland, FL 32751
• 

  /2

  $1,899,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,620 Sq Ft

  910 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a

  Laura Earl CORCORAN PREMIER REALTY

  910 Enclave Place, Winter Park, FL 32792
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  /30

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,623 Sq Ft

  9001 Lake Charity Dr, Maitland, FL 32751

  Welcome to a rare opportunity in the beautiful neighborhood of Druid Hills in Maitland—this charming single-family home is on the market for the first time in 45 years. Built with solid block construction, this home offers exceptional durability, structural soundness, and reliable weather resistance, giving peace of mind for years to come. Situated on an expansive and highly desirable corner lot,

  Joseph Sipp KELLER WILLIAMS WINTER PARK

  9001 Lake Charity Dr, Maitland, FL 32751
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  /64

  $469,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  1140 S Orlando Ave Unit F8, Maitland, FL 32751

  Welcome to Lake Maitland Terrace, a charming lakeside community located on the Winter Park Chain of Lakes. Step inside this beautifully reimagined 2 Bedroom, 2 Bathroom fully renovated, FIRST FLOOR - END UNIT condo, where every detail has been thoughtfully updated for style and function. Expect to be impressed from the moment you enter this custom designed masterpiece. The open layout features a

  Pamela Hamilton HAMILTON GROUP REALTY

  1140 S Orlando Ave Unit F8, Maitland, FL 32751
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  /20

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,146 Sq Ft

  1033 Hamlet Dr, Maitland, FL 32751

  This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels, Whole Foods Markets, and Banking). Access to major highways, minutes to downtown, and Orlando's

  Bennie Olivo BOX REAL ESTATE LLC

  1033 Hamlet Dr, Maitland, FL 32751
• 

  /2

  $1,495,000

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,756 Sq Ft

  905 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. Ideally located within walking distance to Park Avenue and historic Old Winter Park, this exclusive neighborhood blends timeless character with modern luxury. The

  Matthew Burks CORCORAN PREMIER REALTY

  905 Enclave Place, Winter Park, FL 32792
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  /50

  $710,000

  • 4 Beds
  • 2.5 Baths
  • 2,547 Sq Ft

  4334 N Landmark Dr, Orlando, FL 32817

  Nestled on a sprawling .59-acre homesite in East Orlando, this one-of-a-kind pool home is filled with character, architectural charm, and endless potential for the buyer with vision. Ideally located near Lake Pearl you’ll enjoy easy access to UCF, Research Park, SR 408, SR 417, Waterford Lakes Town Center, and Oviedo’s shopping, dining, and entertainment options. From the moment you enter, you’re

  Dan Teston EXP REALTY LLC

  4334 N Landmark Dr, Orlando, FL 32817
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  /13

  $527,300

  $23K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,328 Sq Ft

  210 Alpine Dr, Maitland, FL 32751

  Don't miss this Great opportunity in the Maitland-Winter Park area! There's Potential for Renovation, Expansion or Development with this property. Imagine the Improvements that can be made for the Future. This is a One Owner Home held be the same family since the 1960s. New roof in 2022. The adjacent property at 220 Alpine is also available for purchase.

  Beth Hathaway PREMIUM PROPERTIES R.E SERVICE

  210 Alpine Dr, Maitland, FL 32751
• 

  

  /39

  $975,000

  • 3 Beds
  • 3 Baths
  • 2,192 Sq Ft

  119 Hollie Ct, Maitland, FL 32751

  Located in a premier Maitland neighborhood, 119 Hollie Ct presents a rare opportunity to own a beautifully maintained home in an established pocket community where properties seldom come on the market. This secluded one-level residence sits on a private lot and includes deeded access to the neighborhood boat ramp and the renowned Chain of Lakes, bringing waterfront recreation within easy reach.

  Drew Belani COMPASS FLORIDA LLC

  119 Hollie Ct, Maitland, FL 32751
• 

  

  /22

  $250,000

  • Land
  • 11,325 Sq Ft
  • $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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  /43

  $500,000

  • 3 Beds
  • 2 Baths
  • 1,413 Sq Ft

  512 N Lakemont Ave, Winter Park, FL 32792

  Set on an oversized corner lot in one of the most desirable pockets of Winter Park, this 3-bedroom, 2-bath pool home blends character, location, and opportunity.The backyard is a standout feature, with a resurfaced pool finished in Tahoe Blue PebbleTec and positioned for open sky views, a rare find in a neighborhood known for its mature tree canopy. It creates a bright, inviting outdoor space

  David Plasencia COLDWELL BANKER REALTY

  512 N Lakemont Ave, Winter Park, FL 32792
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  /44

  $6,888,888

  New Construction

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

  2661 Vía Tuscany, Winter Park, FL 32789

  Set in the perfect Winter Park location, within exclusive Via Tuscany, this unique, RESILIENT CONSTRUCTION residence built by Developer & Builder Group, offers a rare blend of enduring quality, refined privacy, and effortless sophistication. Showcasing the finest European finishes, premium appliances, and exquisite light fixtures; this home is filled with clear, natural light and fresh air,

  Belinda Moreno The Keyes Company

  2661 Vía Tuscany, Winter Park, FL 32789
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  /37

  $799,000

  $51K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,175 Sq Ft

  2130 Deloraine Trail, Maitland, FL 32751

  Welcome to this beautifully renovated pool home in the highly sought-after Dommerich neighborhood of Maitland. Offering over 2,000 square feet of living space, this 3-bedroom, 2-bath residence perfectly blends modern upgrades with comfortable, functional living. Inside the home is designed for both everyday living and entertaining. The spacious living room serves as the heart of the home,

  Mario Zendeli COMPASS FLORIDA LLC

  2130 Deloraine Trail, Maitland, FL 32751
• 

  /2

  $1,495,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,738 Sq Ft

  901 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. Welcome to The Enclave at Winter Park—an exclusive collection of architecturally distinctive residences crafted by FG Schaub Custom Homes, blending timeless character with modern luxury. 901 Enclave Place (Lot1) is a thoughtfully designed courtyard home offering an elegant yet functional layout centered around private outdoor living. A charming covered front porch

  Laura Earl CORCORAN PREMIER REALTY

  901 Enclave Place, Winter Park, FL 32792

Showing Results 121 - 150, Page 4 of 4