Homes for Sale near Winter Park High

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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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  $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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  $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

  $495,000

  • Land
  • 0.16 Acre
  • $3,093,750 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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  /2

  $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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  /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

  $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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  /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
  • 1.70 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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  $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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  $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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  $1,795,000 New Construction

  • 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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  $639,800 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
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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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  $2,495,000 New Construction

  • 6 Beds
  • 8 Baths
  • 4,390 Sq Ft

  734 Terra Place, Maitland, FL 32751

  Presenting a stunning new construction residence located on a quiet cul-de-sac offering a seamless blend of luxury, functionality and modern design. The main home features four spacious bedroom suites, a dedicated office and a bonus/flex area, 4 full baths and 2 half baths, while the property also includes a rare-to-find one-level detached 1,143 sf 2BE/2BA guest house that includes a kitchen and

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  734 Terra Place, Maitland, FL 32751
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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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  $3,225,000 New Construction

  • 5 Beds
  • 6 Baths
  • 5,188 Sq Ft

  1849 Oak Ln, Orlando, FL 32803

  Pre-Construction. To be built. Introducing The Vireo, an exceptional new residence crafted by Valdara Custom Homes, where expansive walls of glass and wide-plank oak flooring set a tone of timeless elegance. Designed with culinary enthusiasts and entertainers in mind, the chef’s kitchen boasts a grand center island, a separate butler’s pantry, and a top-of-the-line appliance package. The kitchen

  Harif Hazera PREMIER SOTHEBY'S INTL. REALTY

  1849 Oak Ln, Orlando, FL 32803
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  $3,615,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,290 Sq Ft

  4654 Thornlea Rd, Orlando, FL 32817

  Pre-Construction. To be built. Unparalleled Lakefront Luxury on Lake Waunatta, a private Ski Lake in Central Florida. Nestled at the end of a quiet cul-de-sac, this custom-built 5,290 sq. ft. estate offers 100 feet of private lake frontage and breathtaking panoramic views. Situated on three-quarters of an acre with high and dry land, this two-story masterpiece is designed for effortless luxury

  Scott Webb BLUE CRAB REALTY LLC

  4654 Thornlea Rd, Orlando, FL 32817
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  /8

  $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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  /13

  $614,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,030 Sq Ft

  8013 Colby Cir, Orlando, FL 32817

  Move-In Ready! Introducing our innovative new Willow plan, located in a quaint area of the Community with just 10 homes for added privacy, and featuring a large front Porch, 4 Bedrooms, 3 Full Baths, and 2 car Garage. Exceptional features include 9'4" ceilings, 8' doors throughout, and upgraded floor tile in the main living areas. This incredible home offers an open concept design with spacious

  Stephen Wood LANDSEA HOMES OF FL, LLC

  8013 Colby Cir, Orlando, FL 32817
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  $589,990 New Construction

  • 3 Beds
  • 3 Baths
  • 1,942 Sq Ft

  8007 Colby Cir, Orlando, FL 32817

  Move-In Ready! Introducing our exciting new Sabal Craftsman plan, located in a quaint section of the Community with just 10 homes for added privacy, and featuring a spacious covered front Porch, 3 Bedrooms, 3 Full Baths, and 2 car Garage. Exceptional features include 9'4" ceilings, 8' doors throughout, and 5 1/4" baseboards, with upgraded floor tile featured in main living areas. This incredible

  Stephen Wood LANDSEA HOMES OF FL, LLC

  8007 Colby Cir, Orlando, FL 32817
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  $1,356,130 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,306 Sq Ft

  3611 Chelsea St, Orlando, FL 32803

  Under Construction. Soak up all the charm of this new home in the heart of Audubon Park. The Seaberg by David Weekley Homes is an ideal family home, offering 4 bedrooms, 3 full bathrooms, a powder bath, a large bonus retreat, a vast dining room and a study. When you enter the home you are greeted by a spacious open floor plan appointed with amazing finishes and tons of natural light pouring in

  Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  3611 Chelsea St, Orlando, FL 32803
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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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  $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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  $1,800,000 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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  /22

  $849,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,051 Sq Ft

  1917 S Lakemont Ave, Winter Park, FL 32792

  Special financing or closing cost credits available for qualified buyers!Introducing the 2024 PARADE OF HOMES ORLANDO WINNER - BEST IN CLASS! This exceptional, move-in ready residence is perfectly situated between the serene shores of Lake Spier and Lake Compton in the exclusive Lake Spier Crossing community of Winter Park.Discover modern luxury with 10 impeccably designed

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1917 S Lakemont Ave, Winter Park, FL 32792
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  /16

  $564,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,105 Sq Ft

  2585 Cavanaugh Dr, Orlando, FL 32817

  Move-In Ready! Our innovative Miles plan, with 9'4" ceilings, features 4 bedrooms, 3 Full Baths, and 2 car Garage. Exceptional features include 5 1/4" baseboards, 8' interior doors, and window blinds throughout, with beautiful tile flooring featured in the main living areas. This incredible home offers a spacious open concept design with separate eat-in dinette area and adjacent Family Room

  Stephen Wood HANOVER FAMILY BUILDERS LLC

  2585 Cavanaugh Dr, Orlando, FL 32817
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  /11

  $624,990 New Construction

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

  2560 Cavanaugh Dr, Orlando, FL 32817

  Move-In Ready! Our extraordinary Newcastle plan with 9'4" first floor ceilings offers an open-concept design featuring 4 Bedrooms, 2.5 Baths, and 2 car Garage. This well-appointed home includes 5 1/4" baseboards, 8' interior doors on 1st floor, and window blinds throughout, with beautiful floor tile featured in 1st floor main living areas. Separate Living Room by front entry can be used as office

  Stephen Wood HANOVER FAMILY BUILDERS LLC

  2560 Cavanaugh Dr, Orlando, FL 32817
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  $849,900 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,063 Sq Ft

  1907 S Lakemont Ave, Winter Park, FL 32792

  Special financing or closing cost credits available for qualified buyers!Introducing the 2024 PARADE OF HOMES ORLANDO WINNER - BEST IN CLASS! This exceptional, move-in ready residence is perfectly situated between the serene shores of Lake Spier and Lake Compton in the exclusive Lake Spier Crossing community of Winter Park.Discover modern luxury with 10 impeccably designed

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1907 S Lakemont Ave, Winter Park, FL 32792
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  /17

  $125,000

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft

  228 Scottsdale Square Unit 228, Winter Park, FL 32792

  Short Sale. Short Sale. Short Sale. SHORT SALE. SHORT SALE, AS IS,Location, Location, Location Winter Park, Excellent opportunity to own a townhome 3/2, close to everything. to express way and restaurants,

  Amanda Linsey VYLLA HOME

  228 Scottsdale Square Unit 228, Winter Park, FL 32792

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