Winter Park, FL Homes for Sale

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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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  /13

  $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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  $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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  /24

  $1,664,900 New Construction

  • 4 Beds
  • 5 Baths
  • 2,812 Sq Ft

  607 Ellen Dr, Winter Park, FL 32789

  Step into refined living at 607 Ellen Drive, a brand-new two-story modern minimalist home by award-winning Lazarus Winter Park. With 2,812 square feet, this stunning residence offers four bedrooms, a dedicated office, and a luxurious first-floor primary suite. Light oak wide-plank floors and glass stair railings create a sleek, airy aesthetic. Expansive sliding glass doors fully open to a private

  Doug Addeo COMMUNITY REALTY ASSOCIATES

  607 Ellen Dr, Winter Park, FL 32789
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  /83

  $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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  /10

  $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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  /87

  $545,000 Open Sat 1PM - 4PM

  • 4 Beds
  • 3 Baths
  • 2,170 Sq Ft

  5255 Seminole Ave, Winter Park, FL 32792

  Price Improvement!!Great opportunity!This stunning 4-bedroom, 3-bath home is currently under construction in one of the most desirable locations—Winter Park! NO HOA! this property features fully permitted updates including Electrical (2024), Plumbing (2024), Water Heater (2024), Roof (2024), and HVAC (2024).Designed with abundant windows for natural light and tile flooring throughout,

  Nohora Gomez COLDWELL BANKER RESIDENTIAL RE

  5255 Seminole Ave, Winter Park, FL 32792
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  /12

  $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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  /100

  $8,500,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,564 Sq Ft

  2661 Vía Tuscany, Winter Park, FL 32789

  CALLING HIGHEST AND BEST BY 4/30/2025!! Introducing 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 building codes, this home follows commercial-grade

  Prescilla Vazquez PV LUXURY GROUP PA

  2661 Vía Tuscany, 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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  $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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  $469,900 Pre-Foreclosure

  • 3 Beds
  • 2.5 Baths
  • 1,801 Sq Ft

  2037 Canny Cove, Winter Park, FL 32792

  Nestled in the coveted Grayson Square community of highly desired Winter Park, FL, 2037 Canny Cove Lane is a contemporary 3-bedroom, 2.5-bath townhome built in 2023. The open-concept layout features a stylish kitchen with stainless steel appliances, quartz countertops, and ample storage, seamlessly flowing into the spacious gathering room. The owner's suite offers a private retreat with an

  Claire Sims LLC LPT REALTY, LLC

  2037 Canny Cove, Winter Park, FL 32792
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  /2

  $5,000

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  7793 Country Place Unit J7, Winter Park, FL 32792

  Foreclosure Auction Ends August 14, 2025 at 11:00 AM EST. Discover this delightful 3-bedroom, 2-bathroom condominium located in the desirable Goldenrod Villas Condo community in Winter Park, FL, offering access to a community pool. The list price is the opening bid for the online auction. Sold As-is with Clear Title. Explore more details and submit your bid through Federa Home App.

  Jamie Boone Jaime L Boone LLC

  7793 Country Place Unit J7, 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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  /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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  /31

  $699,900

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft

  2338 Tuscarora Trail, Maitland, FL 32751

  With over $60k in upgrades, this beautiful 4-bedroom, 2-bathroom lakeside retreat is tucked away in the highly sought-after Dommerich Hills community! Enjoy living next to the tranquil waters of Lake Waumpi and a peaceful conservation area, offering a rare blend of natural beauty and everyday comfort. Surrounded by mature trees and set on over a 1-acre lot, the backyard is a true sanctuary,

  Megan Hedrick Mark Spain Real Estate

  2338 Tuscarora Trail, Maitland, FL 32751
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  $310,000

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

  1618 Gulfview Dr Unit 417, Maitland, FL 32751

  One or more photo(s) has been virtually staged. Welcome to this exquisitely renovated home offering the best value in the maintenance-free community of Park Lake Grove! This stunning 3-bedroom, 3-bathroom property features 1,328 square feet of beautifully updated living space and a rear-facing, fully enclosed one-car garage. Every inch of this home has been thoughtfully renovated with quality

  Wendy Aldana LLC NETWORTH REALTY OF ORLANDO, LLC

  1618 Gulfview Dr Unit 417, Maitland, FL 32751
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  $775,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 1,936 Sq Ft

  3074 Stanfield Ave, Orlando, FL 32814

  Welcome to this beautiful two-story home located in the heart of highly sought-after Baldwin Park! As you approach this home, you will notice that it has a charming and spacious covered front porch and a fully fenced front yard. Upon entering the home, you will discover that the home has a thoughtfully designed living space. This light-filled home blends charm and functionality. Step inside to

  Jenny Lake FANNIE HILLMAN & ASSOCIATES

  3074 Stanfield Ave, Orlando, FL 32814
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  /57

  $329,000

  • 2 Beds
  • 2 Baths
  • 1,078 Sq Ft

  13427 Blue Heron Dr Unit 2-1401, Orlando, FL 32789

  The Blue Heron Beach Resort is located just a few miles from the entrance of Walt Disney World. This resort primarily offers two-bedroom suites that cater to families and groups it feature full kitchens, living rooms, and private balconies with excellent views of Lake Bryan, and watch the Disney fireworks every night. It's a great opportunity for your own or become a first time Airbnb

  Yukey Hoo U KEY REALTY

  13427 Blue Heron Dr Unit 2-1401, Orlando, FL 32789
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  /35

  $655,000

  • 3 Beds
  • 2 Baths
  • 1,938 Sq Ft

  489 Penny Ln, Maitland, FL 32751

  Presenting 489 Penny Lane located in the sought after Gated Community known as Brittany Gardens. Upon arrival you will be impressed with the front yard garden featuring landscape lighting, flagstone accents, lush landscaping and a paver driveway. The inviting front porch offers a welcoming and visually appealing space where you will transition from outdoors into modern luxury in this beautifully

  Erin Tompkins COLDWELL BANKER RESIDENTIAL RE

  489 Penny Ln, Maitland, FL 32751
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  /65

  $564,900

  • 3 Beds
  • 2.5 Baths
  • 1,806 Sq Ft

  5489 Baldwin Park St, Orlando, FL 32814

  MOTIVATED SELLER OFFERING FIRST YEAR HOA FEE TO BE PAID AT CLOSING!!! Luxury & Location define this sensational two story townhome.This beautiful place features an open, designer kitchen with gorgeous granite countertops throughout, upgraded appliances, and a very convenient under sink reverse osmosis system. The breakfast bar opens to a cozy dining/family room. The large, tranquil owner's suite

  Oliver Figuereo EXECUTIVE REAL ESTATE

  5489 Baldwin Park St, Orlando, FL 32814
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  /34

  $709,990

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft

  1655 Sunnyside Dr, Maitland, FL 32751

  Welcome to this one-of-a-kind vintage charmer in the heart of Maitland, Florida! Nestled on a beautifully landscaped corner lot, this 3-bedroom, 2-bathroom historic cottage offers 1,418 square feet of thoughtfully designed living space. Just minutes from downtown Maitland and the vibrant energy of Winter Park, you’ll love the perfect blend of convenience and character this home

  Joseph Sipp KELLER WILLIAMS WINTER PARK

  1655 Sunnyside Dr, Maitland, FL 32751
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  $294,000 Open Sat 10AM - 12PM

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

  1040 Hamlet Dr, Maitland, FL 32751

  This beautifully maintained three-bedroom, two-bath residence features an inviting open floor plan, perfect for both entertaining and everyday living. Recently painted with a fresh interior, the home radiates warmth and brightness throughout. Enjoy modern comforts with a brand-new air conditioning system installed just six months ago, ensuring a cool and comfortable atmosphere year-round. The

  Bianca Botelho RE/MAX ASSURED

  1040 Hamlet Dr, Maitland, FL 32751
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  /40

  $1,097,000

  • 3 Beds
  • 3 Baths
  • 2,460 Sq Ft

  1901 Lake Sue Dr, Orlando, FL 32803

  One story, 3-bedroom, 3 bath, RENOVATED home with resort-style backyard and screened lap pool is ready to move in to. It features a modern kitchen with a marble Breakfast bar, marble countertops and stainless-steel appliances. An Open floor plan with lots of natural light flowing throughout. The huge primary Bedroom suite with sitting area and private bath, his and hers closets, opens to the

  Pamela Stewart REALCOM REAL ESTATE SERVICES INC

  1901 Lake Sue Dr, Orlando, FL 32803
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  $1,350,000

  • 3 Beds
  • 2.5 Baths
  • 2,960 Sq Ft

  3308 Middlesex Rd, Orlando, FL 32803

  This breathtaking Spanish-style home, winner of First Place for Design by the American Society of Interior Designers in 2020, is a true masterpiece. Designed by HGTV Designer of the Year John McClain, it blends modern luxury with timeless charm.The magazine-worthy kitchen—featured on Southern Living’s website—boasting Sherwin William's 2021 color of the year, the custom Urbane Bronze

  Julie Bettosini STOCKWORTH REALTY GROUP

  3308 Middlesex Rd, Orlando, FL 32803
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  $599,900

  • 2 Beds
  • 2.5 Baths
  • 1,897 Sq Ft

  2979 Upper Park Rd, Orlando, FL 32814

  Stately Townhome in Baldwin Park! Welcome to this exquisite townhome, ideally situated adjacent to the charming Windsong community and the well-established City of Winter Park. This spacious residence offers a refined living experience with a perfect blend of comfort and elegance.Upon entry, you are greeted by a formal living and dining room, providing an open and inviting space for entertaining

  Timothy Bratcher COLDWELL BANKER RESIDENTIAL RE

  2979 Upper Park Rd, Orlando, FL 32814
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  /5

  $419,000

  • Land
  • 0.15 Acre
  • $2,793,333 per Acre

  1830 Lake Sue Dr, Orlando, FL 32803

  Incredible Opportunity to Build Your Dream Home in Audubon Park! This rare 55’ x 115’ cleared lot offers a prime location to create your perfect home in the heart of the vibrant Audubon Park neighborhood. Just a short stroll to the beautiful Leu Gardens and the lively shops, restaurants, and bars along Corrine Drive. Zoned for the highly sought-after Audubon K-8 and Winter Park High School, this

  Stacy Wright MEGAN DOWDY REALTY, LLC

  1830 Lake Sue Dr, Orlando, FL 32803
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  /66

  $2,890,000

  • 4 Beds
  • 4.5 Baths
  • 3,837 Sq Ft

  1426 Nottingham St, Orlando, FL 32803

  Straddling the charming and highly desirable Winter Park/Orlando border, this exceptional, newly painted 4-bedroom, 4.5-bath custom home offers an extraordinary living experience. Built with the utmost attention to detail and remodeled by the celebrated Slocum Platts in 2007, this residence sits on an expansive triple lot with 150 feet of frontage and nearly half an acre of lush, professionally

  Chad Isenhart PREMIER SOTHEBY'S INTL. REALTY

  1426 Nottingham St, Orlando, FL 32803
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  /4

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,538 Sq Ft

  113 Gem Lake Dr, Maitland, FL 32751

  Must remodel this 1939 home that was moved from Park Avenue many years ago but now rests in Maitland bordering Winter Park. This home is a piece of history with character but in need of some TLC. Beautifully arched high ceiling along with a fireplace in the formal living room. The Florida room is surrounded by glass sliding doors that open to a wooden patio with French doors, countless windows,

  Darryl Donkel HOME WISE REALTY GROUP, INC.

  113 Gem Lake Dr, Maitland, FL 32751
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  /26

  $389,500

  • 3 Beds
  • 2 Baths
  • 1,885 Sq Ft

  2625 Queen Mary Place, Maitland, FL 32751

  Auction Property. Located in desirable Brittany Gardens, this home offers spacious living areas and a smart, open floorplan — perfect for customization and renovation. Step inside to find a large great room, ideal for entertaining. The generously sized master suite features a luxurious bathroom with a soaking tub, separate shower enclosure, and dual vanities. Additional bedrooms are

  Wade Stafford ALL FLORIDA PROPERTY GROUP,INC

  2625 Queen Mary Place, Maitland, FL 32751

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