Winter Park, FL Homes for Sale with Pool

• 

  

  

  /20

  $237,000

  • 2 Beds
  • 1.5 Baths
  • 1,085 Sq Ft

  200 Saint Andrews Blvd Unit 3001, Winter Park, FL 32792

  Experience the best value in Winter Park. Beautifully maintained corner-unit townhome in the desirable Four Seasons community, offering a perfect blend of comfort, privacy and style. This bright and inviting residence features modern laminated floors, new carpet in the bedroom areas, granite kitchen countertops, updated lighting, and recently painted interiors. Enjoy the convenience of a private

  Magaly Laplana Kleros Realty

  200 Saint Andrews Blvd Unit 3001, Winter Park, FL 32792
• 

  

  

  /36

  $329,000

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  311 E Morse Blvd Unit 6-3, Winter Park, FL 32789

  Discover your new downtown Winter Park ground-floor pied-à-terre. Two blocks from Park Avenue, the 1960s mid-century modern Whispering Waters Condominiums are a Winter Park landmark. Your remodeled end-unit studio features an updated open kitchen with plentiful wood cabinets, ceramic tile flooring throughout, new dual-pane windows, a stylish updated bathroom with a step-in shower, and wood

  Richard Traynor FLORIDA ONE REAL ESTATE LLC

  311 E Morse Blvd Unit 6-3, Winter Park, FL 32789
• 

  

  

  /63

  $631,400

  • 2 Beds
  • 2 Baths
  • 1,057 Sq Ft

  265 E Canton Ave Unit GE, Winter Park, FL 32789

  RARE CORNER TOP-FLOOR CONDO WITH AMAZING VIEWS – FULLY FURNISHED AND IN THE HEART OF WINTER PARK! Discover the perfect blend of comfort, style, and unbeatable location! This beautifully maintained 2-bedroom, 2-bath corner unit sits on the top floor of the desirable Villages of Winterset, offering expansive views and abundant natural light throughout. Enjoy the convenience of two elevators, a

  Luciana Amorim Panajotti FLORIDA CONNEXION PROPERTIES

  265 E Canton Ave Unit GE, Winter Park, FL 32789
• 

  

  

  /5

  $1,634,900 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft

  1510 Miller Ave, Winter Park, FL 32789

  Under Construction. New Construction – Modern Luxury Meets Urban Living at Winter Park's Newest Neighborhood, Winter Park Grove!Step into the future of refined living with this stunning new construction pool home, situated in the vibrant heart of Winter Park. Just minutes from the eclectic energy of Park Avenue, this modern masterpiece offers the perfect blend of sophistication, style, and

  Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  1510 Miller Ave, Winter Park, FL 32789
• 

  

  

  /20

  $168,150

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  3651 N Goldenrod Rd Unit 102, Winter Park, FL 32792

  PRICE IMPROVEMENT!! Welcome to this beautifully maintained 2-bedroom, 2-bathroom first-floor condo, offering comfort, convenience, and peace of mind with major updates completed in 2023. This move-in-ready home features a brand-new TRANE A/C unit (2023), a new roof (2023), and new exterior paint (2023)—ensuring long-term efficiency and a fresh, modern look from the moment you arrive. Step inside

  Ashley Fulford CHARLES RUTENBERG REALTY ORLANDO

  3651 N Goldenrod Rd Unit 102, Winter Park, FL 32792
• 

  

  /75

  $3,825,000 New Construction

  • 5 Beds
  • 7 Baths
  • 4,055 Sq Ft

  1820 Glencoe Rd, Winter Park, FL 32789

  Discover premier Winter Park luxury real estate at 1820 Glencoe Road—a stunning Dutch West Indies–inspired custom home built by FG Schaub Custom Homes. Ideally located minutes from Park Avenue, Rollins College, and downtown Winter Park, this residence offers the perfect blend of coastal architecture and modern Florida luxury living. With 4,055 sqft. of thoughtfully designed space, this Winter

  Laura Earl CORCORAN PREMIER REALTY

  1820 Glencoe Rd, Winter Park, FL 32789
• 

  

  /12

  $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 ONE LUXURY INTERNATIONAL LLC

  1525 Granville Dr, Winter Park, FL 32789
• 

  

  /24

  $179,900

  • 1 Bed
  • 1 Bath
  • 653 Sq Ft

  1250 S Denning #122 St Unit 122, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Come take a lovely stroll to Mead Gardens(47 acres), located just around the corner from this adorable condo in one of Winter Park’s most popular communities! The pool is located directly behind this condo! This cozy first-floor unit features brand-new luxury vinyl flooring that gives it a fresh, welcoming feel. The spacious living room has sliders

  Leah Laboy EDEN CREST REALTY, LLC

  1250 S Denning #122 St Unit 122, Winter Park, FL 32789
• 

  

  /50

  $3,250,000

  • 5 Beds
  • 5.5 Baths
  • 4,296 Sq Ft

  473 Fletcher Place, Winter Park, FL 32789

  Welcome to the best of Winter Park living, where luxury meets lifestyle and every day feels like a getaway. This stunning custom home, built by Lundev, sits on a quiet, tree-lined street just a mile from Park Avenue and only steps from beautiful Lake Osceola. Imagine walking to brunch on Park Ave, then coming home to launch your paddleboard from the end of your street. From the moment you pull

  Brandon Geers COMPASS FLORIDA LLC

  473 Fletcher Place, Winter Park, FL 32789
• 

  

  /32

  $1,195,000

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft

  100 S Interlachen Ave Unit 415, Winter Park, FL 32789

  Residence 415 at The Cloisters offers a rare opportunity to own a comprehensively rebuilt home in one of Winter Park’s enduring lakefront communities. Set on the fourth floor, just one block from Park Avenue, this residence blends timeless architecture with newly reimagined design. Taken thoughtfully down to its original structure and meticulously reconstructed with longevity in mind, this

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 415, Winter Park, FL 32789
• 

  

  /68

  $950,000

  • 3 Beds
  • 2 Baths
  • 2,114 Sq Ft

  250 Cortland Ave, Winter Park, FL 32789

  Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of the most picturesque, tree-lined, brick streets in the heart of Winter Park, FL. This meticulously maintained house presents the ideal blend of luxury and comfort, with a low-maintenance, fully landscaped yard, complete with a sprinkler system, an oversized two-car garage, a

  Alexandra Nordine EXP REALTY LLC

  250 Cortland Ave, Winter Park, FL 32789
• 

  

  /28

  $450,000

  • 1 Bed
  • 1 Bath
  • 673 Sq Ft

  640 N Park Ave Unit 5, Winter Park, FL 32789

  Location, Location, Location!Charming first floor 1 bedroom, 1 bath condo ideally located on North Park Avenue in the retro-chic Park Aire complex. Beautifully overhauled in 2018 with quartz counters, new cabinetry, new appliances, custom mosaic kitchen detail, new flooring, new lighting, updated electrical, with picturesque views of the Winter Park Golf Course and Casa Feliz.Enjoy a

  David Auerbach PARK TOWN REAL ESTATE LLC

  640 N Park Ave Unit 5, Winter Park, FL 32789
• 

  

  /7

  $196,400

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft

  2923 Antique Oaks Cir Unit 37, Winter Park, FL 32792

  Condo in Winter Park, FL. 2923 Antique Oaks Cir, Unit 37. Updated 1,105 sq. ft. first-floor, North West corner condo. 2 bedrooms, 2 bathrooms. Located in the Winter Park School District: Updated Interiors: Recently remodeled with modern finishes, including brand-new appliances (convection oven, refrigerator, dishwasher), and a new LG stackable washer/dryer in the interior laundry room. Outdoor

  Cliff Glansen FLATFEE.COM

  2923 Antique Oaks Cir Unit 37, Winter Park, FL 32792
• 

  

  /25

  $99,900

  • 2 Beds
  • 1.5 Baths
  • 1,085 Sq Ft

  126 Scottsdale Square Unit B126, Winter Park, FL 32792

  Excellent opportunity to own this second-floor, 2-bedroom, 1/1-bath condo in a Conveniently location close to healthy centers, excellent schools, restaurants and shopping with easy access to Costco, Walmart, and various dining options. Only 4 miles from Winter Park SunRail Train Station and 20 minutes from Orlando International Airport.This unit offers a cozy living/dining area with sliding

  Maria Batista LPT REALTY, LLC

  126 Scottsdale Square Unit B126, Winter Park, FL 32792
• 

  

  /32

  $695,000

  • 3 Beds
  • 2 Baths
  • 2,193 Sq Ft

  1427 Lake Florence Way, Winter Park, FL 32792

  Welcome to this beautifully maintained, Stunning Better-Than-New 6-Year-Old Custom Home in Gated Lake FlorencePreserve, one-owner custom home that truly has it all. From the moment you enter, you’ll appreciate the exceptional quality and craftsmanship, including upgraded 8' interior doors, 10-foot ceilings, crown molding, and elegant tray ceilings throughout—even in the primary suite. One of

  Doug Addeo COMMUNITY REALTY ASSOCIATES

  1427 Lake Florence Way, Winter Park, FL 32792
• 

  

  /17

  $398,000

  • 3 Beds
  • 2 Baths
  • 1,405 Sq Ft

  616 Ellendale Dr, Winter Park, FL 32792

  Desirable Winter Park Estates - close to everything! Beautifully updated 3 Bedroom 2 Bath POOL home which is located in a highly desirable school district! Updated Contemporary Kitchen has newer Cabinetry, newer Stainless-Steel appliances, and Granite countertops which connect with the open Living room. Dining area extends to the generous size Family room - Ideal for Entertaining. The home has a

  David Ruiz CENTRAL REALTY

  616 Ellendale Dr, Winter Park, FL 32792
• 

  

  /29

  $250,000

  • 2 Beds
  • 2 Baths
  • 1,087 Sq Ft

  1601 Grove St Unit 552, Maitland, FL 32751

  One or more photo(s) has been virtually staged. **2024 ROOF** Discover this stunning, newly renovated one story end unit boasting over 1,000 sq ft of modern living space. This spacious 2 bedroom, 2 bath condo features luxury vinyl plank flooring throughout, a stylish new kitchen with white shaker cabinets, quartz countertops, and stainless steel appliances, plus all new light fixtures and fresh

  Chris Creegan CREEGAN GROUP

  1601 Grove St Unit 552, Maitland, FL 32751
• 

  

  /55

  $1,300,000

  • 4 Beds
  • 2.5 Baths
  • 2,116 Sq Ft

  1421 Sunnyside Dr, Maitland, FL 32751

  Welcome to 1421 Sunnyside Drive in Maitland, a beautifully maintained home where timeless design meets modern luxury. This 4-bedroom, 2.5-bath corner lot residence with a pool has a thoughtfully designed indoor and outdoor living space. Its location provides quick access to top-rated schools, boutique shopping, and local dining in one of the most desirable neighborhoods in the Maitland and Winter

  Amanda Binns STRICKLAND REALTY GROUP INC

  1421 Sunnyside Dr, Maitland, FL 32751
• 

  

  /47

  $2,885,000

  • 5 Beds
  • 5 Baths
  • 4,001 Sq Ft

  1411 Nottingham St, Orlando, FL 32803

  This one-of-a-kind, top-tier custom contemporary home in coveted Beverly Shores/Rose Isle delivers true turnkey luxury with exceptional finishes, premium cabinetry, high-end appliances, and fully integrated smart features throughout. The five-bedroom, three-and-a-half-bath main home plus a detached 384 SF casita (sixth bedroom) sits on a premium lot with unmatched access to scenic Mead

  Gwyn Clark FANNIE HILLMAN & ASSOCIATES

  1411 Nottingham St, Orlando, FL 32803
• 

  

  /50

  $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. Lot Size: 14,331 Sq Ft / 1,331 SqM. This home features a modern kitchen with a marble Breakfast bar and marble countertops, an Open floor plan with lots of natural light. New White-Oak wood floors installed throughout in September 2025. The huge primary Bedroom suite with sitting

  Pamela Stewart REALCOM REAL ESTATE SERVICES INC

  1901 Lake Sue Dr, Orlando, FL 32803
• 

  

  /42

  $285,000

  • 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 and

  Wendy Aldana LLC NETWORTH REALTY OF ORLANDO, LLC

  1618 Gulfview Dr Unit 417, Maitland, FL 32751

Showing Results 161 - 181, Page 5 of 5