Winter Park, FL Homes for Sale with Pool

• 

  

  

  /56

  $530,000

  • 4 Beds
  • 2 Baths
  • 2,092 Sq Ft

  2217 Sussex Rd, Winter Park, FL 32792

  4 BEDROOMS with OFFICE POOL HOME. MOTIVATED SELLERS. MOVE IN READY! THIS HOME WILL NOT LAST! COME, SEE AND BRING YOUR OFFERS TODAY!This home boasts a large open concept as you walk in from the front door. Tons of natural lighting. Kitchen equipped with modern appliances, granite counter tops, and lots of cabinets for storage. Woodburning fireplace. Pool view from the masterbedroom. Large

  Thess Hubilla PREFERRED REAL ESTATE BROKERS

  2217 Sussex Rd, Winter Park, FL 32792
• 

  

  

  /20

  $225,000

  • 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
• 

  

  

  /26

  $165,000

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft

  3315 Amber Wood Way Unit 104, Winter Park, FL 32792

  Terrific townhome in the Hidden Oaks community offers an updated interior & it's own privacy fenced patio! Step inside to the bright and spacious living/dining combo w/lovely wood laminate flooring & wet bar, galley style kitchen w/breakfast area, laundry closet w/full size washer & dryer, and 2 terrific bedrooms-one with oversized walk-in closet. Storage under the stairs and in AC closet. Enjoy

  Robert Sinclair 100% REAL ESTATE, INC

  3315 Amber Wood Way Unit 104, Winter Park, FL 32792
• 

  

  

  /35

  $249,900

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 228, Winter Park, FL 32789

  Attention lake enthusiasts! This is your opportunity to enjoy true waterfront living without the cost or maintenance typically associated with it. Located on beautiful Lake Killarney in sought-after Winter Park you will enjoy an array of amenities including a private boat ramp, a large open boat dock where you can feed the fish and turtles, picnic areas, clubhouse and resort style community pool

  Lora King HOMEVEST REALTY

  2500 Lee Rd Unit 228, Winter Park, FL 32789
• 

  

  

  /36

  $319,000

  • 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
• 

  

  /44

  $795,000

  • 2 Beds
  • 2 Baths
  • 1,832 Sq Ft

  1702 Glenridge Way, Winter Park, FL 32789

  Rare opportunity in Winter Park to own a move-in-ready, fully renovated corner lakefront townhome in an intimate community of only sevenresidences on Lake Spier. This is the kind of waterfront lifestyle that rarely comes to market: peaceful lake views, direct access to the water forkayaking or paddleboarding, and a community pool just steps away, all minutes from Park Avenue dining,

  Romain Liberman BHHS EWM Realty

  1702 Glenridge Way, Winter Park, FL 32789
• 

  

  /70

  $1,634,900 New Construction

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

  1510 Miller Ave, Winter Park, FL 32789

  New Construction – JUST COMPLETED! Discover Modern Luxury in Winter Park's Latest Neighborhood, Winter Park Grove! Step into a world of refined living with this breathtaking new construction pool home, located in the vibrant heart of Winter Park. Just moments away from the eclectic energy of Park Avenue, this modern masterpiece seamlessly blends sophistication, style, and convenience — all within

  Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  1510 Miller Ave, Winter Park, FL 32789
• 

  

  /50

  $1,824,900 Open Sun 1PM - 3PM

  • 5 Beds
  • 7 Baths
  • 3,116 Sq Ft

  1861 Taylor Ave, Winter Park, FL 32789

  PRICE IMPROVEMENT! This exceptional custom residence, built by Meridian Homes and designed by Zero Latitude, offers a rare combination of thoughtful architecture, high-end finishes, and modern functionality. Interior design by Lauren Ayers Interiors sets a refined tone throughout, complemented by curated details such as Rifle Paper wallpaper, accent walls, and wide-plank hardwood flooring by

  Kevin Kelly FANNIE HILLMAN & ASSOCIATES

  1861 Taylor Ave, Winter Park, FL 32789
• 

  

  /18

  $4,199,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,891 Sq Ft

  1417 Williams Dr, Winter Park, FL 32789

  Under Construction. Tucked away on a quiet cul-de-sac in the coveted Park Grove community, this home sits on an expansive 0.37-acre lot, just moments from the boutiques, dining, and charm of Park Avenue. The exterior makes a striking first impression with a refined architectural façade that feels both timeless and distinctive. Inside, a dramatic 20-foot foyer welcomes you with abundant natural

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1417 Williams Dr, Winter Park, FL 32789
• 

  

  /25

  $250,000

  • 2 Beds
  • 2 Baths
  • 927 Sq Ft

  205 Lewfield Cir Unit 205, Winter Park, FL 32792

  Wonderful! Exceptional Winter Park location! Amenities include 2 pools, lighted tennis courts, fitness center, car care facilities & clubhouse, enjoy the simple life in this 2 bedroom, 2 bath, ground floor unit. Sip your morning coffee while admiring the garden landscaping from your screen enclosed patio. Host a barbeque with family and friends at the community clubhouse or enjoy shopping at the

  Eimi Moreno Carrera LPT REALTY, LLC

  205 Lewfield Cir Unit 205, Winter Park, FL 32792
• 

  

  /20

  $215,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  151 N Orlando Ave Unit 226, Winter Park, FL 32789

  Take advantage of this newly updated 2 Bedrooms and 1 Bathroom LAKE FRONT condo conveniently located in Winter Park/Orlando next to all of shops and restaurants. With private lake access to launch and dock your watercraft within the community for boating and fishing. Walk to Trader Joes next door and Winter Park Village to enjoy great number of restaurants, movie theater, retail shops and grocery

  Mike Wang LOKATION

  151 N Orlando Ave Unit 226, 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
• 

  

  /49

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 1,402 Sq Ft

  1602 Alabama Dr Unit 403, Winter Park, FL 32789

  Perched on the top floor in the heart of Winter Park, this luxury, open-concept residence offers a rare blend of elevated design and everyday ease. Enjoy the peace of no neighbors above, plus the privacy, security, and lock-and-leave convenience that only condo living can provide without sacrificing space, light, or lifestyle. The Alabama delivers a rare Winter Park combo of modern living and

  Matthew Burks CORCORAN PREMIER REALTY

  1602 Alabama Dr Unit 403, Winter Park, FL 32789
• 

  

  /68

  $948,000

  • 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
• 

  

  /19

  $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
• 

  

  /60

  $2,100,000

  • 5 Beds
  • 3 Baths
  • 3,669 Sq Ft

  1711 Barcelona Way, Winter Park, FL 32789

  Walk in and feel instantly at home in this stunning 5-bedroom, 3-bath POOL home with a 3-car garage, offering over 3,600 square feet of living space on more than 3⁄4 of an acre in the highly desirable Sevilla neighborhood of Winter Park. Backing directly to Howell Creek and Mead Gardens, this property offers the rare luxury of no rear neighbors and exceptional privacy. Upon entry, you’re welcomed

  Lindsay Kaye Voss VOSS REALTY INC

  1711 Barcelona Way, 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

  $389,000

  • 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
• 

  

  /3

  $3,795,000 New Construction

  • 5 Beds
  • 6 Baths
  • 4,247 Sq Ft

  1681 Blue Ridge Rd, Winter Park, FL 32789

  Pre-Construction. To be built. Build your dream home with premier custom home builder, FG Schaub Custom Homes on this highly desirable Winter Park homesite. Located at 1681 Blue Ridge Rd., this thoughtfully designed new construction Transitional-style residence will feature 5 bedrooms plus a dedicated office, 4 full bathrooms, 2 half bathrooms, 4,272 square feet of living space, and a 3-car

  Laura Earl CORCORAN PREMIER REALTY

  1681 Blue Ridge Rd, Winter Park, FL 32789
• 

  

  /55

  $171,000

  • 2 Beds
  • 2 Baths
  • 927 Sq Ft

  256 Lewfield Cir Unit 256, Winter Park, FL 32792

  This charming and well-maintained 2 bedroom, second-floor condo in Winter Park is ready for you to call your own! The home features comfortable carpeted living areas throughout. The centrally located galley kitchen offers plenty of cabinet and counter space and connects directly to the dining room. The spacious living room gets plenty of natural light through large sliding glass doors, opening to

  Renee Kumar LLC LA ROSA REALTY LLC

  256 Lewfield Cir Unit 256, Winter Park, FL 32792
• 

  

  /25

  $499,500

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  1280 Gladiolas Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedroom, 2-bath home with a screened-in pool, ideally located in the heart of Winter Park. Step inside to a fresh, move-in-ready feel with new flooring throughout, new light fixtures, new windows, and new doors—all thoughtfully selected to give the home a clean, modern look. The open, inviting layout is perfect

  Ian Trumbach FLORIDA PRESTIGIOUS HOMES INC

  1280 Gladiolas Dr, Winter Park, FL 32792
• 

  

  /10

  $1,689,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,604 Sq Ft

  1810 Hollywood Ave, Winter Park, FL 32789

  Under Construction. Estimated completion August!! Experience modern luxury living in the heart of Winter Park with this beautifully designed pool home at 1810 Hollywood Avenue. Offering 4 bedrooms, 3.5 bathrooms, and 2,604 square feet of thoughtfully planned living space, this residence blends high-end finishes with everyday functionality in one of Central Florida’s most sought-after locations.

  Ken Pozek REAL BROKER, LLC

  1810 Hollywood Ave, Winter Park, FL 32789
• 

  

  /32

  $495,000

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  346 S Ranger Blvd, Winter Park, FL 32792

  PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone

  Tetyana Vyushkina IMPERIAL REALTY OF FLORIDA INC

  346 S Ranger Blvd, Winter Park, FL 32792
• 

  

  /73

  $3,549,995

  • 4 Beds
  • 5 Baths
  • 3,658 Sq Ft

  1742 Temple Dr, Winter Park, FL 32789

  A New Standard of Modern Sophistication in Winter ParkIn a city known for its heritage, this ground-up architectural renovation emerges as a bold statement of modern luxury. Located within one of Winter Park’s most coveted enclaves, this four-bedroom, five-bathroom residence is not merely a place to live, but a meticulously crafted experience where high-design meets intuitive living.Step

  Mark Anthony Buot ROI AVE LLC

  1742 Temple Dr, Winter Park, FL 32789
• 

  

  /29

  $249,000

  • 3 Beds
  • 2 Baths
  • 1,256 Sq Ft

  602 Villa Cir Unit 543, Maitland, FL 32751

  Experience the pinnacle of worry-free living in this stunningly renovated, single-story villa located in the highly desirable Park Lake community of Maitland. This home has been meticulously updated with a focus on efficiency and modern luxury, featuring brand-new energy-efficient sliding glass doors (2025), new Roof, new solid wood bedrm and closet doors, New plantation shutters (2024), new AC

  Odel Ximinies COLDWELL BANKER RESIDENTIAL RE

  602 Villa Cir Unit 543, Maitland, FL 32751
• 

  

  /59

  $1,224,999

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

  1421 Sunnyside Dr, Maitland, FL 32751

  One or more photo(s) has been virtually staged. HUGE PRICE IMPROVEMENT Welcome to 1421 Sunnyside Drive, Maitland, FL, a beautifully maintained 4-bedroom, 2.5-bath single-family home with a pool, located on a corner lot directly adjacent to Winter Park. While this home carries a Maitland address, it sits just steps from Winter Park homes, offering the best of both locations. This move-in-ready

  Amanda Binns STRICKLAND REALTY GROUP INC

  1421 Sunnyside Dr, Maitland, FL 32751
• 

  

  /47

  $2,785,000

  • 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

Showing Results 161 - 190, Page 5 of 5