Winter Park, FL Homes

• 

  

  

  /19

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,214 Sq Ft

  3117 Shady Pine Ave, Winter Park, FL 32792

  Impeccably maintained and extensively updated, this 3-bedroom, 2-bath home is located in a quiet, established Winter Park neighborhood with no HOA. Recent improvements include brand-new luxury vinyl plank flooring throughout (August 2025), fresh interior paint, a fully remodeled guest bathroom (2024), updated kitchen accessories, and a paver driveway added in 2021. Major systems have been

  Alistair Baxter EXP REALTY LLC

  3117 Shady Pine Ave, Winter Park, FL 32792
• 

  

  

  /14

  $2,495 per month

  • 3 Beds
  • 2 Baths
  • 1,405 Sq Ft
  • House for Rent

  2631 Ambergate Rd, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2639.90. That covers your base rent, $2495.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  2631 Ambergate Rd, Winter Park, FL 32792
• 

  

  /2

  $415,000 Sold Aug 08, 2025

  • 1,639 Sq Ft
  • $253/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1979

  7040 Betty St, Winter Park, FL 32792

  **WATCH THE VIDEO TOUR!!** You’ll love the HUGE BACKYARD (0.3 ACRE LOT) & 4TH BONUS ROOM! Nestled in one of Winter Park's established neighborhoods with NO HOA! The backyard features mature landscaping and peaceful sunset views every night! Enjoy 3 bedrooms plus a 4th ROOM HOME OFFICE with a french door, offering flexibility as a dedicated workspace or turn into a bedroom! Major updates include

  Cece Wong EXP REALTY LLC

  7040 Betty St, Winter Park, FL 32792
• 

  

  

  /33

  Est $435,406 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2003 Canny Cove, Winter Park, FL 32792

  2003 Canny Cove, Winter Park, FL 32792
• 

  

  

  /60

  $2,329,000

  • 5 Beds
  • 4 Baths
  • 4,328 Sq Ft

  715 Via Bella, Winter Park, FL 32789

  Tucked away on a quiet cul-de-sac lined with multi-million-dollar estates, this Winter Park residence offers an enviable blend of privacy, lifestyle, and location. Less than a mile from Park Avenue, the Winter Park 9 Golf Course, and the Racquet Club, this address puts you at the center of the city’s most coveted amenities. A deeded greenbelt easement to Lake Osceola—just 100 yards from the front

  Adam Roark COMPASS FLORIDA LLC

  715 Via Bella, Winter Park, FL 32789
• 

  

  /20

  $1,705 per month

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Condo for Rent

  851 Miles Ave Unit 8, Winter Park, FL 32789

  UNBELIEVABLE PRICE DROP! This gorgeous 2 bedroom 1 bathroom condo is ready to go, and priced for you! This unit is a second floor corner condo, located in the serene and peaceful Aragon Condo community. Centrally located in Winter Park, only 5 minutes to downtown, Rollins College, Orlando Health and so much more. Featuring an open floor plan, stainless steel appliances, wood flooring throughout,

  Michael Mones LPT REALTY, LLC

  851 Miles Ave Unit 8, Winter Park, FL 32789
• 

  /2

  $875,000 Sold Aug 08, 2025

  • 3,158 Sq Ft
  • $277/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  7801 Georgeann St, Winter Park, FL 32792

  MAJOR PRICE IMPROVEMENT! Live the Winter Park LAKEFRONT dream with this stunning 3-bedroom, 2-bath home on skiable LAKE WAUNATTA, offering breathtaking water views and endless amenities and NO HOA! The entire second floor is dedicated to the luxurious primary suite, complete with a spacious office, oversized closets, enjoy your morning coffee or evening glass of wine on your private balcony

  Kelly Butterfield RE/MAX TOWN & COUNTRY REALTY

  7801 Georgeann St, Winter Park, FL 32792
• 

  

  /55

  Est $1,064,403 Not Listed For Sale

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

  1772 Mondrian Cir, Winter Park, FL 32789

  1772 Mondrian Cir, Winter Park, FL 32789
• 

  

  /32

  $179,900

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  224 Lewfield Cir Unit 224, Winter Park, FL 32792

  Welcome to low-maintenance living in the heart of desirable Winter Park! This charming 2-bedroom, 2-bathroom second-floor condo offers a thoughtfully designed layout and an unbeatable location just minutes from everything Central Florida has to offer.Step inside to find spacious living and dining areas filled with natural light, creating a warm and inviting atmosphere for both everyday

  Chris Creegan CREEGAN GROUP

  224 Lewfield Cir Unit 224, Winter Park, FL 32792
• 

  /2

  $3,049 per month

  • 4 Beds
  • 2 Baths
  • 2,018 Sq Ft
  • House for Rent

  2536 Eastbrook Blvd, Winter Park, FL 32792

  A Pool Maintenance Fee of $150 per month applies to any home with a private pool.Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.0 bathrooms,

  2536 Eastbrook Blvd, Winter Park, FL 32792
• 

  /2

  $379,900 Sold Aug 08, 2025

  • 1,503 Sq Ft
  • $253/SF
  • 57 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1967

  3121 Thistlehill Dr, Winter Park, FL 32792

  Excellent value on this 3BR corner lot home in the well-established Georgetown Estates community of Winter Park. Recent quality updates include: (1) Roof new in 2023, (2) Replumbed in 2024, (3) New garage door in 2025, (4) Fresh exterior paint in 2025, (5) Fresh interior paint (bedrooms, baths, kitchen) in 2025, and (6) Bedroom carpeting new in 2025. Layout features spacious living room upon

  Mark Ramey EXP REALTY LLC

  3121 Thistlehill Dr, Winter Park, FL 32792
• 

  

  /19

  Est $239,502 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft

  200 Saint Andrews Blvd Unit 1807, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 1807, Winter Park, FL 32792
• 

  /2

  $1,690,000

  • 2 Beds
  • 1 Bath
  • 1,559 Sq Ft

  141 W Lake Sue Ave, Winter Park, FL 32789

  AMAZING Winter Park Opportunity! Nestled in one of the most desirable locations, 141 W Lake Sue Avenue offers a VERY HARD to find 1⁄2 acre lot—the epitome of prime real estate. The true value lies in the land, making this a rare chance for builders or buyers to create their dream Winter Park residence. Surrounded by beautiful homes and tree-lined streets, this pristine lot provides the perfect

  Brian Mitnik RE/MAX 200 REALTY

  141 W Lake Sue Ave, Winter Park, FL 32789
• 

  

  /15

  $1,840 per month

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft
  • Condo for Rent

  7429 Daniel Webster Dr Unit 14 (C), Winter Park, FL 32792

  Welcome to this enchanting fully furnished 2-bedroom, 2-bathroom condo nestled in the heart of Winter Park, FL! Offering easy access to a plethora of attractions, this home invites you to immerse yourself in the magic of Disney, just 30 minutes away, or bask in the sun at picturesque Cocoa Beach, all within reach of central Florida's vibrant offerings. Strategically positioned minutes from the

  David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

  7429 Daniel Webster Dr Unit 14 (C), Winter Park, FL 32792
• 

  /2

  $360,000 Sold Aug 08, 2025

  • 1,240 Sq Ft
  • $290/SF
  • 104 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  1612 Eastbrook Blvd, Winter Park, FL 32792

  **Back on the Market due to buyer financing falling through & listed for below market value!****Owner Financing Available!!**Welcome to this charming Winter Park home, perfectly situated at 1612 Eastbrook Blvd. This 1,240 square foot residence offers three bedrooms and two bathrooms, making it an ideal space for comfortable family living.Step inside to discover high

  Justin Adams EXP REALTY LLC

  1612 Eastbrook Blvd, Winter Park, FL 32792
• 

  

  /43

  Est $780,586 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,496 Sq Ft

  7984 Pleasant Pine Cir, Winter Park, FL 32792

  7984 Pleasant Pine Cir, Winter Park, FL 32792
• 

  

  /52

  $1,200,000

  • 2 Beds
  • 2 Baths
  • 1,220 Sq Ft

  100 S Interlachen Ave Unit 404, Winter Park, FL 32789

  Welcome to The Cloisters, an exclusive lakefront enclave located in the heart of Winter Park, offering a rare combination of walkability, lakefront serenity, and bespoke design. Situated on the fourth floor, this fully reimagined residence is the result of a meticulous, full-scale renovation by W Designs LTD and has never been occupied.A striking entry sets the tone with a black-and-white

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 404, Winter Park, FL 32789
• 

  

  /16

  $3,850 per month

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft
  • House for Rent

  423 Ololu Dr, Winter Park, FL 32789

  Property Id: 2129677Ready to move-in! This fully furnished home offers comfort, space, and style perfect for families or professionals seeking a turnkey rental in a premium location.Home Features: * 3 Bd | 3 Full BR Including a luxurious master suite with walk-in closet * Fully Furnished Option Available with $4,100 rent * Beautiful Updated Kitchen Featuring newer

  423 Ololu Dr, Winter Park, FL 32789
• 

  /2

  $341,000 Sold Aug 08, 2025

  • 1,568 Sq Ft
  • $217/SF
  • 205 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1956

  2827 Euston Rd, Winter Park, FL 32789

  Welcome to 2827 Euston Rd, a beautifully updated home in the highly desirable Winter Park area with the added bonus of no HOA! This charming residence offers 3 beds, 2baths, and a versatile bonus room that can be used as an office, playroom, or additional living space.The master suite is thoughtfully separated from the other two bedrooms, providing privacy and convenience. Inside, you’ll

  Evelyn Tejada REGENCY REAL ESTATE LLC

  2827 Euston Rd, Winter Park, FL 32789
• 

  

  /40

  Est $805,326 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,706 Sq Ft

  2035 Soaring Oak Way, Winter Park, FL 32792

  2035 Soaring Oak Way, Winter Park, FL 32792
• 

  

  /15

  $165,000

  • 1 Bed
  • 1 Bath
  • 749 Sq Ft

  3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792

  Prime Location and Zip Code are key! Low HOA! Welcome home to 3019 Antique Oaks Circle Unit 124 at Parkview Village Winter Park, FL. This well-maintained community offers mature landscaping and scenic views. This beautiful 1-bedroom, 1-bathroom condo in the heart of Winter Park, Florida has become available and ready to receive a new owner. Located on the second floor, the home offers a quiet,

  Kelly Flores COLDWELL BANKER REALTY

  3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792
• 

  

  /34

  $1,924 per month

  • 2 Beds
  • 2 Baths
  • 1,236 Sq Ft
  • Townhouse for Rent

  5167 Lazy Oaks Dr, Winter Park, FL 32792

  Lovely 2 bed/ 2 ba condo in the heart of Winter Park. Beautiful wooden vinyl flooring throughout the first floor. Spacious living room! Bedrooms on the second floor. Beautiful master bathroom with a granite countertop. Screened-in porch, perfect for rainy days! Nearby restaurants, entertainment, shops, and major highways!*Washer and Dryer Included!**Lawn Care Included (through

  Jason Hamilton THE REALTY MEDICS

  5167 Lazy Oaks Dr, Winter Park, FL 32792
• 

  /2

  $158,000 Sold Aug 08, 2025

  • 1,031 Sq Ft
  • $153/SF
  • 176 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1984

  3390 Cedar Springs Place Unit 163, Winter Park, FL 32792

  Short Sale. Contingent on Lender Approval . Discover this charming 2-bedroom, 2-bath townhouse-style condo in the highly sought-after Winter Park area. This move-in ready home features beautiful ceramic Spanish-style tiles and laminate wood flooring throughout. You'll love the updated kitchen and bathrooms, as well as the spacious fenced-in patio/lanai with additional outdoor storage for your

  Elena Santiago THE REAL ESTATE COLLECTION LLC

  3390 Cedar Springs Place Unit 163, Winter Park, FL 32792
• 

  

  /25

  Est $249,000 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,439 Sq Ft

  5408 Peaco Place, Winter Park, FL 32792

  5408 Peaco Place, Winter Park, FL 32792
• 

  

  /27

  $158,500

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft

  150 Lewfield Cir Unit 150, Winter Park, FL 32792

  Enjoy Winter Park lifestyle in this fabulous 1 bedroom, 1 bath condo. Built in 1973 with a clean and well-planned 678 sq.ft. Floor plan. Featuring a seamless mix of hardwood flooring and carpeting, this home offers a welcoming atmosphere that’s both functional and inviting. The kitchen comes fully equipped with a stove, refrigerator, and microwave, making meal prep effortless from day one. The

  Randall Shirey CHARLES RUTENBERG REALTY ORLANDO

  150 Lewfield Cir Unit 150, Winter Park, FL 32792
• 

  

  /17

  $2,269 per month

  • 3 Beds
  • 2 Baths
  • 1,578 Sq Ft
  • House for Rent

  7116 Green Needle Dr, Winter Park, FL 32792

  Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,578 square feet, this well-maintained home offers a high standard of

  7116 Green Needle Dr, Winter Park, FL 32792
• 

  /2

  $1,065,000 Sold Aug 07, 2025

  • 3,057 Sq Ft
  • $348/SF
  • 1 Day On Market

  • 4 Beds
  • 3 Baths
  • Built 2021

  1024 Wading Waters Cir, Winter Park, FL 32792

  Welcome to 1024 Wading Waters Circle—a rare offering in the gated, amenity-rich enclave of Hawk's Crest in Winter Park. This modern, single-story Palermo II model has been elevated far beyond builder-grade materials with over $300,000 in custom upgrades, blending refined design with seamless indoor-outdoor living and spectacular waterfront views. From the moment you arrive, this residence

  Harif Hazera PREMIER SOTHEBY'S INTL. REALTY

  1024 Wading Waters Cir, Winter Park, FL 32792
• 

  

  /16

  Est $1,026,075 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,110 Sq Ft

  2400 Roxbury Rd, Winter Park, FL 32789

  2400 Roxbury Rd, Winter Park, FL 32789
• 

  

  /51

  $1,285,000

  • 4 Beds
  • 2 Baths
  • 2,750 Sq Ft

  1981 Blue Ridge Rd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**Welcome home to this beautifully renovated 4-bedroom, 2-bathroom home nestled on a desirable corner lot in the heart of Winter Park’s Timberlane Shores community. Boasting

  Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  1981 Blue Ridge Rd, Winter Park, FL 32789
• 

  

  /44

  $4,850 per month

  • 4 Beds
  • 4 Baths
  • 3,714 Sq Ft
  • House for Rent

  1710 Oakhurst Ave, Winter Park, FL 32789

  Gorgeous 4 bed + 4 bath custom built home with numerous upgrades throughout. Separate formal living & dining rooms plus kitchen opens to family room for entertaining. Fantastic kitchen with solid wood cabinets, granite counters, stainless appliances, 5 burner stove & double ovens. Indoor laundry room with newer washer & dryer provided. Spacious & private downstairs master suite with closet

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  1710 Oakhurst Ave, Winter Park, FL 32789
• 

  /2

  $260,000 Sold Aug 07, 2025

  • 1,080 Sq Ft
  • $241/SF
  • 18 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  3015 Casselwood St, Winter Park, FL 32792

  Welcome to this beautifully maintained 3-bedroom, 2-bath villa nestled in the highly sought-after community of Winter Park! This spacious home boasts an open floor plan, a convenient inside laundry room, and easy-to-maintain flooring—no carpet anywhere, and Solar panels! Step outside to a generously sized screened-in patio, perfect for relaxing or entertaining. Enjoy warm Florida days at the

  Michelle Parrish PARRISH REALTY GROUP INC

  3015 Casselwood St, Winter Park, FL 32792
• 

  

  /19

  Est $2,474,476 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,205 Sq Ft

  350 Beloit Ave, Winter Park, FL 32789

  350 Beloit Ave, Winter Park, FL 32789
• 

  

  /28

  $358,000

  • 3 Beds
  • 2 Baths
  • 1,114 Sq Ft

  1827 Blaine Terrace, Winter Park, FL 32792

  Welcome to this beautifully renovated 3-bedroom, 2-bath home in the Villas of Casselberry. Inside, you’ll find a bright and functional floor plan with comfortable living spaces, a convenient 1-car garage, and extra outside storage. Thoughtful updates throughout make this home move-in ready from day one. New roof 6/2025, new driveway, fenced in back yard, new kitchen with quartz countertops, vinyl

  Mario Zendeli COMPASS FLORIDA LLC

  1827 Blaine Terrace, Winter Park, FL 32792
• 

  

  /20

  $1,645 per month

  • 2 Beds
  • 2.5 Baths
  • 1,230 Sq Ft
  • Condo for Rent

  7296 Daniel Webster Dr Unit 1, Winter Park, FL 32792

  Welcome to 7296 Daniel Webster Dr Unit 1, a spacious and well-kept 2-bedroom, 2.5-bath townhome offering 1,230 sq ft of comfortable living in the heart of Winter Park. The main floor features a bright living and dining area with wood-style flooring, a half bath, a dedicated laundry room with washer/dryer hookups, and a beautifully updated kitchen with rich wood cabinetry, granite countertops, and

  7296 Daniel Webster Dr Unit 1, Winter Park, FL 32792
• 

  /2

  $450,000 Sold Aug 07, 2025

  • 1,634 Sq Ft
  • $275/SF
  • 87 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  5326 Lanyard Ct, Winter Park, FL 32792

  Discover your dream home in Winter Park! This stunning 3-bedroom, 2-bathroom gem sits on a spacious 1/3-acre lot, offering the perfect blend of comfort, style, and outdoor living. Step inside to an inviting open-concept layout, where natural light floods the living, dining, and kitchen areas, creating an ideal space for entertaining or cozy nights. The modern kitchen boasts sleek appliances and

  Deborah Summers CHARLES RUTENBERG REALTY ORLANDO

  5326 Lanyard Ct, Winter Park, FL 32792
• 

  

  /35

  Est $307,198 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft

  228 Balfour Dr Unit 17, Winter Park, FL 32792

  228 Balfour Dr Unit 17, Winter Park, FL 32792
• 

  

  /66

  $4,650,000

  • 4 Beds
  • 4.5 Baths
  • 4,181 Sq Ft

  1161 Valencia Ave, Winter Park, FL 32789

  Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Completed in 2021, the residence has 4,181 square feet of thoughtfully designed living space, including four bedrooms each with a private ensuite bath and an additional powder room. A 412-square-foot casita with a

  Lisa Mahjoub THE REAL ESTATE COLLECTION LLC

  1161 Valencia Ave, Winter Park, FL 32789
• 

  

  /42

  $2,300 per month

  • 3 Beds
  • 2 Baths
  • 1,950 Sq Ft
  • House for Rent

  7733 Fox Knoll Place, Winter Park, FL 32792

  Welcome to this stunning 3-bedroom, 2-bathroom home in the wonderful Winter Park! Step inside and discover a beautiful living space with freshly painted walls, giving the home a modern and inviting atmosphere.This home has no carpet throughout. Instead, the floors are adorned with elegant and easy-to-maintain flooring, adding a touch of sophistication to every room.The home boasts a second

  Jason Hamilton THE REALTY MEDICS

  7733 Fox Knoll Place, Winter Park, FL 32792
• 

  /2

  $423,000 Sold Aug 07, 2025

  • 1,907 Sq Ft
  • $222/SF
  • 87 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2024

  2812 Bright Bird Ln, Winter Park, FL 32792

  Built in 2024, this move-in ready 3-bedroom, 2.5-bathroom townhome is located in the gated community of Grayson Square, just a little over 15 minutes from Park Avenue in downtown Winter Park. Designed with a sleek, neutral gray color scheme and modern finishes throughout, the home features an open-concept layout filled with natural light that enhances its bright and airy feel. The main level

  Jessica Snyder LPT REALTY, LLC

  2812 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /80

  Est $1,176,302 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,307 Sq Ft

  1999 Soaring Oak Way, Winter Park, FL 32792

  1999 Soaring Oak Way, Winter Park, FL 32792

Showing Results 401 - 440, Page 11 of 18