Winter Park, FL Homes

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  /30

  $695,000

  • 3 Beds
  • 2 Baths
  • 1,167 Sq Ft

  726 N Pennsylvania Ave, Winter Park, FL 32789

  Welcome to this beautifully designed 3-bedroom, 2-bathroom home, offering a blend of modern elegance and prime location. The gourmet kitchen boasts 42” black cabinets, granite countertops, a decorative backsplash, and stainless steel appliances, making it a stunning focal point of the home. The open-concept dining and living room create a spacious feel, while ceramic tile and wood floors enhance

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  726 N Pennsylvania Ave, Winter Park, FL 32789
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  /20

  $1,284 - $2,811 per month

  ARIUM Winter Park

  1 - 2 Beds

  3250 Bishop Park Dr, Winter Park, FL 32792

  Your home oasis awaits at ARIUM Winter Park with our upscale amenities and open-concept 1 and 2-bedroom apartments for rent. Minutes from downtown Winter Park and Orlando's hot spots, our community provides the perfect place to call home.Soak up the sun at our resort-style pool and outdoor kitchen, de-stress in our fitness center, or bring your canine companion to explore our dog

  3250 Bishop Park Dr, Winter Park, FL 32792
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  /2

  $1,300,000 Sold Sep 22, 2025

  1371 Lyndale Blvd, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,714 Sq Ft
  • Built 1949

  Last Sold Summary

  • 4% Below List Price
  • $479/SF
  • 8 Days On Market

  Current Estimated Value $1,283,867

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1371 Lyndale Blvd, Winter Park, FL 32789
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  /18

  Est $251,123 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,227 Sq Ft

  7781 Country Place Unit J-1, Winter Park, FL 32792

  7781 Country Place Unit J-1, Winter Park, FL 32792
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  /29

  $389,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,401 Sq Ft

  1670 Clematis Ln, Winter Park, FL 32792

  This stunning home has been completely renovated and is ready for you to move in! Featuring 3 bedrooms, 2 full bathrooms, and a screened-in pool with a spacious deck, it blends modern style with everyday comfort. Inside, you’ll find brand-new waterproof laminate flooring, fresh paint throughout, and stylish modern finishes that create a light and inviting atmosphere. The open and spacious common

  Gea Gomez LPT REALTY, LLC

  1670 Clematis Ln, Winter Park, FL 32792
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  /32

  $1,595 per month

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft
  • Condo for Rent

  200 Saint Andrews Blvd Unit 1803, Winter Park, FL 32792

  2-bedroom, 1.5-bathroom, two-story condo in Four Seasons Condos of Winter Park. This well maintained condo includes a French country kitchen, which has been renovated with a faux tiled backsplash, custom maple cabinets, and complimentary appliances. This unit includes a half bath downstairs and full bathroom upstairs. Windows are double-pane, double-hung with a Pella sliding glass door with

  Amy Spano WILSON MANAGEMENT GROUP

  200 Saint Andrews Blvd Unit 1803, Winter Park, FL 32792
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  /2

  $421,700 Sold May 29, 2025

  1189 Lazy Hollow Place, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,525 Sq Ft
  • Built 1984

  Last Sold Summary

  • $277/SF
  • 7 Days On Market

  Current Estimated Value $420,503

  Last Listing Agent Virginia Silberstein ORLANDO EXPERT REALTY LLC

  1189 Lazy Hollow Place, Winter Park, FL 32792
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  /17

  Est $191,280 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  7460 Swallow Run Unit 42, Winter Park, FL 32792

  7460 Swallow Run Unit 42, Winter Park, FL 32792
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  /43

  $429,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,605 Sq Ft

  2833 Prince John Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. Needs TLC. Property is being sold as-is. Age of big ticket items unknown. Buyer/buyer's agent to verify condition of property via walkthrough. Limited-service listing - Please see realtor remarks for showing instructions.

  Makena Clark EXIT REALTY PREMIER LEGACY

  2833 Prince John Rd, Winter Park, FL 32792
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  /14

  $2,390 per month

  • 3 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • House for Rent

  5206 Ardmore Dr, 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 $2534.90. That covers your base rent, $2390.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  5206 Ardmore Dr, Winter Park, FL 32792
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  /2

  $405,000 Sold Jan 09, 2026

  3425 Ferndell Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft
  • Built 1966

  Last Sold Summary

  • 5% Below List Price
  • $267/SF
  • 164 Days On Market

  Last Listing Agent Ivanhoe Alvarez LOKATION

  3425 Ferndell Dr, Winter Park, FL 32792
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  /30

  Est $624,007 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  1086 Azalea Ln Unit 1, Winter Park, FL 32789

  1086 Azalea Ln Unit 1, Winter Park, FL 32789
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  /65

  $2,295,000

  • 5 Beds
  • 3.5 Baths
  • 3,691 Sq Ft

  1885 Temple Dr, Winter Park, FL 32789

  NEW 2026 Black Steel doors windows with low e-dual pane glass ($150k value!). Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most

  Jennifer Sloan COMPASS FLORIDA LLC

  1885 Temple Dr, Winter Park, FL 32789
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  /17

  $3,950 per month

  • 3 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • House for Rent

  1302 Michigan Ave, Winter Park, FL 32789

  Please visit our website at www.ORLrent.com you will find photos of our homes, tenant application, pet application, sample lease and more information. If applying for any of our homes all adult applicants over the age of 18 must submit a fully completed Application online. Application fee is $95.00 for each adult. An application reservation fee must be paid in the amount of one month's rent (in

  Mo Jabr RE/MAX 200 REALTY

  1302 Michigan Ave, Winter Park, FL 32789
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  /2

  $235,000 Sold Jan 29, 2026

  613 Orange Tree Ct Unit 507, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Below List Price
  • $187/SF
  • 10 Days On Market

  Last Listing Agent Deborah Morris KELLER WILLIAMS ADVANTAGE REALTY

  613 Orange Tree Ct Unit 507, Maitland, FL 32751
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  /2

  Est $341,584 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft

  3251 Crown Jewel Ct, Winter Park, FL 32792

  3251 Crown Jewel Ct, Winter Park, FL 32792
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  /35

  $259,000 Pending

  • 2 Beds
  • 1 Bath
  • 762 Sq Ft

  2009 Cornell Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Unlock potential in one of Central Florida’s most desirable pockets! This centrally located Winter Park home shines with major updates already completed including a 2018 roof, 2022 HVAC, and fresh interior paint. Just bring a little extra love to elevate the finishes and create instant equity. Perfect as a long-term rental, short-term investment, or a

  Juliet Saldarriaga ORLANDO HOME DEALER LLC

  2009 Cornell Ave, Winter Park, FL 32789
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  /15

  $2,870 per month

  • 4 Beds
  • 3 Baths
  • 1,856 Sq Ft
  • House for Rent

  2029 Taylor Ave, Winter Park, FL 32792

  We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be

  2029 Taylor Ave, Winter Park, FL 32792
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  /2

  $279,000 Sold Aug 11, 2025

  Unlisted Address

  • 2 Beds
  • 2.5 Baths
  • 1,186 Sq Ft
  • Built 1981

  Last Sold Summary

  • $235/SF
  • 4 Days On Market

  Current Estimated Value $278,473

  Last Listing Agent Adriana Gonzalez PERFECT INVESTMENT REALTY

  Unlisted Address
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  /2

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,382 Sq Ft

  2609 Holly Rd Unit 2611, Winter Park, FL 32792

  2609 Holly Rd Unit 2611, Winter Park, FL 32792
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  /26

  $379,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft

  1007 Early Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to your next chapter at 1007 Early Ave in Winter Park, a charming 3-bedroom, 2-bathroom home. Thoughtfully maintained, this home combines character with modern comfort. Step inside to find inviting living spaces and enjoy peace of mind with a roof replaced in 2019. The spacious backyard is perfect for entertaining, gardening, or simply relaxing

  Eric Gross EXP REALTY LLC

  1007 Early Ave, Winter Park, FL 32789
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  /6

  $1,400 per month

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft
  • Apartment for Rent

  3212 Netherwood Dr, Winter Park, FL 32792

  This 400sqft QUICK MOVE in-law suite, with kitchen, bedroom and bathroom, along with living room space. Water and electricity are included with your rent. Laundry on-site. Suitable for 2-person occupancy.

  Sara Cruz FLORIDA HOMES REALTY & MORTGAGE

  3212 Netherwood Dr, Winter Park, FL 32792
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  /2

  $1,000,000 Sold Apr 04, 2025

  1001 Tuscany Place, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,458 Sq Ft
  • Built 1978

  Last Sold Summary

  • 22% Below List Price
  • $407/SF
  • 141 Days On Market

  Current Estimated Value $1,063,146

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1001 Tuscany Place, Winter Park, FL 32789
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  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft

  3015 Aaron Burr Ave Unit 7, Winter Park, FL 32792

  3015 Aaron Burr Ave Unit 7, Winter Park, FL 32792
• 

  

  /22

  $275,000

  • 2 Beds
  • 2 Baths
  • 893 Sq Ft

  609 Gallery Dr Unit 204, Winter Park, FL 32792

  PRICE REDUCED!!!!!!!!!IMMACULATE !!!!! Close to everything from this quiet 2nd floor 2/2 condo at THE GALLERY in Winter Park! Safe 3-minute walk to Publix, restaurants, movies and Crealde Art Center via gated back entrance to complex, Starbucks just outside the other way. Stainless steel and granite, dishwasher, built-in microwave. High ceilings in LR/DR and master. Walk-in closet in master.

  Olga Ray A2Z REALTY GROUP

  609 Gallery Dr Unit 204, Winter Park, FL 32792
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  /15

  $3,275 per month

  • 3 Beds
  • 1.5 Baths
  • 1,058 Sq Ft
  • House for Rent

  304 Granada Dr, Winter Park, FL 32789

  Property Id: 2306077Welcome to our renovated Winter Park home! This modern one-story property features 3 bedrooms plus a Loft. Enjoy the large backyard with an extra-large pool , furnished Gazebo and outdoor shower. Great Neighborhood with amazing schools. This home has an EV charger energy efficient appliances, security alarm and security cameras.To many feature’s and amenities to

  304 Granada Dr, Winter Park, FL 32789
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  /2

  $400,000 Sold May 07, 2025

  2292 Hawick Ln, Winter Park, FL 32792

  • 3 Beds
  • 1.5 Baths
  • 1,322 Sq Ft
  • Built 1958

  Last Sold Summary

  • $303/SF
  • 3 Days On Market

  Current Estimated Value $408,196

  Last Listing Agent Jason Alderman KELLER WILLIAMS ADVANTAGE REALTY

  2292 Hawick Ln, Winter Park, FL 32792
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  /2

  Est $1,141,618 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,377 Sq Ft

  1782 Mondrian Cir, Winter Park, FL 32789

  1782 Mondrian Cir, Winter Park, FL 32789
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  /32

  $675,000 Pending

  • 5 Beds
  • 2 Baths
  • 2,240 Sq Ft

  630 Saint Dunstan Way, Winter Park, FL 32792

  Under contract-accepting backup offers. Experience the best of Winter Park living at 630 Saint Dunstan Way, where modern comfort meets everyday functionality. Located just one block from the Cady Way Biking and Walking Trail, this beautifully renovated home showcases a stunning kitchen with a statement island, beverage center, and custom coffee station—perfect for both daily living and

  Melissa Johnson EXP REALTY LLC

  630 Saint Dunstan Way, Winter Park, FL 32792
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  /32

  $2,650 per month

  • 4 Beds
  • 2 Baths
  • 1,714 Sq Ft
  • House for Rent

  950 Hedgewood Ct, Winter Park, FL 32792

  Great opportunity to rent this 4-bedroom, 2-bath single-family home located on a quiet cul-de-sac. The home features a 2-car garage and a spacious backyard ideal for outdoor entertaining. Zoned for top-rated schools and conveniently located near major roadways, shopping, dining, and everyday amenities.

  Esther Griller FLORIDA REALTY INVESTMENTS

  950 Hedgewood Ct, Winter Park, FL 32792
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  /2

  $1,002,000 Sold May 31, 2025

  1265 Park Pointe Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,295 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Above List Price
  • $437/SF
  • 4 Days On Market

  Current Estimated Value $991,951

  Last Listing Agent Frances Speights KELLER WILLIAMS ADVANTAGE III

  1265 Park Pointe Ln, Winter Park, FL 32789
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  /2

  Est $466,838 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,964 Sq Ft

  1596 Little Wren Ln, Winter Park, FL 32792

  1596 Little Wren Ln, Winter Park, FL 32792
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  /26

  $370,000

  • 3 Beds
  • 2 Baths
  • 1,283 Sq Ft

  780 Baffie Ave, Winter Park, FL 32789

  Great opportunity to live in Winter Park in the Dubsdread Golf Community. This 3 bedroom, 2 bath home is situated on a deep lot (50 x 140) with 1283 sq. ft., Bamboo hardwood floors in several rooms, split bedroom floor plan, large kitchen with tile floors, and oak cabinets, and the dining room has a tongue and groove wood ceiling. The primary bedroom has Bamboo floors, tongue and groove wood

  Melissa Woodman FANNIE HILLMAN & ASSOCIATES

  780 Baffie Ave, Winter Park, FL 32789
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  /20

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  1500 Gay Rd Unit 3B, Winter Park, FL 32789

  Lakefront Living at Its Best: Renovated 1st Floor End Unit on Lake KillarneyExperience the charm and convenience of lakefront living in this recently renovated first-floor end unit, nestled in a picturesque community on Lake Killarney.Key Features:Stunning Sunset Views: Enjoy breathtaking sunsets from the lakefront deck, perfect for relaxing evenings.Water Activities: Benefit from

  1500 Gay Rd Unit 3B, Winter Park, FL 32789
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  /2

  $1,975,000 Sold Mar 27, 2025

  140 Dana Way, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 3,441 Sq Ft
  • Built 2011

  Last Sold Summary

  • 6% Below List Price
  • $574/SF
  • 16 Days On Market

  Current Estimated Value $1,987,396

  Last Listing Agent Maria Blanchard OLDE TOWN BROKERS INC

  140 Dana Way, Winter Park, FL 32789
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  /2

  Est $508,630 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,312 Sq Ft

  1303 Merrydale Way, Winter Park, FL 32792

  1303 Merrydale Way, Winter Park, FL 32792
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  /33

  $150,000

  • 1 Bed
  • 1 Bath
  • 749 Sq Ft

  2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792

  Welcome to this bright and cozy 1-bedroom, 1-bathroom corner unit located in the highly desirable Winter Park area of Orlando. This well-maintained condo features ceramic tile flooring throughout, a spacious walk-in closet in the master bedroom, a laundry closet with washer and dryer included, and modern light fixtures. Enjoy the outdoors on your very nice private balcony, and take advantage of

  SANTIAGO SILVA THE PAMPAS REAL ESTATE GROUP, LLC.

  2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792
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  /20

  $2,800 per month

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft
  • Property for Rent

  1315 Westchester Ave, Winter Park, FL 32789

  Improved Price! Wow, expect to be impressed. This home has been lovingly updated and features handscraped wood floors and tile throughout...no carpeting! In addition, there is an expansive ceiling in the living room, updated kitchen with tumbled marble backsplash, sleek appliances, granite counters and lots of wood cabinetry for storage. This home has double pane windows, updated bathrooms with

  Kristin Haughwout-Osorio PARKSIDE PROPERTIES, LLC

  1315 Westchester Ave, Winter Park, FL 32789
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  /2

  $230,000 Sold Aug 29, 2025

  1500 Gay Rd Unit 7A, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1972

  Last Sold Summary

  • 6% Below List Price
  • $224/SF
  • 205 Days On Market

  Last Listing Agent Sean McCartney PRISTINE FLORIDA PROPERTIES LLC

  1500 Gay Rd Unit 7A, Winter Park, FL 32789
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  /2

  Est $1,205,333 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,843 Sq Ft

  1830 Pineview Cir, Winter Park, FL 32792

  1830 Pineview Cir, Winter Park, FL 32792

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