Winter Park, FL Homes

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  /41

  $170,000

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit D116, Winter Park, FL 32789

  Location, location, location!! And priced to sell!! This 3 bedroom 2 bathroom corner unit condo is conveniently located within a short drive distance to Rollins College, UCF, Valencia College, hospitals, shopping, dining, and entertainment! The unit is located on the first floor and has an open floor plan, spacious kitchen with plenty of cabinet space (all appliances are included) 3 well

  Madalay Fleming LA ROSA REALTY KISSIMMEE

  1695 Lee Rd Unit D116, Winter Park, FL 32789
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  /6

  $2,275 per month

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • House for Rent

  7457 Blue Jacket Place E, 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 $2539.90. That covers your base rent, $2275.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  7457 Blue Jacket Place E, Winter Park, FL 32792
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  /2

  $335,000 Sold Jun 26, 2025

  • 1,408 Sq Ft
  • $238/SF
  • 120 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  3131 Ash Park Loop, Winter Park, FL 32792

  Under contract Taking back up offers!! Welcome to your next home located at 3131 Ash Park Loop in the serene Hyde Park community. This inviting 2-bedroom, 2-bathroom house offers a clean, open split floor plan that’s perfect for both living and entertaining. Move-in ready, this home also presents a unique chance for creative renovations, making it a blank canvas for your personal

  Amanda Binns STRICKLAND REALTY GROUP INC

  3131 Ash Park Loop, Winter Park, FL 32792
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  /35

  Est $309,320 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
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  /68

  $670,777

  • 4 Beds
  • 3 Baths
  • 2,846 Sq Ft

  3115 Heartleaf Place, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to your dream home in Winter Park, FL! This stunning 4-bedroom, 3-bathroom residence is situated on a desirable corner lot, offering ample space and privacy. This home was recently updated with a brand new HVAC system installed (May 2025), and a roof that’s only 4 years old (2021), complete plumbing repipe done in (2020). This home boasts

  Selby Turnbull EXP REALTY LLC

  3115 Heartleaf Place, Winter Park, FL 32792
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  /18

  $4,340 per month

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft
  • House for Rent

  332 N Phelps Ave, Winter Park, FL 32789

  Discover the allure of this Winter Park retreat! Nestled in a prime location, this delightful 3 bedroom, 2 bathroom abode boasts a sunlit open floor plan that invites comfort and relaxation. Adorned with warm wood flooring and custom millwork, the home exudes charm at every turn. The heart of this residence is its inviting kitchen, complete with ample counter space, abundant storage, and a

  David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

  332 N Phelps Ave, Winter Park, FL 32789
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  /2

  $515,000 Sold Jun 25, 2025

  • 1,953 Sq Ft
  • $264/SF
  • 68 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1968

  2607 Verde Ln, Winter Park, FL 32792

  Welcome home! This COMPLETELY REMODELED 4 bedrooms, 2 baths, 1,953 sq ftcul-de-sac home is nestled in the highly desirable Casa Aloma community. As you walkthrough the front door, you are greeted by a bright open concept living /dining roomspace. The turn-key property includes the following updates: brand new roof (2025),new hot water tank (2025), luxury vinyl plank flooring

  David Wald FOUNDERS REALTY GROUP

  2607 Verde Ln, Winter Park, FL 32792
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  /80

  Est $1,215,734 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
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  /30

  $765,000

  • 4 Beds
  • 2 Baths
  • 2,076 Sq Ft

  620 Darcey Dr, Winter Park, FL 32792

  New roof scheduled for replacement at end of July 2025. Charming brick Winter Park home in the desirable Brookshire Heights neighborhood. This home features four bedrooms, two baths, over 2,076 square feet of natural sunlight flowing throughout, enclosed back porch and a fully fenced backyard. Beautiful curb appeal with a long extended driveway, great for large gatherings, parking your boat, RV

  Michael Domi PREMIER SOTHEBY'S INTL. REALTY

  620 Darcey Dr, Winter Park, FL 32792
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  /17

  $2,349 per month

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • House for Rent

  324 Lake Fair Ln, Winter Park, FL 32789

  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 $2493.90. That covers your base rent, $2349.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  324 Lake Fair Ln, Winter Park, FL 32789
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  /2

  $2,250,000 Sold Jun 25, 2025

  • 3,694 Sq Ft
  • $609/SF
  • 98 Days On Market

  • 4 Beds
  • 6 Baths
  • Built 1958

  301 Rippling Ln, Winter Park, FL 32789

  Nestled along the serene shores of Lake Killarney, one of Winter Park's best-kept secrets Lake Killarney is one of Winter Park's largest freshwater spring-fed lakes (240 acres) this stunning lakefront home offers breathtaking views and direct water access. Featuring a private boat lift, dock, and spacious outdoor entertaining areas, this property is perfect for boating enthusiasts and nature

  Cynthia Fernandez XCLUSIVE HOMES LLC

  301 Rippling Ln, Winter Park, FL 32789
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  /11

  Est $464,991 Not Listed For Sale

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

  2770 Bright Bird Ln, Winter Park, FL 32792

  2770 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /40

  $399,000

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft

  311 E Morse Blvd Unit 7-5, Winter Park, FL 32789

  Major Price Improvement & Motivated Seller! Here is your rare opportunity to own a studio apartment in Whispering Waters, a 55+ iconic Condominium located just steps from Park Avenue and fabulous historic downtown Winter Park! This architectural mid-century beauty was built in 1960 and has survived every major hurricane since then. Whispering Waters has passed the Milestone and Structural

  Jeff Dodds CHARLES RUTENBERG REALTY ORLANDO

  311 E Morse Blvd Unit 7-5, Winter Park, FL 32789
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  /29

  $2,850 per month

  • 3 Beds
  • 2.5 Baths
  • 1,152 Sq Ft
  • House for Rent

  957 Dupont Ave, Winter Park, FL 32789

  Nestled in the heart of Winter Park's most desirable zip code, this beautifully maintained 3-bedroom, 2.5-bath home is a rare find. Located at 957 Dupont Ave, Winter Park, FL 32789, this charming residence offers 1,289 sq. ft. of living space on a generous 7,875 sq. ft. lot, complete with a 1-car attached garage. This home is move-in ready and brimming with updates. Step inside to discover an

  Stephanie Barber HOME & HIVE REALTY

  957 Dupont Ave, Winter Park, FL 32789
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  /2

  $100,000 Sold Jun 25, 2025

  • 1,020 Sq Ft
  • $98/SF
  • 1 Day On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  197 Scottsdale Square, Winter Park, FL 32792

  Featuring a functional floor plan, this property is perfect for investors or buyers looking to customize their new home. Located in a convenient and central location, you’ll be close to shopping, dining, major highways, and the vibrant charm of Winter Park. Whether you’re looking for a project to create your dream space or an investment opportunity, this property is a blank canvas waiting for

  Edward Lee LA ROSA REALTY ORLANDO LLC

  197 Scottsdale Square, Winter Park, FL 32792
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  /46

  Est $997,429 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,085 Sq Ft

  1913 S Lakemont Ave, Winter Park, FL 32792

  1913 S Lakemont Ave, Winter Park, FL 32792
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  /51

  $840,000 Open Sat 2PM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft

  100 S Interlachen Ave Unit 204, Winter Park, FL 32789

  Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned between the timeless charm of Park Avenue and the serene beauty of Lake Osceola. This fully furnished second-floor residence has been meticulously redesigned and renovated to maximize both space and style, offering the comfort of a thoughtfully designed home, enhanced by luxurious,

  Lois Rawson COLDWELL BANKER RESIDENTIAL RE

  100 S Interlachen Ave Unit 204, Winter Park, FL 32789
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  /2

  $2,170 per month

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • House for Rent

  1061 Portsmouth Ln, Winter Park, FL 32792

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at This home is priced to rent

  1061 Portsmouth Ln, Winter Park, FL 32792
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  /2

  $550,000 Sold Jun 24, 2025

  • 1,856 Sq Ft
  • $296/SF
  • 68 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  2310 Cady Way, Winter Park, FL 32792

  Welcome home to the sought after neighborhood of Brookshire Heights with in the Greater Winter Park Pines Community, where tree-lined streets and the friendly touch of a neighborhood where the mailman still delivers to your door await you! This spacious and updated 3-bedroom, 2-bathroom home is an entertainer’s dream, offering a perfect blend of modern updates, cozy living spaces, and serene

  Amy Turner KELLER WILLIAMS WINTER PARK

  2310 Cady Way, Winter Park, FL 32792
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  /11

  Not Listed For Sale

  0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792

  0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792
• 

  

  /23

  $375,000

  • Land
  • 0.17 Acre
  • $2,205,882 per Acre

  770 W Webster Ave Unit REAR LOT, Winter Park, FL 32789

  Here it is! Almost impossible to find 75x100 vacant R-3 lot in top Winter Park location! Ready for development. Located at northwest corner of Winter Park Commons project! Must be purchased with adjacent property 770 W. Webster – SFH listed for $425,000 (MLS O6323574). Walk to WP Village, Park Ave, WP9 Golf, Hannibal Square – dining, shopping and entertainment! Don’t miss this unique

  Lisa Gould KELLER WILLIAMS WINTER PARK

  770 W Webster Ave Unit REAR LOT, Winter Park, FL 32789
• 

  

  /19

  $2,595 per month

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft
  • House for Rent

  3976 Waterview Loop, Winter Park, FL 32792

  3 bedrooms, 2 bathrooms and a two car garage offering 1,444 square feet. Open floor plan with neutral colors, high ceilings. This home has a nice and open kitchen with an over abundance of cabinets, plenty of counter space granite and stainless steel appliances. Open to the kitchen you’ll find a large eat in nook and a family room/ dining room combination floor plan with sliding glass doors

  Courtney Davis ABSOLUTE REALTY GROUP, LLC

  3976 Waterview Loop, Winter Park, FL 32792
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  /2

  $850,000 Sold Jun 24, 2025

  • 2,910 Sq Ft
  • $292/SF
  • 25 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1954

  1832 Magnolia Ave, Winter Park, FL 32789

  Stunning fully remodeled Winter Park bungalow featuring a 500 square foot detached guest house. This charming residence is perfectly positioned on a rare oversized .41-acre double lot and has been completely transformed, offering a harmonious blend of modern luxury and timeless elegance. The main house features 4 bedrooms and 2.5 baths while the guest house features a living room, bedroom,

  Christopher Christensen COMPASS FLORIDA LLC

  1832 Magnolia Ave, Winter Park, FL 32789
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  /11

  Est $480,467 Not Listed For Sale

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

  2737 Bright Bird Ln, Winter Park, FL 32792

  2737 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /34

  $425,000

  • 4 Beds
  • 2 Baths
  • 1,008 Sq Ft

  770 W Webster Ave, Winter Park, FL 32789

  Stop the car! Check out this classic 4/2 Florida ranch ready for renovation! Newer roof, water heater. HW and tile floors, screened porch, utility/storage room. 1 car carport. OR develop your dream project on this hard to find 75x100 R-3 lot! Adjacent 75x100 R-3 vacant lot on the south side must be purchased simultaneously, listed for $375,000 (MLS O63223647) - for a total of 75x200 or

  Lisa Gould KELLER WILLIAMS WINTER PARK

  770 W Webster Ave, Winter Park, FL 32789
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  /10

  $2,190 per month

  • 3 Beds
  • 2 Baths
  • 1,701 Sq Ft
  • House for Rent

  1305 Viburnum Ln, 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 $2334.90. That covers your base rent, $2190.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1305 Viburnum Ln, Winter Park, FL 32792
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  /2

  $400,000 Sold Jun 24, 2025

  • 2,124 Sq Ft
  • $188/SF
  • 47 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1972

  4991 Tangerine Ave, Winter Park, FL 32792

  Welcome to 4991 Tangerine Ave in the heart of Winter Park! This charming 4-bedroom, 2-bathroom home offers comfortable living with no carpet throughout—perfect for easy maintenance. The spacious family and dining room combination provides an open and inviting layout, ideal for gatherings. A large, air-conditioned Florida room adds even more flexibility, ensuring plenty of space for entertaining.

  Darein Washington KELLER WILLIAMS ADVANTAGE REALTY

  4991 Tangerine Ave, Winter Park, FL 32792
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  /21

  Est $449,597 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2861 Clever Ln, Winter Park, FL 32792

  2861 Clever Ln, Winter Park, FL 32792
• 

  

  /68

  $658,900

  • 4 Beds
  • 3 Baths
  • 2,860 Sq Ft

  3110 Heartleaf Place, Winter Park, FL 32792

  Beautiful pool home with an open great room plan with high vaulted ceilings and master on the first floor situated on one of the largest lots in the subdivision with over an acre of land that extends all the way to Howell Creek. You’ll love the open and airy feel from the high ceilings and master suite features a large walk in closet and garden tub. The kitchen and formal dining room open to the

  Hojin Chang RE/MAX PRIME PROPERTIES

  3110 Heartleaf Place, Winter Park, FL 32792
• 

  

  /17

  $2,250 per month

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • House for Rent

  641 S Lakemont Ave, Winter Park, FL 32792

  Property has been updated and is move in ready for you! This delightful Winter Park home could be the perfect fit for you! Conveniently located near excellent public schools, shopping centers, and essential healthcare facilities, this remodeled 1450 square foot residence features 3 bedrooms and 2 full baths. The kitchen is brand new, boasting updated appliances, while the bathrooms have been

  Alisa Hildebrand WEICHERT REALTORS HALLMARK PROPERTIES

  641 S Lakemont Ave, Winter Park, FL 32792
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  /2

  $72,000 Sold Jun 24, 2025

  • 785 Sq Ft
  • $92/SF
  • 4 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1974

  273 Scottsdale Square Unit 273, Winter Park, FL 32792

  Located on the First Floor, this single-story condo features a one bedroom and one bathroom layout with a Foyer, Formal Dining and Living room with laminate flooring, Quaint Kitchen, Updated Bathroom and a Spacious Primary Bedroom with laminate flooring. In addition this condo includes a covered front porch and covered outdoor patio space with views of greenery. The unit has a private Laundry

  Erin Tompkins COLDWELL BANKER RESIDENTIAL RE

  273 Scottsdale Square Unit 273, Winter Park, FL 32792
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  /23

  Est $335,916 Not Listed For Sale

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

  3197 Crown Jewel Ct, Winter Park, FL 32792

  3197 Crown Jewel Ct, Winter Park, FL 32792
• 

  

  /39

  $529,900

  • 4 Beds
  • 2 Baths
  • 1,508 Sq Ft

  2844 Scarlet Rd, Winter Park, FL 32792

  Welcome to this stunning mid-century modern beauty where timeless design meets thoughtful, contemporary updates. Nestled in the highly sought-after neighborhood of Winter Park Pines, this 4-bedroom, 2-bathroom home offers over 1,500 sq ft of stylish, functional living space—and yes, your mail is still delivered to the front door! Step through a tastefully renovated entryway into an open, airy

  Amy Turner KELLER WILLIAMS WINTER PARK

  2844 Scarlet Rd, Winter Park, FL 32792
• 

  

  /20

  $2,275 per month

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • House for Rent

  2001 Nottingdale Ln, 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 $2419.90. That covers your base rent, $2275.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  2001 Nottingdale Ln, Winter Park, FL 32792
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  /2

  $468,470 Sold Jun 20, 2025

  • 1,724 Sq Ft
  • $272/SF
  • 25 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1977

  1026 Manchester Cir, Winter Park, FL 32792

  Welcome to your private oasis—where thoughtfully designed living spaces and beautiful upgrades come together in one incredible home. Whether it’s poolside afternoons, entertaining under the lanai, or cozy nights inside, this property delivers the Florida lifestyle you’ve been searching for. Step inside this well-maintained split floor plan home and enjoy a spacious family room that flows

  David Miller KELLER WILLIAMS HERITAGE REALTY

  1026 Manchester Cir, Winter Park, FL 32792
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  /32

  Est $619,968 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,770 Sq Ft

  1178 Wildmeadow Run, Winter Park, FL 32792

  1178 Wildmeadow Run, Winter Park, FL 32792
• 

  

  /19

  $187,500

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792

  Well maintained 2 bedroom/2 bathroom condo located in Lancelot of Winter Park. This spacious second floor unit with large windows brings in plenty of natural light. The main living areas have wood laminate tile flooring and granite countertops in the kitchen. The bathrooms have been updated with sleek fixtures, modern design elements and newly painted. Nearby, you will find top rated schools and

  Monica Perlas COLDWELL BANKER REALTY

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792
• 

  

  /21

  $1,695 per month

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Condo for Rent

  7449 Wynnewood Square Unit 182, Winter Park, FL 32792

  Come home to this charming townhome in Winter Park! This beautifully maintained 2 bedroom, 2.5 bath home offers the perfect blend of comfort, convenience, and privacy. Step inside to an inviting open floor plan ideal for entertaining or simply relaxing at home. The spacious kitchen features a cozy eating area, perfect for casual meals or morning coffee. Upstairs you will find two generously sized

  Annette Ortega KELLER WILLIAMS ADVANTAGE 2 REALTY

  7449 Wynnewood Square Unit 182, Winter Park, FL 32792
• 

  /2

  $82,000 Sold Jun 20, 2025

  • 1,020 Sq Ft
  • $80/SF
  • 13 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  185 Scottsdale Square Unit F185, Winter Park, FL 32792

  Beautifully maintained and updated 2 Bedroom and 2 Bath condo in Winter Park! Easy to care for tile floors flow through the kitchen, living, and dining areas. The kitchen features a tile backsplash, newer stainless steel appliances, and cabinets with decorative glass inserts. An open concept living and dining area is bright with a large slider that opens to a private patio. Each bedroom features

  Erin Baker FANNIE HILLMAN & ASSOCIATES

  185 Scottsdale Square Unit F185, Winter Park, FL 32792
• 

  

  /18

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 1,813 Sq Ft

  1411 Miller Ave, Winter Park, FL 32789

  1411 Miller Ave, Winter Park, FL 32789

Showing Results 401 - 440, Page 11 of 18