Winter Park, FL Homes

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  /41

  $245,000 Pending

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 229, Winter Park, FL 32789

  Under contract-accepting backup offers. DRAMATIC PRICE ADJUSTMENT! Million Dollar Lakefront View of Lake Killarney from Private Balcony and multiple Rooms in the Unit and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (321) 252-5096

  2500 Lee Rd Unit 229, Winter Park, FL 32789
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  /35

  Starting at $1,399 Per Month

  • 1 - 3 Beds

  3207 Rosebud Ln, Winter Park, FL 32792

  These apartments for rent in Orlando are close to Full Sail University and the University of Central Florida. Offering pet-friendly apartments one, two, and three-bedroom floorplans, Summerlin at Winter Park envelops residents in convenience and fun. With one of the largest pools in this area, you can beat the heat and relax and then take a visit to our 24-hour fitness center, billiards table, or

  Summerlin at Winter Park Apartments

  (321) 415-0553

  

  3207 Rosebud Ln, Winter Park, FL 32792
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  $2,700,000 Sold Oct 30, 2025

  1020 Mayfield Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,663 Sq Ft
  • Built 1989

  Last Sold Summary

  • 15% Below List Price
  • $1,014/SF
  • 149 Days On Market

  Current Estimated Value $2,675,463

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  1020 Mayfield Ave, Winter Park, FL 32789
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  /2

  Est $403,902 Not Listed For Sale

  627 Carvell Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft
  • Built 1957

  627 Carvell Dr, Winter Park, FL 32792

  Last Sold Summary

  • 4% Below List Price
  • $312/SF
  • 152 Days On Market

  • Last Sold Price $420,000
  • May 06, 2025

  Last Listing Agent Ray Al-Malt EXP REALTY LLC
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  /65

  $1,100,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,431 Sq Ft

  1800 Magnolia Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. NEW PRICE! Experience refined living in this exquisitely renovated custom home, positioned on an oversized corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. Inside, soaring 10-foot

  

  Kathy Summers

  FLORIDA REALTY INVESTMENTS

  (321) 306-4359

  1800 Magnolia Ave, Winter Park, FL 32789
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  /39

  Starting at $910 Per Month

  • 1 - 3 Beds

  2353 Winter Woods Blvd, Winter Park, FL 32792

  Come home to San Jose Apartments and enjoy the advantages of spacious apartments and ample parking. We have a wide variety of living spaces to choose from, all with large closets and modern amenities. You'll love our beautiful swimming pool and clubhouse. Call today to make San Jose Apartments your new home.TDD:711 for hearing impaired assistance.

  San Jose Apartments

  (689) 207-3265

  

  2353 Winter Woods Blvd, Winter Park, FL 32792
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  /2

  $714,000 Sold Mar 12, 2026

  636 Dunblane Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,803 Sq Ft
  • Built 1962

  Last Sold Summary

  • 2% Below List Price
  • $396/SF
  • 7 Days On Market

  Current Estimated Value $712,022

  Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  636 Dunblane Dr, Winter Park, FL 32792
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  /2

  Est $1,789,509 Not Listed For Sale

  2813 Northwood Blvd, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,444 Sq Ft
  • Built 2021

  2813 Northwood Blvd, Winter Park, FL 32789

  Last Sold Summary

  • 1% Below List Price
  • $523/SF
  • 1 Day On Market

  • Last Sold Price $1,800,000
  • May 06, 2025

  Last Listing Agent Candace Cassidy PREMIER SOTHEBY'S INTL. REALTY
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  /23

  $139,990

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit E103, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Waterfall Cove, where urban convenience meets tranquil living. This charming 2-bedroom, 1-bathroom condo offers a cozy retreat with all the perks of modern living. Located in the heart of Orlando, this condo is perfect for those looking for a blend of city life and natural beauty. As you step into the

  

  Jason Price

  RE/MAX SELECT GROUP

  (321) 324-0916

  1695 Lee Rd Unit E103, Winter Park, FL 32789
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  /26

  Starting at $1,240 Per Month

  • 1 - 3 Beds

  7000 University Blvd, Winter Park, FL 32792

  Central Place at Winter Park, where contemporary living meets convenience in a vibrant locale in Winter Park, FL. Our one, two, and three-bedroom apartment community offers a prime location on University Blvd. near Full Sail University and just moments away from the charming downtown Winter Park area. Experience the essence of modern living in our thoughtfully designed residences, featuring

  Central Place At Winter Park

  (689) 220-7951

  

  7000 University Blvd, Winter Park, FL 32792
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  /2

  $638,250 Sold Sep 02, 2025

  1536 Golfside Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft
  • Built 1980

  Last Sold Summary

  • $338/SF
  • 3 Days On Market

  Current Estimated Value $636,322

  Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  1536 Golfside Dr, Winter Park, FL 32792
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  /2

  Est $330,633 Not Listed For Sale

  992 Carnation Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 1959

  992 Carnation Dr, Winter Park, FL 32792

  Last Sold Summary

  • $330/SF
  • 57 Days On Market

  • Last Sold Price $330,000
  • May 09, 2025

  Last Listing Agent Bianca Botelho RE/MAX
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  /29

  $229,000

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft

  7454 Wynnewood Square Unit 188, Winter Park, FL 32792

  Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for you. This well maintained unit is move in ready: two-story 3 Bedrooms 2.5 Bath townhome style condo with two designated parking spaces. Upon entering you are greeted with a large living and dining room space. Tiled floors, tons of light, neutral colors, wet bar area are a few of the amazing qualities of this

  

  Manoj Patel

  APPLE REALTY

  (321) 497-0912

  7454 Wynnewood Square Unit 188, Winter Park, FL 32792
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  /50

  Starting at $1,585 Per Month

  • Studio - 2 Beds

  741 Clay St, Winter Park, FL 32789

  Welcome to Seven41 (Formerly known as Winter Park 2) featuring Winter Park, FL vibe with a gorgeous modern style. Brand new studio, one, and two bedroom apartments amplified by unrivaled finishes and amenities. Select Seven41 for its luxury.

  Seven41 Winter Park

  (689) 219-8058

  

  741 Clay St, Winter Park, FL 32789
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  /2

  $401,000 Sold Oct 15, 2025

  1809 Palmer Ave, Winter Park, FL 32792

  • Land
  • 9,147 Sq Ft
  • $1,909,524 per Acre

  Last Sold Summary

  • 5 Days On Market

  Current Estimated Value $388,953

  Last Listing Agent Christina Munkberg COLDWELL BANKER REALTY

  1809 Palmer Ave, Winter Park, FL 32792
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  /2

  Est $737,108 Not Listed For Sale

  2178 Whitehall Dr, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,360 Sq Ft
  • Built 1964

  2178 Whitehall Dr, Winter Park, FL 32792

  Last Sold Summary

  • $313/SF
  • 8 Days On Market

  • Last Sold Price $738,000
  • May 09, 2025

  Last Listing Agent Erica Diltz BALDWIN PARK REALTY LLC
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  /77

  $424,900

  • 4 Beds
  • 2.5 Baths
  • 1,616 Sq Ft

  1871 Casselwood St, Winter Park, FL 32792

  Beautifully updated, move-in ready home in Winter Park. A brand new A/C system is scheduled to be installed. This 4-bedroom, 2.5-bath home with a 2-car garage features waterproof luxury vinyl flooring, fresh interior finishes, new recessed lighting, and updated ceiling fans, all combined with a bright and functional layout. As you enter, you are welcomed by a custom wood decorative accent wall

  

  Alexa Monasterio Flores

  KELLER WILLIAMS ADVANTAGE 2 REALTY

  (321) 252-6747

  1871 Casselwood St, Winter Park, FL 32792
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  /36

  Starting at $1,322 Per Month

  • Studio - 3 Beds

  2000 Village Ln, Winter Park, FL 32792

  5 miles north of Orlando lies The Taylor at Winter Park. Experience true comfort and serenity in a newly renovated 1-, 2-, or 3-bedroom apartment. With spacious home layouts, sleek interior finishes, screened porches, private balconies, and stunning garden-style landscaping, you can enjoy a healthy, Zen lifestyle. Cut your commute and enjoy going out on the town with a prime location near

  The Taylor at Winter Park

  (562) 568-9229

  

  2000 Village Ln, Winter Park, FL 32792
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  /2

  $775,000 Sold May 21, 2025

  1818 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $342/SF
  • 189 Days On Market

  Current Estimated Value $813,430

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  1818 Mondrian Cir, Winter Park, FL 32789
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  /2

  Est $613,574 Not Listed For Sale

  2906 Rapidan Trail, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,326 Sq Ft
  • Built 1965

  2906 Rapidan Trail, Winter Park, FL 32789

  Last Sold Summary

  • 12% Above List Price
  • $236/SF
  • 4 Days On Market

  • Last Sold Price $550,000
  • May 08, 2025

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK
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  /22

  $262,000

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

  1500 Gay Rd Unit 20D, Winter Park, FL 32789

  LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA.CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE.BRIGHT SUN-FILLED

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (689) 399-5336

  1500 Gay Rd Unit 20D, Winter Park, FL 32789
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  /50

  Starting at $1,499 Per Month

  • 1 - 2 Beds

  3924 Calibre Bend Ln, Winter Park, FL 32792

  Calibre Bend Apartments offers a wide variety of apartment styles designed to accommodate the demands of today's sophisticated professional, while offering the setting and charm of yesteryear. You can expect unsurpassed amenities that will delight your senses, and a cozy community that makes coming home a breeze. Imagine your meals coming together perfectly in your gourmet kitchen, relaxing on

  Calibre Bend Apartments

  (689) 220-7836

  

  3924 Calibre Bend Ln, Winter Park, FL 32792
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  /2

  $567,000 Sold Apr 02, 2026

  1459 Nottingham Dr, Winter Park, FL 32792

  • 5 Beds
  • 2.5 Baths
  • 1,885 Sq Ft
  • Built 1971

  Last Sold Summary

  • $301/SF
  • 2 Days On Market

  Current Estimated Value $493,222

  Last Listing Agent Shirley Jones COLDWELL BANKER REALTY

  1459 Nottingham Dr, Winter Park, FL 32792
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  /2

  Est $424,895 Not Listed For Sale

  3259 Ellwood Ct, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,889 Sq Ft
  • Built 1969

  3259 Ellwood Ct, Winter Park, FL 32792

  Last Sold Summary

  • 2% Above List Price
  • $220/SF
  • 11 Days On Market

  • Last Sold Price $415,000
  • May 09, 2025

  Last Listing Agent Kelli Orszulak LPT REALTY LLC
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  /21

  $261,500

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

  1500 Gay Rd Unit 24B, Winter Park, FL 32789

  ANOTHER PRICE REDUCTION! OWNER WILL CONSIDER ALL REASONABLE OFFERS!Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas!Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters,

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (321) 450-8960

  1500 Gay Rd Unit 24B, Winter Park, FL 32789
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  Starting at $1,550 Per Month

  • Studio - 3 Beds

  1874 Harmon Ave, Winter Park, FL 32789

  Cultivated Living; Rooted in Style! Well-appointed Studio, One, Two, & Three Bedroom Apartment Homes in Winter Park, FL.Berkshire Winter Park is an ultra-luxury apartment community with thoughtfully curated features and enviable amenities. Select from a variety of studio, one, two, and three-bedroom floor plan schemes designed with excellence in mind. Escape ordinary; indulge in an apartment

  Berkshire Winter Park

  (689) 220-6346

  

  1874 Harmon Ave, Winter Park, FL 32789
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  $690,000 Sold Aug 14, 2025

  2433 Whitehall Cir, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,841 Sq Ft
  • Built 1962

  Last Sold Summary

  • 5% Above List Price
  • $375/SF
  • 2 Days On Market

  Current Estimated Value $634,000

  Last Listing Agent Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  2433 Whitehall Cir, Winter Park, FL 32792
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  /2

  Est $2,537,253 Not Listed For Sale

  254 Sylvan Blvd, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 3,653 Sq Ft
  • Built 2000

  254 Sylvan Blvd, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $710/SF
  • 8 Days On Market

  • Last Sold Price $2,594,550
  • May 09, 2025

  Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK
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  /41

  $510,000

  • 2 Beds
  • 1 Bath
  • 1,073 Sq Ft

  1036 Aragon Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Welcome to 1036 Aragon Avenue, a charming Winter Park bungalow perfectly positioned in one of Central Florida’s most sought-after locations. Nestled along picturesque cobblestone roads and surrounded by mature, tree-lined streets, this move-in ready home captures the character and warmth that make Winter Park real estate so desirable. Located just

  

  Tim Veigle

  WATSON REALTY CORP

  (321) 516-0689

  1036 Aragon Ave, Winter Park, FL 32789
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  /44

  Starting at $1,239 Per Month

  • Studio - 3 Beds

  4755 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to LIV at Winter Park, offering beautiful lakeside apartments for rent. Our Winter Park, Florida community offers your choice of studio, one-bedroom, two-bedroom, and three-bedroom apartment floor plans, with six distinct styles available. Experience the convenience of living just outside of the opportunities and excitement of Orlando, FL. Our spacious floor plans boast modern

  Liv at Winter Park Apartment Homes

  (689) 219-5609

  

  4755 N Goldenrod Rd, Winter Park, FL 32792
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  $730,000 Sold Mar 23, 2026

  1213 Lindenwood Ln, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,505 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $291/SF
  • 81 Days On Market

  Current Estimated Value $726,130

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  1213 Lindenwood Ln, Winter Park, FL 32792
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  /2

  Est $448,842 Not Listed For Sale

  2472 Firstlight Way, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft
  • Built 2020

  2472 Firstlight Way, Winter Park, FL 32792

  Last Sold Summary

  • 4% Above List Price
  • $208/SF
  • 53 Days On Market

  • Last Sold Price $432,000
  • May 08, 2025

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK
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  $270,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft

  1952 Spring St, Winter Park, FL 32792

  Under contract-accepting backup offers. Discover the opportunity to own in Winter Park at 1952 Spring Street—a well loved 3-bedroom, 2-bath townhouse offering charm, functionality, and a private yard, a rare find in this desirable area. Nestled in a well-established neighborhood, this home provides a peaceful residential feel and tranquility while remaining just minutes from everything Winter

  

  Bethanne Baer

  BEAR TEAM REAL ESTATE

  (321) 517-0753

  1952 Spring St, Winter Park, FL 32792
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  /50

  Starting at $1,832 Per Month

  • 1 - 3 Beds

  940 W Canton Ave, Winter Park, FL 32789

  Ready for an apartment home that truly feels like home? With upscale finishes and modern amenities, Paseo's units are ready to welcome you. You (and your pet!) can relax in our palm-lined courtyard, lounge by the pool, or play in our on-site dog park. With the shopping of Winter Park Village, movies at the Regal Cinema, and the historic downtown all close by, there are endless opportunities to

  Paseo at Winter Park Village

  (689) 219-4397

  

  940 W Canton Ave, Winter Park, FL 32789
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  $1,590,000 Sold Mar 06, 2026

  1166 Oaks Blvd, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,860 Sq Ft
  • Built 2018

  Last Sold Summary

  • 12% Below List Price
  • $556/SF
  • 153 Days On Market

  Current Estimated Value $1,592,749

  Last Listing Agent Kevin Kelly FANNIE HILLMAN & ASSOCIATES

  1166 Oaks Blvd, Winter Park, FL 32789
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  Not Listed For Sale

  3054 George Mason Ave Unit 6, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft
  • Built 1974

  3054 George Mason Ave Unit 6, Winter Park, FL 32792

  Last Sold Summary

  • $78/SF
  • 108 Days On Market

  • Last Sold Price $81,500
  • May 06, 2025

  Last Listing Agent Ali Khaku, MBA DALTON WADE INC
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  $424,900 Pending

  • 3 Beds
  • 2 Baths
  • 2,083 Sq Ft

  1367 Tierra Cir, Winter Park, FL 32792

  Under contract-accepting backup offers. Located in the highly desirable Casa Aloma neighborhood of Winter Park, this updated 3-bedroom, 2-bath, 2,083 sq ft home offers unique architectural appeal paired with thoughtful modern enhancements. Built in 1969, the home features concrete block construction on a concrete foundation, providing durability and peace of mind. Situated on a corner lot with

  

  Ben Jones

  SOUTHERN LAND & HOMES

  (321) 499-2258

  1367 Tierra Cir, Winter Park, FL 32792
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  /50

  Starting at $1,072 Per Month

  • 1 - 3 Beds

  349 Scottsdale Square, Winter Park, FL 32792

  This community boasts a prime location that effortlessly combines charm with convenience. Nestled in a well established neighborhood, it offers residents easy access to an array of amenities, including local shops, cafes, and restaurants, all just a short stroll away. The mature landscaping creates a tranquil atmosphere, inviting residents to take leisurely walks and enjoy the scenery.

  Winter Park Woods Apartments

  (689) 407-8026

  

  349 Scottsdale Square, Winter Park, FL 32792
• 

  /2

  $245,000 Sold Jun 26, 2025

  2471 Tahoe Cir, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $189/SF
  • 84 Days On Market

  Current Estimated Value $242,065

  Last Listing Agent Kevin Wilhelm MLSB THE BUREAU POWERED BY CAROM REALTY

  2471 Tahoe Cir, Winter Park, FL 32792
• 

  /2

  Est $155,578 Not Listed For Sale

  3291 Oak Lake Place Unit 125, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Built 1984

  3291 Oak Lake Place Unit 125, Winter Park, FL 32792

  Last Sold Summary

  • 4% Above List Price
  • $145/SF
  • 251 Days On Market

  • Last Sold Price $150,000
  • May 07, 2025

  Last Listing Agent Greg Vazzana FANNIE HILLMAN & ASSOCIATES

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