Winter Park, FL Homes

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  $2,289,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,334 Sq Ft

  2722 Eastern Pkwy, Winter Park, FL 32789

  Under Construction. Masterfully designed new construction by LUIH Luxury Homes, where architectural elegance and refined livability meet an unbeatable lifestyle. Located in the Audubon Park School District just a short stroll from the iconic East End Market. From its captivating façade to its meticulously curated interiors, every element of this residence has been crafted for those who expect the

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  2722 Eastern Pkwy, Winter Park, FL 32789
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  $1,900 per month

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Townhouse for Rent

  652 Grenadine Ct, Winter Park, FL 32792

  Newly remodeled, large, well-kept 2 bed, 2 full bath located in Winter Park, within walking distance to Full Sail and minutes from UCF, Valencia, Winter Park Hospital and many other employers. This beautiful, single story townhome is in a quiet, family-friendly neighborhood. A large kitchen and dining area are great for entertaining. This unit fronts a greenspace affording you privacy and a

  652 Grenadine Ct, Winter Park, FL 32792
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  $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 $1,055,659

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1001 Tuscany Place, Winter Park, FL 32789
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft

  677 Grenadine Ct Unit S, Winter Park, FL 32792

  677 Grenadine Ct Unit S, Winter Park, FL 32792
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  $520,000

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  422 S Ranger Blvd, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. ?? Mid-Century Modern Gem in Sought-After Winter Park Pines Lovingly maintained and move-in ready, this Mid-Century Modern 4-bedroom, 2-bath home (just under 1,700 sq. ft.) offers light-filled living and timeless style in the heart of Winter Park Pines. Set beneath graceful mature oaks, the landscaped front yard provides a welcoming canopy. Step

  David Perez COLDWELL BANKER RESIDENTIAL RE

  422 S Ranger Blvd, Winter Park, FL 32792
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  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • House for Rent

  1055 Cherokee Ave, Winter Park, FL 32789

  Completely renovated home for RENT located next to Winter Park Village! No HOA! Come park your RV, boat, or vehicles on the two beautifully paved private driveways. This home features new porcelain tile floor throughout and wooden floors in the bedrooms. New interior paint, new kitchen cabinets, new light fixtures, newer roof from 2018 and AC is from 2022. New granite countertops with a waterfall

  Rafael Casallas, Pa EMPIRE NETWORK REALTY

  1055 Cherokee Ave, Winter Park, FL 32789
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  $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 $411,986

  Last Listing Agent Jason Alderman KELLER WILLIAMS ADVANTAGE REALTY

  2292 Hawick Ln, Winter Park, FL 32792
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  Est $264,958 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,470 Sq Ft

  7164 Swallow Run Unit GE, Winter Park, FL 32792

  7164 Swallow Run Unit GE, Winter Park, FL 32792
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  $1,190,000 Open Sat 2PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,557 Sq Ft

  1150 Kenwood Ave, Winter Park, FL 32789

  Nestled in the heart of Winter Park, this exquisite 3-bedroom, 2.5-bath residence offers 2,557 square feet of beautifully designed living space along with a spacious 2-car garage. Situated on a charming, tree-lined brick street just minutes from Park Avenue, the home’s first level includes a welcoming living room, versatile bonus/flex space, dining room with built-ins, a well-appointed kitchen,

  JJ Mackle PREMIER SOTHEBY'S INTL. REALTY

  1150 Kenwood Ave, Winter Park, FL 32789
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  /10

  $2,995 per month

  • 4 Beds
  • 3 Baths
  • 2,194 Sq Ft
  • House for Rent

  3061 Nicholson 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 $3139.90. That covers your base rent, $2995.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  3061 Nicholson Dr, Winter Park, FL 32792
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  $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 $992,554

  Last Listing Agent Frances Speights KELLER WILLIAMS ADVANTAGE III

  1265 Park Pointe Ln, Winter Park, FL 32789
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft

  681 Grenadine Ct Unit S, Winter Park, FL 32792

  681 Grenadine Ct Unit S, Winter Park, FL 32792
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  $214,900

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

  3254 Oak Lake Place Unit 137, Winter Park, FL 32792

  THIS GORGEOUS 2 BED/2.5BATHS MID-CENTURY MODERN ARCHITECTURALLY DESIGNED SINGLE FAMILY HOME IS NEWLY REMODELED AND NESTLED IN WINTER PARK COMMUNITY OF HIDDEN OAKS. THIS ELEGANT HOME FEATURES 1,031 SQ. FT. OF LIVING SPACE, A MODERN SWEDISH KITCHEN FEATURING QUARTZITE COUNTER TOPS WITH FUNCTIONAL DRAWERS, PORCELEN TILE FLOORS. STAINLESS STEELE APPLIANCES INCLUDE RANGE, RANGE HOOD, REFRIGERATOR AND

  Darryl Henderson, Jr GLOBAL ENTERPRISE REALTY GROUP

  3254 Oak Lake Place Unit 137, Winter Park, FL 32792
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  /12

  $1,575 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Townhouse for Rent

  1565 Michigan Ave, Winter Park, FL 32789

  Cute and comfortable 1/2 of a duplex in the heart of Winter Park. This 2 bedroom 1 bath unit features ceramic tile throughout, ceiling fans in the bedroom, private washer and dryer and a full sized kitchen. The unit shares a back yard and there is limited storage on site as well. The unit is located minutes from I 4, shopping, restaurants and Rollins College.

  Troy Hensley BHHS FLORIDA REALTY

  1565 Michigan Ave, Winter Park, FL 32789
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  $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 $1,948,883

  Last Listing Agent Maria Blanchard OLDE TOWN BROKERS INC

  140 Dana Way, Winter Park, FL 32789
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  Est $479,795 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft

  2260 Shadowland Loop, Winter Park, FL 32792

  2260 Shadowland Loop, Winter Park, FL 32792
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  $425,000 Open Sun 11AM - 2:30PM

  • 4 Beds
  • 2 Baths
  • 1,725 Sq Ft

  1816 Ivy Ln, Winter Park, FL 32792

  NEW REDUCED PRICE BELOW MARKET IN DESIRABLE TANGLEWOOD WINTER PARK COMMUNITY WITH NO HOA! ALLOWS SHORT TERM RENTALS (STR). LOW TAX DISTRICT. This is probably the closet you can get to Winter Park (Park Ave) without having to pay the Winter Park taxes or conform to their restrictions! This property has been extremely well maintained and would be an amazing home for a new family. ROOF IS 2023! All

  Michael Cameron CAMERON REALTY GROUP LLC

  1816 Ivy Ln, Winter Park, FL 32792
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  $3,230 per month

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

  2029 Taylor Ave, Winter Park, FL 32792

  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 happy to help you find a different home or refund your Hold Fee. This home

  2029 Taylor Ave, Winter Park, FL 32792
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  $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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  Not Listed For Sale

  0 Grand Rd Unit MFRO6213919, Winter Park, FL 32792

  0 Grand Rd Unit MFRO6213919, Winter Park, FL 32792
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  $335,000

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  Unlisted Address

  Charming 3-bedroom, 2-bathroom single-family home nestled on a generous 9,626 sq ft lot in Winter Park’s desirable Goldenrod area. Built in 1972, this cozy one-story home offers 1,104 sq ft of living space with a classic split-bedroom floor plan — perfect for privacy while entertaining. The residence features tile and carpet flooring, central air conditioning, and a functional kitchen complete

  Rosa Rivera SKINNER REALTY, INC.

  Unlisted Address
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  /58

  $4,850 per month

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft
  • Condo for Rent

  104 S Interlachen Ave Unit 114, Winter Park, FL 32789

  Welcome to the Cloisters, an exclusive lakefront condominium community in Winter Park, now available for lease. This first-floor two-bedroom, two-bath residence offers a thoughtfully updated open-concept layout and direct garden access. Entering from the main hallway, you enter into a welcoming interior where the kitchen sits to the right, featuring a breakfast bar that connects seamlessly to the

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  104 S Interlachen Ave Unit 114, Winter Park, FL 32789
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  $3,450,000 Sold Jul 25, 2025

  182 N Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 5 Baths
  • 4,812 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $717/SF
  • 61 Days On Market

  Current Estimated Value $3,405,789

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  182 N Phelps Ave, Winter Park, FL 32789
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  Est $716,109 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,416 Sq Ft

  1360 Blue Stem Ln, Winter Park, FL 32792

  1360 Blue Stem Ln, Winter Park, FL 32792
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  $580,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft

  1740 Anzle Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. PROPERTY AS-IS - Perfect for a fix-and-flip or new construction. Nestled in the heart of Winter Park’s coveted 32789 ZIP code, this stunning new possibility offers the epitome of luxury living in one of Central Florida’s most coveted neighborhoods. The current structure is being approved for demolition, and the 30-day public notice has been completed. This

  Freddy DeCoster GOYAL & DECOSTER REALTY

  1740 Anzle Ave, Winter Park, FL 32789
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  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • House for Rent

  803 Ellendale Dr, Winter Park, FL 32792

  This property is available. Please inquire on this site to schedule a showing. Welcome to this charming home located at 803 Ellendale Drive in the heart of Winter Park, FL. Nestled under the shade of mature trees, this delightful property offers a perfect blend of comfort and convenience. The exterior boasts a welcoming front yard with lush greenery and a spacious driveway. Inside, you'll

  803 Ellendale Dr, Winter Park, FL 32792
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  $1,950,000 Sold Sep 16, 2025

  141 Oakwood Way, Winter Park, FL 32789

  • 5 Beds
  • 4 Baths
  • 3,909 Sq Ft
  • Built 2015

  Last Sold Summary

  • 14% Below List Price
  • $499/SF
  • 170 Days On Market

  Current Estimated Value $1,955,862

  Last Listing Agent Nicole Rader MAINFRAME REAL ESTATE

  141 Oakwood Way, Winter Park, FL 32789
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  Est $153,349 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft

  160 Lewfield Cir Unit 160, Winter Park, FL 32792

  160 Lewfield Cir Unit 160, Winter Park, FL 32792
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  $1,369,950

  • 4 Beds
  • 4 Baths
  • 3,474 Sq Ft

  952 Moss Ln, Winter Park, FL 32789

  Back on market at no fault of the seller! Brand new Roof and HVAC systems 2025. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and modern comfort. This captivating 4-bedroom, 3-bathroom home exudes warmth and sophistication, creating an inviting haven for discerning buyers. Sunlight floods every room, highlighting the home’s

  Terry Connors THE SHOP REAL ESTATE CO.

  952 Moss Ln, Winter Park, FL 32789
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  $3,295 per month

  • 3 Beds
  • 2 Baths
  • 1,747 Sq Ft
  • House for Rent

  1807 N Park Ave, Winter Park, FL 32789

  Welcome to 1807 N Park Ave, a beautifully maintained 3-bedroom, 3-bathroom home offering 1,747 sq. ft. of bright, open living space in the heart of desirable Winter Park. This charming home features a spacious layout with a warm and inviting living area, a functional kitchen with plenty of storage, and comfortable bedrooms — each with its own bath, offering added privacy and convenience. Step

  Jason Hamilton THE REALTY MEDICS

  1807 N Park Ave, Winter Park, FL 32789
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  $170,000 Sold Jun 09, 2025

  3208 Oak Lawn Place Unit 218, Winter Park, FL 32792

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

  Last Sold Summary

  • 8% Below List Price
  • $165/SF
  • 53 Days On Market

  Current Estimated Value $173,029

  Last Listing Agent Ali Khaku, MBA DALTON WADE INC

  3208 Oak Lawn Place Unit 218, Winter Park, FL 32792
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  Est $441,047 Not Listed For Sale

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

  2953 Clever Ln, Winter Park, FL 32792

  2953 Clever Ln, Winter Park, FL 32792
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  $1,770,000

  • 5 Beds
  • 4.5 Baths
  • 3,533 Sq Ft

  617 Worthington Dr, Winter Park, FL 32789

  WINTER PARK FIVE BEDROOM POOL HOME - Discover luxurious living in the heart of Winter Park! Crafted with exquisite attention to detail, this 5-bedroom, 4.5-bathroom pool residence showcases absolute perfection and modern elegance. Built in 2018 by David Weekley Homes, the property boasts a captivating stone façade and a private backyard oasis featuring a saltwater, heated pool and spa with water

  Kelly Price KELLY PRICE & COMPANY LLC

  617 Worthington Dr, Winter Park, FL 32789
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  /19

  $2,799 per month

  • 3 Beds
  • 2 Baths
  • 2,125 Sq Ft
  • House for Rent

  3621 Oak Vista 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 $2943.90. That covers your base rent, $2799.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  3621 Oak Vista Ln, Winter Park, FL 32792
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  $625,000 Sold May 09, 2025

  1401 Lone Feather Trail, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,770 Sq Ft
  • Built 2022

  Last Sold Summary

  • 4% Below List Price
  • $353/SF
  • 75 Days On Market

  Current Estimated Value $618,524

  Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

  1401 Lone Feather Trail, Winter Park, FL 32792
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  Est $189,900 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft

  3351 River View Way Unit 41, Winter Park, FL 32792

  3351 River View Way Unit 41, Winter Park, FL 32792
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  $6,600,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,636 Sq Ft

  2661 Vía Tuscany, Winter Park, FL 32789

  CALLING HIGHEST AND BEST BY 09/26/2025!! SELLER FINANCING AVAILABLE WITH VERY ATTRACTIVE TERMSIntroducing a Unique, Stunning Modern HomeA groundbreaking architectural masterpiece, this one-of-a-kind residence is built with reinforced concrete, steel, and iron framing, featuring floor-to-ceiling glass walls with no traditional windows. Designed to exceed Florida’s strictest

  Prescilla Vazquez PV LUXURY GROUP PA

  2661 Vía Tuscany, Winter Park, FL 32789
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  $1,299 per month

  • 2 Beds
  • 1 Bath
  • 805 Sq Ft
  • Townhouse for Rent

  1436 Minnesota Ave, Winter Park, FL 32789

  Updated 2 bedroom and 1 bath apartment located in the heart of the industrial district of Winter Park 32789. Close to Advent Health (Rollins campus), I-4 , Orange Avenue, 17-92, Rollins College, Fairbanks, Mills 50, College Park and Downtown Winter Park. Please no pets.

  Ruth Harris COLDWELL BANKER RESIDENTIAL RE

  1436 Minnesota Ave, Winter Park, FL 32789
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  $1,125,000 Sold Jan 08, 2025

  805 Hamilton Place Ct, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 2,810 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Above List Price
  • $400/SF
  • 4 Days On Market

  Current Estimated Value $1,157,824

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  805 Hamilton Place Ct, Winter Park, FL 32789
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  Est $471,851 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  2444 Firstlight Way, Winter Park, FL 32792

  2444 Firstlight Way, Winter Park, FL 32792

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