11,861

Homes in ZIP Code 32789

Section Image
  • 1802 Arbor Park Dr, Winter Park, FL 32789
    1802 Arbor Park Dr, Winter Park, FL 32789
    /2

    $895,000

    Sold Dec 29, 2025

    1802 Arbor Park Dr, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 1,808 Sq Ft
    • Built 1968

    Last Sold Summary

    • $495/SF
    • 1 Day On Market

    Current Estimated Value $973,177

    Last Listing Agent Jennifer Roberts FLORIDA EXECUTIVE REALTY

    1802 Arbor Park Dr, Winter Park, FL 32789
    • 420 Killarney Bay Ct Unit 2, Winter Park, FL 32789
      420 Killarney Bay Ct Unit 2, Winter Park, FL 32789
      420 Killarney Bay Ct Unit 2, Winter Park, FL 32789
      /18

      Est $332,285

      Not Listed For Sale

      420 Killarney Bay Ct Unit 2, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,160 Sq Ft
      • Built 1986
      420 Killarney Bay Ct Unit 2, Winter Park, FL 32789

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Corey Mahon CENTRO REAL ESTATE GROUP, LLC

  • 726 N Pennsylvania Ave, Winter Park, FL 32789
    726 N Pennsylvania Ave, Winter Park, FL 32789
    726 N Pennsylvania Ave, Winter Park, FL 32789
    /37

    $1,185,999

    • 6 Beds
    • 4 Baths
    • 2,282 Sq Ft

    726 N Pennsylvania Ave, Winter Park, FL 32789

    Opportunities like this don’t come around often, this is currently the only duplex available within walking distance of Park Avenue and just minutes from Rollins College, placing it directly in one of the most consistent, high-demand rental pockets in Winter Park. With two 3-bedroom, 2-bathroom units (6 bedrooms total), this property is ideally positioned for strong, stable income. Live in one

    Brandon Geers COMPASS FLORIDA LLC

    726 N Pennsylvania Ave, Winter Park, FL 32789
  • 2381 Roxbury Rd, Winter Park, FL 32789
    2381 Roxbury Rd, Winter Park, FL 32789
    /2

    $470,000

    Sold Dec 23, 2025

    2381 Roxbury Rd, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,785 Sq Ft
    • Built 1949

    Last Sold Summary

    • 8% Below List Price
    • $263/SF
    • 24 Days On Market

    Current Estimated Value $481,464

    Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

    2381 Roxbury Rd, Winter Park, FL 32789
    • 647 Huntington Ave Unit 8, Winter Park, FL 32789
      647 Huntington Ave Unit 8, Winter Park, FL 32789
      /2

      Est $344,452

      Not Listed For Sale

      647 Huntington Ave Unit 8, Winter Park, FL 32789

      • 2 Beds
      • 2.5 Baths
      • 1,204 Sq Ft
      • Built 1981
      647 Huntington Ave Unit 8, Winter Park, FL 32789

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  • 450 Lakewood Dr, Winter Park, FL 32789
    450 Lakewood Dr, Winter Park, FL 32789
    450 Lakewood Dr, Winter Park, FL 32789
    /88

    $2,500,000

    • 5 Beds
    • 6 Baths
    • 4,572 Sq Ft

    450 Lakewood Dr, Winter Park, FL 32789

    Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within walking distance of the world-class dining and boutiques of Park Avenue, views of Lake Osceola with easy lake access, with a coveted Winter Park location and top notch schools.This 5-bedroom, 4-full and 2-half-bath pool home

    Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

    450 Lakewood Dr, Winter Park, FL 32789
  • 67 Cypress Ln, Maitland, FL 32751
    67 Cypress Ln, Maitland, FL 32751
    /2

    $952,000

    Sold Jul 08, 2026

    67 Cypress Ln, Maitland, FL 32751

    • 4 Beds
    • 3 Baths
    • 2,292 Sq Ft
    • Built 1979

    Last Sold Summary

    • 29% Below List Price
    • $415/SF
    • 160 Days On Market

    Current Estimated Value $970,097

    Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

    67 Cypress Ln, Maitland, FL 32751
    • 1248 S Pennsylvania Ave Unit 7, Winter Park, FL 32789
      1248 S Pennsylvania Ave Unit 7, Winter Park, FL 32789
      /2

      Est $826,761

      Not Listed For Sale

      1248 S Pennsylvania Ave Unit 7, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 1,957 Sq Ft
      • Built 2007
      1248 S Pennsylvania Ave Unit 7, Winter Park, FL 32789

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Trevor Brown FANNIE HILLMAN & ASSOCIATES

  • 2560 Franklin Ave, Winter Park, FL 32789
    2560 Franklin Ave, Winter Park, FL 32789
    2560 Franklin Ave, Winter Park, FL 32789
    /22

    $479,000

    $100K PRICE DROP Pending
    • 4 Beds
    • 2 Baths
    • 1,514 Sq Ft

    2560 Franklin Ave, Winter Park, FL 32789

    Come see this charming 4 bed, 2 bath, 2 story home in Winter Park/ Lake Killarney location, 6 mins to downtown Winter park & Winter Park Village with an outdoor shopping center featuring many shops & restaurants. Convenience to Wholefood & Publix Supermarket. Quiet neighborhood with No HOA fees. Its stone elevation gives a captivating curb appeal. Situated on a generous 0.34 acres lot. The

    Jiraporn Wasserman LoKation

    2560 Franklin Ave, Winter Park, FL 32789
  • 1817 Jessica Ct, Winter Park, FL 32789
    1817 Jessica Ct, Winter Park, FL 32789
    /2

    $540,000

    Sold Dec 29, 2025

    1817 Jessica Ct, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,870 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Above List Price
    • $289/SF
    • 3 Days On Market

    Current Estimated Value $579,358

    Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

    1817 Jessica Ct, Winter Park, FL 32789
    • 1264 S Pennsylvania Ave Unit 10, Winter Park, FL 32789
      1264 S Pennsylvania Ave Unit 10, Winter Park, FL 32789
      1264 S Pennsylvania Ave Unit 10, Winter Park, FL 32789
      /90

      Est $830,811

      Not Listed For Sale

      1264 S Pennsylvania Ave Unit 10, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 1,957 Sq Ft
      • Built 2007
      1264 S Pennsylvania Ave Unit 10, Winter Park, FL 32789

      Last Sold Summary

      • 98 Days On Market

      Last Listing Agent David Gallup RE/MAX 200 REALTY

  • 1611 Chestnut Ave, Winter Park, FL 32789
    1611 Chestnut Ave, Winter Park, FL 32789
    1611 Chestnut Ave, Winter Park, FL 32789
    /51

    $995,000

    $105K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,916 Sq Ft

    1611 Chestnut Ave, Winter Park, FL 32789

    HUGE PRICE IMPROVEMENT!!Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood, unique charm and character, and the bones of new construction. Gutted to the studs and rebuilt with intention, every major system is new — every step of this rennovation

    Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

    1611 Chestnut Ave, Winter Park, FL 32789
  • 141 W Lake Sue Ave, Winter Park, FL 32789
    141 W Lake Sue Ave, Winter Park, FL 32789
    /2

    $1,450,000

    Sold Mar 19, 2026

    141 W Lake Sue Ave, Winter Park, FL 32789

    • Land
    • 22,215 Sq Ft
    • $2,843,137 per Acre

    Last Sold Summary

    • 14% Below List Price
    • 137 Days On Market

    Current Estimated Value $3,847,510

    Last Listing Agent Brian Mitnik RE/MAX 200 REALTY

    141 W Lake Sue Ave, Winter Park, FL 32789
    • 1302 S Pennsylvania Ave Unit 4, Winter Park, FL 32789
      1302 S Pennsylvania Ave Unit 4, Winter Park, FL 32789
      1302 S Pennsylvania Ave Unit 4, Winter Park, FL 32789
      /37

      Est $284,712

      Not Listed For Sale

      1302 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

      • 2 Beds
      • 1 Bath
      • 830 Sq Ft
      • Built 1983
      1302 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

  • 311 E Morse Blvd Unit 4-5, Winter Park, FL 32789
    311 E Morse Blvd Unit 4-5, Winter Park, FL 32789
    311 E Morse Blvd Unit 4-5, Winter Park, FL 32789
    /39

    $1,050,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,763 Sq Ft

    311 E Morse Blvd Unit 4-5, Winter Park, FL 32789

    Experience effortless Winter Park living in Whispering Waters, a premier 55+ lakefront community beautifully situated along the shores of Lake Osceola & just a short stroll from Park Avenue. Priced below appraised value, this rare third-floor mid-century modern condo offers exceptional value and a truly turnkey lifestyle. Filled with natural light, the thoughtfully designed floor plan features

    Kim Garcia KELLER WILLIAMS ADVANTAGE REALTY

    311 E Morse Blvd Unit 4-5, Winter Park, FL 32789
  • 100 S Interlachen Ave Unit 404, Winter Park, FL 32789
    100 S Interlachen Ave Unit 404, Winter Park, FL 32789
    /2

    $1,100,000

    Sold Apr 15, 2026

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

    • 2 Beds
    • 2 Baths
    • 1,220 Sq Ft
    • Built 1971

    Last Sold Summary

    • 8% Below List Price
    • $902/SF
    • 51 Days On Market

    Current Estimated Value $1,063,035

    Last Listing Agent Ruth Harris COLDWELL BANKER REALTY

    100 S Interlachen Ave Unit 404, Winter Park, FL 32789
    • 1086 Azalea Ln, Winter Park, FL 32789
      1086 Azalea Ln, Winter Park, FL 32789
      /2

      Est $608,337

      Not Listed For Sale

      1086 Azalea Ln, Winter Park, FL 32789

      • 3 Beds
      • 2 Baths
      • 1,785 Sq Ft
      • Built 1983
      1086 Azalea Ln, Winter Park, FL 32789

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  • 2126 Albert Lee Pkwy, Winter Park, FL 32789
    2126 Albert Lee Pkwy, Winter Park, FL 32789
    2126 Albert Lee Pkwy, Winter Park, FL 32789
    /39

    $415,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,187 Sq Ft

    2126 Albert Lee Pkwy, Winter Park, FL 32789

    Welcome home to this adorable and beautifully updated 3-bedroom, 2-bathroom home in the heart of Winter Park! From the moment you arrive, the cheerful teal front door adds the perfect pop of color and sets the tone for the charm you’ll find throughout. **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

    Ross Pino COMPASS FLORIDA LLC

    2126 Albert Lee Pkwy, Winter Park, FL 32789
  • 105 Conrad Ct, Winter Park, FL 32789
    105 Conrad Ct, Winter Park, FL 32789
    /2

    $429,999

    Sold Oct 21, 2025

    105 Conrad Ct, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,573 Sq Ft
    • Built 1958

    Last Sold Summary

    • $273/SF
    • 24 Days On Market

    Current Estimated Value $455,880

    Last Listing Agent Pam Grabenhorst THE WILKINS WAY LLC

    105 Conrad Ct, Winter Park, FL 32789
    • 213 E Canton Ave Unit 213, Winter Park, FL 32789
      213 E Canton Ave Unit 213, Winter Park, FL 32789
      /2

      Est $525,561

      Not Listed For Sale

      213 E Canton Ave Unit 213, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,040 Sq Ft
      • Built 1971
      213 E Canton Ave Unit 213, Winter Park, FL 32789

      Last Sold Summary

      • 97 Days On Market

      Last Listing Agent Becki Douglas MAINFRAME REAL ESTATE

  • 981 Aragon Ave, Winter Park, FL 32789
    981 Aragon Ave, Winter Park, FL 32789
    981 Aragon Ave, Winter Park, FL 32789
    /31

    $494,999

    $40K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 857 Sq Ft

    981 Aragon Ave, Winter Park, FL 32789

    Charming renovated bungalow on a brick street in the heart of Winter Park! Recently updated with new finishes and appliances throughout. Huge back yard with plenty of potential space for ADU! Move in ready, no HOA, and just a short stroll from Rollins College and beautiful Park Avenue. A rare must see opportunity!

    Thomas Bonner COLDWELL BANKER REALTY

    981 Aragon Ave, Winter Park, FL 32789
  • 1130 Park North Place, Winter Park, FL 32789
    1130 Park North Place, Winter Park, FL 32789
    /2

    $1,887,500

    Sold Aug 31, 2026

    1130 Park North Place, Winter Park, FL 32789

    • 5 Beds
    • 3.5 Baths
    • 4,011 Sq Ft
    • Built 1968

    Last Sold Summary

    • 29% Below List Price
    • $471/SF
    • 120 Days On Market

    Current Estimated Value $2,113,656

    Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

    1130 Park North Place, Winter Park, FL 32789
    • 1216 Park Green Place, Winter Park, FL 32789
      1216 Park Green Place, Winter Park, FL 32789
      /2

      Est $424,732

      Not Listed For Sale

      1216 Park Green Place, Winter Park, FL 32789

      • 3 Beds
      • 3 Baths
      • 2,020 Sq Ft
      • Built 1982
      1216 Park Green Place, Winter Park, FL 32789

      Last Sold Summary

      • 207 Days On Market

      Last Listing Agent Dustin Hope BUY THE SEA REALTY LLC

  • 2183 Crandon Ave, Winter Park, FL 32789
    2183 Crandon Ave, Winter Park, FL 32789
    2183 Crandon Ave, Winter Park, FL 32789
    /28

    $499,000

    • 4 Beds
    • 2 Baths
    • 1,200 Sq Ft

    2183 Crandon Ave, Winter Park, FL 32789

    Income Producing Duplex in Winter Park, Florida! Great investment opportunity in a desirable location! This duplex features two 2-bedroom, 1-bath units, each approximately 600 square feet, with private entrances, central AC, and a private screened patio area. Both units are currently leased, providing established rental income and long-term occupancy. Each unit offers a spacious living area and a

    Walkidia Reyes, PA REAL PROPERTY MANAGEMENT AND REALTY

    2183 Crandon Ave, Winter Park, FL 32789
  • 1122 Washington Ave Unit 7, Winter Park, FL 32789
    1122 Washington Ave Unit 7, Winter Park, FL 32789
    /2

    $560,000

    Sold Aug 28, 2026

    1122 Washington Ave Unit 7, Winter Park, FL 32789

    • 2 Beds
    • 2.5 Baths
    • 1,556 Sq Ft
    • Built 1978

    Last Sold Summary

    • 3% Below List Price
    • $360/SF
    • 13 Days On Market

    Current Estimated Value $539,735

    Last Listing Agent Cara Edwards ALL REAL ESTATE & INVESTMENTS

    1122 Washington Ave Unit 7, Winter Park, FL 32789
    • 645 N Interlachen Ave, Winter Park, FL 32789
      645 N Interlachen Ave, Winter Park, FL 32789
      645 N Interlachen Ave, Winter Park, FL 32789
      /68

      Est $1,132,953

      Not Listed For Sale

      645 N Interlachen Ave, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,766 Sq Ft
      • Built 1981
      645 N Interlachen Ave, Winter Park, FL 32789

      Last Sold Summary

      • 107 Days On Market

      Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

  • 240 N Phelps Ave, Winter Park, FL 32789
    240 N Phelps Ave, Winter Park, FL 32789
    240 N Phelps Ave, Winter Park, FL 32789
    /44

    $2,050,000

    New Construction Open Sat 1PM - 3PM $200K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 2,889 Sq Ft

    240 N Phelps Ave, Winter Park, FL 32789

    A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort.The open-concept living areas are

    Nickolas McKee KELLER WILLIAMS WINTER PARK

    240 N Phelps Ave, Winter Park, FL 32789
  • 106 S Interlachen Ave Unit 118, Winter Park, FL 32789
    106 S Interlachen Ave Unit 118, Winter Park, FL 32789
    /2

    $1,200,000

    Sold Jul 24, 2026

    106 S Interlachen Ave Unit 118, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft
    • Built 1971

    Last Sold Summary

    • 20% Below List Price
    • $654/SF
    • 151 Days On Market

    Current Estimated Value $1,209,547

    Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    106 S Interlachen Ave Unit 118, Winter Park, FL 32789
    • 200 S Interlachen Ave Unit 450, Winter Park, FL 32789
      200 S Interlachen Ave Unit 450, Winter Park, FL 32789
      200 S Interlachen Ave Unit 450, Winter Park, FL 32789
      /47

      Est $2,223,282

      Not Listed For Sale

      200 S Interlachen Ave Unit 450, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 3,110 Sq Ft
      • Built 2001
      200 S Interlachen Ave Unit 450, Winter Park, FL 32789

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Lisa Shear FANNIE HILLMAN & ASSOCIATES

  • 2501 Winter Park Rd, Winter Park, FL 32789
    2501 Winter Park Rd, Winter Park, FL 32789
    2501 Winter Park Rd, Winter Park, FL 32789
    /50

    $1,649,000

    $146K PRICE DROP Under Contract
    • 5 Beds
    • 3.5 Baths
    • 3,304 Sq Ft

    2501 Winter Park Rd, Winter Park, FL 32789

    Under contract-accepting backup offers. PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park is rare. Finding one built this recently—with this level of craftsmanship, infrastructure, and thoughtful design—is even rarer.Built by Barefoot Brothers in 2014 and thoughtfully designed for an active family that values

    Jill Healey KELLER WILLIAMS WINTER PARK

    2501 Winter Park Rd, Winter Park, FL 32789
  • 1400 S Pennsylvania Ave, Winter Park, FL 32789
    1400 S Pennsylvania Ave, Winter Park, FL 32789
    /2

    $1,300,000

    Sold Jan 02, 2026

    1400 S Pennsylvania Ave, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,310 Sq Ft
    • Built 1962

    Last Sold Summary

    • 6% Below List Price
    • $563/SF
    • 333 Days On Market

    Current Estimated Value $1,250,586

    Last Listing Agent Jack Keller JACK KELLER INC

    1400 S Pennsylvania Ave, Winter Park, FL 32789
    • 1272 S Pennsylvania Ave Unit 11, Winter Park, FL 32789
      1272 S Pennsylvania Ave Unit 11, Winter Park, FL 32789
      1272 S Pennsylvania Ave Unit 11, Winter Park, FL 32789
      /38

      Est $843,721

      Not Listed For Sale

      1272 S Pennsylvania Ave Unit 11, Winter Park, FL 32789

      • 3 Beds
      • 2.5 Baths
      • 1,957 Sq Ft
      • Built 2007
      1272 S Pennsylvania Ave Unit 11, Winter Park, FL 32789

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  • 2417 Chantilly Ave, Winter Park, FL 32789
    2417 Chantilly Ave, Winter Park, FL 32789
    2417 Chantilly Ave, Winter Park, FL 32789
    /10

    $1,579,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,718 Sq Ft

    2417 Chantilly Ave, Winter Park, FL 32789

    Under Construction. UNDER CONSTRUCTION | LUXURY NEW BUILD | Presented by LUIH Luxury HomesWelcome to 2417 Chantilly Avenue, an exceptional luxury new construction residence in beautiful Winter Park, Florida, where sophisticated design, elevated finishes, and effortless indoor-outdoor living come together.This stunning 4-bedroom, 3.5-bath home features an expansive open-concept floor plan

    Amanda Wood RE/MAX EXCLUSIVE COLLECTION

    2417 Chantilly Ave, Winter Park, FL 32789
  • 887 Georgia Ave, Winter Park, FL 32789
    887 Georgia Ave, Winter Park, FL 32789
    /2

    $4,500,000

    Sold Apr 30, 2026

    887 Georgia Ave, Winter Park, FL 32789

    • 6 Beds
    • 5.5 Baths
    • 5,759 Sq Ft
    • Built 1924

    Last Sold Summary

    • 31% Below List Price
    • $781/SF
    • 222 Days On Market

    Current Estimated Value $4,547,802

    Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

    887 Georgia Ave, Winter Park, FL 32789
    • 101 S New York Ave Unit 301, Winter Park, FL 32789
      101 S New York Ave Unit 301, Winter Park, FL 32789
      101 S New York Ave Unit 301, Winter Park, FL 32789
      /66

      Est $1,660,303

      Not Listed For Sale

      101 S New York Ave Unit 301, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 3,176 Sq Ft
      • Built 2008
      101 S New York Ave Unit 301, Winter Park, FL 32789

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Edward Johnston COLDWELL BANKER REALTY

  • 525 Ololu Dr, Winter Park, FL 32789
    525 Ololu Dr, Winter Park, FL 32789
    525 Ololu Dr, Winter Park, FL 32789
    /40

    $490,900

    Open Sat 12PM - 4PM $24K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,786 Sq Ft

    525 Ololu Dr, Winter Park, FL 32789

    Back on market. Previous contract was canceled due to buyer circumstances. Seller is motivated and ready to move forward.Fully renovated and carefully reimagined, this 3 bedroom, 3 bath residence in the heart of Winter Park offers a compelling combination of quality, functionality, and long term value. Designed with intention and attention to detail, the property presents a refreshed, modern

    Gisela Rojas CAISSA REALTY INVESTMENT INC

    525 Ololu Dr, Winter Park, FL 32789
  • 130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789
    130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789
    /2

    $465,000

    Sold Oct 21, 2025

    130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789

    • 2 Beds
    • 2.5 Baths
    • 1,536 Sq Ft
    • Built 1986

    Last Sold Summary

    • 3% Below List Price
    • $303/SF
    • 75 Days On Market

    Current Estimated Value $448,900

    Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

    130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789
    • 100 S Virginia Ave Unit 319, Winter Park, FL 32789
      100 S Virginia Ave Unit 319, Winter Park, FL 32789
      /2

      Est $1,119,479

      Not Listed For Sale

      100 S Virginia Ave Unit 319, Winter Park, FL 32789

      • 3 Beds
      • 3 Baths
      • 2,649 Sq Ft
      • Built 2008
      100 S Virginia Ave Unit 319, Winter Park, FL 32789

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  • 1836 Whitehall Dr, Winter Park, FL 32789
    1836 Whitehall Dr, Winter Park, FL 32789
    1836 Whitehall Dr, Winter Park, FL 32789
    /70

    $2,995,000

    New Construction $505K PRICE DROP
    • 5 Beds
    • 6.5 Baths
    • 4,168 Sq Ft

    1836 Whitehall Dr, Winter Park, FL 32789

    Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil island paradise, this new custom home by Urban Perch, A Boutique Home Builder, offers a timeless front elevation, exquisite finishes inside and out, and unobstructed views of the beautiful outdoors from almost every room. Totaling 4,168 square feet, this five-bedroom, five-bath

    Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

    1836 Whitehall Dr, Winter Park, FL 32789
  • 700 Pinetree Rd, Winter Park, FL 32789
    700 Pinetree Rd, Winter Park, FL 32789
    /2

    $3,278,530

    Sold May 20, 2026

    700 Pinetree Rd, Winter Park, FL 32789

    • 4 Beds
    • 4.5 Baths
    • 3,897 Sq Ft
    • Built 1955

    Last Sold Summary

    • $841/SF
    • 1 Day On Market

    Current Estimated Value $3,153,423

    Last Listing Agent Lauren Richardson FANNIE HILLMAN & ASSOCIATES

    700 Pinetree Rd, Winter Park, FL 32789

Showing Results 601 - 640, Page 16 of 18

Florida Orange County Winter Park

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group