Homes in ZIP Code 32789

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  /20

  Est $368,170 Not Listed For Sale

  700 Melrose Ave Unit C2, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,448 Sq Ft
  • Built 1964

  700 Melrose Ave Unit C2, Winter Park, FL 32789

  Last Sold Summary

  • 13% Above List Price
  • $224/SF
  • 35 Days On Market

  • Last Sold Price $325,000
  • Jun 30, 2023

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES
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  /2

  $4,550,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 5,253 Sq Ft

  1701 Summerland Ave, Winter Park, FL 32789

  Under Construction. Stunning Winter Park new build by Vimaro Homes in Park Grove.

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1701 Summerland Ave, Winter Park, FL 32789
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  /2

  $1,480,000 Sold Sep 19, 2025

  1742 Barcelona Way, Winter Park, FL 32789

  • 5 Beds
  • 8 Baths
  • 3,626 Sq Ft
  • Built 1973

  Last Sold Summary

  • 18% Below List Price
  • $408/SF
  • 81 Days On Market

  Current Estimated Value $1,516,899

  Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

  1742 Barcelona Way, Winter Park, FL 32789
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  /44

  Est $2,229,464 Not Listed For Sale

  200 S Interlachen Ave Unit 400, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,074 Sq Ft
  • Built 2001

  200 S Interlachen Ave Unit 400, Winter Park, FL 32789

  Last Sold Summary

  • 5% Below List Price
  • $764/SF
  • 40 Days On Market

  • Last Sold Price $2,350,000
  • Jun 07, 2024

  Last Listing Agent Lisa Shear FANNIE HILLMAN & ASSOCIATES
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  /66

  $3,250,000

  • 5 Beds
  • 4.5 Baths
  • 5,243 Sq Ft

  141 Glenridge Way, Winter Park, FL 32789

  Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over 5,200 square feet, offering 5 bedrooms, 4.5 baths, a designated office, a large, versatile media/game room, a 3-car garage, and an expansive

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  141 Glenridge Way, Winter Park, FL 32789
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  /2

  $1,500,000 Sold May 14, 2025

  1741 Pine Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,297 Sq Ft
  • Built 2002

  Last Sold Summary

  • $455/SF
  • 7 Days On Market

  Current Estimated Value $1,543,493

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  1741 Pine Ave, Winter Park, FL 32789
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  /2

  Est $2,718,294 Not Listed For Sale

  315 E New England Ave Unit 30, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,130 Sq Ft
  • Built 2008

  315 E New England Ave Unit 30, Winter Park, FL 32789

  Last Sold Summary

  • 3% Below List Price
  • $895/SF
  • 1 Day On Market

  • Last Sold Price $2,800,000
  • Mar 17, 2025

  Last Listing Agent Michelle Daniels COLDWELL BANKER REALTY
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  /37

  $164,000 Pending

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  2500 Lee Rd Unit 219, Winter Park, FL 32789

  Welcome to life on Lake Killarney, one of Winter Park’s most sought-after lakefront communities! This charming 2-bedroom, 1-bathroom condo offers an unbeatable location and resort-style amenities—perfect for those seeking the true Florida lifestyle.Enjoy direct access to Lake Killarney, where residents can take advantage of boat slips available at a low cost on a first-come, first-serve basis, as

  Nicole Van Treese SUNDIAL REAL ESTATE LLC

  2500 Lee Rd Unit 219, Winter Park, FL 32789
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  /2

  $560,000 Sold Aug 19, 2025

  1339 Orchid Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 789 Sq Ft
  • Built 1953

  Last Sold Summary

  • 12% Below List Price
  • $710/SF
  • 46 Days On Market

  Current Estimated Value $529,942

  Last Listing Agent Barbara Allen ABIDE REALTY

  1339 Orchid Ave, Winter Park, FL 32789
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  /2

  Est $1,538,627 Not Listed For Sale

  315 E New England Ave Unit 9, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,637 Sq Ft
  • Built 2007

  315 E New England Ave Unit 9, Winter Park, FL 32789

  Last Sold Summary

  • 7% Below List Price
  • $1,008/SF
  • 5 Days On Market

  • Last Sold Price $1,650,000
  • Jan 02, 2025

  Last Listing Agent Anna Lohr URBANISTA BROKERS
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  /35

  $490,090 Pending

  • 2 Beds
  • 2 Baths
  • 1,609 Sq Ft

  518 Shoreview Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. NESTLED IN THE HEART OF HISTORIC WINTER PARK, THIS CHARMING RESIDENCE AT 518 SHOREVIEW AVE OFFERS TIMELESS CHARCTER. JUST STEPS FROM BEAUTIFUL LAKE KILARNEY. INSIDE, YOU WILL FIND STUNNING HARDWOOD FLOORS THAT ADD WARMTH AND ELEGANCE THROUGHOUT, ALONG WITH AN UPDATED PRIMARY BATHROOM FEATURING A RELAXING GARDEN TUB.THE INVITING FLORIDA ROOM PROVIDES

  Kendra Heckart UNITED REAL ESTATE PREFERRED

  518 Shoreview Ave, Winter Park, FL 32789
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  /2

  $975,000 Sold Mar 25, 2026

  456 Carolina Ave, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 1,615 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $604/SF
  • 9 Days On Market

  Current Estimated Value $1,049,938

  Last Listing Agent Heather Frazee FANNIE HILLMAN & ASSOCIATES

  456 Carolina Ave, Winter Park, FL 32789
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  /100

  Est $2,959,116 Not Listed For Sale

  300 S Interlachen Ave Unit 303, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,355 Sq Ft
  • Built 2005

  300 S Interlachen Ave Unit 303, Winter Park, FL 32789

  Last Sold Summary

  • 12% Below List Price
  • $999/SF
  • 11 Days On Market

  • Last Sold Price $3,350,000
  • May 24, 2024

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC
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  /44

  $4,650,000 Pending

  • 4 Beds
  • 6.5 Baths
  • 6,242 Sq Ft

  1760 Via Venetia, Winter Park, FL 32789

  Under contract-accepting backup offers. Presenting an extraordinary southern traditional estate in the heart of the coveted Vias of Winter Park, a residence that effortlessly blends timeless architecture with exceptional craftsmanship. This stunning home, designed by acclaimed architect Gary Hancock, made its debut as the Southeast Builder’s Conference Showhouse for two consecutive years, a

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1760 Via Venetia, Winter Park, FL 32789
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  /2

  $475,000 Sold Oct 14, 2025

  621 Symonds Ave, Winter Park, FL 32789

  • Land
  • 5,662 Sq Ft
  • $3,653,846 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 147 Days On Market

  Current Estimated Value $471,230

  Last Listing Agent Emily Williams FANNIE HILLMAN & ASSOCIATES

  621 Symonds Ave, Winter Park, FL 32789
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  /24

  Est $223,936 Not Listed For Sale

  1250 S Denning Dr Unit 126, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 893 Sq Ft
  • Built 1967

  1250 S Denning Dr Unit 126, Winter Park, FL 32789

  Last Sold Summary

  • 2% Above List Price
  • $245/SF
  • 66 Days On Market

  • Last Sold Price $219,025
  • Feb 02, 2024

  Last Listing Agent Shahram Sondi SHAHRAM SONDI + CO.
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  /59

  $1,390,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,253 Sq Ft

  501 Lakeview Ave, Winter Park, FL 32789

  MOVE-IN READY! Construction Completed! Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 1⁄2 baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright loft that

  Marie Ledbetter COLDWELL BANKER REALTY

  501 Lakeview Ave, Winter Park, FL 32789
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  /2

  $230,000 Sold May 30, 2025

  1500 Gay Rd Unit 10C, Winter Park, FL 32789

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

  Last Sold Summary

  • 7% Below List Price
  • $224/SF
  • 75 Days On Market

  Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 10C, Winter Park, FL 32789
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  /41

  Est $1,041,484 Not Listed For Sale

  100 S Virginia Ave Unit 316, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,599 Sq Ft
  • Built 2008

  100 S Virginia Ave Unit 316, Winter Park, FL 32789

  Last Sold Summary

  • 8% Above List Price
  • $371/SF
  • 140 Days On Market

  • Last Sold Price $965,000
  • May 24, 2023

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES
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  /65

  $1,550,000 New Construction

  • 5 Beds
  • 4 Baths
  • 3,164 Sq Ft

  1523 Miller Ave, Winter Park, FL 32789

  BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. This 3,164 sqft home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped living, kitchen, and dining area

  Eric Trumble II CHARLES RUTENBERG REALTY ORLANDO

  1523 Miller Ave, Winter Park, FL 32789
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  /2

  $1,740,000 Sold Aug 29, 2025

  443 Beloit Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,964 Sq Ft
  • Built 1983

  Last Sold Summary

  • 3% Below List Price
  • $587/SF
  • 0 Days On Market

  Current Estimated Value $1,749,250

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  443 Beloit Ave, Winter Park, FL 32789
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  /31

  Est $1,094,503 Not Listed For Sale

  100 S Virginia Ave Unit 315, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,599 Sq Ft
  • Built 2009

  100 S Virginia Ave Unit 315, Winter Park, FL 32789

  Last Sold Summary

  • 3% Below List Price
  • $433/SF
  • 10 Days On Market

  • Last Sold Price $1,125,000
  • Jul 10, 2024

  Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES
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  /30

  $484,000

  • 4 Beds
  • 2 Baths
  • 1,718 Sq Ft

  240 Orange Terrace Dr, Winter Park, FL 32789

  PRICE IMPROVEMENT - SELLER MOTIVATED - MOVE IN READY - NO HOA, PRIME WINTER PARK LOCATION, CLOSE TO I-4! Nestled in the heart of Winter Park near Lake Killarney, this beautifully updated 4-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and style. Just minutes from Fairbanks and I-4, you’ll enjoy quick access to top shopping, dining, and all that Winter Park has to

  Susan Pinnock A+ REALTY PROFESSIONALS, INC

  240 Orange Terrace Dr, Winter Park, FL 32789
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  /2

  $940,000 Sold Aug 29, 2025

  1840 Biscayne Dr, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,646 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Below List Price
  • $355/SF
  • 17 Days On Market

  Current Estimated Value $938,912

  Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

  1840 Biscayne Dr, Winter Park, FL 32789
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  /34

  Est $1,438,924 Not Listed For Sale

  101 S New York Ave Unit 309, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,966 Sq Ft
  • Built 2008

  101 S New York Ave Unit 309, Winter Park, FL 32789

  Last Sold Summary

  • 11% Below List Price
  • $548/SF
  • 16 Days On Market

  • Last Sold Price $1,625,000
  • Apr 15, 2024

  Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES
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  /28

  $240,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 908 Sq Ft

  1250 S Denning Dr Unit 117, Winter Park, FL 32789

  Under contract-accepting backup offers. Remodeled two-bedroom, one-and-one-half-bath residence in the Mead Garden Condominium community. Spanning 908 square feet, this first-floor home features a move-in-ready interior with an open-concept layout, luxury vinyl plank flooring throughout, and in-unit washer and dryer hookups, a rare offering within the building, located in the half bath. The

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  1250 S Denning Dr Unit 117, Winter Park, FL 32789
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  /2

  $669,000 Sold Mar 26, 2026

  681 Overspin Dr, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,220 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $301/SF
  • 34 Days On Market

  Current Estimated Value $664,691

  Last Listing Agent Gail Higley RE/MAX SELECT GROUP

  681 Overspin Dr, Winter Park, FL 32789
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  /22

  Est $1,563,807 Not Listed For Sale

  101 S New York Ave Unit 304, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,118 Sq Ft
  • Built 2008

  101 S New York Ave Unit 304, Winter Park, FL 32789

  Last Sold Summary

  • 4% Above List Price
  • $481/SF
  • 32 Days On Market

  • Last Sold Price $1,500,000
  • Jun 06, 2024

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY
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  /31

  $1,495,000

  • 4 Beds
  • 3.5 Baths
  • 2,838 Sq Ft

  2408 Lafayette Ave, Winter Park, FL 32789

  This custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set apart for

  Matthew Burks CORCORAN PREMIER REALTY

  2408 Lafayette Ave, Winter Park, FL 32789
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  /2

  $1,525,000 Sold Jun 18, 2025

  747 Mcintyre Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,457 Sq Ft
  • Built 1950

  Last Sold Summary

  • 2% Above List Price
  • $1,047/SF
  • 2 Days On Market

  Current Estimated Value $1,438,122

  Last Listing Agent Chuck Massab FANNIE HILLMAN & ASSOCIATES

  747 Mcintyre Ave, Winter Park, FL 32789
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  /2

  Est $1,124,731 Not Listed For Sale

  100 S Virginia Ave Unit 201, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,756 Sq Ft
  • Built 2008

  100 S Virginia Ave Unit 201, Winter Park, FL 32789

  Last Sold Summary

  • 2% Above List Price
  • $399/SF
  • 51 Days On Market

  • Last Sold Price $1,099,717
  • Dec 30, 2024

  Last Listing Agent Tiffany Grindstaff KELLY PRICE & COMPANY LLC
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  /37

  $2,750,000

  • 5 Beds
  • 5 Baths
  • 4,917 Sq Ft

  1630 Lasbury Ave, Winter Park, FL 32789

  The seller has just completed a full renovation.Bathrooms have been entirely gutted and updated with new tiles, fixtures, and lighting. All lighting throughout the home has been replaced, and fresh paint has been applied throughout. Situated on a spacious double lot spanning over 1/3 acres, this home offers a private retreat, complete with an impressive 18 x 40 pool. The layout features

  Teresa Chris Harralson COMPASS FLORIDA, LLC

  1630 Lasbury Ave, Winter Park, FL 32789
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  /2

  $1,675,000 Sold May 08, 2026

  1560 Woodland Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,851 Sq Ft
  • Built 1990

  Last Sold Summary

  • 9% Below List Price
  • $435/SF
  • 16 Days On Market

  Current Estimated Value $1,823,155

  Last Listing Agent Chris Creegan CREEGAN GROUP

  1560 Woodland Ave, Winter Park, FL 32789
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  /17

  Est $291,849 Not Listed For Sale

  500 N Pennsylvania Ave Unit F, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 709 Sq Ft
  • Built 1981

  500 N Pennsylvania Ave Unit F, Winter Park, FL 32789

  Last Sold Summary

  • 3% Below List Price
  • $423/SF
  • 24 Days On Market

  • Last Sold Price $300,000
  • Sep 15, 2023

  Last Listing Agent Richard Palmano PALMANO GROUP RE BROKERAGE LLC
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  /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
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  /2

  $2,232,000 Sold Apr 17, 2026

  660 Osceola Ave Unit 101, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,714 Sq Ft
  • Built 1999

  Last Sold Summary

  • 3% Below List Price
  • $822/SF
  • 145 Days On Market

  Current Estimated Value $2,149,386

  Last Listing Agent Richard Traynor FLORIDA ONE REAL ESTATE LLC

  660 Osceola Ave Unit 101, Winter Park, FL 32789
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  /2

  Est $316,728 Not Listed For Sale

  500 N Pennsylvania Ave Unit E, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 709 Sq Ft
  • Built 1981

  500 N Pennsylvania Ave Unit E, Winter Park, FL 32789

  Last Sold Summary

  • 4% Below List Price
  • $465/SF
  • 99 Days On Market

  • Last Sold Price $329,900
  • Dec 23, 2024

  Last Listing Agent Lila Amalbert LPT REALTY, LLC
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  /78

  $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
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  /2

  $300,000 Sold Mar 27, 2026

  1313 S Denning Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1950

  Last Sold Summary

  • $176/SF

  Current Estimated Value $487,318

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  1313 S Denning Dr, Winter Park, FL 32789
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  /24

  Est $343,197 Not Listed For Sale

  311 E Morse Blvd Unit 7-3, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 540 Sq Ft
  • Built 1960

  311 E Morse Blvd Unit 7-3, Winter Park, FL 32789

  Last Sold Summary

  • 5% Below List Price
  • $667/SF
  • 100 Days On Market

  • Last Sold Price $360,000
  • May 19, 2023

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

Showing Results 481 - 520, Page 13 of 18