Homes in ZIP Code 32789

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  $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 $941,098

  Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

  1840 Biscayne Dr, 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

  Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES
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  /64

  $2,995,000

  • 5 Beds
  • 4.5 Baths
  • 4,091 Sq Ft

  670 Williams Dr, Winter Park, FL 32789

  This stunning custom residence built by respected Winter Park Builder Charles Clayton blends classic elegance with refined modern comfort, offering seamless indoor–outdoor living and impeccable craftsmanship throughout. From the manicured lawn and stately traditional exterior to the welcoming front porch with old Detroit brick, the home’s curb appeal sets a tone of understated luxury, all wrapped

  Brian Mitnik RE/MAX 200 REALTY

  670 Williams Dr, Winter Park, FL 32789
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  $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 $1,480,024

  Last Listing Agent Chuck Massab FANNIE HILLMAN & ASSOCIATES

  747 Mcintyre Ave, Winter Park, FL 32789
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  /34

  Est $1,445,508 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

  Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES
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  /41

  $879,000

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

  100 S Interlachen Ave Unit 503, Winter Park, FL 32789

  Welcome to The Cloisters, one of Winter Park’s established lakefront communities, ideally between Park Avenue and Lake Osceola. This top-floor residence, rarely available in the building, offers a turnkey lifestyle with exceptional updates and peaceful water views. The home’s oversized screened balcony, complete with a custom awning, creates an uncommon open-air retreat that overlooks the

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 503, Winter Park, FL 32789
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  /2

  $1,175,000 Sold Mar 27, 2025

  1681 Blue Ridge Rd, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,762 Sq Ft
  • Built 1960

  Last Sold Summary

  • 16% Below List Price
  • $425/SF
  • 89 Days On Market

  Current Estimated Value $1,198,483

  Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

  1681 Blue Ridge Rd, Winter Park, FL 32789
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  /22

  Est $1,559,532 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

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY
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  /45

  $1,645,000 Open Sun 1PM - 3PM

  • 5 Beds
  • 5.5 Baths
  • 3,609 Sq Ft

  234 Detmar Dr, Winter Park, FL 32789

  Nestled behind gates in the heart of Winter park, this enchanting 1930's residence blends historic charm with many recent upgrades. The beautifully renovated kitchen anchors the home, while the downstairs primary suite offers privacy and comfort with an elegant spa inspired bath. The detached one bedroom guest house is perfect for houseguests, a home office or multi-generational living. The main

  Nicole Seybold FANNIE HILLMAN & ASSOCIATES

  234 Detmar Dr, Winter Park, FL 32789
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  /2

  $360,000 Sold Nov 20, 2025

  611 Ololu Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,145 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Above List Price
  • $314/SF
  • 7 Days On Market

  Current Estimated Value $362,071

  Last Listing Agent Amanda Johnson HOMERUN REALTY, LLC

  611 Ololu Dr, Winter Park, FL 32789
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  /2

  Est $1,139,911 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

  • 4% Above List Price
  • $399/SF
  • 51 Days On Market

  Last Sold Price $1,099,717

  Last Listing Agent Tiffany Grindstaff KELLY PRICE & COMPANY LLC
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  /26

  $335,000

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789

  Tucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfect blend of privacy, style, and unbeatable location. Just one block from Winter Park Village and only a mile from Park Avenue, you’ll enjoy walkable access to some of the area’s best dining, shopping, and entertainment. Located on the first floor, this beautifully renovated 2-bed, 2-bath home features an open

  Brandon Geers COMPASS FLORIDA LLC

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789
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  /2

  $1,000,500 Sold Dec 11, 2025

  210 E Rockwood Way, Winter Park, FL 32789

  • 3 Beds
  • 1.5 Baths
  • 1,431 Sq Ft
  • Built 1950

  Last Sold Summary

  • $699/SF
  • 0 Days On Market

  Current Estimated Value $968,531

  Last Listing Agent Penny Puente DALTON WADE INC

  210 E Rockwood Way, Winter Park, FL 32789
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  /17

  Est $296,961 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

  • 1% Below List Price
  • $423/SF
  • 24 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Richard Palmano PALMANO GROUP RE BROKERAGE LLC
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  /12

  $4,500,000

  • Land
  • 0.48 Acre
  • $9,375,000 per Acre

  503 N Interlachen Ave, Winter Park, FL 32789

  JUST LISTED - RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK - OFFERED AT $4,999,000!!! Zoned R-3, this multi-family, prime piece of land is ready for development. Luxury townhomes or condos, nothing but pure potential. Located near the intersection of N. Interlachen Avenue and Canton Avenue, this parcel is just 1-block to Park Avenue's boutique shops, award-winning restaurants, and esteemed

  Kelly Price KELLY PRICE & COMPANY LLC

  503 N Interlachen Ave, Winter Park, FL 32789
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  /2

  $145,000 Sold May 02, 2025

  1695 Lee Rd Unit D206, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Built 1966

  Last Sold Summary

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

  Current Estimated Value $142,518

  Last Listing Agent Justin Adams EXP REALTY LLC

  1695 Lee Rd Unit D206, Winter Park, FL 32789
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  /2

  Est $319,124 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

  • 3% Below List Price
  • $465/SF
  • 99 Days On Market

  Last Sold Price $329,900

  Last Listing Agent Lila Amalbert LPT REALTY, LLC
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  /6

  $375,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  770 Carver St, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to 770 Carver Street in the highly sought after Winter Park, Florida! This charming three-bedroom, one-and-a-half-bath home offers nearly 1,300 square feet of versatile living space, brimming with potential. Whether you’re a potential homeowner or an investor/developer seeking your next opportunity, this property presents an ideal canvas to bring

  Maria Stinson LEGENDS REALTY

  770 Carver St, Winter Park, FL 32789
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  /2

  $780,000 Sold May 05, 2025

  106 S Interlachen Ave Unit 317, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,351 Sq Ft
  • Built 1971

  Last Sold Summary

  • $577/SF
  • 0 Days On Market

  Current Estimated Value $759,124

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

  106 S Interlachen Ave Unit 317, Winter Park, FL 32789
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  /24

  Est $340,983 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

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES
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  /39

  $1,690,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 3,048 Sq Ft

  1570 Palmer Ave, Winter Park, FL 32789

  Located in the heart of Winter Park, this beautifully appointed 3,048 sq. ft. residence with saltwater pool and spa offers an ideal blend of comfort, style, and functionality. Designed for both everyday living and entertaining, the home features an open and inviting floor plan filled with natural light and high-end finishes throughout. The gourmet kitchen is equipped with granite countertops,

  David Auerbach PARK TOWN REAL ESTATE LLC

  1570 Palmer Ave, Winter Park, FL 32789
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  /2

  $555,000 Sold Jan 29, 2026

  1267 Michigan Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,798 Sq Ft
  • Built 2019

  Last Sold Summary

  • 17% Below List Price
  • $309/SF
  • 88 Days On Market

  Current Estimated Value $604,342

  Last Listing Agent Megan Cross FANNIE HILLMAN & ASSOCIATES

  1267 Michigan Ave, Winter Park, FL 32789
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  /22

  Est $478,008 Not Listed For Sale

  311 E Morse Blvd Unit 6-8, Winter Park, FL 32789

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

  311 E Morse Blvd Unit 6-8, Winter Park, FL 32789

  Last Sold Summary

  • 9% Below List Price
  • $594/SF
  • 25 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES
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  $4,197,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 4,782 Sq Ft

  1782 Pine Ave, Winter Park, FL 32789

  Step into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiece in the heart of City of Winter Park. This five-bedroom seven-bath home that includes a private in-law suite offers plenty of exquisite interior features. The home welcomes you with a beautifully designed 16 ft wide circular driveway wrapped

  Prentice Williams KELLER WILLIAMS ADVANTAGE REALTY

  1782 Pine Ave, Winter Park, FL 32789
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  /2

  $330,000 Sold Jul 23, 2025

  700 Melrose Ave J 1 Ave Unit J1, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft
  • Built 1964

  Last Sold Summary

  • 16% Below List Price
  • $307/SF
  • 303 Days On Market

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave J 1 Ave Unit J1, Winter Park, FL 32789
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  /32

  Est $464,152 Not Listed For Sale

  311 E Morse Blvd Unit 6-2, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 1,192 Sq Ft
  • Built 1960

  311 E Morse Blvd Unit 6-2, Winter Park, FL 32789

  Last Sold Summary

  • 19% Above List Price
  • $327/SF
  • 80 Days On Market

  Last Sold Price $390,000

  Last Listing Agent Anthony Consalvo FLORIDA ONE REAL ESTATE LLC
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  /10

  $1,195,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,525 Sq Ft

  1860 Staunton Ave, Winter Park, FL 32789

  Pre-Construction. To be built. Elevate your lifestyle with a rare chance to build your dream home in the coveted Killarney Shores neighborhood. This exclusive opportunity is in one of the last Winter Park neighborhoods where fully custom new construction is still attainable under $1.3M. A premier build team, curated by The Hope Group, will include Deep Roots Construction, MJS Designers, and

  Leighton Hope COMPASS FLORIDA LLC

  1860 Staunton Ave, Winter Park, FL 32789
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  /2

  $175,000 Sold Apr 11, 2025

  700 Melrose Ave Unit E6, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft
  • Built 1964

  Last Sold Summary

  • 22% Below List Price
  • $240/SF
  • 230 Days On Market

  Current Estimated Value $177,719

  Last Listing Agent Milton James COLDWELL BANKER REALTY

  700 Melrose Ave Unit E6, Winter Park, FL 32789
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  /6

  Est $2,091,515 Not Listed For Sale

  140 E Morse Blvd Unit I, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,291 Sq Ft
  • Built 2008

  140 E Morse Blvd Unit I, Winter Park, FL 32789

  Last Sold Summary

  • 5% Below List Price
  • $960/SF
  • 65 Days On Market

  Last Sold Price $2,200,000

  Last Listing Agent Andrea Sider, PA KELLER WILLIAMS WINTER PARK
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  /21

  $850,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,479 Sq Ft

  2119 Howard Dr, Winter Park, FL 32789

  Welcome to this charming residence in the heart of sought-after Winter Park. Pride of ownership is evident throughout this home and significant updates include a new roof being installed before closing, HVAC replaced in 2020, updated electrical in 2023 and a plumbing repipe in 2012. The spacious layout provides comfortable living and entertaining with a formal living room, formal dining room and

  Jill Healey KELLER WILLIAMS WINTER PARK

  2119 Howard Dr, Winter Park, FL 32789
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  /2

  $2,495,000 Sold Jul 22, 2025

  940 Lincoln Cir, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,551 Sq Ft
  • Built 1995

  Last Sold Summary

  • 26% Below List Price
  • $703/SF
  • 47 Days On Market

  Current Estimated Value $2,514,447

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  940 Lincoln Cir, Winter Park, FL 32789
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  /51

  Est $698,490 Not Listed For Sale

  106 S Interlachen Ave Unit 416, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft
  • Built 1971

  106 S Interlachen Ave Unit 416, Winter Park, FL 32789

  Last Sold Summary

  • 6% Above List Price
  • $577/SF
  • 55 Days On Market

  Last Sold Price $660,000

  Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY
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  /12

  $1,750,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,350 Sq Ft

  1840 Anzle Ave, Winter Park, FL 32789

  Under Construction. NEW CONSTRUCTION – Under Construction. Welcome to Winter Park! This stunning modern residence is meticulously designed and ideally located near everything. This beautifully crafted home features 4 bedrooms, 2.5 bathrooms, and 2,350 square feet of living space, plus an additional 1,247 square feet of terraces and lanai. The open-concept kitchen showcases quartz countertops,

  Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

  1840 Anzle Ave, Winter Park, FL 32789
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  /2

  $900,000 Sold Aug 29, 2025

  3011 Temple Trail, Winter Park, FL 32789

  • 5 Beds
  • 2.5 Baths
  • 2,406 Sq Ft
  • Built 1965

  Last Sold Summary

  • 10% Below List Price
  • $374/SF
  • 83 Days On Market

  Current Estimated Value $899,717

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  3011 Temple Trail, Winter Park, FL 32789
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  /39

  Est $694,253 Not Listed For Sale

  104 S Interlachen Ave Unit 414, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft
  • Built 1971

  104 S Interlachen Ave Unit 414, Winter Park, FL 32789

  Last Sold Summary

  • 7% Above List Price
  • $513/SF
  • 37 Days On Market

  Last Sold Price $650,000

  Last Listing Agent James Lyon COLLADO REAL ESTATE
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  /7

  $489,000

  • Land
  • 0.21 Acre
  • $2,328,571 per Acre

  3601 Midiron Dr, Winter Park, FL 32789

  Ready to build your dream home or invest in one of Winter Park’s most desirable locations? This oversized, one-of-a-kind lot is ideally situated just across from Dubsdread Golf Course and only minutes from Park Avenue, Winter Park Village, dining, shopping, and entertainment. Enjoy convenient access to major roads while still being nestled in a highly sought-after neighborhood. Located within a

  Juliana Usquiano EMPIRE NETWORK REALTY

  3601 Midiron Dr, Winter Park, FL 32789
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  /2

  $4,150,000 Sold Feb 18, 2026

  702 Via Bella, Winter Park, FL 32789

  • 4 Beds
  • 5.5 Baths
  • 3,720 Sq Ft
  • Built 2025

  Last Sold Summary

  • 11% Below List Price
  • $1,116/SF
  • 149 Days On Market

  Current Estimated Value $3,911,561

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

  702 Via Bella, Winter Park, FL 32789
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  /30

  Est $1,120,766 Not Listed For Sale

  100 S Interlachen Ave Unit 301, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,639 Sq Ft
  • Built 1971

  100 S Interlachen Ave Unit 301, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $675/SF
  • 6 Days On Market

  Last Sold Price $1,107,000

  Last Listing Agent Vincent Scarlatos CORCORAN PREMIER REALTY
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  $2,100,000

  • 2 Beds
  • 2 Baths
  • 1,900 Sq Ft

  311 E Morse Blvd Unit 2-5, Winter Park, FL 32789

  Enjoy the Winter Park lifestyle in this spacious 2-bedroom, 2-bath lakefront condo offering 1,900 square feet in the heart of downtown Winter Park. Enjoy serene lake views from the 120 sq ft screened porch—perfect for morning coffee or evening wine. The light-filled living area features soaring 8 ft 10 in ceilings, creating an open, airy atmosphere. A cozy family room offers built-in shelving and

  Megan Cross FANNIE HILLMAN & ASSOCIATES

  311 E Morse Blvd Unit 2-5, Winter Park, FL 32789
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  /2

  $190,000 Sold Mar 20, 2026

  1250 S Denning Dr Unit 104, Winter Park, FL 32789

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

  Last Sold Summary

  • 17% Below List Price
  • $209/SF
  • 60 Days On Market

  Current Estimated Value $213,088

  Last Listing Agent John Harbuck SERHANT

  1250 S Denning Dr Unit 104, Winter Park, FL 32789

Showing Results 521 - 560, Page 14 of 18