Homes in ZIP Code 32789

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  /2

  Est $318,992 Not Listed For Sale

  700 Melrose Ave Unit B4, Winter Park, FL 32789

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

  700 Melrose Ave Unit B4, Winter Park, FL 32789

  Last Sold Summary

  • 23% Above List Price
  • $242/SF
  • 0 Days On Market

  • Last Sold Price $260,000
  • Feb 28, 2025

  Last Listing Agent Anthony Consalvo FLORIDA ONE REAL ESTATE LLC
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  /55

  $1,995,000

  • 4 Beds
  • 3.5 Baths
  • 3,551 Sq Ft

  1813 Harland Park Dr, Winter Park, FL 32789

  Nestled within the highly sought-after Windsong community in Winter Park, this thoughtfully designed residence presents the perfect balance of functionality, comfort, and elevated indoor-outdoor living. This move-in ready home is sure to check all the boxes with 2 NEW HVAC units (2025), a downstairs Primary Suite, a convenient 1st floor private office/flex room, 2nd floor loft & bonus room, plus

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1813 Harland Park Dr, Winter Park, FL 32789
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  /2

  $260,000 Sold Jan 30, 2026

  1250 S Denning Dr Unit 213, Winter Park, FL 32789

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

  Last Sold Summary

  • 5% Below List Price
  • $286/SF
  • 114 Days On Market

  Current Estimated Value $257,106

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

  1250 S Denning Dr Unit 213, Winter Park, FL 32789
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  /23

  Est $206,236 Not Listed For Sale

  700 Melrose Ave Unit K4, Winter Park, FL 32789

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

  700 Melrose Ave Unit K4, Winter Park, FL 32789

  Last Sold Summary

  • 14% Below List Price
  • $329/SF
  • 27 Days On Market

  • Last Sold Price $240,000
  • Jun 18, 2024

  Last Listing Agent Isabella Martinez METROPOLITAN R.E SOLUTIONS INC
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  /68

  $2,279,000

  • 5 Beds
  • 4.5 Baths
  • 2,889 Sq Ft

  240 N Phelps Ave, Winter Park, FL 32789

  Brand new construction luxury home in the heart of Winter Park! This stunning two-story custom residence offers nearly 3,000 sq ft of heated living space with 5 bedrooms and 4 1/2 bathrooms. A soaring two-story foyer creates a dramatic first impression and opens into an expansive great room featuring 12-foot ceilings, wide-plank flooring, and abundant natural light. The family room showcases a

  Milena Fernandes GOLDEN GROUP REALTY LLC

  240 N Phelps Ave, Winter Park, FL 32789
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  /61

  $610,000 Sold Feb 10, 2026

  1451 Cavendish Rd, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,437 Sq Ft
  • Built 1971

  Last Sold Summary

  • 2% Below List Price
  • $424/SF

  Current Estimated Value $603,861

  Last Listing Agent Spencer Flory LoKation

  1451 Cavendish Rd, Winter Park, FL 32789
• 

  

  /22

  Est $206,344 Not Listed For Sale

  700 Melrose Ave Unit E26, Winter Park, FL 32789

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

  700 Melrose Ave Unit E26, Winter Park, FL 32789

  Last Sold Summary

  • 14% Below List Price
  • $327/SF
  • 4 Days On Market

  • Last Sold Price $239,000
  • Apr 10, 2024

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES
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  /8

  $358,000 Pending

  • Land
  • 6,969 Sq Ft
  • $2,237,500 per Acre

  2002 Indiana Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Great buildable lot centrally located close to I-4 for easy access. Please consult the zoning and planning Dept. for info and guidelines for building. The lot has single family homes on both sides of it and faces a retention pond area across the street. Front half of the lot is cleared. Back half of the lot is wooded. Paved road frontage. Sign on the

  David Nicholson DAWN REALTY

  2002 Indiana Ave, Winter Park, FL 32789
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  /2

  $1,000,000 Sold Nov 03, 2025

  215 Salvador Square, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,565 Sq Ft
  • Built 1973

  Last Sold Summary

  • 16% Below List Price
  • $390/SF
  • 44 Days On Market

  Current Estimated Value $1,039,572

  Last Listing Agent Carrie Bantel PREMIER SOTHEBY'S INTL. REALTY

  215 Salvador Square, Winter Park, FL 32789
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  /18

  Est $176,465 Not Listed For Sale

  1250 S Denning Dr Unit 107, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 658 Sq Ft
  • Built 1967

  1250 S Denning Dr Unit 107, Winter Park, FL 32789

  Last Sold Summary

  • 7% Below List Price
  • $289/SF
  • 3 Days On Market

  • Last Sold Price $190,000
  • Aug 25, 2023

  Last Listing Agent Victoria Epley PALMANO GROUP RE BROKERAGE LLC
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  /6

  $3,650,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,719 Sq Ft

  207 E Kings Way, Winter Park, FL 32789

  Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  207 E Kings Way, Winter Park, FL 32789
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  /2

  $675,000 Sold Nov 28, 2025

  2190 Temple Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 1956

  Last Sold Summary

  • 4% Below List Price
  • $468/SF
  • 108 Days On Market

  Current Estimated Value $721,677

  Last Listing Agent Sharon Mikol MAINFRAME REAL ESTATE

  2190 Temple Dr, Winter Park, FL 32789
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  /30

  Est $708,757 Not Listed For Sale

  100 S Interlachen Ave Unit 506, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,109 Sq Ft
  • Built 1971

  100 S Interlachen Ave Unit 506, Winter Park, FL 32789

  Last Sold Summary

  • 6% Above List Price
  • $604/SF
  • 85 Days On Market

  • Last Sold Price $670,000
  • Sep 08, 2023

  Last Listing Agent Victoria Epley PALMANO GROUP RE BROKERAGE LLC
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  /34

  $725,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,008 Sq Ft

  770 W Webster Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Stop the car! Develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased simultaneously, for a total of 75x200 or 15,000sq/ft. Next to the proposed Winter Park Commons project, walk to Winter Park Village, Hannibal Square, WP9 and Park Ave for top shopping, dining

  Lisa Gould KELLER WILLIAMS WINTER PARK

  770 W Webster Ave, Winter Park, FL 32789
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  /2

  $380,000 Sold Sep 26, 2025

  690 Osceola Ave Unit 209, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1969

  Last Sold Summary

  • 11% Below List Price
  • $331/SF
  • 34 Days On Market

  Current Estimated Value $386,618

  Last Listing Agent Mike Wang LOKATION

  690 Osceola Ave Unit 209, Winter Park, FL 32789
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  /29

  Est $988,733 Not Listed For Sale

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

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft
  • Built 1971

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

  Last Sold Summary

  • 2% Above List Price
  • $557/SF
  • 79 Days On Market

  • Last Sold Price $965,000
  • Jul 31, 2023

  Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY
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  /24

  $595,000

  • 3 Beds
  • 2 Baths
  • 1,434 Sq Ft

  1741 Westchester Ave, Winter Park, FL 32789

  In the sought-after Orwin Manor neighborhood, this beautifully updated one-story residence offers a seamless blend of comfort, style and convenience. Featuring three bedrooms and two baths, the home showcases an open-concept floor plan enhanced by engineered wood flooring that extends throughout every room, creating a cohesive and inviting living environment. The kitchen is thoughtfully updated

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1741 Westchester Ave, Winter Park, FL 32789
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  /2

  $440,000 Sold Aug 22, 2025

  3019 Northwood Blvd, Winter Park, FL 32789

  • 3 Beds
  • 1.5 Baths
  • 1,662 Sq Ft
  • Built 1953

  Last Sold Summary

  • 35% Below List Price
  • $265/SF
  • 98 Days On Market

  Current Estimated Value $467,045

  Last Listing Agent Robert Arnold SAND DOLLAR REALTY GROUP INC

  3019 Northwood Blvd, Winter Park, FL 32789
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  /2

  Not Listed For Sale

  100 S Interlachen Ave Unit 111, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 901 Sq Ft
  • Built 1971

  100 S Interlachen Ave Unit 111, Winter Park, FL 32789

  Last Sold Summary

  • $705/SF
  • 53 Days On Market

  • Last Sold Price $635,000
  • Apr 28, 2025

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES
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  /14

  $2,790,000

  • Land
  • 21,344 Sq Ft
  • $5,693,878 per Acre

  620 Pinetree Rd, Winter Park, FL 32789

  One of the last remaining opportunities to build on a truly exceptional street in the Winter Park Via’s, this .48-acre homesite offers a fantastic combination of location, scale, and design potential. Cleared and ready to build, the property is framed by a handful of soaring pine trees, creating a beautiful natural backdrop for a future residence.The current owners have thoughtfully

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  620 Pinetree Rd, Winter Park, FL 32789
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  /2

  $312,500 Sold Oct 21, 2025

  1308 S Pennsylvania Ave Unit 3, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 823 Sq Ft
  • Built 1983

  Last Sold Summary

  • 4% Below List Price
  • $380/SF
  • 9 Days On Market

  Current Estimated Value $309,463

  Last Listing Agent Livia Petraru EXP REALTY LLC

  1308 S Pennsylvania Ave Unit 3, Winter Park, FL 32789
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  /2

  Est $244,095 Not Listed For Sale

  1250 S Denning Dr Unit 105, Winter Park, FL 32789

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

  1250 S Denning Dr Unit 105, Winter Park, FL 32789

  Last Sold Summary

  • 6% Below List Price
  • $286/SF
  • 15 Days On Market

  • Last Sold Price $260,000
  • Sep 27, 2024

  Last Listing Agent Joe Devlin DEVLIN INVESTORS & ASSOCIATES
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  /43

  $1,130,000

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

  67 Cypress Ln, Maitland, FL 32751

  Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths.Step inside to discover hardwood floors flowing

  Kelly Price KELLY PRICE & COMPANY LLC

  67 Cypress Ln, Maitland, FL 32751
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  /2

  $1,690,000 Sold Mar 06, 2026

  1630 Chestnut Ave, Winter Park, FL 32789

  • 3 Beds
  • 4.5 Baths
  • 3,164 Sq Ft
  • Built 2021

  Last Sold Summary

  • 3% Below List Price
  • $534/SF
  • 70 Days On Market

  Current Estimated Value $1,694,955

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  1630 Chestnut Ave, Winter Park, FL 32789
• 

  

  /22

  Not Listed For Sale

  1500 Gay Rd Unit 21B, Winter Park, FL 32789

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

  1500 Gay Rd Unit 21B, Winter Park, FL 32789

  Last Sold Summary

  • $229/SF
  • 40 Days On Market

  • Last Sold Price $235,000
  • Jan 10, 2024

  Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC
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  /55

  $1,395,000

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

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

  Experience lakefront living in the heart of Winter Park. One of only two residences in The Cloisters with soaring 9-foot ceilings, this first-floor, three-bedroom, two-bath home offers a rare blend of privacy, scale and panoramic Lake Osceola views. Just two blocks from Park Avenue and adjacent to the Alfond Inn, this condominium lives like a private residence with unmatched access to boutique

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  106 S Interlachen Ave Unit 118, Winter Park, FL 32789
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  /2

  $520,000 Sold May 30, 2025

  2507 Lafayette Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 943 Sq Ft
  • Built 1956

  Last Sold Summary

  • 1% Below List Price
  • $551/SF
  • 41 Days On Market

  Current Estimated Value $539,322

  Last Listing Agent William Grim, III RE/MAX ASSURED

  2507 Lafayette Ave, Winter Park, FL 32789
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  /26

  Est $169,229 Not Listed For Sale

  2500 Lee Rd Unit 210, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft
  • Built 1969

  2500 Lee Rd Unit 210, Winter Park, FL 32789

  Last Sold Summary

  • $262/SF
  • 3 Days On Market

  • Last Sold Price $169,000
  • May 18, 2023

  Last Listing Agent Joyce Dowd FLORIDA REALTY INVESTMENTS
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  /36

  $1,050,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,342 Sq Ft

  632 Country Club Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards

  Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY

  632 Country Club Dr, Winter Park, FL 32789
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  /2

  $425,000 Sold Aug 21, 2025

  535 N Interlachen Ave Unit 205, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 986 Sq Ft
  • Built 1972

  Last Sold Summary

  • $431/SF
  • 0 Days On Market

  Current Estimated Value $422,036

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

  535 N Interlachen Ave Unit 205, Winter Park, FL 32789
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  /28

  Est $578,050 Not Listed For Sale

  102 S Interlachen Ave Unit 510, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 901 Sq Ft
  • Built 1971

  102 S Interlachen Ave Unit 510, Winter Park, FL 32789

  Last Sold Summary

  • 5% Above List Price
  • $610/SF
  • 2 Days On Market

  • Last Sold Price $550,000
  • Oct 27, 2023

  Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY
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  /27

  $700,000

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft

  865 S Pennsylvania Ave, Winter Park, FL 32789

  LOCATION, LOCATION, LOCATION...Desirable Winter Park "College Quarter" Historic District...Come take a tour of this wonderfully updated Bungalow with lots of windows for natural light, original hardwood floors, beautiful crown molding, and high ceilings. Did I mention the location, Walk to Park Ave, Rollins College, Hannibal Square, Mead Gardens, and Lake Virginia. Looking to "House Hack" then

  Jose Vega LPT REALTY, LLC

  865 S Pennsylvania Ave, Winter Park, FL 32789
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  /2

  $610,000 Sold Dec 18, 2025

  1620 Howell Branch Rd, Winter Park, FL 32789

  • 3 Beds
  • 4 Baths
  • 1,984 Sq Ft
  • Built 1985

  Last Sold Summary

  • 13% Below List Price
  • $307/SF
  • 97 Days On Market

  Current Estimated Value $638,471

  Last Listing Agent Michelle Rhea THE WILKINS WAY LLC

  1620 Howell Branch Rd, Winter Park, FL 32789
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  /2

  Est $1,525,253 Not Listed For Sale

  662 Osceola Ave Unit 203, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,290 Sq Ft
  • Built 2003

  662 Osceola Ave Unit 203, Winter Park, FL 32789

  Last Sold Summary

  • 9% Above List Price
  • $611/SF
  • 164 Days On Market

  • Last Sold Price $1,400,000
  • Jul 26, 2024

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY
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  /58

  $3,295,000 Pending

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

  700 Pinetree Rd, Winter Park, FL 32789

  Under contract-accepting backup offers. Located in the desirable heart of the Via's, this single story home with a transitional interior in Sicilian Shores is a meticulously renovated Winter Park charmer. Nestled quietly on an almost 1/2 acre corner lot, this beautiful home is walking distance to the Winter Park Racquet Club and easy proximity to Park Avenue and Interlachen Country Club. Complete

  Lauren Richardson FANNIE HILLMAN & ASSOCIATES

  700 Pinetree Rd, Winter Park, FL 32789
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  /2

  $1,860,000 Sold Mar 26, 2026

  1540 Palm Ave, Winter Park, FL 32789

  • 5 Beds
  • 3.5 Baths
  • 3,423 Sq Ft
  • Built 2014

  Last Sold Summary

  • 11% Below List Price
  • $543/SF
  • 158 Days On Market

  Current Estimated Value $1,933,944

  Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

  1540 Palm Ave, Winter Park, FL 32789
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  /2

  Est $200,240 Not Listed For Sale

  700 Melrose Ave Unit F2, Winter Park, FL 32789

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

  700 Melrose Ave Unit F2, Winter Park, FL 32789

  Last Sold Summary

  • 13% Below List Price
  • $315/SF
  • 193 Days On Market

  • Last Sold Price $230,000
  • Feb 21, 2025

  Last Listing Agent Carol van den Berg VAN DEN BERG REAL ESTATE GROUP
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  /25

  $2,999,500 Pending

  • 5 Beds
  • 5.5 Baths
  • 4,737 Sq Ft

  1229 Via Del Mar, Winter Park, FL 32789

  New construction by M. Lahr Homes, Orlando and Winter Park's premier custom home builder. This 5-bedroom, 5.5-bathroom home is situated on a 90' x 142' wide lot in the prestigious "Vias" neighborhood of Winter Park! The location is walking distance to the Winter Park Racquet Club and a short drive to Interlachen Country Club and Park Avenue. Don't miss an amazing opportunity to build a custom

  Erin Lahr CHARLES RUTENBERG REALTY ORLANDO

  1229 Via Del Mar, Winter Park, FL 32789
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  /2

  $385,000 Sold Jun 11, 2025

  1930 Albert Lee Pkwy, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,262 Sq Ft
  • Built 1955

  Last Sold Summary

  • 4% Below List Price
  • $305/SF
  • 101 Days On Market

  Current Estimated Value $380,600

  Last Listing Agent Carol van den Berg VAN DEN BERG REAL ESTATE GROUP

  1930 Albert Lee Pkwy, Winter Park, FL 32789
• 

  

  /27

  Est $347,879 Not Listed For Sale

  700 Melrose Ave Unit J32, Winter Park, FL 32789

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

  700 Melrose Ave Unit J32, Winter Park, FL 32789

  Last Sold Summary

  • 12% Below List Price
  • $368/SF
  • 0 Days On Market

  • Last Sold Price $395,000
  • May 24, 2024

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

Showing Results 361 - 400, Page 10 of 18