Homes in ZIP Code 32789

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  $810,000 Sold Nov 26, 2025

  1314 Canterbury Rd, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,738 Sq Ft
  • Built 1950

  Last Sold Summary

  • $466/SF

  Current Estimated Value $785,122

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

  1314 Canterbury Rd, Winter Park, FL 32789
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  Not Listed For Sale

  1695 Lee Rd Unit D206, Winter Park, FL 32789

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

  1695 Lee Rd Unit D206, Winter Park, FL 32789

  Last Sold Summary

  • $165/SF
  • 271 Days On Market

  • Last Sold Price $145,000
  • May 02, 2025

  Last Listing Agent Justin Adams EXP REALTY LLC
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  /41

  $1,989,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 2,964 Sq Ft

  785 N Phelps Ave, Winter Park, FL 32789

  Exquisite new construction in the heart of Winter Park, this LUIH Luxury Homes residence distinguishes itself through refined design, thoughtful efficiency, and an elevated level of craftsmanship. From the moment you enter, the home reveals itself with deliberate intention, clean architectural lines and a light-filled, open-concept layout create an effortless flow throughout. The main living

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  785 N Phelps Ave, Winter Park, FL 32789
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  $2,495,000 Sold Jul 21, 2025

  1690 Palm Ave, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 3,967 Sq Ft
  • Built 2020

  Last Sold Summary

  • 12% Below List Price
  • $629/SF
  • 56 Days On Market

  Current Estimated Value $2,515,895

  Last Listing Agent Daniel Robinson HOUWZER INC

  1690 Palm Ave, Winter Park, FL 32789
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  Not Listed For Sale

  1695 Lee Rd Unit D205, Winter Park, FL 32789

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

  1695 Lee Rd Unit D205, Winter Park, FL 32789

  Last Sold Summary

  • $159/SF
  • 11 Days On Market

  • Last Sold Price $140,000
  • Aug 08, 2024

  Last Listing Agent Martha Grasty EXP REALTY LLC
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  /24

  $209,999 Pending

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft

  851 Miles Ave Unit 13, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor condo in the heart of charming Winter Park, FL 32789! Meticulously updated since 2023, this home blends modern luxury with effortless comfort and is truly move-in ready.As you step inside, you’ll be greeted by elegant porcelain tile flooring throughout—offering both

  Eric Campbell LPT REALTY, LLC

  851 Miles Ave Unit 13, Winter Park, FL 32789
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  $1,075,000 Sold Jul 31, 2025

  1690 Oneco Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,703 Sq Ft
  • Built 1967

  Last Sold Summary

  • 10% Below List Price
  • $398/SF
  • 140 Days On Market

  Current Estimated Value $1,114,234

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

  1690 Oneco Ave, Winter Park, FL 32789
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  /18

  Not Listed For Sale

  1695 Lee Rd Unit D202, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Built 1966

  1695 Lee Rd Unit D202, Winter Park, FL 32789

  Last Sold Summary

  • $177/SF
  • 15 Days On Market

  • Last Sold Price $203,000
  • May 26, 2023

  Last Listing Agent Mike Giordano COLDWELL BANKER REALTY
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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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  $1,129,000 Sold Dec 10, 2025

  100 S Virginia Ave Unit 314, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,615 Sq Ft
  • Built 2009

  Last Sold Summary

  • $432/SF
  • 4 Days On Market

  Current Estimated Value $1,126,567

  Last Listing Agent Julieta Knapp ACCUMARK PROPERTIES

  100 S Virginia Ave Unit 314, Winter Park, FL 32789
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  /31

  Not Listed For Sale

  1695 Lee Rd Unit C203, Winter Park, FL 32789

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

  1695 Lee Rd Unit C203, Winter Park, FL 32789

  Last Sold Summary

  • $179/SF
  • 4 Days On Market

  • Last Sold Price $158,000
  • Jun 28, 2023

  Last Listing Agent Zac Hernandez EMPIRE NETWORK REALTY
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  $1,599,000

  • 4 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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  $702,050 Sold Jan 23, 2026

  300 Carolina Ave Unit 201, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • Built 1981

  Last Sold Summary

  • 5% Below List Price
  • $538/SF
  • 19 Days On Market

  Last Listing Agent Teri Webster LPT REALTY, LLC

  300 Carolina Ave Unit 201, Winter Park, FL 32789
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  Not Listed For Sale

  1695 Lee Rd Unit D109, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 638 Sq Ft
  • Built 1966

  1695 Lee Rd Unit D109, Winter Park, FL 32789

  Last Sold Summary

  • $219/SF
  • 0 Days On Market

  • Last Sold Price $140,000
  • Jan 31, 2024

  Last Listing Agent Erin Baker FANNIE HILLMAN & ASSOCIATES
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  $325,000

  • 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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  $610,000 Sold Aug 11, 2025

  843 W Swoope Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1962

  Last Sold Summary

  • 10% Below List Price
  • $495/SF
  • 67 Days On Market

  Current Estimated Value $586,945

  Last Listing Agent Jean Chalifour COLDWELL BANKER REALTY

  843 W Swoope Ave, Winter Park, FL 32789
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  Not Listed For Sale

  1695 Lee Rd Unit A115, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Built 1966

  1695 Lee Rd Unit A115, Winter Park, FL 32789

  Last Sold Summary

  • $196/SF
  • 167 Days On Market

  • Last Sold Price $225,000
  • Apr 30, 2024

  Last Listing Agent Justin Adams EXP REALTY LLC
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  $4,500,000

  • Land
  • 20,908 Sq Ft
  • $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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  $1,770,000 Sold Sep 22, 2025

  690 Williams Dr, Winter Park, FL 32789

  • 3 Beds
  • 4 Baths
  • 3,121 Sq Ft
  • Built 1962

  Last Sold Summary

  • 2% Below List Price
  • $567/SF
  • 0 Days On Market

  Current Estimated Value $1,761,863

  Last Listing Agent Tiffany Grindstaff KELLY PRICE & COMPANY LLC

  690 Williams Dr, Winter Park, FL 32789
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  Not Listed For Sale

  1500 Gay Rd Unit 8B, Winter Park, FL 32789

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

  1500 Gay Rd Unit 8B, Winter Park, FL 32789

  Last Sold Summary

  • $234/SF
  • 16 Days On Market

  • Last Sold Price $240,000
  • Aug 16, 2024

  Last Listing Agent Marci Blanchard KELLER WILLIAMS ADVANTAGE REALTY
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  $1,640,000

  • 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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  $2,440,000 Sold Jul 01, 2025

  1700 Palm Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,770 Sq Ft
  • Built 2016

  Last Sold Summary

  • 8% Below List Price
  • $647/SF
  • 41 Days On Market

  Current Estimated Value $2,438,265

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1700 Palm Ave, Winter Park, FL 32789
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  Est $1,834,959 Not Listed For Sale

  1764 Elizabeths Walk, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 3,989 Sq Ft
  • Built 2012

  1764 Elizabeths Walk, Winter Park, FL 32789

  Last Sold Summary

  • 8% Above List Price
  • $426/SF
  • 159 Days On Market

  • Last Sold Price $1,700,000
  • Feb 26, 2025

  Last Listing Agent Matt McKee COMPASS FLORIDA LLC
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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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  $1,688,750 Sold Apr 01, 2026

  1705 Elizabeths Walk, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 3,820 Sq Ft
  • Built 2005

  Last Sold Summary

  • 2% Above List Price
  • $442/SF
  • 3 Days On Market

  Current Estimated Value $2,002,870

  Last Listing Agent Keith Moore HOMEVEST REALTY

  1705 Elizabeths Walk, Winter Park, FL 32789
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  Est $266,124 Not Listed For Sale

  287 Sandlewood Trail Unit 4, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft
  • Built 1984

  287 Sandlewood Trail Unit 4, Winter Park, FL 32789

  Last Sold Summary

  • 7% Below List Price
  • $297/SF
  • 182 Days On Market

  • Last Sold Price $285,000
  • Aug 24, 2023

  Last Listing Agent A.V. Blalock COLDWELL BANKER REALTY
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  $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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  $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 $1,029,004

  Last Listing Agent Jennifer Roberts FLORIDA EXECUTIVE REALTY

  1802 Arbor Park Dr, Winter Park, FL 32789
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  Est $274,381 Not Listed For Sale

  215 Sandlewood Trail Unit 7, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft
  • Built 1986

  215 Sandlewood Trail Unit 7, Winter Park, FL 32789

  Last Sold Summary

  • 9% Below List Price
  • $312/SF
  • 5 Days On Market

  • Last Sold Price $300,000
  • May 28, 2024

  Last Listing Agent Pam Grabenhorst THE WILKINS WAY LLC
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  $1,249,000

  • 4 Beds
  • 3 Baths
  • 2,871 Sq Ft

  363 N Phelps Ave, Winter Park, FL 32789

  This light and bright, single-story, almost 3,000 square foot pool home features a split plan with four full bedrooms and three full baths. Your guests will immediately appreciate the expansive paver driveway, which allows easy, off-street parking. Once inside, they will admire the abundance of natural light provided by the new, large-format windows. Not only do the new windows (2022) illuminate

  Chris Creegan CREEGAN GROUP

  363 N Phelps Ave, Winter Park, FL 32789
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  $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 $470,047

  Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

  2381 Roxbury Rd, Winter Park, FL 32789
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  Est $284,693 Not Listed For Sale

  311 Sandlewood Trail Unit 4, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 980 Sq Ft
  • Built 1984

  311 Sandlewood Trail Unit 4, Winter Park, FL 32789

  Last Sold Summary

  • 7% Below List Price
  • $311/SF
  • 5 Days On Market

  • Last Sold Price $305,000
  • Feb 25, 2025

  Last Listing Agent Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY
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  $4,285,000

  • 4 Beds
  • 5.5 Baths
  • 4,066 Sq Ft

  1441 Cardinal Ct, Winter Park, FL 32789

  Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet cul-de-sac in the heart of Winter Park. Designed with a modern, timeless style, it offers luxury finishes paired with a warm, comfortable feel. The home features 4,060 square feet, including four en-suite bedrooms, five full bathrooms, a powder bath, and a bonus room with a built-in office. The spacious

  Damian Bergler CHARLES RUTENBERG REALTY ORLANDO

  1441 Cardinal Ct, Winter Park, FL 32789
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  $1,942,000 Sold Jul 14, 2025

  1394 Stewart St, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 3,907 Sq Ft
  • Built 1961

  Last Sold Summary

  • 12% Below List Price
  • $497/SF
  • 50 Days On Market

  Current Estimated Value $1,913,911

  Last Listing Agent Richard Vaughn REALTY ONE GROUP INSPIRATION

  1394 Stewart St, Winter Park, FL 32789
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  /23

  Est $467,658 Not Listed For Sale

  1769 Indiana Ave Unit D, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,616 Sq Ft
  • Built 2008

  1769 Indiana Ave Unit D, Winter Park, FL 32789

  Last Sold Summary

  • 11% Above List Price
  • $260/SF
  • 20 Days On Market

  • Last Sold Price $420,000
  • Jun 12, 2023

  Last Listing Agent Eduardo Dieter SPACE GROUP REALTY LLC
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  $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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  $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 $548,679

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  1817 Jessica Ct, Winter Park, FL 32789
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  Est $336,457 Not Listed For Sale

  2038 Jewell Ave, Winter Park, FL 32789

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

  2038 Jewell Ave, Winter Park, FL 32789

  Last Sold Summary

  • 2% Above List Price
  • $408/SF
  • 4 Days On Market

  • Last Sold Price $330,000
  • Jul 05, 2023

  Last Listing Agent Alexandra Pillat RE/MAX
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  $489,000

  • Land
  • 9,147 Sq Ft
  • $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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  $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 $932,521

  Last Listing Agent Ruth Harris COLDWELL BANKER REALTY

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

Showing Results 561 - 600, Page 15 of 18