Homes in ZIP Code 32789

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  /2

  Est $1,517,807 Not Listed For Sale

  1571 Sunset Dr, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 2,700 Sq Ft
  • Built 2015

  1571 Sunset Dr, Winter Park, FL 32789

  Last Sold Summary

  • 5% Above List Price
  • $536/SF
  • 79 Days On Market

  • Last Sold Price $1,446,000
  • Nov 04, 2024

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY
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  $1,950,000

  • 3 Beds
  • 2 Baths
  • 1,807 Sq Ft

  106 S Interlachen Ave Unit 518, Winter Park, FL 32789

  Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to original framework and meticulously rebuilt with elevated design and superior finishes throughout. The result is an expansive openness illuminated with natural light and accented by European oak wide-plank flooring, Level 5 smooth-finish walls and ceilings, architectural

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  106 S Interlachen Ave Unit 518, Winter Park, FL 32789
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  /2

  $1,850,000 Sold Dec 15, 2025

  419 W Morse Blvd, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,027 Sq Ft
  • Built 2018

  Last Sold Summary

  • 5% Below List Price
  • $611/SF
  • 0 Days On Market

  Current Estimated Value $1,860,758

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

  419 W Morse Blvd, Winter Park, FL 32789
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  /2

  Est $2,259,952 Not Listed For Sale

  1770 Oakhurst Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,640 Sq Ft
  • Built 2019

  1770 Oakhurst Ave, Winter Park, FL 32789

  Last Sold Summary

  • $618/SF
  • 20 Days On Market

  • Last Sold Price $2,250,000
  • Jul 29, 2024

  Last Listing Agent Nadia Moayeri PALMANO GROUP RE BROKERAGE LLC
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  /53

  $1,299,000

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

  100 S Interlachen Ave Unit 101, Winter Park, FL 32789

  On the first floor within The Cloisters, this three-bedroom, two-bath residence offers 1,734 square feet of renovated living space in one of Winter Park’s accessible lakefront communities. An oversized tiled patio, partially covered and ideal for outdoor dining or morning coffee, extends the living space and enhances everyday functionality. Renovated in 2021 by Charles Clayton Construction, an

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 101, Winter Park, FL 32789
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  /2

  $280,000 Sold Jun 27, 2025

  2446 Lotafun Ave, Winter Park, FL 32789

  • Land
  • 7,405 Sq Ft
  • $1,647,059 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 123 Days On Market

  Current Estimated Value $284,333

  Last Listing Agent David Francetic COLDWELL BANKER REALTY

  2446 Lotafun Ave, Winter Park, FL 32789
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  /2

  Est $1,169,013 Not Listed For Sale

  1571 Oneco Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,510 Sq Ft
  • Built 2009

  1571 Oneco Ave, Winter Park, FL 32789

  Last Sold Summary

  • 4% Above List Price
  • $450/SF
  • 41 Days On Market

  • Last Sold Price $1,129,000
  • Jan 31, 2025

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC
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  /62

  $4,995,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 4,738 Sq Ft

  1302 Raintree Place, Winter Park, FL 32789

  Under contract-accepting backup offers. *Under Contract - Accepting Backup Offers* An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy

  Rikhil Amin FANNIE HILLMAN & ASSOCIATES

  1302 Raintree Place, Winter Park, FL 32789
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  /2

  $3,800,000 Sold Feb 24, 2026

  637 N Park Ave, Winter Park, FL 32789

  • 3 Beds
  • 5 Baths
  • 4,237 Sq Ft
  • Built 2019

  Last Sold Summary

  • 2% Below List Price
  • $897/SF
  • 24 Days On Market

  Current Estimated Value $3,476,043

  Last Listing Agent Whitney Johnson COLDWELL BANKER REALTY

  637 N Park Ave, Winter Park, FL 32789
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  /29

  Est $605,433 Not Listed For Sale

  1400 Indiana Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,054 Sq Ft
  • Built 2008

  1400 Indiana Ave, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $292/SF
  • 1 Day On Market

  • Last Sold Price $600,000
  • Jul 10, 2023

  Last Listing Agent Shirley Jones COLDWELL BANKER REALTY
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  /29

  $415,000

  • 3 Beds
  • 2 Baths
  • 1,197 Sq Ft

  1518 Pinewood Dr, Winter Park, FL 32789

  Income-producing home with a detached in-law apartment in a prime central Orlando location — ideal for a house hack, long-term rental, or short-term rental (Airbnb allowed). The main house is a two-bedroom, one-bath residence, while the in-law apartment is a completely detached one-bedroom, one-bath unit with separate entrances and separate mailboxes, offering excellent privacy and flexibility.

  Dan Grieb KELLER WILLIAMS REALTY AT THE PARKS

  1518 Pinewood Dr, Winter Park, FL 32789
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  /2

  $5,400,000 Sold Jul 14, 2025

  541 Virginia Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 4,725 Sq Ft
  • Built 2008

  Last Sold Summary

  • 14% Below List Price
  • $1,143/SF
  • 152 Days On Market

  Current Estimated Value $5,253,998

  Last Listing Agent Keith Moore HOMEVEST REALTY

  541 Virginia Dr, Winter Park, FL 32789
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  /59

  Est $2,282,890 Not Listed For Sale

  1411 Elizabeth Dr, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,870 Sq Ft
  • Built 2008

  1411 Elizabeth Dr, Winter Park, FL 32789

  Last Sold Summary

  • 12% Below List Price
  • $669/SF
  • 26 Days On Market

  • Last Sold Price $2,590,000
  • Jul 28, 2023

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC
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  /6

  $795,000

  • Land
  • 9,583 Sq Ft
  • $3,613,636 per Acre

  325 N Phelps Ave, Winter Park, FL 32789

  Fantastic lot opportunity to build in one of Winter Park’s prime neighborhoods. Bring your vision and your builder to design a home tailored to your lifestyle on this 64-by-150-foot lot. The property includes a two-bedroom, one-bath single-family home with approximately 1,400 square feet of living space, making it an ideal potential income-producing property while you finalize your plans. Whether

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  325 N Phelps Ave, Winter Park, FL 32789
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  /2

  $1,305,000 Sold Nov 05, 2025

  1600 Barcelona Way, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,014 Sq Ft
  • Built 1972

  Last Sold Summary

  • 12% Below List Price
  • $433/SF
  • 175 Days On Market

  Current Estimated Value $1,356,039

  Last Listing Agent Laura Ascenso CREEGAN GROUP

  1600 Barcelona Way, Winter Park, FL 32789
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  /2

  Est $440,061 Not Listed For Sale

  2112 Staunton Ave, Winter Park, FL 32789

  • 3 Beds
  • 1 Bath
  • 1,438 Sq Ft
  • Built 1954

  2112 Staunton Ave, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $312/SF
  • 12 Days On Market

  • Last Sold Price $449,000
  • Jan 30, 2025

  Last Listing Agent Stacey Payne PREFERRED REAL ESTATE BROKERS
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  $2,394,500 New Construction

  • 5 Beds
  • 6.5 Baths
  • 4,506 Sq Ft

  2412 Chantilly Ave, Winter Park, FL 32789

  Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This

  Tab Bish LLC REAL BROKER, LLC

  2412 Chantilly Ave, Winter Park, FL 32789
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  /2

  $1,500,000 Sold Mar 16, 2026

  1871 Taylor Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,401 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $441/SF
  • 2 Days On Market

  Current Estimated Value $1,682,199

  Last Listing Agent Laura Earl CORCORAN PREMIER REALTY

  1871 Taylor Ave, Winter Park, FL 32789
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  /2

  Est $1,948,599 Not Listed For Sale

  331 E Reading Way, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,361 Sq Ft
  • Built 2007

  331 E Reading Way, Winter Park, FL 32789

  Last Sold Summary

  • 13% Above List Price
  • $513/SF
  • 110 Days On Market

  • Last Sold Price $1,725,000
  • Oct 15, 2024

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY
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  $599,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,556 Sq Ft

  1951 Staunton Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. TRANSFERABLE TERMITE BOND INCLUDED. Welcome home to the charm and character of the bygone days. This 3-bedroom, 2-bathroom home offers 2,556 square feet, with the historic main home originally built in 1922. Featuring original antique wood floors, a classic fireplace, and a one of a kind upstairs loft, there's nothing quite like it! A charming front porch

  Veronica Figueroa EXP REALTY LLC

  1951 Staunton Ave, Winter Park, FL 32789
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  /2

  $995,000 Sold Jul 22, 2025

  1821 Windsor Dr, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,188 Sq Ft
  • Built 2017

  Last Sold Summary

  • 10% Below List Price
  • $455/SF
  • 25 Days On Market

  Current Estimated Value $1,026,677

  Last Listing Agent Chris Creegan CREEGAN GROUP

  1821 Windsor Dr, Winter Park, FL 32789
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  /27

  Est $1,002,202 Not Listed For Sale

  2529 Modac Trail, Winter Park, FL 32789

  • 5 Beds
  • 3 Baths
  • 3,043 Sq Ft
  • Built 1966

  2529 Modac Trail, Winter Park, FL 32789

  Last Sold Summary

  • 5% Above List Price
  • $312/SF
  • 17 Days On Market

  • Last Sold Price $949,999
  • Jun 15, 2023

  Last Listing Agent Erin Rue PALMER SCOTT PROPERTIES LLC
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  /17

  $6,950,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,905 Sq Ft

  40 Palmer Ave, Winter Park, FL 32789

  Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer represents a rare convergence of architectural significance, uncompromising craftsmanship, and premier Winter Park location. Built by Vimaro Homes, this extraordinary new construction estate is a statement piece that redefines what

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  40 Palmer Ave, Winter Park, FL 32789
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  /2

  $750,000 Sold Oct 02, 2025

  100 S Interlachen Ave Unit 203D, Winter Park, FL 32789

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

  Last Sold Summary

  • 3% Below List Price
  • $592/SF
  • 0 Days On Market

  Last Listing Agent Michael Ford FANNIE HILLMAN & ASSOCIATES

  100 S Interlachen Ave Unit 203D, Winter Park, FL 32789
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  /23

  Est $1,097,400 Not Listed For Sale

  1600 Alabama Dr Unit 201, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 1921

  1600 Alabama Dr Unit 201, Winter Park, FL 32789

  Last Sold Summary

  • 22% Above List Price
  • $465/SF
  • 101 Days On Market

  • Last Sold Price $900,000
  • Jul 24, 2023

  Last Listing Agent Lauren Richardson FANNIE HILLMAN & ASSOCIATES
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  /53

  $2,184,000 Pending

  • 5 Beds
  • 4 Baths
  • 4,026 Sq Ft

  2503 Versailles Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Back on the market—an exceptional opportunity in Winter Park. Now offered below appraised value, this residence has been thoughtfully refreshed with new carpet, interior paint, and thoughtful enhancements.Presented for the first time, this beautifully appointed 2014 David Weekley home is tucked away on a large corner lot within a rare cul-de-sac in the

  Sarah Tomlinson COMPASS FLORIDA LLC

  2503 Versailles Ave, Winter Park, FL 32789
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  /2

  $1,300,000 Sold Oct 02, 2025

  857 Brock St, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,288 Sq Ft
  • Built 1964

  Last Sold Summary

  • $568/SF
  • 0 Days On Market

  Current Estimated Value $1,261,823

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  857 Brock St, Winter Park, FL 32789
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  /29

  Est $891,140 Not Listed For Sale

  1602 Alabama Dr Unit 107, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 993 Sq Ft
  • Built 1921

  1602 Alabama Dr Unit 107, Winter Park, FL 32789

  Last Sold Summary

  • 11% Below List Price
  • $1,007/SF
  • 7 Days On Market

  • Last Sold Price $1,000,000
  • Dec 19, 2023

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY
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  $349,000

  • 2 Beds
  • 1 Bath
  • 749 Sq Ft

  811 Overspin Dr, Winter Park, FL 32789

  Charming Winter Park Opportunity in Desirable Dubsdread Heights! NEW ROOF NEW A/c new kitchen ,bath, floor Welcome to 811 Overspin Drive, a cozy and character-filled 2-bedroom, 1-bath single-family home nestled in the heart of Winter Park. This property offers approximately 700+ square feet of living space on a generously sized lot, providing endless potential for homeowners, investors, or those

  Rickey Singh RICK SINGH REAL ESTATE

  811 Overspin Dr, Winter Park, FL 32789
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  /2

  $1,587,500 Sold Jul 31, 2025

  279 Rippling Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,472 Sq Ft
  • Built 1961

  Last Sold Summary

  • 12% Below List Price
  • $457/SF
  • 318 Days On Market

  Current Estimated Value $1,594,198

  Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

  279 Rippling Ln, Winter Park, FL 32789
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  /2

  Est $9,023,327 Not Listed For Sale

  2001 Bett Mar Ln, Winter Park, FL 32789

  • 8 Beds
  • 8.5 Baths
  • 8,583 Sq Ft
  • Built 1995

  2001 Bett Mar Ln, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $1,037/SF
  • 1 Day On Market

  • Last Sold Price $8,900,000
  • May 02, 2025

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY
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  $2,200,000

  • 4 Beds
  • 3.5 Baths
  • 3,986 Sq Ft

  2299 Via Tuscany, Winter Park, FL 32789

  Picture yourself unwinding in your private 0.41-acre yard, taking a dip in the pool, flipping through a good book, or hosting friends on a sunny afternoon. From there, stroll over to the Winter Park Racquet Club for tennis, pickleball, or lunch (kids are covered—there’s a sidewalk the whole way), or head to the deeded lake access launch for a day of kayaking on the Winter Park Chain of Lakes.

  Vincent Scarlatos CORCORAN PREMIER REALTY

  2299 Via Tuscany, Winter Park, FL 32789
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  /2

  $13,000,000 Sold Feb 24, 2026

  2203 Via Tuscany, Winter Park, FL 32789

  • 6 Beds
  • 9 Baths
  • 12,190 Sq Ft
  • Built 2002

  Last Sold Summary

  • 1% Above List Price
  • $1,066/SF
  • 4 Days On Market

  Current Estimated Value $9,621,387

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

  2203 Via Tuscany, Winter Park, FL 32789
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  /2

  Est $205,516 Not Listed For Sale

  851 Miles Ave Unit 26, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Built 1984

  851 Miles Ave Unit 26, Winter Park, FL 32789

  Last Sold Summary

  • 6% Below List Price
  • $271/SF
  • 14 Days On Market

  • Last Sold Price $219,000
  • Sep 04, 2024

  Last Listing Agent Kevin Mendoza CALL IT CLOSED INTL REALTY
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  /25

  $550,000

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  1807 Hammerlin Ave Unit G, Winter Park, FL 32789

  **Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle, convenience, and

  Courtney Dietch ALL REAL ESTATE & INVESTMENTS

  1807 Hammerlin Ave Unit G, Winter Park, FL 32789
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  /2

  $2,155,000 Sold Aug 23, 2025

  2915 Parkland Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,356 Sq Ft
  • Built 2025

  Last Sold Summary

  • $642/SF

  Current Estimated Value $1,991,091

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

  2915 Parkland Dr, Winter Park, FL 32789
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  /16

  Est $216,657 Not Listed For Sale

  851 Miles Ave Unit 28, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Built 1984

  851 Miles Ave Unit 28, Winter Park, FL 32789

  Last Sold Summary

  • 9% Below List Price
  • $296/SF
  • 43 Days On Market

  • Last Sold Price $239,000
  • Sep 15, 2023

  Last Listing Agent Tom Graves FUN HOMES
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  /34

  $490,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,378 Sq Ft

  958 Hanover Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Mother-in-Law suit attached with private entrance on a dead-end street with water view. Welcome to this beautifully remodeled home in the heart of Winter Park, offering the perfect blend of charm, privacy, and convenience. Situated at the end of a quiet street, this unique property provides exceptional privacy while showcasing peaceful views of nearby Lake

  Christopher Lyons AGILE GROUP REALTY

  958 Hanover Ave, Winter Park, FL 32789
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  /2

  $1,607,160 Sold Aug 01, 2025

  1541 Chestnut Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,840 Sq Ft
  • Built 2018

  Last Sold Summary

  • 4% Above List Price
  • $566/SF
  • 2 Days On Market

  Current Estimated Value $1,580,564

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1541 Chestnut Ave, Winter Park, FL 32789
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  /2

  Est $192,133 Not Listed For Sale

  851 Miles Ave Unit 4, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Built 1984

  851 Miles Ave Unit 4, Winter Park, FL 32789

  Last Sold Summary

  • 2% Above List Price
  • $234/SF
  • 218 Days On Market

  • Last Sold Price $188,700
  • Nov 18, 2024

  Last Listing Agent Lenny Migliaccio RE/MAX

Showing Results 281 - 320, Page 8 of 18