Homes in ZIP Code 32789

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  /27

  $124,900

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit E204, Winter Park, FL 32789

  Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom.

  Brandy Ray LOKATION

  1695 Lee Rd Unit E204, Winter Park, FL 32789
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  $250,000 Sold Mar 11, 2026

  2009 Cornell Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 762 Sq Ft
  • Built 1940

  Last Sold Summary

  • 7% Below List Price
  • $328/SF
  • 95 Days On Market

  Current Estimated Value $255,156

  Last Listing Agent Juliet Saldarriaga ORLANDO HOME DEALER LLC

  2009 Cornell Ave, Winter Park, FL 32789
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  /50

  Est $2,123,241 Not Listed For Sale

  270 E Lake Sue Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,151 Sq Ft
  • Built 2023

  270 E Lake Sue Ave, Winter Park, FL 32789

  Last Sold Summary

  • 12% Above List Price
  • $603/SF

  Last Sold Price $1,900,000

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
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  /55

  $495,000

  • 2 Beds
  • 2.5 Baths
  • 1,428 Sq Ft

  630 Killarney Bay Ct Unit 3, Winter Park, FL 32789

  Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath, with a convenient half

  Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

  630 Killarney Bay Ct Unit 3, Winter Park, FL 32789
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  /2

  $375,000 Sold Mar 06, 2026

  1007 Early Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft
  • Built 1956

  Last Sold Summary

  • 12% Below List Price
  • $218/SF
  • 101 Days On Market

  Current Estimated Value $380,832

  Last Listing Agent Eric Gross EXP REALTY LLC

  1007 Early Ave, Winter Park, FL 32789
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  /49

  Est $2,291,830 Not Listed For Sale

  180 Whipple Ave, Winter Park, FL 32789

  • 4 Beds
  • Built 2025

  180 Whipple Ave, Winter Park, FL 32789

  Last Sold Summary

  • 18% Above List Price
  • $383/SF
  • 353 Days On Market

  Last Sold Price $1,950,000

  Last Listing Agent Adam Cole COLEDEV REAL ESTATE LLC
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  /99

  $5,495,000

  • 5 Beds
  • 6.5 Baths
  • 7,278 Sq Ft

  2211 Azalea Place, Winter Park, FL 32789

  Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Park’s most prestigious neighborhoods—just moments from the exclusive Winter Park Racquet Club. This extraordinary residence offers the perfect blend of timeless architecture, refined finishes, and state-of-the-art updates, all

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  2211 Azalea Place, Winter Park, FL 32789
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  /2

  $434,000 Sold Sep 12, 2025

  1122 Washington Ave Unit 7, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,556 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Above List Price
  • $279/SF
  • 55 Days On Market

  Current Estimated Value $436,413

  Last Listing Agent Raul Veitia BELMONT REALTY

  1122 Washington Ave Unit 7, Winter Park, FL 32789
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  /17

  Not Listed For Sale

  700 Melrose Ave Unit K, Winter Park, FL 32789

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

  700 Melrose Ave Unit K, Winter Park, FL 32789

  Last Sold Summary

  • $350/SF
  • 188 Days On Market

  Last Sold Price $376,000

  Last Listing Agent Scott Butts KIMBRIDGE REALTY, LLC
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  /53

  $1,350,000

  • 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

  $850,000 Sold Mar 25, 2026

  465 N Phelps Ave, Winter Park, FL 32789

  • Land
  • 0.27 Acre
  • $3,148,148 per Acre

  Last Sold Summary

  • 7 Days On Market

  Current Estimated Value $1,017,024

  Last Listing Agent Hircanys Vicioso FIDICITY REALTY INC

  465 N Phelps Ave, Winter Park, FL 32789
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  /14

  Est $1,191,308 Not Listed For Sale

  514 W Swoope Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,585 Sq Ft
  • Built 2022

  514 W Swoope Ave, Winter Park, FL 32789

  Last Sold Summary

  • $460/SF
  • 52 Days On Market

  Last Sold Price $1,189,382

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC
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  /62

  $4,995,000 New Construction

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

  1302 Raintree Place, Winter Park, FL 32789

  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 glass, setting the tone for the artistry within. Inside, a European hotel–inspired

  Rikhil Amin FANNIE HILLMAN & ASSOCIATES

  1302 Raintree Place, Winter Park, FL 32789
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  /2

  $1,110,000 Sold Aug 26, 2025

  233 Hampden Place, Winter Park, FL 32789

  • 5 Beds
  • 3 Baths
  • 2,813 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $395/SF
  • 7 Days On Market

  Current Estimated Value $1,187,533

  Last Listing Agent Frank Ferrell FERRELL REALTY, INC.

  233 Hampden Place, Winter Park, FL 32789
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  /14

  Est $1,266,261 Not Listed For Sale

  516 W Swoope Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,666 Sq Ft
  • Built 2022

  516 W Swoope Ave, Winter Park, FL 32789

  Last Sold Summary

  • 7% Above List Price
  • $446/SF
  • 67 Days On Market

  Last Sold Price $1,188,432

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC
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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

  $3,200,000 Sold Nov 04, 2025

  1900 W Fawsett Rd, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,600 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $696/SF
  • 6 Days On Market

  Current Estimated Value $3,178,851

  Last Listing Agent Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

  1900 W Fawsett Rd, Winter Park, FL 32789
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  /14

  Est $1,226,052 Not Listed For Sale

  502 W Swoope Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,585 Sq Ft
  • Built 2021

  502 W Swoope Ave, Winter Park, FL 32789

  Last Sold Summary

  • 17% Above List Price
  • $406/SF
  • 0 Days On Market

  Last Sold Price $1,050,000

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC
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  /6

  $795,000 Pending

  • Land
  • 0.22 Acre
  • $3,613,636 per Acre

  325 N Phelps Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. 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

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

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

  $879,000 Sold Nov 14, 2025

  451 Fairfax Ave, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,227 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $395/SF
  • 5 Days On Market

  Current Estimated Value $864,888

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

  451 Fairfax Ave, Winter Park, FL 32789
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  /2

  Est $797,619 Not Listed For Sale

  1820 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,252 Sq Ft
  • Built 2018

  1820 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 4% Below List Price
  • $371/SF
  • 81 Days On Market

  Last Sold Price $835,000

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY
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  /4

  $2,395,000 Open Thu 4PM - 6PM

  • 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

  $630,000 Sold Aug 11, 2025

  1792 Killarney Dr, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,264 Sq Ft
  • Built 1958

  Last Sold Summary

  • 3% Below List Price
  • $278/SF
  • 1 Day On Market

  Current Estimated Value $652,518

  Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

  1792 Killarney Dr, Winter Park, FL 32789
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  /77

  Est $1,263,345 Not Listed For Sale

  690 Osceola Ave Unit 504, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,079 Sq Ft
  • Built 1969

  690 Osceola Ave Unit 504, Winter Park, FL 32789

  Last Sold Summary

  • 8% Above List Price
  • $565/SF
  • 74 Days On Market

  Last Sold Price $1,175,000

  Last Listing Agent Dela Armstrong C BRENNER INC
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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

  $755,000 Sold Jul 18, 2025

  1000 Howell Branch Rd, Winter Park, FL 32789

  • Land
  • 0.55 Acre
  • $1,372,727 per Acre

  Last Sold Summary

  • 30% Below List Price
  • 241 Days On Market

  Current Estimated Value $817,704

  Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

  1000 Howell Branch Rd, Winter Park, FL 32789
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  /47

  Est $1,327,035 Not Listed For Sale

  518 W Swoope Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,734 Sq Ft
  • Built 2021

  518 W Swoope Ave, Winter Park, FL 32789

  Last Sold Summary

  • 9% Below List Price
  • $535/SF
  • 119 Days On Market

  Last Sold Price $1,464,000

  Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK
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  /53

  $2,350,000

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

  2503 Versailles Ave, Winter Park, FL 32789

  BUYER BACKED OUT IS NOW YOUR OPPORTUNITY! This property is now priced under appraised value with new carpet, paint and landscaping. Beautifully updated and offered for the first time, this 2015 David Weekley home sits on a rare cul-de-sac in the heart of Winter Park, zoned for Dommerich Elementary and Winter Park schools. This 5-bedroom, 5-bath home features an office, large bonus room, covered

  Sarah Tomlinson COMPASS FLORIDA LLC

  2503 Versailles Ave, Winter Park, FL 32789
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  /2

  $3,845,000 Sold May 16, 2025

  2020 Venetian Way, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 4,188 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $918/SF
  • 4 Days On Market

  Current Estimated Value $3,932,407

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

  2020 Venetian Way, Winter Park, FL 32789
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  Not Listed For Sale

  512 W Swoope Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,585 Sq Ft
  • Built 2021

  512 W Swoope Ave, Winter Park, FL 32789

  Last Sold Summary

  • $422/SF
  • 86 Days On Market

  Last Sold Price $1,089,925

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC
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  /57

  $2,900,000 Pending

  • 3 Beds
  • 7 Baths
  • 5,483 Sq Ft

  1401 Green Cove Rd, Winter Park, FL 32789

  Under contract-accepting backup offers. Set across Lake Maitland on a street where every home is an architectural gem, this Award-winning Villa Toscana blends Old-World craftsmanship with timeless architectural elegance in one of Winter Park’s most coveted enclaves. Built in 2009 and named “Best of Show” in the Parade of Homes, this 5,483 sq ft estate offers 3 bedrooms, 7 bathrooms, and 7

  Adriana Oyarce ANCHOR REAL ESTATE

  1401 Green Cove Rd, Winter Park, FL 32789
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  /2

  $975,000 Sold Feb 10, 2026

  1150 Kenwood Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,557 Sq Ft
  • Built 1988

  Last Sold Summary

  • 24% Below List Price
  • $381/SF
  • 97 Days On Market

  Current Estimated Value $1,142,505

  Last Listing Agent JJ Mackle PREMIER SOTHEBY'S INTL. REALTY

  1150 Kenwood Ave, Winter Park, FL 32789
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  /13

  Est $1,222,095 Not Listed For Sale

  500 W Swoope Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,666 Sq Ft
  • Built 2021

  500 W Swoope Ave, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $455/SF
  • 85 Days On Market

  Last Sold Price $1,212,835

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC
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  /60

  $2,295,000

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

  2299 Via Tuscany, Winter Park, FL 32789

  Welcome to 2299 Via Tuscany, a remarkable 4-bedroom, 3.5 bathroom residence in the prestigious Winter Park Vias. This 3,986 square foot home, set on a .40-acre private lot, offers a blend of luxury and comfort. The property has seen recent updates in the kitchen and bathrooms and features a new architectural shingle roof (2023), Pebble-tech style pool finish and a manicured landscape. Inside,

  Vincent Scarlatos CORCORAN PREMIER REALTY

  2299 Via Tuscany, Winter Park, FL 32789
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  /2

  $475,000 Sold Feb 02, 2026

  1740 Anzle Ave, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft
  • Built 1956

  Last Sold Summary

  • 40% Below List Price
  • $263/SF
  • 109 Days On Market

  Current Estimated Value $570,660

  Last Listing Agent Freddy DeCoster GOYAL & DECOSTER REALTY

  1740 Anzle Ave, Winter Park, FL 32789
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  Est $2,399,224 Not Listed For Sale

  170 S Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,288 Sq Ft
  • Built 2023

  170 S Phelps Ave, Winter Park, FL 32789

  Last Sold Summary

  • 2% Above List Price
  • $548/SF
  • 236 Days On Market

  Last Sold Price $2,350,000

  Last Listing Agent Monica Tipirneni FOLIO REALTY LLC
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  /5

  $4,595,000

  • Land
  • 0.35 Acre
  • $13,128,571 per Acre

  1336 College Point, Winter Park, FL 32789

  A rare offering on the shores of Lake Virginia, this prime lakefront parcel presents a distinguished opportunity within Winter Park’s most coveted waterfront corridor. Encompassing a significant Lake Virginia homesite on the Winter Park Chain of Lakes, the site currently includes a 1926 structure that may be preserved, redesigned or removed to accommodate a custom waterfront residence. Positioned

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1336 College Point, Winter Park, FL 32789
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  /2

  $325,000 Sold Oct 03, 2025

  260 Killarney Bay Ct Unit 6, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Below List Price
  • $285/SF
  • 0 Days On Market

  Current Estimated Value $324,067

  Last Listing Agent Tyler Gibson LPT REALTY, LLC

  260 Killarney Bay Ct Unit 6, Winter Park, FL 32789
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  /2

  Est $1,446,523 Not Listed For Sale

  1009 S Pennsylvania Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,023 Sq Ft
  • Built 2016

  1009 S Pennsylvania Ave, Winter Park, FL 32789

  Last Sold Summary

  • 8% Below List Price
  • $521/SF
  • 5 Days On Market

  Last Sold Price $1,575,000

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY
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  /46

  $2,995,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,686 Sq Ft

  611 Williams Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Artistry and exquisite style are brilliantly showcased in this renovated Winter Park masterpiece. Located in the coveted neighborhood of Park Grove, this magical home is sure to take your breath away, with stunning surprises around every corner. Since 2022, the home has undergone an extraordinary transformation in thoughtful renovations, upgrades, and

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  611 Williams Dr, Winter Park, FL 32789

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