Winter Park, FL Homes

• 

  

  

  /24

  $390,000

  • 3 Beds
  • 2 Baths
  • 1,220 Sq Ft

  5110 N Woodcrest Dr, Winter Park, FL 32792

  Discover the perfect blend of comfort and convenience in this beautifully remodeled 3-bedroom, 2-bath home in Winter Park’s desirable Woodcrest neighborhood. With quartz countertops, stainless steel appliances, and modern updates throughout, including a newer roof 2018, plumbing 2021, and windows 2019. This home is move-in ready. Relax on the covered back patio, entertain with ease, and enjoy

  DANIELLE RICHARDSON LA ROSA REALTY ORLANDO LLC

  5110 N Woodcrest Dr, Winter Park, FL 32792
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  /35

  $1,499 - $1,899 per month

  The Vista at Winter Park

  2 Beds

  4704 Lucier Ct, Winter Park, FL 32792

  Move in special- 2nd Full Month Free!*Restricted units only*Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!In a prime location of Winter Park, you will find our small and great community!Keeping the calm and great atmosphere, being able to relax by the lake, and being moments from shopping, dining, andmore, Set a tour today, and you will

  4704 Lucier Ct, Winter Park, FL 32792
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  /2

  $412,000 Sold Aug 22, 2025

  • 1,088 Sq Ft
  • $379/SF
  • 127 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  535 N Interlachen Ave Unit 107, Winter Park, FL 32789

  Location, Location, Location - downtown Winter Park condo for under $500K! This dramatic 2 bedroom - 2 Bath ground floor unit is located on corner of Swoop and Interlachen, steps from the Winter Park 9 Golf Course and Park Avenue! Beautiful views, glassed in porch overlooking stunning landscape. This unit offers high ceilings, open, updated kitchen to living areas, sunroom (enclosed porch)

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  535 N Interlachen Ave Unit 107, Winter Park, FL 32789
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  /2

  Est $476,818 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2939 Clever Ln, Winter Park, FL 32792

  2939 Clever Ln, Winter Park, FL 32792
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  /9

  $499,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,515 Sq Ft

  2485 Middleton Ave, Winter Park, FL 32792

  Wait no more! Don’t miss this charming and hard to find 3 bed/ 2 bath PLUS bonus room in Brookshire Heights! Large treed lot walking distance to Brookshire Elementary, Showalter Field, Cady Way Pool and Park and the Advent Health Winter Park Complex. Ready for your personal touches, this well loved home has large living room and dining area, terrazzo floors, vintage cabinetry, great closets

  Lisa Gould KELLER WILLIAMS WINTER PARK

  2485 Middleton Ave, Winter Park, FL 32792
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  /32

  $1,300 per month

  • 1 Bed
  • 1 Bath
  • 772 Sq Ft
  • Condo for Rent

  700 Melrose Ave Unit K32, Winter Park, FL 32789

  Discover Winter Park Gardens, an exclusive 55+ community nestled in the heart of historic Winter Park! Welcome to your private oasis at this one-bedroom, one-bathroom condo on the tranquil third floor, accessible by elevator. Enjoy sweeping views of the pool and beautifully landscaped courtyard from your unit, which includes a spacious storage closet in the foyer. Convenience is key with elevator

  Erica Diltz BALDWIN PARK REALTY LLC

  700 Melrose Ave Unit K32, Winter Park, FL 32789
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  /2

  $2,144,000 Sold Aug 21, 2025

  • 3,462 Sq Ft
  • $619/SF
  • 0 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2004

  1077 N Pennsylvania Ave, Winter Park, FL 32789

  Wonderful home in sought-after Pennsylvania Place. Newer roof (2019), HVAC and Water Heaters

  Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  1077 N Pennsylvania Ave, Winter Park, FL 32789
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  /89

  Est $1,325,921 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft

  3629 Midiron Dr, Winter Park, FL 32789

  3629 Midiron Dr, Winter Park, FL 32789
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  /40

  $3,275,000

  • 5 Beds
  • 7 Baths
  • 4,255 Sq Ft

  1610 Oakhurst Ave, Winter Park, FL 32789

  This stunning modern farmhouse residence, custom built in 2021 with meticulous attention to detail offering a bright-open living design, luxurious finishes, and an ideal floor plan for both everyday living and grand-scale entertaining. This home includes 5 en-suite bedrooms (owner’s suite & potential guest suite on 1st level) and 3 Bedrooms, plus lounge/flex area upstairs... or a 4 Bedroom,

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1610 Oakhurst Ave, Winter Park, FL 32789
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  /24

  $1,250 - $1,800 per month

  Park Apartments

  1 - 3 Beds

  7528 Park Promenade Dr, Winter Park, FL 32792

  WELCOME TO THE PARK APARTMENTS! Come join us in prestigious Winter Park. You will know as soon as you stroll down the beautiful lined drive, through the gates that you are in a distinctive community. We have five unique apartment floor plans to choose from, each with designer touches. the community has lush landscaping filled with many amenities. relax by either of the two swimming pools, work

  7528 Park Promenade Dr, Winter Park, FL 32792
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  /2

  $470,000 Sold Aug 21, 2025

  • 2,035 Sq Ft
  • $231/SF
  • 2 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1964

  2920 Abbey Ct, Winter Park, FL 32792

  Welcome home to the Winter Park Pines with tree lines streets, sidewalks on both sides of the street and a mailman that delivers to your door. This spacious 4-bedroom, 3-bath home offers the ideal canvas for customization, nestled in one of Winter Park’s most desirable neighborhoods. This diamond in the rough—brimming with charm and just waiting for your personal touch! Step inside through a

  Amy Turner KELLER WILLIAMS WINTER PARK

  2920 Abbey Ct, Winter Park, FL 32792
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  /38

  Est $757,568 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,894 Sq Ft

  1477 Lone Feather Trail, Winter Park, FL 32792

  1477 Lone Feather Trail, Winter Park, FL 32792
• 

  

  /20

  $575,000 Open Sun 11AM - 2PM

  • 4 Beds
  • 2 Baths
  • 2,036 Sq Ft

  1875 Staunton Ave, Winter Park, FL 32789

  Welcome to this newer single-family home tucked away in the Karolina On Killarney section of Winter Park. Situated on a generously sized .16 acre lot with no HOA, this property offers both privacy and optimal convenience. Enjoy hopping over to Park Avenue for shopping and restaurants or to the weekly Farmer's Market. Bustling College Park is a 5-minute jaunt down the road and I-4 is 2-minutes

  Jill Healey KELLER WILLIAMS WINTER PARK

  1875 Staunton Ave, Winter Park, FL 32789
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  /36

  $2,195 per month

  • 3 Beds
  • 1 Bath
  • 1,158 Sq Ft
  • House for Rent

  1805 Edwin Blvd, Winter Park, FL 32789

  Updated 3-Bedroom, 1-Bath Winter Park single family home is now available! This charming 1951 block home has been beautifully updated with a modern kitchen and new tile flooring throughout. It features a retro-style bathroom with a tub conveniently located off the hallway near the three bedrooms. Additional highlights include a single-car garage with washer and dryer hookups, a living and dining

  Amy Spano WMGI

  1805 Edwin Blvd, Winter Park, FL 32789
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  /2

  $255,000 Sold Aug 21, 2025

  • 1,290 Sq Ft
  • $198/SF
  • 7 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  2398 Dominica Run, Winter Park, FL 32792

  **This property qualifies for a closing cost credit up to $3,900 through the Seller’s preferred lender.** Charming Winter Park Townhome with Vaulted Ceilings and Sun-Filled Spaces. Welcome to 2398 Dominica Way, a beautifully maintained 2-bedroom, 2-bathroom townhome nestled in the heart of Winter Park. From the moment you arrive, you'll be drawn in by the inviting front patio, complete with a

  Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  2398 Dominica Run, Winter Park, FL 32792
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  /2

  Est $210,993 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft

  200 Saint Andrews Blvd Unit 3704, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 3704, Winter Park, FL 32792
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  /37

  $395,900

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  1566 Lawndale Cir, Winter Park, FL 32792

  Welcome to 1566 Lawndale Circle, a beautifully remodeled 3-bedroom, 2-bath pool home situated in the heart of Winter Park. This move-in ready residence blends modern updates with Florida charm, has a light and open floor plan designed for both comfort and entertaining. Step inside to find a freshly renovated interior featuring brand-new flooring, updated kitchen with quartz countertops, stainless

  Steven Koleno BEYCOME OF FLORIDA LLC

  1566 Lawndale Cir, Winter Park, FL 32792
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  /31

  $1,489 - $1,779 per month

  POSTE Winter Park

  1 - 2 Beds

  800 Semoran Park Dr, Winter Park, FL 32792

  Welcome to Poste Winter Park, where the beauty of classic period architecture meets the modern comforts of today. Nestled in the heart of trendy Winter Park, Florida, our community is your gateway to a vibrant, convenient, and tranquil lifestyle. Poste Winter Park offers a boutique feel with newly remodeled facilities, spacious floor plans, and signature customer service. Located just across from

  800 Semoran Park Dr, Winter Park, FL 32792
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  /2

  $1,400,000 Sold Aug 21, 2025

  • 4,181 Sq Ft
  • $335/SF
  • 60 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1979

  1327 Bridgeport Dr, Winter Park, FL 32789

  This 5 bedroom, 4 full bathroom one story refreshed ranch estate boasts nearly 4,200 sq ft and features 3 fireplaces, double primary suites, and sprawls out on an oversized .36 acre lot, overlooking an open air salt water & solar heated pool. Updates & upgrades include: full roof replacement with transferable warranty (2023), new windows with transferable warranty (2023), 4 newer ACs (2 are 2023

  Jennifer Christ RE/MAX TOWN & COUNTRY REALTY

  1327 Bridgeport Dr, Winter Park, FL 32789
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  /2

  Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,079 Sq Ft

  3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792

  3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792
• 

  

  /99

  $1,999,999

  • 4 Beds
  • 3.5 Baths
  • 3,161 Sq Ft

  1661 Hillcrest Ave, Winter Park, FL 32789

  Luxurious Winter Park Retreat with Stunning Features! Welcome to 1661 Hillcrest Avenue, a masterpiece of coastal design nestled in the heart of the highly sought after Winter Park. This exceptional property presents an exclusive opportunity to own a home crafted by the Parade of Home Winner, Lazarus Development Group. This elegant home boasts 4 bedrooms, 3.5 baths, and a 2 car garage. As you step

  Domenique Lombardo ROYALTY R E BOUTIQUE INC

  1661 Hillcrest Ave, Winter Park, FL 32789
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  /16

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • House for Rent

  633 Balfour Dr, Winter Park, FL 32792

  MOVE-IN READY! PERFECT LOCATION IN WINTER PARK! NEWLY REMODELED! NEW PAINTING! NEW WOOD AND TILE FLOORING! NO CARPETS! NEW BATH! NEW KITCHEN COUNTERTOP AND BACKSPLASH! NEW VANITIES!...NO HOA! 3 Bedroom 2 Full Bath with open floor plan, Full of nature lighting, Plenty of parking space,Sizable back yard and front yard. Very convenient to shopping, restaurants, Costco, short drive to UCF, Baldwin

  Jacky Liu YORK MILLS REALTY LLC

  633 Balfour Dr, Winter Park, FL 32792
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  /2

  $279,000 Sold Aug 20, 2025

  • 1,241 Sq Ft
  • $225/SF
  • 32 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  3153 Greenwood St Unit Winter Spr, Winter Park, FL 32792

  Move-In Ready and AFFORDABLE one-story townhouse with FENCED YARD, 1-Car Garage and LOW HOA!!!!Situated on a corner lot with a screened patio and no rear neighbors, it offers just the right mix of privacy and convenience. Inside, you’ll find ceramic tile and luxury vinyl flooring throughout...so no carpet in sight! A spacious kitchen, living and dining spaces, large bedrooms and 2 tastefully

  Allison Day RE/MAX TOWN & COUNTRY REALTY

  3153 Greenwood St Unit Winter Spr, Winter Park, FL 32792
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  /2

  Est $467,139 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  Unlisted Address

  Unlisted Address
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  /15

  $400,000

  • Land
  • 0.21 Acre
  • $1,904,762 per Acre

  1809 Palmer Ave, Winter Park, FL 32792

  Build your dream home in the heart of Winter Park! Located on the highly desirable Palmer Avenue, this premium lot offers a rare opportunity to create a custom residence just minutes from Park Avenue, Rollins College, top-rated schools, and the Winter Park Chain of Lakes. Situated among multi-million-dollar homes, this property is ideal for discerning buyers or builders seeking a great address

  Christina Munkberg COLDWELL BANKER RESIDENTIAL RE

  1809 Palmer Ave, Winter Park, FL 32792
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  /30

  $1,245 - $2,650 per month

  Signal Pointe

  1 - 3 Beds

  2500 Howell Branch Rd, Winter Park, FL 32792

  Come home to the lifestyle you've been dreaming of in a pet-friendly apartment home at Signal Pointe Apartment Homes near Rollins College.Offering the ideal blend of modern apartment features and elevated community amenities, these garden-style Winter Park, Florida, apartments offer the convenience you've been looking for - all within the tranquility of the suburbs. Make your move to

  2500 Howell Branch Rd, Winter Park, FL 32792
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  /2

  $3,350,000 Sold Aug 20, 2025

  • 3,223 Sq Ft
  • $1,039/SF
  • 1 Day On Market

  • 4 Beds
  • 3 Baths
  • Built 1966

  641 Virginia Dr, Winter Park, FL 32789

  Welcome to 641 Virginia Drive, a rare and remarkable lakefront property located in the highly sought-after Timberlane Shores neighborhood of Winter Park. This expansive .48-acre lot offers approximately 100 feet of frontage on Lake Virginia, one of the most desirable lakes on the prestigious Winter Park Chain of Lakes.The existing 4-bedroom, 3-bath home features 3,223 square feet of

  Audra Wilks KELLER WILLIAMS WINTER PARK

  641 Virginia Dr, Winter Park, FL 32789
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  /2

  Est $459,250 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2838 Bright Bird Ln, Winter Park, FL 32792

  2838 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /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 most established lakefront communities, ideally located 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

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 503, Winter Park, FL 32789
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  /19

  $1,895 per month

  • 2 Beds
  • 2.5 Baths
  • 1,133 Sq Ft
  • Townhouse for Rent

  200 Sandlewood Trail Unit 4, Winter Park, FL 32789

  ovely, light and airy home with newer appliances, fresh paint through out and newer laminate flooring upstairs. The kitchen shines with natural light and eat-in space, large window that floods the room with natural light. The spacious living and dining features a corner fireplace - tile flooring and over-sized sliders that open to back patio and greens space...pool is short walk across the yard.

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  200 Sandlewood Trail Unit 4, Winter Park, FL 32789
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  /2

  $560,000 Sold Aug 20, 2025

  • 1,420 Sq Ft
  • $394/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1957

  1901 Loch Berry Rd, Winter Park, FL 32792

  A rare opportunity in the heart of Winter Park—this property sits on an oversized 0.31-acre corner lot in one of the area’s most desirable neighborhoods. This lot has no rear neighbors offering even more privacy. The existing home is owner-occupied, functional, and will be sold AS-IS, though it will require repairs. The true value lies in the land, offering outstanding potential for renovation,

  Monica Tipirneni FOLIO REALTY LLC

  1901 Loch Berry Rd, Winter Park, FL 32792
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  /35

  Est $229,468 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft

  656 Saint Johns Ct Unit S, Winter Park, FL 32792

  656 Saint Johns Ct Unit S, Winter Park, FL 32792
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  /64

  $5,999,000

  • 5 Beds
  • 5.5 Baths
  • 6,708 Sq Ft

  1240 Harding St, Winter Park, FL 32789

  This stunning private residence is situated on an oversized lot featuring a private sports pad, kids playground, and sparkling pool. Encompassing over 6,700 square feet of expansive .55 -acre lot, this home boast 5 spacious bedrooms, 1 office, 5.5 bathrooms and a dedicated movie room, recording studio, and a fully equipped gym with a private sauna. Ideally situated just moments from the serene

  Nathalie Bates PREMIER SOTHEBY'S INTL. REALTY

  1240 Harding St, Winter Park, FL 32789
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  /35

  $976 - $1,373 per month

  GOLDEN OAKS

  2 - 3 Beds

  7701 Acorn Woods Cir, Winter Park, FL 32792

  Golden Oaks Apartments is your destination for quality, affordable living, offering spacious two and three-bedroom apartment options designed to meet your needs. Located in a serene, peaceful area, our community combines the tranquility of a residential neighborhood with the convenience of nearby shopping, dining, and entertainment. With income restrictions in place to ensure affordability,

  7701 Acorn Woods Cir, Winter Park, FL 32792
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  /2

  $455,000 Sold Aug 20, 2025

  • 1,804 Sq Ft
  • $252/SF
  • 59 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2003

  3304 Bennington Ct, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome Home! This immaculate 3-bedroom, 2-bathroom single family home is perfectly designed for comfortable family living. Featuring a desirable split floor plan, this move in ready gem offers space, style, and convenience in every corner. The heart of the home is the modern kitchen, complete with stainless steel appliances and brand new, gorgeous

  Peter Hamilton DAHLIA REALTY GROUP

  3304 Bennington Ct, Winter Park, FL 32792
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  /2

  Est $347,889 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

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

  230 Killarney Bay Ct Unit 3, Winter Park, FL 32789
• 

  

  /32

  $649,900 Open Sun 11AM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft

  2330 Coldstream Dr, Winter Park, FL 32792

  Modern luxury meets Winter Park charm — fully renovated 4BR/2BA with $20K seller credit with full price purchase! This beautifully reimagined 4-bedroom, 2-bath home has undergone a complete transformation. Every detail thoughtfully designed and executed. From brand-new plumbing, electrical, and HVAC systems, to a stunning new floor plan created by an international architect, this home blends

  Caio Garcia de Souza Monteiro AUTHENTIC REAL ESTATE TEAM

  2330 Coldstream Dr, Winter Park, FL 32792
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  /17

  $2,550 per month

  • 3 Beds
  • 1 Bath
  • 1,349 Sq Ft
  • House for Rent

  955 Minnesota Ave, Winter Park, FL 32789

  Welcome to your new home at 955 Minnesota Avenue, nestled in the heart of charming Winter Park. This beautiful 3 bedroom, 1 bathroom home perfectly balances timeless character and thoughtful updates while offering incredible proximity to Park Avenue, Orange Avenue, Hannibal Square, and the city’s historic district. Step inside to a light-filled living room showcasing gleaming wood floors and a

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  955 Minnesota Ave, Winter Park, FL 32789
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  /2

  $4,087,500 Sold Aug 20, 2025

  • 5,847 Sq Ft
  • $699/SF
  • 609 Days On Market

  • 5 Beds
  • 9 Baths
  • Built 1957

  421 Lakewood Dr, Winter Park, FL 32789

  This elegant Winter Park lakefront residence offers luxury lakeside living, situated on the picturesque shores of Lake Osceola. This exquisite home invites you in with a grand circular driveway and meticulous, landscaped grounds, combined with elevated panoramic views from a spacious 3/4 acre lot, with approx. 140 feet on the street and approx.. 110 feet of prime lake frontage. This property

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  421 Lakewood Dr, Winter Park, FL 32789
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  /24

  Est $379,300 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft

  172 Balfour Dr Unit 2, Winter Park, FL 32792

  172 Balfour Dr Unit 2, Winter Park, FL 32792

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