Winter Park, FL Homes

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  /8

  $260,000

  • Land
  • 0.81 Acre
  • $320,988 per Acre

  3580 Wilde Ave, Winter Park, FL 32792

  Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just shy of an acre, lot in coveted Winter Park. Nestled on a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level lot on a

  

  Gwendolen Flynn

  COLDWELL BANKER RESIDENTIAL RE

  (321) 334-2867

  3580 Wilde Ave, Winter Park, FL 32792
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• 

  

  

  /38

  $1,202 - $1,669 per month

  Seabrook

  1-2 Beds

  3114 Terry Brook Dr, Winter Park, FL 32792

  The Seabrook Apartment community is located near the 408 Expressway, close to shopping and dining areas 1/4 mile away, just minutes away from the downtown areas of Orlando and Winter Park. Several renowned schools such as Brookshire Elementary, Glenridge Middle School and Winter Park High School are nearby as well. We offer spacious one and two-bedroom apartments. All of our homes have been

  3114 Terry Brook Dr, Winter Park, FL 32792
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  /2

  $286,000 Sold Jul 17, 2025

  • 1,401 Sq Ft
  • $204/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  1670 Clematis Ln, Winter Park, FL 32792

  Location, Location, Location! Don’t miss this fantastic opportunity in highly desirable Winter Park—a beautiful 3-bedroom, 2-bath home with a heated pool! Recent Upgrades Include: Pool resurfaced (2023), Electrical panel replaced (2023), New roof and AC (2021), New water heater, Fully fenced backyard for privacy and convenience. While the home boasts major mechanical updates, the price reflects

  Betsy Breton-Garcia KELLER WILLIAMS WINTER PARK

  1670 Clematis Ln, Winter Park, FL 32792
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  /44

  Est $894,432 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,602 Sq Ft

  436 W Swoope Ave, Winter Park, FL 32789

  436 W Swoope Ave, Winter Park, FL 32789
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  /36

  $765,000

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft

  2418 Whitehall Cir, Winter Park, FL 32792

  MAJOR PRICE REDUCTION! MOTIVATED SELLER! Don't miss out!!! A true GEM located in the highly desirable Brookshire Heights, presenting this FULLY REMODELED spacious single-story property in the heart of WINTER PARK. Showcasing a new meticulously designed floorplan, this property has also recently been EXTENDED by a total approx. 1,040 sqft. Exuding luxury in a modern setting and with stunning curb

  

  Alice Anne Jackson

  CORCORAN PREMIER REALTY

  (321) 599-7240

  2418 Whitehall Cir, Winter Park, FL 32792
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  /17

  $2,999 per month

  • 3 Beds
  • 2 Baths
  • 1,641 Sq Ft
  • House for Rent

  101 S Lakemont Ave, Winter Park, FL 32792

  Welcome to this beautifully renovated 3-bedroom, 2-bathroom single-family home, perfectly positioned just minutes away from shopping, dining, and all the charm of Winter Park. This home combines modern luxury with everyday convenience. As you step inside, you're greeted by the elegance of Calacatta Quartz countertops, sleek waterproof flooring, and top-of-the-line appliances that set the tone for

  Robert Isaac Rodriguez RE/MAX DOWNTOWN

  101 S Lakemont Ave, Winter Park, FL 32792
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  /2

  $760,000 Sold Jul 17, 2025

  • 2,192 Sq Ft
  • $347/SF
  • 42 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2019

  2159 Marsh Sedge Ln, Winter Park, FL 32792

  JUST LISTED - FANTASTIC WINTER PARK CONSERVATION LOT HOME LOCATED IN THE HEART OF THE PRESERVE AT HAWKS CREST!– 2159 Marsh Sedge Lane, Winter Park – Stunning Hawk’s Crest Residence – Offered at $789,000! Highly desirable, single-story residence in Winter Park’s newest gated community. This is the Pomelo model built by Meritage Homes. An absolutely stunning, immaculate, "betterthan new

  Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  2159 Marsh Sedge Ln, Winter Park, FL 32792
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  /33

  Est $641,765 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,265 Sq Ft

  5319 Pine Lily Cir, Winter Park, FL 32792

  5319 Pine Lily Cir, Winter Park, FL 32792
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  /19

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  7706 Country Place Unit A8, Winter Park, FL 32792

  Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining

  

  Carmen Vazquez

  REALTY TECH INC

  (321) 215-7673

  7706 Country Place Unit A8, Winter Park, FL 32792
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  /28

  $1,661 - $1,686 per month

  Elon Winter Park

  1 Bed

  712 Nicolet Ave, Winter Park, FL 32789

  Welcome to Elon Winter Park Apartments in Winter Park, Florida, where chic meets serenity in the heart of Winter Park's vibrant tapestry. Nestled within this charming community, our boutique one-bedroom apartments redefine urban living with spacious interiors, a contemporary aesthetic, and designer accents that elevate every moment. Immerse yourself in the allure of Winter Park's entertainment

  712 Nicolet Ave, Winter Park, FL 32789
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  /2

  $252,500 Sold Jul 17, 2025

  • 1,669 Sq Ft
  • $151/SF
  • 65 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1985

  2309 Sun Valley Cir, Winter Park, FL 32792

  Welcome to the largest floor plan in the community! This beautifully maintained 2 bedroom, 2 bathroom condo offers a fresh coat of interior paint and a thoughtfully designed layout perfect for comfortable living and entertaining.The main floor features two spacious bedrooms and an open-concept living and dining area, while the upstairs boasts a generous loft—ideal for a third bedroom,

  Kristin Vogt CENTURY 21 INTEGRA

  2309 Sun Valley Cir, Winter Park, FL 32792
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  /31

  Est $212,153 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft

  3307 Amber Wood Way Unit 106, Winter Park, FL 32792

  3307 Amber Wood Way Unit 106, Winter Park, FL 32792
• 

  

  /23

  $525,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,191 Sq Ft

  2327 Mulbry Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Charming Mid-Century Ranch in Prime Winter Park Location – Steps from Blue Jacket Park. Ideally situated in the heart of Winter Park and just a stone’s throw from Baldwin Park’s beloved Blue Jacket Park, this tastefully updated 3 BEDROOM, PLUS OFFICE, 1.5 BATHROOM home blends timeless character with modern touches. Enjoy a freshly painted interior,

  

  Charlie Peterson

  KELLER WILLIAMS HERITAGE REALTY

  (321) 499-2363

  2327 Mulbry Dr, Winter Park, FL 32789
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  /32

  $3,350 per month

  • 3 Beds
  • 2 Baths
  • 1,732 Sq Ft
  • House for Rent

  1816 Mizell Ave, Winter Park, FL 32789

  Welcome to this charming 3-bedroom, 2-bath home in the heart of Winter Park, complete with a 1-car garage and unbeatable location. Just minutes from Park Avenue, Winter Park Hospital, top-rated shopping, and dining, convenience is at your doorstep. Start your mornings with peaceful strolls through the beautiful Windsong neighborhood and take in the serene views of Lake Mizell. Whether you're

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  1816 Mizell Ave, Winter Park, FL 32789
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  /2

  $310,000 Sold Jul 17, 2025

  • Land
  • 1.01 Acres
  • $306,931 per Acre

  • 94 Days On Market

  3520 Wilde Ave, Winter Park, FL 32792

  Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just over an acre, lot in coveted Winter Park. Nestled on the end of a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level

  Gwendolen Flynn COLDWELL BANKER RESIDENTIAL RE

  3520 Wilde Ave, Winter Park, FL 32792
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  /15

  Not Listed For Sale

  • 2 Beds
  • 3,098 Sq Ft

  1858 Cornell Ave, Winter Park, FL 32789

  1858 Cornell Ave, Winter Park, FL 32789
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  /45

  $1,300,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,303 Sq Ft

  1500 Mizell Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. An extraordinary opportunity to own a beautifully renovated home on a prestigious tree-lined street in Winter Park’s 32789. Set on a desirable 13,500 square foot (90 × 150) lot with no HOA and bordering the prestigious Windsong community, this prime property offers the freedom to live comfortably now, expand

  

  Lisa Ratanasirintrawoot

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 485-6636

  1500 Mizell Ave, Winter Park, FL 32789
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  /43

  $1,764 - $3,216 per month

  Bainbridge Winter Park

  1-3 Beds

  1400 Morgan Stanley Ave, Winter Park, FL 32789

  Celebrate the power of possibilities. Signature details enhance grand features in expansive homes, all a promise to your heightened prosperity at Bainbridge Winter Park. In the heart of Winter Park, Florida’s lush parks and gardens, museums, festivals, and events - you’re central to the finer things in life.

  1400 Morgan Stanley Ave, Winter Park, FL 32789
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  /2

  $439,000 Sold Jul 17, 2025

  • 1,688 Sq Ft
  • $260/SF
  • 137 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1965

  2823 Cady Way, Winter Park, FL 32792

  Gorgeous new flooring throughout the home!!New roof 2020! New water heater 2025. Beautiful Winter Park 4 Bedroom/ 2 Bath home in the sought-after Winter Park Pines neighborhood! This lovely residence has a beautiful split floorplan with lots of natural light! This home offers both a separate family room and living room to provide ample space to entertain or enjoy a relaxing evening with the

  Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

  2823 Cady Way, Winter Park, FL 32792
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  /60

  Est $1,675,376 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,105 Sq Ft

  1318 Chapman Cir, Winter Park, FL 32789

  1318 Chapman Cir, Winter Park, FL 32789
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  /100

  $8,500,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,564 Sq Ft

  2661 Vía Tuscany, Winter Park, FL 32789

  CALLING HIGHEST AND BEST BY 4/30/2025!! Introducing a Unique, Stunning Modern HomeA groundbreaking architectural masterpiece, this one-of-a-kind residence is built with reinforced concrete, steel, and iron framing, featuring floor-to-ceiling glass walls with no traditional windows. Designed to exceed Florida’s strictest building codes, this home follows commercial-grade

  

  Prescilla Vazquez

  PV LUXURY GROUP PA

  (321) 478-2671

  2661 Vía Tuscany, Winter Park, FL 32789
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  /18

  $3,600 per month

  • 4 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • House for Rent

  1846 Barker Dr, Winter Park, FL 32789

  Welcome to 1846 Barker Dr- a charming and well maintained single family home located in one of Winter Park's most desirable neighborhoods. This inviting 4- bedrooms, -2 bath residence offers a perfect blend of comfort and convenience, just minutes from top-rated schools, beautiful parks, shopping, dining and all amenities of the sought-after Winter Park-Baldwin Park lifestyle. Enjoy a bright and

  Cliff Glansen FLATFEE.COM

  1846 Barker Dr, Winter Park, FL 32789
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  /2

  $400,000 Sold Jul 16, 2025

  • 1,503 Sq Ft
  • $266/SF
  • 15 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1967

  3443 Arnel Dr, Winter Park, FL 32792

  Welcome home to 3443 Arnel Drive, perfectly positioned in the heart of Eastbrook, one of Winter Park’s most desired and established neighborhoods. This home effortlessly balances classic character with thoughtful updates, offering a layout that just makes sense! Whether you're raising a family, hosting friends, or simply enjoying your own space. This home is a must see! Step inside and you’re

  Lana More KELLER WILLIAMS WINTER PARK

  3443 Arnel Dr, Winter Park, FL 32792
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  /9

  Est $292,449 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,041 Sq Ft

  5774 Shale Ct, Winter Park, FL 32792

  5774 Shale Ct, Winter Park, FL 32792
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  /45

  $949,000 New Construction

  • 4 Beds
  • 3 Baths
  • 2,646 Sq Ft

  1840 Biscayne Dr, Winter Park, FL 32789

  Biscayne Bay, a recent Parade of Homes winner, is one of the latest custom builds by the trusted team at Konkol Custom Homes—and it’s ready for its very first owner. Set in a prime Winter Park location, this two-story home offers clean lines, high-end finishes, and a layout that fits real life.With just over 2,600 square feet under air, the home features 4 bedrooms and 3 full bathrooms.

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 346-4741

  1840 Biscayne Dr, Winter Park, FL 32789
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  /53

  $1,449 - $2,029 per month

  Serena Winter Park

  1-2 Beds

  2890 Red Lion Square, Winter Park, FL 32792

  Serena Winter Park is a newly remodeled apartment community. Our one and two bedroom apartment floor plans feature contemporary upgrades, large windows, spacious walk in closets, open kitchen styles and fantastic storage spaces. Our bungalow flats also offer private entry and patio. Our pet-friendly apartment community includes an all new impeccable 24-hour fitness center and billiards lounge! A

  2890 Red Lion Square, Winter Park, FL 32792
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  /2

  $192,000 Sold Jul 16, 2025

  • 1,059 Sq Ft
  • $181/SF
  • 40 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  4878 Tangerine Ave, Winter Park, FL 32792

  WATCH REAL VIDEO & 3D TOUR! Welcome to 4878 Tangerine Ave, a beautifully MOVE IN READY- NEW ROOF - NEW FLOORS- FRESH PAINT updated 2-bedroom, 2-bathroom condo nestled in the serene and highly desirable Wrenwood Condominiums of Winter Park with Community POOL/GYM and ample parking. Yard maintenance, Roof replacement, Trash, and Water are included in the HOA. Step inside and be greeted by

  Arthur Love LA ROSA REALTY ORLANDO LLC

  4878 Tangerine Ave, Winter Park, FL 32792
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  /25

  Est $213,552 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft

  7436 Woodburn Ct Unit 27, Winter Park, FL 32792

  7436 Woodburn Ct Unit 27, Winter Park, FL 32792
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  /29

  $365,000

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft

  2006 Ponderosa Ave, Winter Park, FL 32792

  Pure Potential in Winter Park’s Eastbrook Community! Renovate or move-in, this is a great opportunity for an investor or homebuyer. Spacious 1,467 SF home with 3 bedrooms, 2 full baths, living & family room + a home office/den which could easily be converted into a 4th bedroom. New carpet in each bedroom. Fresh paint throughout. Attached 2-car garage with laundry. Custom built shed has plenty of

  Kelly Price KELLY PRICE & COMPANY LLC

  2006 Ponderosa Ave, Winter Park, FL 32792
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  /19

  $3,995 per month

  • 4 Beds
  • 2 Baths
  • 2,126 Sq Ft
  • House for Rent

  3131 Lowndes Dr, Winter Park, FL 32792

  Stunning Furnished 4-Bedroom Poolside Retreat in Winter Park School district; Winter Park High, Maitland Middle and Lakemont ElementaryPrepare to be captivated from the moment you step into this beautiful fully renovated masterpiece. A seamless open floorplan welcomes you, effortlessly blending the entryway into a sun-kissed living and dining area that gazes out onto your private,

  Rene' Fossey A +ROI PROPERTY

  3131 Lowndes Dr, Winter Park, FL 32792
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  /2

  $285,123 Sold Jul 15, 2025

  • 1,310 Sq Ft
  • $218/SF
  • 24 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  5588 Garden Grove Cir, Winter Park, FL 32792

  Location, Location, Location! This 3-bedroom, 2-bathroom gem is perfect for families and offers everything you need to feel right at home. This one boasts a Great Room Plan that’s perfect for entertaining! The gally kitchen has a Breakfast Bar and overlooks the dining area and great room. The home offers a 3-way split The Master Suite has with Stall Shower and laminate flooring. You’ll also find

  Joyce Sanders FLORIDA REAL ESTATE PROPERTIES LLC

  5588 Garden Grove Cir, Winter Park, FL 32792
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  /24

  Est $191,024 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  229 Lewfield Cir Unit 229, Winter Park, FL 32792

  229 Lewfield Cir Unit 229, Winter Park, FL 32792
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  /41

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,263 Sq Ft

  5331 Oak Ct, Winter Park, FL 32792

  Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to

  Nataliya Voroshylo CHARLES RUTENBERG REALTY ORLANDO

  5331 Oak Ct, Winter Park, FL 32792
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  /110

  $1,500 - $2,075 per month

  Oak Reserve at Winter Park

  1-3 Beds

  541 Oak Reserve Ln, Winter Park, FL 32792

  Welcome home to Oak Reserve at Winter Park Apartments, a quiet community where your needs and wishes are our priority. Covering all the bases for a comfortable living experience, our apartments in Winter Park, FL, are completed by lifestyle-oriented amenities, fantastic services, and a well-connected location within walking distance of Full Sail University. Short-term leases are available,

  541 Oak Reserve Ln, Winter Park, FL 32792
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  /2

  $400,000 Sold Jul 15, 2025

  • 1,704 Sq Ft
  • $235/SF
  • 23 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1974

  1017 Manchester Cir, Winter Park, FL 32792

  Under contract-accepting backup offers. Seller will assist with closing costs! Welcome to your dream home in the highly sought-after Howell Estates community of Winter Park, Florida! This immaculate four-bedroom, two-bathroom residence is perfectly situated on just under a quarter acre, surrounded by lush, mature landscaping that enhances its curb appeal. Step inside this well-maintained gem,

  Jenaia Fowlkes FOWLKES REALTY CO

  1017 Manchester Cir, Winter Park, FL 32792
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  /45

  Est $1,959,192 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 3,954 Sq Ft

  1433 Sarazens Place, Winter Park, FL 32792

  1433 Sarazens Place, Winter Park, FL 32792
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  /36

  $535,000 Open Sat 2PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 1,811 Sq Ft

  1819 Shadyhill Terrace, Winter Park, FL 32792

  Welcome to your own private retreat, perfectly situated at the end of a quiet CUL-DE-SAC on one of the most SCENIC LOTS in the neighborhood. This beautiful home sits on a gorgeous, oversized 1/4-ACRE LOT with UNOBSTRUCTED WATER VIEWS and is framed by mature trees, creating a natural canopy that offers both beauty and privacy. Whether you're sipping your morning coffee or winding down in the

  Jonathan Ruiz KELLER WILLIAMS WINTER PARK

  1819 Shadyhill Terrace, Winter Park, FL 32792
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  /16

  $2,380 per month

  • 3 Beds
  • 2 Baths
  • 1,909 Sq Ft
  • House for Rent

  2717 Amsden Rd, Winter Park, FL 32792

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

  Nico Silva Vanegas MAIN STREET RENEWAL LLC

  2717 Amsden Rd, Winter Park, FL 32792
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  /2

  $266,000 Sold Jul 15, 2025

  • 1,092 Sq Ft
  • $244/SF
  • 25 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1985

  5518 Cretan Way, Winter Park, FL 32792

  This charming 2-bedroom, 2-bath townhome in the quiet and friendly Fernbrook Trails community in Winter Park is ready for it's new owner. This one-story home has a warm, open feel with wood-look tile flooring throughout. The kitchen has everything you need—stainless steel appliances, a closet pantry, and tons of cabinet and counter space—and it opens right up to the dining area, making it great

  Liam Pool HOMEVEST REALTY

  5518 Cretan Way, Winter Park, FL 32792
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  /14

  Est $595,255 Not Listed For Sale

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

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789

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