Winter Park, FL Homes

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  /44

  $775,000

  • 4 Beds
  • 2.5 Baths
  • 2,637 Sq Ft

  2167 Marsh Sedge Ln, Winter Park, FL 32792

  Nestled within the highly sought-after gated community of Hawks Crest in Winter Park, this rare Florentine model by Meritage Homes offers over 2,600 square feet of modern luxury, comfort, and style on a premium, private lot with no rear neighbors. Designed for today's lifestyle, this two-story contemporary masterpiece delivers both peace and elegance in every detail. As you step inside, you’re

  Harif Hazera PREMIER SOTHEBY'S INTL. REALTY

  2167 Marsh Sedge Ln, Winter Park, FL 32792
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  /30

  $1,700 - $2,691 per month

  Rosalia Winter Park 55+ Active Adult Commu...

  1 - 2 Beds

  3045 Aloma Ave, Winter Park, FL 32792

  Browse our 1 and 2-bedroom luxury 55+ apartments at Rosalia Winter Park, complete with modern appliances and stunning finishes. Stay connected and engaged with countless luxury amenities and activities designed for your lifestyle by our dedicated onsite management team and exciting amenities, including a clubhouse, fitness center, and robust social calendar—all with an attentive team at your

  3045 Aloma Ave, Winter Park, FL 32792
• 

  

  /2

  $610,000 Sold Aug 25, 2025

  • 1,627 Sq Ft
  • $375/SF
  • 162 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1953

  2812 Mulford Ave, Winter Park, FL 32789

  Welcome to 2812 Mulford Avenue. This updated 3 bedroom and 2 bath home is located perfectly in Winter Park. Walking distance to East End Market, close to Rollins College, steps from Baldwin Park, 1 mile from Mills 50 area, and close to Mead Gardens, Leu Gardens and Loch Haven Park. The neighborhood is quiet with low traffic, oversized lots, and NO HOA, yet surrounded by amazing schools, local

  Haley Young SYNCHRONICITY REAL ESTATE SOLUTIONS

  2812 Mulford Ave, Winter Park, FL 32789
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  /2

  Est $738,640 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,582 Sq Ft

  1304 Blue Stem Ln, Winter Park, FL 32792

  1304 Blue Stem Ln, Winter Park, FL 32792
• 

  

  

  /52

  $893,000

  • 5 Beds
  • 3 Baths
  • 2,242 Sq Ft

  1927 Eland Ave, Winter Park, FL 32789

  Tucked away on a quiet dead-end street with no rear neighbors, 1927 Eland Avenue combines charm, versatility, and an unbeatable Winter Park lifestyle. This beautifully maintained property offers both a character-filled main home and a modern detached in-law suite.The main residence features 3 bedrooms, 2 bathrooms, real wood floors, abundant natural light, and warm Spanish Colonial

  Adriana Gonzalez PERFECT INVESTMENT REALTY

  1927 Eland Ave, Winter Park, FL 32789
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  /14

  $1,885 per month

  • 3 Beds
  • 2 Baths
  • 1,409 Sq Ft
  • House for Rent

  2111 Conifer Ave, Winter Park, FL 32792

  Welcome to this solid masonry home in Winter Park offering 1,409 square feet of comfortable living space. Built in 1969 and thoughtfully maintained, the home sits on a spacious 10,062 square foot lot. Located in a serene Winter Park neighborhood near Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High.

  Jonathan Minerick HOMECOIN.COM

  2111 Conifer Ave, Winter Park, FL 32792
• 

  /2

  $530,000 Sold Aug 22, 2025

  • 2,254 Sq Ft
  • $235/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  7682 Glenmoor Ln, Winter Park, FL 32792

  Welcome to 7682 Glenmoor Lane – Located in the established community of Glenmoor, zoned for Winter Park HS, Maitland Middle and Lakemont Elementary.This beautifully renovated Winter Park gem is situated on a generous 0.26-acre lot, this stunning single-family home blends timeless style with modern updates throughout.Step inside to discover custom tile flooring, solid wood cabinetry in

  Bob Holston, Jr HOLSTON PROPERTIES & DEV., INC

  7682 Glenmoor Ln, Winter Park, FL 32792
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  /15

  Est $116,994 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,085 Sq Ft

  192 Scottsdale Square Unit 192, Winter Park, FL 32792

  192 Scottsdale Square Unit 192, Winter Park, FL 32792
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  /35

  $200,000

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  2500 Lee Rd Unit 219, Winter Park, FL 32789

  Welcome to life on Lake Killarney, one of Winter Park’s most sought-after lakefront communities! This charming 2-bedroom, 1-bathroom condo offers an unbeatable location and resort-style amenities—perfect for those seeking the true Florida lifestyle.Enjoy direct access to Lake Killarney, where residents can take advantage of boat slips available at a low cost on a first-come, first-serve basis, as

  Nicole Van Treese SUNDIAL REAL ESTATE LLC

  2500 Lee Rd Unit 219, Winter Park, FL 32789
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  /35

  $1,497 - $2,751 per month

  Stonecastle Apartment Homes

  1 - 3 Beds

  2015 New Stonecastle Terrace, Winter Park, FL 32792

  Stonecastle Apartments is the community you've been looking for in Winter Park, FL. With spacious one-, two-, and three-bedroom homes complete with in-home washers and dryers, stainless steel appliances, and smart thermostats, you're guaranteed to find a place to live with a lifestyle to love. What's more, as a member of the community you'll also have access to our fitness center, resident

  2015 New Stonecastle Terrace, Winter Park, FL 32792
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  /2

  $1,295,000 Sold Aug 22, 2025

  • 4,161 Sq Ft
  • $311/SF
  • 8 Days On Market

  • 6 Beds
  • 4 Baths
  • Built 2015

  1422 Via Sangro Place, Winter Park, FL 32792

  Welcome to your WATERFRONT dream home in the prestigious Lakeside Estates, a private gated community situated on Garden Lake. Highly desirable cul-de-sac location and short stroll to the playground. The Kerrville model home is designed for stylish, easy living and offers an open floor plan with high-end finishes throughout. Impress your family and friends with the inviting foyer, 20+ ceilings,

  Jennifer Sloan KELLY PRICE & COMPANY LLC

  1422 Via Sangro Place, Winter Park, FL 32792
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  /2

  Est $294,051 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,470 Sq Ft

  7164 Swallow Run Unit GE, Winter Park, FL 32792

  7164 Swallow Run Unit GE, Winter Park, FL 32792
• 

  

  /55

  $980,000

  • 4 Beds
  • 3.5 Baths
  • 2,173 Sq Ft

  208 Brewer Ave, Winter Park, FL 32789

  SELLERS ARE OFFERING A $5,000 CREDIT TO A BUYER FOR AN ACCEPTED CONTRACT BY 09/30/25! Welcome to this beautifully updated 4-bedroom, 3.5-bath Craftsman-style home, offering just under 2,200 sq ft of thoughtfully designed living space. From the moment you arrive, the charm is undeniable—with classic architectural details and a welcoming front porch that set the tone for what’s inside. Step into an

  Cassandra King COMPASS FLORIDA LLC

  208 Brewer Ave, Winter Park, FL 32789
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  /58

  $4,850 per month

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft
  • Condo for Rent

  104 S Interlachen Ave Unit 114, Winter Park, FL 32789

  Welcome to the Cloisters, an exclusive lakefront condominium community in Winter Park, now available for lease. This first-floor two-bedroom, two-bath residence offers a thoughtfully updated open-concept layout and direct garden access. Entering from the main hallway, you step into a welcoming interior where the kitchen sits to the right, featuring a breakfast bar that connects seamlessly to the

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  104 S Interlachen Ave Unit 114, Winter Park, FL 32789
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  /2

  $513,000 Sold Aug 22, 2025

  • 1,811 Sq Ft
  • $283/SF
  • 16 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1989

  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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  /33

  Est $489,811 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft

  2260 Shadowland Loop, Winter Park, FL 32792

  2260 Shadowland Loop, Winter Park, FL 32792
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  /28

  $469,000

  • 3 Beds
  • 2.5 Baths
  • 2,312 Sq Ft

  1330 Merrydale Way, Winter Park, FL 32792

  Welcome to Enclave at Hawks Crest! This corner-unit 3-bedroom, 2.5-bath townhome offers added privacy, extra natural light, and peaceful pond views, all in one of Winter Park’s most desirable gated communities. Built in 2021, this thoughtfully upgraded home features a custom wood-accent TV wall with LED lighting and floating console, plus a beautifully designed kitchen island with matching wood

  Marcelle Da Silva Sampaio SELECTA REALTY LLC

  1330 Merrydale Way, Winter Park, FL 32792
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  /29

  $1,218 - $2,122 per month

  Atlas at Winter Park

  1 - 3 Beds

  3733 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to Atlas at Winter Park!

  3733 N Goldenrod Rd, Winter Park, FL 32792
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  /2

  $1,277,000 Sold Aug 22, 2025

  • 2,595 Sq Ft
  • $492/SF
  • 5 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2009

  2728 Eastern Pkwy, Winter Park, FL 32789

  Welcome to a truly exceptional residence nestled on a quiet, tree-lined street in one of Winter Park’s most desirable neighborhoods. This custom-built gem offers a blend of elegance, craftsmanship, and resort-style comfort, featuring 3 bedrooms, 3.5 baths, and 2,595 square feet of thoughtfully designed living space. As you enter, you'll be immediately drawn to the tranquil, resort-like ambiance

  Kevin Kelly FANNIE HILLMAN & ASSOCIATES

  2728 Eastern Pkwy, Winter Park, FL 32789
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  /2

  Est $711,189 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,416 Sq Ft

  1360 Blue Stem Ln, Winter Park, FL 32792

  1360 Blue Stem Ln, Winter Park, FL 32792
• 

  

  /26

  $204,900

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

  3370 Cedar Springs Place Unit 156, Winter Park, FL 32792

  Ideally situated just minutes from Full Sail University, UCF, and major retailers, this well-appointed 2-bedroom, 2.5-bath townhome-style condo offers both comfort and convenience. The main floor features a spacious living and dining area with a breakfast nook, a guest half bath, and updated appliances. Upstairs, you’ll find two generously sized master suites, each with its own private bathroom.

  Qing Lin SPRINGHILL PROPERTIES LLC

  3370 Cedar Springs Place Unit 156, Winter Park, FL 32792
• 

  

  /18

  $3,745 per month

  • 3 Beds
  • 2.5 Baths
  • 1,990 Sq Ft
  • House for Rent

  1636 Lawndale Cir, Winter Park, FL 32792

  This beautiful 3 bedroom, 2.5 bathroom, lakefront home on Lake Florence is located on a quiet street in Winter Park's Country Lane community near local shops, restaurants, and schools. The home features a spacious floorplan with a formal living room, dining room, and family room. Enjoy the gorgeous kitchen with beautiful cabinetry, stone countertops, and breakfast bar along with custom finishes

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  1636 Lawndale Cir, Winter Park, FL 32792
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  /2

  $449,999 Sold Aug 22, 2025

  • 1,795 Sq Ft
  • $251/SF
  • 56 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1971

  7446 Houston Ct E, Winter Park, FL 32792

  The home you’ve been waiting for is here! This beautifully remodeled gem in the desirable Woodcrest neighborhood of Winter Park is move-in ready and perfect for its next owner. Featuring a sparkling private pool, this home offers modern living with style and comfort.Inside, you’ll find an open-concept floor plan ideal for entertaining and everyday living. Luxury vinyl flooring runs

  Walter Taylor KELLER WILLIAMS REALTY AT THE PARKS

  7446 Houston Ct E, Winter Park, FL 32792
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  /2

  Est $470,885 Not Listed For Sale

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

  2953 Clever Ln, Winter Park, FL 32792

  2953 Clever Ln, Winter Park, FL 32792
• 

  

  /50

  $469,000

  • 3 Beds
  • 2.5 Baths
  • 1,964 Sq Ft

  2405 Firstlight Way, Winter Park, FL 32792

  Experience refined living in the sought-after gated community of Hawks Crest. This elegant 3-bedroom, 2.5-bathroom home offers 1,964 sq ft of thoughtfully designed living space with a 2-car garage featuring a sleek epoxy finish.As you enter, natural light floods the spacious living room, highlighting the modern finishes and open layout. The gourmet kitchen is a chef’s dream—equipped with

  Carmen Acosta EXP REALTY LLC

  2405 Firstlight Way, Winter Park, FL 32792
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  /41

  $1,645 - $1,795 per month

  The Lofts of Winter Park Village

  1 Bed

  520 N Orlando Ave, Winter Park, FL 32789

  Discover urban living at its best in Winter Park's The Lofts! Offering a unique 2-level loft, the allure of high ceilings, oversized windows, and industrial touches reminiscent of New York City's ambiance. Step into the heart of the action, surrounded by Regal Movie Theatre, Crisp & Greens, Jeni's Ice Cream, Cheesecake Factory, Bar Italia, Publix, Free People, and much more. This unique urban

  520 N Orlando Ave, Winter Park, FL 32789
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  /2

  $412,500 Sold Aug 22, 2025

  • 1,349 Sq Ft
  • $306/SF
  • 57 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1957

  619 Byron Rd, Winter Park, FL 32792

  Location, lifestyle, and livability! Nestled in a prime City of Winter Park location, this beautifully landscaped, charming, freshly painted, 3-bedroom, 2-bath home offers the perfect blend of comfort and convenience—walkable to grocery stores, shopping, dining, Advent Health Winter Park Hospital, movie theater, banks and more! Inside, you’ll find a thoughtfully designed split-bedroom floor

  John Muccigrosso RE/MAX 200 REALTY

  619 Byron Rd, Winter Park, FL 32792
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  /18

  Est $200,167 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft

  3351 River View Way Unit 41, Winter Park, FL 32792

  3351 River View Way Unit 41, Winter Park, FL 32792
• 

  

  /21

  $929,900 Open Sun 11AM - 2PM

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

  2823 Wright Ave, Winter Park, FL 32789

  Here’s your chance to own something truly special in Winter Park! This gorgeous lakefront home sits on over HALF AN ACRE, a rare find in this area - allowing opportunity to BUILD YOUR DREAM HOME! Step inside to find a thoughtfully updated kitchen featuring high-end appliances, custom cabinetry, and designer finishes, ideal for both entertaining and everyday living. The home boasts new windows

  Tal Busidan TAL BUSIDAN PA

  2823 Wright Ave, Winter Park, FL 32789
• 

  

  /10

  $1,549 per month

  • 2 Beds
  • 1 Bath
  • 650 Sq Ft
  • Apartment for Rent

  1500 Michigan Ave Unit B, Winter Park, FL 32789

  This charming 2-bedroom, 1-bathroom apartment offers comfortable living space in a prime Winter Park location. Situated just around the corner from Orlando and Orange Avenues, residents enjoy easy access to downtown Orlando, Florida Hospital's main campus, I-4, and a variety of dining and entertainment options that make Winter Park one of the most desirable places to live. The home features a

  Steve Simpson 407 PROPERTIES

  1500 Michigan Ave Unit B, Winter Park, FL 32789
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  /2

  $489,020 Sold Aug 22, 2025

  • 1,260 Sq Ft
  • $388/SF
  • 61 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1925

  674 Douglas Ave, Winter Park, FL 32789

  Here is the opportunity to own this beautiful remodeled bungalow in the desirable town of Winter Park. This meticulously maintained two-bedroom, 1.5-bath home is just steps from Hannibal Square and Park Avenue. Enjoy the convenience of Rollins College, shopping, dining and vibrant nightlife, all within short distance. Enter inside this charming bungalow to discover a newly updated kitchen that

  Peter J Yates PREMIER SOTHEBYS INT'L REALTY

  674 Douglas Ave, Winter Park, FL 32789
• 

  

  /42

  Est $487,680 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  2444 Firstlight Way, Winter Park, FL 32792

  2444 Firstlight Way, Winter Park, FL 32792
• 

  

  /19

  $198,000 Open Sat 12PM - 3:30PM

  • 1 Bed
  • 1 Bath
  • 753 Sq Ft

  4768 Tangerine Ave Unit 4768, Winter Park, FL 32792

  *ALL ROOM FURNITURE IN LISTING PHOTOS CAN BE INCLUDED AS AN OPTION* Fully Renovated 1-Bedroom First-Floor Condo – Stylish & Convenient Living. Move-in ready! Gorgeous new flooring throughout, sophisticated modern lighting, freshly painted walls with contemporary baseboards and trim, impeccably styled. Welcome to 4768 Tangerine Ave #4768, a beautifully renovated one-bedroom, one-bath condo

  Christopher Franqui PROPERTY OUTLET INTERNATIONAL

  4768 Tangerine Ave Unit 4768, Winter Park, FL 32792
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  /35

  $991 - $1,737 per month

  Carlton Arms of Winter Park

  Studio - 3 Beds

  300 Jamestown Dr, Winter Park, FL 32792

  *Call or email for today’s availabilityCarlton Arms of Winter Park, a well-established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff, offers an unusual atmosphere of peaceful, private home dwelling while simultaneously assuring comforts and conveniences of apartment living.

  300 Jamestown Dr, Winter Park, FL 32792
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  /2

  $500,000 Sold Aug 22, 2025

  • 1,906 Sq Ft
  • $262/SF
  • 108 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  7584 Lodge Pole Trail, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Beautiful remodeled pool home. Luxury vinyl plank flooring throughout the entire home with tile in the bathrooms. Spacious living area with open concept floorplan. Upgraded kitchen with stainless steel appliances, granite counters, large kitchen island/bar, and closet pantry. Bathrooms both updated. Primary bathroom has large walk-in shower with

  Robert Arnold SAND DOLLAR REALTY GROUP INC

  7584 Lodge Pole Trail, Winter Park, FL 32792
• 

  /2

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  3069 Aaron Burr Ave Unit D, Winter Park, FL 32792

  3069 Aaron Burr Ave Unit D, Winter Park, FL 32792
• 

  

  /21

  $519,990

  • 2 Beds
  • 1.5 Baths
  • 1,107 Sq Ft

  1409 Sunset Dr, Winter Park, FL 32789

  This cozy 2 bedroom 1.5 bathroom home is nestled in the heart of Winter Park, surrounded by a picturesque brick street that's lined up with beautiful homes. The property has been thoughtfully renovated. The home seamlessly blends modern comforts with preserved character which include the gorgeous historic hardwood floors and a beautiful gothic cathedral window in the main bath. For the Newly

  Ahmad Karain R MICHAELS REALTY LLC

  1409 Sunset Dr, Winter Park, FL 32789
• 

  

  /16

  $2,785 per month

  • 4 Beds
  • 2.5 Baths
  • 1,970 Sq Ft
  • House for Rent

  2843 Riddle Dr, Winter Park, FL 32789

  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

  2843 Riddle Dr, Winter Park, FL 32789
• 

  /2

  $440,000 Sold Aug 22, 2025

  • 1,662 Sq Ft
  • $265/SF
  • 98 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1953

  3019 Northwood Blvd, Winter Park, FL 32789

  WINTER PARK 32789 - Mid Century design. Unique neighborhood - walk to shopping, restaurants, entertainment. 3/1.5 Bath with large Florida Room. 2 Car Carport.

  Robert Arnold SAND DOLLAR REALTY GROUP INC

  3019 Northwood Blvd, Winter Park, FL 32789
• 

  /2

  Est $223,208 Not Listed For Sale

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

  200 Saint Andrews Blvd Unit 3610, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 3610, Winter Park, FL 32792

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