Winter Park, FL Homes

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  /54

  $1,395,000

  • 4 Beds
  • 3.5 Baths
  • 3,153 Sq Ft

  2922 Reef Knot Place, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Stunning Lakefront Living in an Exclusive Gated Community! Welcome to this beautifully appointed single-level home in an intimate gated community of just 28 residences nestled along the shores of picturesque skiable Lake Florence. With direct lake frontage and access to a nearby community dock, this property offers serene water views and an

  Ellen Bessette CHARLES RUTENBERG REALTY ORLANDO

  2922 Reef Knot Place, Winter Park, FL 32792
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  /33

  $1,200 per month

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

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

  50% off the first month of rent!Enjoy this 1 bedroom 1 bathroom condo located at The Colonies in Winter Park. Close to UCF, Full Sail University and centrally located to shopping malls, major highways, restaurants and theme parks. Just 11 minutes from Orlando international Airport. This cozy 1 bedroom is perfect for a quick access to all that Orlando has. New carpet and a clean fresh

  Kristen Ackley ACKLEY FLORIDA PROPERTY MANAGEMENT INC

  3069 Aaron Burr Ave Unit D, Winter Park, FL 32792
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  /2

  $569,000 Sold May 30, 2025

  • 1,642 Sq Ft
  • $347/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1952

  1368 Devon Rd, Winter Park, FL 32789

  Welcome home to timeless beauty in the heart of highly sought-after ORWIN MANOR! Imagine living the Winter Park lifestyle where you can stroll to Foxtail Coffee, Publix, Einstein Bagels and other establishments. Jump in the car and you're just minutes from well-known Park Avenue which offers the perfect blend of charm and sophistication—with its tree-lined streets, boutique shopping, art

  Karen Ripperger LPT REALTY, LLC

  1368 Devon Rd, Winter Park, FL 32789
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  /64

  Est $1,195,445 Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 5,021 Sq Ft

  3708 Vinsetta Ct, Winter Park, FL 32792

  3708 Vinsetta Ct, Winter Park, FL 32792
• 

  

  

  /24

  $127,000

  • 2 Beds
  • 2 Baths
  • 1,066 Sq Ft

  3057 Aaron Burr Ave Unit 2, Winter Park, FL 32792

  Welcome to 3057 Aaron Burr Ave #2, a beautifully updated 2-bedroom, 2-bathroom condo in the desirable Colonies community. Whether you're looking for a stylish home or a fantastic investment opportunity, this property checks all the boxes!Step inside to find brand-new stainless-steel appliances, granite countertops, and spacious walk-in closets. The open layout creates a bright and inviting

  Claudia Villarroel ROBERT SLACK LLC

  3057 Aaron Burr Ave Unit 2, Winter Park, FL 32792
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  /15

  $1,995 per month

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Apartment for Rent

  1055 S Kentucky Ave Unit 4, Winter Park, FL 32789

  Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and dining room with Kitchen complete with all appliances included and great counter space. The first bedroom has a nice space with a walking closet. The master bedroom is spacious and bright with a large walk-in closet that also leads into the private bathroom! Bathrooms are very

  Valentina Rodriguez LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  1055 S Kentucky Ave Unit 4, Winter Park, FL 32789
• 

  /2

  $243,800 Sold May 30, 2025

  • 960 Sq Ft
  • $254/SF
  • 24 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1984

  255 Sandlewood Trail, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Dreams Do Come True! FHA, VA, and DPA approved, making it a smart choice for a wide range of buyers. Welcome to your next home in the heart of 32789—Winter Park’s hidden gem, Sandlewood Creek! This rare townhome-style condo offers unbeatable value in a prime location with NO neighbors above or below and a LOW HOA.Step inside and enjoy nearly 1,000

  Freddie Crespo INVESTOR'S REAL ESTATE LLC

  255 Sandlewood Trail, Winter Park, FL 32789
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  /46

  Est $2,252,518 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,286 Sq Ft

  660 W Morse Blvd, Winter Park, FL 32789

  660 W Morse Blvd, Winter Park, FL 32789
• 

  

  /25

  $449,999 Open Sun 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 1,795 Sq Ft

  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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  /13

  $1,995 per month

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Apartment for Rent

  1055 S Kentucky Ave Unit 2, Winter Park, FL 32789

  Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and dining room with Kitchen complete with all appliances included and great counter space. The first bedroom has a nice space with a walking closet. The master bedroom is spacious and bright with a large walk-in closet that also leads into the private bathroom! Bathrooms are very

  Valentina Rodriguez LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  1055 S Kentucky Ave Unit 2, Winter Park, FL 32789
• 

  /2

  $410,000 Sold May 30, 2025

  • 1,570 Sq Ft
  • $261/SF
  • 13 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1957

  1840 Maywood Rd, Winter Park, FL 32792

  Welcome to this beautifully updated four-bedroom, two-bath mid-century block home under the canopy of a majestic oak tree in the heart of Winter Park. From the moment you arrive, you’ll appreciate the inviting curb appeal, enhanced by fresh exterior paint, modern geometric accents and a wide driveway with covered parking. Step inside to find a sun-soaked living room with vaulted ceilings and

  Nancy Merriam PREMIER SOTHEBY'S INTL. REALTY

  1840 Maywood Rd, Winter Park, FL 32792
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  /29

  Est $512,250 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,468 Sq Ft

  1114 Washington Ave Unit 3, Winter Park, FL 32789

  1114 Washington Ave Unit 3, Winter Park, FL 32789
• 

  

  /39

  $2,399,000

  • 3 Beds
  • 4 Baths
  • 3,440 Sq Ft

  922 N Pennsylvania Ave, Winter Park, FL 32789

  Experience timeless elegance and modern sophistication in this stunning 3 bedroom, 4 bath Mediterranean home, ideally situated on the 4th hole of the beautifully maintained Winter Park 9-hole golf course. Nestled on a 75 x 100 lot, this 3,440 sq ft residence was extensively renovated in 2017. From the moment you enter the welcoming foyer you'll notice the refined finishes and intentional design.

  Megan Cross FANNIE HILLMAN & ASSOCIATES

  922 N Pennsylvania Ave, Winter Park, FL 32789
• 

  

  /16

  $1,995 per month

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Apartment for Rent

  1055 S Kentucky Ave Unit 1, Winter Park, FL 32789

  Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and dining room with Kitchen complete with all appliances included and great counter space. The first bedroom has a nice space with a walking closet. The master bedroom is spacious and bright with a large walk-in closet that also leads into the private bathroom! Bathrooms are very

  Valentina Rodriguez LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  1055 S Kentucky Ave Unit 1, Winter Park, FL 32789
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  /2

  $650,000 Sold May 30, 2025

  • 2,002 Sq Ft
  • $325/SF
  • 79 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2019

  1219 Verdant Glade Place, Winter Park, FL 32792

  Welcome to this stunning two-story, 3-bedroom, 3 and a half bathroom home, nestled within the highly desirable Winter Park in a secure gated community. This kitchen boasts luxury features including quartz countertops, stainless steel appliances and rich dark wood cabinets. The master bedroom, with a spacious bathroom and walk-in closet, is conveniently located downstairs for added convenience.

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  1219 Verdant Glade Place, Winter Park, FL 32792
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  /25

  Est $300,488 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,565 Sq Ft

  7481 Swallow Run Unit GE, Winter Park, FL 32792

  7481 Swallow Run Unit GE, Winter Park, FL 32792
• 

  

  /70

  $2,490,000

  • 3 Beds
  • 3.5 Baths
  • 2,709 Sq Ft

  1602 Alabama Dr Unit 404, Winter Park, FL 32789

  A Jewel Box: Curated for a Life Well Lived. Penthouse 404 at The Alabama is a rare architectural gem—a two-story residence that blends historic provenance w/ design-forward luxury in the heart of Winter Park’s most coveted lakefront setting. Created by combining two original top-floor units, this expansive penthouse is the largest in the building & the only one w/ a private outdoor terrace.

  Padgett McCormick KELLY PRICE & COMPANY LLC

  1602 Alabama Dr Unit 404, Winter Park, FL 32789
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  /7

  $1,450 per month

  • 1 Bed
  • 1 Bath
  • 960 Sq Ft
  • Townhouse for Rent

  1512 Indiana Ave Unit B, Winter Park, FL 32789

  Spacious ONE BEDROOM , one bath CONDO available now! This is a first floor apartment with a spacious living room and dining room and Kitchen complete with all appliances included and great counter space. The master bedroom is spacious and bright with a large walk-in closet that also leads into the bathroom! Bathroom with shower. Washer and dryer combo included! Just a mile away from the amazing

  Valentina Rodriguez LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  1512 Indiana Ave Unit B, Winter Park, FL 32789
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  /2

  $230,000 Sold May 30, 2025

  • 1,026 Sq Ft
  • $224/SF
  • 75 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  1500 Gay Rd Unit 10C, Winter Park, FL 32789

  Waterfront Community on beautiful Lake Killarney. Enjoy breathtaking sunsets on Community deck! Private Boat Ramp on this Skiable Lake, limited Boat parking on property. 2 Bedroom 2 Bath second floor Unit has been meticulously maintained by Winter Resident. Furniture purchased in 2020. Many Updates to Unit include new windows and window treatments, 2024 new Hot Water Heater, Baths redone in

  Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 10C, Winter Park, FL 32789
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  /24

  Est $147,371 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,035 Sq Ft

  3054 George Mason Ave Unit 8, Winter Park, FL 32792

  3054 George Mason Ave Unit 8, Winter Park, FL 32792
• 

  

  /43

  $610,000

  • 3 Beds
  • 2 Baths
  • 1,875 Sq Ft

  151 N Orlando Ave Unit 212, Winter Park, FL 32789

  Experience luxury lakefront living in this stunning and truly unique 3-bedroom, 2-bathroom second-floor condo. This expansive 1,875 SF residence blends modern European design with artistic detail. Designed by a local artist in collaboration with a local architect, every element of this home reflects thoughtful craftsmanship and sophistication. The condo features newer plumbing, electrical wiring,

  Brian Hyser THE AGENCY ORLANDO

  151 N Orlando Ave Unit 212, Winter Park, FL 32789
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  /13

  $1,600 per month

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Townhouse for Rent

  7437 Belle River Ct Unit 7, Winter Park, FL 32792

  wonderful 2BR/21/2 bath in the wonderful city of Winter Park. Spacious master bedroom upstairs with its own private bath, along with the second bedroom and its own en suite bathroom. Relaxation can continue outside on your private fenced in patio. Enjoy plenty of storage space as this unit includes an outdoor storage room and additional storage space located under the stairs. Near to Orlando

  Altagracia Concepcion TRANSCONTINENTAL REALTY GROUP,

  7437 Belle River Ct Unit 7, Winter Park, FL 32792
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  /2

  $400,000 Sold May 29, 2025

  • 1,467 Sq Ft
  • $273/SF
  • 36 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  5144 Goldenrod Place Rd, Winter Park, FL 32792

  Great Opportunity. Nestled on an oversized lot at the end of a peaceful cul-de-sac, this charming home offers the perfect blend of privacy and comfort. The spacious feel of the location provides a serene and tranquil setting, making it the ideal place to relax and unwind on your huge Patio overlooking wonderful backyard ! As you step inside, the warm and cozy atmosphere welcomes you. The home's

  Rebecca Sparks C. APOLLO REALTY INC

  5144 Goldenrod Place Rd, Winter Park, FL 32792
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  /14

  Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 1,470 Sq Ft

  171 Stefanik Rd, Winter Park, FL 32792

  171 Stefanik Rd, Winter Park, FL 32792
• 

  

  /18

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,613 Sq Ft

  5559 Pats Point, Winter Park, FL 32792

  Not often does a home come available in this SMALL, SOUGHT AFTER COMMUNITY in WINTER PARK, located on a dead-end street with low HOA. Step inside and notice the OPEN FLOOR PLAN with 2 LARGE LIVING AREAS, TILE FLOORS and SPLIT BEDROOM PLAN for your privacy. The kitchen is the heart of the home and offers WOOD CABINETS, CLOSET PANTRY, BREAKFAST BAR, and STAINLESS APPLIANCES plus it's open to the

  Renee Killiri RED BIRD REALTY OF FLORIDA INC

  5559 Pats Point, Winter Park, FL 32792
• 

  

  /14

  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit C103, Winter Park, FL 32789

  Charming condo for Lease! location , Location , location ! This 2-bedroom, 1-bathroom apartment offers an open layout with plenty of natural light, a spacious living area, and a well-equipped kitchen with brand new interior paint job.Enjoy the convenience of in-unit laundry and modern amenities throughout. The apartment is situated in a serene community, offering easy access to shopping, dining,

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit C103, Winter Park, FL 32789
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  /2

  $450,000 Sold May 29, 2025

  • 1,672 Sq Ft
  • $269/SF
  • 26 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1956

  1807 Yorkshire Dr, Winter Park, FL 32792

  Ready to demo and BUILD NEW or completely reimagine your dream home in beautiful Winter Park??!! Look no further - this is a large .23 acre lot. Minutes to top Winter Park schools, the WP YMCA, Winter Park Racquet Club, Interlachen Country Club, shopping, dining and other conveniences and surrounded by beautiful mid-century and luxury homes. This home has 3 bedrooms plus 2 bonus rooms that would

  Carla Stanton MAINFRAME REAL ESTATE

  1807 Yorkshire Dr, Winter Park, FL 32792
• 

  

  /17

  Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,128 Sq Ft

  110 Stefanik Rd, Winter Park, FL 32792

  110 Stefanik Rd, Winter Park, FL 32792
• 

  

  /36

  $355,000

  • 3 Beds
  • 2.5 Baths
  • 1,406 Sq Ft

  3118 Crown Jewel Ct, Winter Park, FL 32792

  Come to see this beautiful townhouse blends functionality with upscale finishes, a prime location ideal for families, or professionals looking for style and convenience. This home boasts numerous upgrades for both comfort and style. PAVER DRIVEWAY is designed for two cars to park, and architectural appeal adds curb appeal. SCREENED-IN LANAIS with upgraded ceiling light fans, no rear neighbors,

  Xue Gao U KEY REALTY

  3118 Crown Jewel Ct, Winter Park, FL 32792
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  /28

  $1,499 per month

  • 2 Beds
  • 2 Baths
  • 1,049 Sq Ft
  • Condo for Rent

  1000 S Semoran Blvd Unit 816, Winter Park, FL 32792

  Charming 2-Bedroom, 2-Bathroom Condo in Winter Park – Move-In Ready!This lovely second-floor unit in Golfside Villas features brand-new carpet installed in 2025! Step into a spacious, open-concept kitchen and living area, offering a comfortable and inviting space to relax and entertain.The master bedroom includes an en-suite bathroom, while the generously sized second bedroom also boasts new

  Yuly Rodriguez DOUGLAS EDMUND REAL ESTATE LLC

  1000 S Semoran Blvd Unit 816, Winter Park, FL 32792
• 

  /2

  $421,700 Sold May 29, 2025

  • 1,525 Sq Ft
  • $277/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  1189 Lazy Hollow Place, Winter Park, FL 32792

  Welcome to this meticulously updated and **FULLY FENCED POOL HOME**, reflecting exceptional pride in ownership and featuring numerous thoughtful upgrades, all nestled in the desirable Winter Park area with **NO HOA** and a **NEW METAL ROOF (2022) ** This home is ideally situated on a **QUIET CUL-DE-SAC**, offering additional privacy and tranquility. The **SOLID BLOCK CONSTRUCTION** ensures

  Virginia Silberstein ORLANDO EXPERT REALTY LLC

  1189 Lazy Hollow Place, Winter Park, FL 32792
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  /3

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,128 Sq Ft

  100 Stefanik Rd, Winter Park, FL 32792

  100 Stefanik Rd, Winter Park, FL 32792
• 

  

  /22

  $300,000 Open Sun 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft

  2376 Dominica Run, Winter Park, FL 32792

  Welcome to this beautifully updated townhouse located in the heart of desirable Winter Park! Step inside to find a bright and inviting interior featuring tile and vinyl flooring throughout—offering both style and easy maintenance. The newly renovated kitchen is a true showstopper, complete with stunning white quartz countertops, sleek new cabinetry, modern appliances, and a classic farmhouse sink

  Natasha Myers MARK SPAIN REAL ESTATE

  2376 Dominica Run, Winter Park, FL 32792
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  /32

  $2,500 per month

  • 2 Beds
  • 1 Bath
  • 1,032 Sq Ft
  • House for Rent

  626 Baffie Ave, Winter Park, FL 32789

  Great location, very near I-4 access just off Fairbanks in College Park/Winter Park. Oversized paver driveway and parking area. 2 bedrooms with one bathroom, and an extra room that could be used as an office. Bathroom has shower/tub combination, Home was built in 1938 and is charming and well maintained. Large screen porch with ceiling fans covers the entire front of the house. Home has

  Kathleen Penkacik GRACE REALTY, INC.

  626 Baffie Ave, Winter Park, FL 32789
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  /45

  $1,100,000 Sold May 29, 2025

  • 2,786 Sq Ft
  • $395/SF
  • 130 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1960

  708 Balmoral Rd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Welcome to 708 Balmoral Road, located in the desirable heart of Winter Park. This charming single-story home boasts 4 bedrooms, 3 baths, and a generous 2786 sq. ft. of living space on a sprawling, elevated 15,161 sq. ft. corner lot. The spacious and open floor plan features soaring beams in many rooms, adding to the home's character and warmth.The

  Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  708 Balmoral Rd, Winter Park, FL 32789
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  /17

  Est $317,791 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,554 Sq Ft

  2644 Passamonte Dr Unit 7C, Winter Park, FL 32792

  2644 Passamonte Dr Unit 7C, Winter Park, FL 32792
• 

  

  /48

  $3,190,000

  • 5 Beds
  • 5.5 Baths
  • 4,263 Sq Ft

  1820 Englewood Rd, Winter Park, FL 32789

  Award-winning Phil Kean design on a prominent corner lot in the heart of Winter Park, just minutes from Baldwin Park, Park Avenue, and East End Market—home to Michelin-rated dining and upscale retail. This 5-bed, 5.5-bath residence delivers clean lines, smart design, and seamless indoor-outdoor flow. Recognized with multiple honors, including the 2015 Parade of Homes 1st Place Award for Custom

  David Hung KELLER WILLIAMS ADVANTAGE III

  1820 Englewood Rd, Winter Park, FL 32789
• 

  

  /17

  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit E115, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove with 3 bedrooms and 2 bathrooms is a great opportunity to own in Winter Park, close to major highways, shopping, restaurants and so much more. This unit is perfect for lease , brand new paint and flooring ! RENOVATED BATHROOMS! The open living room is spacious and has lots of natural light shining in from the sliding glass doors leading out to the

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit E115, Winter Park, FL 32789
• 

  /2

  $4,599,000 Sold May 28, 2025

  • 3,660 Sq Ft
  • $1257/SF
  • 0 Days On Market

  • 5 Beds
  • 7 Baths
  • Built 1951

  985 Lincoln Cir, Winter Park, FL 32789

  Welcome to Lincoln! This new construction single family home has been meticulously crafted and constructed by Wooten Built, a locally established, award-winning developer and luxury home Builder. Location! Location! Location! Lincoln Circle is a quiet street next to Park Avenue restaurants and shopping. Easily walk to Winter Park shops, restaurants, and the Winter Park Golf Course. This bespoke

  Clay Wooten UNITED REAL ESTATE PREFERRED

  985 Lincoln Cir, Winter Park, FL 32789
• 

  

  /24

  Est $667,490 Not Listed For Sale

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

  5303 Pine Lily Cir, Winter Park, FL 32792

  5303 Pine Lily Cir, Winter Park, FL 32792

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