Winter Park, FL Homes

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  /26

  $163,000

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft

  141 Lewfield Cir Unit 141, Winter Park, FL 32792

  Renovated and the only first floor one-bedroom, one-bath beautiful condominium available and in a great interior location in the complex! Conveniently near various amenities, including a short walk across the street to Publix, TJ Maxx, shops and restaurants. Welcome home to this delightful open floor plan that optimizes the space, featuring a newer kitchen with a pass-through flowing into the

  Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

  141 Lewfield Cir Unit 141, Winter Park, FL 32792
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  /16

  $2,700 per month

  • 3 Beds
  • 2 Baths
  • Condo for Rent

  2500 Euston Rd, Winter Park, FL 32789

  Property Id: 2001904This property has a wide range of options available for residents that are looking for a balance of price, quality and location!

  2500 Euston Rd, Winter Park, FL 32789
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  /2

  $385,000 Sold Jun 11, 2025

  • 1,262 Sq Ft
  • $305/SF
  • 101 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1955

  1930 Albert Lee Pkwy, Winter Park, FL 32789

  Tucked away on a quiet street yet just minutes from downtown Winter Park, College Park, and downtown Orlando, this beautifully updated 1955 ranch offers the perfect blend of peaceful living and urban convenience. With 2 bedrooms, 2 baths, and 1,262 square feet of thoughtfully renovated space, this home is move-in ready and full of character. As you enter, you’re greeted by a large, open living

  Carol van den Berg FLORIDA ONE REAL ESTATE LLC

  1930 Albert Lee Pkwy, Winter Park, FL 32789
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  /2

  Est $804,491 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,094 Sq Ft

  2352 Kestrel Perch Place, Winter Park, FL 32792

  2352 Kestrel Perch Place, Winter Park, FL 32792
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  /99

  $6,180,000

  • 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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  /15

  $2,550 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • House for Rent

  2176 Crandon Ave, Winter Park, FL 32789

  Fully furnished and Turnkey/Renovated in-town home. Close to downtown Winter Park, Advent and Orlando Health.Newly renovated kitchen with Sub-Zero/Cafe appliances. Monthly rental only…2 bedrooms sleeps 4. Nice covered/screened porch. Available now. Weekly to monthly rental.

  Dan Haber CORCORAN PREMIER REALTY

  2176 Crandon Ave, Winter Park, FL 32789
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  /2

  $849,900 Sold Jun 10, 2025

  • 1,776 Sq Ft
  • $479/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1956

  1791 Spruce Ave, Winter Park, FL 32789

  Welcome to this stunning, fully renovated 3-bedroom, 2-bath residence nestled in the highly sought-after Winter Park community. Thismeticulously upgraded home blends style, comfort, and functionality in an open-concept layout that includes spacious living, dining and kitchen areas adorned with elegant wood flooring and crown molding throughout. The custom-designed kitchen is a chef’s dream,

  Betsy Breton-Garcia KELLER WILLIAMS WINTER PARK

  1791 Spruce Ave, Winter Park, FL 32789
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  /54

  Est $794,386 Not Listed For Sale

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

  1155 Wildmeadow Run, Winter Park, FL 32792

  1155 Wildmeadow Run, Winter Park, FL 32792
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  /56

  $2,800,000

  • 5 Beds
  • 5.5 Baths
  • 4,469 Sq Ft

  1341 Place Picardy, Winter Park, FL 32789

  Discover luxury living in this custom Austin Homes 5 bedroom, 5 and one half bath transitional style home that offers a blend of modern and traditional elements coupled with a highly desirable Winter Park location. This residence boasts a sought-after open floor plan with 12-foot ceilings, wide plank wood flooring and truly exceptional detailed finishes throughout. You will feel instantly at home

  Julie Bettosini STOCKWORTH REALTY GROUP

  1341 Place Picardy, Winter Park, FL 32789
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  /20

  $1,795 per month

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft
  • Condo for Rent

  160 Moyses Rd Unit 160 Moyses Road, Winter Park, FL 32792

  Property Id: 1997944Newly Remodeled Home in Winter Park! - 160 Moyses Road Winter Park, FLWelcome to this stunning 2-bedroom, 1.5-bathroom home, nestled in a quiet cul-de-sac in the highly sought-after Winter Park area. Just remodeled, this unit features a brand-new kitchen with modern shaker-style cabinets, sparkling white granite countertops, and all-new stainless steel

  160 Moyses Rd Unit 160 Moyses Road, Winter Park, FL 32792
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  /2

  $450,000 Sold Jun 10, 2025

  • 1,761 Sq Ft
  • $256/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1971

  3317 Dormer Ct, Winter Park, FL 32792

  Welcome to your dream home in the heart of Central Florida! This immaculate, move-in ready 3-bedroom, 2-bath pool home is a true gem, nestled in an established neighborhood known for its top-rated schools, friendly community, and unbeatable location. Step inside to find tastefully updated living spaces that blend comfort with modern style. As you enter the foyer, you will find the formal living

  Stephanie Kovats KELLER WILLIAMS ADVANTAGE REALTY

  3317 Dormer Ct, Winter Park, FL 32792
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  /67

  Est $1,321,939 Not Listed For Sale

  • 7 Beds
  • 5 Baths
  • 5,111 Sq Ft

  1464 Via Sangro Place, Winter Park, FL 32792

  1464 Via Sangro Place, Winter Park, FL 32792
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  /59

  $1,799,000

  • 3 Beds
  • 2.5 Baths
  • 2,907 Sq Ft

  1640 Mayfield Ave, Winter Park, FL 32789

  This elegant one story home is located in highly desirable Winter Park on an oversized .28 acre lot with mature and lush landscaping and NO HOA. It has 10' ceilings and an open floor plan combining kitchen, dining, and living rooms with gorgeous wood floors and plenty of natural light overlooking the secluded & screened salt water pool with cascading water features, gas heated spa, and covered

  Beverly Brown RE/MAX PRIME PROPERTIES

  1640 Mayfield Ave, Winter Park, FL 32789
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  /11

  $1,675 per month

  • 2 Beds
  • 1.5 Baths
  • 1,085 Sq Ft
  • Condo for Rent

  300 Scottsdale Square Unit 300, Winter Park, FL 32792

  Spacious two-story condo located on the second floor, now available for rent! This well-maintained unit features ceramic tile flooring throughout, with carpeted stairs, and offers a bright, open layout. Conveniently situated near major highways and popular restaurants, it's perfect for commuters and those who enjoy easy access to dining and entertainment. Move-in ready—schedule your viewing today!

  Johany Utrera AVID REALTY LLC

  300 Scottsdale Square Unit 300, Winter Park, FL 32792
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  /2

  $415,000 Sold Jun 10, 2025

  • 1,673 Sq Ft
  • $248/SF
  • 23 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  3063 Ash Park Loop, Winter Park, FL 32792

  Location, Location, Location! Welcome to Hyde Park! This lovely home in Winter Park offers a blend of amenities and classic charm. The home boasts an open layout, creating spacious living which is great for entertaining and everyday living. A cozy wood-burning fireplace adds warmth and charm to the living space. New roof installed in 2018, new HVAC system in 2022, freshly painted exterior and

  Cheryl Anderson ANDERSON INVESTMENT PROPERTIES

  3063 Ash Park Loop, Winter Park, FL 32792
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  /28

  Est $472,461 Not Listed For Sale

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

  2901 Clever Ln, Winter Park, FL 32792

  2901 Clever Ln, Winter Park, FL 32792
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  /4

  $3,960,000

  • Land
  • 1.81 Acres
  • $2,187,845 per Acre

  0 Aloma Ave, Winter Park, FL 32789

  Entire 1.81 (+/-) acre platted subdivision for sale. Total of 7 lots in desirable 32789 city of Winter Park. Six lots are zoned for residential use and one is currently zoned for office use. Link to recorded plat and HOA information available upon request.

  Ruth Ryan RUTH PRITCHARD RYAN

  0 Aloma Ave, Winter Park, FL 32789
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  /20

  $1,795 per month

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft
  • Condo for Rent

  2667 Rook Cove Unit 2667 Rook Cove, Winter Park, FL 32792

  Property Id: 1997988Newly Remodeled Home in the Heart of Winter Park! - 2667 Rook Cove, Winter Park, FLWelcome to this stunning 2-bedroom, 1.5-bathroom home, nestled in a quiet cul-de-sac in the highly sought-after Winter Park area. Just remodeled, this unit features a brand-new kitchen with modern shaker-style cabinets, sparkling white granite countertops, and all-new stainless

  2667 Rook Cove Unit 2667 Rook Cove, Winter Park, FL 32792
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  /2

  $987,500 Sold Jun 10, 2025

  • 2,220 Sq Ft
  • $445/SF
  • 101 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1959

  1585 Chestnut Ave, Winter Park, FL 32789

  Charming Spanish-Style Bungalow with Private Oasis in the Heart of Winter Park. Step into the elegance of Old Florida with this exquisite Spanish-style bungalow, nestled in Winter Park. Offering the perfect blend of historic charm and modern luxury, this 4-bedroom, 2.5-bath retreat is a hidden gem surrounded by lush, mature landscaping, creating a private sanctuary just minutes from the best

  Ashley Landers KELLER WILLIAMS WINTER PARK

  1585 Chestnut Ave, Winter Park, FL 32789
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  /32

  Est $693,772 Not Listed For Sale

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

  1431 Lake Florence Way, Winter Park, FL 32792

  1431 Lake Florence Way, Winter Park, FL 32792
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  /46

  $150,000

  • 1 Bed
  • 1 Bath
  • 793 Sq Ft

  200 St Andrews Blvd Unit 911, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Here is an amazing 1-bedroom, 1-bath condo in Winter Park's beautiful Four Seasons. It's on the 2nd floor, so you won't have to worry about noisy neighbors above you! The garden views are lovely, and it has a huge walk-in closet along with really spacious rooms. Plus, there's a nice screened balcony that's perfect for those cool summer nights.This

  Jonathan Lacko WINTER PARK REAL ESTATE CO LLC

  200 St Andrews Blvd Unit 911, Winter Park, FL 32792
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  /2

  $1,500 per month

  • House for Rent

  987 Cherokee Ave, Winter Park, FL 32789

  The landlord seeks a long term tenant or a joint venture from a developer or someone with a home to move.Contact us now and let's discuss this opportunity. Vacant LandIncredible opportunity to bring your own home to this prime Winter Park building lot with all utilities stubbed at the curb from a previous home that was removed. The current owner of 987 Cherokee Avenue, Winter Park is willing to

  John R. Gordon EXP REALTY LLC

  987 Cherokee Ave, Winter Park, FL 32789
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  /2

  $750,000 Sold Jun 09, 2025

  • 1,740 Sq Ft
  • $431/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1967

  2756 Summerfield Rd, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Outstanding opportunity to be in one of the best neighborhoods, as well as golf holes, of the Winter Park Pines Golf Course and community of Golfside! Discover the perfect blend of comfort, style, and location in this beautifully updated Mid-Century Modern 3-bedroom, 2-bath home nestled on the lush fairway of the 9th hole (formerly the 18th hole.)

  Alexis Davis FANNIE HILLMAN & ASSOCIATES

  2756 Summerfield Rd, Winter Park, FL 32792
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  /14

  Est $739,877 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,851 Sq Ft

  1407 Miller Ave, Winter Park, FL 32789

  1407 Miller Ave, Winter Park, FL 32789
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  /28

  $450,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,806 Sq Ft

  2151 Conifer Ave, Winter Park, FL 32792

  This POOL home is amazing in every way and is truly a must see! Original Owner with pride of ownership. Nestled in the highly coveted community of Eastbrook in Winter Park. A perfect location just minutes to everything. This residence boasts an array of desirable features. Three bedrooms and two full baths with oversized primary bedroom. As you enter through the new, striking front door and

  Denise Korrey KORR REALTY CORP

  2151 Conifer Ave, Winter Park, FL 32792
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  /7

  $2,000 per month

  • 2 Beds
  • 1 Bath
  • House for Rent

  1399 Miller Ave, Winter Park, FL 32789

  Property Id: 1795045Charming 1926 bungalow. 2 bedroom/1 bathroom house in prime location of Winter Park. Wood floors throughout the home, cast iron bathtub, hexagon tile in bathroom. Short drive to I-4, Park Ave, Rollins College, shopping, restaurants, downtown Orlando, hospitals, and more. Extra large front porch, fireplace, full kitchen, and washer and dryer.Renter responsible

  1399 Miller Ave, Winter Park, FL 32789
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  /2

  $586,000 Sold Jun 09, 2025

  • 1,630 Sq Ft
  • $360/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  2441 Banchory Rd, Winter Park, FL 32792

  Welcome to this beautifully renovated 3-bedroom, 2-bathroom home in the highly desirable Brookshire Heights neighborhood! Nestled on the charming, tree-lined Banchory Road with sidewalks on both sides, this home is just a short stroll from Brookshire Elementary, the Cady Way Pool, Pickleball Courts, and Trail.In 2018, this home underwent extensive renovations, including a new roof, HVAC system,

  Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  2441 Banchory Rd, Winter Park, FL 32792
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  /38

  Est $318,754 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft

  236 Balfour Dr Unit 21, Winter Park, FL 32792

  236 Balfour Dr Unit 21, Winter Park, FL 32792
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  /44

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,771 Sq Ft

  212 Blossom Ln, Winter Park, FL 32789

  Welcome to this beautiful home in highly sought-after Winter Park! This 3 bedroom 2 bath home in the desirable Shores of Lake Killarney will capture your attention for sure. It is well maintained and immaculately kept. Kitchen has plenty of cabinet and counter space, granite counter tops and tiled backsplash. The screened patio is cedar with stone flooring and has plenty of space to entertain!

  Michele Pietrowski BHHS FLORIDA REALTY

  212 Blossom Ln, Winter Park, FL 32789
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  /16

  $1,450 per month

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

  1500 Gay Rd Unit 5C, Winter Park, FL 32789

  Welcome to Winter Park, FL! This charming one-bedroom, one-bathroom apartment is perfectly situated close to shopping and dining options, making it an ideal location for those seeking convenience. The community offers a refreshing pool where you can relax and unwind, and the lawn care service ensures a well-maintained and picturesque environment. With laundry facilities conveniently located

  Jacob Hara TRANSCEND REALTY

  1500 Gay Rd Unit 5C, Winter Park, FL 32789
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  /2

  $420,000 Sold Jun 09, 2025

  • 1,551 Sq Ft
  • $271/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1969

  2259 King Johns Ct, Winter Park, FL 32792

  Don’t miss this beautifully maintained, move-in ready 3-bedroom, 2-bath gem in the highly desirable Winter Park area — and best of all, there’s no HOA!Step into the updated kitchen, complete with solid wood cabinetry, granite countertops, stainless steel appliances, and a wine fridge — perfect for cooking and entertaining. The kitchen seamlessly flows into a spacious great room, where sliding

  Richard Cunningham CHARLES RUTENBERG REALTY ORLANDO

  2259 King Johns Ct, Winter Park, FL 32792
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  /29

  Est $349,809 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft

  3113 Crown Jewel Ct, Winter Park, FL 32792

  3113 Crown Jewel Ct, Winter Park, FL 32792
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  /40

  $1,675,000

  • 4 Beds
  • 5 Baths
  • 3,478 Sq Ft

  1350 Lyndale Blvd, Winter Park, FL 32789

  THIS HOUSE CHECKS ALL OF THE BOXES!!!Situated on a quiet one-way street in Winter Park and recently renovated is this 4 bed, 3 full 2 half bath home built with style and elegance. From the 10’ ceilings to Brazilian cherry floors, a gourmet kitchen, screened pool and generous bonus room above the oversized garage with tons of storage, this home has it all. The impressive gourmet

  Carol Wittman PALMANO GROUP RE BROKERAGE LLC

  1350 Lyndale Blvd, Winter Park, FL 32789
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  /20

  $6,000 per month

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  860 N Denning Dr, Winter Park, FL 32789

  AVAILABLE NOW !! 30 Day minimum! Fully furnished all utilities included and high speed internet !! You can't beat it!! NEW CONSTRUCTION Luxury Home north of Downtown Orlando in the heart of Winter Park steps from Winter Park Village near the Famous Park Ave where you'll find unlimited entertainment choices including dining, shopping, nightlife, axe throwing etc You WILL LOVE this custom home!! NO

  860 N Denning Dr, Winter Park, FL 32789
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  /2

  $170,000 Sold Jun 09, 2025

  • 1,031 Sq Ft
  • $165/SF
  • 53 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1984

  3208 Oak Lawn Place Unit 218, Winter Park, FL 32792

  Experience the perfect blend of charm, convenience, and value in this beautifully maintained (freshly cleaned and painted) 2-bed, 2.5-bath townhouse-style condo nestled in the heart of the desirable Hidden Oaks community in Winter Park. Whether you're a first-time homebuyer, a savvy investor, or simply seeking a cozy space to call home, this property is a standout choice. Key Features Include:

  Ali Khaku, MBA DALTON WADE INC

  3208 Oak Lawn Place Unit 218, Winter Park, FL 32792
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  /11

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,851 Sq Ft

  1405 Miller Ave, Winter Park, FL 32789

  1405 Miller Ave, Winter Park, FL 32789
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  /45

  $1,850,000 Open Sun 12PM - 3PM

  • 5 Beds
  • 5.5 Baths
  • 4,155 Sq Ft

  1355 Hibiscus Ave, Winter Park, FL 32789

  Welcome to this beautifully crafted 5 bedroom, 5.1 bathroom traditional single-family home offering over 4,100 SF of living space. Ideally located on a tree-lined street with Winter Park’s signature brick roads, this home sits in one of the area’s most sought-after neighborhoods. Just minutes from the Winter Park Racquet Club in the Vias, Park Avenue shops and dining, YMCA, top hospitals, and

  Nadia Moayeri PALMANO GROUP RE BROKERAGE LLC

  1355 Hibiscus Ave, Winter Park, FL 32789
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  /24

  $2,850 per month

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft
  • Townhouse for Rent

  1504 Broad Wing Ln, Winter Park, FL 32792

  This is one of the best townhome lots available in Hawks Crest, the highly desired community in Winter Park! No rear neighbors and a beautiful conservation view! This 3-bed 2.5 bath townhome is move-in ready on May 1st. A long driveway welcomes you home after a busy day. When you enter the home, a high ceiling entry with 4 sliding doors to the back patio gives you plenty of natural sunlight. The

  Jaime Hernandez INTOP PROPERTY MANAGEMENT

  1504 Broad Wing Ln, Winter Park, FL 32792
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  /2

  $750,000 Sold Jun 09, 2025

  • 2,503 Sq Ft
  • $300/SF
  • 284 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1980

  2804 Dike Rd, Winter Park, FL 32792

  Welcome to your very own private personal retreat! This truly one of a kind oasis of a property features 1.9 acres of lushly landscaped garden in Winter Park. A four-bedroom, three-bathroom main house with a two-car attached garage and a luxurious pool. With paid-for solar panels and a 37 seer Geo-Thermal HVAC means you will enjoy significant savings on your power bills. The additional detached

  Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

  2804 Dike Rd, Winter Park, FL 32792
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  /19

  Est $276,609 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 939 Sq Ft

  2404 Gallery View Dr Unit 1, Winter Park, FL 32792

  2404 Gallery View Dr Unit 1, Winter Park, FL 32792

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