Winter Park, FL 1-Story Homes for Sale

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  /18

  $1,999,999

  • 4,056 Sq Ft

  1903 S Lakemont Ave, Winter Park, FL 32792

  Location, location, location! This is an amazing opportunity to build/renovate on a premier lakefront lot in the charming and upscale Winter Park neighborhood of Orlando, Florida. Located on Lake Spier and across the street from the beautiful Baldwin Park, this exceptional-almost one acre property-includes six 1/1 units. This prime property is minutes from award winning restaurants, sidewalk

  Maria Tenner Platinum Properties Int'l Inc.

  1903 S Lakemont Ave, Winter Park, FL 32792
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  /53

  $241,900

  • 2 Beds
  • 2 Baths
  • 1,015 Sq Ft

  200 Saint Andrews Blvd Unit 2306, Winter Park, FL 32792

  Excellent opportunity in a prime location in Central Florida. This two-bedroom, two-full-bath corner unit is in the Four Seasons Condominiums of Winter Park, just steps from the Cady Way Trail, Showalter Field, Ward Park, the YMCA, medical centers, and shopping. Park Avenue and museums are just minutes away. Four Seasons Condominiums is a 20-acre community located within the Winter Park city

  Lucy Gonzalez Zabala CHARLES RUTENBERG REALTY ORLANDO

  200 Saint Andrews Blvd Unit 2306, Winter Park, FL 32792
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  /12

  $149,000

  • 1 Bed
  • 1 Bath
  • 776 Sq Ft

  1000 S Semoran Blvd Unit 408, Winter Park, FL 32792

  Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Spacious Other units currently available in same complex MLS: R4909222, R4909220, ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other

  Scott Butts KIMBRIDGE REALTY, LLC

  1000 S Semoran Blvd Unit 408, Winter Park, FL 32792
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  /6

  $149,000

  • 1 Bed
  • 1 Bath
  • 776 Sq Ft

  1000 S Semoran Blvd Unit 404, Winter Park, FL 32792

  Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Spacious Other units currently available in same complex MLS: R4909222, R4909221 ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other

  Scott Butts KIMBRIDGE REALTY, LLC

  1000 S Semoran Blvd Unit 404, Winter Park, FL 32792
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  /13

  $149,000

  • 1 Bed
  • 1 Bath
  • 796 Sq Ft

  1000 S Semoran Blvd Unit 306, Winter Park, FL 32792

  Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Spacious Other units currently available in same complex MLS: R4909220, R4909221 ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool and other

  Scott Butts KIMBRIDGE REALTY, LLC

  1000 S Semoran Blvd Unit 306, Winter Park, FL 32792
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  /15

  $185,000

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit E215, Winter Park, FL 32789

  Move-in Ready Renovated Condo – Prime Location!This beautifully renovated condo offers both style and convenience, situated right next to the community pool and playground. Enjoy modern upgrades throughout, along with the added assurance of a Home Warranty America coverage plan, valued up to $500, for extra peace of mind. Plus, you'll be just minutes from restaurants, shopping, major roads,

  Kerem Munoz- Franquiz LA ROSA REALTY CENTRAL FLORIDA

  1695 Lee Rd Unit E215, Winter Park, FL 32789
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  /54

  $485,000

  • 3 Beds
  • 2 Baths
  • 2,706 Sq Ft

  7730 Broken Arrow Trail, Winter Park, FL 32792

  Welcome to this inviting 3-bedroom, 2-bathroom home, perfectly situated on a spacious lot that offers peace, privacy, and room to breathe. From the moment you arrive, you'll be drawn in by the extended driveway and lush, serene surroundings—ideal for anyone seeking a quiet retreat without sacrificing convenience. Step inside and experience the seamless flow of this thoughtfully designed home,

  Waseem Saedi LA ROSA REALTY PREMIER LLC

  7730 Broken Arrow Trail, Winter Park, FL 32792
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  /30

  $450,000

  • 3 Beds
  • 1 Bath
  • 1,140 Sq Ft

  1564 Cavendish Rd, Winter Park, FL 32789

  Charming 3BR bungalow in sought-after Orwin Manor with timeless appeal and tons of potential. Updated with original hardwood floors, gas fireplace, granite kitchen, and bath. The 3rd BR functions as a guest room or office. Spacious fenced yard with wood deck and room for a pool. Deep garage offers space to add a second bath or storage. Original plan was to remove back -to-back closets in LR

  Julie Wright CHARLES RUTENBERG REALTY ORLANDO

  1564 Cavendish Rd, Winter Park, FL 32789
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  /47

  $399,900

  • 4 Beds
  • 2.5 Baths
  • 1,788 Sq Ft

  4421 Steed Terrace, Winter Park, FL 32792

  PRICED TO SELL!!!! FIRE DAMAGED HOUSE - LOTS OF POTENTIAL IN THIS WINTER PARK POOL HOME. This is an exciting opportunity for investors or buyers looking for a project! This home offers a blank canvas for renovation. The property is situated in a quiet, family-friendly neighborhood, making it an ideal candidate for full restoration. With required renovations - this blank canvas will become a

  Andrey Bustamante BUSTAMANTE REAL ESTATE INC

  4421 Steed Terrace, Winter Park, FL 32792
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  /19

  $89,900

  • Studio
  • 1 Bath
  • 549 Sq Ft

  3071 George Mason Ave Unit 5, Winter Park, FL 32792

  NEW PRICE!!! Charming Studio Condo Near UCF & Full Sail – Ideal Investment or Cozy Retreat!Welcome to this well-maintained ground-floor studio condo, offering 549 square feet of comfortable living space in a prime location near UCF and Full Sail University. Perfect for a student, professional, or investor, this move-in-ready unit features tile flooring throughout, making it clean and easy to

  Katherine Bordelon CASTLE & COTTAGE REALTY LLC

  3071 George Mason Ave Unit 5, Winter Park, FL 32792
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  /42

  $765,000

  • 3 Beds
  • 2 Baths
  • 1,827 Sq Ft

  625 Brechin Dr, Winter Park, FL 32792

  PICTURE PERFECT HOME IN WINTER PARK’S KENILWORTH SHORES! Homes of this quality and preservation hardly come on the market – this immaculately kept, 3-bedroom, 2 bath home offers 1,827 SF and a stunning backyard oasis! Interior offers a spacious living room, dining room, and Florida room. The elongated galley kitchen features beautiful hardwood cabinetry, solid countertops, built-in double ovens,

  Kelly Price KELLY PRICE & COMPANY LLC

  625 Brechin Dr, Winter Park, FL 32792
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  /39

  $369,000

  • 3 Beds
  • 2 Baths
  • 1,606 Sq Ft

  1309 Paradise Ln, Winter Park, FL 32792

  New price. Welcome to Harbour Ridge in charming Winter Park — where there’s no HOA and endless potential!Set on a spacious 1/3-acre fully fenced lot, this property offers plenty of room to play, garden, or relax under the Florida sky. There’s even an oversized shed, ideal for extra storage or the perfect workshop setup.Step inside to discover a beautifully renovated kitchen, complete with

  Barbara Mills COLDWELL BANKER REALTY

  1309 Paradise Ln, Winter Park, FL 32792
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  /30

  $459,000

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  1710 Aster Dr, Winter Park, FL 32792

  MOVE-IN Ready Renovated Winter Park home offering 3 bedrooms 2 baths with 1646 sq feet. Nice size lot .24 acre, fenced with a large open pool featuring brand new pool equipment & newly screened patio. 2024 Updates include: NEW Roof, Luxury vinyl flooring, 5 1/4 in. baseboards, popcorn ceilings removed & retextured, Full Kitchen renovation with SS appliances, Soft close cabinets & Quartz counter

  Dora Siler FOLIO REALTY LLC

  1710 Aster Dr, Winter Park, FL 32792
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  /36

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,738 Sq Ft

  1116 Fairway Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. One or more photos has been virtually staged.Welcome to this beautiful, single-family home in the Golfside Community in Winter Park! This stunning 3-bedroom, 2-bathroom residence offers a living space of 1,738 square feet. When you enter the home, you step right into the family room. To the right of it, you can find the dining room/living

  Mathew Kelly TURN-KEY MOVES REALTY

  1116 Fairway Dr, Winter Park, FL 32792
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  /12

  $165,000

  • 2 Beds
  • 2 Baths
  • 1,049 Sq Ft

  1000 S Semoran Blvd Unit 814, Winter Park, FL 32792

  Huge Price Reduction!!! on this Fully remodeled unit. Reduced to sell. This fully updated Condo is minutes from Baldwin Park, Full Sail, UCF, and all of Winter Park has to offer. Don't miss the opportunity to own an amazing home or investment opportunity. Low HOAs are hard to find, especially in Winter Park Zip codes. Don't forget that this home has a fully updated kitchen, bathrooms, and new

  Benjamin Berry EXP REALTY LLC

  1000 S Semoran Blvd Unit 814, Winter Park, FL 32792
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  /34

  $440,000

  • 4 Beds
  • 2 Baths
  • 1,765 Sq Ft

  1621 Puritan Ave, Winter Park, FL 32792

  Down Payment Assistance Available! Welcome to 1621 Puritan Ave, a beautifully renovated pool home located in the highly desirable Winter Park area on the Seminole County side. This property qualifies for multiple down payment assistance programs, making it an excellent opportunity for first-time buyers. Recent upgrades include a new roof (2023), resurfaced pool (2023), and an updated A/C system

  Alejandro Colon PREFERRED REAL ESTATE BROKERS

  1621 Puritan Ave, Winter Park, FL 32792
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  /17

  $274,000

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  4908 Seminole Ave, Winter Park, FL 32792

  Investor Special! This Winter Park gem is an ideal find for investors or home flippers, with *no HOA* and sturdy block construction for peace of mind. Originally a 3-bedroom, 2-bath layout, the home is currently used as a 4-bedroom, 1-bath due to additional walls added by the previous owner. The second bathroom’s plumbing remains intact, simplifying restoration to the original

  Whitney Kane THE AGENCY ORLANDO

  4908 Seminole Ave, Winter Park, FL 32792
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  /11

  $825,000

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft

  2128 Sycamore Dr, Winter Park, FL 32789

  MUST SEE! RENOVATED, MOVE-IN READY! Don’t miss this fantastic opportunity to own a beautiful 3-bedroom, 2-bathroom home situated on a spacious .23-acre corner lot. This property has undergone a complete upgrade inside and out, making it perfect for those looking for a fresh start. Key Features: • Newer Septic Tank: Ensures peace of mind and efficiency. • 2016 Roof: A reliable roof that adds to

  Luis Perez Garcia EXP Realty LLC

  2128 Sycamore Dr, Winter Park, FL 32789
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  /89

  $1,999,993

  • 6 Beds
  • 4 Baths
  • 3,853 Sq Ft

  1451 Lyndale Blvd, Winter Park, FL 32789

  **Luxurious Winter Park Estate with Detached TWO bedroom Guest House** RENOVATED POOL HOME with NO HOA! TWO Primary Bedrooms located on the main floor! Welcome to a world of unparalleled luxury and elegance in the heart of historic Winter Park, FL. This exquisitely renovated two-story pool home, set on a sprawling corner lot, offers a rare opportunity to experience the pinnacle of

  Christopher Soucy REALTY ONE GROUP MVP

  1451 Lyndale Blvd, Winter Park, FL 32789
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  /35

  $299,500

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft

  2384 Sun Valley Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to your dream home in beautiful Winter Park, Florida! This charming 3-bedroom, 2-bath corner unit is just half a mile from Casselberry Commons, offering shopping, dining, and everyday convenience right at your doorstep.Enjoy peace of mind with a new roof (2023), new thermostat and fan (2024), and updated AC ducts and insulation

  Yvette Hernandez THE REALTY EXPERIENCE POWERED BY LRR

  2384 Sun Valley Cir, Winter Park, FL 32792
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  /26

  $370,000

  • 3 Beds
  • 2 Baths
  • 1,283 Sq Ft

  780 Baffie Ave, Winter Park, FL 32789

  Great opportunity to live in Winter Park in the Dubsdread Golf Community. This 3 bedroom, 2 bath home is situated on a deep lot (50 x 140) with 1283 sq. ft., Bamboo hardwood floors in several rooms, split bedroom floor plan, large kitchen with tile floors, and oak cabinets, and the dining room has a tongue and groove wood ceiling. The primary bedroom has Bamboo floors, tongue and groove wood

  Melissa Woodman FANNIE HILLMAN & ASSOCIATES

  780 Baffie Ave, Winter Park, FL 32789
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  /2

  $419,900

  • 3 Beds
  • 2 Baths
  • 1,405 Sq Ft

  616 Ellendale Dr, Winter Park, FL 32792

  Desirable Winter Park Estates - close to everything! Beautifully updated 3 Bedroom 2 Bath POOL home which is located in a highly desirable school district! Updated Contemporary Kitchen has newer Cabinetry, newer Stainless-Steel appliances, and Granite countertops which connect with the open Living room. Dining area extends to the generous size Family room - Ideal for Entertaining. The home

  David Ruiz CENTRAL REALTY

  616 Ellendale Dr, Winter Park, FL 32792
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  /19

  $5,950,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,448 Sq Ft

  1181 Via Capri, Winter Park, FL 32789

  Under Construction. Situated on one of the choicest streets in Winter Park on a large and lovely lot will soon be a Phil Kean Design Group new construction project.Enjoy a world class location along with award winning Architecture and Design.Construction is expected to be complete in mid 2026.A Phil Kean Design Group representative can be available for a sit down to discuss complete

  Brad Grosberg PHIL KEAN REAL ESTATE LLC

  1181 Via Capri, Winter Park, FL 32789
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  /35

  $4,250,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 3,413 Sq Ft

  1120 Palmer Ave, Winter Park, FL 32789

  Spectacular Phil Kean Design Group whole home remodel coming soon.Miami/Coral Gables Cottage meets Winter Park Elegance.On a street of Winter Park estates this home will be a charming and sophisticated addition.Currently under construction and being reimagined for the 2026 International Builders Show "Show Home Remodel".This home will be available for occupancy in February

  Brad Grosberg PHIL KEAN REAL ESTATE LLC

  1120 Palmer Ave, Winter Park, FL 32789
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  /48

  $1,275,000 New Construction

  • 4 Beds
  • 3 Baths
  • 3,710 Sq Ft

  5236 Lake Howell Rd, Winter Park, FL 32792

  Experience the best of Winter Park living in this stunning new custom-built pool home situated on a generous .29-acre lot just 1.9 miles from Park Avenue. Designed with a modern aesthetic and built to the highest standards, this 4-bedroom, 3-bath residence is a true showcase of craftsmanship and luxury. Step inside to discover a stunning vaulted great room where the kitchen, living, and dining

  Troy Hensley BHHS FLORIDA REALTY

  5236 Lake Howell Rd, Winter Park, FL 32792
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  /12

  $1,800,000 New Construction

  • 5 Beds
  • 4 Baths
  • 3,246 Sq Ft

  2260 Mulbry Dr, Winter Park, FL 32789

  Pre-Construction. To be built. Price Improvement!!! Your Dream Home Is Ready To Be Built!! Pre-Construction Opportunity! Build-to-Suit! Buyers who act now can still pick finishes and style! Build your custom dream home with renowned Konkol Homes in one of Central Florida’s most desirable areas! This nearly 1/4-acre lot is perfectly situated near Baldwin Park, East End Market, Audubon Park K-8,

  Farah Bloom KELLER WILLIAMS WINTER PARK

  2260 Mulbry Dr, Winter Park, FL 32789
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  /100

  $6,600,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,636 Sq Ft

  2661 Vía Tuscany, Winter Park, FL 32789

  CALLING HIGHEST AND BEST BY 09/26/2025!! SELLER FINANCING AVAILABLE WITH VERY ATTRACTIVE TERMSIntroducing 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

  Prescilla Vazquez PV LUXURY GROUP PA

  2661 Vía Tuscany, Winter Park, FL 32789
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  /6

  $500,000

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  1816 Azalea Ave, Winter Park, FL 32789

  Short Sale. Short Sale. Subject to seller's lender(s) approval of contract, terms. Property sold as-is. Buyer responsible for due diligence, including verifying HOA, taxes, fees, and condition. subject to lender approval and may be adjusted. MORE PHOTOS COMING SOON!!! Nestled in the heart of Winter Park, this property offers unmatched convenience with countless dining, shopping, and entertainment

  Juan Vazquez LPT REALTY, LLC

  1816 Azalea Ave, Winter Park, FL 32789
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  /31

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,088 Sq Ft

  1073 Hamlet Dr, Maitland, FL 32751

  Welcome to 1073 Hamlet Drive—an updated 3-bedroom, 2-bathroom block home with over 1,000 square feet of comfortable living space, a 1-cargarage, and a prime location in the highly sought-after community of Hamlet at Maitland. From the moment you step inside, you'll be greeted byvaulted ceilings, an abundance of natural light, and an open floor plan that’s ideal for entertaining. The

  Wendy Jane MacAnthony ELEGANT REALTY LLC

  1073 Hamlet Dr, Maitland, FL 32751
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  /26

  $1,250,000

  • 3 Beds
  • 2.5 Baths
  • 2,707 Sq Ft

  3632 Upper Union Rd, Orlando, FL 32814

  Charming and Rare David Weekley Home on Oversized Manor Lot in Baldwin ParkWelcome to 3632 Upper Union Road, Orlando, FL 32814, a beautifully maintained 3-bedroom, 2.5-bath David Weekley Village Home on a rare oversized Manor lot in the heart of Baldwin Park.This 2,707 sqft home exudes classic charm with its Victorian-inspired elevation, inviting full-length front porch, and one of

  Stephen Hachey FLAT FEE MLS REALTY

  3632 Upper Union Rd, Orlando, FL 32814
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  /50

  $1,097,000

  • 3 Beds
  • 3 Baths
  • 2,460 Sq Ft

  1901 Lake Sue Dr, Orlando, FL 32803

  One story, 3-bedroom, 3 bath, RENOVATED home with resort-style backyard and screened lap pool is ready to move in to. It features a modern kitchen with a marble Breakfast bar and marble countertops. An Open floor plan with lots of natural light. New white oak wood floors installed throughout in September 2025. The huge primary Bedroom suite with sitting area and private bath, his and hers

  Pamela Stewart REALCOM REAL ESTATE SERVICES INC

  1901 Lake Sue Dr, Orlando, FL 32803

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