Studio to 2 Bedroom Homes for Sale in Winter Park, FL

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  /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 JASON MITCHELL REAL ESTATE FLO

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

  

  

  /22

  $200,000

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft

  2923 Antique Oaks Cir Unit 39, Winter Park, FL 32792

  Condo in Winter Park, FL Welcome to 2923 Antique Oaks Cir, Unit 39 — a beautifully updated 1,105 sq. ft. first-floor condo offering 2 bedrooms, 2 bathrooms, and modern upgrades throughout. Located in the highly sought-after Winter Park School District, this property combines comfort, style, and convenience. Property Highlights: Size & Layout: Spacious 1,105 square feet with a thoughtfully

  Michell Carrasquero GLOBALWIDE REALTY LLC

  2923 Antique Oaks Cir Unit 39, Winter Park, FL 32792
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  /2

  $80,000

  • 1 Bed
  • 1 Bath
  • 756 Sq Ft

  182 Scottsdale Square Unit 182, Winter Park, FL 32792

  Don't miss this exceptional opportunity to invest in a 1-bedroom, 1-bathroom condo in the heart of Winter Park. Centrally located near Baldwin Park, Full Sail University, the University of Central Florida (UCF), Downtown Winter Park, and Orlando International Airport, this property offers unmatched convenience.

  Tania Harmon KELLER WILLIAMS REALTY AT THE PARKS

  182 Scottsdale Square Unit 182, Winter Park, FL 32792
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  /24

  $129,000

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit E211, Winter Park, FL 32789

  HUGE $15,900 PRICE DROP! Discover your perfect home in this two-bedroom, one-bath second-floor unit at Waterfall Cove, ideally situated in the heart of Winter Park. This inviting open-concept layout features large windows that fill the space with natural light, along with cozy carpeting throughout and stylish tile in the bathroom. Each bedroom offers a comfortable retreat, while sliding glass

  David Small KELLER WILLIAMS REALTY SMART 1

  1695 Lee Rd Unit E211, Winter Park, FL 32789
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  /33

  $229,000

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 204, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Investors Dream with Minimal Lease Restrictions! Back on Market. Buyer financing fell through. Welcome to the Lake Killarney Condo Community! This two-bedroom, one-bathroom condo features sold surface countertops in the kitchen, complete bathroom renovation with updated fixtures, newer floors in some rooms, washer/dryer hookups, newer kitchen

  Eddie Cooper MAINFRAME REAL ESTATE

  151 N Orlando Ave Unit 204, Winter Park, FL 32789
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  /32

  $399,000

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

  240 Killarney Bay Ct Unit 4, Winter Park, FL 32789

  Welcome to Killarney Bay—Winter Park’s best-kept secret for tranquil lakeside living, and just steps from the city’s finest shopping and dining!This beautifully updated and spacious 2-bedroom, 2.5-bath townhome-style condo offers a rare blend of modern upgrades and classic charm. Enjoy a BRAND NEW WATER HEATER, vaulted ceilings, a wood-burning fireplace, and rich wood-like flooring

  Blaike Gill KELLER WILLIAMS WINTER PARK

  240 Killarney Bay Ct Unit 4, Winter Park, FL 32789
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  /8

  $110,000

  • 1 Bed
  • 1 Bath
  • 785 Sq Ft

  311 Scottsdale Square Unit 311, Winter Park, FL 32792

  This 1 bedroom, 1 bath condo at 311 Scottsdale Sq, Winter Park, FL 32792 is leased to a reliable long-term tenant paying $1,450 / month. Located on the first floor in the established Winter Park Woods community, this unit features an open-concept layout as soon as you walk in. The HOA includes water, access to two community pools, a playground, and tennis courts. Winter Park Woods is also zoned

  Omar Rodriguez EMPIRE NETWORK REALTY

  311 Scottsdale Square Unit 311, Winter Park, FL 32792
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  /15

  $1,107,750

  • 2 Beds
  • 2 Baths
  • 1,329 Sq Ft

  240 E Lake Sue Ave, Winter Park, FL 32789

  Discover the perfect blend of convenience and tranquility with this delightful single-family home located in the sought-after Winter Park community. Situated on East Lake Sue Avenue, this property sits on a beautifully maintained lot featuring mature trees and lush landscaping that provides plenty of shade and privacy. Enjoy the ultimate Winter Park lifestyle with close proximity to Park Avenue’s

  Tika Van Den Hurk Compass Florida, LLC

  240 E Lake Sue Ave, Winter Park, FL 32789
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  /32

  $179,900

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  224 Lewfield Cir Unit 224, Winter Park, FL 32792

  Welcome to easy, low-maintenance living in the heart of highly sought-after Winter Park! This charming 2-bedroom, 2-bath second-floor condo features a smart, functional layout and an unbeatable location just minutes from everything Central Florida has to offer. Major updates include a 2019 water heater, HOA-completed roofing and plumbing improvements (2019), plus a whole-home warranty for added

  Chris Creegan CREEGAN GROUP

  224 Lewfield Cir Unit 224, Winter Park, FL 32792
• 

  

  /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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  /62

  $1,675,000

  • 2 Beds
  • 2 Baths
  • 1,511 Sq Ft

  315 E New England Ave Unit 7, Winter Park, FL 32789

  Located on the second floor of Villa Siena, this two-bedroom, two-bath residence offers 1,511 square feet of elegantly appointed living space with two balconies overlooking New England Avenue’s tree-lined brick streets in the heart of Winter Park. A split-bedroom layout ensures privacy, with wood flooring and tray ceilings defining the open-concept living and dining areas. The kitchen features

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  315 E New England Ave Unit 7, Winter Park, FL 32789
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  /29

  $949,000

  • 2 Beds
  • 2 Baths
  • 1,086 Sq Ft

  560 Ololu Dr, Winter Park, FL 32789

  Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this

  Tiffany Yates COMPASS FLORIDA LLC

  560 Ololu Dr, Winter Park, FL 32789
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  /41

  $123,000

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit C214, Winter Park, FL 32789

  Charming 2-bedroom, 1-bath condo located in the heart of Winter Park. This well-maintained unit offers comfortable living with an open layout, ample natural light, and convenient access to shopping, and dining. Enjoy the community pool and beautifully landscaped grounds, perfect for relaxing or entertaining. Ideal for first-time buyers, investors, or anyone looking to enjoy the Winter Park

  Diana Perez PROFESSIONAL REAL ESTATE TEAM

  1695 Lee Rd Unit C214, Winter Park, FL 32789
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  /49

  $195,000

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 208, Winter Park, FL 32789

  This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water is included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to

  Debbie Fussell KELLER WILLIAMS REALTY AT THE PARKS

  2500 Lee Rd Unit 208, Winter Park, FL 32789
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  /24

  $219,000 Open Sun 1PM - 3PM

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft

  851 Miles Ave Unit 13, Winter Park, FL 32789

  Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor condo in the heart of charming Winter Park, FL 32789! Meticulously updated since 2023, this home blends modern luxury with effortless comfort and is truly move-in ready.As you step inside, you’ll be greeted by elegant porcelain tile flooring throughout—offering both durability and a look that’s easy to

  Eric Campbell LPT REALTY, LLC

  851 Miles Ave Unit 13, Winter Park, FL 32789
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  /41

  $879,000

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft

  100 S Interlachen Ave Unit 503, Winter Park, FL 32789

  Welcome to The Cloisters, one of Winter Park’s established lakefront communities, ideally between Park Avenue and Lake Osceola. This top-floor residence, rarely available in the building, offers a turnkey lifestyle with exceptional updates and peaceful water views. The home’s oversized screened balcony, complete with a custom awning, creates an uncommon open-air retreat that overlooks the

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 503, Winter Park, FL 32789
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  /12

  $157,000

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft

  296 Lewfield Cir, Winter Park, FL 32792

  1 bed, 1 bath condo in Winter Park

  Jonathan Minerick HOMECOIN.COM

  296 Lewfield Cir, Winter Park, FL 32792
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  /26

  $355,000

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789

  Tucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfect blend of privacy, style, and unbeatable location. Just one block from Winter Park Village and only a mile from Park Avenue, you’ll enjoy walkable access to some of the area’s best dining, shopping, and entertainment. Located on the first floor, this beautifully renovated 2-bed, 2-bath home features an open

  Brandon Geers COMPASS FLORIDA LLC

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789
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  /26

  $635,000

  • 2 Beds
  • 2 Baths
  • 949 Sq Ft

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

  FIRST TIME ON THE MARKET! ULTRA-RARE GROUND FLOOR CONDO IN DOWNTOWN WINTER PARK'S LACHEN HOUSE – AVAILABLE FOR RENT OR PURCHASE! This is your chance to secure a highly coveted ground floor unit in one of Winter Park's most desirable locations. Available for rent at $3,800/month or purchase at $635,000 with quick move-in or quick closing possible!This stunning 2-bedroom, 2-bath condo has been

  Kelly Price KELLY PRICE & COMPANY LLC

  101 S Interlachen Ave Unit 104, Winter Park, FL 32789
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  /7

  $100,000

  • 1 Bed
  • 1 Bath
  • 756 Sq Ft

  107 Scottsdale Square, Winter Park, FL 32792

  First floor, Move in ready unit! Tile floors throughout. Perfect for a first time buyer or an investor. Close to great schools, restaurants, major highways and more! Call or text to schedule a showing!

  Cristina Burgos REALSOURCE PROPERTY MANGNT LLC

  107 Scottsdale Square, Winter Park, FL 32792
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  /29

  $372,500

  • 2 Beds
  • 2 Baths
  • 1,495 Sq Ft

  1229 Park Green Place, Winter Park, FL 32789

  This 2 bedroom, 2 bathroom townhome offers 1,495 square feet of beautifully designed space in a highly sought-after location. Enjoy a bright living area featuring a gorgeous tiled fireplace, built-in bookshelves, and two sets of French doors that open to your private patio and fenced backyard with brick pavers and turf grass. The home includes a spacious double vanity bathroom, custom shelving

  Steven Koleno BEYCOME OF FLORIDA LLC

  1229 Park Green Place, Winter Park, FL 32789
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  /34

  $158,000

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit D113, Winter Park, FL 32789

  Welcome to this charming 2-bedroom, 1-bathroom first-floor condo conveniently located in the heart of Winter Park. Ideal for investors as it is currently leased. This home offers a spacious open layout with plenty of natural light, NO CARPET, and a functional floor plan perfect for comfortable living.The kitchen features ample cabinet space and next to it you will find the laundry closet

  Gisela Gaztambide Balzac EMPIRE NETWORK REALTY

  1695 Lee Rd Unit D113, Winter Park, FL 32789
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  /40

  $359,000

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft

  311 E Morse Blvd Unit 7-5, Winter Park, FL 32789

  Major Price Improvement! Here is your rare opportunity to own a studio apartment in Whispering Waters, a 55+ iconic Condominium located just steps from Park Avenue and fabulous historic downtown Winter Park! This architectural mid-century beauty was built in 1960 and has survived every major hurricane since then. Whispering Waters has passed the Milestone and Structural Integrity Reserve Study

  Jeff Dodds CHARLES RUTENBERG REALTY ORLANDO

  311 E Morse Blvd Unit 7-5, Winter Park, FL 32789
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  /39

  $239,990

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 202, Winter Park, FL 32789

  2/2 * IMMACULATE CONDO * LOW HOA * LIVE ON LAKE KILLARNEY * ENJOY PARK AVE IN WINTER PARK * 3 MILES TO ROLLINS COLLEGE * NEW AC * NEW WATER HEATER * NEW INTERIOR PAINT * NEW LIGHTING * Immaculate updated 2 bedroom 2 bathroom Condo in a prime location on beautiful Lake Killarney, a serene oasis in Winter Park. A walkable Lake community providing Residents with direct Lake Access, Private Dock with

  Alison Maltby THE ANDERSON GROUP & CO PL

  2500 Lee Rd Unit 202, Winter Park, FL 32789
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  /21

  $159,000

  • 1 Bed
  • 1 Bath
  • 749 Sq Ft

  2905 Antique Oaks Cir Unit 6, Winter Park, FL 32792

  For Sale – Beautifully Remodeled 1 Bedroom / 1 Bath Condo – Parkview Village, Winter Park Beautifully remodeled 1-bedroom, 1-bath condo featuring elegant wood floors and fresh paint throughout. Spacious living and dining areas open to a lovely screened patio — perfect for relaxing. Located in Parkview Village, a quiet and convenient community in front of to Full Sail University, and just minutes

  Clara Herrera CLARA HERRERA REALTY

  2905 Antique Oaks Cir Unit 6, Winter Park, FL 32792
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  /25

  $109,999

  • 1 Bed
  • 1 Bath

  7309 Daniel Webster Dr Unit 2B, Winter Park, FL 32792

  Remodeled 1-bedroom, 1-bathroom condo in Winter Park, FL. Newly installed A/C ensures year-round comfort. Located in a tranquil complex with amenities including a tennis court, pool house, laundry room, and clubhouse. unit has a washer and dryer hookup, ideal for investors and owner users with no pet or long term rental restrictions. Conveniently located near shopping centers and various dining

  Robert Castro RE/MAX - City Centre Realty

  7309 Daniel Webster Dr Unit 2B, Winter Park, FL 32792
• 

  

  /20

  $237,000

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

  200 Saint Andrews Blvd Unit 3001, Winter Park, FL 32792

  Experience the best value in Winter Park. Beautifully maintained corner-unit townhome in the desirable Four Seasons community, offering a perfect blend of comfort, privacy and style. This bright and inviting residence features modern laminated floors, new carpet in the bedroom areas, granite kitchen countertops, updated lighting, and recently painted interiors. Enjoy the convenience of a private

  Magaly Laplana Kleros Realty

  200 Saint Andrews Blvd Unit 3001, Winter Park, FL 32792
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  /36

  $329,000

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  311 E Morse Blvd Unit 6-3, Winter Park, FL 32789

  Discover your new downtown Winter Park ground-floor pied-à-terre. Two blocks from Park Avenue, the 1960s mid-century modern Whispering Waters Condominiums are a Winter Park landmark. Your remodeled end-unit studio features an updated open kitchen with plentiful wood cabinets, ceramic tile flooring throughout, new dual-pane windows, a stylish updated bathroom with a step-in shower, and wood

  Richard Traynor FLORIDA ONE REAL ESTATE LLC

  311 E Morse Blvd Unit 6-3, Winter Park, FL 32789
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  /63

  $631,400

  • 2 Beds
  • 2 Baths
  • 1,057 Sq Ft

  265 E Canton Ave Unit GE, Winter Park, FL 32789

  RARE CORNER TOP-FLOOR CONDO WITH AMAZING VIEWS – FULLY FURNISHED AND IN THE HEART OF WINTER PARK! Discover the perfect blend of comfort, style, and unbeatable location! This beautifully maintained 2-bedroom, 2-bath corner unit sits on the top floor of the desirable Villages of Winterset, offering expansive views and abundant natural light throughout. Enjoy the convenience of two elevators, a

  Luciana Amorim Panajotti FLORIDA CONNEXION PROPERTIES

  265 E Canton Ave Unit GE, Winter Park, FL 32789
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  /20

  $168,150

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  3651 N Goldenrod Rd Unit 102, Winter Park, FL 32792

  PRICE IMPROVEMENT!! Welcome to this beautifully maintained 2-bedroom, 2-bathroom first-floor condo, offering comfort, convenience, and peace of mind with major updates completed in 2023. This move-in-ready home features a brand-new TRANE A/C unit (2023), a new roof (2023), and new exterior paint (2023)—ensuring long-term efficiency and a fresh, modern look from the moment you arrive. Step inside

  Ashley Fulford CHARLES RUTENBERG REALTY ORLANDO

  3651 N Goldenrod Rd Unit 102, Winter Park, FL 32792
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  /24

  $179,900

  • 1 Bed
  • 1 Bath
  • 653 Sq Ft

  1250 S Denning #122 St Unit 122, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Come take a lovely stroll to Mead Gardens(47 acres), located just around the corner from this adorable condo in one of Winter Park’s most popular communities! The pool is located directly behind this condo! This cozy first-floor unit features brand-new luxury vinyl flooring that gives it a fresh, welcoming feel. The spacious living room has sliders

  Leah Laboy EDEN CREST REALTY, LLC

  1250 S Denning #122 St Unit 122, Winter Park, FL 32789
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  /32

  $1,195,000

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft

  100 S Interlachen Ave Unit 415, Winter Park, FL 32789

  Residence 415 at The Cloisters offers a rare opportunity to own a comprehensively rebuilt home in one of Winter Park’s enduring lakefront communities. Set on the fourth floor, just one block from Park Avenue, this residence blends timeless architecture with newly reimagined design. Taken thoughtfully down to its original structure and meticulously reconstructed with longevity in mind, this

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 415, Winter Park, FL 32789
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  /28

  $450,000

  • 1 Bed
  • 1 Bath
  • 673 Sq Ft

  640 N Park Ave Unit 5, Winter Park, FL 32789

  Location, Location, Location!Charming first floor 1 bedroom, 1 bath condo ideally located on North Park Avenue in the retro-chic Park Aire complex. Beautifully overhauled in 2018 with quartz counters, new cabinetry, new appliances, custom mosaic kitchen detail, new flooring, new lighting, updated electrical, with picturesque views of the Winter Park Golf Course and Casa Feliz.Enjoy a

  David Auerbach PARK TOWN REAL ESTATE LLC

  640 N Park Ave Unit 5, Winter Park, FL 32789
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  /7

  $196,400

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft

  2923 Antique Oaks Cir Unit 37, Winter Park, FL 32792

  Condo in Winter Park, FL. 2923 Antique Oaks Cir, Unit 37. Updated 1,105 sq. ft. first-floor, North West corner condo. 2 bedrooms, 2 bathrooms. Located in the Winter Park School District: Updated Interiors: Recently remodeled with modern finishes, including brand-new appliances (convection oven, refrigerator, dishwasher), and a new LG stackable washer/dryer in the interior laundry room. Outdoor

  Cliff Glansen FLATFEE.COM

  2923 Antique Oaks Cir Unit 37, Winter Park, FL 32792
• 

  /2

  $99,900

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

  126 Scottsdale Square Unit B126, Winter Park, FL 32792

  Excellent opportunity to own this First-floor, 2-bedroom, 1/1-bath condo in a Conveniently location close to healthy centers, excellent schools, restaurants and shopping with easy access to Costco, Walmart, and various dining options. Only 4 miles from Winter Park SunRail Train Station and 20 minutes from Orlando International Airport.This unit offers a cozy living/dining area with sliding

  Maria Batista LPT REALTY, LLC

  126 Scottsdale Square Unit B126, Winter Park, FL 32792
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  /29

  $250,000

  • 2 Beds
  • 2 Baths
  • 1,087 Sq Ft

  1601 Grove St Unit 552, Maitland, FL 32751

  One or more photo(s) has been virtually staged. **2024 ROOF** Discover this stunning, newly renovated one story end unit boasting over 1,000 sq ft of modern living space. This spacious 2 bedroom, 2 bath condo features luxury vinyl plank flooring throughout, a stylish new kitchen with white shaker cabinets, quartz countertops, and stainless steel appliances, plus all new light fixtures and fresh

  Chris Creegan CREEGAN GROUP

  1601 Grove St Unit 552, Maitland, FL 32751
• 

  

  /18

  $599,900

  • 1 Bed
  • 1 Bath
  • 1,251 Sq Ft

  1616 Oriole Ave, Orlando, FL 32803

  Lake Front Mid Century Modern Home in desirable Audubon Park. Natural light follows throughout the home with a skylight in the newly remodeled Kitchen with new Kitchen Aid Appliances with propane stove . The entire home has polished concrete flooring and the home has the original Retro Ä Mid Century Bathroom. New electrical panel, all electrical is upgraded and the home has been replumbed. The

  Barbara Eads LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  1616 Oriole Ave, Orlando, FL 32803

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