Orange, FL Homes

• 

  

  

  /29

  $375,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft

  2827 Euston Rd, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to 2827 Euston Rd, a beautifully updated home in the highly desirable Winter Park area with the added bonus of no HOA! This charming residence offers 3 beds, 2baths, and a versatile bonus room that can be used as an office, playroom, or additional living space.The master suite is thoughtfully separated from the other two bedrooms, providing

  

  Evelyn Tejada

  REGENCY REAL ESTATE LLC

  (321) 461-5735

  2827 Euston Rd, Winter Park, FL 32789
• 

  Explore Winter Park

• 

  

  

  /37

  $3,400 per month

  • 3 Beds
  • 2.5 Baths
  • 1,798 Sq Ft
  • Townhouse for Rent

  1273 Michigan Ave, Winter Park, FL 32789

  **Luxury Townhomes for Lease in the Heart of Winter Park!**Experience upscale living in this stunning townhome community crafted by award-winning Osprey Custom Home Builders. These **3-bedroom, 2.5-bath Florida Green Certified Homes** offer an open-concept layout with high-end designer finishes throughout.The first floor features spacious living and dining areas and a gourmet kitchen

  

  Miranda Azer

  PARKVIEW REAL ESTATE

  (321) 621-8878

  1273 Michigan Ave, Winter Park, FL 32789
• 

  

  /2

  $185,000 Sold Aug 05, 2025

  • 987 Sq Ft
  • $187/SF
  • 7 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  200 St Andrews Blvd Unit 802, Winter Park, FL 32792

  Welcome to easy living in the heart of Winter Park! This beautiful 1st-floor condo is move-in ready and packed with value—featuring a new electrical panel, in-unit washer and dryer, fresh interior paint, and popcorn ceilings removed for a modern, clean feel. Enjoy the convenience of a covered carport and peace of mind knowing this property is Fannie Mae eligible so you won't have any issue

  Abby Greenberg COMPASS FLORIDA LLC

  200 St Andrews Blvd Unit 802, Winter Park, FL 32792
• 

  

  

  /42

  Est $1,621,115 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,052 Sq Ft

  1805 Harland Park Dr, Winter Park, FL 32789

  1805 Harland Park Dr, Winter Park, FL 32789
• 

  

  

  /46

  $1,100,000 Open Sun 1PM - 3PM

  • 5 Beds
  • 4.5 Baths
  • 3,839 Sq Ft

  2880 Old Castle Dr, Winter Park, FL 32792

  Welcome to this beautifully designed executive pool home with private in-law quarters, nestled on an oversized corner lot in the gated community of Bear Gully Pointe in Winter Park. Thoughtfully crafted with architectural elegance, this residence features timeless details including plantation shutters, crown molding, and hardwood flooring throughout the first floor.Step inside and be

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 517-2794

  2880 Old Castle Dr, Winter Park, FL 32792
• 

  

  /23

  $1,799 - $5,829 per month

  Juno Winter Park

  Studio - 3 Beds

  1305 Morgan Stanley Ave, Winter Park, FL 32789

  Situated in Winter Park near Harry P Leu Gardens, Juno Winter Park brings you urban living at its height. Featuring exquisite studio, one, two, and three-bedroom apartments along with a variety of enviable amenities, our vibrant community invites you to elevate your everyday life. Plus, our prime location just six miles north of downtown Orlando puts you within arm's reach of top-notch shopping,

  1305 Morgan Stanley Ave, Winter Park, FL 32789
• 

  /2

  $425,000 Sold Aug 04, 2025

  • 1,148 Sq Ft
  • $370/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1969

  690 Osceola Ave Unit 410, Winter Park, FL 32789

  Welcome to this newly updated 2-bedroom, 2-bath condo ideally situated just steps down from shops, dining, and cultural attractions of Park Ave and Rollins College. Freshly painted and featuring brand-new flooring throughout, this home offers a perfect blend of comfort, convenience, and modern style.The spacious open layout includes a bright living area that opens to a lovely screened-in

  Catherine Mitchell LOMBARDI LEMAY REALTY

  690 Osceola Ave Unit 410, Winter Park, FL 32789
• 

  

  /26

  Est $499,567 Not Listed For Sale

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

  2469 Firstlight Way, Winter Park, FL 32792

  2469 Firstlight Way, Winter Park, FL 32792
• 

  

  /89

  $1,000,000

  • 4 Beds
  • 3.5 Baths
  • 3,074 Sq Ft

  4107 Gabriella Ln, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Do you have a vision? Do you love Nature? Welcome to this Exceptional Bear Gully Lakefront Retreat – A Rare Blend of Privacy and Natural Beauty! Refurbish the house as it is, or start new on this amazing rare natural Florida lakefront ground. Tucked away on the serene shores of Bear Gully Lake, this one-of-a-kind property presents a rare

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  (321) 382-1061

  4107 Gabriella Ln, Winter Park, FL 32792
• 

  

  /21

  $2,800 per month

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft
  • Townhouse for Rent

  2352 Shadowland Loop, Winter Park, FL 32792

  Spacious 3-bedroom, 2.5-bath townhouse available for rent in beautiful Winter Park, Florida. This charming home features modern finishes and walk-in closets for every bedroom. Enjoy community features like a luxurious pool, dog park, and playground. Located minutes from top-rated schools, dining, and shopping in downtown Winter Park, this townhouse is perfect for anyone looking for comfort and

  Rebecca Sossai COLDWELL BANKER RESIDENTIAL RE

  2352 Shadowland Loop, Winter Park, FL 32792
• 

  /2

  $200,000 Sold Aug 04, 2025

  • 1,018 Sq Ft
  • $196/SF
  • 159 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  2935 Antique Oaks Cir Unit 64, Winter Park, FL 32792

  Welcome to your new home at 2935 Antique Oaks Cir Apt 64, a beautifully renovated 2-bedroom, 2-bathroom apartment in the heart of Winter Park, Florida. This second-floor unit offers a comfortable and convenient lifestyle with no upstairs neighbors, ensuring peace and privacy. Key Features:Renovated Interior: Enjoy a fresh and modern living space with stylish LVP flooring

  Chris Creegan CREEGAN GROUP

  2935 Antique Oaks Cir Unit 64, Winter Park, FL 32792
• 

  

  /47

  Est $1,133,231 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,575 Sq Ft

  1939 Woodcrest Dr, Winter Park, FL 32792

  1939 Woodcrest Dr, Winter Park, FL 32792
• 

  

  /42

  $875,000

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft

  1090 Wildmeadow Run, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. This luxurious Modern Style home delivers the pinnacle lifestyle, in every aspect of MAINTENANCE FREE LIVING. You will enjoy premium views of nature with a RESORT CLUBHOUSE featuring an abundance of amenities including a resort pool, fitness center & playground, all JUST 250 FEET AWAY....This home has been IMPECCABLY MAINTAINED, and includes the

  

  Rod Chevalier

  BHHS FLORIDA REALTY

  (321) 339-2639

  1090 Wildmeadow Run, Winter Park, FL 32792
• 

  

  /25

  $1,399 - $1,659 per month

  Indigo Winter Park

  1 Bed

  220 S Semoran Blvd, Winter Park, FL 32792

  Indigo Winter Park is a lavishly landscaped apartment home community. Each of our one bedroom, one bathroom apartments feature laminate flooring, carpeted bedrooms, washers & dryers, walk in closets, screened in patios, maple wood cabinetry, gas stoves and efficient appliances. Our pet-friendly apartment community includes three resort style pools, bbq grilling stations, two double tennis courts,

  220 S Semoran Blvd, Winter Park, FL 32792
• 

  /2

  $815,000 Sold Aug 04, 2025

  • 2,533 Sq Ft
  • $322/SF
  • 316 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1926

  1310 Aloma Ave, Winter Park, FL 32789

  Elegant Spanish 4 bedroom, 2.5 bathroom home. Beautifully updated Winter Park home. Enjoy all the luxuries and upgrades this home has to offer including triple crown molding, tall baseboards, refinished original hard wood floors, recessed lighting, French doors, paver driveway and newer windows though out with new plantation shutters. Large living room has a fabulous brick wood burning

  Rhonda Chesmore KELLY PRICE & COMPANY LLC

  1310 Aloma Ave, Winter Park, FL 32789
• 

  /2

  Est $477,223 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,598 Sq Ft

  1761 Indiana Ave Unit F, Winter Park, FL 32789

  1761 Indiana Ave Unit F, Winter Park, FL 32789
• 

  

  /44

  $729,000

  • 4 Beds
  • 2.5 Baths
  • 2,046 Sq Ft

  607 Dunblane Dr, Winter Park, FL 32792

  Welcome to this beautifully renovated 4-bedroom, 2.5-bath home in the heart of Winter Park, just minutes from Park Avenue’s top dining and shopping. Thoughtfully updated from top to bottom, this move-in-ready home features a brand-new AC system, luxury vinyl plank flooring throughout, and a stunning chef’s kitchen with quartz waterfall countertops, custom cabinetry, and all-new stainless steel

  

  Khozaif Merali

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 490-4706

  607 Dunblane Dr, Winter Park, FL 32792
• 

  

  /39

  $6,000 per month

  • 3 Beds
  • 3 Baths
  • 2,390 Sq Ft
  • Townhouse for Rent

  1140 S Pennsylvania Ave, Winter Park, FL 32789

  Elegant 3 bedroom, 3 bathroom townhome for rent in the Heart of Winter Park. Enjoy refined, low-maintenance living just steps from Park Avenue, Rollins College, and excellent dining and shopping. This bright, open townhome features hardwood floors, crown molding, plantation shutters, and a chef’s kitchen with GE Monogram appliances, gas cooktop, stone counters, and breakfast bar. Perfect for

  Meg Dolan FANNIE HILLMAN & ASSOCIATES

  1140 S Pennsylvania Ave, Winter Park, FL 32789
• 

  /2

  $320,000 Sold Aug 01, 2025

  • 1,715 Sq Ft
  • $187/SF
  • 18 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  2020 Cocos Ct, Winter Park, FL 32792

  Fantastic Investment or Renovation Opportunity in Winter Park! Located in the desirable Eastbrook community, this 3-bedroom, 2-bathroom POOL home with ONLY ONE OWNER sits on an oversized .30 ACRE CORNER LOT on a quiet CUL-DE-SAC with no HOA. Offering 1715 square feet of living space, a 1-car garage, and a spacious fenced backyard, this property is a true blank canvas ready for your vision.

  Justin Core EXP REALTY LLC

  2020 Cocos Ct, Winter Park, FL 32792
• 

  

  /39

  Est $677,000 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,488 Sq Ft

  311 E Morse Blvd Unit 6-1, Winter Park, FL 32789

  311 E Morse Blvd Unit 6-1, Winter Park, FL 32789
• 

  

  /18

  $349,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,637 Sq Ft

  1050 Reading Ct, Winter Park, FL 32792

  Under contract-accepting backup offers. Great investment opportunity in the prime location of Winter Park, Florida. Ideal for a growing family or investor. Well established neighborhood of Howell Estates, 3 bedroom, 2 full bathrooms, 1,637 square feet of living area with just over a quarter of an acre. Split plan bedrooms for added privacy. Exterior of the home is concrete block and stucco. The

  

  Carmen Vazquez

  REALTY TECH INC

  (321) 850-2823

  1050 Reading Ct, Winter Park, FL 32792
• 

  

  /85

  $1,700 - $3,548 per month

  Berkshire Winter Park

  Studio - 3 Beds

  1874 Harmon Ave, Winter Park, FL 32789

  Cultivated Living; Rooted in Style! Well-appointed Studio, One, Two, & Three Bedroom Apartment Homes in Winter Park, FL.Berkshire Winter Park is an ultra-luxury apartment community with thoughtfully curated features and enviable amenities. Select from a variety of studio, one, two, and three-bedroom floor plan schemes designed with excellence in mind. Escape ordinary; indulge in an apartment

  1874 Harmon Ave, Winter Park, FL 32789
• 

  /2

  $1,607,160 Sold Aug 01, 2025

  • 2,840 Sq Ft
  • $566/SF
  • 2 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2018

  1541 Chestnut Ave, Winter Park, FL 32789

  An extraordinary home, built in 2018 by Lazarus, is on a quaint cobblestone street in the exclusive Tree Streets of Winter Park. Contemporary transitional design has many details and has been beautifully maintained and upgraded. A four-bedroom, three-bath pool home stretches over 2,800 square feet with natural light filling the spaces through expansive windows. The home offers open concept living

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1541 Chestnut Ave, Winter Park, FL 32789
• 

  

  /43

  Est $1,808,266 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,660 Sq Ft

  1809 Harland Park Dr, Winter Park, FL 32789

  1809 Harland Park Dr, Winter Park, FL 32789
• 

  

  /23

  $525,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,191 Sq Ft

  2327 Mulbry Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Charming Mid-Century Ranch in Prime Winter Park Location – Steps from Blue Jacket Park. Ideally situated in the heart of Winter Park and just a stone’s throw from Baldwin Park’s beloved Blue Jacket Park, this tastefully updated 3 BEDROOM, PLUS OFFICE, 1.5 BATHROOM home blends timeless character with modern touches. Enjoy a freshly painted interior,

  

  Charlie Peterson

  KELLER WILLIAMS HERITAGE REALTY

  (321) 499-2363

  2327 Mulbry Dr, Winter Park, FL 32789
• 

  

  /34

  $2,600 per month

  • 3 Beds
  • 1.5 Baths
  • 1,192 Sq Ft
  • House for Rent

  1955 Bering Ave, Winter Park, FL 32789

  Welcome to this beautifully updated single-story home in sought-after Winter Park. Features 3 bedrooms and 1.5 baths, set on an oversized lot with gorgeous mature landscaping and inviting curb appeal. Inside, you'll find luxury vinyl and tile flooring throughout [no carpet] paired with recessed lighting, ceiling fans, and an abundance of natural light that enhances the bright, open living

  Linda Guzman LIV AT NONA

  1955 Bering Ave, Winter Park, FL 32789
• 

  /2

  $790,000 Sold Aug 01, 2025

  • 1,240 Sq Ft
  • $637/SF
  • 11 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1955

  1217 Kenwood Ave, Winter Park, FL 32789

  The inviting bungalow at 1217 Kenwood Ave is located just a few houses off famed Park Avenue and steps from the Winter Park Village, which is fresh off a $50 million transformation and includes popular bars and restaurants, a movie theater and shopping. The home was fully renovated in 2018 with updates to the HVAC, electrical, plumbing, flooring, subflooring, interiors, and a new roof- offering

  Kurt Lehmann LEHMANN REALTY INC.

  1217 Kenwood Ave, Winter Park, FL 32789
• 

  

  /51

  Est $1,465,946 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,922 Sq Ft

  1347 Chapman Cir, Winter Park, FL 32789

  1347 Chapman Cir, Winter Park, FL 32789
• 

  

  /45

  $1,300,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,303 Sq Ft

  1500 Mizell Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. An extraordinary opportunity to own a beautifully renovated home on a prestigious tree-lined street in Winter Park’s 32789. Set on a desirable 13,500 square foot (90 × 150) lot with no HOA and bordering the prestigious Windsong community, this prime property offers the freedom to live comfortably now, expand

  

  Lisa Ratanasirintrawoot

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 485-6636

  1500 Mizell Ave, Winter Park, FL 32789
• 

  

  /28

  $1,431 - $3,251 per month

  Cranes Landing Apartments

  1 - 3 Beds

  3440 N Goldenrod Rd, Winter Park, FL 32792

  Ready to SUMMER into your new home? Move-in Now & Pay No Rent Until September 15th and Receive Apple Airpods Pro 3 if Look & Lease*!!!2 Bedrooms Starting at $1466. CALL US AND ASK US HOW, LIMITED AVAILABLITY!! Open House Saturday, 08/02 - 10am-4pm. Now open on Sunday's from 1pm-5pm!

  3440 N Goldenrod Rd, Winter Park, FL 32792
• 

  /2

  $749,000 Sold Aug 01, 2025

  • 1,939 Sq Ft
  • $386/SF
  • 63 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2019

  1429 Indiana Ave, Winter Park, FL 32789

  Like new and totally turn-key! Built by award-winning Winter Park Custom Homes, coastal modern residence offers thoughtful design, high-end finishes, and an unbeatable location in Winter Park's coveted 32789 ZIP code. 3-bedroom, 2.5-bath home combines privacy with convenience. Minutes from Park Avenue, downtown Orlando and major local destinations. The home features authentic reclaimed

  Jennifer Sloan KELLY PRICE & COMPANY LLC

  1429 Indiana Ave, Winter Park, FL 32789
• 

  

  /13

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  700 Melrose Ave Unit M, Winter Park, FL 32789

  700 Melrose Ave Unit M, Winter Park, FL 32789
• 

  

  /50

  $489,000

  • 3 Beds
  • 3 Baths
  • 1,880 Sq Ft

  2835 Bongart Rd, Winter Park, FL 32792

  Motivated Seller - Welcome to your spectacular pool home in Winter Park Estates. This beautifully renovated 3-bedroom, 3-bath residence features all the modern upgrades you've been searching for inside and out! Enjoy peace of mind with a new A/C unit (warranty included) and resurfaced pool complete with a new pump—perfect for Florida living. The backyard features fresh SOD, while the gables and

  

  Claudia Jenkins

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 450-7314

  2835 Bongart Rd, Winter Park, FL 32792
• 

  

  /9

  $1,500 per month

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • Condo for Rent

  3651 N Goldenrod Rd Unit 103, Winter Park, FL 32792

  Beautiful ground floor unit with all tile flooring! This 2 bed/2 bath has an open floor plan. The kitchen is open to the living room and dining area and features all appliances, granite counter, a breakfast bar and sliding glass doors to the patio, Both bedrooms are good size. Both bathrooms have been updated. Inside utility with a Stackable Washer and Dryer. Tenants are REQUIRED to have renters

  Kelly Carr CFRP REALTY LLC

  3651 N Goldenrod Rd Unit 103, Winter Park, FL 32792
• 

  /2

  $505,000 Sold Aug 01, 2025

  • 2,250 Sq Ft
  • $224/SF
  • 60 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1968

  715 Roughbeard Rd, Winter Park, FL 32792

  Price Improvement! Enjoy Winter Park living on this quiet street, with no thru traffic. This home is the perfect opportunity to live in the coveted neighborhood of WINTER PARK PINES. This 4 bedroom, 2 bath POOL home is a well-built traditional home waiting for its next owner. The ROOF was replaced in 2024 and the remaining home is waiting for your personal touch. The oversize Florida room has

  Christine Gerardi NEXTHOME DIAMOND PROPERTIES

  715 Roughbeard Rd, Winter Park, FL 32792
• 

  

  /12

  Not Listed For Sale

  • 4 Beds
  • 2,291 Sq Ft

  2506 Argyll Cove, Winter Park, FL 32792

  2506 Argyll Cove, Winter Park, FL 32792
• 

  

  /8

  $260,000

  • Land
  • 0.81 Acre
  • $320,988 per Acre

  3580 Wilde Ave, Winter Park, FL 32792

  Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just shy of an acre, lot in coveted Winter Park. Nestled on a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level lot on a

  

  Gwendolen Flynn

  COLDWELL BANKER RESIDENTIAL RE

  (321) 334-2867

  3580 Wilde Ave, Winter Park, FL 32792
• 

  

  /103

  $1,972 - $6,231 per month

  Paseo at Winter Park Village

  1 - 3 Beds

  940 W Canton Ave, Winter Park, FL 32789

  Ready for an apartment home that truly feels like home? With upscale finishes and modern amenities, Paseo's units are ready to welcome you. You (and your pet!) can relax in our palm-lined courtyard, lounge by the pool, or play in our on-site dog park. With the shopping of Winter Park Village, movies at the Regal Cinema, and the historic downtown all close by, there are endless opportunities to

  940 W Canton Ave, Winter Park, FL 32789
• 

  /2

  $265,000 Sold Jul 31, 2025

  • 1,236 Sq Ft
  • $214/SF
  • 8 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1984

  5164 Lazy Oaks Dr, Winter Park, FL 32792

  Absolutely charming 2-bedroom, 2.5-bathroom townhome style condo in the heart of Winter Park with a brand new roof! As you enter the front door, you are greeted with the expansive, open design of the first floor that extends all the way through the bonus office room and into the grassy courtyard! The kitchen has been updated with new counter tops, a double sink, and wonderful, little coffee bar

  Jeremy Wood KELLER WILLIAMS HERITAGE REALTY

  5164 Lazy Oaks Dr, Winter Park, FL 32792
• 

  

  /44

  Est $894,432 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,602 Sq Ft

  436 W Swoope Ave, Winter Park, FL 32789

  436 W Swoope Ave, Winter Park, FL 32789

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