Orange, FL Homes

• 

  

  

  /37

  $679,900

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft

  1640 Cypress Point Ln, Winter Park, FL 32792

  Welcome to 1640 Cypress Point – a home like no other in Winter Park. This beautifully maintained 3-bedroom, 2-bathroom home offers 1,704 sq. ft. overlooking a serene spring-fed pond and the Winter Park Pines Golf Course. Nestled on a quiet street with a cul-de-sac, this property combines privacy, natural beauty, and convenience in one exceptional location. As you walk up to the front door, you’ll

  Amy Turner KELLER WILLIAMS WINTER PARK

  1640 Cypress Point Ln, Winter Park, FL 32792
• 

  

  

  /39

  $903 - $1,535 per month

  San Jose Apartments

  1 - 3 Beds

  2353 Winter Woods Blvd, Winter Park, FL 32792

  Come home to San Jose Apartments and enjoy the advantages of spacious apartments and ample parking. We have a wide variety of living spaces to choose from, all with large closets and modern amenities. You'll love our beautiful swimming pool and clubhouse. Call today to make San Jose Apartments your new home.TDD:711 for hearing impaired assistance.

  2353 Winter Woods Blvd, Winter Park, FL 32792
• 

  

  /2

  $192,000 Sold Jul 16, 2025

  • 1,059 Sq Ft
  • $181/SF
  • 40 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  4878 Tangerine Ave, Winter Park, FL 32792

  WATCH REAL VIDEO & 3D TOUR! Welcome to 4878 Tangerine Ave, a beautifully MOVE IN READY- NEW ROOF - NEW FLOORS- FRESH PAINT updated 2-bedroom, 2-bathroom condo nestled in the serene and highly desirable Wrenwood Condominiums of Winter Park with Community POOL/GYM and ample parking. Yard maintenance, Roof replacement, Trash, and Water are included in the HOA. Step inside and be greeted by

  Arthur Love LA ROSA REALTY ORLANDO LLC

  4878 Tangerine Ave, Winter Park, FL 32792
• 

  

  

  /25

  Est $222,233 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,127 Sq Ft

  200 Saint Andrews Blvd Unit 2808, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 2808, Winter Park, FL 32792
• 

  

  

  /39

  $699,900

  • 3 Beds
  • 3 Baths
  • 1,876 Sq Ft

  618 Blairshire Cir, Winter Park, FL 32792

  First time on the market! This one-owner, 3-bedroom, 3-bathroom single-family pool home offers the perfect blend of classic Florida charm and modern potential. Originally named The Polynesia, the home embraces open Florida living while offering distinct zones for privacy and comfort. A brand-new roof (2025) and 2 New HVAC 2024 provides peace of mind and a strong foundation for move-in readiness —

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  618 Blairshire Cir, Winter Park, FL 32792
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  /30

  $4,000 per month

  • 4 Beds
  • 3 Baths
  • 2,818 Sq Ft
  • House for Rent

  1289 Heavenly Cove, Winter Park, FL 32792

  Welcome to this move in ready 4-bedroom, 3-bath, 3-car garage pool home located in the exclusive gated community of Eden Point, a desirable Winter Park address! From the moment you arrive, you'll be impressed by the gorgeous elevation, paver driveway, and inviting front porch. This home offers a thoughtful split floor plan, tray ceilings, and rich Bamboo floors, creating a sense of space and

  Shahrin Alam COLDWELL BANKER RESIDENTIAL RE

  1289 Heavenly Cove, Winter Park, FL 32792
• 

  /2

  $285,123 Sold Jul 15, 2025

  • 1,310 Sq Ft
  • $218/SF
  • 24 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  5588 Garden Grove Cir, Winter Park, FL 32792

  Location, Location, Location! This 3-bedroom, 2-bathroom gem is perfect for families and offers everything you need to feel right at home. This one boasts a Great Room Plan that’s perfect for entertaining! The gally kitchen has a Breakfast Bar and overlooks the dining area and great room. The home offers a 3-way split The Master Suite has with Stall Shower and laminate flooring. You’ll also find

  Joyce Sanders FLORIDA REAL ESTATE PROPERTIES LLC

  5588 Garden Grove Cir, Winter Park, FL 32792
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  /33

  Est $487,722 Not Listed For Sale

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

  2260 Shadowland Loop, Winter Park, FL 32792

  2260 Shadowland Loop, Winter Park, FL 32792
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  /36

  $750,000 Open Sat 12PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,256 Sq Ft

  2478 Whitehall Cir, Winter Park, FL 32792

  Expect to be impressed with this updated 3BR home in one of Winter Park’s well-established neighborhoods. It starts with great curb appeal – meticulously manicuredfront lawn, decorative paver stones surrounding the entryway and a 3-car garage! Stepinside to space originally designed as formal living and dining rooms – versatile toarrange as you see fit. Walk back to the “WOW

  Erica Magtira LPT REALTY, LLC

  2478 Whitehall Cir, Winter Park, FL 32792
• 

  

  /11

  $1,178 - $1,626 per month

  Solis at Winter Park

  1 - 2 Beds

  7502 Sun Key Blvd, Winter Park, FL 32792

  Property Tours AvailableWe are now welcoming virtual, self-guided, and agent led tours. Please contact us today to schedule your appointment.Solis at Winter Park, FL Apartments boast premier location great for both business and leisure. The wide selection of one and two bedroom apartments ensure you will find a layout that fits your needs perfectly. Every apartment home comes decked out with huge

  7502 Sun Key Blvd, Winter Park, FL 32792
• 

  /2

  $400,000 Sold Jul 15, 2025

  • 1,704 Sq Ft
  • $235/SF
  • 23 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1974

  1017 Manchester Cir, Winter Park, FL 32792

  Under contract-accepting backup offers. Seller will assist with closing costs! Welcome to your dream home in the highly sought-after Howell Estates community of Winter Park, Florida! This immaculate four-bedroom, two-bathroom residence is perfectly situated on just under a quarter acre, surrounded by lush, mature landscaping that enhances its curb appeal. Step inside this well-maintained gem,

  Jenaia Fowlkes FOWLKES REALTY CO

  1017 Manchester Cir, Winter Park, FL 32792
• 

  /2

  Est $706,268 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,416 Sq Ft

  1360 Blue Stem Ln, Winter Park, FL 32792

  1360 Blue Stem Ln, Winter Park, FL 32792
• 

  

  /21

  $630,000

  • 4 Beds
  • 2.5 Baths
  • 2,267 Sq Ft

  7988 Pleasant Pine Cir, Winter Park, FL 32792

  Stylish, Updated & Move-In Ready in Gated Winter Park Community!Welcome to this impeccably maintained 4-bedroom, 2.5-bath home offering nearly 2,300 square feet of thoughtfully designed living space in the desirable Enclave at Aloma. From the charming covered front porch to the spacious screened lanai, every detail of this home has been crafted with comfort, style, and functionality in

  David Teller ABSOLUTE REALTY GROUP, LLC

  7988 Pleasant Pine Cir, Winter Park, FL 32792
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  /24

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft
  • Condo for Rent

  3045 Aaron Burr Ave Unit 12, Winter Park, FL 32792

  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 2 bedroom is perfect for a quick access to all that Orlando has. New FLOOR and a clean fresh home to make a perfect lifestyle for anyone, properties),, move-in concierge

  Angel Ramirez LPT REALTY, LLC

  3045 Aaron Burr Ave Unit 12, Winter Park, FL 32792
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  /2

  $266,000 Sold Jul 15, 2025

  • 1,092 Sq Ft
  • $244/SF
  • 25 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1985

  5518 Cretan Way, Winter Park, FL 32792

  This charming 2-bedroom, 2-bath townhome in the quiet and friendly Fernbrook Trails community in Winter Park is ready for it's new owner. This one-story home has a warm, open feel with wood-look tile flooring throughout. The kitchen has everything you need—stainless steel appliances, a closet pantry, and tons of cabinet and counter space—and it opens right up to the dining area, making it great

  Liam Pool HOMEVEST REALTY

  5518 Cretan Way, Winter Park, FL 32792
• 

  

  /18

  Est $215,955 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft

  3351 River View Way Unit 41, Winter Park, FL 32792

  3351 River View Way Unit 41, Winter Park, FL 32792
• 

  

  /26

  $209,500

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft

  3370 Cedar Springs Place Unit 156, Winter Park, FL 32792

  Ideally situated just minutes from Full Sail University, UCF, and major retailers, this well-appointed 2-bedroom, 2.5-bath townhome-style condo offers both comfort and convenience. The main floor features a spacious living and dining area with a breakfast nook, a guest half bath, and updated appliances. Upstairs, you’ll find two generously sized master suites, each with its own private bathroom.

  Qing Lin SPRINGHILL PROPERTIES LLC

  3370 Cedar Springs Place Unit 156, Winter Park, FL 32792
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  /35

  $1,579 - $1,899 per month

  The Vista at Winter Park

  2 Beds

  4704 Lucier Ct, Winter Park, FL 32792

  Move in special- $300 on move in!*Restricted units only*Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!In a prime location of Winter Park, you will find our small and great community!Keeping the calm and great atmosphere, being able to relax by the lake, and being moments from shopping, dining, andmore, Set a tour today, and you will find

  4704 Lucier Ct, Winter Park, FL 32792
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  /2

  $82,000 Sold Jul 15, 2025

  • 1,020 Sq Ft
  • $80/SF
  • 0 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  186 Scottsdale Square Unit F186, Winter Park, FL 32792

  Beautiful and well maintained 2 bedroom 2 bath condo. Located close to Full sail University. Stainless Steel appliances. New A/C February 2024. Condo was recently remodeled in October 2023 (all new kitchen - cabinets and appliances, new floors, new vanities in the bathrooms, new light fixtures. Easy access to major roads and highways. Beautiful outdoor area, playground, and pool.

  John Harbuck FANNIE HILLMAN & ASSOCIATES

  186 Scottsdale Square Unit F186, Winter Park, FL 32792
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  /60

  Est $886,528 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,057 Sq Ft

  2044 Wood Thrush Ln, Aloma, FL 32792

  2044 Wood Thrush Ln, Aloma, FL 32792
• 

  

  /39

  $525,000

  • 4 Beds
  • 2 Baths
  • 1,508 Sq Ft

  2844 Scarlet Rd, Winter Park, FL 32792

  Welcome to this stunning mid-century modern beauty where timeless design meets thoughtful, contemporary updates. Nestled in the highly sought-after neighborhood of Winter Park Pines, this 4-bedroom, 2-bathroom home offers over 1,500 sq ft of stylish, functional living space—and yes, your mail is still delivered to the front door! Step through a tastefully renovated entryway into an open, airy

  Amy Turner KELLER WILLIAMS WINTER PARK

  2844 Scarlet Rd, Winter Park, FL 32792
• 

  

  /14

  $2,350 per month

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft
  • House for Rent

  5323 Poinsetta Ave, Winter Park, FL 32792

  Winter Park and NO HOA!! Newly remodeled 3/2 1,500 sqft $2,350/mo. Just a 1 minute car ride or 5-7 minute walk to Eastbrook Elementary. Remodeled kitchen with all the bells and whistles (new cabinets, countertops, backsplash, faucet, lights, and appliances - you get the idea, it's fancy!). Remodeled bathrooms with subway tiles, new tub, new vanities, new countertops, new toilets, new lighting &

  Ginnie England MAGNOLIA PROPERTY SALES

  5323 Poinsetta Ave, Winter Park, FL 32792
• 

  /2

  $50,000 Sold Jul 15, 2025

  • 590 Sq Ft
  • $85/SF
  • 105 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1974

  7309 Daniel Webster Dr Unit D, Winter Park, FL 32792

  Priced to sell! Turnkey Investment Opportunity in Winter Park!Attention investors and savvy buyers—this 1-bedroom, 1-bath condo in the Colonies Condo community is the perfect low-maintenance, high-potential opportunity! With 610 sq. ft. of efficient living space, this unit is ideal for a young professional, student, or tenant looking for affordability in a prime location. Featuring vinyl

  Benjamin Berry EXP REALTY LLC

  7309 Daniel Webster Dr Unit D, Winter Park, FL 32792
• 

  

  /42

  Est $489,904 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  2444 Firstlight Way, Winter Park, FL 32792

  2444 Firstlight Way, Winter Park, FL 32792
• 

  

  /38

  $590,000

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft

  8065 Pleasant Pine Cir, Winter Park, FL 32792

  **This property qualifies for a closing cost credit up to $8,800 through the Seller’s preferred lender.**Welcome home to this beautifully maintained 4-bedroom, 2-bathroom home nestled on a serene conservation lot in the heart of Winter Park. As you step inside, you’ll find two guest bedrooms at the front of the home with a full bathroom conveniently situated between them. Down the hallway is the

  Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  8065 Pleasant Pine Cir, Winter Park, FL 32792
• 

  

  /30

  $1,802 - $2,691 per month

  Rosalia Winter Park 55+ Active Adult Commu...

  1 - 2 Beds

  3045 Aloma Ave, Winter Park, FL 32792

  Browse our 1 and 2-bedroom luxury 55+ apartments at Rosalia Winter Park, complete with modern appliances and stunning finishes. Stay connected and engaged with countless luxury amenities and activities designed for your lifestyle by our dedicated onsite management team and exciting amenities, including a clubhouse, fitness center, and robust social calendar—all with an attentive team at your

  3045 Aloma Ave, Winter Park, FL 32792
• 

  /2

  $125,000 Sold Jul 14, 2025

  • 802 Sq Ft
  • $156/SF
  • 5 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1983

  7344 Swallow Run Unit 7344, Winter Park, FL 32792

  Step into this beautiful 2-bedroom, 2-bathroom condo, freshly painted and filled with natural light throughout. The open-concept floor plan is perfect for entertaining, while the split-bedroom layout ensures added privacy for residents or guests.The primary suite features a walk-in shower, ample storage, and a private en-suite bath. Enjoy serene views of lush green space and located in

  Merigan Barton DON HARKINS REALTY LLC

  7344 Swallow Run Unit 7344, Winter Park, FL 32792
• 

  /2

  Est $225,421 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft

  200 Saint Andrews Blvd Unit 3610, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 3610, Winter Park, FL 32792
• 

  

  /23

  $174,900

  • 1 Bed
  • 1 Bath
  • 727 Sq Ft

  200 St Andrews Blvd Unit 601, Winter Park, FL 32792

  Welcome to this spacious and beautifully updated first-floor condo with 1 bedroom, 1 bathroom in the heart of Winter Park, the highly sought after Four Seasons community. This unit offers the convenience of walk-up access and a covered carport just steps from your private screened patio and laundry inside the unit. The kitchen was remodeled in 2021 and features white shaker-style cabinetry, a

  Amy Turner KELLER WILLIAMS WINTER PARK

  200 St Andrews Blvd Unit 601, Winter Park, FL 32792
• 

  

  /13

  $3,095 per month

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Townhouse for Rent

  3486 Bougainvillea Dr Unit B, Winter Park, FL 32792

  Location! Location! Location! This exactly what you are looking for, a nice home in a great location. This a great unit featuring a nice kitchen with stainless steel appliances, and an updated flooring with luxury vinyl plank. This unit has an indoor heated swimming pool with an exercise room. This property is located near all of the main central Florida colleges. Come and enjoy with your family

  Smithj Salomon LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  3486 Bougainvillea Dr Unit B, Winter Park, FL 32792
• 

  /2

  $290,000 Sold Jul 14, 2025

  • 1,020 Sq Ft
  • $284/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1977

  2541 Leeward Way, Winter Park, FL 32792

  Discover One of Winter Park’s Best-Kept Secrets — Windward Square!Welcome to your beautifully renovated 2-bedroom, 2-bath townhome in the highly sought-after Windward Square community. This move-in ready home boasts a bright, open floor plan, with a modern kitchen that flows effortlessly into the spacious living area.The fully updated kitchen features brand-new stainless steel

  Jason Howell REAL BROKER, LLC

  2541 Leeward Way, Winter Park, FL 32792
• 

  

  /38

  Est $758,498 Not Listed For Sale

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

  1477 Lone Feather Trail, Winter Park, FL 32792

  1477 Lone Feather Trail, Winter Park, FL 32792
• 

  

  /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
• 

  

  /31

  $1,550 - $1,859 per month

  POSTE Winter Park

  1 - 2 Beds

  800 Semoran Park Dr, Winter Park, FL 32792

  Welcome to Poste Winter Park, where the beauty of classic period architecture meets the modern comforts of today. Nestled in the heart of trendy Winter Park, Florida, our community is your gateway to a vibrant, convenient, and tranquil lifestyle. Poste Winter Park offers a boutique feel with newly remodeled facilities, spacious floor plans, and signature customer service. Located just across from

  800 Semoran Park Dr, Winter Park, FL 32792
• 

  /2

  $365,000 Sold Jul 14, 2025

  • 1,368 Sq Ft
  • $267/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  1748 Harvest Cove, Winter Park, FL 32792

  Tucked away in a quiet Winter Park cul-de-sac, this 3-bedroom, 2-bathroom home sits in one of the area’s most convenient spots with low taxes, low HOA, and access to top-rated schools.The layout flows well, with updated bathrooms, an enclosed porch for extra living space, and a backyard that’s great for entertaining. There’s even a partial pond view that adds a little extra charm. Whether

  Matt Anderson EXP REALTY LLC

  1748 Harvest Cove, Winter Park, FL 32792
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,079 Sq Ft

  3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792

  3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792
• 

  

  /74

  $600,000

  • 4 Beds
  • 2 Baths
  • 2,433 Sq Ft

  8248 Marbella View Ct, Orlando, FL 32817

  Absolutely stunning and fully renovated, this pool home offers high-end finishes, an open layout, and an unbeatable location. Tucked away on a quiet cul-de-sac, it features exceptional curb appeal and a unique extended driveway—providing additional parking with paved access to both the garage and front entry.Inside, the home offers a bright, open floor plan with tile throughout,

  Gnesa Fray INTERMIX REAL ESTATE INC

  8248 Marbella View Ct, Orlando, FL 32817
• 

  

  /13

  $2,395 per month

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Townhouse for Rent

  3486 Bougainvillea Dr Unit A, Winter Park, FL 32792

  Nice house with 2 units in a great location and each unit is being rent separately. This property is located in the heart of Winter Park where everything is close by. This unit has great value and is near all of the main colleges. Come and enjoy this unit with your family and friends. Please schedule your showing today before it is gone.

  Smithj Salomon LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  3486 Bougainvillea Dr Unit A, Winter Park, FL 32792
• 

  /2

  $705,000 Sold Jul 14, 2025

  • 2,385 Sq Ft
  • $296/SF
  • 57 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1979

  1139 Fairway Dr, Winter Park, FL 32792

  NEW LOWER PRICE 6/3/25, OWNER WANTS OFFERS. NO HOA. Fabulous RENOVATED home in the heart of Winter Park, where timeless charm meets tranquil Winter Park Pines golf course living. Nestled on a lush, manicured lot right on the 9th fairway, this expansive REMODELLED OPEN AND AIRY SPLIT-plan residence offers a SPLIT PLAN WITH 4 generously sized bedrooms, 2 full baths, and FABULOUS FLEX SPACE that

  Gale Milgrim KELLER WILLIAMS WINTER PARK

  1139 Fairway Dr, Winter Park, FL 32792
• 

  /2

  Est $478,761 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  Unlisted Address

  Unlisted Address

Showing Results 121 - 160, Page 4 of 18