Orange, FL Homes

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  /47

  $725,000 Open Sat 10AM - 12PM

  • 5 Beds
  • 3.5 Baths
  • 3,568 Sq Ft

  7895 Pleasant Pine Cir, Winter Park, FL 32792

  Seller Motivated! Bring any and all offers.Welcome to Your Dream Home in Enclave at Aloma, Winter Park!Step into this stunningly maintained 5-bedroom, 3.5-bathroom residence located in the highly sought-after gated community of Enclave at Aloma. Perfectly positioned with no rear neighbors, this home offers ultimate privacy and tranquility.As you enter, you’ll immediately

  Yvette Hoover ALL REAL ESTATE & INVESTMENTS

  7895 Pleasant Pine Cir, Winter Park, FL 32792
• 

  

  

  /10

  $2,190 per month

  • 3 Beds
  • 2 Baths
  • 1,701 Sq Ft
  • House for Rent

  1305 Viburnum Ln, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2309.90. That covers your base rent, $2165.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1305 Viburnum Ln, Winter Park, FL 32792
• 

  

  /2

  $550,000 Sold Jun 24, 2025

  • 1,856 Sq Ft
  • $296/SF
  • 68 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  2310 Cady Way, Winter Park, FL 32792

  Welcome home to the sought after neighborhood of Brookshire Heights with in the Greater Winter Park Pines Community, where tree-lined streets and the friendly touch of a neighborhood where the mailman still delivers to your door await you! This spacious and updated 3-bedroom, 2-bathroom home is an entertainer’s dream, offering a perfect blend of modern updates, cozy living spaces, and serene

  Amy Turner KELLER WILLIAMS WINTER PARK

  2310 Cady Way, Winter Park, FL 32792
• 

  

  

  /22

  Est $226,418 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  200 Saint Andrews Blvd Unit 1902, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 1902, Winter Park, FL 32792
• 

  

  

  /55

  $1,149,000

  • 4 Beds
  • 4.5 Baths
  • 3,408 Sq Ft

  2890 Wild Ginger Ct, Winter Park, FL 32792

  Discover the exceptional Winter Park neighborhood of Bear Gully Pointe, a gated community rich with amenities and anchored by a 137-acre spring-fed lake. This meticulously crafted home sits in a private cul-de-sac and stretches over almost 1⁄2 acre with mature landscaping and includes a secluded, fenced back yard. Function is paramount with a three-way split floorplan with four bedrooms and 4.5

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  2890 Wild Ginger Ct, Winter Park, FL 32792
• 

  

  /19

  $1,649 per month

  • 2 Beds
  • 2.5 Baths
  • 1,090 Sq Ft
  • Condo for Rent

  3007 George Mason Ave Unit H-3D, Winter Park, FL 32792

  Move-in ready and beautifully updated, this two-story condo in the desirable Colonies Community offers 2 bedrooms and 2.5 bathrooms, with each bedroom featuring its own private en-suite bath. All bedrooms are located upstairs. While a convenient half bath is located on the first floor. The home features fresh interior paint, new flooring in many rooms, and numerous upgrades throughout. The

  Alex Zweydoff ALLEGIANT MANAGEMENT GROUP INC

  3007 George Mason Ave Unit H-3D, Winter Park, FL 32792
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  /2

  $400,000 Sold Jun 24, 2025

  • 2,124 Sq Ft
  • $188/SF
  • 47 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1972

  4991 Tangerine Ave, Winter Park, FL 32792

  Welcome to 4991 Tangerine Ave in the heart of Winter Park! This charming 4-bedroom, 2-bathroom home offers comfortable living with no carpet throughout—perfect for easy maintenance. The spacious family and dining room combination provides an open and inviting layout, ideal for gatherings. A large, air-conditioned Florida room adds even more flexibility, ensuring plenty of space for entertaining.

  Darein Washington KELLER WILLIAMS ADVANTAGE REALTY

  4991 Tangerine Ave, Winter Park, FL 32792
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  /77

  Est $792,308 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,496 Sq Ft

  7904 Pleasant Pine Cir, Winter Park, FL 32792

  7904 Pleasant Pine Cir, Winter Park, FL 32792
• 

  

  /42

  $499,999

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  1924 Summerfield Rd, Winter Park, FL 32792

  **This property qualifies for a closing cost credit up to $7,700 through the Seller’s preferred lender.** Welcome to a lovingly maintained home where charm, comfort, and a sense of history come together in the heart of Winter Park. Nestled on a quiet street in the 32792 zip code, this 3-bedroom, 2-bath gem is the kind of place where memories are made and every room tells a story. As you pull into

  Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  1924 Summerfield Rd, Winter Park, FL 32792
• 

  

  /17

  $2,695 per month

  • 3 Beds
  • 2.5 Baths
  • 2,378 Sq Ft
  • House for Rent

  1427 Broad Wing Ln, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2754.90. That covers your base rent, $2695.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Smart

  1427 Broad Wing Ln, Winter Park, FL 32792
• 

  /2

  $72,000 Sold Jun 24, 2025

  • 785 Sq Ft
  • $92/SF
  • 4 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1974

  273 Scottsdale Square Unit 273, Winter Park, FL 32792

  Located on the First Floor, this single-story condo features a one bedroom and one bathroom layout with a Foyer, Formal Dining and Living room with laminate flooring, Quaint Kitchen, Updated Bathroom and a Spacious Primary Bedroom with laminate flooring. In addition this condo includes a covered front porch and covered outdoor patio space with views of greenery. The unit has a private Laundry

  Erin Tompkins COLDWELL BANKER RESIDENTIAL RE

  273 Scottsdale Square Unit 273, Winter Park, FL 32792
• 

  

  /22

  Est $691,407 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,197 Sq Ft

  1316 Blue Stem Ln, Aloma, FL 32792

  1316 Blue Stem Ln, Aloma, FL 32792
• 

  

  /27

  $410,000

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

  4959 Ardmore Dr, Winter Park, FL 32792

  Tucked away at the end of a quiet cul-de-sac with no HOA, this home sits on an oversized lot that offers exceptional space, privacy, and flexibility. The layout features a desirable split floor plan, providing separation between the primary suite and guest bedrooms, perfect for families, guests, or a home office setup. This property was recently updated with new flooring throughout, a fully

  Brandon Geers COMPASS FLORIDA LLC

  4959 Ardmore Dr, Winter Park, FL 32792
• 

  

  /9

  $780,000 per month

  • Property for Rent

  7839 University Garden Dr, Winter Park, FL 32792

  Build your dream home on 4.93 acres in Winter Park. No HOA, lot dimensions 665ft x 323ft, zoning A-2/FARMLAND RURAL, land use vacant residential. The sale price included 2 parcels 11 22 30 0000 00 125 & 11 22 30 0000 00 042 with a factory home 3/2, 1344 sf. heated, built in 1976, and a mobile home. Convenient to SR-551/ Goldenrod Rd, SR-426/Aloma Rd, SR-50/Colonial Dr, University Blvd, FL-417,

  Shettle Huynh FLORIDA REALTY INVESTMENTS

  7839 University Garden Dr, Winter Park, FL 32792
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  /2

  $468,470 Sold Jun 20, 2025

  • 1,724 Sq Ft
  • $272/SF
  • 25 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1977

  1026 Manchester Cir, Winter Park, FL 32792

  Welcome to your private oasis—where thoughtfully designed living spaces and beautiful upgrades come together in one incredible home. Whether it’s poolside afternoons, entertaining under the lanai, or cozy nights inside, this property delivers the Florida lifestyle you’ve been searching for. Step inside this well-maintained split floor plan home and enjoy a spacious family room that flows

  David Miller KELLER WILLIAMS HERITAGE REALTY

  1026 Manchester Cir, Winter Park, FL 32792
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  /28

  Est $305,565 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft

  7113 Swallow Run Unit 2, Winter Park, FL 32792

  7113 Swallow Run Unit 2, Winter Park, FL 32792
• 

  

  /34

  $484,900

  • 3 Beds
  • 2 Baths
  • 1,906 Sq Ft

  1173 Valley Creek Run, Winter Park, FL 32792

  Welcome to this beautifully maintained 3-bedroom, 2-bath home offering 1,906 square feet of comfortable living space in the heart of Winter Park. Built in 1995, this home features a desirable split-bedroom floor plan, high ceilings, and tile flooring throughout the main living areas—perfect for everyday living and entertaining. The spacious layout includes both a formal living room and a separate

  Rebeka Weeks LUKER & CO REAL ESTATE LLC

  1173 Valley Creek Run, Winter Park, FL 32792
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  /2

  $2,160 per month

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • House for Rent

  1061 Portsmouth Ln, Winter Park, FL 32792

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

  1061 Portsmouth Ln, Winter Park, FL 32792
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  /2

  $82,000 Sold Jun 20, 2025

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

  • 2 Beds
  • 2 Baths
  • Built 1974

  185 Scottsdale Square Unit F185, Winter Park, FL 32792

  Beautifully maintained and updated 2 Bedroom and 2 Bath condo in Winter Park! Easy to care for tile floors flow through the kitchen, living, and dining areas. The kitchen features a tile backsplash, newer stainless steel appliances, and cabinets with decorative glass inserts. An open concept living and dining area is bright with a large slider that opens to a private patio. Each bedroom features

  Erin Baker FANNIE HILLMAN & ASSOCIATES

  185 Scottsdale Square Unit F185, Winter Park, FL 32792
• 

  

  /17

  Est $462,051 Not Listed For Sale

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

  2760 Bright Bird Ln, Winter Park, FL 32792

  2760 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /24

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,518 Sq Ft

  3107 Ash Park Loop, Winter Park, FL 32792

  The popular Hyde Park community welcomes you to your new home. If you are looking for a private, 3/2 with enclosed backyard with view of trees, then look no further. Ideally located to Downtown Winter Park, UCF, Casselberry, and Winter Springs. Restaurants and shopping nearby as well. Enjoy the community amenities, including playground, tennis and basketball courts, sidewalks throughout and a

  Jean Miller COLDWELL BANKER REALTY

  3107 Ash Park Loop, Winter Park, FL 32792
• 

  

  /9

  $2,700 per month

  • 3 Beds
  • 2.5 Baths
  • 1,700 Sq Ft
  • Townhouse for Rent

  2749 Bright Bird Ln, Winter Park, FL 32792

  Like New! Townhouse in a very calm and central community in Winter Park, excellent schools, great location! Clubhouse with pool for residents.

  Juan Rubio REALTY ONE GROUP EVOLUTION

  2749 Bright Bird Ln, Winter Park, FL 32792
• 

  /2

  $205,000 Sold Jun 20, 2025

  • 1,059 Sq Ft
  • $194/SF
  • 97 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  4944 Tangerine Ave, Winter Park, FL 32792

  Welcome to this delightful 2-bedroom, 2-bath end-unit condominium, offering the perfect blend of comfort and style! As you enter, you’re greeted by a charming foyer with a convenient coat closet, setting the tone for this spacious and inviting home. The expansive living/dining area is perfect for both everyday living and entertaining guests. A newer sliding glass door leads to a peaceful screened

  Christine David WATSON REALTY CORP

  4944 Tangerine Ave, Winter Park, FL 32792
• 

  

  /18

  Est $236,264 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft

  7413 Belle River Ct Unit 3, Winter Park, FL 32792

  7413 Belle River Ct Unit 3, Winter Park, FL 32792
• 

  

  /40

  $500,000

  • 4 Beds
  • 2.5 Baths
  • 2,075 Sq Ft

  Unlisted Address

  Welcome to this beautifully maintained 4-bedroom, 2.5-bath pool home nestled in a peaceful neighborhood. This two-story gem offers a spacious and functional layout perfect for both relaxing and entertaining. The 1st floor master is spacious and inviting. Enjoy peace of mind with a newer roof and windows, as well as brand-new laminate flooring throughout the main living areas. Upstairs, a

  Luke Lewis TREASURE COAST REALTY GROUP, LLC

  Unlisted Address
• 

  

  /15

  $1,935 per month

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • House for Rent

  1381 Viburnum Ln, Winter Park, FL 32792

  We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be

  1381 Viburnum Ln, Winter Park, FL 32792
• 

  /2

  $665,000 Sold Jun 18, 2025

  • 2,183 Sq Ft
  • $305/SF
  • 37 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1963

  2817 Prince John Rd, Winter Park, FL 32792

  NEW ROOF 2019! GREAT PRICE! SPECTACULAR WINTER PARK HOME COMPLETELY RENOVATED AND UPGRADED INCLUDING A STUNNING KITCHEN! This four bedroom three and a half bath home has been meticulously updated and cared for! It has PORCELAIN WOOD LOOK TILE and WOOD flooring THROUGHOUT and NO CARPET. When you walk in the front door you are greeted by a grand and open design. This one-story home even has an IN

  Lori Gilmore LORI GILMORE REAL ESTATE LLC

  2817 Prince John Rd, Winter Park, FL 32792
• 

  

  /5

  Est $456,029 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,477 Sq Ft

  7494 Betty St, Winter Park, FL 32792

  7494 Betty St, Winter Park, FL 32792
• 

  

  /70

  $472,000 Open Sat 10AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,623 Sq Ft

  2648 Amsden Rd, Winter Park, FL 32792

  Beautiful Pool Home in Desirable Winter Park EstatesWelcome to this charming and thoughtfully updated pool home in the highly sought-after Winter Park Estates subdivision—zoned for top-rated schools, including Winter Park High School. This mid-century gem blends modern comfort with timeless style, located in one of Central Florida’s most beloved neighborhoods.Property

  Mary Dees CHOICEPOINTE REALTY, INC.

  2648 Amsden Rd, Winter Park, FL 32792
• 

  

  /20

  $3,400 per month

  • 3 Beds
  • 1.5 Baths
  • 1,409 Sq Ft
  • House for Rent

  532 Darcey Dr, Winter Park, FL 32792

  This 3 bedroom/1.5 bathroom CORNER lot home is located in the desirable Brookshire Heights neighborhood. The home was redesigned in 2020 and has since been upgraded even further! No detail was overlooked in this adorable midcentury home. Brand new roof completely replaced in 2023 with new fascia, soffits, and gutters. Exterior just painted in 2023. Newly remodeled kitchen features Quartz

  Wenwen Wang JWJ REALTY LLC

  532 Darcey Dr, Winter Park, FL 32792
• 

  /2

  $630,000 Sold Jun 18, 2025

  • 1,670 Sq Ft
  • $377/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  2707 Prince John Rd, Winter Park, FL 32792

  Welcome home to the Winter Park Pines with its tree-lined streets and where the mailman still delivers to your door! Nestled on a large corner lot, this beautifully and meticulously renovated 3-bedroom, 2-bathroom (PLUS AN OFFICE) home is an entertainer’s dream, perfectly blending comfort, functionality, and style. Step inside to discover a chef’s kitchen that will impress even the most

  Amy Turner KELLER WILLIAMS WINTER PARK

  2707 Prince John Rd, Winter Park, FL 32792
• 

  /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
• 

  

  /25

  $299,900

  • 3 Beds
  • 1 Bath
  • 1,114 Sq Ft

  7102 Easter St, Winter Park, FL 32792

  Welcome to a Rare Gem in Winter Park!Step into a vibrant slice of Winter Park history at 7102 Easter Street—a charming 1956-built home bursting with vintage character and endless possibilities! From the moment you arrive, you'll feel the warmth and nostalgia of this beautifully maintained residence, where classic mid-century style meets modern-day potential.Inside, you’ll find 3

  Mayken Giraldo CHARLES RUTENBERG REALTY ORLANDO

  7102 Easter St, Winter Park, FL 32792
• 

  

  /15

  $1,920 per month

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  5335 N Orange Ave, Winter Park, FL 32792

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  5335 N Orange Ave, Winter Park, FL 32792
• 

  /2

  $1,165,000 Sold Jun 17, 2025

  • 3,983 Sq Ft
  • $292/SF
  • 18 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1999

  2832 Bear Island Pointe, Winter Park, FL 32792

  Welcome to 2832 Bear Island Pointe in Winter Park's premier gated community, Cypress Reserve! This meticulously maintained estate-like home is move-in-ready with 5 bedrooms plus a large office room with its own bathroom and separate exterior entry. Nestled near the serene Bear Gully Lake, this stunning residence offers the perfect blend of elegance, convenience, and resort-style living. The

  Drew Belani COMPASS FLORIDA LLC

  2832 Bear Island Pointe, Winter Park, FL 32792
• 

  

  /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
• 

  

  /84

  $445,000

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

  1900 Erudite Way, Winter Park, FL 32792

  Step into effortless style and comfort in this beautifully crafted 2024 townhome located in Winter Park's desirable Grayson Square community. From the moment you arrive, you’ll appreciate the home’s modern curb appeal and smart features, including a convenient keypad entry and smart lighting throughout.Inside, an open-concept layout welcomes you with rich wood floors, designer lighting,

  Erica Diltz BALDWIN PARK REALTY LLC

  1900 Erudite Way, Winter Park, FL 32792
• 

  

  /10

  $1,600 per month

  • 2 Beds
  • 2 Baths
  • 1,003 Sq Ft
  • Condo for Rent

  1000 S Semoran Blvd Unit 813, Winter Park, FL 32792

  This roomy 2/2 condo located in Golf side Villas, off South Semoran Boulevard, minutes away from shopping and Baldwin Park, Golf side Villas has a community pool and laundry facilities are conveniently located in the community, close to this unit. The unit features tile floors throughout, offers a nice size family room and dining area. The kitchen has granite counter tops, a large stainless steel

  Caroline Perotti BELLA VIEW REALTY LLC

  1000 S Semoran Blvd Unit 813, Winter Park, FL 32792
• 

  /2

  $735,000 Sold Jun 17, 2025

  • 1,867 Sq Ft
  • $394/SF
  • 62 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1979

  1312 Golfside Dr, Winter Park, FL 32792

  Experience luxury living in this stunning 3-bedroom, 2-bathroom pool home perfectly positioned on the 3rd hole of the golf course in Winter Park. Thoughtfully upgraded with designer details, this home blends elegance and comfort. A beautifully tiled walkway leads to an inviting interior featuring crown moldings, wood-look porcelain flooring, energy-efficient LED lighting, and stylish fixtures

  Uno Sorlie HOPKEY REALTY

  1312 Golfside Dr, Winter Park, FL 32792
• 

  

  /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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