Winter Park, FL Homes

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  /69

  $1,825,000

  • 4 Beds
  • 2.5 Baths
  • 3,263 Sq Ft

  446 Alberta Dr, Winter Park, FL 32789

  Charming Opportunity in Prime Winter Park – 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits on a double lot that is .35 acres. Only a mile stroll to the famous Park Ave shops, dining and entertaining. Home site over looks Lake Osceola and the multi million dollar homes all around!! A neighborhood lot, a few doors down, allows residents to have walking access to Lake

  Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

  446 Alberta Dr, Winter Park, FL 32789
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  /12

  $1,200 per month

  • 2 Beds
  • 1 Bath
  • 713 Sq Ft
  • Condo for Rent

  1360 Formosa Ave Unit 1360 Formosa, Winter Park, FL 32789

  Centrally located 2/1 apartment. Near Shopping, gas, churches, golf, I4 access, park and much more. Across the street is Orlando. Hardwood floors.

  1360 Formosa Ave Unit 1360 Formosa, Winter Park, FL 32789
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  /2

  $475,000 Sold Jun 06, 2025

  • 1,314 Sq Ft
  • $361/SF
  • 3 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1957

  407 S Lakemont Ave, Winter Park, FL 32792

  This adorable 3 bedroom, 1 bath mid-century modern bungalow is tucked into a highly coveted part of Winter Park. Thoughtfully updated with a newer kitchen and bathroom, plus recent upgrades including new windows, a newer A/C system, and a brand-new deck—this home is move-in ready and full of charm.Set on a spacious lot, the property offers exciting potential: expand the existing home, renovate

  Meseydi Machado TCA REALTY, LLC

  407 S Lakemont Ave, Winter Park, FL 32792
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  /34

  Est $243,879 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  1925 Woodcrest Dr Unit E, Winter Park, FL 32792

  1925 Woodcrest Dr Unit E, Winter Park, FL 32792
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  /27

  $549,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft

  2244 Brookshire Ave, Winter Park, FL 32792

  Welcome to this delightful 3-bedroom, 2-bathroom single-family home located in the highly sought-after Brookshire Heights neighborhood of Winter Park. Step inside to discover an open-concept living area, perfect for entertaining or relaxing with family. The layout flows seamlessly from the living room to the dining area and kitchen, creating a bright and airy space filled with natural light. A

  Melissa Johnson EXP REALTY LLC

  2244 Brookshire Ave, Winter Park, FL 32792
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  /49

  $14,900 per month

  • 3 Beds
  • 5 Baths
  • 3,180 Sq Ft
  • Townhouse for Rent

  649 N Park Ave, Winter Park, FL 32789

  Now offered for lease, this luxury brownstone at northern end of Park Avenue delivers an exceptional lifestyle in the heart of Winter Park. In Park Hill, a distinguished collection of residences, the home is ideally positioned between upscale boutiques, acclaimed dining, cultural landmarks and historic Winter Park Golf Course. As the only brownstones in this prestigious location, this residence

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  649 N Park Ave, Winter Park, FL 32789
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  /2

  $260,000 Sold Jun 06, 2025

  • 710 Sq Ft
  • $366/SF
  • 28 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  151 N Orlando Ave Unit 115, Winter Park, FL 32789

  Fantastic 2 bed/ 1 bath - first floor condo in cool, mid-century building on Lake Killarney. This home is next to Trader Joes, Hillstone's and across the street from Winter Park Village! Lakefront Winter Park Condo Community Ground Floor Remodeled 2 Bedroom 1 Bath Condo, Remodeled Kitchen and Bath, Includes Washer Dryer Inside Unit. Wood Look Laminate and Tile Floors. Lake Front Amenities, Boat

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  151 N Orlando Ave Unit 115, Winter Park, FL 32789
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  /31

  Est $799,552 Not Listed For Sale

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

  2312 Kestrel Perch Place, Winter Park, FL 32792

  2312 Kestrel Perch Place, Winter Park, FL 32792
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  /42

  $499,999 Open Sun 12PM - 2PM

  • 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
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  /7

  $2,100 per month

  • 2 Beds
  • 2.5 Baths
  • 1,550 Sq Ft
  • Townhouse for Rent

  2560 Galliano Cir, Winter Park, FL 32792

  Welcome to your new home! This beautifully maintained 2-bedroom, 2.5-bathroom townhome is located in a quiet, gated community, offering the perfect balance of comfort, security, and convenience.Property Highlights:2 spacious bedrooms, each with private en-suite bathrooms.2.5 bathrooms total perfect for guests and everyday convenience.Bright, open-concept living and dining area

  2560 Galliano Cir, Winter Park, FL 32792
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  /2

  $434,900 Sold Jun 06, 2025

  • 1,366 Sq Ft
  • $318/SF
  • 23 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  5441 Justine Way, Winter Park, FL 32792

  Pool Home! Whole House Solar!! No HOA!!! This 3 bedroom, 2 bathroom pool home offers a split plan bedroom arrangement and open-concept gathering areas that lead out to a spacious screen-enclosed porch that faces the pool. The absence of a pool cage allows for landscape & gardening opportunities along with cannonballs at a moment’s notice. Enjoy fun in the sun and night swims next to the stone

  Sheri Malin REDFIN CORPORATION

  5441 Justine Way, Winter Park, FL 32792
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  /18

  Est $203,016 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft

  2911 Antique Oaks Cir Unit GE, Winter Park, FL 32792

  2911 Antique Oaks Cir Unit GE, Winter Park, FL 32792
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  /24

  $390,000

  • 4 Beds
  • 3 Baths
  • 1,674 Sq Ft

  3430 Arbutus Ln, Winter Park, FL 32792

  Charming Winter Park Pool Home with Mother-In-Law Suite, PLUS SELLER IS OFFERING $7,000 TOWARDS BUYERS CLOSING COST AND PRE-PAIDS.Welcome to your own slice of paradise in the heart of Winter Park! This beautifully maintained 4-bedroom, 3-bathroom home offers the perfect blend of comfort, functionality, and Florida living. The main home features 3 spacious bedrooms and 2 full bathrooms, with a

  Monica Bouyouris URBAN NEST CLUB INC

  3430 Arbutus Ln, Winter Park, FL 32792
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  /26

  $1,500 per month

  • 2 Beds
  • 2 Baths
  • 1,085 Sq Ft
  • Condo for Rent

  174 Scottsdale Square Unit 174, Winter Park, FL 32792

  Discover this beautifully remodeled 2-bedroom, 2-bathroom condo located in Winter Park. This unit is thoughtfully updated, offering a stylish and comfortable living space with two private balconies, allowing you to relax and enjoy fresh air right at home.in the 1st balcony you’ll find a private laundry room for added convenience. This unit has well-designed floor plan that maximizes space and

  Cristian Rojas KELLER WILLIAMS LEGACY REALTY

  174 Scottsdale Square Unit 174, Winter Park, FL 32792
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  /2

  $430,000 Sold Jun 06, 2025

  • 1,998 Sq Ft
  • $215/SF
  • 51 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1967

  3420 Arnel Dr, Winter Park, FL 32792

  Prime Winter Park Location – Updated 4-Bedroom Home in Eastbrook with No HOA!Welcome to 3420 Arnel Drive, a beautifully updated 4-bedroom, 2-bath home nestled in the desirable Eastbrook neighborhood of Winter Park—with no HOA! This charming home offers modern updates, spacious living areas, and an unbeatable location just minutes from Park Avenue, top-rated Seminole County schools, and endless

  Brenden Rando NEXTHOME NEIGHBORHOOD REALTY

  3420 Arnel Dr, Winter Park, FL 32792
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  /24

  Est $353,443 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft

  3173 Crown Jewel Ct, Winter Park, FL 32792

  3173 Crown Jewel Ct, Winter Park, FL 32792
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  /36

  $89,000

  • 2 Beds
  • 2 Baths
  • 1,066 Sq Ft

  3057 Aaron Burr Ave Unit 1, Winter Park, FL 32792

  Priced to sell! This updated 1st Floor, 2 bed, 2 bath unit, with luxury tile (faux wood) floors and updated amenities, is a great starter home or investment property. Freshly painted and cleaned, ready to move in! The monthly HOA fee include amenities, water & trash pick up, Exterior and ground maintenance. As a resident of the Colonies subdivision, you'll enjoy access to a host of exclusive

  Ali Khaku, MBA DALTON WADE INC

  3057 Aaron Burr Ave Unit 1, Winter Park, FL 32792
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  /18

  $2,695 per month

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft
  • House for Rent

  1509 Springtime Loop, Winter Park, FL 32792

  This beautiful 3 bedroom, 2 bath home is located in the desirable Autumn Glen neighborhood in Winter Park. Newly Renovated bathrooms and ceramic tile floor bedrooms and freshly painted interior. Vaulted ceilings throughout the home with skylights. Nice recently renovated kitchen with Stainless appliances.Brand new roof completely replaced in 2023 with new fascia, soffits, and gutters.

  1509 Springtime Loop, Winter Park, FL 32792
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  /2

  $825,000 Sold Jun 06, 2025

  • 2,563 Sq Ft
  • $322/SF
  • 40 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2020

  705 Baffie Ave, Winter Park, FL 32789

  Discover modern living at its finest in this stunning contemporary home in the heart of Winter Park! Built in 2020, this spacious four-bedroom, 2.5-bath residence offers over 2,500 square feet of beautifully designed living space ideal for families of all sizes. The first floor features a bright, open-concept kitchen with sleek finishes, a large island and ample storage, seamlessly flowing into a

  Jon Messeroff PREMIER SOTHEBY'S INTL. REALTY

  705 Baffie Ave, Winter Park, FL 32789
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  /50

  Est $529,077 Not Listed For Sale

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

  1607 Little Wren Ln, Winter Park, FL 32792

  1607 Little Wren Ln, Winter Park, FL 32792
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  /7

  $1,300,000

  • Land
  • 0.37 Acre
  • $3,513,514 per Acre

  1756 Hollywood Ave, Winter Park, FL 32789

  An oversized parcel of land ( 2 1/2 lots ) awaits on a picturesque, tree-canopied street near the Windsong neighborhood.Build a large new Custom home, or given the substantial size of the lot, it might be feasible to pursue an approval to divide it into two separate parcels. If approved, this would provide a buyer with the potential to construct two individual homes - an outstanding prospect for

  Marcio Tannus LA ROSA REALTY HORIZONS LLC

  1756 Hollywood Ave, Winter Park, FL 32789
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  /19

  $1,695 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

  $715,000 Sold Jun 06, 2025

  • 2,197 Sq Ft
  • $325/SF
  • 71 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2022

  1312 Blue Stem Ln, Winter Park, FL 32792

  Modern Elegance with Stunning Pond & Fountain Views!Welcome to your dream home, where contemporary design meets serene natural beauty. Situated on a premium lot overlooking a picturesque pond and fountain, this stunning residence offers the perfect balance of style and comfort.Step inside to discover an open-concept living space adorned with light wood laminate flooring, designed to complement

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  1312 Blue Stem Ln, Winter Park, FL 32792
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  /32

  Est $452,905 Not Listed For Sale

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

  1999 Canny Cove, Winter Park, FL 32792

  1999 Canny Cove, Winter Park, FL 32792
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  /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
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  /23

  $1,700 per month

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • Condo for Rent

  1331 Harmon Ave Unit 1333 Harmon Ave, Winter Park, FL 32789

  Updated and adorable condo/ townhome with hardwood floors and travertine floors, 2 bedrooms, 1.5 bath with 2 patios, storage, fans, and beautiful natural light through large windows.

  1331 Harmon Ave Unit 1333 Harmon Ave, Winter Park, FL 32789
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  /2

  $790,000 Sold Jun 05, 2025

  • 2,360 Sq Ft
  • $335/SF
  • 12 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1962

  600 Brechin Dr, Winter Park, FL 32792

  Welcome to one of the most sought after neighborhoods of Kenilworth Shores in Winter Park! Nestled among tree-lined streets where the mail is still delivered right to your door, this beautifully appointed 4-bedroom, 3-bathroom home blends timeless elegance with modern comfort. From the moment you step onto the charming brick walkway, you'll fall in love with the lush, mature landscaping and

  Amy Turner KELLER WILLIAMS WINTER PARK

  600 Brechin Dr, Winter Park, FL 32792
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  /9

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,027 Sq Ft

  Unlisted Address

  Unlisted Address
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  /34

  $489,900

  • 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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  /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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  /52

  $480,000 Sold Jun 05, 2025

  • 2,256 Sq Ft
  • $213/SF
  • 28 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1954

  4887 Seminole Ave, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Location, Location, Location!!!! Winter Park Florida: Large 4 Bedroom 3 Bath Home with Double Lot. This property has many upgrades such as: Stainless Steel Appliances including Gas Range and water heater, Updated Kitchen Cabinets, Exotic Granit Counter Tops, Large Living room with wood burning Fireplace and cathedral ceilings, Upgraded Flooring no

  Timothy Oster CHARLES RUTENBERG REALTY ORLANDO

  4887 Seminole Ave, Winter Park, FL 32792
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  /26

  Est $219,219 Not Listed For Sale

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

  7337 Cedar Creek Ct Unit 75, Winter Park, FL 32792

  7337 Cedar Creek Ct Unit 75, Winter Park, FL 32792
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  /24

  $365,000

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft

  260 Killarney Bay Ct Unit 6-6, Winter Park, FL 32789

  Welcome to Killarney Bay! This beautifully updated 2-bedroom, 1-bathroom Second-floor condo offers an airy, modern feel with vaulted ceilings, luxury vinyl plank flooring, and abundant natural light throughout. The open-concept kitchen features white cabinetry, stainless steel appliances, a large island, and quartz countertops, perfect for cooking and entertaining. The spacious bathroom

  Kyle Smith CHARLES RUTENBERG REALTY ORLANDO

  260 Killarney Bay Ct Unit 6-6, Winter Park, FL 32789
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  /10

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft
  • House for Rent

  5312 Poinsetta Ave Unit 1, Winter Park, FL 32792

  Attention Full Sail and UCF Students! This is the place for which you've been looking. This is a shared living space that is fully furnished with all utilities included. Each of the three rooms has its own electronic keypad lock for your privacy and security. The large common areas provide the perfect space for dining and living. A spacious laundry and kitchen provide you with plenty of space

  5312 Poinsetta Ave Unit 1, Winter Park, FL 32792
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  /41

  $4,500,000 Sold Jun 05, 2025

  • 6,000 Sq Ft
  • $750/SF
  • 3 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 2012

  2118 Lake Dr, Winter Park, FL 32789

  "The Point House" on lake Killarney. Rarely available oasis, this spectacular lake front residence is positioned on a peninsula with .90 acres and over 440+ feet of lake frontage with unobstructed lake views to the south, west and east. Constructed in 2012, this home features 6,000 living square footage (3,977 on the 1st level / 1,950 on the 2nd level), 4,000 sq. ft. of outdoor space,

  Quentin Green COMPASS FLORIDA LLC

  2118 Lake Dr, Winter Park, FL 32789
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  /11

  Est $451,315 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2877 Clever Ln, Winter Park, FL 32792

  2877 Clever Ln, Winter Park, FL 32792
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  /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
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  /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
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  /2

  $675,000 Sold Jun 04, 2025

  • 1,966 Sq Ft
  • $343/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1975

  2602 Winter Park Rd, Winter Park, FL 32789

  Nestled in Winter Park one of Central Florida’s most picturesque and established neighborhoods, this beautifully updated 3-bedroom, 2-bathroom residence with a 2-car garage is where timeless charm meets modern, effortless living. Zoned for top-rated Audubon Park K–8 and Winter Park High School, this residence offers both high-end living and lasting value in a truly special location. Inside,

  Brandon Thompson KELLER WILLIAMS ADVANTAGE III

  2602 Winter Park Rd, Winter Park, FL 32789
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  /9

  Est $398,039 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

  1768 Miller Ave, Winter Park, FL 32789

  1768 Miller Ave, Winter Park, FL 32789

Showing Results 521 - 560, Page 14 of 18