Winter Park, FL Homes

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  /44

  $1,050,000

  • 4 Beds
  • 3.5 Baths
  • 2,826 Sq Ft

  512 Clarendon Ave, Winter Park, FL 32789

  Beautifully updated 4BD/3.5BA townhome in highly sought-after Virginia Heights, just steps from Park Ave, Rollins College and zoned for Audubon K-8! This spacious 2,826 SF home features two primary suites—one on each level—ideal for guests or multi-gen living. Gorgeous hardwood like tile floors throughout, high ceilings, crown molding, and two fireplaces add timeless elegance. The chef’s kitchen

  Sarah Tomlinson COMPASS FLORIDA LLC

  512 Clarendon Ave, Winter Park, FL 32789
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  /29

  $2,750 per month

  • 3 Beds
  • 2.5 Baths
  • 1,152 Sq Ft
  • House for Rent

  957 Dupont Ave, Winter Park, FL 32789

  This beautifully maintained 3-bedroom, 2.5-bath home is a rare find. Located at 957 Dupont Ave, Winter Park, FL 32789, this charming residence offers 1,289 sq. ft. of living space on a generous 7,875 sq. ft. lot, complete with a 1-car attached garage. This home is move-in ready and brimming with updates. Step inside to discover an updated kitchen and bathrooms, remodeled within the past five

  Stephanie Barber HOME & HIVE REALTY

  957 Dupont Ave, Winter Park, FL 32789
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  /2

  $330,000 Sold Jul 23, 2025

  • 1,074 Sq Ft
  • $307/SF
  • 303 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1964

  700 Melrose Ave J 1 Ave Unit J1, Winter Park, FL 32789

  PRICE IMPROVEMENT – Best buy in Winter Park..........Motivated Sellers! CLICK ON VIRTUAL TOUR to get an overview of the complex.Step into this beautifully updated 2-bedroom, 2-bath condo located in the highly desirable Winter Park Gardens community. This move-in-ready unit has been thoughtfully upgraded with modern features, including brand-new plumbing, a tankless water heater,

  Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave J 1 Ave Unit J1, Winter Park, FL 32789
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  /25

  Est $162,859 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 759 Sq Ft

  678 Trinidad Ct Unit S, Winter Park, FL 32792

  678 Trinidad Ct Unit S, Winter Park, FL 32792
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  /42

  $599,999

  • 4 Beds
  • 2 Baths
  • 1,891 Sq Ft

  346 Elkhorn Ct, Winter Park, FL 32792

  Welcome to your next chapter in Winter Park Pines, tucked within the most sought-after school district in all of Orlando, Florida, just minutes from everything. This 4-bedroom, 2-bath, 1,891 sq ft home with an expansive 500 sq ft lanai, oversized pool, has only had two owners — and now it’s ready to welcome the third. Transformed over time, this is not a flip.From the moment you step

  Ryan Everroad 407 PROPERTIES

  346 Elkhorn Ct, Winter Park, FL 32792
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  /25

  $1,595 per month

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Condo for Rent

  7449 Wynnewood Square Unit 182, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Come home to this charming townhome in Winter Park! This beautifully maintained 2 bedroom, 2.5 bath home offers the perfect blend of comfort, convenience, and privacy. Step inside to an inviting open floor plan ideal for entertaining or simply relaxing at home. The spacious kitchen features a cozy eating area, perfect for casual meals or morning

  Annette Ortega KELLER WILLIAMS ADVANTAGE 2 REALTY

  7449 Wynnewood Square Unit 182, Winter Park, FL 32792
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  /2

  $439,900 Sold Jul 22, 2025

  • 1,576 Sq Ft
  • $279/SF
  • 6 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1958

  1945 Bering Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. ***BUY THIS HOME WITH AN FHA INTEREST RATE OF 5.375% WHEN USING THE SELLER'S PREFERRED LENDER*** You will fall in love with this mid-century Winter Park home across from Lake Bell in charming Lake Bell Terrace. This home offers 3 Bedrooms, 1 spa-like bathroom, and an en-suite half bath, a family room, living room, dining room, and a laundry room.

  Carmen Gonzalez, Pa HORIZON WEST REALTY

  1945 Bering Ave, Winter Park, FL 32789
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  /28

  Est $749,114 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,577 Sq Ft

  1300 Blue Stem Ln, Winter Park, FL 32792

  1300 Blue Stem Ln, Winter Park, FL 32792
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  /25

  $420,100

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft

  3425 Ferndell Dr, Winter Park, FL 32792

  Fully Renovated Gem in Winter Park!Welcome to your dream home in one of Central Florida’s most sought-after neighborhoods—Winter Park. This beautifully renovated 3-bedroom, 2-bathroom residence blends timeless charm with modern updates, offering the perfect move-in-ready sanctuary for today’s lifestyle.Step inside and fall in love with the light-filled open layout, anchored by a stunning

  Ivanhoe Alvarez LOKATION

  3425 Ferndell Dr, Winter Park, FL 32792
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  /20

  $4,800 per month

  • 3 Beds
  • 2.5 Baths
  • 2,196 Sq Ft
  • House for Rent

  2227 Howard Dr, Winter Park, FL 32789

  This beautifully renovated Winter Park mid-century home sits on an oversized waterfront lot minutes from downtown Winter Park, Audubon Park, and Baldwin Park. Enjoy access to top public and private schools. Step into nearly 2,200 square feet of beautifully maintained living space. Your home features a thoughtful split-bedroom floor-plan with formal living and dining rooms, a spacious family room

  Julian Correa REALTY ONE GROUP MAGIC CITY

  2227 Howard Dr, Winter Park, FL 32789
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  /2

  $450,000 Sold Jul 22, 2025

  • 2,308 Sq Ft
  • $195/SF
  • 23 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2019

  1624 Little Wren Ln, Winter Park, FL 32792

  Welcome to Hawks Crest – where modern living meets convenience and comfort. Built in 2019, this beautifully upgraded 3-bedroom, 2.5-bath townhome offers the perfect blend of style, function, and low-maintenance living—ready for you to move right in. From the moment you arrive, you’ll be charmed by the paver driveway and walkway framed by lush landscaping, leading to a bold, eye-catching front

  Steven Kwong CHARLES RUTENBERG REALTY ORLANDO

  1624 Little Wren Ln, Winter Park, FL 32792
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  /26

  Est $436,059 Not Listed For Sale

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

  2009 Canny Cove, Winter Park, FL 32792

  2009 Canny Cove, Winter Park, FL 32792
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  /29

  $369,000 Open Sat 1PM - 4PM

  • 2 Beds
  • 1 Bath
  • 1,028 Sq Ft

  1516 Pinewood Dr, Winter Park, FL 32789

  PINEWOOD SUB N/9 LOT 12 BLK AWell-maintained, modest 2-1 home in College Park with carport, deck, and porch. Home materials include laminate and tile flooring, granite kitchen countertops, energy efficient windows, vinyl siding, and metal roof. All appliances included (washer, dryer, refrigerator, dishwasher, oven/stove with range hood, microwave). Also includes backyard garden, working

  Matt Buttner LIST NOW REALTY, LLC

  1516 Pinewood Dr, Winter Park, FL 32789
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  /32

  $2,700 per month

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • House for Rent

  648 W Swoope Ave, Winter Park, FL 32789

  FOR RENT - 648 W. SWOOPE AVENUE, WINTER PARK | OFFERED AT $2,700/MO - Stunning Home, Completely Remodeled, and Professionally Designed! Super cute 3 bedroom, 1 bath home in downtown Winter Park. Updated flooring, paint, windows, newer HVAC unit, updated kitchen cabinets, stainless steel appliances, Quartz countertops, beautiful bathroom tile work & fixtures, and interior washer/dryer. Open

  Kelly Price KELLY PRICE & COMPANY LLC

  648 W Swoope Ave, Winter Park, FL 32789
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  /2

  $995,000 Sold Jul 22, 2025

  • 2,188 Sq Ft
  • $455/SF
  • 25 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2017

  1821 Windsor Dr, Winter Park, FL 32789

  WELCOME to 1821 WINDSOR DR in WINTER PARK, FLORIDA! This is a ONCE IN A LIFETIME OPPORTUNITY to own this BEAUTIFUL CUSTOM-BUILT MASTERPIECE of a HOME in ONE OF THE MOST DESIRED LOCATIONS in TOWN! When you buy this Home, you aren’t just purchasing a NEWLY BUILT CUSTOM HOME FULL OF LUXURIOUS UPGRADES and ARCHITECTURAL FEATURES; you are also buying into the LIFESTYLE that others DREAM OF LIVING in

  Chris Creegan CREEGAN GROUP

  1821 Windsor Dr, Winter Park, FL 32789
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  /31

  Est $439,802 Not Listed For Sale

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

  2021 Canny Cove, Winter Park, FL 32792

  2021 Canny Cove, Winter Park, FL 32792
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  /39

  $331,985

  • 2 Beds
  • 2 Baths
  • 1,362 Sq Ft

  638 Warrenton Rd, Winter Park, FL 32792

  BACK ON THE MARKET AFTER EXTENSIVE RENOVATIONS!!! BRAND NEW KITCHEN, BATHS, BRAND NEW GORGEOUS LUXURY VINYL PLANK FLOORING THROUGHOUT! BRAND NEW ROOF AS WELL! Welcome to this beautiful 2-Bedroom, 2-Bathroom patio home located in desirable Winter Park. This duplex offers a range of amenities that will surely enhance your living experience. This beauty has BRAND NEW Luxury Vinyl

  Nicholas Musashe SUN PROPERTIES, INC.

  638 Warrenton Rd, Winter Park, FL 32792
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  /26

  $2,940 per month

  • 3 Beds
  • 2 Baths
  • 1,651 Sq Ft
  • House for Rent

  333 Cambridge Blvd, Winter Park, FL 32789

  Welcome to your dream home in Winter Park, Florida! Nestled in the heart of sunshine and sophistication, this charming 3-bedroom, 2-bathroom residence offers the perfect blend of comfort and style. Step inside to discover an inviting living space flooded with natural light, perfect for relaxing with loved ones or entertaining guests. The spacious kitchen boasts modern appliances and ample

  David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

  333 Cambridge Blvd, Winter Park, FL 32789
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  /2

  $2,495,000 Sold Jul 22, 2025

  • 3,551 Sq Ft
  • $703/SF
  • 47 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1995

  940 Lincoln Cir, Winter Park, FL 32789

  Now offered at $2,495,000—an outstanding value for a thoughtfully designed pool home on a spacious lot in Winter Park’s most sought after neighborhoods. Located in the heart of the “Golden Triangle”—the core residential district just a short walk from Park Avenue’s world-class shopping and dining—940 Lincoln Circle is a beautifully renovated West Indies/Key West-style home that blends

  Padgett McCormick KELLY PRICE & COMPANY LLC

  940 Lincoln Cir, Winter Park, FL 32789
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  /32

  Est $446,100 Not Listed For Sale

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

  2025 Canny Cove, Winter Park, FL 32792

  2025 Canny Cove, Winter Park, FL 32792
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  /74

  $1,695,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 4 Baths
  • 2,964 Sq Ft

  1270 Arlington Place, Winter Park, FL 32789

  Modern Elegance in the Heart of Winter Park!Located just a half-mile from the renowned shops and dining of Park Avenue, this architecturally striking residence blends luxury, modern design, and thoughtful functionality. Designed by Michael Wenrich and built by Jim Winters, every inch of this home reflects exceptional craftsmanship and elevated taste.A long paver driveway welcomes

  Brian Mitnik RE/MAX 200 REALTY

  1270 Arlington Place, Winter Park, FL 32789
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  /12

  $1,550 per month

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

  1000 S Semoran Blvd Unit 115, Winter Park, FL 32792

  Welcome to Golfside Villas. This community is nestled near Downtown Orlando, Full Sail, UCF, Lynx bus stop, major shopping centers, restaurants, I-4, 408, & Orlando International Airport. This condominium features an open floor plan that consist of 2 bedrooms, 2 bathrooms, and a screened in patio. Over 1000 sqft of living space awaits you with a few upgrades. This neighborhood features a laundry

  Damon Mayers MAYERS REAL ESTATE LLC

  1000 S Semoran Blvd Unit 115, Winter Park, FL 32792
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  /2

  $198,000 Sold Jul 21, 2025

  • 1,031 Sq Ft
  • $192/SF
  • 11 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1983

  3247 Forest Oaks Ct Unit 116, Winter Park, FL 32792

  Welcome to this beautifully updated 2-bedroom, 2.5-bath condo in the heart of Winter Park! Featuring ceramic tile and laminate wood flooring throughout, this home offers a modern feel with upgraded kitchen finishes, refreshed lighting, ceiling fans, and recently updated sinks, toilets, and flooring. The spacious layout provides comfort and convenience, with both bedrooms offering en-suite

  Brandon Feng KELLER WILLIAMS WINTER PARK

  3247 Forest Oaks Ct Unit 116, Winter Park, FL 32792
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  /64

  Est $1,126,032 Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 5,021 Sq Ft

  3708 Vinsetta Ct, Winter Park, FL 32792

  3708 Vinsetta Ct, Winter Park, FL 32792
• 

  

  /41

  $169,900

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit D116, Winter Park, FL 32789

  MOTIVATED SELLER - CAN CONTRIBUTE TOWARDS CLOSING COSTS!Location, location, location!! And priced to sell!! This 3 bedroom 2 bathroom corner unit condo is conveniently located within a short drive distance to Rollins College, UCF, Valencia College, hospitals, shopping, dining, and entertainment! The unit is located on the first floor and has an open floor plan, spacious kitchen with plenty

  Madalay Fleming LA ROSA REALTY KISSIMMEE

  1695 Lee Rd Unit D116, Winter Park, FL 32789
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  /26

  $2,875 per month

  • 3 Beds
  • 2 Baths
  • 1,130 Sq Ft
  • Condo for Rent

  644 N Knowles Ave Unit 8, Winter Park, FL 32789

  Welcome to your private retreat in the heart of Downtown Winter Park. This exclusive address affords views of the world famous Winter Park 9 course, and the timeless Casa Feliz, right from your balcony! This wonderful 3/2 LARGE condo features: a FULLY renovated kitchen, equipped with designer touches, and top of the line stainless steel appliances, solid surface flooring throughout, clean and

  Raul Veitia BELMONT REALTY

  644 N Knowles Ave Unit 8, Winter Park, FL 32789
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  /2

  $806,000 Sold Jul 21, 2025

  • 2,223 Sq Ft
  • $363/SF
  • 4 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1979

  1261 Burning Tree Ln, Winter Park, FL 32792

  Impeccably Redesigned Pool Home in Coveted Winter Park NeighborhoodWelcome to 1261 Burning Tree Lane, a beautifully updated 4-bedroom, 2-bathroom pool home located in the highly sought-after Greenview at Winter Pines subdivision. Tucked beneath a canopy of mature oak trees and surrounded by manicured landscaping, this architect-owned residence combines timeless design with thoughtful

  Adrienne Kane REAL BROKER, LLC

  1261 Burning Tree Ln, Winter Park, FL 32792
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  /46

  Est $2,044,364 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,286 Sq Ft

  660 W Morse Blvd, Winter Park, FL 32789

  660 W Morse Blvd, Winter Park, FL 32789
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  /68

  $650,000

  • 4 Beds
  • 3 Baths
  • 2,846 Sq Ft

  3115 Heartleaf Place, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to your dream home in Winter Park, FL! Motivated seller that is offering $20,000 in closing cost assistance! This stunning 4-bedroom, 3-bathroom residence is situated on a desirable corner lot, offering ample space and privacy. This home was recently updated with a brand new HVAC system installed (May 2025), and a roof that’s only 4 years

  Selby Turnbull EXP REALTY LLC

  3115 Heartleaf Place, Winter Park, FL 32792
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  /2

  $1,500 per month

  • House for Rent

  987 Cherokee Ave, Winter Park, FL 32789

  The landlord seeks a long term tenant or a joint venture from a developer or someone with a home to move.Contact us now and let's discuss this opportunity. Vacant LandIncredible opportunity to bring your own home to this prime Winter Park building lot with all utilities stubbed at the curb from a previous home that was removed. The current owner of 987 Cherokee Avenue, Winter Park is willing to

  John R. Gordon EXP REALTY LLC

  987 Cherokee Ave, Winter Park, FL 32789
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  /2

  $86,000 Sold Jul 21, 2025

  • 1,085 Sq Ft
  • $79/SF
  • 19 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1974

  208 Scottsdale Square, Winter Park, FL 32792

  Welcome to this beautifully updated 2-story condo located in the heart of Winter Park, just minutes from UCF, Full Sail University, major highways, shopping, and dining. Nestled on the second level, this inviting home offers a functional layout with 2 spacious bedrooms and a full bathroom upstairs, plus a convenient half bathroom on the main floor.Step inside to find stylish luxury vinyl

  Jackie Criswell RE/MAX TOWN & COUNTRY REALTY

  208 Scottsdale Square, Winter Park, FL 32792
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  /29

  Est $475,208 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,468 Sq Ft

  1114 Washington Ave Unit 3, Winter Park, FL 32789

  1114 Washington Ave Unit 3, Winter Park, FL 32789
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  /30

  $759,000 Open Sun 1PM - 4PM

  • 4 Beds
  • 2 Baths
  • 2,076 Sq Ft

  620 Darcey Dr, Winter Park, FL 32792

  New Roof installed July 2025. Charming brick Winter Park home in the desirable Brookshire Heights neighborhood. This home features four bedrooms, two baths, over 2,076 square feet of natural sunlight flowing throughout, enclosed back porch and a fully fenced backyard. Beautiful curb appeal with a long extended driveway, great for large gatherings, parking your boat, RV and more. Other updates

  Michael Domi PREMIER SOTHEBY'S INTL. REALTY

  620 Darcey Dr, Winter Park, FL 32792
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  /49

  $12,480 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

  $705,000 Sold Jul 21, 2025

  • 1,408 Sq Ft
  • $501/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1967

  1730 Oneco Ave, Winter Park, FL 32789

  Vintage house with close proximity to Park Avenue surronded by newely constructed homes on a scenic brick street. A creative designer would find this vintage house a great project with a newly constructed roof to save the time. This winter park corner lot is highly sought after for its location and its potential.

  John Tremblay THE TEAM REAL ESTATE GROUP INC

  1730 Oneco Ave, Winter Park, FL 32789
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  /25

  Est $276,611 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,565 Sq Ft

  7481 Swallow Run Unit GE, Winter Park, FL 32792

  7481 Swallow Run Unit GE, Winter Park, FL 32792
• 

  

  /40

  $399,000

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft

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

  Major Price Improvement & Motivated Seller! 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

  Jeff Dodds CHARLES RUTENBERG REALTY ORLANDO

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

  

  /19

  $1,550 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

  $472,000 Sold Jul 21, 2025

  • 1,736 Sq Ft
  • $272/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  2832 Buccaneer Dr, Winter Park, FL 32792

  Nestled in one of Winter Park’s peaceful neighborhoods with *NO HOA*, this meticulously upgraded 3 bedrooms, 2 bath pool home plus 2 versatile bonus rooms, perfectly blends modern comfort, sustainable living, and timeless charm. With two vacant city-owned lots directly to the west, the property enjoys uninterrupted golden sunset views that fill the home with natural light. The exterior showcases

  Virginia Silberstein ORLANDO EXPERT REALTY LLC

  2832 Buccaneer Dr, Winter Park, FL 32792
• 

  

  /24

  Est $125,319 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,035 Sq Ft

  3054 George Mason Ave Unit 8, Winter Park, FL 32792

  3054 George Mason Ave Unit 8, Winter Park, FL 32792

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