1,114

Recently Sold Winter Park, FL Homes

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    $555,000 Sold Apr 25, 2025

    • 1,772 Sq Ft
    • $313/SF
    • 15 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1966

    633 London Rd, Winter Park, FL 32792

    Spectacular 3/2 with split plan in the Winter Park Pines. This pool planned home has been freshly painted throughout the interior and features vinyl plank flooring and cermic tile, breakfast bar in the kitchen, separate dining room, living room, family room, large foyer, plenty of closet space throughout, a screened patio and a large fenced back yard. It also has a complete stainless steel

    Barry Sanford PA CHARLES RUTENBERG REALTY ORLANDO

    633 London Rd, Winter Park, FL 32792
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    $535,000 Sold Apr 25, 2025

    • 1,795 Sq Ft
    • $298/SF
    • 5 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1947

    1531 Norfolk Ave, Winter Park, FL 32789

    Welcome to your dream home nestled in the highly sought-after College Park district of Winter Park! This charming residence seamlessly blends history with modern upgrades, offering a perfect balance of comfort and convenience.Step inside to discover a beautifully updated kitchen featuring elegant granite countertops, ideal for both casual meals and entertaining guests. The home now boasts 1,795

    Erica Diaz HOMEVEST REALTY

    1531 Norfolk Ave, Winter Park, FL 32789
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    $480,000 Sold Apr 25, 2025

    • 1,520 Sq Ft
    • $316/SF
    • 60 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1955

    525 S Lakemont Ave, Winter Park, FL 32792

    Centrally located residence that features a family-friendly layout located in one of the most sought-after areas of the Orlando region, Winter Park. This upscale community is conveniently located just 5 to 10 minutes by car from downtown Orlando. The interior boasts three generously sized bedrooms, two full bathrooms, and an additional half bath in the utility area, all enhanced by elegant wood

    Augusto Rodriguez-Aponte MARK SPAIN REAL ESTATE

    525 S Lakemont Ave, Winter Park, FL 32792
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    $1,516,500 Sold Apr 24, 2025

    • 2,420 Sq Ft
    • $627/SF
    • 31 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1978

    335 Beloit Ave, Winter Park, FL 32789

    A special opportunity awaits on one of Winter Park’s most sought-after streets, BELOIT AVENUE! This charming 3-bedroom, 2-bathroom home is perfectly positioned just two blocks from the vibrant energy of Park Avenue and steps from the lush greens of the Winter Park 9 Golf Course.Brimming with character and warmth, this jewel box offers over 2,400 square feet of beautifully designed living space.

    MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    335 Beloit Ave, Winter Park, FL 32789
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    $1,295,000 Sold Apr 22, 2025

    • 2,795 Sq Ft
    • $463/SF
    • 5 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2017

    1601 Chestnut Ave, Winter Park, FL 32789

    Nestled in one of the most sought-after locations, the “Tree Streets” of Winter Park. 1601 Chestnut Avenue is a stunning Modern European Cottage-style home, built in 2017, that masterfully blends classic charm with modern finishes. Offering over 2,800 square feet, this pool home includes: four bedrooms, three full baths, and an over-sized loft. Step inside to hard wood flooring, complemented by

    Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

    1601 Chestnut Ave, Winter Park, FL 32789
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    $140,000 Sold Apr 22, 2025

    • 1,003 Sq Ft
    • $140/SF
    • 21 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1969

    1000 S Semoran Blvd Unit 511, Winter Park, FL 32792

    This Winter Park Condo is located on the first floor and Priced Below Market Value for a quick sales. Can't find a 2/2, first floor condo in Winter Park at this price. Needs a touch of TLC, if desired, but not necessary . Conveniently located near Baldwin Park, Full Sail, Downtown Orlando, and a short drive to the Orlando International Airport. This condo is across from the community pool,

    Jeff Stewart WEICHERT REALTORS HALLMARK PROPERTIES

    1000 S Semoran Blvd Unit 511, Winter Park, FL 32792
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    $394,900 Sold Apr 22, 2025

    • 1,196 Sq Ft
    • $330/SF
    • 17 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1978

    6901 Jackman Blvd, Winter Park, FL 32792

    Welcome to this charming home located in the desirable community of Howell Branch Woods in Winter Park, Florida. With 3 bedrooms and 2 bathrooms, this 1,196 sq ft home offers a comfortable and functional layout. Upon entering, you are greeted by a bright and inviting living room featuring custom plank tile flooring that adds a modern touch. The updated kitchen is perfect for cooking and

    David Bollet REDFIN CORPORATION

    6901 Jackman Blvd, Winter Park, FL 32792
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    $800,000 Sold Apr 21, 2025

    • 2,192 Sq Ft
    • $365/SF
    • 0 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2020

    2255 Marsh Sedge Ln, Winter Park, FL 32792

    Welcome to your dream home! This beautifully designed 4-bedroom, 3-bathroom home offers an elegant blend of style, comfort, and cutting-edge technology in the sought-after gated community of Hawks Crest, featuring resort-style amenities. Inside, you'll love the spacious interior with an ideal, open-concept floorplan. The home boasts eye-catching crown molding throughout the common areas and

    Raymond Lopez KELLER WILLIAMS ADVANTAGE 2 REALTY

    2255 Marsh Sedge Ln, Winter Park, FL 32792
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    $580,000 Sold Apr 21, 2025

    • 1,710 Sq Ft
    • $339/SF
    • 1 Day On Market
    • 4 Beds
    • 2 Baths
    • Built 1953

    3006 Northwood Blvd, Winter Park, FL 32789

    Discover the perfect blend of classic charm and modern potential in this delightful single-family home with endless possibilities, nestled in a prime Winter Park location! This inviting fully fenced home features a comfortable layout with 3 bedrooms and 1 bathroom in the main living area. An exciting attached addition has a separate entrance leading to a spacious 4th bedroom and 2nd bathroom,

    Chris Creegan CREEGAN GROUP

    3006 Northwood Blvd, Winter Park, FL 32789
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    $125,000 Sold Apr 21, 2025

    • 1,062 Sq Ft
    • $118/SF
    • 26 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1974

    3045 Aaron Burr Ave Unit P-2D, Winter Park, FL 32792

    Second floor 2/2 condo with new "Trane" a/c unit. Spacious 2 bedroom w/walk-in double closets both bedrooms & 2 baths. Ceiling fans included!Screen balcony extends the lenght of the unit, access from master & living double sliding glass doors.Washer & dryer hook up. Large community Pool, tennis courts & recreation building! HOA covers **water/sewer bill**, pest control, building insurance&

    Leyder Salamanca FLORIDA REALTY INVESTMENTS

    3045 Aaron Burr Ave Unit P-2D, Winter Park, FL 32792
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    $260,000 Sold Apr 21, 2025

    • 1,230 Sq Ft
    • $211/SF
    • 102 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1988

    7783 Country Place Unit J2, Winter Park, FL 32792

    Excellent opportunity to live in this quiet Winter Park neighborhood of Goldenrod Villas. Nestled in the back of the community, this 3 bedrooms/2 bathroom single story unit has over 1200 square feet. Wonderful open floor plan with a living/dining room that leads through sliding glass doors to a screened in porch with storage closet plus a small back patio. Both bathrooms were updated in 2024

    Patty Munsey FANNIE HILLMAN & ASSOCIATES

    7783 Country Place Unit J2, Winter Park, FL 32792
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    $4,100,000 Sold Apr 18, 2025

    • 4,582 Sq Ft
    • $895/SF
    • 1 Day On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2024

    1691 Chestnut Ave, Winter Park, FL 32789

    Welcome home to this one-of-a-kind custom-designed and built home by Ferrarini Custom Homes, Inc. in February 2024. This singular mid-century modern home is like no other in Winter Park.  Boasting an ideal location just steps from Phelps Park as well as only 1.5 miles from Park Avenue makes it the ideal home for the most discerning buyer. Custom features abound in this stunning 4582 sq. ft.

    Sue Silberbusch COMPASS FLORIDA LLC

    1691 Chestnut Ave, Winter Park, FL 32789
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    $435,000 Sold Apr 18, 2025

    • 1,653 Sq Ft
    • $263/SF
    • 84 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1983

    1860 Gladiolas Dr, Winter Park, FL 32792

    This stunning 4 bedroom home seamlessly blends luxury and functionality, perfect for modern living and entertaining. The centerpiece of the property is a large, open pool, surrounded by a private fenced backyard. offering an oasis of relaxation and seclusion. Inside the kitchen showcases granite countertops and stainless-steel appliances, providing a sleek, modern aesthetic combined with

    James Begor COLDWELL BANKER REALTY

    1860 Gladiolas Dr, Winter Park, FL 32792
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    $255,000 Sold Apr 18, 2025

    • 1,332 Sq Ft
    • $191/SF
    • 122 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1984

    5466 Bracken Ct, Winter Park, FL 32792

    Great value for a three bedroom home in Winter Park! This two story town home has the primary bedroom on the first floor and two generous bedrooms on the second floor. While it does need some cosmetic work, there is a new roof, new ac and newer gutters. The first floor is all ceramic tile. The upstairs bedrooms are laminate. In the upstairs bath there is a new vanity and ceramic tile flooring.

    Tom Nestor EXP REALTY LLC

    5466 Bracken Ct, Winter Park, FL 32792
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    $730,000 Sold Apr 17, 2025

    • 2,155 Sq Ft
    • $339/SF
    • 3 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1973

    920 Fairway Dr, Winter Park, FL 32792

    Welcome to this beautifully updated 2,155 sq ft pool home, featuring 4 bedrooms and 2 bathrooms, situated in a peaceful neighborhood just minutes from schools, shopping, and the local Winter Pines Golf Course. After a long day, enjoy the convenience of walking to the golf course to unwind—whether you're hitting balls at the range or relaxing with happy hour and dinner at the Bonfire Grill. This

    Nicole Howell FANNIE HILLMAN & ASSOCIATES

    920 Fairway Dr, Winter Park, FL 32792
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    $385,000 Sold Apr 17, 2025

    • 1,411 Sq Ft
    • $273/SF
    • 11 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1985

    1197 Village Forest Place, Winter Park, FL 32792

    PLANT YOUR ROOTS HERE!! This lovely 3 BEDROOM, 2 BATH, 1411sf BLOCK HOME on .26 Acre is MOVE-IN READY at an Affordable Price!General features of this home include a NEWER ROOF (June 2023), LUXURY VINYL PLANK FLOORING (2020), SPLIT BEDROOM PLAN with CEILING FANS IN EVERY BEDROOM, 6 PANEL DOORS, 5.5" BASEBOARDS, DOUBLE PANE ENERGY EFFICIENT WINDOWS, RING DOORBELL, ELECTRONIC KEYPAD DOOR ENTRY,

    Donna Cox REAL ESTATE FIRM OF ORLANDO

    1197 Village Forest Place, Winter Park, FL 32792
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    $480,000 Sold Apr 17, 2025

    • 1,920 Sq Ft
    • $250/SF
    • 29 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1981

    423 Ololu Dr, Winter Park, FL 32789

    NO HOA! Beautifully Remodeled Home with Expansive Garden in Winter ParkWelcome to this charming and fully remodeled two-story, 3-bedroom, 3-bathroom home nestled in the heart of Winter Park. Offering a blend of modern upgrades and historic charm, this property is surrounded by a vibrant community with easy access to top destinations.Prime Location:5 minutes to Whole Foods

    tanya fei AAA GLOBAL VENTURES PA

    423 Ololu Dr, Winter Park, FL 32789
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    $465,000 Sold Apr 17, 2025

    • 1,647 Sq Ft
    • $282/SF
    • 80 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1988

    2073 Shadyhill Terrace, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Nestled on a lushly landscaped corner lot, this beautiful Winter Park, FL homes offers a serene retreat with picturesque pond views. This thoughtfully designed home features engineered hardwood flooring throughout and new French-style doors with built-in blinds in the living, family room, and primary bedroom. Vaulted ceilings and three solar tube

    Holly Kroll KROLL REALTY GROUP

    2073 Shadyhill Terrace, Winter Park, FL 32792
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    $615,000 Sold Apr 17, 2025

    • 2,242 Sq Ft
    • $274/SF
    • 82 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1987

    735 Maryland Ave, Winter Park, FL 32789

    Welcome to this elegant three-story townhouse in the heart of Winter Park! Step through French doors into a welcoming foyer leading to a bright and open living room, seamlessly connected to the dining area. Adorned with crown molding and charming Spanish tile, this space is bathed in natural light from sliding glass doors that open to a private outdoor patio. The kitchen features white cabinets,

    Chuck Massab FANNIE HILLMAN & ASSOCIATES

    735 Maryland Ave, Winter Park, FL 32789
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    $1,630,000 Sold Apr 17, 2025

    • 3,174 Sq Ft
    • $514/SF
    • 146 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2009

    101 S New York Ave Unit 302, Winter Park, FL 32789

    One or more photo(s) has been virtually staged. This one-of-a-kind duplex in the heart of Winter Park stands out as the best value in town. Discover an unparalleled living experience in over 3,100 square feet of sophisticated space. Every detail- from the exquisite wood craftmanship which exudes classic Americana to the meticulously finished gourmet kitchen, this home truly speaks of timeless

    Sandra Cuba PREMIER SOTHEBY'S INTL. REALTY

    101 S New York Ave Unit 302, Winter Park, FL 32789
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    $540,000 Sold Apr 16, 2025

    • 1,466 Sq Ft
    • $368/SF
    • 4 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1958

    2335 Coldstream Dr, Winter Park, FL 32792

    Incredible opportunity to own a beautifully updated POOL home in Winter Park... just a block from Top-rated Brookshire Elementary School! Situated on an oversized lot with 2-car garage, this home offers the perfect blend of function, design, and comfort- boasting Mid-Century Modern vibes! As you enter through the beautiful double glass doors, you are greeted by an expansive foyer that flows

    Allison Day RE/MAX TOWN & COUNTRY REALTY

    2335 Coldstream Dr, Winter Park, FL 32792
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    $775,000 Sold Apr 16, 2025

    • 2,804 Sq Ft
    • $276/SF
    • 73 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1968

    744 London Rd, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. New Price Reduction now $799,000!!! Great Community! Step into a home where luxury, style, and functionality come together seamlessly! This stunning 2,804-square-foot pool home offers five bedrooms, three bathrooms, and an array of beautifully designed spaces that cater to both relaxation and entertaining. Every corner of this property has been

    Randall Shirey CHARLES RUTENBERG REALTY ORLANDO

    744 London Rd, Winter Park, FL 32792
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    $770,000 Sold Apr 15, 2025

    • 2,265 Sq Ft
    • $340/SF
    • 1 Day On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2018

    1816 Mondrian Cir, Winter Park, FL 32789

    Welcome to The Mondrian Winter Park, where modern elegance meets serene waterfront living! This extraordinary community features 30 sleek townhomes nestled alongside the tranquil shores of enchanting Lake Killarney. Step inside and be captivated by the exquisite finishes that define this remarkable residence—a true testament to quality and sophistication. Upon entering, you’ll find a palette of

    Brian Teach COLDWELL BANKER RESIDENTIAL RE

    1816 Mondrian Cir, Winter Park, FL 32789
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    $385,000 Sold Apr 15, 2025

    • 1,397 Sq Ft
    • $276/SF
    • 46 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1994

    3377 Hamlet Loop, Winter Park, FL 32792

    This beautiful 3-bedroom, 2.5 bathroom home has been meticulously cared for by the original owner for over 30 years, with acute attention to every detail. As you enter through the brand new front door, you will marvel at at the soaring, vaulted ceilings and a stunning Palladian window providing you with the an open and airy feeling. The living room beckons you in with a cozy fireplace and

    Amy Turner KELLER WILLIAMS WINTER PARK

    3377 Hamlet Loop, Winter Park, FL 32792
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    $230,000 Sold Apr 15, 2025

    • 1,295 Sq Ft
    • $178/SF
    • 52 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1980

    2498 Timberline Dr Unit 2498, Winter Park, FL 32792

    Cedarwood Village-Affordable living in a great location in Winter Park. This 2 bedroom, 2 bath, 1295 SF condominium offers an open floor plan with vaulted ceilings and sky lights in the living and dining areas and a wood burning fireplace in the living room. The Kitchen overlooks a private courtyard with sliding glass doors. There is room for a quaint breakfast table, additional storage cabinets

    Melissa Woodman FANNIE HILLMAN & ASSOCIATES

    2498 Timberline Dr Unit 2498, Winter Park, FL 32792
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    $2,100,000 Sold Apr 15, 2025

    • 2,894 Sq Ft
    • $726/SF
    • 35 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1999

    1032 Early Ave, Winter Park, FL 32789

    Discover your own slice of paradise on this extraordinary property spanning nearly five acres, perfectly nestled between two serene lakes in Winter Park. Offering unmatched privacy and tranquility, this retreat is ideal for those who value seclusion, natural beauty, and convenience—all within city limits, yet feeling a world away. With motorized boats allowed on both lakes, you can spend

    Teresa Corbett KINCAID REALTY

    1032 Early Ave, Winter Park, FL 32789
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    $439,900 Sold Apr 14, 2025

    • 1,708 Sq Ft
    • $258/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1986

    1751 Meadowgold Ln, Winter Park, FL 32792

    Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home with a loft in the highly sought-after Autumn Glen community, located in the heart of Winter Park and within a top-rated school district.This home offers a new roof installed in 2020 and a Goodman 2-stage A/C system from 2018, ensuring both comfort and energy efficiency. Freshly updated with new stucco and paint in 2022, it

    Vi Mateo KELLER WILLIAMS WINTER PARK

    1751 Meadowgold Ln, Winter Park, FL 32792
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    $649,000 Sold Apr 14, 2025

    • 1,545 Sq Ft
    • $420/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1981

    721 Glenridge Way, Winter Park, FL 32789

    Charming pool home zoned for Audubon K-8 and Winter Park High, tucked behind a private courtyard with artificial turf that feels like your own little secret garden. Vaulted ceilings with tongue-and-groove details add warmth and character to the living and dining areas. The eat-in kitchen features a large passthrough window overlooking the great room, perfect for entertaining. The bright Florida

    Maria Van Warner FANNIE HILLMAN & ASSOCIATES

    721 Glenridge Way, Winter Park, FL 32789
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    $660,000 Sold Apr 14, 2025

    • 2,145 Sq Ft
    • $308/SF
    • 29 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1978

    1037 Fairway Dr, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Elegant 3-Bedroom, 3-Bathroom Home With New Roof and NO HOA on Winter Park Pines Golf Course!Step into this beautifully updated single-story home, perfectly situated on the scenic Winter Park Pines Golf Course. Offering a seamless blend of modern design and cozy charm, this property boasts 3 spacious bedrooms, each with its own en suite

    Skip Juma LEGACY REALTY & BROKERS LLC

    1037 Fairway Dr, Winter Park, FL 32792
  • /2

    $315,000 Sold Apr 14, 2025

    • 1,148 Sq Ft
    • $274/SF
    • 35 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1969

    690 Osceola Ave Unit 308, Winter Park, FL 32789

    Seller motivated!!! **Prime Location & Endless Potential!** Fantastic opportunity to make it your own Oasis with some updating. Transform this condo with your personal design. Situated in Winter Park's most sought-after zip code, this spacious 2-bedroom, 2-bath lakefront condo is an incredible opportunity to create your perfect retreat. Enjoy your dock—ideal for a boat or paddle board—and unwind

    Deborah Teixeira STRAWBERRY FIELDS FOREVER REALY LLC

    690 Osceola Ave Unit 308, Winter Park, FL 32789
  • /2

    $90,250 Sold Apr 14, 2025

    • 1,108 Sq Ft
    • $81/SF
    • 58 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1974

    3000 George Mason Ave Unit 1, Winter Park, FL 32792

    Back on the Market. Don’t miss the opportunity to live in fabulous Winter Park just minutes from shopping, amazing restaurants and easy access to the airport and 417 Expressway. This beautiful two-level condo is in the heart of it all. With Spanish Tile throughout the bottom floor. Kitchen with beautiful granite counter tops. Gorgeous staircase that leads you up to two bedrooms. The master

    Nathalie Charles PREMIUM PROPERTIES REAL ESTATE

    3000 George Mason Ave Unit 1, Winter Park, FL 32792
  • /2

    $140,000 Sold Apr 14, 2025

    • 582 Sq Ft
    • $241/SF
    • 152 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1960

    151 N Orlando Ave Unit 142, Winter Park, FL 32789

    Introducing a charming 1 bed, 1 bath condo located on the serene shores of Lake Killarney in Winter Park Florida. Enjoy the perfect balance of lakeside tranquility, urban convenience, with a stunning sunset and being just a short walk to Trader Joe's, movie theaters, restaurants, and coffee shops. This home is ideal for someone seeking a peaceful retreat with all the benefits of a vibrant

    TOM NOELKE EXP REALTY LLC

    151 N Orlando Ave Unit 142, Winter Park, FL 32789
  • /2

    $1,885,000 Sold Apr 11, 2025

    • 3,499 Sq Ft
    • $539/SF
    • 0 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2024

    2144 Sycamore Dr, Winter Park, FL 32789

    Stunning new Winter Park residence.

    Christopher Christensen COMPASS FLORIDA LLC

    2144 Sycamore Dr, Winter Park, FL 32789
  • /2

    $675,000 Sold Apr 11, 2025

    • 2,258 Sq Ft
    • $299/SF
    • 4 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1968

    604 Darcey Dr, Winter Park, FL 32792

    Welcome to this desirable 4 bedroom, 2 bathroom gem situated on a coveted corner lot in the heart of Brookshire Heights. With more than 2,200 SF of living space, this home offers a welcoming atmosphere with its spacious formal living and dining areas. Beautiful plantation shutters enhance the interior, providing both elegance and privacy. The kitchen features convenient eat-in space, a closet

    Tiffany Grindstaff KELLY PRICE & COMPANY LLC

    604 Darcey Dr, Winter Park, FL 32792
  • /2

    $500,000 Sold Apr 11, 2025

    • 2,204 Sq Ft
    • $227/SF
    • 23 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1985

    4309 Enright Ct, Winter Park, FL 32792

    Welcome home! This inviting two-story pool home offers the perfect blend of modern features and classic 1980s charm on a large, 0.25-acre lot. Driving up to the property, you immediately notice its quaint, cul-de-sac location and warm curb appeal enhanced by its warm brick facade. At the front door, high ceilings and a cozy fireplace greet you in the living room and lead you into the heart of the

    Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

    4309 Enright Ct, Winter Park, FL 32792
  • /2

    $175,000 Sold Apr 11, 2025

    • 730 Sq Ft
    • $240/SF
    • 230 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1964

    700 Melrose Ave Unit E6, Winter Park, FL 32789

    Welcome to this charming first-floor, one-bedroom, one-bathroom condo in the highly sought-after Winter Park Gardens community, exclusive 55+. This bright and airy home features an open floor plan with a spacious living area and a versatile sunroom, perfect for an additional living space or home office. The sunroom offers stunning views of the tranquil pond and lush garden, creating a serene

    Milton James COLDWELL BANKER RESIDENTIAL RE

    700 Melrose Ave Unit E6, Winter Park, FL 32789
  • /2

    $600,000 Sold Apr 10, 2025

    • 2,141 Sq Ft
    • $280/SF
    • 20 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1972

    7531 Lodge Pole Trail, Winter Park, FL 32792

    Welcome to this beautifully renovated 4-bedroom, 2.5-bathroom block home located on a serene, over one-third acre lot in desirable Winter Park. The private, fully fenced yard offers peace and quiet, making it the perfect retreat for families and those who love to entertain. With 2,141 square feet of living space and 3,175 total square feet under the roof, including porches and a large garage,

    Austin Cummings NEXTDWELL

    7531 Lodge Pole Trail, Winter Park, FL 32792
  • /2

    $1,100,000 Sold Apr 10, 2025

    • 2,432 Sq Ft
    • $452/SF
    • 44 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1952

    1932 Temple Dr, Winter Park, FL 32789

    Luxury is a lifestyle, and this Winter Park modern bungalow on a cobblestone street is full of natural light, clean lines and crisp open spaces. Three bedrooms and 2.5 baths in the main house, this home has been thoughtfully renovated with style and beckons the green of an outdoor lifestyle. Over 2,400 square feet in main house and the garage was converted to an additional dwelling unit, adding

    Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    1932 Temple Dr, Winter Park, FL 32789
  • /2

    $365,000 Sold Apr 10, 2025

    • 1,452 Sq Ft
    • $251/SF
    • 49 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1957

    5102 Lake Howell Rd, Winter Park, FL 32792

    Live the perfect suburban lifestyle. Minutes to historic downtown Winter Park, this 3 bedroom 2 Bath Mid Century Modern home has an ideal location. The nearly quarter acre lot backs up to the Interlachen Country Club Conservation area, so it feels very private. Yet, you are close to every convenience, shopping, restaurants, hospitals. Walking distance to YMCA. From the minute you step in, you

    Rosye Chowanski COLDWELL BANKER REALTY

    5102 Lake Howell Rd, Winter Park, FL 32792
  • /2

    $551,000 Sold Apr 10, 2025

    • 1,906 Sq Ft
    • $289/SF
    • 53 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1972

    7884 Broken Arrow Trail, Winter Park, FL 32792

    **The MOST discerning buyers must come see this home in person!** Have you been dreaming of cul-de-sac life? Take a long look at this better-than-new home. The many improvements will impress the most particular buyer and are too lengthy to fit in this description, so please reach out for a full list of updates and to schedule a tour! This is the last home sitting at the end of a beautiful

    Stacy Bucek CHARLES RUTENBERG REALTY ORLANDO

    7884 Broken Arrow Trail, Winter Park, FL 32792

Showing Results 1 - 40, Page 1 of 18

Frequently Asked Questions

What is the average home price in Winter Park, FL?
Homes for sale in Winter Park, FL have an average home price of $1,116,764.
What is the average time to sell a house in Winter Park, FL?
The houses for sale in Winter Park, FL spend an average of 70 days on the market.
What is the number of active homes for sale in Winter Park, FL?
There are 253 active homes for sale in Winter Park, FL.
How many homes have sold over the last 12 months in Winter Park, FL?
695 homes have sold in Winter Park, FL over the last 12 months.

Home Trends in Winter Park, FL

Home Trends

Median Price (12 Mo)
$606,000
Median Single Family Price
$799,900
Median Townhouse Price
$599,000
Median 2 Bedroom Price
$249,900
Median 1 Bedroom Price
$157,000
Average Price Per Sq Ft
$403
Number of Homes for Sale
253
Last 12 months Home Sales
695
Months of Supply
4.40
Median List Price
$649,000
Median Discount From 1st List Price
5%
Median Home Sale Price YoY Change
1%
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