Recently Sold Winter Park, FL Homes

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  $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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  $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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  /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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  /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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  /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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  /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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  $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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  $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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  /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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  /2

  $390,000 Sold Jun 04, 2025

  • 1,727 Sq Ft
  • $226/SF
  • 10 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1973

  264 Balfour Dr, Winter Park, FL 32792

  Welcome to 264 Balfour Drive — an exclusive residence within a private enclave of just 13 elegant townhomes in the heart of Winter Park designed by architect Nils Schweizer. a student of Frank Lloyd Wright. Offering an attached two-car garage and a premier location, this home blends sophistication with comfort in every detail.Step into a grand living room where soaring ceilings and expansive

  Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  264 Balfour Dr, Winter Park, FL 32792
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  /2

  $460,000 Sold Jun 04, 2025

  • 2,076 Sq Ft
  • $222/SF
  • 30 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2019

  1628 Little Wren Ln, Winter Park, FL 32792

  Improved Price! Welcome to your private "nest" on Little Wren. Nestled among the trees, this modern masterpiece is located directly next to a wide open green space and also backs to a private wooded area giving you beautiful, natural, unobstructed views. The home's modern architecture style is evident from the moment you approach with its striking front door acting as a key focal point.

  Kristin Haughwout-Osorio PARKSIDE PROPERTIES, LLC

  1628 Little Wren Ln, Winter Park, FL 32792
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  /2

  $835,000 Sold Jun 03, 2025

  • 2,133 Sq Ft
  • $391/SF
  • 63 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1958

  625 Worthington Dr, Winter Park, FL 32789

  Completely remodeled, coastal-inspired home is located in the highly sought-after Winter Park neighborhood of Kenilworth Shores in Winter Park 32789. Minutes from the world-renowned Park Avenue and upscale shopping, dining, parks, community events, Sunrail and more lifestyle. The home is zoned for some of Winter Park's most desirable schools, including Brookshire Elementary, Glenridge Middle, and

  Jennifer Sloan KELLY PRICE & COMPANY LLC

  625 Worthington Dr, Winter Park, FL 32789
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  /2

  $402,500 Sold Jun 02, 2025

  • 1,379 Sq Ft
  • $292/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  1301 Paradise Ln, Winter Park, FL 32792

  This fully reimagined corner-lot residence is more than a renovation; it’s a masterpiece, designed for modern living. Sited on nearly 0.40 acres, the home greets you with bold curb appeal, and sleek paver driveway that signal something truly special inside.

  Ahmad Hassan COMPASS FLORIDA LLC

  1301 Paradise Ln, Winter Park, FL 32792
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  /2

  $392,500 Sold Jun 02, 2025

  • 1,427 Sq Ft
  • $275/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1982

  2100 Shirewood Ct, Winter Park, FL 32792

  This 3-bedroom, 2-bathroom residence is situated on a corner lot, offering an inviting and comfortable living space. A notable feature of this property is the BRAND NEW ROOF and WATER HEATER, ensuring peace of mind for years to come. The split floor plan enhances both privacy and functionality. The master bedroom boasts a walk-in closet and a private ensuite bathroom. On the opposite side of the

  karen akos WEICHERT REALTORS HALLMARK PRO

  2100 Shirewood Ct, Winter Park, FL 32792
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  /2

  $615,000 Sold Jun 02, 2025

  • 2,197 Sq Ft
  • $280/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1964

  2712 Cady Way Unit 4, Winter Park, FL 32792

  Welcome to your tropical paradise in the highly sought-after Winter Park Pines neighborhood, where the mailman still delivers to your front door! This beautiful home radiates true Florida vibes with whimsical details and thoughtful touches throughout. As you step inside, you'll be greeted by an open living and dining area featuring two sets of French doors that lead to a lush, private backyard

  Amy Turner KELLER WILLIAMS WINTER PARK

  2712 Cady Way Unit 4, Winter Park, FL 32792
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  /2

  $370,000 Sold Jun 01, 2025

  • 1,409 Sq Ft
  • $263/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1958

  2805 Bongart Rd, Winter Park, FL 32792

  Welcome to this charming 3-bedroom, 2-bathroom single-story home, perfectly located in highly sought-after Winter Park. Situated on a beautiful corner lot, this property offers the ultimate in convenience and charm, with the added bonus of NO HOA! Ideal for first-time homebuyers or investors, this home boasts low-maintenance tile and laminate flooring throughout. The spacious living room is the

  Jamie Stolinas Crame CENTURY 21 CARIOTI

  2805 Bongart Rd, Winter Park, FL 32792
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  /2

  $1,002,000 Sold May 31, 2025

  • 2,295 Sq Ft
  • $437/SF
  • 4 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1989

  1265 Park Pointe Ln, Winter Park, FL 32789

  Welcome home to this beautifully upgraded gem nestled in the heart of Winter Park. This move-in-ready home sits on a quiet street, offering easy access to major highways, top-rated schools, upscale dining, shopping, and Central Florida’s best attractions.No detail has been overlooked in this full renovation. The custom kitchen is a chef’s dream—featuring quartz countertops, an oversized island

  Frances Speights KELLER WILLIAMS ADVANTAGE III

  1265 Park Pointe Ln, Winter Park, FL 32789
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  /2

  $520,000 Sold May 30, 2025

  • 943 Sq Ft
  • $551/SF
  • 41 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1956

  2507 Lafayette Ave, Winter Park, FL 32789

  ***Premier Land Opportunity on Lafayette Avenue, Winter Park, FL**Take advantage of an exceptional opportunity to own a prime piece of land in the highly desirable area of Winter Park, FL. This 7,734 sq. ft. lot on Lafayette Avenue offers an unparalleled chance to build the custom home of your dreams in one of Central Florida's most sought-after neighborhoods.With generous dimensions and

  William Grim, III RE/MAX ASSURED

  2507 Lafayette Ave, Winter Park, FL 32789
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  $1,550,000 Sold May 30, 2025

  • Land
  • 0.30 Acre
  • $5,166,667 per Acre

  • 42 Days On Market

  1181 Via Capri, Winter Park, FL 32789

  This is your chance to create the home of your dreams in one of Winter Park’s most sought-after neighborhoods. Situated on an oversized 80 x 180 lot (0.30 acres), this property offers ample space and endless potential. The existing structure has already been removed, making way for a seamless building process.Enjoy a walkable lifestyle with the Winter Park Racquet Club just steps away and the

  Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  1181 Via Capri, Winter Park, FL 32789
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  /2

  $569,000 Sold May 30, 2025

  • 1,642 Sq Ft
  • $347/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1952

  1368 Devon Rd, Winter Park, FL 32789

  Welcome home to timeless beauty in the heart of highly sought-after ORWIN MANOR! Imagine living the Winter Park lifestyle where you can stroll to Foxtail Coffee, Publix, Einstein Bagels and other establishments. Jump in the car and you're just minutes from well-known Park Avenue which offers the perfect blend of charm and sophistication—with its tree-lined streets, boutique shopping, art

  Karen Ripperger LPT REALTY, LLC

  1368 Devon Rd, Winter Park, FL 32789
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  $243,800 Sold May 30, 2025

  • 960 Sq Ft
  • $254/SF
  • 24 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1984

  255 Sandlewood Trail, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Dreams Do Come True! FHA, VA, and DPA approved, making it a smart choice for a wide range of buyers. Welcome to your next home in the heart of 32789—Winter Park’s hidden gem, Sandlewood Creek! This rare townhome-style condo offers unbeatable value in a prime location with NO neighbors above or below and a LOW HOA.Step inside and enjoy nearly 1,000

  Freddie Crespo INVESTOR'S REAL ESTATE LLC

  255 Sandlewood Trail, Winter Park, FL 32789
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  /2

  $410,000 Sold May 30, 2025

  • 1,570 Sq Ft
  • $261/SF
  • 13 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1957

  1840 Maywood Rd, Winter Park, FL 32792

  Welcome to this beautifully updated four-bedroom, two-bath mid-century block home under the canopy of a majestic oak tree in the heart of Winter Park. From the moment you arrive, you’ll appreciate the inviting curb appeal, enhanced by fresh exterior paint, modern geometric accents and a wide driveway with covered parking. Step inside to find a sun-soaked living room with vaulted ceilings and

  Nancy Merriam PREMIER SOTHEBY'S INTL. REALTY

  1840 Maywood Rd, Winter Park, FL 32792
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  /2

  $650,000 Sold May 30, 2025

  • 2,002 Sq Ft
  • $325/SF
  • 79 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2019

  1219 Verdant Glade Place, Winter Park, FL 32792

  Welcome to this stunning two-story, 3-bedroom, 3 and a half bathroom home, nestled within the highly desirable Winter Park in a secure gated community. This kitchen boasts luxury features including quartz countertops, stainless steel appliances and rich dark wood cabinets. The master bedroom, with a spacious bathroom and walk-in closet, is conveniently located downstairs for added convenience.

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  1219 Verdant Glade Place, Winter Park, FL 32792
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  /2

  $230,000 Sold May 30, 2025

  • 1,026 Sq Ft
  • $224/SF
  • 75 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  1500 Gay Rd Unit 10C, Winter Park, FL 32789

  Waterfront Community on beautiful Lake Killarney. Enjoy breathtaking sunsets on Community deck! Private Boat Ramp on this Skiable Lake, limited Boat parking on property. 2 Bedroom 2 Bath second floor Unit has been meticulously maintained by Winter Resident. Furniture purchased in 2020. Many Updates to Unit include new windows and window treatments, 2024 new Hot Water Heater, Baths redone in

  Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 10C, Winter Park, FL 32789
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  /2

  $400,000 Sold May 29, 2025

  • 1,467 Sq Ft
  • $273/SF
  • 36 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  5144 Goldenrod Place Rd, Winter Park, FL 32792

  Great Opportunity. Nestled on an oversized lot at the end of a peaceful cul-de-sac, this charming home offers the perfect blend of privacy and comfort. The spacious feel of the location provides a serene and tranquil setting, making it the ideal place to relax and unwind on your huge Patio overlooking wonderful backyard ! As you step inside, the warm and cozy atmosphere welcomes you. The home's

  Rebecca Sparks C. APOLLO REALTY INC

  5144 Goldenrod Place Rd, Winter Park, FL 32792
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  $450,000 Sold May 29, 2025

  • 1,672 Sq Ft
  • $269/SF
  • 26 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1956

  1807 Yorkshire Dr, Winter Park, FL 32792

  Ready to demo and BUILD NEW or completely reimagine your dream home in beautiful Winter Park??!! Look no further - this is a large .23 acre lot. Minutes to top Winter Park schools, the WP YMCA, Winter Park Racquet Club, Interlachen Country Club, shopping, dining and other conveniences and surrounded by beautiful mid-century and luxury homes. This home has 3 bedrooms plus 2 bonus rooms that would

  Carla Stanton MAINFRAME REAL ESTATE

  1807 Yorkshire Dr, Winter Park, FL 32792
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  $421,700 Sold May 29, 2025

  • 1,525 Sq Ft
  • $277/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  1189 Lazy Hollow Place, Winter Park, FL 32792

  Welcome to this meticulously updated and **FULLY FENCED POOL HOME**, reflecting exceptional pride in ownership and featuring numerous thoughtful upgrades, all nestled in the desirable Winter Park area with **NO HOA** and a **NEW METAL ROOF (2022) ** This home is ideally situated on a **QUIET CUL-DE-SAC**, offering additional privacy and tranquility. The **SOLID BLOCK CONSTRUCTION** ensures

  Virginia Silberstein ORLANDO EXPERT REALTY LLC

  1189 Lazy Hollow Place, Winter Park, FL 32792
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  /45

  $1,100,000 Sold May 29, 2025

  • 2,786 Sq Ft
  • $395/SF
  • 130 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1960

  708 Balmoral Rd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Welcome to 708 Balmoral Road, located in the desirable heart of Winter Park. This charming single-story home boasts 4 bedrooms, 3 baths, and a generous 2786 sq. ft. of living space on a sprawling, elevated 15,161 sq. ft. corner lot. The spacious and open floor plan features soaring beams in many rooms, adding to the home's character and warmth.The

  Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  708 Balmoral Rd, Winter Park, FL 32789
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  /2

  $4,599,000 Sold May 28, 2025

  • 3,660 Sq Ft
  • $1257/SF
  • 0 Days On Market

  • 5 Beds
  • 7 Baths
  • Built 1951

  985 Lincoln Cir, Winter Park, FL 32789

  Welcome to Lincoln! This new construction single family home has been meticulously crafted and constructed by Wooten Built, a locally established, award-winning developer and luxury home Builder. Location! Location! Location! Lincoln Circle is a quiet street next to Park Avenue restaurants and shopping. Easily walk to Winter Park shops, restaurants, and the Winter Park Golf Course. This bespoke

  Clay Wooten UNITED REAL ESTATE PREFERRED

  985 Lincoln Cir, Winter Park, FL 32789
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  /2

  $498,000 Sold May 28, 2025

  • 1,740 Sq Ft
  • $286/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  808 Denton Rd, Winter Park, FL 32792

  Step into a slice of mid-century magic, your private oasis awaits. On an oversized corner lot with no rear neighbors, this one-of-a-kind mid-century gem is more than just a home, it’s an experience. With classic architectural charm, lush landscaping and thoughtful updates, you’ll feel like you’ve stepped back in time without sacrificing modern-day comforts. Enjoy the tranquility of nature with

  Julie Vega-Dominguez PREMIER SOTHEBY'S INTL. REALTY

  808 Denton Rd, Winter Park, FL 32792
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  /2

  $477,500 Sold May 28, 2025

  • 2,035 Sq Ft
  • $235/SF
  • 19 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1986

  1532 Lawndale Cir, Winter Park, FL 32792

  Welcome to Your Florida Oasis in Winter Park!This beautifully maintained 4-bedroom, 3-bathroom home offers 2,035 sq. ft. of comfortable living space, perfect for families or anyone who loves to entertain. Featuring a newer roof (2021) and updated windows with stunning custom shutters, this home combines timeless charm with modern convenience.The kitchen is a chef’s dream, boasting solid wood

  David Coker KELLER WILLIAMS WINTER PARK

  1532 Lawndale Cir, Winter Park, FL 32792
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  /2

  $1,375,000 Sold May 28, 2025

  • 2,481 Sq Ft
  • $554/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1951

  1633 Pine Ave, Winter Park, FL 32789

  This home is a charming and meticulously maintained single-story family home nestled on a quiet street located on an expansive beautifully landscaped lot. As you enter, you're greeted by a private office with French doors to the left, and to the right, a cozy family room featuring a decorative fireplace. The open concept living and dining areas overlook the backyard, creating a perfect flow for

  Jenny Lake FANNIE HILLMAN & ASSOCIATES

  1633 Pine Ave, Winter Park, FL 32789
• 

  /2

  $535,000 Sold May 28, 2025

  • 1,945 Sq Ft
  • $275/SF
  • 35 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2003

  4200 Bear Gully Rd, Winter Park, FL 32792

  ACCEPTING BACK-UP OFFERS.....This is the one you've been waiting for! Located in Winter Park and on OVER HALF AN ACRE this lovely home is awaiting new owners. Step inside and notice the welcoming feeling, with NEW FLOORING throughout, TALL BASEBOARDS, built ins and appealing floor plan. The eat-in kitchen has been updated to include STAINLESS APPLIANCES, GRANITE COUNTERTOPS, backsplash, BREAKFAST

  Renee Killiri RED BIRD REALTY OF FLORIDA INC

  4200 Bear Gully Rd, Winter Park, FL 32792
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  /22

  $397,500 Sold May 28, 2025

  • 1,327 Sq Ft
  • $300/SF
  • 82 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  927 Mare Bello Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. LOCATION, LOCATION! Welcome to 927 Mare Bello Drive in Winter Park, Florida's highly desirable Eastbrook neighborhood. This peaceful and family-friendly community is renowned for its quiet streets and welcoming atmosphere. TOP-RATED SCHOOLS: Families will appreciate access to excellent educational institutions, including Winter Park High School.

  Susana Moor LA ROSA REALTY KISSIMMEE

  927 Mare Bello Dr, Winter Park, FL 32792
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  /2

  $190,000 Sold May 28, 2025

  • 1,117 Sq Ft
  • $170/SF
  • 163 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  7317 Forest Hill Ct Unit 235, Winter Park, FL 32792

  Reduced for a quick sell! Step into this captivating 3-bedroom, 2-bathroom second-floor end unit, nestled in a beatiful community. Spanning 1,117 square feet, this nicely upgraded home seamlessly blends style and comfort.Modern Upgrades: Enjoy a beautifully remodeled kitchen and bathrooms, featuring sleek finishes and high-quality materials.Open Concept Living: The spacious living and dining

  GOKHAN YILHAN COLDWELL BANKER RESIDENTIAL RE

  7317 Forest Hill Ct Unit 235, Winter Park, FL 32792
• 

  /2

  $1,340,000 Sold May 28, 2025

  • 5,500 Sq Ft
  • $244/SF
  • 293 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1967

  571 Lakefront Blvd, Winter Park, FL 32789

  Welcome to Winter Park lakefront living at its finest. Experience the ultimate lakefront lifestyle with year-round boating, kayaking and water skiing on your private lake in Florida. Lake Killarney is one of the few lakes in Central Florida where you can land your seaplane on the water. Winter Park offers a vibrant community rich in culture and amenities. From upscale dining and shopping to

  Harif Hazera PREMIER SOTHEBY'S INTL. REALTY

  571 Lakefront Blvd, Winter Park, FL 32789
• 

  /2

  $4,750,000 Sold May 27, 2025

  • 4,913 Sq Ft
  • $967/SF
  • 0 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1925

  984 Mayfield Ave, Winter Park, FL 32789

  Welcome home to a gated estate on one of the most desired streets in Winter Park, on a half-acre with a separate guesthouse & walk in wine cellar and tasting room, & a short distance to Park Avenue, Kraft Azalea Gardens and Winter Park Racquet Club. Timeless elegance and flawless artistry blend perfectly with modern comfort and function in this one-of-a-kind custom home originally designed for

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  984 Mayfield Ave, Winter Park, FL 32789
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  /2

  $575,000 Sold May 27, 2025

  • 972 Sq Ft
  • $592/SF
  • 24 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1952

  1230 N Denning Dr, Winter Park, FL 32789

  This charming “old Florida” bungalow in the heart of Winter Park offers the perfect blend of comfort and convenience, nestled in a prime location on a brick lined street just moments from world-class shopping and dining on famous Park Avenue. In addition, it is a short walk to both The Winter Park Village and Whole Foods. The warm and inviting interior of this home exudes character with original

  Ed Klein FANNIE HILLMAN & ASSOCIATES

  1230 N Denning Dr, Winter Park, FL 32789
• 

  /2

  $2,935,000 Sold May 27, 2025

  • 4,088 Sq Ft
  • $718/SF
  • 30 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 1930

  266 Chase Ave, Winter Park, FL 32789

  One of Winter Park’s iconic and cherished homes, just a short distance from Park Avenue. On one of the most picturesque, brick-lined streets in downtown Winter Park, this extraordinary residence is a rare opportunity to own a piece of the city’s rich architectural history, fully reimagined with modern elegance and thoughtful design. On the same city block as the Alfond Inn and a two-block stroll

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  266 Chase Ave, Winter Park, FL 32789
• 

  /2

  $685,000 Sold May 27, 2025

  • 2,446 Sq Ft
  • $280/SF
  • 53 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1979

  1321 Medinah Ct, Winter Park, FL 32792

  This incredible home has only ever had one owner! It's your opportunity to own .34 acres on a Winter Park cul-de-sac, complete with mature landscaping and backyard access to the Cady Way Trail. The oversized backyard has endless potential -- bring your ideas for a pool, an addition, or an amazing garden. Inside the home, you'll find a 4 bedroom, 2 bath split floor plan with multiple living space

  Courtney Pelfrey MILLER GRANT AND COMPANY

  1321 Medinah Ct, Winter Park, FL 32792

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