Winter Park, FL Homes for Sale with No HOA Fee

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  /42

  $1,795,000

  • 4 Beds
  • 4 Baths
  • 2,807 Sq Ft

  1903 N Park Ave, Winter Park, FL 32789

  Completed in 2020, this beautifully designed contemporary residence on North Park Avenue offers refined finishes and seamless indoor-outdoor living just minutes from Park Avenue’s famed shopping and restaurant district as well as the vibrant retail and dining of Winter Park Village and Mills50. Positioned on a prominent corner lot with dual access from N Park Ave and N Denning Drive, the home

  Chris Creegan CREEGAN GROUP

  1903 N Park Ave, Winter Park, FL 32789
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  /11

  $1,800,000

  • Land
  • 0.3 Acre
  • $6,000,000 per Acre

  1181 Via Capri, Winter Park, FL 32789

  Build your dream home in one of Winter Park’s most desirable areas. This exceptional vacant lot at 1181 Via Capri offers a rare opportunity to create a custom residence in a well-established neighborhood known for its charm, convenience, and strong property values. Ideally located just minutes from Park Avenue, top-rated schools, dining, shopping, and major roadways, this homesite provides both

  Ana Semmel KARDOSH REALTY

  1181 Via Capri, Winter Park, FL 32789
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  /29

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,405 Sq Ft

  2779 Sanbina St, Winter Park, FL 32789

  Rare opportunity in the heart of 32789 — priced under $500K, this 3-bedroom, 2-bathroom Winter Park home delivers the location, lot, and bones that buyers in this zip code rarely find at this price point. Zoned for Dommerich Elementary and Winter Park High School and situated on a generous 0.23-acre lot, this is the one worth moving quickly on. Upon entry, a sun-drenched living room leads to a

  Caroline Fiore MAINFRAME REAL ESTATE

  2779 Sanbina St, Winter Park, FL 32789
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  /57

  $1,970,000

  • 5 Beds
  • 4.5 Baths
  • 4,363 Sq Ft

  1177 Kenwood Ave, Winter Park, FL 32789

  Welcome to 1177 Kenwood Ave, a home that blends warmth, comfort, and thoughtful design. The inviting living room features a cozy fireplace, creating the perfect space to relax on cooler evenings. The kitchen is designed with both style and function in mind, stainless steel appliances and a center island ideal for meal preparation and gathering. The spacious primary suite serves as a retreat,

  Karen Albright OPENDOOR BROKERAGE LLC

  1177 Kenwood Ave, Winter Park, FL 32789
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  /5

  $724,900

  • Land
  • 0.54 Acre
  • $1,342,407 per Acre

  1034 Turner Rd, Winter Park, FL 32789

  Rare opportunity to build your dream home on the shores of highly sought-after Lake Bell in the desirable 32789 Winter Parkzip code. This exceptional waterfront parcel offers direct access to one of the area’s beautiful skiable lakes, providing theperfect setting for luxury lakefront living. The current owners have already completed significant groundwork, includingprofessionally

  Parker Blanchard OLDE TOWN BROKERS INC

  1034 Turner Rd, Winter Park, FL 32789
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  /19

  $929,900

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  2823 Wright Ave, Winter Park, FL 32789

  Rare opportunity to own a beautifully upgraded lakefront property on half acre in one of Winter Park's most desirable locations. This homesite offers the perfect setting to enjoy the current residence or build your future dream home! When you step inside you'll find a thoughtfully updated kitchen featuring high-end appliances, custom cabinetry, and designer finishes. The home boasts new windows

  Tal Busidan TAL BUSIDAN PA

  2823 Wright Ave, Winter Park, FL 32789
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  /52

  $3,495,000

  • 4 Beds
  • 6 Baths
  • 4,683 Sq Ft

  1581 Forest Ave, Winter Park, FL 32789

  Just steps from the charm and energy of Park Avenue, this exceptional Winter Park residence was completely rebuilt in 2018 by renowned custom builder Posada Homes, member of the elite Master Custom Builders Council. Offering a rare blend of modern design, crisp architectural lines, and timeless elegance, on an expansive 0.39-acre lot along one of Winter Park's most picturesque tree-lined streets.

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  1581 Forest Ave, Winter Park, FL 32789
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  /11

  $440,000

  • 4 Beds
  • 2 Baths
  • 1,296 Sq Ft

  Unlisted Address

  Beautifully updated 4-bedroom, 2-bath home in a premium Winter Park location with NO HOA and a spacious backyard. This home is currently in the final phase of renovation and has already undergone major upgrades, including remodeled bathrooms, updated kitchen, new flooring, upgraded electrical, and a newer roof. The interior has been thoughtfully modernized, offering a bright open layout ideal for

  Arlenys Oviedo EXP REALTY LLC

  Unlisted Address
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  /22

  $399,999

  • 2 Beds
  • 1 Bath
  • 987 Sq Ft

  3505 Corrine Dr, Orlando, FL 32803

  Live steps from everything that makes the Audubon Park Garden District one of Orlando’s most sought-after neighborhoods. Located along Corrine Drive, this mid-century home in Audubon Park offers unbeatable shopping, dining, and local favorites including the beloved East End Market. As you arrive, the classic mid-century character and welcoming curb appeal set the tone. Inside, the home feels

  Kathryn Stelljes KELLER WILLIAMS REALTY AT THE PARKS

  3505 Corrine Dr, Orlando, FL 32803
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  /28

  $600,000

  • 3 Beds
  • 2 Baths
  • 1,618 Sq Ft

  218 Orange Terrace Dr, Winter Park, FL 32789

  Come see this charming pool home on a desirable corner lot near Lake Killarney in Winter Park. This beautifully maintained mid-century residence features 3 bedrooms and 2 baths with warm wood floors and timeless character throughout. The private, fully fenced backyard is turfed for low maintenance and perfect for relaxing and entertaining. Major updates provide peace of mind, including new

  Arden Magee ANNE ROGERS REALTY GROUP INC

  218 Orange Terrace Dr, Winter Park, FL 32789
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  /24

  $542,000

  • 4 Beds
  • 2 Baths
  • 2,126 Sq Ft

  3131 Lowndes Dr, Winter Park, FL 32792

  Enjoy the Winter Park Lifestyle with this Beautiful 4 Bedroom Poolside Home. [Appointment Only] Fully Updated/ Move-in Ready! Open Floorplan with Entryway into the Living and Dining area that overlooks your Screen-Enclosed Pool/ outdoor Living Space with a Fenced Yard. Entertain in style with a Large Eat-In Kitchen, Stainless Steel Appliances, Soft-Close Cabinetry and Quartz Countertops. Enjoy

  Rene' Fossey A +ROI PROPERTY

  3131 Lowndes Dr, Winter Park, FL 32792
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  /68

  $2,279,000

  • 5 Beds
  • 4.5 Baths
  • 2,889 Sq Ft

  240 N Phelps Ave, Winter Park, FL 32789

  Brand new construction luxury home in the heart of Winter Park! This stunning two-story custom residence offers nearly 3,000 sq ft of heated living space with 5 bedrooms and 4 1/2 bathrooms. A soaring two-story foyer creates a dramatic first impression and opens into an expansive great room featuring 12-foot ceilings, wide-plank flooring, and abundant natural light. The family room showcases a

  Milena Fernandes GOLDEN GROUP REALTY LLC

  240 N Phelps Ave, Winter Park, FL 32789
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  /65

  $2,450,000

  • 4 Beds
  • 5 Baths
  • 5,051 Sq Ft

  2550 Venetian Way, Winter Park, FL 32789

  Chain of Lakes Water- Front Home with Private Boat Dock, Winter Park Luxury Living. Step into your future with this extraordinary custom built residence, inspired by the artistic richness of Fernando Botero. From your back lanai, step directly onto your private, custom boat dock featuring a covered, remote-operated boat lift, and cruise the Venetian Canal with direct access to WinterPark’s

  Felicia Donateli PALM PROPERTIES OF CF, INC.

  2550 Venetian Way, Winter Park, FL 32789
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  /6

  $795,000

  • Land
  • 0.22 Acre
  • $3,613,636 per Acre

  325 N Phelps Ave, Winter Park, FL 32789

  Fantastic lot opportunity to build in one of Winter Park’s prime neighborhoods. Bring your vision and your builder to design a home tailored to your lifestyle on this 64-by-150-foot lot. The property includes a two-bedroom, one-bath single-family home with approximately 1,400 square feet of living space, making it an ideal potential income-producing property while you finalize your plans. Whether

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  325 N Phelps Ave, Winter Park, FL 32789
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  /57

  $1,899,900

  • 4 Beds
  • 3 Baths
  • 2,842 Sq Ft

  1521 Chestnut Ave, Winter Park, FL 32789

  Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, thoughtfully constructed in 2023 by the original owner/builder, located in one of Winter Park’s most sought-after neighborhoods. Designed with sleek sophistication and functional elegance, this fabulous home offers 4 bedrooms, 3 full baths, and a flexible layout perfect for today’s lifestyle. The open-concept

  Sue Silberbusch COMPASS FLORIDA LLC

  1521 Chestnut Ave, Winter Park, FL 32789
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  /44

  $2,200,000

  • 4 Beds
  • 3.5 Baths
  • 3,472 Sq Ft

  2423 Via Sienna, Winter Park, FL 32789

  Welcome to 2423 Via Sienna, gracefully positioned on a quiet cul-de-sac in the heart of Winter Park. This charming, established enclave is just moments from the Winter Park Racquet Club, Phelps Park, the YMCA, and the renowned boutiques and dining of Park Avenue.This exceptional four-bedroom, three-and-a-half-bath pool residence has been taken to the studs and masterfully reimagined with

  Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  2423 Via Sienna, Winter Park, FL 32789
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  /39

  $599,900

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft

  1354 Indiana Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle.The beautifully

  Ellen Bessette CHARLES RUTENBERG REALTY ORLANDO

  1354 Indiana Ave, Winter Park, FL 32789
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  /39

  $3,350,000

  • 5 Beds
  • 6 Baths
  • 4,636 Sq Ft

  2040 Randall Cir, Winter Park, FL 32789

  Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a functional floor plan. Framed by manicured landscaping and connected to a detached two-car garage by a covered walkway, the home offers classic curb appeal in an idyllic setting just minutes from vibrant shopping and dining on Park

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2040 Randall Cir, Winter Park, FL 32789
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  /47

  $634,500

  • 3 Beds
  • 2 Baths
  • 1,785 Sq Ft

  2708 Lion Heart Rd, Winter Park, FL 32792

  Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning

  Navid Rokh EQUITYPRO LLC

  2708 Lion Heart Rd, Winter Park, FL 32792
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  /61

  $1,795,000

  • 5 Beds
  • 3.5 Baths
  • 3,304 Sq Ft

  2501 Winter Park Rd, Winter Park, FL 32789

  A masterfully crafted custom residence in the heart of Winter Park, this 2014 Barefoot Brothers home blends timeless architecture with modern functionality just moments from Park Avenue and the Audubon Park Garden District. Designed for both refined entertaining and active everyday living, this 5-bedroom + office home offers a flexible, family-focused floor plan plus an expansive second floor

  Jill Healey KELLER WILLIAMS WINTER PARK

  2501 Winter Park Rd, Winter Park, FL 32789
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  /58

  $6,900,000

  • 6 Beds
  • 7 Baths
  • 6,396 Sq Ft

  1260 Alabama Dr, Winter Park, FL 32789

  Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue.From the

  Kelly Price KELLY PRICE & COMPANY LLC

  1260 Alabama Dr, Winter Park, FL 32789
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  /34

  $1,399,000 Open Thu 4PM - 6PM

  • 4 Beds
  • 3.5 Baths
  • 2,509 Sq Ft

  2454 Brookshire Ave, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to this aesthetic custom luxury home in an unbeatable Winter Park location.From the moment you arrive, the custom landscaping and automated lighting make a statement, day or night.At the center of the home, the chef's kitchen is both a showpiece and a performance space. A commanding 48-inch Z-Line gas range with 8 Italian-made brass burners

  Norma Gonsalves COLDWELL BANKER REALTY

  2454 Brookshire Ave, Winter Park, FL 32792
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  /47

  $6,450,000

  • 5 Beds
  • 5.5 Baths
  • 5,476 Sq Ft

  1200 Via Salerno, Winter Park, FL 32789

  Along one of the cobblestone brick streets in the prestigious Via’s of Winter Park, this completely renovated residence pairs timeless European influence with clean architectural lines and bespoke finishes throughout. A circular driveway and manicured grounds designed by Signature Landscapes create a graceful approach. Inside, a dramatic curved staircase crowned by a breathtaking 1960s vintage

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1200 Via Salerno, Winter Park, FL 32789
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  /68

  $850,000

  • 5 Beds
  • 3 Baths
  • 2,242 Sq Ft

  1927 Eland Ave, Winter Park, FL 32789

  *Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations, or rental

  Ryan Leitter CHARLES RUTENBERG REALTY ORLANDO

  1927 Eland Ave, Winter Park, FL 32789
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  /26

  $1,395,000

  • 2 Beds
  • 3 Baths
  • 2,096 Sq Ft

  1500 Harris Cir, Winter Park, FL 32789

  Tucked along one of Winter Park’s charming brick streets and positioned directly across from Lake Sylvan, this recently renovated residence unfolds like a quiet design story, one where character, craftsmanship and modern ease are aligned. From the moment you arrive, the home’s inviting curb appeal and reimagined cottage gardens set the tone, offering a sense of arrival that feels timeless and

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1500 Harris Cir, Winter Park, FL 32789
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  /36

  $384,900

  • 4 Beds
  • 2 Baths
  • 1,988 Sq Ft

  3330 Coleus Ct, Winter Park, FL 32792

  Situated in an established Winter Park neighborhood, this single-family residence offers a functional layout with generous living space designed for everyday comfort. The home features multiple living areas that provide flexibility for daily living, entertaining, or work-from-home needs. Conveniently located near major roadways, public transit, shopping, dining, and surrounding Central Florida

  Raquel Littlejohn MAINSTAY BROKERAGE LLC

  3330 Coleus Ct, Winter Park, FL 32792
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  /45

  $1,645,000

  • 5 Beds
  • 5.5 Baths
  • 3,609 Sq Ft

  234 Detmar Dr, Winter Park, FL 32789

  Nestled behind gates in the heart of Winter park, this enchanting 1930's residence blends historic charm with many recent upgrades. The beautifully renovated kitchen anchors the home, while the downstairs primary suite offers privacy and comfort with an elegant spa inspired bath. The detached one bedroom guest house is perfect for houseguests, a home office or multi-generational living. The main

  Nicole Seybold FANNIE HILLMAN & ASSOCIATES

  234 Detmar Dr, Winter Park, FL 32789
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  /32

  $775,000

  • 4 Beds
  • 3.5 Baths
  • 3,062 Sq Ft

  675 Overspin Dr, Winter Park, FL 32789

  Seller may consider buyer concessions if made in an offer ~ Beautiful upgrades, a versatile layout, and the best of Winter Park at your doorstep! With Dubsdread Golf Course just around the corner and Fairbanks Avenue minutes away, this 4-bedroom, 3.5-bath CUSTOM BUILT HOME puts you in the center of it all – NO HOA required! Major systems have been well maintained; including a NEW A/C UNIT with UV

  Jennifer Wemert WEMERT GROUP REALTY LLC

  675 Overspin Dr, Winter Park, FL 32789
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  /35

  $299,999

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  3204 Netherwood Dr, Winter Park, FL 32792

  Discover this beautifully renovated 2-bedroom, 1.5 -bathroom villa in the heart of Winter Park! Nestled on a private cul-de-sac lot with no HOA, this home has been completely upgraded to offer modern comfort and style. Step inside to luxury vinyl flooring throughout, an open-concept living space, and a sleek kitchen with stainless steel appliances. The high-end bathroom remodel adds a spa-like

  Renee Anthony WATSON REALTY CORP.

  3204 Netherwood Dr, Winter Park, FL 32792
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  /77

  $1,950,000

  • 5 Beds
  • 4.5 Baths
  • 4,288 Sq Ft

  4469 Old Bear Run, Winter Park, FL 32792

  Private, gated lakefront living on Bear Gully Lake one of Winter Park’s most desirable spring-fed ski lakes. Set on an expansive 137-acre body of water, this custom residence offers a rare combination of privacy, scale, and true Florida waterfront lifestyle. A circular driveway behind a private gate welcomes you to a thoughtfully renovated home designed to capture sweeping lake views. Bear Gully

  Keigan Lewis LPT REALTY, LLC

  4469 Old Bear Run, Winter Park, FL 32792
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  /19

  $2,000,000

  • 3 Beds
  • 2 Baths
  • 2,148 Sq Ft

  2036 Via Tuscany, Winter Park, FL 32789

  WINTER PARK VIA’S!!! Incredible Oversized Lot is located in the “Heart” of Winter Park. Very Unique opportunity in Winter Park for a high-quality custom build. The brick lined lighted street with sidewalks is located across from the Winter Park Racquet Club. This location is a wonderful opportunity to build your Estate Home. The lot size is 112’ X 140’. Value is in the land.

  Mark Medei KELLY PRICE & COMPANY LLC

  2036 Via Tuscany, Winter Park, FL 32789
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  /36

  $925,000

  • 4 Beds
  • 2 Baths
  • 2,250 Sq Ft

  1521 Heron Wood Place, Winter Park, FL 32792

  Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides immediate income for a hands-on owner or family-run operation.One structure is currently utilized for daycare operations, while the second structure is a single-family home that offers excellent potential for future daycare

  Ronald Trotter RE/MAX INNOVATION

  1521 Heron Wood Place, Winter Park, FL 32792
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  /24

  $1,050,000

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

  1836 Grinnell Terrace, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Beautifully renovated home in the heart of highly desirable Winter Park, surrounded by multi-million-dollar properties. Move-in ready and thoughtfully updated throughout. Set on an expansive lot approximately 79 x 152 (11,305 square feet) provides plenty of space to build your future dream home! This light-filled home features wide-plank flooring,

  Cindy Kuykendall FANNIE HILLMAN & ASSOCIATES

  1836 Grinnell Terrace, Winter Park, FL 32789
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  /9

  $1,595,000

  • 3 Beds
  • 2 Baths
  • 2,012 Sq Ft

  1113 Via Del Mar, Winter Park, FL 32789

  Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceablehomesite offering rare scale, privacy, and extraordinary future build potential. The primaryvalue is in the land, presenting an unparalleled canvas for a custom luxury residence, withvirtually no comparable vacant land available in the immediate vicinity. Set on a tranquil smalllake that

  David Barany BAY HILL REALTY LLC

  1113 Via Del Mar, Winter Park, FL 32789
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  /75

  $2,950,000

  • 4 Beds
  • 4.5 Baths
  • 4,129 Sq Ft

  151 Oakwood Way, Winter Park, FL 32789

  Welcome to 151 Oakwood Way. This is a rare Winter Park showpiece by LunDev Custom Homes, tucked on a quiet, tree-lined street in the heart of Winter Park. This newer luxury pool home delivers the perfect blend of timeless architecture and modern comfort, pairing clean transitional design with warm, high-end selections and true Florida indoor/outdoor living. Inside, a bright open-concept floor

  Matthew Burks CORCORAN PREMIER REALTY

  151 Oakwood Way, Winter Park, FL 32789
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  /18

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 1,881 Sq Ft

  4872 N Orange Ave, Winter Park, FL 32792

  3 bedroom 3 bathroom pool home. Enjoy the large backyard. Schedule your showing today!

  Thai Nguyen ALFA REAL ESTATE LLC

  4872 N Orange Ave, Winter Park, FL 32792
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  /30

  $456,000 Open Wed 9AM - 7PM

  • 4 Beds
  • 2 Baths
  • 2,264 Sq Ft

  2052 Leanne Ct, Winter Park, FL 32792

  Welcome to 2052 Leanne Ct, a home that exudes warmth and elegance. The living room is graced with a cozy fireplace, perfect for those chilly evenings. The kitchen is a chef's dream, boasting all stainless steel appliances for a sleek, modern look. The primary bedroom is a haven of comfort with double closets for ample storage. The primary bathroom is a sanctuary with double sinks, providing ample

  Karen Albright OPENDOOR BROKERAGE LLC

  2052 Leanne Ct, Winter Park, FL 32792
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  /64

  $2,295,000

  • 5 Beds
  • 4.5 Baths
  • 3,963 Sq Ft

  2015 N Park Ave, Winter Park, FL 32789

  Boasting a prestigious Park Avenue address, this striking modern architectural residence perfectly balances bold design with spa-like serenity. Set on a beautifully landscaped corner lot, the home embodies the rare combination of privacy and proximity, just a leisurely 25-minute stroll from Park Avenue’s world-class boutiques and dining. Every element of the design has been meticulously curated

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  2015 N Park Ave, Winter Park, FL 32789
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  /73

  $3,549,995

  • 4 Beds
  • 5 Baths
  • 3,658 Sq Ft

  1742 Temple Dr, Winter Park, FL 32789

  A New Standard of Modern Sophistication in Winter ParkIn a city known for its heritage, this ground-up architectural renovation emerges as a bold statement of modern luxury. Located within one of Winter Park’s most coveted enclaves, this four-bedroom, five-bathroom residence is not merely a place to live, but a meticulously crafted experience where high-design meets intuitive living.Step

  Mark Anthony Buot ROI AVE LLC

  1742 Temple Dr, Winter Park, FL 32789
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  /31

  $495,000

  • 3 Beds
  • 2 Baths
  • 2,028 Sq Ft

  3207 Lowndes Dr, Winter Park, FL 32792

  Easy access to all of Winter Park, UCF, and south Seminole County from this convenient, central location! If you've been searching for a spacious pool home with plenty of space for playing, entertaining, or even working from home -- you've found it here! When you walk in, you'll appreciate the intuitive flow of living space into the kitchen, with built-in eating space. Off of the kitchen, you'll

  Courtney Pelfrey MILLER GRANT AND COMPANY

  3207 Lowndes Dr, Winter Park, FL 32792

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