Winter Park FL Real Estate & Homes for Sale

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Beds:
3
Baths:
3.00
Sq.Ft.:
1,907
Status:
Active
MLS#:
O6276659
Type:
Townhouse
Subdivision:
Grayson Square
Lot size:
0.04 Acres
Year built:
2023
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

Step into this stunning townhome and be greeted by an open-concept kitchen, dining, and living area—perfect for entertaining. The modern kitchen is equipped with stainless steel appliances, sleek gray cabinets, and elegant quartz countertops. Upstairs, the Primary Bedroom features a spacious walk-in closet and a luxurious en-suite bathroom with a dual-sink quartz vanity and a private water closet. On the opposite side of the second floor, you’ll find two additional bedrooms, a secondary bathroom, and a convenient washer and dryer closet. Enjoy warm summer nights on your covered lanai, an ideal space to relax and unwind or host gatherings with family and friends. Located in the highly sought-after Winter Park, Grayson Square offers an unbeatable location just one mile from 436 and 434, and less than three miles from 417. Daily conveniences like Starbucks and Publix are just minutes away, with access to top-rated Seminole County Schools. Plus, the vibrant shopping and dining of Park Avenue is only a short drive away. With no CDD, this gorgeous townhome is perfect whether you're looking for your first home or a smart investment opportunity. Explore the possibilities today!

Beds:
3
Baths:
3.00
Sq.Ft.:
3,441
Status:
Active
MLS#:
O6276596
Type:
Single Family
Subdivision:
Charmont
Lot size:
0.26 Acres
Year built:
2011
A broker reciprocity listing Courtesy: OLDE TOWN BROKERS INC 407-425-5069
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ADDITIONAL INFORMATION

Elegant French Country Estate in Prestigious Winter ParkNestled in the heart of Winter Park’s picturesque, tree-lined streets near Lake Sue, this exquisite French Country estate blends timeless elegance with modern luxury. Situated on an oversized, gated lot, this stunning home offers privacy, sophistication, and an unparalleled living experience.The expansive primary suite, located on the first floor, is a private retreat with spa-like amenities. The open-concept living and dining areas flow seamlessly into the gourmet kitchen, complete with top-of-the-line gas appliances, custom cabinetry, and a separate catering kitchen—ideal for entertaining. The sun-drenched Florida room, surrounded by floor-to-ceiling windows and French doors, provides breathtaking views of the serene private patio and courtyard.A separate office/den on the first floor offers the perfect work-from-home space, while an elevator leads to the second-floor loft-style living area, two additional bedrooms, and a well-appointed Jack-and-Jill bathroom.The detached three-car garage provides ample storage and the opportunity to add a mother-in-law suite above, making this estate both functional and future-ready. The gated driveway and fully fenced property ensure security and exclusivity, all within one of Winter Park’s most sought-after neighborhoods.This is a rare opportunity to own a luxurious estate in a prestigious Winter Park location, surrounded by the beauty of the Lake Sue neighborhodd and just moments from the best shopping, dining, and cultural experiences the area has to offer.

Beds:
5
Baths:
6.00
Sq.Ft.:
4,227
Status:
Active
MLS#:
O6275888
Type:
Single Family
Subdivision:
Fontainebleau
Lot size:
0.32 Acres
Year built:
2003
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

Elegant 5-Bedroom Estate in the Heart of Winter Park. Nestled on a picturesque double lot in the highly sought-after Via’s, this stunning 5-bedroom, 4 full bath, 2 half bath traditional home offers over 4,200 sq. ft. of refined living space. With timeless architectural details, modern upgrades, and an unbeatable location just minutes from Park Avenue’s shops and restaurants, this home is a rare find. Step inside to find newly refinished Brazilian Rosewood floors throughout the main living areas. The formal living room features a wood-burning fireplace and two sets of French doors that open to a covered lanai with a remote-controlled motorized screen, perfect for seamless indoor-outdoor living. The formal dining room sets the stage for elegant entertaining, while the spacious open-concept kitchen overlooks the family room. Designed for the culinary enthusiast, the kitchen boasts an Italian porcelain island, a brand-new Kucht Professional 8-burner gas range/oven, double ovens, and a walk-in pantry. The family room offers another wood-burning fireplace and French doors leading to the screened-in saltwater heated pool, refinished just three years ago with new equipment. The first-floor primary suite is a true retreat, featuring serene pool views, a large walk-in closet with California Closet system, and a spacious en-suite bath. Two additional first-floor bedrooms, each with walk-in closets, provide comfort and convenience. Upstairs, a private bedroom, full bath, and large bonus room offer the perfect space for guests or a secondary living area, with easy access to walk-in attic storage. A two-car attached garage includes built-in storage and a private staircase leading to a guest apartment/bedroom suite complete with a wet bar and full bath—ideal for multi-generational living or an au pair. Outdoor living is at its finest with a covered lanai, new tile flooring, and a remote-controlled motorized screen, plus a poolside half bath and outdoor shower. Situated in a Grade A school district and offering easy access to major roadways, this exquisite home blends elegance, comfort, and prime location. Please see attachments for the full list of improvements.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,909
Status:
Active
MLS#:
O6276417
Type:
Single Family
Subdivision:
Charmont
Lot size:
0.26 Acres
Year built:
2015
A broker reciprocity listing Courtesy: MAINFRAME REAL ESTATE 407-513-4257
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ADDITIONAL INFORMATION

Welcome to 141 Oakwood Way, a one-of-a-kind custom-built estate in the highly desirable south Winter Park/Lake Sue area. This modern Mediterranean-inspired residence seamlessly blends timeless elegance with contemporary luxury, offering an exceptional living experience with high-end finishes, thoughtfully designed spaces, and unmatched attention to detail. Step inside to whitewashed oak wood and travertine flooring, setting the tone for a warm and sophisticated ambiance. The open floor plan begins with a private front office, ideal for remote work, and a guest suite with a full bath—perfect for visitors or multi-generational living. The first-floor primary suite serves as a private retreat, featuring direct access to the patio for a peaceful outdoor escape. The spa-like en-suite bathroom boasts dual vanities, a walk-in shower, and a freestanding soaking tub, while the custom-built walk-in closet offers elegant storage solutions. Thoughtful details, like built-in wiring for a wall-mounted TV, enhance both convenience and luxury. At the heart of the home is the gourmet kitchen, designed to impress with a solid walnut breakfast bar, quartzite, Carrara, and travertine countertops, Grohe faucets, and custom pullout/swivel cabinetry. A hidden pantry blends seamlessly into the custom cabinetry, while top-tier Thermador gas appliances, including a 42” refrigerator, make cooking a breeze. Flowing effortlessly into the family room and private courtyard, this space is perfect for entertaining. Upstairs, you'll find stunning Venetian plaster walls and a modern glass stair railing leading to a versatile loft space. Three additional bedrooms are located on this level, each featuring custom-built walk-in closets for optimal organization. One of the upstairs bedrooms includes a private en-suite, while the bonus loft opens to a covered balcony through elegant French doors, providing a tranquil indoor-outdoor retreat. Plush new carpeting in the bedrooms enhances the comfort and style of the upper level. Designed for seamless outdoor living, this home features a custom-built gas fire pit, summer kitchen, and outdoor grill, making it perfect for year-round entertaining. The expansive upstairs balcony offers additional entertainment space, large enough for a ping pong table, outdoor lounge, or media area. A two-car rear side-entry garage, connected to the main house by a charming esplanade walkway, offers both privacy and convenience while enhancing the home’s architectural beauty. The freshly painted exterior adds to the home’s pristine appeal, making it truly move-in ready. Located within one of Winter Park’s most desired school districts, this home is zoned for Audubon K-8 and Winter Park High School. Plus, you’re just minutes from East End Market and Park Avenue, with the area's finest dining, shopping, and cultural attractions. This is more than a home—it’s an expression of refined living and timeless design. Schedule your private tour today!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,262
Status:
Active
MLS#:
O6276171
Type:
Single Family
Subdivision:
Albert Lee Ridge
Lot size:
0.17 Acres
Year built:
1955
A broker reciprocity listing Courtesy: FLORIDA ONE REAL ESTATE LLC 407-599-7070
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ADDITIONAL INFORMATION

Tucked away on a quiet street yet just minutes from downtown Winter Park, College Park, and downtown Orlando, this beautifully updated 1955 ranch offers the perfect blend of peaceful living and urban convenience. With 2 bedrooms, 2 baths, and 1,262 square feet of thoughtfully renovated space, this home is move-in ready and full of character. As you enter, you’re greeted by a large, open living space that’s filled with natural light from the many windows. The spacious living room flows seamlessly into the dining area, making it perfect for both everyday living and hosting gatherings. The recently renovated kitchen is the heart of the home, showcasing sleek gray shaker cabinetry, black stainless steel appliances, quartz countertops, and a Mediterranean tile floor. It’s a bright and functional space where cooking and entertaining come together. The kitchen opens to the dining area, which leads out to a massive paver patio and a large, fully fenced backyard—ideal for outdoor relaxation, grilling, or even future expansion. The master bedroom is generously sized with space for a king-sized bed and features a built-in closet. A small but mighty ensuite bathroom with original vintage pink and grey tile adds charm and character to this space. The second bedroom is perfect as a guest room, children’s room, or home office. The second bathroom also embraces the vintage aesthetic with its green and white tile, while the bathtub has been reglazed and is ready for your next soak. Built with durable concrete block construction, this home offers low maintenance and energy efficiency. The one-car garage, accessed from the kitchen, provides ample storage space and houses the laundry area. The HVAC system was replaced in 2019, ensuring comfort year-round. Repipe done in 2020. Water heater replaced in 2020. Located just minutes from Winter Park’s renowned dining, boutique shopping, and cultural attractions, as well as being close to AdventHealth, Downtown Orlando, and major highways, this home offers the perfect balance of suburban tranquility and urban accessibility. With thoughtful updates already completed, this home is ready for its new owner. Don’t miss out on this opportunity to own in one of Central Florida’s most desirable neighborhoods.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,345
Status:
Active
MLS#:
TB8344901
Type:
Single Family
Subdivision:
Albert Lee Ridge 1st Add
Lot size:
0.17 Acres
Year built:
1956
A broker reciprocity listing Courtesy: HOME SOLD REALTY LLC 833-700-2782
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ADDITIONAL INFORMATION

Updated and remodeled 2+2+sunroom spacious single family home located in Winter Park's 32789 ZIP Code. This home offers easy access to I-4 and is located only a 1.5 miles from WP's upscale Publix, Whole Foods and the renovated Winter Park Village shopping/restaurant district, and it's only 2.2 miles from the city's crown jewel, Park Avenue. Home's amenities include stainless steel kitchen appliances (double-door refrigerator, oven/glass top stove, microwave and dishwasher), granite kitchen counters, new 2.5-ton Trane HVAC system, new hall bath shower, upgraded electrical box, updated tinted windows, fresh interior paint, spacious fenced backyard with no neighbors behind it, PEX pipe throughout, and well-maintained septic tank. Room dimensions are: Living Room — 19'x12' Kitchen — 10'x6 1/2' Master BR — 16'x11' 2nd BR — 13'x11' Sunroom — 12'x12 1/2' Dining — 10x9 1/2'

Beds:
4
Baths:
3.00
Sq.Ft.:
2,060
Status:
Active
MLS#:
TB8344918
Type:
Single Family
Subdivision:
Banks Colonial Estates
Lot size:
0.29 Acres
Year built:
1962
A broker reciprocity listing Courtesy: JACK KELLER INC 727-586-1497
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ADDITIONAL INFORMATION

Look at this rare opportunity to own a chic and trendy residence in winter park in an incredible location. You will be amazed at this fully remodeled one level four bedroom home on a fenced corner lot. This home has amazing curb appeal, with its wide half circle paved driveway, with plenty of parking flanked with lush mature landscaping. The open floor plan offers today's contemporary living and entertaining with designers porcelain tile, trendy light fixtures, plantation shutters and a family room with high vaulted ceilings. The designer kitchen has just been totally remodeled with Custom cabinets, Viking stainless steel appliances,custom vented hood and breakfast bar seating. To beautiful for words. A must see!! The spacious master bedroom suite boasts wood floors, 2 walk in closets duel vanities, a completely remodeled bathroom with a tiled shower and a separate soaking tub. The secondary bathroom, has been completely remodeled with marble flooring, double vanity sinks. The guest bedroom is its own en-suite. You will feel like you're on vacation when stepping out through the sliding glass doors leading to your private oasis with trex composite decking. The backyard was designed for entertaining and gathering around the wood burning fire pit, the summer kitchen with DCS gas grill, or just relaxing under the aluminum gazebo equip with fans. The entire home was remodeled in 2024. Short distance to Rollins College, Winter Park High school, Park Ave, Lake Virginia, the best restaurants, shopping and more. Don't miss out on this extraordinary property. Be sure and schedule a viewing.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,018
Status:
Active
MLS#:
O6276232
Type:
Condo
Subdivision:
Parkview Village
Lot size:
0.1 Acres
Year built:
1984
A broker reciprocity listing Courtesy: CREEGAN GROUP 407-622-1111
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ADDITIONAL INFORMATION

Welcome to your new home at 2935 Antique Oaks Cir Apt 64, a beautifully renovated 2-bedroom, 2-bathroom apartment in the heart of Winter Park, Florida. This second-floor unit offers a comfortable and convenient lifestyle with no upstairs neighbors, ensuring peace and privacy.   Key Features: Renovated Interior: Enjoy a fresh and modern living space with stylish LVP flooring throughout and sleek granite countertops in the kitchen and bathrooms. Spacious Layout: This well-designed apartment provides ample living space, perfect for individuals, couples, or small families. Second-Floor Unit: Benefit from added privacy and quietness with no neighbors above you. Prime Location: Situated in a highly sought-after area of Winter Park, this apartment offers easy access to a variety of amenities and attractions.   Conveniently Located Near: Full Sail University: Just a short drive away, this apartment is ideal for attendees, faculty, and staff of Full Sail University.   University of Central Florida (UCF): Reach UCF in no time for classes, events, or sporting activities. Valencia College: Enjoy close proximity to Valencia College for convenient access to higher education. Nearby Landmarks: Park Avenue: Explore upscale boutiques, restaurants, and entertainment options in this charming downtown area.   Winter Park Chain of Lakes: Discover scenic parks, walking trails, and water activities around the beautiful chain of lakes.   Rollins College: Visit this well known liberal arts college known for its beautiful campus and cultural events.   Community Amenities: Take a refreshing dip in the community pool on a hot day. Enjoy the well-maintained landscaping and serene atmosphere of the complex. Don't miss out on this fantastic opportunity to live in a renovated and conveniently located apartment in Winter Park!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,579
Status:
Active
MLS#:
O6275001
Type:
Single Family
Subdivision:
Winter Park Pines Rep
Lot size:
0.19 Acres
Year built:
1962
A broker reciprocity listing Courtesy: KELLER WILLIAMS WINTER PARK 407-545-6430
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ADDITIONAL INFORMATION

NEW ROOF in 2022! NEW HVAC AND DUCTWORK in 2023!! Welcome to the Winter Park Pines with its tree-lined streets, where the mailman still delivers to your door! This beautifully updated home on a private and established street will welcome you in with its bright and open floor plan. Recently renovated, this stunning 3-bedroom, 2-bathroom home is designed for both relaxation and entertaining. As you enter into the light and airy living space, you are greeted with newly wood-look tiled floors and fresh paint throughout in this open area. The kitchen offers all the modern conveniences with white cabinets with crown molding, stainless appliances and granite countertops. A convenient breakfast bar with seating for 3 provides the perfect accompaniment alongside the dining area offering comfortable eating space for family and friends. All 3 bedrooms are tucked away on the other side of the home with an ample level of privacy between them. Both bathrooms have been meticulously remodeled (11/2024). The ensuite bathroom offers a floating quartz vanity brand new expertly tiled shower with a custom glass divider. In the second bathroom, a new vanity with engineered quartz countertops, brand new toilet and tub/shower combination have been installed to provide a fresh and new feeling to the room. A set of sliding glass doors lead to a large back yard offering providing privacy and tranquility. You will find great storage in this home with two hall closets and built racks in the 2 car garage. Additional neighborhood amenities include the nearby Winter Pines Golf course, Cady Way Pool, tennis and pickleball courts, playground, Ward Park sports fields and MORE! The Wellness Center and Advent Health sit just outside of this community along with a plethora of grocery stores, restaurants, and shopping. Area colleges including Full Sail, Valencia, Rollins and UCF...all just minutes away. With its ideal blend of interior luxury and expansive outdoor living, it’s the perfect place to call home. HVAC - 2023, ROOF - 2022

Beds:
3
Baths:
2.00
Sq.Ft.:
1,242
Status:
Active
MLS#:
O6276257
Type:
Single Family
Subdivision:
Woodcrest Unit 5
Lot size:
0.22 Acres
Year built:
1973
A broker reciprocity listing Courtesy: CHARLES RUTENBERG REALTY ORLANDO 407-622-2122
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ADDITIONAL INFORMATION

Nestled in beautiful Winterpark this Cozy one story home offers a very spacious living room area as well as a second living room space that was built towards the back of home with a separate office room space. Kitchen has all appliances working including microwave and dishwasher and refrigerator and stove. Community is lovely, great neighbors! Extra room and office was build that adds APPROX. another 300 sq. feet to home. New roof was just installed approx. in 2021! Garage is very spacious and comes with Garage door opener. You will love this big yard and NO HOA fees ! Very easy to show !

Beds:
3
Baths:
3.00
Sq.Ft.:
1,397
Status:
Active
MLS#:
O6267093
Type:
Single Family
Subdivision:
Villas Of Casselberry Ph 3
Lot size:
0.07 Acres
Year built:
1994
A broker reciprocity listing Courtesy: KELLER WILLIAMS WINTER PARK 407-545-6430
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ADDITIONAL INFORMATION

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 reclaimed wood accents that are warm and welcoming. The wood accents are thoughtfully carried through to the dining room and offers the perfect space for family and friends to gather. An adjacent half bathroom has been remodeled with reclaimed wood-look tile. Enter the updated kitchen (12/2024) to find beautiful wood grain cabinets with new doors and stainless appliances, all less than 10 years old plus a brand new dishwasher (2024). Conveniently located on the main floor, the primary suite offers a beautiful bay window, spacious walk in closet, new carpeting (2024) and an ensuite bathroom with an updated shower (2024). Take the open staircase to the second floor which offers 2 bedrooms with the continued vaulted ceilings and bright bathroom redone with the same fabulous reclaimed wood-look tile. Other features that must not go overlooked are a brand new carbon monoxide detector, new A/C thermostat and a fire suppression system. Step outside to the open back yard and that continued attention to detail can be found with commercial-grade gutters and a Rain Bird irrigation system that keeps the landscaping vibrant year-round. The washer and dryer, less than 5 years old, are included. Your low monthly HOA fee allows you access to a community pool and a serene lake with a covered dock and gazebo, perfect for relaxing or socializing. This location puts you in close proximity to Downtown Winter Park, Park Avenue, Rollins College, Full Sail University, UCF, and Valencia College. Easy access to 436 with plenty of shopping, dining, and entertainment options are just minutes away. This home is a true gem, combining thoughtful updates, prime location, and a warm, welcoming atmosphere. Don’t miss the opportunity to make it yours! BRAND NEW ROOF - 2024, HVAC - 2024, WATER HEATER - 2017.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,688
Status:
Active
MLS#:
O6274967
Type:
Single Family
Subdivision:
Winter Park Pines
Lot size:
0.18 Acres
Year built:
1965
A broker reciprocity listing Courtesy: COLDWELL BANKER RESIDENTIAL RE 407-647-1211
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ADDITIONAL INFORMATION

Beautiful Winter Park 4 Bedroom/ 2 Bath home in the sought-after Winter Park Pines neighborhood! This lovely residence has a beautiful split floorplan with lots of natural light! This home offers both a separate family room and living room to provide ample space to entertain or enjoy a relaxing evening with the family. Dual sliding doors lead to a spacious screened lanai to enjoy the outdoors! Fully fenced backyard for privacy and security with plenty of room for a pool. Parking pad off the driveway for extra parking. New roof 2020!. Zoned for sought-after Winter Park schools! No HOA! Short ride to the Winter Pines public golf course with clubhouse and restaurant! Walking distance to the Cady way trail, pool and park. Easy access to Winter Park shopping, dining and restaurants as well as the Orlando International airport, UCF and Rollins college. Schedule your showing today!

Beds:
5
Baths:
5.00
Sq.Ft.:
2,964
Status:
Active
MLS#:
O6275847
Type:
Single Family
Subdivision:
Comstock Park
Lot size:
0.2 Acres
Year built:
2025
A broker reciprocity listing Courtesy: COMPASS FLORIDA, LLC 813-355-0744
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ADDITIONAL INFORMATION

Under Construction. Scheduled for completion in August 2025. This Luxurious Custom Home in the heart of Winter Park offers a perfect blend of luxury, function, and design. This custom built home offers 5 bedrooms, 4.5 bathrooms, and 2,964 sq/ft of unparalleled living space. From the moment you enter this home you are greeted by an elegant gallery entrance leading to an open-concept floor plan and a gourmet kitchen equipped with Thermador appliances, a wine storage space, quartz countertops, custom cabinetry, and engineered hardwood throughout. Off the kitchen is the trending scullery with a laundry/mudroom combination. This practical space is situated between the garage and kitchen offering functional convenience and privacy and includes a washer, dryer, and sink. The living room and dining areas provide an ideal setting for entertaining, equipped with a warm and inviting fire feature. A first floor owner's suite offers an expansive window package, oversized bedroom, a spa inspired bathroom with a soaking tub, dual sinks, stunning quartz countertops, and an oversized walk in closet with a custom closet system. Enhanced living features continue to the second floor where you will find a generous gathering/flex space, 4 additional bedrooms ideal for guests, family and one bedroom that could serve as a home office or exercise room, and two additional bathrooms with custom finishes. Expanding beyond the living room and dining area is a covered patio with a stunning summer kitchen complete with a grill, sink and granite counter tops, a resort-style pool all ideal for entertaining or simply relaxing. Conveniently located just 1.9 miles or 8 minutes from the vibrant Park Avenue, you'll have easy access to boutique shopping and fine dining. Call today for more information.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,295
Status:
Active
MLS#:
S5119543
Type:
Condo
Subdivision:
Cedarwood Village 1
Lot size:
0.05 Acres
Year built:
1983
A broker reciprocity listing Courtesy: EXP REALTY LLC 407-846-0940
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ADDITIONAL INFORMATION

This charming 2-bedroom, 2-bathroom condo offers 1,295 square feet of comfortable single-level living, thoughtfully designed for easy living and entertaining. The open floor plan boasts a spacious, sunlit living area and a well-appointed kitchen, perfect for culinary creations. Both bedrooms are generously sized and provide privacy, each featuring its own en-suite bathroom for added convenience. Enjoy low-maintenance living in a beautifully maintained community with easy access to local amenities, shopping, and dining—an ideal blend of style and function.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,747
Status:
Active
MLS#:
S5118820
Type:
Single Family
Subdivision:
Northwood Terrace
Lot size:
0.32 Acres
Year built:
1953
A broker reciprocity listing Courtesy: NAIM REAL ESTATE LLC 818-268-9917
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ADDITIONAL INFORMATION

An unparalleled opportunity to live in one of Orlando’s most desirable areas and in a truly dream-worthy home! This stunning 4-bedroom, 3-bathroom property, situated on a spacious 0.32-acre lot (13,814 square feet), has been completely remodeled with exceptional attention to detail. It boasts a custom Calacatta surface and brand-new stainless steel appliances, including a sleek glass cooktop, all cabinets come with soft-close drawers. The elegant two-tone cabinetry adds a custom touch that will impress your guests. The heart of the home is bathed in natural light thanks to a large front window in the dining area, creating an inviting atmosphere. Sliding glass doors connect the living space to the outdoor oasis, where you’ll find a spacious pool with a screened enclosure, a beautifully landscaped yard, and a cozy fire pit, perfect for relaxing or entertaining from the comfort of your own home. The dining area also features a convenient coffee bar that enhances functionality. Nestled in one of Winter Park’s most sought-after neighborhoods, this property is just minutes away from exclusive dining and boutique shopping. Zoned for top-rated Audubon K-8 and Winter Park High School, this neighborhood is a true gem, benefiting from its prime location and excellent schools, in an area experiencing rapid transformation.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,129
Status:
Active
MLS#:
O6274948
Type:
Single Family
Subdivision:
Winter Woods Unit 01
Lot size:
0.24 Acres
Year built:
1968
A broker reciprocity listing Courtesy: EMPIRE NETWORK REALTY 407-440-3798
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ADDITIONAL INFORMATION

Welcome to this recently UPGRADED HOUSE, Move-In Ready in the desired city of Winter Park with NO HOA. Seminole County is well known for its top-rated school district. This home has three spacious living areas (Living, Dining and Family Room).The Primary Bedroom has an en-suite bathroom completed RENOVATED with two sinks, beautiful Quartz countertops, and a walking shower. The Third Bedroom has a separate space, perfect for an office or nursery and a walking closet. The updated kitchen boasts contemporary finishes with granite countertops and brand new stainless steel appliances, the kitchen opens to the cozy family room that allows you enjoying cooking your favorite meal while watching your favorite show or game. Enjoy the evenings in the enclosed porch for a different enchanted atmosphere to unleashed after a work day while listening to the nature sounds. The house has just been repiped, Roof is 2011, HVAC is 2010. Located minutes from University of Central Florida UCF, Full Sail University, Rolling College, Downtown Orlando, Baldwin Park, Howell Park Center, and many other shopping centers. Approximately 30-45 minutes drive to Disney World, and Universal Studios. Schedule your private showing today, take the opportunity to own a piece of Winter Park Paradise in the desirable Sunshine State!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,560
Status:
Active
MLS#:
O6273477
Type:
Single Family
Subdivision:
Lake Bell Terrace
Lot size:
0.19 Acres
Year built:
1957
A broker reciprocity listing Courtesy: MILLER GRANT AND COMPANY 407-399-6031
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ADDITIONAL INFORMATION

Here's your opportunity to own a charming Winter Park bungalow with convenient access to 1792, I4, and all of the best shopping and dining in Winter Park, Maitland, and College Park. On the exterior of the home, you'll appreciate with the mature landscaping and the very low traffic, dead-end street that is Eland Ave. Notable systems include the roof, which was replaced in 2015, the 2018 windows, and the HVAC, which was replaced in 2022. In the backyard, the pool and hot tub provide an oasis environment that you're sure to fall in love with. The pool was resurfaced in 2023, along with new pavers, LED lighting, and tile so it looks and feels brand new! The hot tub was added in 2018 and will convey with the property. Inside, the space is perfect for entertaining and the layout is highly multifunctional. The kitchen overlooks the family room with all of its natural light and original wood flooring and there is a large bonus room, ideal for a home office or a playroom/secondary living space depending on the buyers' needs. 3 bedrooms and 2 bathrooms can be found down the hall. Additional upgrades to this property include windows, exterior LED lighting, and the irrigation system. This home is zoned for Hungerford Elementary, which is an OCPS Magnet Program for Advanced Curriculum (STEAM). In less than 10 minutes, you can get from this property to Park Avenue (6 minutes), Hannibal Square (7 minutes), Winter Park Village (5 minutes), Edgewater Drive (7 minutes), I-4 (3 minutes), Rollins College (10 minutes), and Lake Lily Park (6 minutes).

Beds:
4
Baths:
4.00
Sq.Ft.:
2,172
Status:
Active
MLS#:
O6275164
Type:
Single Family
Subdivision:
Lake Knowles Terrace
Lot size:
0.15 Acres
Year built:
2025
A broker reciprocity listing Courtesy: COMPASS FLORIDA, LLC 305-851-2820
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ADDITIONAL INFORMATION

Under Construction. Elegant and modern new construction home perfectly situated in beautiful Winter Park. Scheduled for completion in August 2025, this brand new construction home offers a perfect blend of luxury, comfort, and contemporary design. With 4 spacious bedrooms, 3.5 beautifully appointed bathrooms, and 2,172 square feet of meticulously crafted living space, this home is built to impress. Step inside and you are greeted with an amazing open-concept floor plan. The gourmet kitchen is a chef’s dream, featuring quartz countertops, custom cabinetry, top-of-the-line appliances, and an expansive island perfect for entertaining. The living and dining areas feature ample space for family gatherings or intimate dinner parties, with large windows that open up to stunning outdoor spaces. Each of the 4 bedrooms is generously sized, including a luxurious primary suite with a spa-like bathroom, dual vanities, a soaking tub, and a walk-in closet. Step outside to your private backyard oasis, complete with a sparkling pool, an expansive exterior lanai, and a gorgeous summer kitchen. Walk to Phelps Park or jump on your golf cart for a short trip to Park Avenue with its amazing restaurants and luxury boutique shops. The proximity of this house to everything there is to do in Winter Park is truly hard to beat. Don’t miss the opportunity to make this stunning Winter Park home yours.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,046
Status:
Active
MLS#:
O6273641
Type:
Single Family
Subdivision:
Kenilworth Shores Sec 04
Lot size:
0.21 Acres
Year built:
1964
A broker reciprocity listing Courtesy: NETWORTH REALTY OF ORLANDO, LLC 321-329-3127
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ADDITIONAL INFORMATION

Welcome to this stunning, fully updated home nestled in the desirable Winter Park area, just moments from the vibrant shops and dining on Park Avenue. This 4-bedroom, 2.5-bath home is a true gem, offering a perfect blend of modern style and classic charm. With a complete renovation, including a brand new AC system, this home is move-in ready and boasts a long list of luxurious upgrades. Step inside to discover brand-new luxury vinyl plank flooring throughout, providing both beauty and durability. The kitchen is a true showstopper, featuring all-new stainless steel appliances, sleek quartz countertops with a stunning waterfall edge, and custom cabinetry that provides ample storage and style. Each bathroom has been fully updated with unique contemporary finishes, ensuring your home is as functional as it is stylish. The generously primary suite offers a peaceful retreat, complete with a beautifully updated ensuite bathroom. Outside, you'll enjoy a fully fenced-in backyard, perfect for pets, outdoor dining, or just relaxing in privacy. The 2-car garage offers plenty of storage space, with separated access to the main living areas. Located in the heart of Winter Park, you'll have easy access to the best that the city has to offer—whether it's shopping and dining on Park Avenue, or enjoying the local parks and golf course. Plus, you'll have quick access to major highways like I-4 and SR-417, making commuting a breeze. Take advantage of this opportunity to own a beautifully renovated home in one of Winter Park's most sought-after neighborhoods—schedule your showing today!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,408
Status:
Active
MLS#:
O6273849
Type:
Single Family
Subdivision:
Hyde Park
Lot size:
0.14 Acres
Year built:
1986
A broker reciprocity listing Courtesy: STRICKLAND REALTY GROUP INC 407-448-5068
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ADDITIONAL INFORMATION

Welcome to your next home or an excellent investment opportunity at 3131 Ash Park Loop in the serene Hyde Park community. This inviting 2-bedroom, 2-bathroom house offers a clean, open split floor plan that’s perfect for both living and entertaining. Move-in ready, this home also presents a unique chance for creative renovations, making it a blank canvas for your personal touch. The property boasts a large screened-in patio area for enjoying the pleasant Florida weather and a fenced-in backyard that provides privacy and security. The open area across the street ensures the home is always bathed in natural light, with no possibility of construction blocking the view. Situated in the highly sought-after Hyde Park neighborhood, the home is just minutes from Downtown Winter Park, Maitland, UCF, Casselberry, and Winter Springs, blending suburban peace with urban convenience. Hyde Park is known for its peaceful environment and community amenities, including playgrounds, sports courts, walking paths, and a community dock on Lake Florence. With its superb location and promising features, 3131 Ash Park Loop is an ideal choice for anyone looking to invest in a property with both immediate appeal and long-term value.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,020
Status:
Active
MLS#:
O6275119
Type:
Condo
Subdivision:
Winter Park Woods Condo
Lot size:
0.2 Acres
Year built:
1974
A broker reciprocity listing Courtesy: RE/MAX ASSURED 800-393-8600
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ADDITIONAL INFORMATION

Spacious 2-bedroom, 2-bathroom offers a comfortable and convenient lifestyle in the heart of Winter Park. Enjoy the ease of in-unit laundry with a washer and dryer conveniently located in outside storage closet. Steps aways from mailboxes for effortless mail retrieval. Within close proximity to a vibrant array of dining and shopping options. Conveniently located near renowned educational institutions including Full Sail University, Rollins College, Valencia College, and the University of Central Florida (UCF). A short distance to the cultural hub of Downtown Orlando and the charming Park Ave district. Ideal for homeowners and investors. Contact us today to schedule a showing!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,074
Status:
Active
MLS#:
O6275033
Type:
Condo
Subdivision:
Winter Park Gardens Condo
Lot size:
0.03 Acres
Year built:
1964
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

This second floor unit features new luxury vinyl flooring, new appliances, granite counter tops, updated bathrooms, as well as upgraded fans and light fixtures. Come enjoy the stunning floor to ceiling pond views from the sunroom. This building has been replumbed as well. The complex is set in over 8 acres of lush gardens adorned with live oaks, lighted walking paths, pond and beautiful pool oasis. Winter Park Gardens is a vibrant 55+ community with room for younger owners and offers AN UNMATCHED LOCATION WALKABLE TO EVERYTHING WINTER PARK HAS TO OFFER. Experience all that makes Winter Park Gardens the best buy in Winter Park.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,393
Status:
Active
MLS#:
O6275067
Type:
Condo
Subdivision:
Whisperwood Condo
Year built:
1974
A broker reciprocity listing Courtesy: LUXE HUNTER REAL ESTATE 407-690-1414
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ADDITIONAL INFORMATION

Welcome to your Winter Park oasis! This charming 2-bedroom, 2-bathroom condo in the desirable Canford Court community offers comfortable living in a prime location. Step inside to discover a bright, airy, open floor plan, perfect for both relaxing and entertaining. The spacious living room features a dedicated den area – ideal for a home office or study. The updated kitchen boasts stainless steel appliances and granite countertops, making meal prep a breeze. Enjoy your morning coffee or evening cocktail on the private patio. Canford Court provides residents with a secure, gated environment and a fantastic Winter Park location. You'll be just moments away from the area's renowned shops, restaurants, parks, and cultural attractions. Don't miss this opportunity to experience the best of Winter Park living!

Beds:
2
Baths:
1.00
Sq.Ft.:
1,132
Status:
Active
MLS#:
O6272801
Type:
Single Family
Subdivision:
Orwin Manor Westminster Sec
Lot size:
0.17 Acres
Year built:
1949
A broker reciprocity listing Courtesy: KEYSEEKERS REAL ESTATE 727-490-9000
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ADDITIONAL INFORMATION

Welcome to 1424 Cavendish Road. This Beautiful 1940’s Pool Home is tucked between the tree-lined streets of highly desired, Orwin Manor, offering the perfect blend of classic appeal and modern convenience. Step into this charming home and experience its warm and inviting ambiance. The living room is bathed in natural light, with a cozy wood-burning fireplace that adds timeless character and comfort. Beyond, discover your personal backyard retreat—a serene oasis with mature landscaping, a spacious lounge area, and a private saltwater pool, perfect for summer relaxation. The refreshed kitchen is both stylish and functional, featuring granite countertops, newer appliances, updated sink and faucet, and GAS STOVE, complemented by an adjacent dining area. The two bedrooms are thoughtfully designed, separated by a fully remodeled bathroom boasting sleek modern tiles, a chic vanity, updated fixtures, and elegant lighting. This home also offers practical upgrades, including enhanced attic insulation, natural gas, and a tankless water heater for endless energy-efficient hot showers. Every detail has been considered to blend modern convenience with timeless charm. Orwin Manor is one of Winter Park’s most cherished neighborhoods, known for its tree-lined streets, historic homes, and central location. Residents love the community’s proximity to Park Avenue, Downtown Orlando and College Park. Enjoy the convenience of walking to Orange Avenue’s restaurants or take a quick drive to Park Avenue, Winter Park’s premier shopping and dining destination, where you can explore boutiques, favorite local restaurants, and charming coffee shops. For professionals, the location couldn’t be better. Major hospitals such as Advent Health Orlando and Orlando Health are within close proximity, providing excellent career opportunities and peace of mind for healthcare access. The area is also conveniently located near Downtown Orlando, making commutes to major corporate offices and job hubs a breeze. Experience the best of Winter Park living in a neighborhood that combines a serene suburban feel with the vibrancy of city life. Don’t miss the opportunity to make this Gem your new home!

Beds:
3
Baths:
1.00
Sq.Ft.:
1,292
Status:
Active
MLS#:
O6274702
Type:
Single Family
Subdivision:
Orange Terrace
Lot size:
0.2 Acres
Year built:
1954
A broker reciprocity listing Courtesy: OPENDOOR BROKERAGE LLC 480-462-5392
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Welcome to a delightful property that boasts a modern, neutral-colored paint scheme throughout. The kitchen is a chef's dream, equipped with all stainless steel appliances. The outdoor area is perfect for entertaining, featuring a deck and covered patio in the backyard. The property also includes a fenced-in backyard, providing privacy and security. The interior has been recently updated with fresh paint, adding to the overall appeal. This property is a true gem, offering comfort and sophistication.

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Andrea Conner, License #BK3437731, Xome Inc., License #1043756, [email protected], 844-400-9663, 750 State Hwy 121 Bypass, Suite 100, Lewisville, TX 75067


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Winter Park Real Estate

Winter Park is located in Florida. Winter Park, Florida has a population of 29,672. Winter Park is less family-centric than the surrounding county with 27.95% of the households containing married families with children. The county average for households married with children is 31.51%.

The median household income in Winter Park, Florida is $88,688. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Winter Park is 45.3 years.

Winter Park Weather

The average high temperature in July is 92 degrees, with an average low temperature in January of 49.4 degrees. The average rainfall is approximately 51.9 inches per year, with 0 inches of snow per year.

Winter Park Map

Winter Park Real Estate Market Conditions

  • Median sales price

    $469,250
    25.3%
    change since last quarter
  • # Active listings

    329
    30-day change

Winter Park Schools and Demographics

Education near Winter Park, FL

City County
High School Graduates 96.78 89.47
College Degree - 2 year 9.01 11.45
College Degree - 4 year 62.48 35.7
Graduate Degree 17.77 9.12
Expenditures per Student 12,701 12,701
Students per Teacher 17.3 17.3

Elementary Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Aloma Elementary School PK - 05 528 15.5 32792
Aspire Academy Charter KG - 05 111 8.5 32804
Audubon Park Elementary School PK - 05 1,182 14.8 32814
Brookshire Elementary School PK - 05 632 12.9 32792
Dommerich Elementary School PK - 05 603 15.1 32751
Eastbrook Elementary School PK - 05 809 14.2 32792
Fern Creek Elementary School PK - 05 326 12.1 32803
Hillcrest Elementary School PK - 05 463 14.5 32803
Hungerford Elementary School PK - 05 283 13.5 32751
Killarney Elementary School KG - 05 444 14.8 32789
Lake Silver Elementary School PK - 05 688 12.3 32804
Lake Sybelia Elementary School PK - 05 600 13.3 32751
Lakemont Elementary School KG - 05 656 14.6 32792
Orlando Science Elementary Charter KG - 05 482 15.1 32804
Princeton Elementary School PK - 05 488 13.2 32804

Middle Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Glenridge Middle School 06 - 08 1,415 18.4 32814
Maitland Middle School 06 - 08 909 18.9 32751
Robert E Lee Middle 06 - 08 1,034 17.2 32804

High Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Edgewater High School 09 - 12 1,782 20 32804
Lake Howell High School 09 - 12 2,229 19.1 32792
Winter Park High School 09 - 12 3,069 18.7 32792
Workforce Advantage Academy Charter 09 - 12 238 47.6 32803

Ungraded Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
* Aloma High Charter School 09 - 12 510 42.5 32792
* Winter Park Education Center 11 - 12 0 32789
Broward Science Charter School UG - UG 0 32804
Central Florida Leadership Academy Charter 06 - 12 189 15.8 32803
Gateway 06 - 12 63 3.7 32804
Hospital Homebound PK - 12 229 4 32804
La Amistad School KG - 12 48 9.6 32751
Orlando Science Middle High Charter School 06 - 12 555 15.4 32804
Pace Center for Girls 06 - 12 34 6.8 32803
Silver Star Center 06 - 12 25 2.5 32804
Winter Park Tech AE - AE 0 32789

Demographics near Winter Park, FL

City County
Neighborhood Type Suburban
Population 29,672 1,409,949
Population Density 3,393 1,562
Median Age 45.3 35.7
People per Household 2.3 2.9
Median Household Income 88,688 65,784
Average Income per Capita 67,032 33,498

Real estate near Winter Park