Winter Park FL Real Estate & Homes for Sale

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Beds:
3
Baths:
3.00
Sq.Ft.:
1,787
Status:
NEW LISTING
MLS#:
O6398259
Type:
Townhouse
Subdivision:
Aloma Trails
Lot size:
0.07 Acres
Year built:
2017
A broker reciprocity listing Courtesy: OLYMPUS EXECUTIVE REALTY INC 407-469-0090
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ADDITIONAL INFORMATION

Experience the perfect blend of luxury and convenience in the highly sought-after GATED community of Aloma Trails. This meticulously maintained 3-bedroom, 2.5-bathroom townhome, built in 2017, offers 1,787 sq. ft. of living space designed for comfort and modern style. Step inside to find an inviting open-concept first floor featuring beautiful ceramic tile flooring and high ceilings. The gourmet chef’s kitchen is a true standout, boasting upgraded granite countertops, a stylish tiled backsplash, 42” solid wood cabinetry, and a large island with plenty of breakfast bar seating. The full suite of stainless steel appliances makes this kitchen as functional as it is beautiful. The second level features plush carpeting throughout the bedrooms for ultimate comfort. The oversized Master Suite is a private sanctuary, complete with a massive walk-in closet and a spa-like en suite bathroom featuring a glass-enclosed shower, dual-sink vanity, and expansive cabinetry. Two additional well-appointed bedrooms share a second full bath, while the dedicated interior laundry closet adds a layer of daily convenience. Uniquely positioned with a spacious 2-car garage and a private paved driveway, this home easily accommodates multiple vehicles. The community of Aloma Trails provides a true "lock-and-leave" lifestyle with hassle-free lawn care and pristine common areas included in the HOA. Active lifestyles will thrive with the Cady Way Trail and Cross Seminole Trail just steps from your front door. For fitness buffs, Crunch Fitness is located directly across from the community entrance. Retail: 3 minutes to Walmart, Costco, and Publix. Education: Zoned for top-rated Seminole County Schools and minutes from UCF and Full Sail University. Entertainment: Short drive to the world-class dining and shopping of Park Avenue in Winter Park. Commute: Easy access to SR 417 puts you at the airport in 20 minutes or the beach in just 40! Don't miss your chance to own a piece of Winter Park luxury in a premier gated enclave.

Open House:

Sunday, 4/12 12:00-2:00PM

More Open House Info >

Beds:
3
Baths:
2.00
Sq.Ft.:
1,575
Status:
NEW LISTING
MLS#:
O6396985
Type:
Single Family
Subdivision:
Village Green
Lot size:
0.29 Acres
Year built:
1972
A broker reciprocity listing Courtesy: KELLER WILLIAMS ADVANTAGE REALTY 407-977-7600
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ADDITIONAL INFORMATION

***Multiple Offers Received. Please submit your highest and best offer by Monday, April 13th at 12 noon.***Buyer incentives you don't want to miss! This home qualifies for a 1% lender credit with our preferred lender. Location meets affordability with this rare opportunity in Winter Park with no HOA! With some TLC, this 3 bedroom, 2 bath home offers endless potential to make it your own. Major updates provide peace of mind, including a metal roof (2014), water heater (2024), and updated electrical panel (2012). Situated on a spacious .28 acre lot, the property features a fully fenced backyard- perfect for pets, play, or future outdoor living enhancements. Inside, you'll find a functional layout with a split-bedroom floor plan, a generous living room, and a separate family room for added flexibility. The kitchen offers ample cabinet space and room for casual dining. A 2 car garage and extended driveway provide plenty of parking. Ideally located near top rated Seminole County schools, with convenient access to UCF, SR 417, shopping, dining, and area attractions. Dont miss this incredible opportunity to own in a prime location with room to grow! Schedule your showing today!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,031
Status:
NEW LISTING
MLS#:
O6397477
Type:
Condo
Subdivision:
Hidden Oaks Condo Ph 04
Lot size:
0.01 Acres
Year built:
1983
A broker reciprocity listing Courtesy: BEYCOME OF FLORIDA LLC 804-656-5007
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ADDITIONAL INFORMATION

Welcome home to this beautiful starter home or perfect student housing in Winter Park! Two story townhouse style condo with 2 bedrooms each with private full ensuite bathroom and an extra half bath on the main floor. Renovated with stone counters and all luxury plank flooring- no carpet! New appliances and a nice open kitchen with breakfast bar- very unusual in this development. Washer and dryer in unit. Private fenced back patio with outdoor storage and small front garden for your green thumb. Only 15 min to UCF, 5 min to Full Sail and near all major shopping and dining including COSTCO, Target, Publix and more. Winter Park schools.

Open House:

Sunday, 4/12 12:00-3:00PM

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
3,057
Status:
NEW LISTING
MLS#:
O6397250
Type:
Single Family
Subdivision:
Lakeside Estates
Lot size:
0.23 Acres
Year built:
2015
A broker reciprocity listing Courtesy: KELLER WILLIAMS ADVANTAGE REALTY 407-977-7600
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ADDITIONAL INFORMATION

Welcome to refined Florida living in the highly sought-after gated community of Lakeside Estates, one of Winter Park’s most exclusive neighborhoods, where homes rarely come to market. With only 39 residences, this intimate lakefront community offers a level of privacy, prestige, and curb appeal that is increasingly difficult to find. From the moment you pass through the impressive gated entrance framed by a beautifully designed pond, elegant stone wall, and striking fountain, you immediately sense that Lakeside Estates is something special. This Mediterranean-inspired residence showcases timeless architectural design with a stunning stone-accented tower entry, graceful arched architecture, and a classic barrel tile roof, all complemented by a beautifully maintained paver driveway and a welcoming 8-foot front door. Inside, thoughtful craftsmanship is evident throughout, with colonial-style crown molding, designer finishes, and wood-look porcelain plank tile flooring that delivers the warmth of hardwood with exceptional durability. At the heart of the home, the chef’s kitchen is designed for both everyday living and entertaining, featuring white shaker cabinetry with crown molding, quartz countertops with elegant marble-inspired veining, stainless steel appliances, and a double oven. A beautifully appointed butler’s pantry with a built-in wine rack enhances both convenience and sophistication. The versatile floor plan includes a dedicated office, four bedrooms, spacious living areas, and generously sized rooms, creating flexibility for modern lifestyles. The primary suite provides a private retreat with spa-inspired features and ample storage. Step outside to your own backyard oasis featuring an enclosed saltwater pool, peaceful water views, and pre-plumbing for a future outdoor kitchen, making this outdoor space ideal for year-round entertaining. A convenient full pool bath provides easy access for guests while enjoying the outdoor living areas. Additional highlights include wall-mounted garage storage, kayak storage, and thoughtful design details throughout. Residents of Lakeside Estates enjoy access to a community dock where fishing and kayaking are possible, along with a playground and beautifully maintained common areas, all supported by an HOA that maintains the entrance and shared spaces. Ideally located in Winter Park and zoned for highly regarded schools, this home offers a rare opportunity to own within a private gated community where availability is limited, and demand remains strong.

Open House:

Sunday, 4/12 12:00-2:00PM

More Open House Info >

Beds:
2
Baths:
2.00
Sq.Ft.:
1,320
Status:
NEW LISTING
MLS#:
O6397291
Type:
Other
Subdivision:
Winter Park Pines Patio Homes
Lot size:
0.09 Acres
Year built:
1986
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Renovated 2 bedroom, 2 bathroom villa in a prime Winter Park location, ready for its next owner. Walk into a spacious, light and bright foyer with fresh interior paint and sliding doors that lead out to the patio, bringing in tons of natural light. The seller has removed all popcorn ceilings (a huge upgrade), and the property features laminate flooring throughout most of the main living areas. The main living space has vaulted ceilings and an open layout with room for both living and dining, and sliding glass doors leading out to the patio. The kitchen has been updated with new stainless steel appliances and new countertops, and offers a closet pantry along with a bay window that brightens the space. The primary suite is set toward the back of the home with high ceilings, its own sliding doors to the patio, a walk-in closet, and a renovated bathroom with a large walk-in shower. The split floor plan places the second bedroom near the front by the foyer, with a renovated full bathroom just next to it—great for guests or a home office. The backyard offers a blank canvas to create your own oasis, with a covered patio, a large screened porch, and a fully fenced private yard—hard to find with a villa! Additional highlights include a one-car garage with washer/dryer hookup, new light fixtures, and fresh interior paint. Located in the Winter Park Pines just minutes from iconic Park Avenue shopping and dining and downtown Winter Park. Across from Full Sail and a short drive to UCF. Call today to schedule your private showing!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,589
Status:
NEW LISTING
MLS#:
O6396971
Type:
Single Family
Subdivision:
Landings At Hawks Crest
Lot size:
0.11 Acres
Year built:
2021
A broker reciprocity listing Courtesy: U S GLORY REALTY 407-222-7801
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ADDITIONAL INFORMATION

Nestled in one of the most sought-after neighborhoods in Winter Park, this exceptional gated residence offers the perfect blend of elegance, comfort, and modern efficiency. Ideally located just five minutes from top-rated private schools, this two-story single-family home is designed for both luxurious living and everyday functionality. Upon entry, you are welcomed by a dramatic grand foyer featuring soaring ceilings of nearly 20 feet, creating an impressive and light-filled living space. The open layout seamlessly connects the main living areas, ideal for entertaining and family gatherings. This thoughtfully designed home features 4 spacious bedrooms and 3.5 bathrooms, including dual primary suites—one conveniently located on the main level and another upstairs—providing flexibility for multi-generational living or guest accommodations. A dedicated private office on the first floor offers the perfect work-from-home environment. Step outside to a beautifully maintained backyard with premium artificial turf, fully fenced for privacy, and a screened rear patio—perfect for relaxing or enjoying Florida’s outdoor lifestyle year-round. Extensively upgraded throughout, the home showcases high-quality finishes with no carpet—featuring elegant flooring and tile across all living areas, along with a solid wood staircase that adds warmth and sophistication. The garage is equally well-appointed with a premium epoxy-coated floor, offering both durability and a clean, polished look. Energy efficiency is a standout feature of this home, equipped with a tankless water heater for on-demand hot water and reduced energy consumption, as well as solar panels that help significantly lower utility costs. This is a rare opportunity to own a meticulously upgraded home in a prime Winter Park location—ideal as a primary residence or a high-potential investment property.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,296
Status:
NEW LISTING
MLS#:
O6396498
Type:
Single Family
Subdivision:
Eastgate Sub
Lot size:
0.24 Acres
Year built:
1955
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

Excellent opportunity to build your dream home in Winter Park. 10,278 SqFt corner lot. Value is in the Land, home being sold AS-IS. Zoned for Lakemont, Maitland Middle, Winter Park High. Centrally located near restaurants, shopping, Winter Park Hospital & a short drive to Park Avenue, Rollins College & many local parks. This sale is strictly for the value of the land & location.

Open House:

Wednesday, 4/15 9:00-12:00PM

More Open House Info >

Beds:
3
Baths:
2.00
Sq.Ft.:
1,518
Status:
Active
MLS#:
S5147029
Type:
Single Family
Subdivision:
Oakcrest-516
Lot size:
0.21 Acres
Year built:
1983
A broker reciprocity listing Courtesy: DREAM HOME REALTY GROUP AND ASSOCIATES LLC 407-504-7282
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ADDITIONAL INFORMATION

Short Sale. Short Sale – Subject to Lender Approval. Exceptional investment opportunity in the desirable Winter Park area. This property offers strong potential for value-add through renovation or repositioning. Located in an established community with no HOA, the home sits on a generously sized lot, providing flexibility for improvements and long-term upside. The current layout presents a solid starting point for updates, making it suitable for rental income, resale, or portfolio expansion. Conveniently positioned near shopping, dining, parks, and major roadways, with access to highly regarded schools and surrounding amenities. Winter Park continues to experience steady demand, supporting long-term investment potential. Property is being sold as-is. Buyer to verify all measurements, condition, and intended use. Don’t miss this opportunity to secure a property with upside in a sought-after Central Florida location.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,003
Status:
Active
MLS#:
O6395355
Type:
Single Family
Subdivision:
Greenview At Winter Pines
Lot size:
0.22 Acres
Year built:
1981
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW Wood & porcelain tile flooring throughout. Updates include (but definitely not limited to) BRAND new kitchen with Stainless Steel Appliances, new cabinets & quartz countertops. Formal living & dining rooms PLUS Family room with vaulted ceilings featuring a new electric fireplace for amazing ambiance and sliding doors inviting you to new brick pavered 31x 11 screened porch overlooking newly refinished sparkling pool & golf course (no rear or side neighbors!!) Bedroom wing of home offers a large inside laundry room, beautiful guest/pool bath with dual sinks & shower/tub and 2 fresh guest bedrooms. THE PRIMARY SUITE has been thoughtfully remodeled with sliding doors to pool, AMAZING primary bath with oversized work-of-art shower with dual shower heads, dual vanity, separate water closet & HUGE walk-in closet! Extras include: NEW double paned windows & 3 sliding doors to pool/patio, crown molding, NEW roof November 2024, oversized 2 car garage, NEW landscaping, all NEW ceiling fans & light fixtures, NO HOA!! Zoned for Brookshire Elementary, Glenridge Middle & Winter Park High. WELCOME HOME!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,020
Status:
Active
MLS#:
O6392376
Type:
Single Family
Subdivision:
Meadows At Hawks Crest
Lot size:
0.14 Acres
Year built:
2020
A broker reciprocity listing Courtesy: MARK SPAIN REAL ESTATE 855-299-7653
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ADDITIONAL INFORMATION

This beautiful home is in the gated Hawk’s Crest community of Winter Park. Built in 2020, the spacious layout gives everyone plenty of room to spread out featuring NO CARPET and a LARGE SCREENED LANAI. With TWO PRIMARY SUITES, this is the perfect home for multigenerational living! The open floor plan is perfect for everyday living and entertaining, with a beautiful kitchen that flows into the main living area and plenty of natural light throughout the home. The primary suite offers a comfortable retreat, and the additional bedrooms provide flexible space for guests, family, or a home office. Step outside to a private backyard with room to relax or entertain. Residents of Hawk’s Crest enjoy GATED ENTRY and AMPLE COMMUNITY AMMENITIES, including a pool, clubhouse, fitness center, playground, and access to Lake Howell with a community dock and kayak launch. Conveniently located near shopping, dining, major roads, and TOP-RATED SEMINOLE COUNTY SCHOOLS, this home offers the best of comfort, location, and community living.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,196
Status:
Active
MLS#:
O6395298
Type:
Other
Subdivision:
Winter Park Pines Patio Homes
Lot size:
0.36 Acres
Year built:
1988
A broker reciprocity listing Courtesy: SUN PROPERTIES, INC. 407-645-5700
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ADDITIONAL INFORMATION

Tucked away on a quiet cul-de-sac in highly sought-after Winter Park, this beautifully updated three bedroom, two bathroom duplex offers the perfect blend of comfort, style, and location—just steps from Winter Park Pines Golf Club. Once inside you discover open living spaces featuring warm wood flooring throughout the living areas and bedrooms, complemented by vaulted ceilings in the main areas and ceiling fans that enhance the home’s airy feel. The brand-new kitchen has tile flooring and is not only functional, but beautiful showcasing classic shaker cabinets, sleek quartz countertops, and stainless steel appliances—perfect for both everyday living and entertaining. There are three nice sized bedrooms, all with large closets. The primary bedroom features sliding glass doors that lead directly to the large backyard and open patio. Both bathrooms have been renovated with modern finishes, including new vanities, countertops, tub/showers, plus durable and stylish luxury vinyl plank flooring. Situated on a generously sized corner lot, the property offers plenty of outdoor space to enjoy, along with a charming paver front patio and the convenience of a one-car garage with opener. You will love the privacy of this end unit on the quiet cul-de-sac. Enjoy the ease of walking to nearby schools and being just moments from golf, shopping, dining, and all that Winter Park has to offer. With low HOA dues and located in a top-rated school district, this is an incredible opportunity in one of Central Florida’s most desirable neighborhoods.

Beds:
5
Baths:
6.00
Sq.Ft.:
3,655
Status:
Active
MLS#:
O6393049
Type:
Single Family
Subdivision:
Brookshire Heights
Lot size:
0.23 Acres
Year built:
2026
A broker reciprocity listing Courtesy: CORCORAN PREMIER REALTY 407-965-1155
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ADDITIONAL INFORMATION

Under Construction. A rare opportunity to own brand-new construction in desirable Brookshire Heights, this thoughtfully designed residence blends timeless finishes with modern functionality. Featuring 5 bedrooms, a dedicated office, and a spacious bonus room, the floor plan is both highly livable and exceptionally functional—ideal for everyday living and entertaining alike. All bedrooms are ensuite, offering comfort and privacy throughout, while hardwood floors run seamlessly across the entire home. Thoughtful architectural details, including custom ceiling treatments and built-ins, add depth and character throughout. The first-floor primary suite serves as a true retreat, complete with dual shower heads and a rain shower for a spa-like experience. In addition to the primary, the secondary bedrooms and office are all conveniently located on the first floor—providing a layout that lives comfortably day-to-day. Upstairs, you’ll find three spacious bedrooms, each with its own full bath, along with a generous bonus room and a large laundry room—offering flexibility for guests, family, or additional living space. Perfectly positioned within steps to Brookshire Elementary, the home is also just moments from the Cady Way Trail, Little League fields, parks with covered pavilions, and nearby medical facilities. Shopping, dining, and everyday essentials are just minutes away, with Park Avenue’s renowned restaurants and boutiques a short drive from your doorstep. A seamless blend of location, thoughtful design, and livability, this home offers an exceptional opportunity in one of Winter Park’s most established neighborhoods.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,529
Status:
Active
MLS#:
O6390829
Type:
Single Family
Subdivision:
Eastbrook Sub Unit 14
Lot size:
0.24 Acres
Year built:
1968
A broker reciprocity listing Courtesy: RE/MAX 200 REALTY 407-629-6330
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ADDITIONAL INFORMATION

This home sits at the end of a cul-de-sac with an attractive courtyard entry to the 2 car garage. The Kitchen has been updated with new cabinets and tile flooring and the baths all have tile flooring. The Primary Bedroom has Luxury Vinyl Flooring. The screened porch overlooks a spacious fenced backyard that includes a block building (summer cottage) with electric and plumbing that is currently being used for storage. The Roof was replaced in 2022 and the yard has a sprinkler system. Make an appointment to see today!!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,038
Status:
Active
MLS#:
O6394524
Type:
Single Family
Subdivision:
Winter Park Pines Rep
Lot size:
0.21 Acres
Year built:
1963
A broker reciprocity listing Courtesy: RE/MAX TOWN & COUNTRY REALTY 407-695-2066
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Fully reimagined and COMPLETELY RENOVATED with Custom features, this stunning 4-br, 3-ba home in desirable Winter Park Pines sits proudly on a spacious corner lot and offers Modern Luxury with thoughtful, HIGH END UPGRADES throughout. The interior showcases all-new cabinetry and countertops, highlighted by a dramatic waterfall kitchen island, brand-new appliances including a built-in microwave tucked into a custom pantry cabinet. Every detail has been carefully considered, from new luxury vinyl flooring and interior doors to upgraded closet shelving, sleek bathroom mirrors, and stylish shower enclosures. Sound insulation enhancements in key areas—including the primary suite, bathrooms, and kitchen walls—provide added comfort and privacy, while smart ceiling fans, dimmable lighting, USB charging outlets, and pre-wiring for under-cabinet lighting and wall-mounted TVs bring modern convenience to everyday living. Beyond the interior, the home continues to impress with major system upgrades and durable exterior improvements designed for long-term peace of mind. Enjoy a BRAND NEW ROOF with transferable warranty, updated soffit and fascia, rot-proof siding and porch columns, and new fiberglass exterior doors with built-in blinds. The property also features a new irrigation system, vinyl fencing, and an expansive 3+ car driveway. Behind the walls, everything has been upgraded—including full electrical rewiring with a new 200-amp service, all-new plumbing from underground lines to fixtures, and a high-efficiency HVAC system with new ductwork and insulation for maximum energy savings, making this home truly MOVE-IN READY with no detail overlooked. FYI-Dumpster to be removed and pressure washed and Install of PVC fence w/ gate at driveway on 04/09.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,366
Status:
Active
MLS#:
S5146768
Type:
Single Family
Subdivision:
Howell Branch Woods
Lot size:
0.21 Acres
Year built:
1978
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

Rare No-HOA home with NEW ROOF 2022 and dedicated HOME OFFICE/FLEX SPACE! This move-in-ready 3-bedroom, 2-bathroom residence offers 1,366 sq ft of smart living plus an bonus room perfect for remote work, creative studio, or guests—functionality of four spaces without the 4-bedroom price premium.Enjoy zero HOA restrictions, significant monthly savings, and peace of mind with a 3-year-old roof (transferable documentation included). Features include updated flooring throughout (no carpet), fully fenced backyard, and 2-car garage. Zoned for desirable Seminole County schools (Eastbrook Elementary/Lake Howell High) with quick access to SR-436, shopping, and downtown Winter Park. Ideal for remote professionals, small families, or savvy buyers seeking low-maintenance ownership with room to work and grow. Quick closing available. Schedule today!

Open House:

Sunday, 4/12 1:00-3:00PM

More Open House Info >

Beds:
2
Baths:
2.00
Sq.Ft.:
1,266
Status:
Active
MLS#:
O6395720
Type:
Condo
Subdivision:
Four Seasons Condo
Lot size:
19.03 Acres
Year built:
1970
A broker reciprocity listing Courtesy: KELLER WILLIAMS WINTER PARK 407-545-6430
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ADDITIONAL INFORMATION

Welcome to this spacious and well-maintained 2 story townhome in the heart of Winter Park, located in the highly sought-after Four Seasons community. This 2-bedroom, 1.5-bath unit offers 1,266 square feet of comfortable living space with a functional layout, abundant natural light, and thoughtful updates throughout. Step inside to find a spacious kitchen, renovated in 2016, featuring wood cabinetry, granite countertops, black appliances, and a dishwasher replaced in 2023, perfect for everyday cooking and entertaining. Just off the kitchen, enjoy a dedicated dining area, ideal for hosting dinners or creating a flexible space for a home office or additional seating. The inviting living room provides plenty of space to relax and gather, with sliding glass doors that lead to your private, fully fenced, tree-shaded patio complete with a storage shed - an ideal spot to enjoy your morning coffee or unwind in the evenings. The patio also offers convenient access to your covered, deeded carport space, #49. Both bedrooms are generously sized, with the primary bedroom featuring dual closets and a ceiling fan for added comfort. The home includes a full bathroom and a convenient half bath, both thoughtfully updated with new toilets and upgraded vanities, including a quartz countertop and stylish shiplap accent in the guest bath. Additional interior highlights include custom closet features, a laundry closet with a new stackable washer and dryer(included), ceiling fans and blinds throughout, fresh interior paint (2024), and an HVAC system updated in 2023, providing peace of mind and modern convenience. Residents of Four Seasons enjoy access to a variety of amenities including 3 swimming pools, a clubhouse with fitness center, tennis and shuffleboard courts, all within a quaint, established neighborhood with tree-lined walkways. Ideally located just minutes from Ward Park, Winter Park Pines Golf Club, YMCA, AdventHealth Winter Park, and the Center for Health & Wellbeing. Enjoy easy access to shopping and dining along Aloma Avenue including Publix, Sprouts, and Aldi, as well as being less than 10 minutes from Park Avenue’s renowned restaurants and boutiques. Conveniently located near SR 436 with quick access to 417 and 408, and approximately 25 minutes to Orlando International Airport. Zoned for top-rated schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. Don’t miss your opportunity to own in one of Winter Park’s most desirable communities—schedule your private showing today!

Beds:
2
Baths:
1.00
Sq.Ft.:
854
Status:
Active
MLS#:
O6394406
Type:
Townhouse
Subdivision:
Windward Square Sec 3
Lot size:
0.1 Acres
Year built:
1979
A broker reciprocity listing Courtesy: FLORIDA HOME TEAM REALTY LLC 407-774-8100
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ADDITIONAL INFORMATION

CHARMING 2/1 MOVE IN READY TOWNHOME in highly sought-after Windward Square community of Winter Park! NEWER Roof 2025! Spacious floor plan with soaring ceilings! Inviting entertainment space with dining/living combo off kitchen. Ample natural light fills this home with double glass sliders and multiple skylights all in living area! Relaxing views of back park like green space! Convenient location near major highways, the Orlando International Airport, shopping, dining, universities and only 30 min to attractions! Property has 2 parking spaces directly in front for easy access! Community boast various amenities include a pool, tennis courts, clubhouse, and playground! DON"t MISS out on this RARE OPPORTUNITY! A VALUE FOR THIS MARKET INDEED! TRULY A MUST SEE!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,589
Status:
Active
MLS#:
O6394208
Type:
Single Family
Subdivision:
Meadows At Hawks Crest
Lot size:
0.11 Acres
Year built:
2021
A broker reciprocity listing Courtesy: BHHS FLORIDA REALTY 352-729-7325
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium solar system you own outright, paying for your electricity. (Ask to see the bill.) Imagine relaxing on your private, expanded lanai, soaking in the breathtaking sunsets. Your spacious 4-bedroom, 3.5-bathroom home offers premium views of nature, and is just steps away from the community resort clubhouse. With gated access, Hawks Crest Residence enjoy an abundance of amenities, including a resort pool and fitness center, sidewalks and playgrounds throughout. And for those seeking adventure, enjoy dock access to Lake Howell, complete with a canoe/kayak launch. Daily, residents can relax and unwind while the management association takes care of all landscaping around the home, ensuring that residents can enjoy true maintenance-free living. The state-of-the-art off-grid solar system is equipped with battery backup with a 30-year warranty transferable to new owners. And this home is pre-wired for electric vehicles with room to expand. Excess power produced is sold back to the power company through the “Net Metering” program. Additionally, upgrades include heavy-duty commercial luxurious vinyl wide-plank flooring, two power monitoring systems, a whole-house water softener & filter system, along with 8-foot doors all designed for comfort, convenience and a peaceful home where you can relax. Nestled in this spacious home, you’ll find 20-foot-high ceilings and breathtaking views of the illuminated fountain from various rooms, creating a serene and relaxing atmosphere you’ll enjoy, even from the kitchen sink. And with a smart-winch lift, your chandelier maintenance is a breeze. (Rated up to 200lbs) Uniquely designed, this home was built to withstand extreme weather conditions, featuring concrete/granite tile roof, along with a steel reinforced, concrete-filled block walls and slab, all anchoring to the foundation that uniquely ties everything together, ensuring the utmost strength and safety for your family. Owners have meticulously maintained this home and comes with floor plans, a complete set of blueprints, along with photos of the home during the building process, and even includes documents for all equipment and appliances. The premium solar system comes with a 30-year warranty, including scheduled updates like the new power panel, installing April 2026. And yes, the warranty is transferable to new owners. This home features a split floor plan, with a primary bedroom on the first floor and a second primary bedroom upstairs. Spanning 2,589 square feet, the home also includes an additional 540 square feet of screened-in lanai (18x30), providing a private outdoor space to enjoy sunsets while overlooking the resort water features and landscaping. Schedule a showing for your buyers today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,574
Status:
Active
MLS#:
O6395138
Type:
Single Family
Subdivision:
Howell Estates Rep
Lot size:
0.24 Acres
Year built:
1974
A broker reciprocity listing Courtesy: KELLER WILLIAMS WINTER PARK 407-545-6430
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ADDITIONAL INFORMATION

Welcome to this well-maintained three-bedroom, two-bathroom home offering 1,574 square feet of thoughtfully designed living space in the established and highly desirable Howell Estates neighborhood of Winter Park. From the moment you enter, an abundance of natural light, ceiling fans throughout, and a functional layout create an open and inviting atmosphere. The flexible floor plan includes a dedicated family room/den in addition to a formal dining area, providing versatile space for entertaining, working from home, or everyday living. Blinds throughout, generous closet space, and sliding glass doors leading to the backyard add both comfort and practicality. The kitchen blends classic style with everyday convenience, featuring blond-toned wood cabinetry, a closet pantry, and newer stainless steel appliances including a refrigerator, dishwasher, and microwave(2024). The layout connects seamlessly to the surrounding living spaces, making it ideal for both daily use and hosting. The primary suite serves as a private retreat, complete with a ceiling fan and an ensuite bathroom featuring a single vanity, a tiled walk-in shower with glass sliding doors, and a newly updated toilet. The two additional bedrooms are well-sized and versatile, perfect for family, guests, or a home office, and share a hall bathroom with a single vanity, tiled tub/shower combination, and a new toilet. Outdoor living is enhanced by a spacious and open 0.24-acre fully fenced lot, offering plenty of room for relaxation, entertaining, or future additions. The exterior has been freshly painted and features brand-new landscaping completed in 2026, creating excellent curb appeal. A two-car garage with a new garage door provides additional convenience and storage. Significant updates offer peace of mind, including a roof installed in 2020, electrical updates completed in 2020, HVAC system installed in 2017, and a water heater replaced in 2023. Ideally located, this home is just 7 minutes from Red Bug Lake Park, close to top-rated schools, and within close proximity to restaurants, grocery stores, and retail shopping—offering the perfect blend of comfort, convenience, and location. Roof – 2020 HVAC – 2017 Electrical – 2020 Water Heater – 2023

Beds:
3
Baths:
3.00
Sq.Ft.:
1,680
Status:
Active
MLS#:
O6385950
Type:
Single Family
Subdivision:
Winter Park Pines Ut 5
Lot size:
0.21 Acres
Year built:
1964
A broker reciprocity listing Courtesy: SOTERA LIVING 407-725-9660
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ADDITIONAL INFORMATION

Beautifully renovated solid block home on a quiet street in highly desirable Winter Park Pines! This property features fresh exterior paint, updated lighting, a newly paved courtyard, and a bright open floor plan. The stunning kitchen offers modern cabinetry, quartz countertops, and brand-new stainless steel appliances, flowing seamlessly into the dining and family rooms. The sun-drenched Florida room is lined with windows that brighten the entire living space. Complete with a dry bar and its own mini-split AC unit, it offers flexible space for entertaining, relaxing, or creating your dream retreat. The split floor plan includes three generously sized bedrooms and three full renovated bathrooms, with a private primary suite with walk-in closet off the family room and the additional bedrooms and bath located on the opposite side of the home. The attached two-car garage offers excellent potential to be converted into a fourth bedroom, utilizing the existing full bathroom to create a private mother-in-law suite or guest quarters. Additional upgrades include new flooring, trim, doors, fixtures, and fresh interior paint. Create your own outdoor oasis with a newly paved patio and large fenced backyard with room for a pool. Ideally located near downtown Winter Park, Park Avenue shopping and dining, Cady Way Trail, and zoned for top-rated schools. Schedule your showing today!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,117
Status:
Active
MLS#:
O6393643
Type:
Single Family
Subdivision:
Tanglewood Sec 4
Lot size:
0.31 Acres
Year built:
1955
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 407-647-1211
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ADDITIONAL INFORMATION

***WINTER PARK **** 4 BEDROOMS ****3 BATHROOM **** PAID OFF SOLAR ***** WILL HELP BUYER****METAL ROOF ***1/3 ACRE*** Welcome to 1923 Linden Rd, Winter Park—a well-maintained single-story residence offering space, character, and an exceptional location. Built in 1955, this solid masonry and concrete block home features 4 bedrooms, 3 full bathrooms, and approximately 2,117 heated square feet, with 2,281 total building square feet. Located in the highly desirable area of Winter Park, the home provides convenient access to shopping, dining, parks, and top-rated schools, as well as nearby Park Avenue and downtown Orlando. The interior offers a functional layout with multiple living areas, ideal for both everyday living and entertaining. Original character elements such as plaster interior walls and two fireplaces add warmth and timeless appeal. The centrally located kitchen provides ample workspace and flows seamlessly into the main living areas. Situated on a generous 0.315-acre lot (13,717 sq ft) with approximately 117 feet of frontage and 114 feet of depth, the property offers plenty of room for outdoor enjoyment, future enhancements, or expansion. Additional features include Metal Roof that allows for 20 degrees cool, continuous footing foundation, and package cooling system. A strong opportunity for buyers seeking a well-built home with character, space, and long-term value in a prime location.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,495
Status:
Active
MLS#:
S5146437
Type:
Condo
Subdivision:
Cedarwood Village 1
Lot size:
0.03 Acres
Year built:
1984
A broker reciprocity listing Courtesy: EXP REALTY LLC 407-846-0940
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ADDITIONAL INFORMATION

Welcome to this charming 2-bedroom, 2-bath condo with a versatile loft, perfectly situated just minutes from shopping and the vibrant downtown Winter Park area! This light-filled end unit offers an open floor plan with vaulted ceilings and skylights, creating a bright and airy feel throughout. You’ll appreciate the newer flooring, crown molding, and the comfortable, functional layout. Relax and unwind on the private back porch—an ideal outdoor sitting space. The kitchen features a pantry and cozy breakfast nook. The spacious primary suite includes a walk-in closet, updated bathroom, and direct access to the back patio. The second bedroom also offers new flooring and its own walk-in closet, making it perfect for guests or additional living space. With its inviting design and unbeatable location, this condo is a must-see—schedule your private showing today!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,589
Status:
Active
MLS#:
O6392218
Type:
Single Family
Subdivision:
Meadows At Hawks Crest
Lot size:
0.11 Acres
Year built:
2020
A broker reciprocity listing Courtesy: BECK REALTY LLC 407-256-6369
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ADDITIONAL INFORMATION

Taylor Morrison, Anastasia Model, 4 bdrm 3.5 baths on premium lot overlooking pond in the Meadows at Hawk's Crest. Large, spacious open floor plan with 20'+ ceilings, plantation shutters and builtins. Gourmet kitchen with pantry opens to dining area overlooking the great room. Master suite downstairs, laundry room, and half bath. Upstairs 3 bedrooms and 2 baths including an additional primary suite and loft area. Exterior features paver drive, tile roof., screen patio overlooking pond with fountain Community features: Fitness Center, pool, playground, dock, beautiful clubhouse. Short drive to Park Maitland School, Kelly's and Foxtail at community entrance; close to Shopping and Restaurants, and a short drive to Park Avenue and easy access to major roads to airport, attractions and UCF.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,750
Status:
Active
MLS#:
O6384436
Type:
Single Family
Subdivision:
Brookshire Heights
Lot size:
0.21 Acres
Year built:
1958
A broker reciprocity listing Courtesy: DTB FLORIDA REALTY, INC. 786-543-8296
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ADDITIONAL INFORMATION

Completely renovated and move-in ready! This beautifully updated home has been fully remodeled with attention to detail and quality finishes throughout. Recent upgrades include brand-new flooring, modern appliances, fresh interior and exterior paint, and a new A/C system, offering comfort and peace of mind for years to come. The home is in excellent condition. Truly feels like new construction without the new construction price. Perfect for first-time homebuyers looking for a turnkey property or investors seeking a strong rental opportunity in a desirable location. Conveniently located near shopping, dining, major roadways, and top-rated schools. Don’t miss this opportunity to own a fully updated home in a fantastic area!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,003
Status:
Active
MLS#:
O6392099
Type:
Condo
Subdivision:
Golfside Villas Condo
Lot size:
0.03 Acres
Year built:
1969
A broker reciprocity listing Courtesy: SHAWFIELD REALTY GROUP 407-963-7749
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ADDITIONAL INFORMATION

Beautifully updated condo in a prime Winter Park location! This move-in ready unit features a beautifully renovated kitchen, updated bathrooms, and tile flooring throughout, offering a modern and low-maintenance living space. Ideally situated on South Semoran Blvd, you’ll love the convenience of being just minutes to Baldwin Park, Full Sail University, UCF, and Downtown Winter Park, with easy access to shopping, dining, and major roadways. One of the few units in the community featuring a screened patio AND an in-unit washer and dryer, providing added convenience and everyday ease. Low HOA fees make this an excellent opportunity for both homeowners and investors alike. Whether you're looking for a primary residence or an income-producing property, this condo stands out with its upgrades, location, and unique features. NEW ROOF April 2026! Call today to schedule your private showing.

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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 32792 Real Estate

Winter Park is located in Florida. Winter Park, Florida 32792has a population of 29,672. Winter Park 32792 is less family-centric than the surrounding county with 26.31% 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 32792 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 32792 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

    $400,000
    25.3%
    change since last quarter
  • # Active listings

    160
    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
Arbor Ridge K-8 PK - 08 764 13.6 32817
Audubon Park Elementary School PK - 05 1,182 14.8 32814
Brookshire Elementary School PK - 05 632 12.9 32792
Casselberry Elementary School PK - 05 724 13.2 32707
Eastbrook Elementary School PK - 05 809 14.2 32792
Killarney Elementary School KG - 05 444 14.8 32789
Lakemont Elementary School KG - 05 656 14.6 32792
Orange County Preparatory Academy Charter KG - 08 325 13.5 32817
Red Bug Elementary School PK - 05 827 14.3 32707
Riverdale Elementary School PK - 05 674 15 32817
Sterling Park Elementary School PK - 05 817 14.6 32707

Middle Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Einstein Montessori Academy Charter 03 - 08 40 10 32817
Glenridge Middle School 06 - 08 1,415 18.4 32814
South Seminole Middle School 06 - 08 1,228 15.5 32707
Union Park Middle School 06 - 08 873 16.8 32817

High Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Lake Howell High School 09 - 12 2,229 19.1 32792
University High School 09 - 12 3,111 22.1 32817
Winter Park High School 09 - 12 3,069 18.7 32792

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
Winter Park Tech AE - AE 0 32789

Demographics near Winter Park, FL 32792

Zip Code City
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