Winter Park FL Real Estate & Homes for Sale

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Beds:
1
Baths:
1.00
Sq.Ft.:
645
Status:
Active
MLS#:
V4946519
Type:
Condo
Subdivision:
Lakeside Manor Apts Condo
Lot size:
0.1 Acres
Year built:
1969
A broker reciprocity listing Courtesy: LPT REALTY LLC (DB) 877-366-2213
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ADDITIONAL INFORMATION

Welcome to lakeside living! This cozy one-bedroom, one-bathroom condo offers a blend of amenities and convenience. This perfectly located condominium has low HOA FEES and has no assessment fees! Enjoy your days fishing, boating, or hanging out by the pool overlooking gorgeous Lake Killarney, a 240 acre spring-fed lake! Cherish living on the shores of Lake Killarney, complete with coveted dock access and a refreshing pool. Located in the heart of Winter Park, one of the most sought-after zip codes in the Orlando metro area. Residents in the desirable Lakeside Manor community enjoy access to the boat slips, the clubhouse, the lakefront pool and the beautifully maintained landscaped courtyard. Bring your ideas and make this your own. HOA fees includes ground keeping, exterior and roof maintenance. Water is also included with a low monthly HOA fee of $240 a month. HVAC 2021 , Roof 2016, Conveniently located near I-4 for quick access to Orlando. Situated near Winter Park Village, College park and Baldwin Park. Appreciate the nearby hospitals, shopping, dining, museums, parks, botanical gardens and entertainment of Winter Park. Savor your lakeside retreat with low fees and low maintenance. All information deemed reliable but not guaranteed and should be independently verified. If qualified with preferred lender, a $1500 credit will be offered.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,526
Status:
Active
MLS#:
S5140952
Type:
Single Family
Subdivision:
Winter Park Estates
Lot size:
0.25 Acres
Year built:
1961
A broker reciprocity listing Courtesy: MY REALTY GROUP, LLC. 786-847-7421
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ADDITIONAL INFORMATION

Experience luxury living in this stunning, remodeled single-family home located in the heart of Winter Park. This spectacular residence features four spacious bedrooms and three modern bathrooms, boasting sleek laminate flooring throughout. The chef-inspired kitchen comes fully equipped with premium stainless steel appliances, while the massive backyard and sparkling pool provide an ideal setting for family gatherings and outdoor entertainment. Nestled in a prime location, this property provides the perfect blend of suburban tranquility and urban convenience. Residents enjoy proximity to schools and sit just minutes from the iconic Park Avenue shopping district. Whether commuting via the 436 or visiting local favorites like the Winter Park Farmer’s Market, everything you need remains right at your doorstep—the ultimate choice for the best of Central Florida living

Beds:
3
Baths:
2.00
Sq.Ft.:
1,624
Status:
Active
MLS#:
O6370371
Type:
Single Family
Subdivision:
Garden Lake Estates Unit 3
Lot size:
0.27 Acres
Year built:
1983
A broker reciprocity listing Courtesy: FLORIDA PRESTIGIOUS HOMES INC 754-246-2070
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedroom, 2-bath home with a screened-in pool, ideally located in the heart of Winter Park. Step inside to a fresh, move-in-ready feel with new flooring throughout, new light fixtures, new windows, and new doors—all thoughtfully selected to give the home a clean, modern look. The open, inviting layout is perfect for everyday living and entertaining, and the screened pool area creates a private Florida retreat for relaxing weekends, family gatherings, or evening swims—without the bugs. Conveniently close to Winter Park’s shopping, dining, parks, and local favorites, this home offers the best of Central Florida living in a prime location. More photos coming soon—don’t miss your chance to see this one!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,470
Status:
Active
MLS#:
O6369653
Type:
Single Family
Subdivision:
Windsong-knowles Place
Lot size:
0.26 Acres
Year built:
2014
A broker reciprocity listing Courtesy: SELECTIVE REALTY GROUP LLC 407-627-1727
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ADDITIONAL INFORMATION

Welcome home to the prestigious community of Windsong in Winter Park. Upon entering this Toll Brothers-built home, you will notice no detail has been spared. Soaring ceilings greet you as you enter the foyer with elegant lighting. This 4-bedroom, 3.5-bath home is loaded with upgrades. The office features beautiful wood and detailed, custom bookshelves, complete with a double-door entry for added privacy. The formal dining room features a pass-through to the Butler's Pantry, which leads into a chef's oasis—Wolf stainless steel appliances for the serious chef, and solid surface countertops. The gourmet kitchen opens up to the family room. This home is a Great floor plan for entertaining friends and family. Eat in nook is located off the kitchen for dinners together. The primary suite is located on the first floor with a spa-like ensuite. Double vanity, extra-large shower, large bathtub for when a relaxing bath is just what you need after a long day. Upstairs, you will find a bonus room, as well as the remaining bedrooms. off the bonus room is a bedroom and a full bathroom, great for guests. The other two bedrooms and bathroom are located on the opposite side of the upstairs to create a split floor plan. Large backyard for enjoying the Florida weather. New EV charger in garage, new A/C unit. Home includes surround sound. This home features numerous upgrades, too many to list. Windsong community offers a resort-style pool with lake views, a playground, lake for fishing. Close to restaurants, schools, and shopping.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,197
Status:
Active
MLS#:
O6369571
Type:
Single Family
Subdivision:
Pinewood Sub
Lot size:
0.19 Acres
Year built:
1947
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY AT THE PARKS 407-629-4420
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ADDITIONAL INFORMATION

Income-producing home with a detached in-law apartment in a prime central Orlando location — ideal for a house hack, long-term rental, or short-term rental (Airbnb allowed). The main house is a two-bedroom, one-bath residence, while the in-law apartment is a completely detached one-bedroom, one-bath unit with separate entrances and separate mailboxes, offering excellent privacy and flexibility. The in-law apartment is currently rented for $1,350/month on a month-to-month lease, providing immediate income and flexibility. The main house was previously rented for $1,850/month, demonstrating strong and proven rental history. Live in one unit and rent the other, or rent both for attractive cash flow. The main home is well maintained with neutral finishes, updated flooring, modern lighting, and a functional layout filled with natural light. A spacious deck and outdoor area provide excellent separation and privacy between the main house and the in-law unit. Major updates include a roof approximately 11 years old, HVAC approximately 6 years old, copper plumbing, and a septic system recently pumped and in great condition. A 4-point inspection is available upon request. Conveniently located minutes from Winter Park, College Park, Downtown Orlando, major hospitals, dining, I-4, International Drive, and Orlando International Airport. A rare opportunity offering location, flexibility, and multiple income strategies.

Open House:

Sunday, 2/1 12:00-3:00PM

More Open House Info >

Beds:
3
Baths:
2.00
Sq.Ft.:
1,178
Status:
Active
MLS#:
O6368415
Type:
Townhouse
Subdivision:
Fernbrook Trails
Lot size:
0.09 Acres
Year built:
1986
A broker reciprocity listing Courtesy: KELLER WILLIAMS ADVANTAGE III 407-207-0825
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ADDITIONAL INFORMATION

One or more photo(s) has been virtually staged. Move-in ready 3-bedroom, 2-bath townhome in desirable Winter Park featuring recent exterior paint and a clean, modern presentation throughout. BRAND NEW water heater, A/C replaced in 2021, and NEW ROOF (2026). The spacious family room sits beneath dramatic two-story vaulted ceilings highlighted by tongue-and-groove ceiling planks, creating an open and architectural focal point. The functional layout includes a large bedroom and full bath on the main level—ideal for guests, a home office, or multi-generational living. Upstairs, two additional bedrooms share a Jack-and-Jill style bath, offering privacy and efficiency. The kitchen opens to the dining and living areas, making the space well-suited for everyday living and entertaining. Sliding doors lead to a screened-in patio and a private, white PVC-fenced yard—low maintenance and perfect for relaxing or pets. Additional features include wood-look flooring in main living areas, neutral finishes, and abundant natural light. Conveniently located near Winter Park shopping, dining, parks, and major roadways. A strong option for buyers seeking space, location, and low-maintenance townhome living.

Open House:

Saturday, 1/31 1:00-4:00PM

More Open House Info >

Beds:
4
Baths:
4.00
Sq.Ft.:
2,540
Status:
Active
MLS#:
O6369267
Type:
Single Family
Subdivision:
Temple Estates
Lot size:
0.19 Acres
Year built:
1952
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

In the heart of Winter Park, this extensively renovated modern farmhouse offers exceptional value for the location. A circular drive and inviting front porch welcome you into light-filled living spaces enhanced by all-new energy-efficient windows, custom millwork and designer finishes throughout. The functional layout includes a first-floor guest suite, additional well-appointed bedrooms and updated baths. The kitchen is updated, featuring custom cabinetry, stone countertops and stainless appliances. The family room flows to a covered lanai and summer kitchen, overlooking a paver deck, pool, fire pit and putting green, ideal for year-round entertaining. The fully fenced backyard offers privacy and access to a detached garage with additional storage. Upstairs, the primary suite features a private balcony, a sitting area, a walk-in closet, and a spa-inspired bath with a freestanding tub and an oversized shower. An additional upstairs fourth bedroom en suite, used as a gym, offers flexibility for a home office or nursery. Renovated with quality and intention, including updated systems and recent roofs. Ideally, across from Phelps Park and just a few blocks from Interlachen Country Club and Winter Park Racquet Club.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,117
Status:
Active
MLS#:
O6369034
Type:
Townhouse
Subdivision:
Hidden Oaks Condo Ph 10
Year built:
1984
A broker reciprocity listing Courtesy: SPRINGHILL PROPERTIES LLC 646-236-0299
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ADDITIONAL INFORMATION

Excellent opportunity to acquire a 3-bedroom, 2-bath first-floor end-unit condo offering approximately 1,117 sq ft in a well-established community. The unit features a functional layout and a highly desirable location near UCF, Full Sail University, Valencia College, and major shopping and dining. Priced to sell, this property is ideal for investors seeking a light-to-moderate rehab with strong rental or resale potential, or for a first-time buyer looking to add value. Schedule a showing today and capitalize on this opportunity.

Beds:
1
Baths:
1.00
Sq.Ft.:
645
Status:
Active
MLS#:
O6368580
Type:
Condo
Subdivision:
Lakeside Manor Apts Condo
Lot size:
0.04 Acres
Year built:
1969
A broker reciprocity listing Courtesy: HOMESMART 407-476-0451
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ADDITIONAL INFORMATION

Welcome to your next chapter of lakeside living! This charming one-bedroom, one-bathroom condo offers a perfect blend of tranquility and convenience in the heart of Winter Park. Step inside to discover a thoughtfully designed space where comfort meets style. The open-concept living area welcomes you with beautiful engineered wood floors, creating a seamless flow between the living room and kitchen. Natural light streams through the windows, highlighting the warm and inviting atmosphere throughout.Your private bedroom retreat features a generously sized closet, making storage a breeze. The well-appointed bathroom complements the living space perfectly. What truly sets this home apart is its privileged location near Lake Killarney, a stunning 239-acre spring-fed lake that serves as your backyard oasis. As a resident, you'll enjoy exclusive access to on-site boat slips, a launch, and an updated dock. Take a peaceful stroll along the 60-foot walkway leading to a covered gazebo - the perfect spot for your morning coffee or evening sunset views. The community amenities include a lakefront pool and clubhouse, while the meticulously maintained grounds showcase lush Florida landscaping. Located just moments from Winter Park Village, you'll find fantastic shopping, dining, and entertainment options right around the corner. Experience the joy of maintenance-free living while being connected to nature and urban conveniences. This hidden gem won't last long!

Beds:
1
Baths:
1.00
Sq.Ft.:
482
Status:
Active
MLS#:
O6368912
Type:
Condo
Subdivision:
Phillips Circle Rep
Lot size:
2.77 Acres
Year built:
1960
A broker reciprocity listing Courtesy: TURN-KEY MOVES REALTY 407-796-2221
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ADDITIONAL INFORMATION

Welcome to an exceptional opportunity to own a beautifully maintained, move-in ready third-floor, water-view, corner unit studio residence in one of Winter Park’s most coveted locations—directly adjacent to Lake Osceola and just moments from iconic Park Avenue. This rare downtown setting places you within effortless reach of the Winter Park Farmers’ Market, acclaimed dining, boutique shopping, cultural venues, and a picturesque network of lakes and parks. The residence features a bright and open floor plan where the kitchen, dining, and living spaces flow seamlessly, creating an inviting atmosphere ideal for both everyday living and entertaining. Upon entry, you are welcomed by multiple storage closets and a discreet hallway that provides additional storage and convenient access to the full bathroom—an uncommon luxury for a studio-style layout. Sliding glass doors lead to a generously sized, private covered and enclosed balcony overlooking the tranquil interior courtyard, with peaceful views of the community pool and Lake Osceola beyond. This serene outdoor retreat is the perfect setting for morning coffee, evening relaxation, or quiet reflection amid lush surroundings. Residents enjoy a truly low-maintenance lifestyle, with electric, gas, water, sewer, and trash all included in the condominium fee. Building amenities include elevator access to the third floor, on-site management, a community laundry facility, and beautifully appointed common areas. The property also features expansive outdoor patios overlooking Lake Osceola, a resident club room, and immediate access to the community pool. Located within Whispering Waters, a highly desirable 55+ community, this residence is ideally suited as a primary home, seasonal retreat, or elegant in-law suite—offering timeless Winter Park living with unmatched convenience and charm.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,085
Status:
Active
MLS#:
S5140472
Type:
Condo
Subdivision:
Winter Park Woods Condo
Lot size:
0.07 Acres
Year built:
1974
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

Excellent opportunity to own this second-floor, 2-bedroom, 1/1-bath condo in a Conveniently location close to healthy centers, excellent schools, restaurants and shopping with easy access to Costco, Walmart, and various dining options. Only 4 miles from Winter Park SunRail Train Station and 20 minutes from Orlando International Airport. This unit offers a cozy living/dining area with sliding doors leading to a private balcony that includes extra storage.

Open House:

Sunday, 2/1 1:00-3:00PM

More Open House Info >

Beds:
2
Baths:
1.00
Sq.Ft.:
808
Status:
Active
MLS#:
O6368234
Type:
Condo
Subdivision:
Aragon Condo
Lot size:
0.13 Acres
Year built:
1984
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor condo in the heart of charming Winter Park, FL 32789! Meticulously updated since 2023, this home blends modern luxury with effortless comfort and is truly move-in ready. As you step inside, you’ll be greeted by elegant porcelain tile flooring throughout—offering both durability and a look that’s easy to maintain. The heart of the home, the kitchen, has been completely reimagined with sleek granite countertops, fresh cabinetry, and contemporary finishes that make cooking and entertaining a joy. The bathroom has also received a full renovation, featuring granite countertops and updated fixtures that enhance both style and function. With thoughtful design at every turn, this condo feels fresh, bright, and uniquely yours. Situated on the second floor for added privacy and natural light, this unit provides a peaceful retreat while still being close to all that Winter Park has to offer. Enjoy being minutes from Park Avenue, with its array of boutique shopping, acclaimed restaurants, art galleries, and outdoor markets. Explore scenic parks, lakeside boat tours, cultural attractions, and community events that make Winter Park one of Central Florida’s most desirable places to live. Whether you’re searching for your next home or an exceptional investment opportunity, 851 Miles Ave #13 showcases stylish updates, quality finishes, and a location you’ll love. Don’t miss your chance — schedule a showing today!

Beds:
1
Baths:
1.00
Sq.Ft.:
673
Status:
Active
MLS#:
O6367841
Type:
Condo
Subdivision:
Park Aire Condo
Lot size:
0.56 Acres
Year built:
1956
A broker reciprocity listing Courtesy: PARK TOWN REAL ESTATE LLC 561-801-9199
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ADDITIONAL INFORMATION

Location, Location, Location! Charming first floor 1 bedroom, 1 bath condo ideally located on North Park Avenue in the retro-chic Park Aire complex. Beautifully overhauled in 2018 with quartz counters, new cabinetry, new appliances, custom mosaic kitchen detail, new flooring, new lighting, updated electrical, with picturesque views of the Winter Park Golf Course and Casa Feliz. Enjoy a large walk-in closet, one assigned carport space, and a private storage room. The community offers a sparkling saltwater pool, two third-floor outdoor patios, laundry facility, elevator, and a guest-quarters efficiency available to owners for a nominal fee. Just steps from Park Avenue shopping and dining, cafes, churches, Winter Park Golf Club, Rollins College and more. No pets.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,916
Status:
Active
MLS#:
S5140580
Type:
Single Family
Subdivision:
Lost Creek
Lot size:
0.3 Acres
Year built:
1994
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

******* Motivated Seller offering $10k credit to Buyer with full price offer. Home is priced under market value to sell!*** This beautifully updated Winter Park home with 3BR+Office/ 2 Bathrooms, features light-filled rooms and thoughtful upgrades to create the perfect blend of comfort and style. The oversized living room showcases brand-new LVP flooring, soaring volume ceilings, a ceiling fan and dramatic tall glass doors with windows above, that flood the space with natural light and easy access to the screened lanai. The lanai is ideal for relaxing or entertaining, complete with a ceiling fan, two skylights and is pre-wired for a tv. The kitchen features stainless steel appliances, lots of cabinets, a closet pantry, and generous granite countertop space. Next to the Kitchen is a sunny eat-in area accented by double glass doors that lead to the slate tile patio and side yard. On the other side of the kitchen and living room is a versatile office/flex space perfect for working from home, a dining room or playroom. The primary suite is a true cozy retreat with brand-new carpet, a spacious walk-in closet, and an ensuite bathroom featuring a soaking tub, separate walk-in tiled shower, and a modern floating dual-sink vanity. Additional highlights include elegant French doors at the Home's front entry with overhead sunlight windows, an extra-long driveway, a two-car garage, and an oversized fenced yard with plenty of room to add a pool. Small neighborhood with low HOA $22/month. All of this in a desirable Winter Park location—this home is move-in ready and designed for easy Florida living.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,916
Status:
Active
MLS#:
O6367773
Type:
Single Family
Subdivision:
Winter Park Village
Lot size:
0.18 Acres
Year built:
2026
A broker reciprocity listing Courtesy: ONE LUXURY INTERNATIONAL LLC 407-312-8003
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ADDITIONAL INFORMATION

Under Construction. An architectural statement in the heart of Winter Park, this remarkable residence designed by renowned architect Gary Hancock is a masterclass in craftsmanship, architecture, and timeless elegance. From the moment you arrive, the home commands attention with a breathtaking façade defined by graceful archways and refined architectural symmetry. Every exterior line and material selection has been intentionally chosen to create a presence that feels both bold and enduring, setting this residence apart as something truly exceptional. Inside, the home unfolds into a light-filled interior where design and livability coexist seamlessly. Ten-foot ceilings, level 5 drywall, and an abundance of expansive windows allow natural light to pour into every space, illuminating the impeccable finishes and creating an airy, sophisticated atmosphere throughout. Upgraded designer light fixtures add warmth and character, while the open-concept layout is anchored by a stunning living area centered around a refined fireplace, offering a natural gathering space that feels both intimate and grand. Flowing effortlessly from the living room, the dining area opens through elegant doors to the outdoor entertaining spaces, beautifully blending indoor and outdoor living. At the heart of the home, the chef’s kitchen is as visually striking as it is thoughtfully designed. Custom cabinetry with integrated LED under-lighting, sleek quartz countertops, a paneled refrigerator, and a premium induction range are complemented by a full suite of high-end stainless steel appliances, reflecting the builder’s uncompromising commitment to quality, performance, and clean modern design. The primary suite is a private retreat, highlighted by a spa-inspired bath with a freestanding soaking tub, an expansive walk-in shower, and a beautifully designed walk-in closet with direct access to the laundry room for effortless everyday living. Each secondary bedroom continues the theme of elevated design, offering generous proportions, abundant natural light, and elegantly appointed en-suite baths that ensure comfort and privacy for family and guests alike. Outdoors, the home reveals another level of thoughtful craftsmanship. A covered patio with a fully equipped summer kitchen overlooks a sparkling pool and expansive backyard, creating a setting equally suited for quiet evenings or lively gatherings. What truly defines this residence is the extraordinary level of craftsmanship throughout. No detail has been overlooked, no finish treated as an afterthought, and no design decision made without intention. This is a home that feels as impressive in its execution as it does in its presence.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,854
Status:
Active
MLS#:
O6367536
Type:
Single Family
Subdivision:
Brookshire Heights
Lot size:
0.22 Acres
Year built:
1962
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

Welcome to 2350 Cady Way! Ideally located within walking distance to Brookshire Elementary and directly across from Showalter Field, this home offers easy access to the Cady Way Trail, Baldwin Park’s downtown area and dog park, Winter Park AdventHealth Hospital, and the Crosby Wellness Center, and is just a 5 to 10 minute drive to Park Avenue’s shopping, dining, and entertainment. Step inside to a bright and inviting living room with sliding doors to the backyard and a shared fireplace with the adjacent family room. The family room offers built-in shelving, cabinet storage, and sliding doors leading to a screened-in porch. The kitchen connects to a spacious laundry room with built-in cabinetry and floating shelves, with direct access to an oversized two-car garage featuring built-in shelving and storage cabinets. On the opposite side of the laundry room is a functional mudroom with an additional door to the backyard. The primary bedroom features a walk-in closet with excellent natural light. The primary bathroom includes a walk-in shower, granite countertops, and built-in storage. The secondary bathroom also offers granite countertops, built-in storage, and a bathtub. Throughout the home you will find abundant storage, exceptional natural light, and new remote-controlled ceiling fans. Major updates include a new HVAC system, full plumbing re-pipe, updated electrical panel, exterior flood lighting, new flooring, new fence, new dishwasher, and chimney repairs completed in 2021. Additional improvements include new garage doors and openers in 2024, and in 2025 a new refrigerator, new roof with a 10-year warranty, fresh interior paint, a landscape refresh, and brand new windows.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,111
Status:
Active
MLS#:
O6364508
Type:
Single Family
Subdivision:
Lake Forest Park
Lot size:
0.19 Acres
Year built:
2026
A broker reciprocity listing Courtesy: COMPASS FLORIDA LLC 407-203-9441
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ADDITIONAL INFORMATION

Under Construction. Signature new construction currently under way, thoughtfully designed for modern living with a refined balance of warmth, scale, and functionality. This two-story residence close to 3,200 square feet under air with a 4-bedroom, 4-full-bath layout plus a dedicated office and second-floor media room, delivering flexibility without compromise. The main level is anchored by a private primary suite featuring a generous walk-in closet, alongside a dedicated office with walk-in closet that can easily function as a guest bedroom. A main-level full pool bath, accessible directly from the lanai, enhances everyday livability and seamless indoor-outdoor flow. At the heart of the home, the kitchen is both elevated and inviting—appointed with custom oak cabinetry, a 48-inch gas range, walk-in pantry, and oak flooring. Wood-beam ceilings and a fireplace with custom built-ins frame the living and dining areas, creating a natural, cohesive flow ideal for both daily living and entertaining. Upstairs, additional bedrooms are thoughtfully arranged along with a spacious open media room, providing a flexible retreat for relaxation or gathering while maintaining privacy from the main living spaces. The backyard is designed as an extension of the home, featuring a resort-style pool and built-in BBQ area—perfect for year-round Florida living. Two-car garage. Architectural plans and floorplans available. Designed with care. Built with purpose. Inquire today

Beds:
5
Baths:
7.00
Sq.Ft.:
5,006
Status:
Active
MLS#:
A11930648
Type:
Single Family
Subdivision:
Sicilian Shores
Year built:
2018
Courtesy: RDS Realty, LLC Yuri Saenz 786-303-6970
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ADDITIONAL INFORMATION

Enjoy the best of what luxurious lakefront living has to offer in this stylish, modern, smart new home in Winter Park's exclusive Via's neighbourhood. This spectacular, 5-bedroom, 6.5-bath, multi-level masterpiece combines innovative contemporary design with brilliant architectural artistry, blending the latest in modern living with superior craftsmanship. Tucked away on Lake Maitland adjacent to the Isle of Sicily, this exquisite home features state-of-the-art technology throughout, accented by classic, elegant finishes such as custom Walnut floors, staircase, landing and interior doors, and porcelain tile work. Designed for lakefront living and entertaining inside and out, a large designer chefs kitchen includes custom cabinetry, dual dishwashers, double ovens, warming drawers, a large walk in pantry and wet bar with wine cooler. Step outside to enjoy gorgeous views of the largest lake in Winter Park's chain, and outdoor lanai including a sparkling pool, an outdoor kitchen, a gas fire pit and outdoor shower. The first floor includes a large master suite, 2 additional bedrooms, and a formal dining room. glass-enclosed office, and gas fireplace. The second floor includes a den and two bedrooms with full baths. This modern Smart Home is iPad & Touch Panel integrated, including surround audio, lighting control, video doorbell with off-site answering, garage door control, voice control, retractable phantom lanai and patio screens

Beds:
3
Baths:
2.00
Sq.Ft.:
1,284
Status:
Active
MLS#:
O6368303
Type:
Single Family
Subdivision:
Windward Square Sec 2
Lot size:
0.07 Acres
Year built:
1977
A broker reciprocity listing Courtesy: LUXE HUNTER REAL ESTATE 407-984-4888
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ADDITIONAL INFORMATION

NEW ROOF, NEW HVAC installed before closing along with NEW WATER HEATER and NEW BUILT IN MICROWAVE! Welcome to 2634 Exuma Way, a well-maintained 3-bedroom, 2-bathroom home located in the heart of Winter Park, where comfort meets convenience. This property stands out as the only home in the area featuring a wrought iron privacy fence, offering a unique sense of character and added seclusion. Enjoy morning coffee or evening gatherings on the oversized front patio, while the backyard space provides room to relax, garden, or entertain. Inside, the kitchen features granite countertops and flows seamlessly into the living areas, creating a warm and functional layout. Additional highlights include: Oversized front patio Granite countertops Private backyard space Carport included Ring doorbell included Two separate storage closets for added convenience Located just minutes from Park Avenue, dining, boutique shopping, parks, cultural attractions, and top-rated schools, this home offers the best of Winter Park living—a charming neighborhood feel with easy access to everything Central Florida has to show you. Community is also amenity rich featuring a pool, clubhouse, tennis courts and a small golf area. Perfect for those seeking privacy, functionality, and a prime location. Schedule your showing today and experience the lifestyle this Winter Park gem provides.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,885
Status:
Active
MLS#:
O6366793
Type:
Single Family
Subdivision:
Casa Aloma
Lot size:
0.24 Acres
Year built:
1969
A broker reciprocity listing Courtesy: KELLY PRICE & COMPANY LLC 407-645-4321
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ADDITIONAL INFORMATION

Welcome to 2665 Tierra Circle, a captivating Mediterranean-inspired residence nestled in the desirable Casa Aloma neighborhood of Winter Park. This thoughtfully maintained 4-bedroom, 2-bath home spans 1,885 square feet and has been lovingly cared for by a single owner for the past 23 years, evident in every detail throughout. Step inside to discover a flowing floor plan featuring distinct living, dining, and family rooms, all bathed in abundant natural light, particularly during the afternoon hours. The home's signature feature is its numerous French doors that seamlessly connect the interior spaces to enchanting garden islander styled courtyard areas, creating an indoor-outdoor living experience reminiscent of classic Mediterranean architecture. Elegant tile flooring flows throughout the home, complemented by crown molding that adds a refined touch to each room. The primary bedroom serves as a private retreat with its en suite bathroom featuring a walk-in shower, while three additional guest bedrooms share a well-appointed hall bath. Notably, the dividing wall between the third and fourth bedrooms has been removed to create a generous suite, offering flexibility to reinstate a fourth private bedroom with simple drywall installation if desired. The true showpiece of this property is the mature landscaping and garden spaces that surround the home, offering multiple courtyard areas perfect for entertaining or peaceful relaxation. The private pool provides a refreshing escape, while block walls throughout ensure complete privacy on the spacious 0.24-acre corner lot. Practical updates include a 2021 HVAC system and 2019 roof, natural gas utilities, and a large laundry and storage room. The two-car garage completes this exceptional offering, presenting a rare opportunity to own a meticulously maintained retreat in one of Winter Park's most sought-after neighborhoods.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,602
Status:
Active
MLS#:
R11147259
Type:
Single Family
Subdivision:
VILLAGE GREEN
Lot size:
0.29 Acres
Year built:
1972
Courtesy: Compass Florida, LLC 954-477-7332
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ADDITIONAL INFORMATION

Welcome to this inviting single-family home at 7641 Village Green Dr in desirable Winter Park, FL. This well-maintained residence features 3 bedrooms and 3 full bathrooms across approximately 1,958 square feet of living space — perfect for comfortable daily living and entertaining. Set on a generous lot of nearly 0.30 acres, the property includes a private fenced-in backyard with an in-ground pool, offering your own tranquil oasis for relaxing, play, and summer gatherings. Inside, the home offers a naturally welcoming layout with a neutral palette throughout and flexible living spaces that allow for personalization. The primary suite boasts a walk-in closet. Located close to a variety of shops, dining, and everyday conveniences.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,782
Status:
Active
MLS#:
O6367023
Type:
Townhouse
Subdivision:
Grayson Square
Lot size:
0.05 Acres
Year built:
2023
A broker reciprocity listing Courtesy: LPT REALTY, LLC 877-366-2213
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ADDITIONAL INFORMATION

Discover comfortable Winter Park living in this bright and stylish 3-bedroom, 2.5-bathroom corner-unit townhome located in the gated Grayson Square community. Abundant natural light fills the open-concept living area, which flows seamlessly to a covered lanai that’s perfect for relaxing mornings or quiet evenings. The modern kitchen includes stainless steel appliances, quartz countertops, and generous storage, offering both convenience and contemporary appeal. The owner’s suite features a spacious walk-in closet and an elegant ensuite bathroom with a glass-door shower and dual quartz vanities. Additional highlights include a two-car garage with epoxy flooring, and a washer and dryer for added ease. The community offers a peaceful pool with a cabana, along with 1GB high-speed fiber optic internet and 75 streaming cable and music channels. Ideally located just minutes from downtown Winter Park, the home provides easy access to major highways (436, 434, 417), as well as nearby conveniences such as Starbucks, Publix, and Walmart. Top-rated Seminole County Schools and the shopping and dining of Park Avenue are also close by. This thoughtfully designed home blends natural light, modern finishes, and a fantastic location to create a welcoming and refined place to call your own. ¡Hablo español!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,227
Status:
Active
MLS#:
O6364069
Type:
Single Family
Subdivision:
Garden Lake Estates Unit 3
Lot size:
0.43 Acres
Year built:
1983
A broker reciprocity listing Courtesy: KELLER WILLIAMS ADVANTAGE REALTY 407-977-7600
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ADDITIONAL INFORMATION

Tucked peacefully at the top of a cul-de-sac in the sought-after Garden Lake Estates community, this lakefront residence offers a rare blend of serenity, timeless character, and effortless Florida living. From the first approach, the home feels warm and welcoming, mature landscaping frames the paver drive, and a charming front porch sets the tone for the relaxed, inviting style carried throughout. Inside, the home’s thoughtful split-bedroom layout and multiple gathering spaces create a natural flow for both everyday comfort and entertaining. The formal living and dining areas lead seamlessly into the heart of the home, where a cozy wood-burning fireplace anchors the family room. The kitchen lives warm and inviting, with rich wood cabinetry, granite countertops, stainless steel appliances, and thoughtfully designed glass-front display cabinets. A convenient pass-through connects the kitchen to the sunroom, keeping the cook part of the conversation and offering glimpses of the lake. Combined with the adjacent dining areas, this space supports both casual meals and memorable gatherings with ease. Just beyond, a light-filled sunroom becomes a true showcase space, expanded with tongue-and-groove ceilings, skylights, and panoramic views that draw the outdoors in. This room lives beautifully as a lounge, reading retreat, or entertaining extension, opening directly to the home’s outdoor living areas. Designed for connection to nature, the rear of the home opens to a large screened lanai and an extended lakeside deck, capturing wide sparkling views of Garden Lake. Morning sunrises, evening reflections, and gentle breezes set the backdrop for daily living. Step down to the flagstone patio or the beautifully landscaped yard for even closer access to the shoreline, perfect for launching a kayak or savoring the peaceful setting. Every detail has been tastefully appointed, from updated baths to well-maintained finishes that reflect pride of ownership. The primary suite enjoys privacy and garden views, while two additional bedrooms create versatility for guests, office space, or multigenerational living. This neighborhood is a quiet, established enclave offering a uniquely calm, tucked-away feel while remaining close to everything. A short drive brings you to Winter Park’s signature lifestyle, shopping on Park Avenue, an exceptional dining scene, medical centers including AdventHealth Winter Park, and convenient access to major roadways for commuting or travel. Nearby higher education anchors such as Rollins College and Full Sail University, along with major regional employers, add to the area’s vitality. Schedule your private tour today!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,085
Status:
Active
MLS#:
A11924851
Type:
Townhouse
Subdivision:
Four Seasons Condo
Year built:
1974
Courtesy: Kleros Realty, LLC. 305-244-9963
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ADDITIONAL INFORMATION

Experience the best value in Winter Park. Beautifully maintained corner-unit townhome in the desirable Four Seasons community, offering a perfect blend of comfort, privacy and style. This bright and inviting residence features modern laminated floors, new carpet in the bedroom areas, granite kitchen countertops, updated lighting, and recently painted interiors. Enjoy the convenience of a private front entrance and a second entrance from the spacious patio- ideal for added flexibility and seamless indoor=outdoor living. Abundant natural light enhances the the open layout and inviting living areas. Four Seasons community delivers top tear amenities: 3 swimming pools, tennis courts, a fitness center, clubhouse, laundry facilities and beautifully maintained green spaces . Ideally located near Full Sail University , shopping, dining, and major roadways. A turnkey home you won't want to miss.

Beds:
6
Baths:
9.00
Sq.Ft.:
12,190
Status:
Active
MLS#:
O6367595
Type:
Single Family
Subdivision:
---
Lot size:
2.18 Acres
Year built:
2002
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor court framed by lush, manicured grounds spanning over two acres with impressive sunset views across Lake Maitland. Every element of the estate is thoughtfully connected by covered walkways, including five garages (three-car and two-car) and two motor courts, a detached office or seventh bedroom suite, and a lakeside pool cabana, creating a seamless blend of function, elegance and architectural harmony in this one-owner Lake Maitland residence. A dramatic arrival sets the tone as a flowing water feature guides guests along the walkway to the front entry. Inside, the grand foyer opens to a breathtaking gathering room, anchored by soaring two-story windows that frame panoramic lake views, the expansive terrace and terraced outdoor space. A dedicated space for a grand piano enhances the home’s capacity for elegant entertainment and memorable gatherings. The spacious kitchen overlooks the family room and is positioned alongside a dedicated bar, breakfast room and dining room. The family room, warmed by a gas fireplace, is filled with natural light and opens through a wall of French doors to the open terrace, blurring the line between indoor and outdoor living. The first-floor primary suite is a serene retreat with French doors to a covered outdoor space, a fireside sitting area wrapped in custom bookshelves, and a spa-inspired bath featuring a large glass shower, soaking tub, expansive walk-in closet, and a versatile flex room ideal for yoga, massage or expanded wardrobe space. A full guest suite with en-suite bath and walk-in closet is also on the main level. Upstairs, a grand mezzanine overlooks the gathering room, offering a dramatic extension of the living areas. French doors open to a front balcony, while the west wing features two bedrooms with a shared private living room and full bath. The east wing hosts two additional bedroom suites, each with walk-in closets and en-suite baths, one enhanced by a private sitting area and access to a spacious rear balcony. Off the kitchen, a wrought-iron gate leads to the basement level, where a refrigerated wine cellar, theater room, and generous storage space await. Outdoors, the stunning terrace showcases a heated spa, sparkling lakeside pool, expansive gas fire pit and an extraordinary 700-square-foot pool cabana that offers a wraparound screened porch with summer kitchen, a full bar, gaming area and full bath, ideal for lakeside entertaining. Elevated above the water for commanding views and shielded from the main road for complete privacy, this remarkable estate is a masterpiece, designed for multi-generational living and destined to create lasting memories for generations to come.

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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


Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of {{last updated}}. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Copyright 2026, My Florida Regional MLS DBA Stellar MLS.

Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Use of search facilities of data on the site, other than a consumer looking to purchase real estate, is prohibited. © 2026 MIAMI Association of REALTORS®, all rights reserved.


Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc.




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

    $500,000
    25.3%
    change since last quarter
  • # Active listings

    299
    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