Winter Park, FL Homes For Sale | Real Living Real Estate Solutions | Real Living Real Estate Solutions

Winter Park FL Real Estate & Homes for Sale

333 Properties Found

The median home value in Winter Park, FL is $478,950 . This is higher than the county median home value of $318,000. The national median home value is $308,980. The average price of homes sold in Winter Park, FL is $478,950. Approximately 56% of Winter Park homes are owned, compared to 33% rented, while 11% are vacant. Winter Park real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Winter Park real estate agent to arrange a tour today!
Learn more about Winter Park Real Estate.


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Beds:
3
Baths:
2.00
Sq.Ft.:
1,253
Status:
NEW LISTING
MLS#:
O6292176
Type:
Single Family
Subdivision:
EASTBROOK SUB UNIT 07
Lot size:
0.25 Acres
Year built:
1965
A broker reciprocity listing Courtesy: INVESTOR'S REAL ESTATE LLC, 407-688-4355
View additional info

Dreams Do Come True! Charming Winter Park Retreat - Fully Renovated & Move-In Ready! Welcome to this stunning 3-bedroom, 2-bathroom gem in the highly sought-after Eastbrook community of Winter Park! Offering almost 1,300 sqft of spacious living, this home has been beautifully upgraded with modern finishes and stylish details throughout. Incredible curb appeal Featuring a brand-New roof, New fresh interior and exterior paint, and New luxury vinyl plank flooring throughout. The stunning New kitchen boasts quartz countertops, shaker cabinets, a sunken sink, and stainless steel appliances. Additional upgrades include New 5-inch gutters, a paved driveway, and a versatile 1-car garage that can be used for parking or as an extra room. The spacious lot offers privacy with no neighbors on two sides, beautiful backyard views, a fire pit, and an adorable workshop house with full electrical. Incredible entertainers home. Inside, enjoy stylish details like barn doors, shiplap in the master bathroom, ceiling fans, and a screened patio. A newer HVAC system ensures year-round comfort. Located in a prime Winter Park location near top-rated schools, shopping, and dining, this move-in-ready home is a must-see!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,672
Status:
NEW LISTING
MLS#:
O6292204
Type:
Single Family
Subdivision:
PARK MANOR
Lot size:
0.23 Acres
Year built:
1956
A broker reciprocity listing Courtesy: MAINFRAME REAL ESTATE, 407-513-4257
View additional info

Ready to reimagine or build your dream home in beautiful Winter Park? This home, sited on a large .23 acre lot, is ready for your dreams to become reality! A few minutes from top Winter Park schools, the WP YMCA, Winter Park Racquet Club, Interlachen Country Club, shopping, dining and other conveniences and surrounded by beautiful mid-century and luxury homes. This home has 3 bedrooms plus 2 bonus rooms that would be perfect as a large primary bedroom or home gym. The home needs a new roof, so plan accordingly! There are terrazzo floors and real wood floors in the home as well as beautiful multi-pane glass doors separating the living room from the bonus room. You'll love the beautiful street and surrounding neighborhood. Floor plan and survey available. HVAC, electrical, some plumbing and water heater have been more recently updated. This is a rare opportunity to get into Central Florida's most prized community and make a home YOUR OWN!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,522
Status:
NEW LISTING
MLS#:
O6292351
Type:
Single Family
Subdivision:
KENILWORTH SHORES SEC 03
Lot size:
0.22 Acres
Year built:
1956
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY, 407-644-3295
View additional info

This home has three intriguing possibilities, each offering its own unique set of considerations. There may be abuyer who decides to purchase the home to live in it as-is. This buyer envisions making gradual repairs andupgrades over time, personalizing the property while steadily investing in its improvements. There may be aninvestor that plans to convert the property into a rental. This investor possesses the financial capability to carryout necessary repairs and turn the house into an income-generating asset. A more dramatic scenario involvesthe demolition of the existing home, paving the way for new construction that aligns with other recent builds inthe area. This path not only boosts the aesthetic appeal of the surrounding community but also sets abenchmark for future developments. By marketing the property's potential for a tear-down and rebuild, thisscenario attracts buyers interested in long-term investments that promise to uplift the neighborhood.

Open House:

Saturday, 3/22 12:00-2:00PM

Beds:
2
Baths:
2.00
Sq.Ft.:
990
Status:
NEW LISTING
MLS#:
O6290750
Type:
Condo, Townhouse
Subdivision:
HIDDEN OAKS CONDO PH 10
Lot size:
2.13 Acres
Year built:
1984
A broker reciprocity listing Courtesy: REDFIN CORPORATION, 407-708-9747
View additional info

One or more photo(s) has been virtually staged. Welcome to this beautifully updated 2-bedroom, 1.5-bathroom condo located in the desirable Hidden Oaks community in Winter Park, Florida. This townhome-style condo offers a bright, open living area inviting you to relax and unwind. Just off the living room, you'll discover a beautifully modern kitchen featuring elegant quartz countertops, solid wood cabinetry, sleek stainless steel appliances, a stylish backsplash that adds to the elegance, and a stunning farmhouse sink that perfectly complements the space. Adjacent to the kitchen is a cozy dining nook, and a sliding glass door opens to your private outdoor patio, perfect for enjoying the Florida sunshine.The spacious primary bedroom offers an attached bathroom with dual sinks and a convenient shower/tub combo. This home also includes two parking spots located directly in front of the unit, adding convenience to your daily routine. The assessment for this property is being paid before closing, offering peace of mind to the new owner.Hidden Oaks is a well-maintained community that includes access to a refreshing community pool, and its prime location provides easy access to UCF, Full Sail University, and the charming Winter Park area. Plus, with quick access to the 417 and 408 highways, commuting around Orlando has never been easier, bringing the best of the city right to your doorstep. Don't miss your chance to call this fantastic condo your home!

Open House:

Saturday, 3/22 12:00-2:00PM

Beds:
4
Baths:
2.00
Sq.Ft.:
1,998
Status:
NEW LISTING
MLS#:
O6292153
Type:
Single Family, Ranch
Subdivision:
EASTBROOK SUB UNIT 11
Lot size:
0.18 Acres
Year built:
1967
A broker reciprocity listing Courtesy: NEXTHOME NEIGHBORHOOD REALTY, 407-377-7735
View additional info

Prime Winter Park Location - Updated 4-Bedroom Home in Eastbrook with No HOA!Welcome to 3420 Arnel Drive, a beautifully updated 4-bedroom, 2-bath home nestled in the desirable Eastbrook neighborhood of Winter Park"with no HOA! This charming home offers modern updates, spacious living areas, and an unbeatable location just minutes from Park Avenue, top-rated Seminole County schools, and endless shopping, dining, and entertainment.Step inside to find an inviting open floor plan featuring a contemporary kitchen with sleek granite countertops, an oversized island, and stylish modern cabinetry. The family room flows seamlessly to the screened-in covered patio, creating the perfect indoor-outdoor living space. Enjoy easy-maintenance wood-look tile and laminate flooring throughout, plus a spacious fenced backyard, ideal for entertaining or relaxing.Recent upgrades include a newer roof, AC system, water heater, updated electrical panel, and fresh exterior and interior paint"making this home truly move-in ready!Located in a pedestrian-friendly neighborhood, this home is close to Eastbrook Elementary and just a short drive to Park Avenue's boutique shopping, dining, and cultural attractions. With convenient access to major highways, public transportation, and recreational hotspots like Cady Way Trail and Goldenrod Park, this property offers the perfect blend of suburban tranquility and urban convenience.Don't miss this incredible opportunity"schedule your private showing today!

Open House:

Saturday, 3/22 10:00-1:00PM

Beds:
4
Baths:
2.00
Sq.Ft.:
1,598
Status:
NEW LISTING
MLS#:
O6290733
Type:
Single Family
Subdivision:
BRIDGEWATER
Lot size:
0.14 Acres
Year built:
1990
A broker reciprocity listing Courtesy: REAL ESTATE PROS, 407-381-7861
View additional info

Clean, BRIGHT and MOVE IN READY!!! Prepare to be IMPRESSED with this BEAUTIFUL 4 bedroom, 2 Bath 1598 Sq Ft home in the quaint and quiet Bridgewater Community! This terrific Winter Park home is LIGHT-FILLED, SPACIOUS and has a terrific 3 way split floorplan. Upon entering the home, you will notice the vaulted ceiling, fresh neutral interior wall paint and beautiful OPEN FLOOR PLAN which is perfect for entertaining family and friends as well as enjoying every day life with your family!!! The generously sized main living area connects to the dining area, kitchen and an additional living space/ bonus area behind the living room which could be used for additional seating , toy/ play area, craft area-- you name it!!! To the left as you enter the home is the tastefully updated kitchen with stainless steel appliances, newer shaker style cabinets, deep large sink, tasteful tile backsplash and quartz counter tops. To the right as you move past the entry are 2 secondary bedrooms with brand new luxury vinyl plank flooring/fresh neutral wall paint as well as the completely renovated secondary bathroom! Moving back through the living area you will find the Private and Well-Appointed Primary Bedroom and Primary Bathroom. Both are sure to please and feature Vaulted ceilings, walk-in closet, dual vanity, spacious stall shower and private toilet room. As you head to the back of the home, you find the "bonus space" and the FOURTH BEDROOM!! This 3 way split floor plan is IDEAL!! The fully fenced backyard is the perfect spot to unwind after a busy day-- perfect for those with pets as well. This well-cared for home has been updated and is MOVE IN READY!!!! HVAC 2022, Water Heater 2020, ROOF 2019, Plantation Shutters 2016, ALL FRESH INTERIOR PAINT 3/2025, NEW LUXURY VINYL PLANK flooring in all bedrooms and hallway 3/2025, Secondary Bathroom remodel 3/2025. Easy access to 417 and conveniently located to public am d private schools, shopping, restaurants and entertainment! Don't miss this BEAUTY!

Open House:

Saturday, 3/22 2:00-4:00PM

Beds:
3
Baths:
2.00
Sq.Ft.:
1,975
Status:
NEW LISTING
MLS#:
O6291613
Type:
Single Family
Subdivision:
WINTER PARK PINES REP
Lot size:
0.19 Acres
Year built:
1962
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES, 407-644-1234
View additional info

Welcome to the sought after Winter Park Pines. A neighborhood where children are always riding bikes and playing outside, neighbors look out for one another and neighborhood gatherings are a regular event. When entering the home, you find yourself drawn to the open floor plan and natural light. Beautiful, restored terrazzo floors throughout the house. The eat in kitchen with its great layout has a GE Caf range, oven, and microwave. Three spacious bedrooms. The light filled playroom would also make the perfect office. Paved patio with a raised garden bed can be found in the backyard. New A/C. Zoned for the best schools. Walk to Brookshire Elementary. Enjoy bike rides and walks along the Cady Way Trail. A new renovation project for the Cady Way pool is planned. Close to Baldwin Park, Winter Park, and short ride to the airport. This is not just a home it's a lifestyle.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,645
Status:
NEW LISTING
MLS#:
O6291504
Type:
Single Family
Subdivision:
GLENCOE SUB
Lot size:
0.28 Acres
Year built:
1949
A broker reciprocity listing Courtesy: KELLER WILLIAMS HERITAGE REALTY, 407-862-9700
View additional info

WINTER PARK-Outstanding Renovations! Beautiful 3 Bedrooms 2 Baths! Open concept floor plan, single story with a lot of natural light!REMODELLED Kitchen with Stainless steel appliances, New cabinets, Quartz countertops, with Undermount chef sink, backsplash, faucet. Wood laminate floors & custom tile floors (2020). NEW BATHROOM (5 YEAR NEW) with new upgraded subway tiles & Pebble shower floor, New vanity and New fixtures! Some Newer windows , The 2nd Bathroom was Updated 2020. New AC & Newer hot water(approx 10 years) Brand New Roof 2021!2 New garage doors in 2020, GARAGE Approx 550 square feet two car with Workshop and approx 90 foot long concrete driveway added. Oversize Great Room/ Living Room, Spacious Dining Room with Large Windows & Decorative Shelves & SUPERB GRAND SIZE FAMILY ROOM with Wood Burning Fireplace! Oversized Large Fenced backyard. Highly Sought after- Move in Ready ! HURRY! Won't Last!!

Open House:

Saturday, 3/22 11:00-2:00PM

Beds:
1
Baths:
1.00
Sq.Ft.:
787
Status:
NEW LISTING
MLS#:
O6291726
Type:
Condo, Townhouse
Subdivision:
WINTER PARK GARDENS CONDO
Lot size:
0.09 Acres
Year built:
1964
A broker reciprocity listing Courtesy: BALDWIN PARK REALTY LLC, 407-986-9800
View additional info

Welcome to your serene retreat in the highly desirable Winter Park Gardens community. This beautifully renovated second-floor 1-bedroom, 1-bathroom condo offers an exceptional living experience with modern upgrades and a prime location less than a mile from Park Avenue and Orlando Avenue. Step inside to discover luxury vinyl flooring throughout the entry, living space, and kitchen, complemented by granite countertops, a double oven, a custom-built pantry, and pull-out drawers for added convenience. The open-concept living space extends into a Florida sunroom with floor-to-ceiling sliding windows that double as sliding doors, allowing fresh air to flow through your home. Whether you're in the living room, kitchen, or bedroom, you'll enjoy breathtaking views overlooking the oasis of the lushly landscaped courtyard, pool, tranquil community pond, and beautiful trees. Further down the hall, you'll find new carpeting in the primary bedroom, along with upgraded plantation shutters to the window. Storage is a breeze with custom closets throughout, including a stunning primary closet hidden behind bi-fold doors, offering ample, organized space for all your belongings, along with an elegant entrance hallway closet and a spacious linen closet. The renovated bathroom features a walk-in shower with handicap assistance, thoughtfully designed for ease of use and comfort. Nestled on over 8 acres of meticulously maintained grounds, Winter Park Gardens is a vibrant 55+ community. Residents enjoy a resort-style pool, clubhouse, and lighted walking paths winding through the lush gardens and a bridge overlooking the serene pond views. With assigned parking and ample guest spaces, convenience is never an issue. This prime location places you just minutes from Rollins College, Azalea Tennis Center, and Mead Botanical Gardens, while Downtown Orlando, Baldwin Park, and major highways provide easy access to everything in Central Florida. Additionally, you'll find an array of top-tier local shops and restaurants nearby, as well as convenient everyday services such as hair salons, grocery stores, and more"all just moments from your doorstep.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,788
Status:
NEW LISTING
MLS#:
O6288387
Type:
Single Family
Subdivision:
KINGS COVE
Lot size:
0.33 Acres
Year built:
1989
A broker reciprocity listing Courtesy: BUSTAMANTE REAL ESTATE INC, 407-857-5900
View additional info

FIRE DAMAGED HOUSE - LOTS OF POTENTIAL IN THIS WINTER PARK POOL HOME. This is an exciting opportunity for investors or buyers looking for a project! This home offers a blank canvas for renovation. The property is situated in a quiet, family-friendly neighborhood, making it an ideal candidate for full restoration. With required renovations - this blank canvas will become a beautiful 4 bedroom, 2.5 bath home. Features a spacious screened patio and pool area as well, providing the foundation for a stunning remodel. About $100k in repairs are needed. Once restored, the home has an estimated ARV of $650k to $690k, offering significant potential for a solid return on investment. It's located just minutes away from local parks, recreational facilities and the Winter Park Chain of Lakes. Shopping and dining experiences are nearby along Park Avenue. The location offers easy access to major highways for a quick commute to downtown Orlando and beyond. THIS IS AN AMAZING DEAL!

Beds:
4
Baths:
4.00
Sq.Ft.:
4,314
Status:
NEW LISTING
MLS#:
O6291851
Type:
Single Family
Subdivision:
WINTER PARK
Lot size:
0.89 Acres
Year built:
1935
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES, 407-644-1234
View additional info

Nestled on a sprawling 0.89-acre estate, this luxurious home offers the perfect balance of privacy and convenience, just moments from the vibrant downtown Winter Park. A rare gem, this 1935 James Gamble Rogers masterpiece blends Old World charm with European influences, creating an inviting, character-rich ambiance. The main home features 3 bedrooms, 2 1/2 bathrooms, and 3,908 square feet of elegant living space, complemented by a 1-bedroom, 1-bathroom guest cottage, adding 406 square feet, for a total of 4,314 square feet. Accessed via a long, secluded driveway, this estate seamlessly blends indoor and outdoor living with lush gardens, expansive courtyards, and tranquil patios. Inside, arched doorways, reclaimed doors, and rounded stucco walls evoke a Santa Barbara Mediterranean feel. The kitchen is outfitted with stainless steel appliances, granite countertops, and a butler's pantry"ideal for entertaining. The formal dining room opens to a living room with a curved barrel ceiling, a fireplace, and French doors leading to a garden patio. A sunlit sunroom offers panoramic garden and pool views, perfect for relaxation. The expansive downstairs owner's suite features vaulted ceilings, French doors to the patio, a cozy fireplace, and a lavish marble bath with a Jacuzzi tub, double sinks, and a dressing area with custom cabinetry and two large walk-in closets. Upstairs, two bedrooms share a beautifully renovated marble bath. The detached 2-car garage is adjacent to the laundry room, while the guest house offers a studio layout with terra-cotta floors, a kitchenette, a full bath, and French doors overlooking the pool. The backyard is an oasis of tranquility with a stunning resort-style pool, an expansive patio, and lush landscaping, providing ultimate privacy. This home offers the best of both worlds: a rare opportunity to own a piece of Winter Park history, yet lovingly maintained with modern updates and conveniences throughout.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,015
Status:
NEW LISTING
MLS#:
O6291989
Type:
Single Family
Subdivision:
OLYMPIA HEIGHTS ANNEX
Lot size:
0.2 Acres
Year built:
1948
A broker reciprocity listing Courtesy: LPT REALTY, LLC, 877-366-2213
View additional info

Come build your dream home on this oversized single family corner lot (62.5 by 141.5) in Winter Park Florida with amazing views of Dubsdread Golf Course hole 6. Located just a short drive or walk away from all your favorite shops and restaurants (Agave Azul, Publix, Tap Room, Black Bean Deli) Convenient access to I-4 making it easy to get around the greater Orlando area. Less than a minute drive to Park Maitland School and zoned Princeton Elementary School. The existing single family structure is being offered as is and the owner has no previous information on the home. Demolition date is now scheduled for 4/24/2025.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,460
Status:
NEW LISTING
MLS#:
O6291785
Type:
Condo, Townhouse
Subdivision:
WINTER GREEN
Lot size:
0.04 Acres
Year built:
1988
A broker reciprocity listing Courtesy: RE/MAX TOWN & COUNTRY REALTY, 407-695-2066
View additional info

This Winter Park Townhouse offers an easy-maintenance lifestyle with LOW monthly dues! Very few units come up for sale in this complex- and even fewer END UNITS like this one!! With 2 spacious bedrooms, an open Loft, *AND* a separate flex room that can easily be converted into a 3rd bedroom or private office, you don't want to miss this opportunity to snag this incredible deal!! The flow of this townhouse provides the perfect blend of function and comfort while the private courtyard gives you a place to enjoy the outdoors without having the upkeep of a large yard! Work-from-home? No problem... set up your home office in the Flex Space! Don't want to climb stairs? Problem Solved... there's a DOWNSTAIRS bedroom and Full Bath! Need separate living spaces? Who doesn't, right?... the Loft can fit a full living room set and large TV - or a Pool Table if you're so inclined! Host family and friends for weekly game nights and holidays? Let's do this... the open floorplan expertly connects the living room, dining AND kitchen! Need a laundry room INSIDE?...We Got You! Hate carpet in bedrooms?... Great, so do we! Thinking about picking up Tennis or Pickleball?...Check out the Community Courts (and then cool off in the Community Pool!)! Want a place that's close to all major roads, shopping, great dining options, and schools?....You Found It! Did we mention the ROOF is less than 2 Years NEW??? Grab this gem before someone else does!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,841
Status:
NEW LISTING
MLS#:
O6291619
Type:
Single Family
Subdivision:
JENKINS ADD
Lot size:
0.31 Acres
Year built:
1953
A broker reciprocity listing Courtesy: TRUST EQUITY GROUP LLC, 321-296-9355
View additional info

Charming Winter Park Pool Home - A Rare Opportunity! Nestled in the heart of Winter Park's highly sought after 32789 zip code, this 4-bedroom, 3-bathroom pool home offers timeless charm, abundant space, and unlimited potential! Set on an expansive corner lot, this residence is just steps from Phelps Park, surrounded by tree-lined streets, and minutes from Winter Park's vibrant retail and dining scene.A Home with Character & Possibilities...Step inside to a welcoming foyer that leads to elegant formal living and dining spaces, flooded with natural light from oversized windows. The expansive kitchen boasts wood cabinetry, a pantry, ample storage, and a wine fridge, making it a dream for both everyday living and entertaining. Adjacent to the kitchen, a private dining room features an expansive south-facing window, creating a warm and inviting atmosphere. French doors lead to a charming courtyard walkway that guides you to the refreshing pool, a serene retreat for relaxation and entertaining. The primary suite also offers direct pool access via an updated ensuite bath, featuring a soaking tub, dual sinks, and a spacious walk-in closet. This home provides a Spacious & Functional Layout - Four bedrooms provide ample space, with generous closets and a well-appointed guest bath.Detached 2-car garage with potential for an office or workshop. Additional carport & extended driveway for ample parking. Freshly painted exterior & interior (2025) - a blank canvas for your vision!Prime Location & Endless Potential - This home presents a rare opportunity to own in one of Winter Park's most desirable neighborhoods. Whether you're looking to move in and make it your own or renovate to create your dream home, this is a chance you don't want to miss!Schedule your showing today!

Beds:
4
Baths:
4.00
Sq.Ft.:
4,560
Status:
NEW LISTING
MLS#:
O6291551
Type:
Single Family
Subdivision:
GEORGEANN HOMES
Lot size:
1 Acres
Year built:
1977
A broker reciprocity listing Courtesy: SPECTRUM GLOBAL REALTY, INC, 407-770-0067
View additional info

Experience the ultimate in Winter Park lakefront living on a privately gated acre along the shores of Lake Waunatta. Recently renovated, this striking residence offers a seamless blend of elegance, privacy, and resort-style tranquility. Beautiful lake views from almost every room create a breathtaking backdrop for everyday living. From the moment you enter the courtyard, a sense of serenity takes over with lush, beautiful landscaping and a privacy fence on both sides. Curated soundscapes evoke the feel of a private oasis. The massive windows in the open living areas blur the line between indoors and out, showcasing stunning lake views. The kitchen is beautifully designed and equipped with a Wolf appliance package. Rich gray tones and bold architectural elements make this home sophisticated and effortlessly cool. The first floor includes a fully equipped guest suite with its own kitchen, ideal for extended stays, plus a game room equipped with a fully functioning bar that leads outside to a massive deck, perfect for entertaining. Upstairs, the primary suite is breathtaking, featuring a spa-like bath and office with views overlooking the lake. This home also offers a private boat ramp and a private dock with a boat lift to complete this rare waterfront retreat, offering the perfect balance of seclusion and convenience. Did I mention it has an ample home generator and a smart home package? Ideally situated minutes from the 417 and 408, this home provides easy access to downtown Orlando, the airport, and Central Florida's renowned attractions, making it both a private sanctuary and a gateway to everything Central Florida offers.

Open House:

Sunday, 3/23 11:00-2:00PM

Beds:
3
Baths:
3.00
Sq.Ft.:
3,653
Status:
NEW LISTING
MLS#:
O6284417
Type:
Single Family
Subdivision:
SYLVAN LAKE SHORES
Lot size:
0.42 Acres
Year built:
2000
A broker reciprocity listing Courtesy: KELLER WILLIAMS WINTER PARK, 407-545-6430
View additional info

Experience modern elegance in this stunning Lake Sylvan estate with breathtaking lake views and seamless indoor-outdoor living. The open-concept design features a gourmet kitchen (renovated 2023) with quartzite countertops, a wet bar, and luxe appliances. French doors, a custom gas fireplace, and designer lighting add refined charm to the living room. Step outside to nearly 1500 sqft of additional living space on the lake featuring a heated pool, spa, covered patio with gas fireplace, summer kitchen and lakeside firepit. With three bedrooms and a versatile office (easily a fourth), this home adapts to your needs. The first-floor primary suite opens to the pool, while an upstairs primary suite has dual custom closets, a spa-like bath, and a private flex space. Upgrades include a new roof with gutters and gutter guards (2022), new water heaters (2023), interior paint (2021) exterior paint (2023), water filtration, system, dual propane tanks, security system, plantation shutters, and three AC units. The above garage attic is accessible by staircase and can easily be enclosed to make a 5th bedroom, game room or flex space. This lakefront sanctuary offers privacy, sophistication, and modern convenience plus is located just minutes from Park Avenue's charming shops and restaurants. Don't miss the opportunity to make this lake front home yours. Schedule your private showing today!

Open House:

Sunday, 3/23 11:00-2:00PM

Beds:
3
Baths:
2.00
Sq.Ft.:
1,537
Status:
NEW LISTING
MLS#:
O6290228
Type:
Single Family
Subdivision:
HOWELL BRANCH WOODS
Lot size:
0.19 Acres
Year built:
1977
A broker reciprocity listing Courtesy: LIVE FLORIDA NOW LLC, 407-448-7977
View additional info

Nestled in the heart of Winter Park, this beautifully maintained 3-bedroom, 2-bathroom home offers the perfect blend of comfort and Florida living. Step inside to discover a bright and spacious open-concept layout featuring durable LVP flooring, modern finishes, and plenty of natural light. The updated kitchen boasts stainless steel appliances, quartz countertops, and a breakfast bar, ideal for entertaining or family meals. The primary bedroom is a true oasis with a luxurious en-suite bathroom. Two additional bedrooms provide ample space for family, guests, or a home office. Outside, your private backyard paradise awaits"complete with a sparkling pool, perfect for cooling off on warm days or hosting weekend gatherings. Located just minutes from Winter Park's renowned dining, shopping, and top-rated schools, this home combines convenience with tranquility. New roof/gutters in 2022. Floors, kitchen updated, bathrooms updated, hot water heater in 2021. Interior paint in 2021 and exterior in 2022. Don't miss your chance to own a slice of paradise"schedule your showing today!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,295
Status:
NEW LISTING
MLS#:
O6291369
Type:
Condo, Townhouse
Subdivision:
CEDARWOOD VILLAGE 1
Lot size:
0.04 Acres
Year built:
1981
A broker reciprocity listing Courtesy: MLSB THE BUREAU POWERED BY CAROM REALTY, 407-284-3488
View additional info

Welcome to this beautifully renovated 2-bedroom, 2-bathroom townhouse located in the desirable Cedarwood Village community of Winter Park. This 1,295 sq ft home seamlessly blends modern updates with classic charm, offering a comfortable and stylish living space. The heart of this home boasts a brand-new kitchen equipped with modern appliances, sleek countertops, and ample cabinet space, perfect for culinary enthusiasts. High-grade laminate flooring extends throughout the living areas, providing durability and a contemporary aesthetic, while the entire interior has been freshly painted in neutral tones, creating a bright and inviting atmosphere. Both bathrooms have been thoughtfully updated with modern fixtures and finishes, enhancing both functionality and style. The open-concept living and dining areas feature vaulted ceilings and skylights, filling the space with natural light and offering a welcoming environment for relaxation and entertainment. Residents of Cedarwood Village enjoy access to a community pool, clubhouse, and well-maintained common areas, enhancing the overall living experience. The association fee covers exterior maintenance, landscaping, and access to community amenities. Situated in Winter Park, this townhouse offers proximity to a variety of shopping, dining, and entertainment options. The area is known for its excellent schools and vibrant community atmosphere, making it a sought-after location for families and professionals alike. Don't miss out on this incredible opportunity"schedule your private showing today!

Open House:

Saturday, 3/22 12:00-2:00PM

Beds:
1
Baths:
1.00
Sq.Ft.:
884
Status:
NEW LISTING
MLS#:
O6290860
Type:
Condo, Townhouse
Subdivision:
PHILLIPS CIRCLE REP
Year built:
1960
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES, 407-644-1234
View additional info

Tucked away just two blocks from Park Avenue, this one bedroom, one bathroom corner unit places you in the heart of downtown Winter Park"steps from acclaimed restaurants, charming shops, and the iconic boat tour on Lake Osceola. Situated on the second floor of Building 6 with convenient elevator access, this light filled condo has brand new carpet in the living areas and bedroom, creating a fresh and cozy feel. The kitchen features granite countertops, a built-in oven, glass cooktop, stainless steel refrigerator, and recently painted blue, solid wood cabinetry that adds a fun pop of color to the space. A dedicated dining area is located just off the kitchen and includes sliding glass doors that open to a small private balcony overlooking Morse Blvd"perfect for enjoying your morning coffee. Off the living room, an enclosed sunroom offers bonus living space with abundant natural light, motorized custom blinds, and upgraded windows for improved energy efficiency and sound insulation. The oversized bedroom offers space for a sitting area and features motorized shades for added comfort and privacy. A convenient door allows you to close off the bedroom "ideal for when guests are visiting and need access to the bathroom without entering the bedroom. The unit also comes with one assigned parking space in the garage, additional storage, and the peace of mind that HOA covers electric, water, sewer, trash, building insurance, pool maintenance, landscaping, and on-site management. Whispering Waters is a lakefront community on beautiful Lake Osceola, with water access available to residents"bring your kayak, soak in the serene views, or enjoy a sunset by the water. Whether you're seeking a full-time residence or a part-time getaway, this home offers effortless, low-maintenance living"just lock and leave. Bonus: Since the current owner is under 55, the next buyer can be too (only 85% of residents need to meet the 55+ age requirement). Call today to schedule your private showing!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,066
Status:
NEW LISTING
MLS#:
O6286150
Type:
Condo, Townhouse
Subdivision:
COLONIES
Lot size:
10.07 Acres
Year built:
1974
A broker reciprocity listing Courtesy: REALTY HUB, 888-900-1801
View additional info

Priced to sell! This updated 1st Floor, 2 bed, 2 bath unit, with luxury tile (faux wood) floors and updated amenities, is a great starter home or investment property. Freshly painted and cleaned, ready to move in!The monthly HOA fee include amenities, water & trash pick up, Exterior and ground maintenance. As a resident of the Colonies subdivision, you'll enjoy access to a host of exclusive amenities, including a sparkling community pool, perfect for cooling off on hot summer days or lounging in the sun with a good book as well as tennis courts, dog park and a clubhouse. Conveniently located just moments from the vibrant shops, restaurants, and cultural attractions of downtown Winter Park, as well as top-rated schools and parks, this coveted unit offers the ultimate in luxury living with all the conveniences of modern-day life at your fingertips. Don't miss your opportunity to experience the epitome of luxury living in Winter Park. Schedule your private showing today and make your dream of owning this unit a reality.

Open House:

Sunday, 3/23 10:00-12:00PM

Beds:
4
Baths:
2.00
Sq.Ft.:
2,014
Status:
NEW LISTING
MLS#:
A4644849
Type:
Single Family
Subdivision:
CAROLYN ESTATES
Lot size:
0.25 Acres
Year built:
1982
A broker reciprocity listing Courtesy: MINK REALTY, 502-716-6151
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Welcome to 1776 E Cheryl Dr, located on a quiet cul-de-sac in desirable Winter Park. The home offers a split plan with 4 bedrooms and 2 bathrooms. The living room has a beautiful stone fireplace. It has a separate indoor laundry room and an attached 2-car garage. Notes of interests include a fully renovated guest bathroom (2018), fully renovated kitchen (2023), new roof and gutters (2021), house replumb (2023) and home exterior paint (2024) and new interior paint throughout the home. Outside you will find a beautiful screened in pool to enjoy the Florida sun. It also has a covered area where you can enjoy outside dining. There is ample room on the .24 square foot lot to have a garden or enjoy lawn games. Located in Winter Park, this home is conveniently situated near a variety of shopping, dining, and entertainment options. The home is in the perfect location as there is a short commute to three top-rated Seminole County schools.. With easy access to major highways and public transportation, commuting to work or school is a breeze. Additionally, the neighborhood is known for its friendly atmosphere and sense of community. Don't miss out on the chance to make this lovely property your own!.

Open House:

Saturday, 3/22 12:00-2:00PM

Beds:
5
Baths:
4.00
Sq.Ft.:
2,910
Status:
NEW LISTING
MLS#:
O6285510
Type:
Single Family
Subdivision:
TEMPLE TERRACE
Lot size:
0.41 Acres
Year built:
1954
A broker reciprocity listing Courtesy: COMPASS FLORIDA LLC
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Stunning fully remodeled Winter Park bungalow featuring a 500 square foot detached guest house. This charming residence is perfectly positioned on a rare oversized .41-acre double lot and has been completely transformed, offering a harmonious blend of modern luxury and timeless elegance. The main house features 4 bedrooms and 2.5 baths while the guest house features a living room, bedroom, kitchenette, and a full bathroom. Step inside and you are immediately greeted by a bright, spacious open floor plan. Designed for effortless entertaining, this home features a sleek modern wet bar complete with an under counter ice maker, additional dishwasher, and wine fridge! The gourmet kitchen is a true masterpiece, featuring top-of-the-line stainless steel appliances, upgraded countertops, a walk-in pantry, a large butcher block center island, tile backsplash, and loads of custom cabinetry. There is even a pass-through window to a bar area on the covered lanai. The luxurious primary suite provides a serene escape, designed as a private retreat where you can unwind in ultimate comfort. It boasts an impressive closet and a spa-inspired en-suite bath, complete with a freestanding soaking tub, dual vanities, and a spacious walk-in shower. Outside, the home continues to impress with its private backyard oasis provided by the rare double lot. A sparkling screened in pool, set against lush landscaping, serves as the centerpiece of the expansive patio area. In addition, the beautifully landscaped yard holds a custom fire pit, elevated covered wooden lanai and garden boxes to create the perfect setting for relaxation and gatherings. There is also a spacious covered deck, and a large storage shed. Last but not least, your guest will love the privacy provided by the detached guest house overlooking the pool. Jump on your golf cart and within minutes you're transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park has to offer. Don't miss the opportunity to make this unique Winter Park home yours!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,578
Status:
NEW LISTING
MLS#:
O6290118
Type:
Condo, Townhouse
Subdivision:
WHISPERWOOD CONDO
Lot size:
0.1 Acres
Year built:
1974
A broker reciprocity listing Courtesy: CREEGAN GROUP, 407-622-1111
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One or more photo(s) has been virtually staged. Welcome to this charming two bedroom, two and a half bathroom condo in the heart of Winter Park. This home offers a spacious and functional layout with a half bath on the first floor, perfect for guests, and an interior laundry room for added convenience. The living room features a cozy fireplace, creating a warm and inviting atmosphere. Two sliding glass doors on the first floor lead out to the expansive, fenced-in paver backyard ideal for outdoor relaxation or entertaining. The custom kitchen is a chef's dream, featuring beautiful maple cabinets with crown molding, sleek granite countertops, and high end Frigidaire stainless steel appliances. Tile flooring throughout the living areas and new luxury vinyl upstairs provide both style and durability. Upstairs, you'll find the primary bedroom, offering a private sanctuary with a stand-up shower, a spacious walk in closet, and a screened-in porch that overlooks a serene, lush green space. The generously sized second bedroom and a well appointed bathroom, featuring a luxurious Jacuzzi tub, complete the upper level. Additionally, there's an oversized storage room for all your extra needs. Exterior features include an oversized carport with a sun porch and extra storage space. The HOA includes exterior maintenance, pest control, as well as access to the community pool and clubhouse. Ideally located in Winter Park, this condo offers a peaceful setting while being just minutes away from local restaurants, shopping centers, major roadways, and top-rated schools. This condo is the perfect blend of comfort, style, and convenience, making it a must-see in Winter Park!

Beds:
4
Baths:
6.00
Sq.Ft.:
5,097
Status:
NEW LISTING
MLS#:
O6289739
Type:
Single Family
Subdivision:
STONEHURST ESTATES
Lot size:
0.5 Acres
Year built:
2001
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES, 407-644-1234
View additional info

Set on a sprawling half-acre, surrounded by meticulously manicured landscaping, this custom-built traditional estate exemplifies refined luxury, modern convenience, and an unparalleled lifestyle.The red brick faade, covered porches with glass doors, and gated side porte-cochere set a timeless tone, while two-story fluted columns add stately elegance. Inside, classic architectural details merge with modern design, highlighted by two-story coffered ceilings, intricate millwork, and expansive windows and French doors that flood the home with natural light.Thoughtfully designed for both entertaining and everyday living, the gourmet kitchen includes a 6-burner Viking gas range, double dishwashers and sinks, a paneled refrigerator and separate full-sized freezer, a walk-in pantry, and an oversized island with breakfast bar seating.The first floor features a private primary retreat, two powder rooms, a workstation/mudroom accessible off the porte-cochere, and one of two laundry rooms.Upstairs offers three spacious bedroom suites with walk-in closets, a versatile bonus room, and a second laundry room.Embrace the Florida lifestyle from a two-story covered brick patio with a built-in gas grill, overlooking the private, fenced-in backyard oasis and breathtaking saltwater pool and heated spa, all elevated by a three-tier fountain and fire pit area, and wrapped in lush landscaping; this outdoor space is truly magical and not easily replicated in Winter Park!A circular driveway provides ample parking, while a gated side drive leads to an oversized, detached three-car garage with a bonus room above"ideal for a gym or studio.This particularly grand, wide street in the City of Winter Park is something truly special. Ideally located near Baldwin Park, Corrine Drive, and Park Avenue, and zoned for highly regarded Audubon K-8, this estate is more than a home"it's a statement in timeless elegance. *Ask for a list of improvements, the floorplan and click on the virtual tour!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,525
Status:
NEW LISTING
MLS#:
O6290615
Type:
Single Family
Subdivision:
SPRINGVIEW
Lot size:
0.23 Acres
Year built:
1984
A broker reciprocity listing Courtesy: ORLANDO EXPERT REALTY LLC, 321-274-6991
View additional info

Welcome to this meticulously updated and **FULLY FENCED POOL HOME**, reflecting exceptional pride in ownership and featuring numerous thoughtful upgrades, all nestled in the desirable Winter Park area with **NO HOA** and a **NEW METAL ROOF (2022) ** This home is ideally situated on a **QUIET CUL-DE-SAC**, offering additional privacy and tranquility. The **SOLID BLOCK CONSTRUCTION** ensures durability and long-term peace of mind, providing the home's overall structural integrity. It offers 3 bedrooms, 2 bathrooms, and **A VERSATILE BONUS ROOM** with a closet on the ground floor, perfect for a home office, a 4th bedroom, or extra storage, adapting effortlessly to your needs.As you step inside, you'll be greeted by a bright, inviting living room, with new plantation shutters and tile flooring throughout. The open layout effortlessly transitions into the dining area, where French doors lead to the backyard, ideal for seamless indoor-outdoor living.The modern kitchen features warm wood cabinetry, stainless steel appliances, a stylish glass tile backsplash, and a cozy nook area, perfect for casual meals or enjoying your morning coffee. Upstairs, all the bedrooms have been updated with beautiful wood floors, giving the home a fresh, contemporary feel. The remodeled bathrooms combine both style and function, offering comfort for your daily routines.Step outside to your private backyard retreat: an entertainer's dream and **SPACE GALORE!**The sparkling swimming pool, resurfaced in 2024 and color-changing pool lights, is the centerpiece of this expansive backyard, offering the perfect spot to relax and cool off on warm Florida days. The fully fenced yard ensures complete privacy, with no rear neighbors. For outdoor dining or relaxation, the shaded gazebo on the concrete pad provides a cozy retreat, complete with a built-in charcoal grill, Bluetooth sound system, and hanging lights, creating the ideal setting for evening meals or entertaining guests.The yard has been freshly landscaped with new sod and includes an efficient well-powered irrigation system, ensuring the space stays lush and green year-round while helping to reduce utility costs. For added convenience, a storage shed offers ample space for tools and outdoor equipment, keeping everything organized and accessible. With plenty of space, you can easily add a swing set, garden beds, or a fire pit to enhance your outdoor oasis. Additional upgrades include new gutters, new insulation (2020), and a new garage door with updated features (2023) and alarm system, giving you peace of mind for years to come.Located nearby schools and shopping, this home offers the perfect balance of convenience and comfort. This is a rare opportunity to own a meticulously updated home in the desirable Winter Park area. Don't miss your chance to make this exceptional property yours, schedule your private tour today!

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