Location: Winter Park , 32792
Do Not Show Listings
1507 GOLFSIDE DR, WINTER PARK, FL 32792
$925,00018 Days on yellowkey MLS ID: O6395355
REDUCED by $50,000 (5.1%) on 04/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2003 Built: 1981 Tax: $2,783 (2025)Community: Greenview At Winter PinesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,783
Elementary School: Brookshire Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: One or more photo(s) has been virtually staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW Wood & porcelain tile flooring throughout. Updates include (but definitely not limited to) BRAND new kitchen with Stainless Steel Appliances, new cabinets & quartz countertops. Formal living & dining rooms PLUS Family room with vaulted ceilings featuring a new electric fireplace for amazing ambiance and sliding doors inviting you to new brick pavered 31x 11 screened porch overlooking newly refinished sparkling pool & golf course (no rear or side neighbors!!) Bedroom wing of home offers a large inside laundry room, beautiful guest/pool bath with dual sinks & shower/tub and 2 fresh guest bedrooms. THE PRIMARY SUITE has been thoughtfully remodeled with sliding doors to pool, AMAZING primary bath with oversized work-of-art shower with dual shower heads, dual vanity, separate water closet & HUGE walk-in closet! Extras include: NEW double paned windows & 3 sliding doors to pool/patio, crown molding, NEW roof November 2024, oversized 2 car garage, NEW landscaping, all NEW ceiling fans & light fixtures, NO HOA!! Zoned for Brookshire Elementary, Glenridge Middle & Winter Park High. WELCOME HOME!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Catherine D'Amico (407-252-3210)
2087 LAURELWOOD WAY, WINTER PARK, FL 32792
$659,000216 Days on yellowkey MLS ID: O6344482
REDUCED by $5,000 (0.8%) on 04/20/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1920 Built: 2019Monthly Fee: $236 Tax: $4,680 (2024)Community: Preserve At Hawks CrestSingle Family
Taxes:$4,680
Elementary School: Eastbrook Elementary
High School: Lake Howell High
Tax Year: 2024
Middle School: Tuskawilla Middle
Remarks: One or more photo(s) has been virtually staged. Set within the serene gated community of Hawks Crest in Winter Park, this beautifully designed single-story home combines modern comfort with resort-style living. Featuring 4 bedrooms, 2 baths, and 1,920 sq. ft. of thoughtfully crafted space, it’s the perfect blend of style and function. Inside, an open-concept layout creates seamless flow between the spacious family room, dining area, and gourmet kitchen—ideal for entertaining and everyday living. The kitchen offers granite countertops, large island seating, and stainless-steel appliances. The private owner’s suite is a relaxing retreat with a walk-in closet and spa-inspired bath, while three additional bedrooms provide flexibility for family, guests, or a home office. Step outside to a covered patio and low-maintenance yard designed for year-round Florida living, and pond view. Hawks Crest residents enjoy exclusive amenities including a clubhouse with fitness center, resort-style pool, splash pad, dog park, playgrounds, and private access to Lake Howell for kayaking and paddle boarding. The neighborhood is also minutes from local favorites like Kelly’s Ice Cream and Foxtail Coffee, with downtown Maitland, Park Avenue, and top-rated schools just minutes away. This home delivers not just a place to live, but a lifestyle defined by convenience, community, and charm. Don’t miss your chance to own in one of Winter Park’s most desirable neighborhoods—schedule your private showing today.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Brian Rotenberger (407-948-8478)
2052 LEANNE CT, WINTER PARK, FL 32792
$450,00076 Days on yellowkey MLS ID: O6379323
REDUCED by $6,000 (1.3%) on 04/15/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2264 Built: 1969 Tax: $1,581 (2024)Community: Eastbrook Sub Unit 15Spa: NoSingle Family
Taxes:$1,581
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to 2052 Leanne Ct, a home that exudes warmth and elegance. The living room is graced with a cozy fireplace, perfect for those chilly evenings. The kitchen is a chef's dream, boasting all stainless steel appliances for a sleek, modern look. The primary bedroom is a haven of comfort with double closets for ample storage. The primary bathroom is a sanctuary with double sinks, providing ample space for your morning routine. The fenced-in backyard provides a private outdoor space for relaxation and entertainment. The home has been recently updated with fresh interior and exterior paint, giving it a clean, refreshed look. New flooring throughout the home adds a touch of sophistication and durability. The new appliances ensure efficiency and convenience. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
661 SELKIRK DR, WINTER PARK, FL 32792
$650,000180 Days on yellowkey MLS ID: O6354700
REDUCED by $25,000 (3.7%) on 04/16/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2150 Built: 1962 Tax: $2,353 (2024)Community: Kenilworth Shores Sec 05Single Family
Taxes:$2,353
Remarks: One or more photo(s) has been virtually staged. Welcome to the highly sought-after Kenilworth Shores community, a neighborhood loved for its charm, strong sense of community, and convenient Winter Park lifestyle. From the moment you walk through the front door, the home offers a warm and welcoming flow with a thoughtfully designed split layout. The spacious living room to the left creates the perfect setting for slow mornings with coffee, reading a book, or gathering with guests, while the dedicated dining room to the right is ideal for hosting holiday dinners and special celebrations. As you move toward the center of the home, the kitchen becomes the true heart of daily life—perfectly positioned to stay connected while cooking, entertaining, or helping with homework. Just beyond, the expansive family room, with a cozy fireplace, invites you to unwind, host game nights, or gather with loved ones for movie evenings. Upstairs, the home continues to balance comfort and privacy. Two guest bedrooms and a shared bathroom provide the perfect setup for family, guests, or a home office, while the primary suite is tucked away on the opposite side, creating a peaceful retreat at the end of the day. The oversized suite offers plenty of space to relax, along with a large walk-in closet and private bathroom designed for everyday comfort. Step outside and enjoy the Florida lifestyle with a covered patio overlooking a large fenced backyard—perfect for weekend barbecues, kids and pets playing freely, or simply enjoying the beautiful weather. Living here also means being just minutes from some of the best parks and amenities in the area. Spend afternoons biking the trails at Cady Way Park, enjoying playgrounds and green space at Baldwin Park, or exploring the shops, restaurants, and vibrant community events in both Winter Park and Baldwin Park. With top-rated schools nearby and easy access to 417, 408, and I-4, commuting to downtown Orlando, the theme parks, or even a weekend trip to the beach is effortless. This is more than just a home—it’s a lifestyle centered around comfort, community, and convenience. Schedule your showing today and come experience Winter Park living for yourself.
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: David Miller (321-236-6761)
3057 AARON BURR AVE #1, WINTER PARK, FL 32792
$116,000138 Days on yellowkey MLS ID: O6364189
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1066 Built: 1974Monthly Fee: $409 Tax: $1,911 (2024)Community: ColoniesCondo
Taxes:$1,911
Remarks: Back in market for Buyer finance .A great living in Winter Park. This 2-bedroom, 2-bath Furnished condo in The Colonies offers an excellent opportunity for investors or first-time buyers. Recently updated with new flooring and new painting the unit is ready for a new owner. The location is a major draw, just minutes from Full Sail University,Sam Wearhouse, Valencia College, UCF, Park Avenue, Downtown Orlando, and Orlando International Airport. With highly rated Winter Park schools, and shopping, dining, and cultural attractions nearby,. A rare chance to own in Winter Park at a great price, this condo combines strong value with a prime location.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Amin Abraham (407-230-0803)
1108 FAIRWAY DR, WINTER PARK, FL 32792
$725,00052 Days on yellowkey MLS ID: O6386266
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1677 Built: 1978 Tax: $6,713 (2024)Community: Golfside Sec 03Single Family
Taxes:$6,713
Remarks: Offering WELL BELOW appraised value!! Buyer financing fell through, act quickly this one wont last long. In one of Winter Parks most sought after neighborhoods, take a look at this exceptional 3-bedroom, 2-bathroom pool home with an additional bonus space. Completely reimagined with a designer’s eye, this residence blends high-end aesthetic with the ultimate peace of mind—with a newer roof, A/C, and water heater. Step inside to a Sun-filled sanctuary featuring new luxury vinyl plank flooring and gorgeous tile. The heart of the home is the brand-new chef’s kitchen, featuring custom white oak wood cabinetry, rare Taj Mahal quartzite countertops, and elegant champagne bronze finishes throughout. The kitchen flows seamlessly into the living areas, where new tile work elevates the wet areas for a cohesive, upscale feel. Work from home in style in the dedicated bonus room, an ideal footprint for a private office or creative studio. This home features true functionally for a family to live in everyday. This one of a kind home features a custom in home laundry room, custom vanities, a fireplace made to enhance the homes aesthetic & custom doors through the entire home. Beyond the interior, your private Florida lifestyle awaits. Retreat to the expansive screened-in pool, patio and large backyard. Located just steps from the Winter Park Pines Golf Course and the scenic Cady Way Trail, this home offers more than just a renovation—it offers a lifestyle. Enjoy easy access to the clubhouse for dining, top-rated schools, and the vibrant culture of downtown Winter Park. With every detail thoughtfully curated and major systems already updated, this is the turnkey masterpiece you’ve been waiting for.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Rene Droz, Iii (407-484-8786)
731 BONGART RD, WINTER PARK, FL 32792
$499,999108 Days on yellowkey MLS ID: S5140952
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1826 Built: 1961 Tax: $5,910 (2025)Community: Winter Park EstatesSingle Family
Taxes:$5,910
Elementary School: Lakemont Elem
Middle School: Maitland Middle
Remarks: One or more photo(s) has been virtually staged. Experience luxury living in this stunning, fully remodeled single-family home located in the heart of Winter Park, where modern sophistication meets exceptional functionality. This spectacular residence features a total of 4 spacious bedrooms and 3 modern bathrooms, boasting sleek laminate flooring throughout and a chef-inspired kitchen fully equipped with premium stainless steel appliances. A standout feature of this property is its versatile layout: one bedroom and one bathroom are completely separate from the main living area, offering the perfect solution for guest privacy, a multi-generational suite, or an opportunity to generate additional rental income. Outside, the massive backyard and sparkling pool provide an ideal setting for family gatherings and outdoor entertainment, all while being nestled in a prime location just minutes from the iconic Park Avenue shopping district, the Winter Park Farmer’s Market, and convenient access to the 436. This home is the ultimate choice for those seeking the perfect blend of suburban tranquility and urban convenience in the very best of Central Florida living.
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Maria Gomez Arevalo, Pa (407-705-7203)
2015 SUMMERFIELD RD, WINTER PARK, FL 32792
$1,375,000165 Days on yellowkey MLS ID: O6357615
Bed: 4 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 3024 Built: 1957 Tax: $7,243 (2025)Community: Kenilworth Shores Sec 07Spa: NoSingle Family
Taxes:$7,243
Remarks: Experience refined Winter Park living in Kenilworth Shores, a highly sought after neighborhood near Baldwin Park, Lake Baldwin trails, and the dining and boutiques of Park Avenue. This location places you close to Rollins College, Winter Park High, and the cultural center of Winter Park FL. Inside, natural light moves through open living spaces finished with wide porcelain tile floors. The kitchen stands as a sophisticated gathering space with a large quartz island, custom cabinetry, Bosch appliances, and a walk in pantry. The primary suite offers a peaceful retreat with direct access to the pool and a spa inspired bath. A second ensuite bedroom, dedicated office, and generous flex room provide versatility for daily living. The backyard feels like a private resort with a covered outdoor kitchen and a sparkling pool framed by thoughtful landscaping. This property may qualify for a seller funded permanent rate buydown with a participating lender. Equal Housing Opportunity.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Christina Fata (407-917-8946)
744 CORNWALL RD, WINTER PARK, FL 32792
$695,000262 Days on yellowkey MLS ID: O6332168
REDUCED by $20,000 (2.8%) on 04/15/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1968 Built: 1968 Tax: $5,359 (2024)Community: Winter Park PinesSpa: NoSingle Family
Taxes:$5,359
Remarks: Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing pool, pickleball courts, and miles of trails for jogging, biking, or leisurely strolls. Enjoy the outdoors while being in close proximity to shopping, dining, and the celebrated Winter Park schools.Recent updates make this home truly special. The new A/C system and upgraded electrical panel—complete with room for additional breakers—ensure your comfort and convenience. The manifold system has also been updated, and the roof was newly installed in 2018 for peace of mind.Additionally, half of the windows have been replaced with high-quality Anderson windows, enhancing both energy efficiency and natural light.Don’t miss the opportunity to own this well-maintained home in a vibrant neighborhood that perfectly balances recreation and relaxation. Schedule your showing today!
Listing is courtesy of: VERSALIS REALTY POWERED BY SELLSTATE (407-608-9593)
Listing Agent: Tammy Cuddy (407-608-9593)
200 SAINT ANDREWS BLVD #2901, WINTER PARK, FL 32792
$225,00018 Days on yellowkey MLS ID: O6395720
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1266 Built: 1970Monthly Fee: $451 Tax: $2,131 (2025)Community: Four Seasons CondoCondo
Taxes:$2,131
Remarks: Welcome to this spacious and well-maintained 2 story townhome in the heart of Winter Park, located in the highly sought-after Four Seasons community. This 2-bedroom, 1.5-bath unit offers 1,266 square feet of comfortable living space with a functional layout, abundant natural light, and thoughtful updates throughout. Step inside to find a spacious kitchen, renovated in 2016, featuring wood cabinetry, granite countertops, black appliances, and a dishwasher replaced in 2023, perfect for everyday cooking and entertaining. Just off the kitchen, enjoy a dedicated dining area, ideal for hosting dinners or creating a flexible space for a home office or additional seating. The inviting living room provides plenty of space to relax and gather, with sliding glass doors that lead to your private, fully fenced, tree-shaded patio complete with a storage shed - an ideal spot to enjoy your morning coffee or unwind in the evenings. The patio also offers convenient access to your covered, deeded carport space, #49. Both bedrooms are generously sized, with the primary bedroom featuring dual closets and a ceiling fan for added comfort. The home includes a full bathroom and a convenient half bath, both thoughtfully updated with new toilets and upgraded vanities, including a quartz countertop and stylish shiplap accent in the guest bath. Additional interior highlights include custom closet features, a laundry closet with a new stackable washer and dryer(included), ceiling fans and blinds throughout, fresh interior paint (2024), and an HVAC system updated in 2023, providing peace of mind and modern convenience. Residents of Four Seasons enjoy access to a variety of amenities including 3 swimming pools, a clubhouse with fitness center, tennis and shuffleboard courts, all within a quaint, established neighborhood with tree-lined walkways. Ideally located just minutes from Ward Park, Winter Park Pines Golf Club, YMCA, AdventHealth Winter Park, and the Center for Health & Wellbeing. Enjoy easy access to shopping and dining along Aloma Avenue including Publix, Sprouts, and Aldi, as well as being less than 10 minutes from Park Avenue’s renowned restaurants and boutiques. Conveniently located near SR 436 with quick access to 417 and 408, and approximately 25 minutes to Orlando International Airport. Zoned for top-rated schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. Don’t miss your opportunity to own in one of Winter Park’s most desirable communities—schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Amy Turner (407-803-3885)
2401 ANTILLES DR, WINTER PARK, FL 32792
$320,000166 Days on yellowkey MLS ID: O6357934
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1719 Built: 1977Monthly Fee: $95Community: Windward Square Sec 1Townhouse
Taxes:$0
Remarks: Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. The home has newer A/C, high impact windows and the home has been re-piped for your peace of mind. This is a wonderful space and great to prep for a dinner party! Open floor concept with dining room and family room. Enclosed Florida room with high impact windows is great extra living space marking this home just over 1700sf. Master bedroom is a good size with walk in closet. Secondary rooms are spacious and full 2nd bath. You have a wonderful front fenced courtyard and a nice sized fenced back yard. End unit and 2 assigned car parking spaces. Community features low HOA and community pool, gated back entrance for easy access to Semoran, tennis courts and club house. Zoned for great Seminole County schools and minutes to shopping/dining, Altamonte Springs Mall, Downtown Winter Park, Full Sail University and to UCF. This is a great one level townhome with very reasonable HOA.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: George Freelove (407-408-5167)
4864 TANGERINE AVE, WINTER PARK, FL 32792
$200,00062 Days on yellowkey MLS ID: O6383320
INCREASED by $1,000 (0.5%) on 04/09/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1059 Built: 1973Monthly Fee: $441 Tax: $2,828 (2025)Community: Wrenwood CondoTownhouse
Taxes:$2,828
Remarks: One or more photo(s) has been virtually staged. 4.99% INTEREST RATE OFFERED FOR QUALIFIED BUYERS! This low-maintenance Winter Park condo just became even more affordable ... and it truly checks all the boxes! Enjoy single-story living with no neighbors above or below, corner-unit privacy, a screened patio overlooking the spacious courtyard, updated kitchen and baths, and major mechanical updates already taken care of. Add in a community pool, sidewalks, pet stations, and an unbeatable Winter Park location - and this 2-bedroom, 2-bath condo offers the ideal combination of comfort, convenience, privacy, and value. Inside, you’ll find a functional split-bedroom floor plan, spacious living and dining areas, indoor laundry, and a screened patio that adds valuable outdoor living space. The one-story layout offers easy everyday living, while the corner-unit location provides added privacy and a more desirable setting within the community. The flexible floor plan works well for everyday living, guests, roommates, or even a home office setup. Located in a community with a pool and situated near shopping, dining, major roadways, and daily conveniences, this property offers easy access to University of Central Florida, Full Sail University, SR-417, FL-436, Downtown Winter Park, and Downtown Orlando. Whether you are searching for a primary residence, a first home, or a low-maintenance property in a central location, this home checks all the boxes. The special financing rate equates to a savings of approximately $213 per month for qualified buyers! Now more than ever, if you’ve been searching for an affordable, easy-maintenance, Move-in Ready property in Winter Park ... this is your sign! Seller offering an incredible savings to help you on your path to homeownership. Terms and conditions apply. Call for details.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Allison Day (407-617-2881)
3463 ARNEL DR, WINTER PARK, FL 32792
$459,90034 Days on yellowkey MLS ID: O6390301
REDUCED by $20,000 (4.2%) on 04/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1770 Built: 1967 Tax: $4,648 (2024)Community: Eastbrook Sub Unit 11Single Family
Taxes:$4,648
Remarks: PRICE IMPROVEMENT!! Your pool home in Winter Park just became an even better opportunity. This home offers 3 bedrooms plus a versatile bonus room, approximately 1,770 sq ft of living space, built in 1967, with a 2-car garage and extended driveway for extra parking — all located in the established Eastbrook community with NO HOA. Major updates already done for you: roof 2018, solar panels 2020 (fully paid off), water heater 2019, and AC replaced in July 2013. A home warranty through First American Home Warranty is included, giving added peace of mind on major systems. Inside, you’ll find a bright and functional layout with comfortable living and dining spaces that flow naturally. The kitchen has been updated with granite countertops and modern cabinetry, and both bathrooms feature clean, updated finishes. The bonus room gives you flexibility — perfect for a home office, gym, playroom, or even a 4th bedroom setup. Step outside to your fully fenced backyard with a private pool — ideal for relaxing, entertaining, and enjoying Florida living year-round, with a great balance of pool deck and green space. Location is key — just minutes to Park Avenue, Rollins College, Full Sail University, and University of Central Florida, plus easy access to major highways and top-rated Seminole County schools. With the new price, this is a strong opportunity in Winter Park — especially for buyers looking for space, a pool, and no HOA.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
3131 LOWNDES DR, WINTER PARK, FL 32792
$529,95041 Days on yellowkey MLS ID: O6388846
REDUCED by $4,950 (0.9%) on 04/16/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2126 Built: 1967 Tax: $1,559 (2024)Community: Georgetown EstatesSingle Family
Taxes:$1,559
Remarks: Enjoy the Winter Park Lifestyle in this Beautiful 4 Bedroom Pool Home! The Entire Interior is New, Furnished and Move-in Ready! Entertain in style with a Large Eat-In Kitchen, Stainless Steel Appliances, Soft-Close Cabinetry and Quartz Countertops. Open Floorplan with Entryway into the Living and Dining area that overlooks your Screen-Enclosed Pool/ outdoor Living Space with a Fenced Yard. Versatile Flex Space perfect for a Home-Office, Entertainment Room, or cozy Family Retreat. Three Bedrooms on one side of the house with a Huge Tranquil Master Suite on the other side. Indulge in the Oversized Walk-In Steam Shower, Custom Double Sinks with Backlit Mirrors and Double Closets in the Dressing Area. Master Suite has a Real Fireplace and Pool access through Sliding Glass Doors. Luxury Vinyl Plank Flooring and Fresh Paint throughout. Elegant Designer Wall and Floor Tiles in the Bathrooms with New Sinks, hardware, and faucets. Newer Roof (2021). Light and bright. This home is a gem. The floorplan must be seen to be appreciated. This home is nestled on a Quiet tree-lined street, near top-tier restaurants, businesses, shopping, parks, recreation, top rated schools, and Park Avenue only 4 miles away. Two Workshop/Sheds for storage and creative projects in the back yard. Schedule your private tour today!
Listing is courtesy of: A +ROI PROPERTY (407-718-7994)
Listing Agent: Rene Fossey (407-718-7994)
1926 NATALEN RD, WINTER PARK, FL 32792
$649,90045 Days on yellowkey MLS ID: O6388308
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1469 Built: 1957 Tax: $7,308 (2024)Community: Kenilworth Shores Sec 07Single Family
Taxes:$7,308
Remarks: ***MUST SEE WINTER PARK POOL HOME*** Explore the virtual tours to fully appreciate the beauty of this completely renovated 3 bedroom/2 bath solid block pool home nestled in the highly desirable Kenilworth Shores community in Winter Park. This move-in-ready home features an open layout with vaulted ceilings and an abundance of natural light, highlighted by a large free-flowing kitchen with all the amenities... new stainless-steel GE appliances, elegant quartz countertops, sturdy oversized soft-close shaker cabinets and two large built-in wall pantries. The open living area includes a cozy formal dining room with additional countertop seating, and a picturesque sliding glass door opens to an extra-large 40 x 12 outdoor covered porch that provides additional casual outdoor living space. The spacious primary bedroom has a vaulted ceiling and his/her closets, with private access to the backyard covered porch, and features a fully renovated en-suite bath. The secondary bathroom has been tastefully upgraded, as well. Freshly painted inside and out, this immaculate home has new waterproof LVP flooring throughout, new light fixtures and ceiling fans, and stylish window shade coverings on every window. With an indoor laundry room and a two-car carport, this worry-free home features a new AC unit installed in 2025, a new electrical panel and updated plumbing, and a roof that was replaced in 2018. Setting this home apart is your private outdoor private backyard oasis, showcasing a gorgeous 32 ft long/10 ft deep in- ground pool plus a unique outdoor kitchen . . . perfect for family gatherings or hosting a Bar-b-que pool party . . . and with a generously sized 10’ x 18’ shed with full electric providing additional storage solutions or living options, this fully fenced-in backyard is truly a tranquil outdoor haven. Zoned for excellent Winter Park schools, this home is located four blocks from Winter Park High and less than a mile from Brookshire Elementary and Glenridge Middle. It comes with deeded access to the boat ramp and fishing dock at Lake Berry. Blue Jacket Park and Cady Way Park are just down the street, showcasing great bike trails for walking and jogging. The well-known shopping and restaurants of downtown Park Avenue and Baldwin Park are just minutes away. Rollins College, UCF, Full Sail University, and Winter Pines Golf Course are all close by. And Advent Health/Winter Park Hospital is less than a mile down the street. This is a quiet, family-friendly community known for its tranquility and peaceful living. Don’t miss this opportunity to make this wonderful home your very own. Schedule your showing today.
Listing is courtesy of: JAMIESON PROPERTIES, INC. (407-876-2730)
Listing Agent: Joseph Cosgrove (407-470-0892)
1515 WINTER GREEN BLVD, WINTER PARK, FL 32792
$315,00046 Days on yellowkey MLS ID: O6384755
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 1652 Built: 1984Monthly Fee: $188 Tax: $3,993 (2024)Community: Winter GreenTownhouse
Taxes:$3,993
Elementary School: English Estates Elementary
Remarks: Offering the comfort and feel of a single-family home with the convenience of townhome living, this beautifully maintained two-story residence features 3 bedrooms, 2.5 baths, and a private courtyard conveniently located in Winter Park. Sliding glass doors throughout the home fill the interior with natural light and create a seamless connection to your private outdoor courtyard. Inside, the spacious layout is complemented by low-maintenance tile flooring throughout and a cozy wood-burning fireplace, adding warmth and character to the main living area. The kitchen is well-appointed with granite countertops, stainless steel appliances, and a newer refrigerator, while the generously sized bedrooms provide comfortable retreats. The primary suite features two closets and an ensuite bath with dual sinks. Major system updates provide exceptional peace of mind, including a brand-new roof and HVAC system installed in January 2026, along with fresh exterior paint, newer gutters (approximately three years old), and a newer fence. The washer and dryer convey, making this home truly move-in ready. The community offers an exceptionally low HOA fee of under $200 per month, adding to the home’s overall value. Ideally located with easy access to Winter Park, Maitland, Full Sail University, UCF, Rollins College, and Valencia College, as well as nearby shopping, dining, and major roadways. With its spacious design, private outdoor space, and proven rental history, this property presents an outstanding opportunity as either a primary residence or investment. Reach out to schedule your private showing now!
Listing Agent: Jill Healey (407-797-1420)
330 ELKHORN CT, WINTER PARK, FL 32792
$559,90085 Days on yellowkey MLS ID: O6376757
REDUCED by $10,000 (1.8%) on 04/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1570 Built: 1965 Tax: $2,086 (2025)Community: Winter Park Pines Merrie OaksSingle Family
Taxes:$2,086
Remarks: 330 Elkhorn Ct is a beautifully renovated home located in the highly desired Winter Park Pines community. Freshly updated with a 2025 electric panel, 2025 A/C system, and a 2024 roof, offering modern efficiency, peace of mind, and big-ticket upgrades already taken care of! Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette that feels clean and inviting. The kitchen has been thoughtfully updated with shaker-style cabinetry, sleek countertops, stainless steel appliances, and designer finishes—including a farmhouse sink and gold hardware/fixtures that add a high-end touch. The bedrooms offer comfortable space with updated finishes throughout, while the oversized backyard provides plenty of room to relax, entertain, garden, or create your ideal outdoor setup. Conveniently located near shopping, dining, parks, and major roadways—and zoned for top-rated schools including Winter Park High School—this home is a standout opportunity in one of the area’s most sought-after neighborhoods.
Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)
Listing Agent: Neil Chetram (407-752-1597)
7794 COUNTRY PL #2, WINTER PARK, FL 32792
$241,9003 Days on yellowkey MLS ID: O6397587
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1068 Built: 1988Monthly Fee: $296 Tax: $2,620 (2024)Community: Goldenrod Villas CondoSpa: NoCondo
Taxes:$2,620
Remarks: Winter Park Clean, updated condo in Move In Condition - The newest condo's year built are located on the last street in the complex where this unit is located which features more contemporary open floor plans and high ceilings. Enjoy the One story living. No apartment living with noisy neighbors. Another BONUS is *** NO condo neighbors across the street from you - private!!** This unit is second to the end of a Quiet Dead End Street. Step into a bright and airy condo featuring laminate and tile floors. Newer painted pastel colors throughout. The updated contemporary kitchen has newer Pecan colored cabinets and newer granite counter tops with stylish designer tile back splash. Both bathrooms have newer vanities and granite counter tops. The second bath features a designer Pedestal vanity with granite top. Many upgraded finishes and fixtures throughout. Features a split bedroom floor plan that provides privacy, both bedrooms have spacious walk-in closets. *** Open living area shines with natural sun light and is open to a screened porch, providing access to the private, fenced back courtyard. This condo has a New (December 2024) High efficiency RHEEM 15.3 SEER AC unit with Heat Pump that helps keep utility costs lower, New Roof (2021), New 6 panel Front entry door January (2025), New carpet in both bedrooms installed January (2025), Replumbed with New PEX plumbing pipes, New Refrigerator (2025) New light fixtures throughout. Features an open eat in kitchen and a large breakfast bar open to living room. As a resident, you'll have access to the community pool and the convenience of being close to the Cross Seminole Trail and Cady Way Trail, Winter Park Village, UCF and Full Sail. This location offers easy access to major roadways, shopping, and dining and is served by the reputable Seminole County Schools. Complete with fenced backyard! Community has swimming pool & bathrooms. ** Exterior of building is scheduled to be painted. ** Professionally cleaned top to bottom for new owners. Never smoked in.
Listing Agent: Tom Bercini (407-925-4760)
2317 SUN VALLEY CIR #2317, WINTER PARK, FL 32792
$279,0003 Days on yellowkey MLS ID: O6398500
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1295 Built: 1987 Tax: $1,107 (2025)Community: Cedarwood Village 1Condo
Taxes:$1,107
Remarks: Discover comfort and convenience in this charming, spacious 2-bedroom, 2-bath residence nestled in the heart of Winter Park! Step inside to an inviting living room with a vaulted ceiling. The fully equipped open-floor kitchen, featuring ample roomy cabinets, is perfect for everyday living and entertaining. The thoughtfully designed split floor plan enhances functionality and privacy. Elegant, durable flooring throughout the home ensures easy maintenance. Enjoy the walk-in shower and bathtub with upgraded plumbing and tile. A convenient coffee nook sits just off the kitchen. The spacious patio is ideal for entertaining guests and enjoying outdoor time. Community amenities include a swimming pool and tennis courts, supporting a low-maintenance, active lifestyle.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)
Listing Agent: Robert Arnold, Jr (407-389-7318)
2681 FITZHUGH RD, WINTER PARK, FL 32792
$750,00060 Days on yellowkey MLS ID: O6383699
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2375 Built: 1966 Tax: $5,903 (2024)Community: Winter Park Pines Merrie OaksSingle Family
Taxes:$5,903
Elementary School: Aloma Elem
Remarks: CALLING FOR HIGHEST AND BEST OFFERS BY MONDAY, APRIL 20th at 9:00 AM. Tucked away on a quiet street in the heart of Winter Park, this fully renovated 4-bedroom, 2.5-bath pool home—enhanced by fully owned solar panels—offers a rare blend of privacy, thoughtful design, and effortless indoor-outdoor living. Set on a generous ¼-acre lot, every detail has been curated to create a home that feels both elevated and family-friendly. Inside, the home opens to a flowing layout ideal for both everyday living and entertaining. Wide-plank luxury vinyl flooring, designer tile, and a soothing, modern palette create a cohesive sense of calm throughout. The kitchen is both a statement and a gathering place, featuring an oversized island wrapped in Taj Mahal quartzite, stainless steel appliances, and a custom wine bar—designed for connection, conversation, and celebration. Adjacent to the kitchen, the sunroom is a showstopper bathed in natural light and enhanced with custom built-ins, this versatile space effortlessly transforms into a home office, playroom, or entertainment lounge. This is where this home comes alive; perfect for large gatherings. The primary suite offers a serene retreat, highlighted by a fully remodeled spa-inspired bathroom with a soaking tub and a sleek, modern shower; inviting you to slow down and unwind. Outside, the newly added 800-square-foot turf play area, side yard, and green space surrounding the pool create room to play, entertain, and relax. The cul de sac and backyard feel exceptionally private, quiet, and peaceful. Just minutes from Park Avenue, you are surrounded by boutique shopping, acclaimed dining, lakeside strolls, and a lifestyle that feels both vibrant and relaxed. From morning coffee runs to evening walks under oak-lined streets, this is the essence of Winter Park living. This home is more than move-in ready—it’s a place to gather, grow and live. ROOF (OCT. 2022) HVAC (2017) WATER HEATER (2016) PLUMBING (2020) ELECTRICAL (UPDATED 2026) POOL PUMP/MOTOR (2020), POOL RESURFACED (2017) DRAIN SYSTEM: FRENCH DRAINS, SUMP PUMPS, GUTTERS (2024)
Listing Agent: Rebecca Bininger Junod (407-230-3650)
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