Location: Winter Park
Keyword(s): Glenridge Middle
Keyword(s) Middle School: Glenridge Middle
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7488 WHISPERWOOD DR #28, WINTER PARK, FL 32792
$220,00037 Days on yellowkey MLS ID: O6419151
REDUCED by $10,000 (4.3%) on 07/17/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1578 Built: 1974Monthly Fee: $575 Tax: $3,078 (2025)Community: Whisperwood CondoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,078
Elementary School: Cheney Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Glenridge Middle
Remarks: Rare Two-Story 2BR/2.5BA Condo with Two Private Suites in Winter Park. Highlights: Two-story floor plan condominium with a townhome-style layout, 2 spacious bedrooms, each with its own private ensuite bathroom, 2.5 bathrooms, Functional kitchen with stainless steel appliances, Open-concept living and dining area, Private fenced patio – perfect for relaxing, grilling, or entertaining, Covered parking plus additional guest parking, Community pool. The HOA covers exterior maintenance, roof, trash, landscaping and community pool, allowing owners to enjoy a low maintenance lifestyle. Why You'll Love It !! This well maintained townhome offers the perfect combination of comfort, convenience, and value. The bright, open floor plan is ideal for everyday living, while the two upstairs ensuite bedrooms provide privacy for homeowners, guests, or roommates. Enjoy your morning coffee or unwind in the evening on the private fenced patio—your own outdoor retreat. Prime Winter Park Location: Conveniently located just minutes from: Full Sail University, University of Central Florida (UCF), Downtown Winter Park, Major highways (417 & 408), Shopping, dining, parks, and entertainment Great Opportunity, Whether you're a first-time homebuyer, downsizing, or looking for an investment property, this home offers exceptional value in one of Central Florida's most convenient locations. Schedule your private showing today and discover everything this Winter Park townhome has to offer.
Listing is courtesy of: PARKVIEW REAL ESTATE (407-312-6472)
Listing Agent: Miranda Azer (407-312-6472)
1871 BARKER DR, WINTER PARK, FL 32789
$779,00014 Days on yellowkey MLS ID: O6425831
0 Days Off yellowkey (back on 7/24/2026)
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2231 Built: 1957 Tax: $8,858 (2025)Community: South Lakemont ShoresSpa: NoSingle Family
Taxes:$8,858
Elementary School: Baldwin Park Elementary
Remarks: Under contract-accepting backup offers. Rare Winter Park gem, nestled between Lake Baldwin and the heart of Winter Park. This fully refreshed, single-story home features brand-new interior and exterior paint, complemented by newly refreshed landscaping. Offering 3 bedrooms and 3 full bathrooms, the highly desirable split floor plan includes two primary suites. The main primary suite boasts an updated shower, vanity, and a spacious walk-in closet. The second suite features a garden tub with shower and its own walk-in closet. The updated kitchen is equipped with floor-to-ceiling cabinets for ample storage and a custom built-in kitchen nook with bench seating. Additional highlights include a cozy fireplace, laminate flooring, plantation shutters, an air-conditioned laundry room, and an incredible oversized 3-car garage. Enjoy Florida’s outdoor living year-round with a screened porch and a spacious, fully fenced backyard. Superb location under a half-mile to Baldwin Park, 2.5 miles to Park Avenue, and 3 miles to Rollins College. Zoned for highly rated Winter Park schools and situated just moments from the Lake Baldwin dog park.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Rikhil Amin (407-792-8069)
200 SAINT ANDREWS BLVD #2904, WINTER PARK, FL 32792
$230,0007 Days on yellowkey MLS ID: O6427536
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1219 Built: 1970Monthly Fee: $430 Tax: $3,519 (2025)Community: Four Seasons CondoCondo
Taxes:$3,519
Elementary School: Brookshire Elem
Remarks: WHAT A GEM! Tucked away in a private, sought after community and so conveniently located in breathtaking Winter Park. Here’s a beautifully maintained, upgraded and move-in ready home. With 2 large bedrooms and 1.5 bathrooms, this unit spans 1,219 square feet, providing an ideal space for cozy living. Enjoy the benefits of a peaceful and friendly community, with well-manicured grounds and a welcoming atmosphere. This charming home has been tastefully updated with upgraded laminate flooring, a renovated kitchen with granite countertops, newer cabinets and a stylish backsplash. The floor plan offers a dining & family room open combination which looks out on the porch and brings in plenty of natural light. Both nicely sized bedroom suites are on the second floor and have a shared & updated bathroom. Ample storage on the back patio for your bike and all your extra toys allowing you to enjoy your weekends. This is an extremely well managed community with an onsite manager taking pride in the community and care for their residents. Four Seasons community provides super amenities including a cubhouse with library, a renovated fitness center, 3 swimming pools, tennis courts, a laundry facility steps away and shuffleboard. Walk to Cady Way Park with tennis courts, baseball and soccer fields, playgrounds, community pool and Cady Way Trail. Minutes to Advent Health Winter Park Hospital, shopping on Park Avenue, Rollins College, Valencia, Full Sail and UCF. This pet friendly community and charming condo has everything you need! Great opportunity to own in FOUR SEASONS condominiums where LOCATION, LOCATION, LOCATION is prime!
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Sharon Mikol (407-963-3679)
708 BALMORAL RD, WINTER PARK, FL 32789
$1,690,00021 Days on yellowkey MLS ID: O6423883
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2786 Built: 1960 Tax: $6,459 (2025)Community: Kenilworth Shores Sec 06Spa: NoSingle Family
Taxes:$6,459
Remarks: A rare elevated corner lot in the heart of Winter Park — walkable to Park Avenue's boutique shops and restaurants, and set on one of the area's most desirable streets. Substantial homesite, prime location, endless potential. Coming soon. Reach out to the listing agent if you would like more information about the property.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Caitlin De Oliveira (407-267-7196)
2708 LION HEART RD, WINTER PARK, FL 32792
$614,500148 Days on yellowkey MLS ID: O6387685
REDUCED by $500 (0.1%) on 07/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1785 Built: 1963 Tax: $7,007 (2024)Community: Winter Park Pines RepSpa: NoSingle Family
Taxes:$7,007
Tax Year: 2024
Remarks: Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning two-tone kitchen is a true centerpiece, featuring sleek quartz countertops, contemporary finishes, and new appliances to be installed at closing—perfect for both everyday living and entertaining. The upgrades continue in the fully renovated bathrooms, where carefully selected color palettes and high-quality finishes provide a fresh, sophisticated look designed to stand the test of time. Every detail of this home has been meticulously considered, leaving no space untouched. Outdoors, enjoy your private oasis with a newly resurfaced pool—ideal for relaxing weekends or hosting gatherings year-round in Florida’s sunshine. This move-in-ready gem offers the perfect opportunity to own a like-new home in a highly desirable location. Come experience the beauty, quality, and lifestyle that 2708 Lion Heart Rd has to offer—your dream home awaits.
Listing is courtesy of: EQUITYPRO LLC (407-203-6860)
Listing Agent: Navid Rokh (321-900-5977)
2504 FORFARSHIRE DR, WINTER PARK, FL 32792
$630,00014 Days on yellowkey MLS ID: O6424656
0 Days Off yellowkey (back on 7/22/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1915 Built: 1962 Tax: $2,733 (2025)Community: Brookshire Heights 2Nd AddSingle Family
Taxes:$2,733
Remarks: RARE TWO-OWNER MID-CENTURY MODERN HOME IN WINTER PARK PROPER!! You will fall in love as the canopy of trees along Forfarshire Drive leads you to the door of this desirable Winter Park address. A fresh exterior re-envisioning brings a modern curb appeal, complete with a beautifully tiled covered front porch, glass entry door, Zen fountain and low architectural awnings provide an immediate sense of style and anticipation of what awaits inside the home. Upon entry, a large open living area with over-sized picture window and a stylish dining area, adorned with Brazilian hardwood flooring create a relaxed living experience. Updated kitchen includes white cabinetry (undermount counter lighting), Sile Stone countertops with undermount sink, stainless fridge & dishwasher and brush nickel hardware finishes. A large rear bonus room with storage closet space (designer built-ins) and oversized slider door leads to fenced and private backyard, the perfect retreat to relax and unwind. This wide-shoulder split floorplan offers a left-side primary bedroom with hardwood flooring and a large en suite office with access door to backyard, all wrapped windows with sophisticated Plantation shutters. The right side guest wing includes two large bedrooms flanking a remodeled full guest bathroom. KEY UPDATES INCLUDE: Architectural Shingle Roof (2016), Double Pane Windows (throughout), Knockdown Ceilings, Recessed LED Lighting & Touch Control Switches, PEX Plumbing, Interior Panel Box, Garage Opener. Walking distance from the finest amenities in the area: Cady Way Walking Trail, Ward Park, Winter Park Pines Golf Club and the area’s finest Winter Park School District (Brookshire Elementary, Glenridge Middle, Winter Park High). This home combines prestige and affordability in one irreplaceable address. See it before the opportunity has passed you by!!
Listing is courtesy of: RE/MAX CENTRAL REALTY (407-333-4400)
Listing Agent: Bill Miller (407-415-2263)
303 SCOTTSDALE SQ #303, WINTER PARK, FL 32792
$80,00020 Days on yellowkey MLS ID: O6424296
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1020 Built: 1974 Tax: $1,392 (2025)Community: Winter Park Woods CondoCondo
Taxes:$1,392
Remarks: Great location for homeowner or investor. Located close to FullSail and UCF and major roads, shopping, eating and more. Don't hesitate to see this one before it is gone!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Lisa Wright (321-231-3141)
2824 WOODSIDE AVE, WINTER PARK, FL 32789
$600,00022 Days on yellowkey MLS ID: O6423146
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 912 Built: 1952 Tax: $5,163 (2025)Community: Orangewood ParkSingle Family
Taxes:$5,163
Elementary School: Audubon Park K8
Remarks: Location, location, location. Wonderful home located in Winter Park besides Baldwin Park. Live in this home now - or purchase for the property and build your custom home! The yard is large. Large shed in the yard to store all of your yard essentials. You will love the area and the convenience to what makes this area special...steps from East End Market, lots of amazing restaurants, shopping, Leu Gardens, and so much more. Updates to the home include: Roof: 2020, HVAC 2019, Elecrical - new utility box, Plumbing: re-plumbed Kitchen and both bathrooms. Welcome Home.
Listing is courtesy of: PARKSIDE PROPERTIES, LLC (407-376-6635)
Listing Agent: Kristin Haughwout-Osorio (407-376-6635)
2948 ANTIQUE OAKS CIR #94, WINTER PARK, FL 32792
$150,000326 Days on yellowkey MLS ID: O6342254
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 749 Built: 1984Monthly Fee: $300 Tax: $1,831 (2024)Community: Parkview Village CondoCondo
Taxes:$1,831
Elementary School: Aloma Elem
Remarks: Welcome to this bright and cozy 1-bedroom, 1-bathroom corner unit located in the highly desirable Winter Park area of Orlando. This well-maintained condo features ceramic tile flooring throughout, a spacious walk-in closet in the master bedroom, a laundry closet with washer and dryer included, and modern light fixtures. Enjoy the outdoors on your very nice private balcony, and take advantage of private stairs from the outside entrance—a rare and convenient feature. Located in a beautifully kept community with easy access to shops, restaurants, and all of Winter Park's charm. Ideal as a first home, seasonal getaway, or investment opportunity!
Listing is courtesy of: THE PAMPAS REAL ESTATE GROUP, LLC. (561-234-7771)
Listing Agent: Santiago Silva (561-234-7771)
2715 PRINCE JOHN RD, WINTER PARK, FL 32792
$494,90052 Days on yellowkey MLS ID: O6415084
REDUCED by $4,000 (0.8%) on 07/22/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1565 Built: 1963 Tax: $7,101 (2025)Community: Winter Park Pines RepSingle Family
Taxes:$7,101
Remarks: GREAT HOME & GREAT VALUE — home needs cosmetic work and some TLC - if you DIY you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for BROOKSHIRE ELEMENTARY which is 3 blocks away. New roof (12/2021), New water heater (12/2021), Re-piped (1/2022, no polybutylene), New garage door and opener (2/2022), New AC evaporator coil (6/2022) and New French drain system (6/2023). The home has an irrigation system and irrigation well and New gutters (2/2022). OWNER FINANCING available for owners or flippers. All room dimensions must be independently verified by the buyer.
Listing is courtesy of: VIA PROPERTIES LLC (321-229-6085)
Listing Agent: Donna Peebles (321-229-6085)
263 SCOTTSDALE SQ #263, WINTER PARK, FL 32792
$80,00017 Days on yellowkey MLS ID: O6424619
1841 LAKE SPIER DRIVE, WINTER PARK, FL 32789
$1,595,00064 Days on yellowkey MLS ID: O6407841
REDUCED by $55,000 (3.3%) on 07/02/2026
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2467 Built: 1964 Tax: $4,844 (2025)Community: South Lakemont ShoresSpa: NoSingle Family
Taxes:$4,844
Remarks: Winter Park lakefront home! A rare opportunity to own a thoughtfully renovated mid century lakefront residence in Winter Park. This three bedroom four bath home offers stunning views, high ceilings and abundant natural light. The open layout flows effortlessly for everyday living and gatherings with friends and family. As you walk through the front door, you will be drawn to the large living area and a wall of windows and doors leading to the lake. The island kitchen is a cook's dream with abundant workspace and welcoming island seating. Imagine waking up every morning to yet another amazing view- The primary suite is spacious and private with newer bath and large walk- in closet. Nicely appointed secondary bedrooms and updated baths. In addition to the main living area, there is a separate oversized family room with a full bath adjacent. This home was completely renovated and expanded in 2013 creating a perfect blend of timeless architecture and carefully designed updates. Other features include two car garage with "glass" overhead doors and mini-split HVAC, metal roof, generous closets & storage throughout and recently installed sod. What makes this house truly special is the setting on Lake Spier- a ski lake tucked away in a secluded part of Old Winter Park . There are no homes across the lake- so spending time on the patio and dock offers an expansive view of water and trees and a remarkable sense of privacy. Inside and out, every space feels connected to the natural beauty. Great location to enjoy Winter Park living. Ideally situated near top rated schools - Baldwin Park, Glenridge and Winter Park High School. Enjoy close proximity to walking trails, restaurants and shopping. This home is truly special!
Listing Agent: Nicole Seybold (407-808-9374)
938 GOLFSIDE DR, WINTER PARK, FL 32792
$820,00014 Days on yellowkey MLS ID: O6425467
0 Days Off yellowkey (back on 7/21/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2366 Built: 1968 Tax: $5,917 (2025)Community: Golfside Sec 2Spa: NoSingle Family
Taxes:$5,917
Remarks: Under contract-accepting backup offers. **Due to the interest in the property, offers need to be in by Monday evening (7/20). ** Perfectly positioned on the 6th tee and 8th hole of the Winter Park Pines Golf Course, this home sits on an oversized quarter-acre lot and offers a rare opportunity to create your dream home while enjoying breathtaking golf course views. **The current floor plan features three bedrooms, as the original fourth bedroom has been converted into an expansive walk-in closet for the primary suite, and the flexible layout also offers the potential for a fifth bedroom.** While the interior offers an exciting opportunity to update, the sellers have already completed nearly $190,000 in major infrastructure and system improvements. One of the home's most valuable features is the fully paid-off solar panel system, which generates excess electricity that is returned to the utility company, resulting in an average monthly electric bill over 12 months is approximately $90. Additional capital improvements include a newer roof (2021), a new high-efficiency, variable-speed Lennox HVAC system (2025), a new energy-efficient, heat-pump water heater (2025), complete home repipe (2020), restoration of the cast-iron sewer system (2022) and plumbing stacks, upgraded attic insulation for enhanced energy efficiency (2023), a newer pool heater and pump (2024), added French drains (2025), new gutters with leaf guards, a deep irrigation well, an expanded circular paver driveway for ample parking space, and much more. Inside, the flexible floor plan offers endless possibilities. Beyond the spacious, front-facing living/dining room, the kitchen opens to a comfortable family room with a wood-burning fireplace. The kitchen window and pocket sliding glass doors frame beautiful views of the expansive covered lanai, screened pool, and rolling fairways beyond. The current 3-bedroom/2-bath layout on the left side can easily be reconfigured to restore the original 4th bedroom, which now serves as an oversized walk-in closet for the primary suite. The corner bedroom functions as both a guest room and home office, featuring a custom Murphy bed concealed behind a built-in bookcase, providing exceptional flexibility. On the opposite side of the home, an enormous bonus room with a full bath, offers direct pool access, and sweeping golf course views. Whether envisioned as a private guest suite or 5th bedroom, recreation room, home office, fitness studio, media room, or multigenerational living space, the bonus room has endless possibilities. Located just a few doors from the Cady Way Trail on one of the neighborhood's most picturesque oak-canopied streets, the setting is truly exceptional. This is a rare opportunity to purchase a home set directly on one of Winter Park's premier golf courses, where major mechanical system upgrades and costly infrastructure improvements have already been completed, creating the perfect opportunity to transform the interior into your own custom vision. Move in today, enjoy the exceptional location, and renovate at your own pace! Be sure to request a complete list of improvements, along with the floor plan, to fully appreciate the incredible potential this home presents.
Listing Agent: Marystuart Day (407-620-8683)
528 SAINT DUNSTAN WAY, WINTER PARK, FL 32792
$524,99050 Days on yellowkey MLS ID: O6414677
REDUCED by $10,010 (1.9%) on 07/11/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1656 Built: 1964 Tax: $6,000 (2025)Community: Winter Park PinesSingle Family
Taxes:$6,000
Remarks: Under contract-accepting backup offers. Welcome to Winter Park Pines, one of Winter Park's most desirable and established neighborhoods! Situated on nearly a quarter-acre lot, this beautifully maintained home with fresh interior paint combines modern updates, everyday comfort, and an unbeatable location. The stunning recently updated kitchen serves as the heart of the home, featuring stylish finishes and an inviting space for cooking, entertaining, and gathering. Throughout the home, you'll find attractive flooring with no carpet, offering both a clean, modern look and easy maintenance. Major improvements provide peace of mind, including a new roof and complete re-plumbing completed in 2023. The spacious lot offers plenty of room to enjoy outdoor living, gardening, pets, or future possibilities. Location is everything, and this home delivers. Just steps from Cady Way Pool and the popular Cady Way Trail, you'll enjoy easy access to recreation, fitness, and outdoor activities. Residents also love the convenient proximity to restaurants, shopping, parks, golf, and the charm of Downtown Winter Park. Best of all, there is no HOA, providing added flexibility and freedom. With significant recent updates, a generous lot, and a prime location in highly sought-after Winter Park Pines, this move-in-ready home is a wonderful opportunity to enjoy the very best of Winter Park living.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Jonathan Cole (407-928-9516)
3381 CEDAR SPRINGS PL #151, WINTER PARK, FL 32792
$179,90035 Days on yellowkey MLS ID: O6419959
0 Days Off yellowkey (back on 7/20/2026)
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1031 Built: 1984 Tax: $197 (2025)Community: Hidden. OaksSpa: NoCondo
Taxes:$197
Remarks: Under contract-accepting backup offers. Move right in and enjoy low-maintenance living in the desirable Hidden Oaks community of Winter Park. This meticulous maintained and nicely updated 2-bedroom, 2.5-bath townhome-style condo features two spacious primary suites, each with its own private en-suite bathroom, offering a flexible floor plan and exceptional functionality. The open and inviting layout includes an oversized great room, 12-inch ceramic tile flooring, and a well-appointed kitchen with maple cabinetry, Corian countertops, flat-top range, stainless steel refrigerator, and new microwave, new blinds throughout. The washer and dryer are included, making this home truly move-in ready. Both bathrooms have been tastefully updated, maple cabinetry, one with granite & one with Corian countertops for a cohesive, modern look. Enjoy outdoor living on the private rear patio, complete with space for grilling and an additional storage closet. Hidden Oaks is a beautifully maintained community featuring mature landscaping, a community pool, and a convenient Winter Park location near shopping, dining, entertainment, major employers, and highly rated Winter Park schools. The monthly condo fee includes water, sewer, trash, exterior maintenance, grounds maintenance, and community amenities, creating an easy lock-and-leave lifestyle. Conveniently located near Full Sail University, the University of Central Florida, Downtown Winter Park, and major roadways, this home offers an excellent opportunity for owner-occupants, those seeking a second home, or buyers looking for a long-term investment property. Don't miss the chance to own a well-maintained and move-in-ready home in one of Winter Park's most convenient locations.
Listing Agent: Alie Gattis (407-760-1488)
3019 ANTIQUE OAKS CIR #124, WINTER PARK, FL 32792
$142,500342 Days on yellowkey MLS ID: O6337083
REDUCED by $2,000 (1.4%) on 07/10/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 749 Built: 1984Monthly Fee: $300 Tax: $2,050 (2024)Community: Parkview VillageSpa: NoCondo
Taxes:$2,050
Remarks: PRICE IMPROVEMENT!! What better value! Accepting offers. Clean, Crisp and Fresh! Welcome home! NEWLY RENOVATED BATHROOM on deck. Is Winter Park your destination or desire? Investment Potential, Student Sanctuary or just a long-awaited life. Centrally located at your fingertips. Location, Lifestyle, Luxurious Zip Code, Friends, Culture and Community. Discover an unparalleled opportunity to own a piece of prime real estate in the heart of Winter Park, Florida. This beautifully appointed condo apartment is located within a vibrant, amenity-rich HOA community offering a perfect blend of convenience and value. Whether you're a first-time buyer, a savvy investor seeking strong rental return, a student prioritizing location and community or a loving and supportive parent wanting to be closer to your excelling child, this unit checks every box, all at an exceptional, reasonable price point. The very best luxury boutiques, fine dining, sidewalk cafes, and vibrant art festivals. Instant access to top tier schools and hospitals. Directly across from Full Sail University, minutes to Rollins College, UCF, Valencia College and major medical centers like AdventHealth and Orlando Health facilities, making it ideal for any resident, and or faculty. Transportation is easily accessible to Downtown Orlando where the famous Lake Eola Park is, Winter Springs, Oviedo, The Orlando International Airport, Cady Way Trail, biking, hiking, swimming, volleyball, pickleball, tennis and painting at The Crealde School of Art. There's just so much within reach. Explore local gatherings, social events and community connections. For all investors, strong rental income potential and appreciation value. There's low maintenance and worry-free ownership opportunities. Let's build a portfolio together or get you owning immediately. Let's get your private tour scheduled.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Cassandra Kelly Flores (347-723-4649)
1864 GRINNELL TER, WINTER PARK, FL 32789
$1,599,00090 Days on yellowkey MLS ID: O6403822
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3028 Built: 2006 Tax: $16,615 (2025)Community: FremarSpa: YesSingle Family
Taxes:$16,615
Remarks: Situated in the heart of Winter Park, this custom-built Mediterranean-style estate offers an exquisite living experience that marries timeless architecture with modern innovation. A dramatic grand foyer introduces a residence where every finish has been meticulously curated, from Turkish travertine stone and rich wood flooring to Brizo hardware in Brilliance Polished Gold. At the heart of the home, the chef’s kitchen blends elegance and function with gleaming stainless steel appliances, crisp white cabinetry, granite countertops, and a well-appointed Butler’s pantry with a dedicated bar, creating a sophisticated setting for effortless entertaining. Integrated smart features further elevate daily living, including an intercom system for seamless communication, electronic blackout curtains for instant privacy and ambiance, and thoughtful, layered lighting throughout. The magazine-worthy primary bath—featured in Florida Home—feels like a private spa retreat, with floor-to-ceiling back-lit mirrors, a self-cleaning smart toilet with bidet, a custom Barclay soaking tub with black matte exterior, and Calcutta gold marble countertops and backsplash. These luxe finishes are anchored by an oversized chevron pattern tile by Crossville in Ice White, a throwback diamond-pattern shower floor, and a sculptural Kuzco LED chandelier that completes the space with dramatic flair. Expansive living areas open to resort-inspired outdoor spaces where a heated saltwater pool and spa, private mini-golf green, and a summer kitchen with tongue-and-groove wood ceiling create a true indoor-outdoor sanctuary. Velux solar-powered skylights with acoustic rain sensors that automatically close at the first sign of rain, a Mosquito NIX misting system, comprehensive surveillance, and electronic private gated access provide both comfort and peace of mind. Natural gas service and a dedicated hook-up for a whole-house generator underscore the home’s emphasis on performance and preparedness. Crafted for those who expect uncompromising quality, this Winter Park residence is more than a home—it is a refined sanctuary where architectural presence, rich materiality, and thoughtful technology converge in one coveted address.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Robyn Brehne-Glass (407-474-4038)
2032 KIMBRACE PL, WINTER PARK, FL 32792
$1,888,88851 Days on yellowkey MLS ID: O6414862
REDUCED by $100,000 (5.0%) on 07/16/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3382 Built: 2021 Tax: $16,035 (2025)Community: Kenilworth Shores Sec 03Spa: YesSingle Family
Taxes:$16,035
Remarks: A PRIVATE RESORT-STYLE SANCTUARY IN THE HEART OF WINTER PARK 5 Bedrooms | 4 Bathrooms | 3,400+ SF|Saltwater Pool & Spa|Minutes to Park Avenue Welcome to a rare offering where luxury, tranquility, and architectural sophistication converge. Nestled in one of Winter Park's most desirable neighborhoods, just minutes from the boutiques, fine dining, and cultural attractions of Park Avenue, this custom Mid-Century Modern residence delivers an extraordinary lifestyle defined by elegance, wellness, and privacy. The home is within the acclaimed Winter Park school district, less than four miles from Trinity Preparatory School, and minutes from Rollins College and the University of Central Florida, placing premier educational opportunities nearby. Thoughtfully designed with a Zen-inspired aesthetic, the home blends clean architectural lines with warm natural elements to create a refined, restorative living experience. From the moment you arrive, a sense of calm surrounds you, offering a peaceful escape while remaining minutes from everything Winter Park offers. Inside, soaring 10-foot ceilings, expansive walls of glass, and wide-plank engineered hardwood flooring create bright, open living spaces filled with natural light. A semi-floating steel staircase with solid white oak treads serves as a dramatic focal point, while designer Restoration Hardware lighting adds warmth and sophistication throughout. The main living area was designed for entertaining. A Dimplex fireplace anchors the great room, complemented by a custom wine bar. At the heart of the home, the chef's kitchen showcases a waterfall island, premium quartz countertops, marble backsplash, double-stacked cabinetry, and a custom pantry. High-end Samsung smart appliances, including a Family Hub refrigerator, WiFi-enabled convection wall oven, Flex Duo cooking system, and 36-inch Bluetooth cooktop, complete this exceptional culinary space. A first-floor guest suite and full bath provide flexibility for visitors, a private executive office, fitness studio, or wellness retreat. The finished two-car garage features epoxy flooring and a modern glass garage door. Upstairs, the primary suite serves as a private sanctuary. The spa-inspired bath features a freestanding soaking tub, dual-entry marble shower with a semi-frameless glass enclosure, dual vanities, and a custom walk-in closet. Beyond the walls of the home lies your own private paradise. Professionally designed by Exotic Landscape Company, the resort-style outdoor living space evokes the serenity of a Balinese retreat. The newly constructed saltwater pool and spa showcase glass tile finishes, mini-pebble surfaces, travertine coping, LED lighting, therapy jets, a cascading waterfall, and smartphone-controlled OmniLogic automation. A custom outdoor stone shower, yoga platform, lush tropical landscaping, and curated hardscapes create an environment dedicated to relaxation and wellness. Additional features include Eufy smart lock technology, Arlo video doorbell, Google Nest thermostat, WiFi-enabled irrigation, smart garage controls, Quality Edge Vesta steel plank siding, and an expanded driveway. Less than ten minutes from Park Avenue, this exceptional residence offers a rare opportunity to own a home that feels more like a private luxury resort. More than a home, it is a sanctuary where timeless design, resort-inspired living, and one of Central Florida's finest educational settings create an unparalleled lifestyle.
Listing is courtesy of: SIMPLICITY: A RE BROKERAGE CO (407-920-6020)
Listing Agent: Robert Sassos (407-920-6020)
758 WARRENTON RD, WINTER PARK, FL 32792
$318,985120 Days on yellowkey MLS ID: O6395298
1 Days Off yellowkey (back on 7/16/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1196 Built: 1988Monthly Fee: $86 Tax: $3,689 (2025)Community: Winter Park Pines Patio HomesHalf Duplex
Taxes:$3,689
Remarks: HOME IS BACK ON THE MARKET AFTER GETTING A BRAND NEW ROOF!!! Tucked away on a quiet cul-de-sac in highly sought-after Winter Park, this beautifully updated three bedroom, two bathroom duplex offers the perfect blend of comfort, style, and location—just steps from Winter Park Pines Golf Club. Once inside you discover open living spaces featuring warm wood flooring throughout the living areas and bedrooms, complemented by vaulted ceilings in the main areas and ceiling fans that enhance the home’s airy feel. The BRAND-NEW kitchen has tile flooring and is not only functional, but beautiful showcasing classic shaker cabinets, sleek quartz countertops, and stainless steel appliances—perfect for both everyday living and entertaining. There are three nice sized bedrooms, all with large closets. The primary bedroom features sliding glass doors that lead directly to the large backyard and open patio. Both bathrooms have been renovated with modern finishes, including BRAND-NEW vanities, countertops, tub/showers, plus durable and stylish luxury vinyl plank flooring. Situated on a generously sized corner lot, the property offers plenty of outdoor space to enjoy, along with a charming paver front patio and the convenience of a one-car garage with opener. You will love the privacy of this end unit on the quiet cul-de-sac. Enjoy the ease of walking to nearby schools and being just moments from golf, shopping, dining, and all that Winter Park has to offer. With low HOA dues and located in a top-rated school district, this is an incredible opportunity in one of Central Florida’s most desirable neighborhoods.
Listing is courtesy of: SUN PROPERTIES, INC. (407-645-5700)
Listing Agent: Andrew Musashe (407-645-5700)
639 SAINT JOHNS CT #639, WINTER PARK, FL 32792
$194,90095 Days on yellowkey MLS ID: O6402025
0 Days Off yellowkey (back on 7/15/2026)
REDUCED by $5,000 (2.5%) on 06/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1981 Tax: $3,077 (2025)Community: Winter Park VillasCondo
Taxes:$3,077
Remarks: Under contract-accepting backup offers. Freshly painted 2 Bedroom/2 Bath townhouse-style condo with no neighbors above or below, backing up to a peaceful pond & community amenities. The upstairs/downstairs split-bedroom floor plan offers privacy - ideal for roommates or families. The bright living area features soaring cathedral ceilings, a corner fireplace, and access to a partially covered patio, perfect for entertaining or BBQs. There's abundant storage throughout, including coat, linen, patio, and under-stair space that could be converted into a small office or workout nook. The kitchen comes fully equipped with all appliances, ample cabinet space, and a breakfast bar, while the dining area overlooks the pond and opens to the patio with an additional storage closet. Upstairs, the primary suite includes an en-suite bath, a large walk-in closet, and corner windows that brings in great natural light. The second bedroom is located downstairs and offers dual closets and a ceiling fan. Updated luxury vinyl flooring runs through most of the home, and there is also an in-unit washer/dryer for convenience. Located in the highly desirable Winter Park Villas community, residents enjoy a wide array of amenities including a sparkling pool, clubhouse with fitness center, tennis courts, car wash station, scenic ponds, pet stations. The HOA provides exceptional value by covering roof & exterior maintenance, lawn service, water, trash, sewer, pest control—ensuring truly low-maintenance living. Conveniently located just minutes from Full Sail University, Rollins & Valencia Colleges, approximately 10 minutes from downtown Winter Park. Top-rated schools nearby, this property is an excellent opportunity for both homeowners & investors. Outdoor enthusiasts will also appreciate easy access to the nearby Cady Way Trail, perfect for walking, jogging, or cycling.
Listing is courtesy of: PLATINUM REALTY GROUP FLORIDA INC (407-270-7378)
Listing Agent: Adam Eisen (407-808-6967)
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