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$495,000
4 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. ?? Mid-Century Modern Gem in Sought-After Winter Park Pines Lovingly maintained and move-in ready, this Mid-Century Modern 4-bedroom, 2-bath home (just under 1,700 sq. ft.) offers light-filled living and timeless style in the heart of Winter Park Pines. Set beneath graceful mature oaks, the landscaped front yard provides a welcoming canopy. Step through the front door into a travertine-floored foyer overlooking the open living and dining areas — ideal for entertaining or relaxing in natural light. The modern kitchen features: Painted wood cabinetry, Granite countertops and stainless steel appliances (range, refrigerator, microwave, dishwasher, and wine fridge), Peninsula bar with prep sink for easy meal prep, French doors opening to the backyard. All four bedrooms feature ceiling fans and brand new textured carpet. The primary suite includes two closets and an updated marble-tiled bath. Enjoy the fully fenced backyard with garden space and irrigation system—perfect for pets, play, or quiet evenings under the trees. There’s also extra storage off the courtyard-entry carport, plus a pantry and coat closet for everyday convenience. Insulated, upgraded windows, Upgraded electrical service, Fresh paint throughout, New carpet and fixtures. The prime location is located just steps from Winter Park Pines Golf Course and minutes from Park Avenue, Winter Park Village, and Baldwin Park Town Center. Convenient to shopping, dining, and top-rated schools.

422 S Ranger Boulevard, Winter Park
$912,500
4 Beds ⋅ 3 Baths ⋅ Sanctuary At Lake Ann SubDv. ⋅ 32792 Zip Code
Welcome to 210 Laurel Park Court—a thoughtfully designed, single-story residence offering 4 bedrooms, 3 bathrooms, and a dedicated home office. Nestled on a ?-acre lot with a beautiful lake view of Lake Ann, this exquisite home is part of a private, gated enclave of just eight custom-built homes, perfectly situated close to everything you love about Winter Park living. Built by Arthur Rutenberg Homes and meticulously maintained, this residence showcases an array of upscale features designed for both comfort and luxury. Step inside to discover soaring ceilings, crown molding, and 18" neutral porcelain tile flooring, which together enhance the home’s open-concept design and timeless aesthetic. The formal living and dining rooms set the stage for elegant entertaining, while the spacious family room flows effortlessly into the kitchen and breakfast nook. The gourmet kitchen features a sleek gas cooktop, 42" solid wood cabinetry, and granite countertops—perfect for crafting culinary masterpieces. Natural light fills the open living areas, complemented by wood Bermuda shutters and integrated surround sound—ideal for both entertaining and everyday enjoyment. The primary suite is a serene retreat, offering direct lanai and pool access, his-and-hers walk-in closets, and a spa-inspired bathroom with a freestanding jetted Jacuzzi tub, glass shower enclosure, and dual vanities. This home has been thoughtfully updated for efficiency and peace of mind, featuring: Solar panels (2020) for reduced energy costs New A/C systems – condenser (2023) and air handler (2025) New hot water heater (2023) New washer & dryer (2022) Relax in the inviting living area centered around a stylish gas fireplace, or step outside to enjoy the beautiful pool and spa area—a private haven perfect for alfresco dining and leisurely afternoons. Each spacious bedroom has been designed to provide a peaceful sanctuary, while the landscaped yard adds to the home’s curb appeal and outdoor enjoyment. Ideally located just minutes from Winter Park’s boutiques, fine dining, cultural attractions, and top-rated schools, 210 Laurel Park Court offers an unparalleled blend of luxury, convenience, and modern efficiency. Experience the lifestyle you’ve always dreamed of in this exquisite home. (A one-time HOA capital contribution of $1,000 is required at closing.)

210 Laurel Park Court, Winter Park
$505,000
4 Beds ⋅ 2 Baths ⋅ Tamarak SubDv. ⋅ 32792 Zip Code
Welcome to this charming 4 bedroom, 2 bath home located in the desirable Charter Oaks subdivision of Winter Park. The centrally located kitchen features stainless steel appliances, granite countertops, and a breakfast bar that seamlessly connects to the family room. Enjoy cozy evenings by the wood burning fireplace or host gatherings in the separate dining room and spacious living room. Step outside to your own private retreat with a fully fenced yard and a covered screened patio with pool, perfect for year round entertaining and relaxation. This home also includes fully owned solar panels offering energy efficiency and reduced utility costs. Nestled in a quiet tree lined neighborhood with no HOA, this home provides the perfect balance of peace and convenience. You will be just minutes from Park Avenue, boutique shopping, world class dining, and the scenic Winter Park Chain of Lakes. Families will appreciate access to top rated schools, nearby parks, and recreational opportunities. With easy access to major highways and a short drive to downtown Orlando, this location simply cannot be beat.

1691 Bomi Circle, Winter Park
$660,000
4 Beds ⋅ 3 Baths ⋅ Lake Waunatta Woods SubDv. ⋅ 32792 Zip Code
Beautifully updated Winter Park home showcasing fifteen years of thoughtful renovations and “forever-home” quality throughout. Sited on just over 1/4 acre of manicured grounds, the inviting single level layout wraps around a bright, vaulted great room with tongue-and-groove ceiling, exposed central beam, and a stunning 20-foot folding Origin door system that opens fully to the pool and patio for seamless indoor-outdoor living. The expansive and private primary suite features a newly remodeled bath with timeless finishes as well as a surprisingly large walk-in closet. Three additional bedrooms and one-and-a-half baths are located on the opposite wing of the home, all connecting to the great room via French doors that create both openness and privacy. Multiple living spaces spotlight cozy vignettes at every turn - from the wood burning fireplace in the family room to the bright view out to the pool from the dining room; even the laundry room is outfitted with a gorgeous molded counter top sink and designer lighting! Notable systems upgrades include a new Trane variable-speed HVAC (2024), roof (2018), windows (2021), driveway (2024), pool pump and filter (2025), and spray-foam insulation. Distinctive details—custom brickwork, wood-inlaid eaves, solid core doors with top shelf hardware, detailed window casings and smooth-finish walls—add character and craftsmanship. Set in a quiet neighborhood near Lake Waunatta with easy access to University Boulevard, this home offers exceptional quality, comfort, and turnkey functionality in desirable Winter Park. Don't miss your chance to see it before its gone.

4019 Quenita Drive, Winter Park
$506,500
4 Beds ⋅ 2 Baths ⋅ Enclave At Aloma SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome to Enclave at Aloma — a gated Winter Park community known for its peaceful setting and unbeatable convenience. This spacious 4 bedroom, 2 bathroom home sits proudly on an expansive corner lot with no direct rear neighbors, offering extra space, privacy, and plenty of curb appeal. Step inside to find a bright, open layout with hardwood floors throughout the main living areas, updated light fixtures, and an airy feel that immediately feels like home. The kitchen features white cabinetry, granite countertops, stainless steel appliances, a walk-in pantry, and a center island with pendant lighting — all overlooking the dining and living areas covered in natural light. The primary suite is privately tucked away at the back of the home and features sliding glass doors leading directly to the expansive screened lanai, creating a seamless indoor-outdoor retreat. The en-suite bath includes dual vanities, a walk-in shower, and a generous walk-in closet. Two secondary bedrooms share a hall bath, while the third guest bedroom offers flexibility for a home office or playroom. Outside, enjoy the fully fenced backyard — ideal for entertaining or gardening. Additional highlights include a two-car garage and inside laundry room with built-in cabinetry. Zoned for highly rated Seminole County schools and neighboring the prestigious Trinity Preparatory School campus — known for its #1 STEM program in the Orlando/Winter Park area — this home is also just minutes from 417, 436, Downtown Winter Park shopping, dining, and more. Don’t miss the opportunity to own this upgraded, move-in-ready home. Schedule your private showing today!

8162 Lazy Bear Lane, Winter Park
$528,000
4 Beds ⋅ 2 Baths ⋅ Wrenwood Heights SubDv. ⋅ 32792 Zip Code
Experience the perfect blend of modern luxury and timeless charm in this newly renovated 4-bedroom, 2-bath Winter Park retreat. Thoughtfully designed with an open-concept layout, this home features sun-filled living spaces, a beautifully appointed kitchen with premium finishes, and a generous great room ideal for entertaining. A versatile spacious sunroom bridges indoor and outdoor living, offering the perfect spot for a home office, gym, or relaxation lounge as it opens to the backyard oasis. Outside, lush landscaping frames a large inground pool and expansive patio—an idyllic setting for gatherings or peaceful retreat. Just minutes from Park Avenue, top-rated schools, and Winter Park’s vibrant dining and shopping, this home captures the essence of Central Florida living at its finest. New roof installed 09/2025, Pool resurfaced 09/2025.

4991 Tangerine Avenue, Winter Park
$458,000
4 Beds ⋅ 3 Baths ⋅ Bel-Aire Pines, Unit Two SubDv. ⋅ 32792 Zip Code
Virtually Staged. Stunning Two-Floor Home in Coveted Winter Park School District Immaculately maintained and truly move-in ready, this unique two-story residence features distinct living quarters with private entrances to both levels. The main floor offers a spacious split-bedroom layout with three bedrooms and two full baths, including a primary suite with an en-suite bathroom and generous walk-in closet. The fully equipped kitchen boasts newer appliances and opens to a bright living area. The expansive 800 sq. ft. upper level functions as a self-contained living unit, ideal for multi-generational arrangements, home offices, or rental income potential. This versatile space includes one bedroom, a full bathroom, a private balcony, and a full open-concept living and dining area complete with a full-size refrigerator and stove. Located in the highly rated Winter Park School District, this home offers the perfect blend of top-tier education and Central Florida lifestyle. Residents enjoy easy access to world-class entertainment, situated just 26 miles (approx. 35 minutes) from Walt Disney World. Additional features include a large two-car garage with washer/dryer hookups, ample driveway parking, fresh interior paint, and a brand-new roof with a transferrable warranty. All major systems are well-maintained and in excellent working condition.

3312 Heartwood Avenue, Winter Park
$365,000
4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code
Welcome Home to Eastbrook in Winter Park! This beautifully maintained 4-bedroom, 2-bath home offers the perfect blend of comfort, charm, and modern updates — all nestled on an OVERSIZED CORNER LOT in the desirable Eastbrook community with NO HOA and NO CDD. Step inside to find 1,530 sq ft of thoughtfully designed living space, freshly painted in 2025 to give every room a bright, inviting feel. The renovated primary bathroom shower (2025) adds a touch of luxury, while the repiped plumbing (2024) comes with a transferable 30-year warranty for peace of mind. Enjoy outdoor living at its best with a brand-new fence and paved driveway (2023). Major updates have already been taken care of, including a new HVAC (2021), new water heater (2023), and a 9-year-old roof, ensuring this home is move-in ready and worry-free. You’ll love the convenient location — just 10 minutes to Downtown Winter Park and 15 minutes to Baldwin Park, putting shopping, dining, and local charm right at your fingertips. Located in the heart of Winter Park, Eastbrook is known for its welcoming vibe, tree-lined streets, and proximity to top-rated schools, parks, and more. Whether you're a first-time buyer or simply ready for your next chapter, this home has everything you’ve been looking for — style, updates, and location all in one!

1083 Eastbrook Boulevard, Winter Park
$699,450
4 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
**Multiple offers received*** Please submit highest and best by 10/20/2025 at 4:00 pm This beautifully maintained golf course home offers effortless living in an established Winter Park neighborhood. As you drive along the charming tree-lined streets, the home greets you with impeccable landscaping and timeless curb appeal. Step inside the foyer and discover a bright, open floor plan that seamlessly connects the dining area, kitchen, and living room. Soft natural finishes create a breezy, relaxed feel, while the cozy fireplace anchors the living space, which is perfect for gathering with loved ones. The kitchen is both stylish and functional, featuring stainless steel appliances, stone countertops, a farmhouse sink, and refinished cabinetry. The stylish island provides casual dine-in seating, and the custom pantry and laundry room offer exceptional storage, plus a convenient folding counter and hanging space. Your private primary suite is tucked away to the left of the kitchen, offering serene views and sliding doors that open to the screened lanai overlooking lush, mature landscaping. The walk-in closet provides generous storage, and the updated ensuite bath includes a walk-in shower with both handheld and fixed showerheads. A split floor plan offers three additional bedrooms and an updated guest bath with a tub and glass enclosure perfect for guests. Relax on the screened lanai and enjoy peaceful golf course views and privacy. The brand-new roof provides peace of mind, and the widened paver driveway offers both style and convenience. The garage is equipped with a workbench and built-in shelving for all your storage needs, plus an additional shed and fenced side yard create more outdoor space to enjoy. Located within the Winter Park school district, this home offers the perfect blend of privacy and convenience — just 8 minutes from Lake Baldwin Park, 10 minutes to Corrine Drive’s shopping and dining, 12 minutes to Park Avenue, and 20 minutes to Downtown Orlando.

1346 Golfside Drive, Winter Park
$627,000
4 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 03 SubDv. ⋅ 32792 Zip Code
One or more photo(s) has been virtually staged. Income-Producing Opportunity! Welcome to this versatile Winter Park POOL HOME! At present, this property is split into two separate living quarters with the main house offering 3 bedrooms & 2 bathrooms and the adjoining guest suite offering 1 bedroom & 1 bathroom. Each living quarter has its own kitchen, laundry, climate control & outdoor living space. Rent out the guest suite, share an address with an independent someone, or use the adjoining door to make one fluid space. There are tile floors throughout all areas and a 2-car carport with long driveway in front of both front doors. The heated, chlorine pool is nestled inside a fenced backyard and can be accessed by both living quarters; however, there is an outdoor retractable privacy divider to separate the outdoor spaces if so wished. The property holds 2 sheds; the larger, cottage-style shed is fully powered and insulated, and has a shelving unit on a swing hinge to create a bar at the shed’s double doors for outdoor entertaining. The propane firepit stays and is ready for your housewarming party! Notable updates include 2019 ROOF, 2022 main house A/C, 2024 pool pump & filter, 2025 pool heater. This home has been repiped, rewired, and has updated windows. A breaker box expansion was completed to provide power to the pool heater & cottage shed. The guest suite has a built-in mini split a/c, dehumidifier, water filtration under the kitchen sink & a murphy bed plus armoire storage which will stay. This corner lot property proudly stands a quarter mile to Ward Park and slightly over a mile to Lake Baldwin Park for a sample of the city’s plentiful recreation opportunities. Come explore this opportunity before it’s gone!

428 Selkirk Drive, Winter Park
$660,000
4 Beds ⋅ 2 Baths ⋅ Williamsburg SubDv. ⋅ 32792 Zip Code
Welcome to this well-maintained Winter Park home, proudly cared for by its original owner. With a BRAND NEW ROOF and BRAND NEW AC system, this property combines peace of mind with long-term value. Set on a spacious quarter-acre lot with NO HOA, it offers flexibility, privacy, and convenience in one of Central Florida’s most desirable locations. This home features a durable roof with a 10-year transferable warranty, engineered to withstand winds of up to 130 mph for lasting protection and peace of mind. Step inside through the front entry into a light-filled formal living room, where large windows set a warm and welcoming tone. Just to the right, the formal dining room provides the perfect space for family gatherings or entertaining. Flowing naturally into the main family room, you’ll find a cozy fireplace that anchors the space and creates an inviting setting for everyday living. The kitchen is designed for function with all appliances included, ample counter space, and a thoughtful connection to the laundry room, which features generous storage and everyday convenience. Off the family room, the Florida room is bright and versatile—ideal for a home office, reading nook, or playroom. One of the standout features is the expansive 483 sq. ft. bonus room, offering endless possibilities as a game room, studio, or additional living space to suit your lifestyle. Outdoors, a screened-in porch overlooks the fenced backyard, providing a comfortable spot to relax, garden, or host gatherings. An included shed adds extra storage for tools and equipment. Each bedroom is well-sized, offering comfort and practicality, with bathrooms that have been cared for and maintained with attention to detail. The thoughtful layout balances privacy and community spaces, making it both functional and inviting. Location is key, and this home delivers. Just a few minutes’ walk takes you to the scenic Cady Way Trail, Winter Park Pines Golf Course, and Winter Park High School. Nearby parks, shopping, dining, and top-rated schools add to the convenience, while downtown Winter Park, Orlando attractions, and major highways are only a short drive away. Perfect for buyers seeking a primary residence, an Orlando relocation home, or a smart Central Florida real estate investment, this property is a rare find. With only one owner since construction and NEW major systems in place, this Winter Park gem is ready for its next chapter. Contact us today for a private tour or more details on this exceptional opportunity.

2421 Summerfield Road, Winter Park
$899,000
4 Beds ⋅ 3 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
Discover elevated living in this stunning 4 bedroom, 2.5 bathroom pool home, perfectly situated overlooking a tranquil pond and Winter Park 18 hole golf course. Surrounded by a lush tropical backyard oasis, this residence blends modern sophistication with effortless comfort, creating a serene retreat that’s ideal for that perfect start to the morning with a cup of coffee or a relaxing wind down at sunset with a glass of wine. Inside, vaulted wood-trimmed ceilings and a wood-burning fireplace set a warm, inviting tone across 2,455 sq. ft. of thoughtfully designed space. The kitchen features contemporary cabinetry paired with quartz and butcher block wood countertops and a designer tile backsplash. Stainless steel appliances, including a beverage refrigerator, add a professional touch, while a built-in banquette provides seating for six—perfect for entertaining and everyday living. The primary suite offers wood floors, a walk-in closet, and a spa-like bath with dual floating vanity, soaking tub, and seamless glass shower. Enjoy outdoor living at its finest with pergola-covered sitting areas, outdoor shower, fire pit, and sparkling pool. Situated on a private tree-lined cul-de-sac, this home is located in a prime location just minutes from Cady Way Trail, Cady Way pool & courts, Winter Park Pines Golf Course, Crosby Center for Health and Wellbeing, Ward Park, Showalter Athletic Complex, Advent Health Winter Park Hospital and less than 10 minutes to Historic Park Avenue fine dining and shopping. Don’t miss your chance to own this rare Winter Park gem—schedule your showing today! ROOF - 2016 HVAC - 2023(2) PLUMBING - 2020 ELECTRICAL - 2021 WATER HEATER - 2020

1648 Cypress Point Lane, Winter Park
$500,000
4 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Winter Park “Love Shack No More” – 4 Bedrooms, 2 Baths, and Plenty of Potential! When they said “happily ever after,” they didn’t mention drywall dust and half-finished projects! This 4-bedroom, 2-bath home in highly sought-after Winter Park comes straight from a divorce split, which means one lucky buyer gets the rare chance to finish what love couldn’t — a home with solid bones and serious potential. Some renovations are already underway — think new finishes, updated spaces, and the kind of promise that makes HGTV jealous — while a few projects are still waiting for someone handy (or just brave) enough to see them through. Set on a quiet street close to top-rated schools, charming boutiques, and Winter Park’s favorite restaurants, this property is ideal for anyone who can look past a little sawdust and see the dream beneath. Whether you’re a renovator, a romantic, or just someone who loves a good comeback story, this is your chance to turn “it’s complicated” into “move-in ready.” Sold As-Is — because closure never looked so good.

2758 Sandwell Drive, Winter Park
$415,000
4 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code
BACK ON THE MARKET AND PRICED BELOW MARKET IN DESIRABLE TANGLEWOOD WINTER PARK COMMUNITY WITH NO HOA! ALLOWS SHORT TERM RENTALS (STR). LOW TAX DISTRICT. This is probably the closet you can get to Winter Park (Park Ave) without having to pay the Winter Park taxes or conform to their restrictions! This property has been extremely well maintained and would be an amazing home for a new family. ROOF IS 2023! All systems have been updated or serviced. Property features include 4 BEDROOMS, 2 BATHROOMS, 1,725 TOTAL SQFT, ATTACHED IN-LAW SUITE WITH ITS' OWN ENTRY, HUGE BACK YARD WITH LOT SITTING ON APPROX. 10,000 SQFT, TILE THROUGHOUT, STAINLESS APPLIANCES INCLUDED, FENCED, AND MORE. Seller is willing to give $5,000 credit towards the buyer's closing costs or buying down their interest rate (inquire about conditions). *More than one of the photos has been virtually staged.

1816 Ivy Lane, Winter Park
$625,000
4 Beds ⋅ 3 Baths ⋅ Enclave At Aloma SubDv. ⋅ 32792 Zip Code
Welcome to 7888 Pleasant Pine Circle, a stunning 4-bedroom, 2.5-bathroom pool home located in the highly sought-after gated community of Enclave at Aloma in Winter Park, FL. This meticulously maintained two-story home offers 2,267 square feet of beautifully designed living space. Step through the inviting entryway into a formal living room featuring stylish shiplap accents and luxury vinyl plank flooring that flows throughout the first floor. The open-concept layout connects the spacious family room—complete with serene views of your private pool and patio—to the dining area and an exquisite chef’s kitchen. The kitchen is a dream come true, boasting a large center island, stainless steel appliances, and sleek cabinetry and countertops. French doors lead to your private backyard oasis with a fully fenced yard and sparkling pool, perfect for Florida living. A convenient half bath is also located on the main floor for guests. Upstairs, the luxurious primary suite features a large ensuite bathroom with double vanities, a generous walk-in shower, and a massive walk-in closet. Bedrooms 2 through 4 share a well-appointed guest bathroom, and the spacious bonus/media room is ideal for a game room or home theater. This home combines style, functionality, and location. Just minutes from 417 & 436, you’ll enjoy close proximity to Target, Costco, and a variety of dining and shopping options. Zoned for top-rated Seminole County schools and neighboring the prestigious Trinity Preparatory School—renowned for its #1 STEM program in the Orlando/Winter Park area. Don’t miss this rare opportunity to own in one of Winter Park’s most desirable communities!

7888 Pleasant Pine Circle, Winter Park
$450,000
4 Beds ⋅ 2 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code
PRICE IMPROVEMENT! INCREDIBLE OPPORTUNITY! 5.75% ASSUMABLE MORTGAGE Interest Rate Available, making it an excellent opportunity for qualified Buyers. Welcome to 1422 Tierra Circle, beautifully refreshed immaculate pool home located in the well-established community of Casa Aloma, featuring 4 bedrooms, 2 full bathrooms and open floor plan. You will notice the enhanced curb appeal from the moment you arrive with newly painted exterior and driveway along with lush landscaping, creating a warm and inviting first impression. Many wonderful upgrades include a newer roof (2020), new electrical panel (2025), HVAC system (2022), HVAC/ air ducts cleaned and sanitized (2025), screened backyard patio (2023), new pavers and exterior shutters for added curb appeal, updated light fixtures, beautiful new front exterior door, new pool pump and luxury vinyl and carpet flooring (2022). The spacious living room flows into a versatile bonus area, both with excellent backyard pool views from the large window and sliding doors, allowing natural sunlight in. The bonus area is currently used as a playroom and ideal for an office space, library, bar or reading nook, leading to the kitchen. The kitchen is a chef’s delight, with stainless steel appliances, a gas stove and granite countertops, overlooking the dining room and sliding doors that open to the spacious screened patio and fenced backyard paradise. The large primary suite offers a peaceful retreat with double his-and-her closets and private ensuite bath, while three additional bedrooms provide flexibility for family, guests, or work-from-home needs. Step outside and enjoy true Florida living in your private backyard paradise, with a spacious screened patio, freshly painted pool deck, sparkling pool and an abundance of fruit trees, including limes, avocados, bananas, guavas, and mangos, perfect for entertaining or simply relaxing in the sunshine while enjoying fresh produce right at home. EXCELLENT LOCATION zoned for top-rated schools, minutes away from AdventHealth, Full Sail University, FL-436, and endless shopping and restaurants nearby. Come take a tour of this immaculate 4 bedrooms, 2 bathrooms immaculate pool home today!

1422 Tierra Circle, Winter Park
$330,000
4 Beds ⋅ 2 Baths ⋅ Springview SubDv. ⋅ 32792 Zip Code
Discover this spacious 4-bedroom, 2-bath BLOCK home situated on a generous QUARTER ACRE LOT lot with NO HOA—offering you the freedom to truly make it your own. Nestled in the heart of Seminole County, this home sits just minutes from Lake Howell High School, UCF, 417, and all the shopping and dining you could want. Inside, you'll find a bright and functional layout perfect for families, roommates, or first-time buyers looking for room to grow. The backyard offers space for a garden, pets, or future expansion—and with a NEW ROOF, the possibilities are endless. Zoned for TOP-RATED SEMINOLE COUNTY SCHOOLS and ideally located for commuters and students alike, this property is a rare opportunity in a rapidly growing area. Don’t miss your chance to put down roots in one of Central Florida’s most convenient and desirable neighborhoods. Schedule your private tour today!

3041 Dikewood Court, Winter Park
$569,990
4 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 03 SubDv. ⋅ 32792 Zip Code
Welcome to your dream home in the heart of Winter Park! Nestled in a quiet and sought-after neighborhood, this beautifully maintained 4-bedroom, 2-bathroom pool home offers 1,889 square feet of comfortable living space and the perfect blend of privacy and convenience. Backing directly to the prestigious Interlachen Golf Course, you'll enjoy peaceful views with no rear neighbors — a rare find in such a prime location. Step inside to discover spacious living areas, an updated kitchen, and plenty of natural light throughout. The 2-car garage provides ample storage, while the home's layout offers both functionality and flow, making it ideal for everyday living and entertaining. Each of the four bedrooms is generously sized, and the two bathrooms are tastefully appointed, offering both style and comfort. Outside, the backyard is a true oasis. Lush, mature landscaping surrounds the sparkling pool, creating a serene and private retreat perfect for relaxing or hosting gatherings. Whether you're enjoying a morning coffee poolside or an evening under the stars, this outdoor space is a showstopper. All of this is just minutes from charming Park Avenue and vibrant downtown Winter Park, with shopping, dining, and entertainment right at your fingertips. Don’t miss this rare opportunity to own a slice of paradise in one of Central Florida’s most desirable communities! ROOF - 2020 AC - 2025

1561 Nottingham Drive, Winter Park
$447,500
4 Beds ⋅ 2 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code
Lower Your Monthly Payment in Winter Park - Orlando! Discover this spacious 2,200 sf, 4-bedroom, 2-bath, 2-car garage, pool home in Casa Aloma—one of Winter Park’s most walkable, established neighborhoods—now available with special financing options to help you secure a lower interest rate. This expanded floor plan offers plenty of flexibility for work, play, and entertaining. Step outside to your own backyard retreat featuring a sparkling pool, screened patio, and tropical palm landscaping. Open-concept layout, cozy fireplace, and oversized lot make this home move-in ready. Located in a quiet, friendly community with optional $20 HOA, Flood Zone X (no flood insurance required), and easy access to the Universal-Disney phenomena, museums, science centers, botanical gardens, top-rated Seminole County schools, shopping, dining, and major highways—you can settle in with confidence. Here is the opportunity for a reduced rate. Schedule today and discover how you can secure comfort, space, and greater affordability in Winter Park!

1339 Monte Lane, Winter Park
$896,628
4 Beds ⋅ 4 Baths ⋅ Tucks Knoll SubDv. ⋅ 32792 Zip Code
Welcome to Tucks Knoll in Winter Park! Nestled on over FOUR ACRES at the end of a private cul-de-sac, this exceptional 4-bedroom, 4-bathroom residence offers more than 3,300 square feet of luxurious living space and a lifestyle that feels like your own private retreat. Backing up to a lush CONSERVATION area with the peaceful flow of Howell Creek, the property is surrounded by mature trees, vibrant landscaping, and natural beauty at every turn. The thoughtfully designed three-way split floor plan seamlessly balances entertaining with private comfort. Sun-filled formal living and dining rooms set a graceful tone, while the expansive great room with hardwood floors opens to the gourmet eat-in kitchen, complete with granite countertops, stainless steel appliances, a gas cooktop, tile backsplash, and a large pantry. A dedicated office with a bay window provides a quiet space to work, while the elegant primary suite impresses with cathedral ceilings, and a spa-inspired bath featuring dual vanities, a garden tub, and a spacious tile shower. Grand sliding pocket doors off of the family room lead to an expansive wood deck, the perfect setting to enjoy serene mornings and peaceful evenings surrounded by nature. Upstairs is a dedicated state of the art THEATER ROOM with comfy leather seats and surround sound elevating family fun, There is even a FULL BATH. The main level additional bedrooms include a Jack-and-Jill setup and a private suite with a walk-in closet. The backyard is a true showpiece—meticulously landscaped and thoughtfully planned. FRUIT TREES including ORANGE and FIG provide seasonal delights, while a beautifully maintained tiered garden bed produces sweet peppers, chives, and strawberries. Raised beds add even more bounty, offering eggplant and sweet potatoes. A large, level green space and a nicely CLEARED PATH to the creek invite both relaxation and exploration, creating an outdoor paradise that feels worlds away yet remains minutes from top-rated schools, shopping, and dining. This is more than a home—it’s a one-of-a-kind sanctuary blending privacy, nature, and convenience. Don’t miss the opportunity to make it yours. Schedule your tour today!

3870 Tucks Point, Winter Park
$550,000
4 Beds ⋅ 3 Baths ⋅ Enclave At Aloma SubDv. ⋅ 32792 Zip Code
Located in the gated community of Enclave at Aloma, this immaculate 4-bedroom / 2.5-bath home impresses with a functional, 3-way split bedroom floorplan, screened rear lanai, and an additional sitting area/flex space off the Primary bedroom with (2) additional built-in closets that truly sets this home apart. Meticulously maintained, this fabulous home features tons of post-build upgrades and improvements, including a fully landscaped property with a private, fenced backyard, engineered hardwood flooring, plantation shutters, upgraded light fixtures and ceiling fans, and bright, neutral interior paint for a fresh and airy feel throughout. Enter to a cozy foyer that welcomes you with gorgeous, rich engineered hardwood floors, leading past a convenient powder bath and into the large living space at the rear of the home where a spacious kitchen/living/dining combo makes entertaining a breeze. The open kitchen features granite countertops and stainless steel appliances, with a newer (2023) GE refrigerator and upgraded Bosch dishwasher, plus a walk-in pantry, and an island with a breakfast bar for added seating & prep space. Large windows with timeless plantation shutters line the rear wall, framing views of the Magnolia trees and lush backyard, while French doors off the dining area offer easy access to the screened rear lanai for outdoor lounging. The large Primary Suite extends to include an extra sitting room, with access to the screened lanai and (2) additional built-in closets that make it perfect for a quiet office space or dressing area. The en-suite Primary bathroom offers a modern stone countertop with dual sinks, plus a private water closet, linen closet, and a large walk-in closet. Just left of the front foyer sits 2 secondary bedrooms and a full hall bath, and to the right you’ll find the 4th bedroom, great for guests or a private office, and a laundry room with an upgraded front-loading washer and dryer, built-in upper cabinets, and a pull-out drying rack. The 2-car garage with a handy utility sink is accessible off the foyer. Experience the perfect blend of privacy and convenience in this gated community, just minutes from 417 & 436, and around the corner from Target, Costco, and numerous shops and restaurants. Ask for a floorplan and list of improvements!

7864 Pleasant Pine Circle, Winter Park
$450,000
4 Beds ⋅ 3 Baths ⋅ Country Lane SubDv. ⋅ 32792 Zip Code
4 Bedrooms | 2.5 Baths | New Roof | Winter Park’s Country Lane Welcome to this well-cared-for 4-bedroom, 2.5-bath home in the highly desirable Country Lane neighborhood of Winter Park! On the first floor, you’ll find a bright and inviting layout with a kitchen featuring stainless steel appliances, along with ample cabinet and counter space. There’s plenty of room to entertain, with a formal living and dining area on one side and a dinette and family room on the other. Major updates bring peace of mind, including a brand-new roof (2025) with solar panels for energy efficiency, plus fresh new sod that enhances the curb appeal. Upstairs, all four bedrooms are located together, creating a private retreat away from the main living areas. The highlight is the large primary suite, complete with a spacious walk-in closet, offering both comfort and convenience. Living here means more than just a home—you’ll enjoy the fantastic Country Lane community amenities. As a resident, you’ll have exclusive access to Lakeside Park on Lake Florence, featuring a fishing pier, kayak and paddle board launch, playground, and tennis courts. It’s the perfect setting for both relaxation and an active Florida lifestyle. Don’t miss this opportunity to own a move-in-ready home in one of Winter Park’s most loved neighborhoods!

1660 Tremont Lane, Winter Park
$749,900
4 Beds ⋅ 4 Baths ⋅ Landings At Hawks Crest SubDv. ⋅ 32792 Zip Code
Stunning 4-Bedroom Taylor Morrison Home in a Premier Winter Park Community! Welcome to this beautifully appointed 4-bedroom, 3.5-bath, 2,582 sq. ft., nestled in one of Winter Park’s most desirable gated communities with resort-style amenities. Built just 4 years ago, this residence blends modern elegance with comfort and convenience. Step inside to find an open-concept design with luxury vinyl plank flooring throughout the main living areas and a gourmet kitchen featuring GE Café Series appliances, SS vent hood and an oversized quartz countertop with plenty of space for entertaining. A dedicated home office makes working from home effortless, while the upstairs loft and expansive media room offer flexible space for relaxation or play. The owner’s suite includes a spa-like bath and a custom built-in shelving system in the walk-in closet. Additional highlights include tile flooring in select areas, a screened-in lanai, and no rear neighbors for enhanced privacy. This smart home is equipped with modern upgrades, including a gutter system, paver driveway, tile roof for longevity, and a 2-car garage. With landscaping handled by the community, you’ll enjoy low maintenance living and more time to take advantage of the incredible amenities. Located in the heart of Winter Park, this property offers the perfect blend of luxury, convenience, and lifestyle.

1465 Lone Feather Trail, Winter Park
$395,000
4 Beds ⋅ 3 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code
Welcome to this unique 4-bedroom ranch-style home in the heart of Winter Park! This residence offers flexibility and comfort for today’s lifestyle. The converted two-car garage has been transformed into an additional bedroom with separate entrance, perfect for guests or an in-law suite. Inside, the kitchen flows seamlessly into the bright family room. Entertain with ease in the large dining and living room combination, or step outside to enjoy the expansive screened and covered patio overlooking the fully fenced backyard. Additional highlights include energy-efficient Low-E double-pane windows, a gas water heater, and tiled living areas. Two guest bedrooms, along with the original primary suite, complete this thoughtful layout. Located in a quiet neighborhood served by highly rated Seminole County schools, this home offers unmatched convenience—just minutes to boutique shops and dining on Park Avenue, Rollins College, UCF, Full Sail, Research Parkway, and easy access to 408 and 417 for commuting. Don’t miss your chance to own this beautifully updated and versatile Winter Park home—schedule your private showing today! ROOF 2021, HVAC 2024, Water Heater 2024

1362 Tierra Circle, Winter Park
$849,990
4 Beds ⋅ 4 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Stunning, one of kind, 4/4 Winter Park pool home loaded with upgrades! ROOF, AC & WATER HEATER (2020), NEW FLOORING, KITCHEN & BATHS (2025), QUARTZ COUNTER TOPS (2025) FRESH INTERIOR PAINT (2025) & EXTERIOR (2023). Enjoy NEW DRIVEWAY PAVERS, FRONT YARD IRRIGATION (2025), REPLACEMENT WINDOWS & FRENCH DOORS (2016). Largest old school POOL in the neighborhood (20x40) RESURFACED (2016) with NEW PUMP (2023). LED RECESSED LIGHTING (2025). Upgrading LED LIGHTING (2025) Rear addition (Man Cave) is perfect for entertaining with newly installed quartz counter top bar area. UPGRADED ELECTRICAL PANEL (2024) REPLUMBED (2016) Close to coveted Winter Park High, Aloma Elementary, Hospitals, SR 436, Full Sail University, Golfing, Dining and Entertainment. Move-in ready with modern finishes inside & out! Listing Agent is the owner of the property, SELLER may OFFER CONSESSIONS WITH AN ACCEPTABLE OFFER!

730 S Ranger Boulevard, Winter Park
$700,000
4 Beds ⋅ 2 Baths ⋅ Greenview At Winter Pines SubDv. ⋅ 32792 Zip Code
MULTIPLE OFFERS. The Sellers are calling for highest and best offer submissions by Monday, September 15th at 5:00 PM. Golfside living, beautifully reimagined. From the moment you step inside, your eyes are drawn to serene water and golf course views — a daily reminder of why this address is so special. This 4-bedroom, 2-bath retreat in Winter Park Pines marries timeless charm with thoughtful modern updates — from the warmth of a wood-burning fireplace to a dream kitchen dressed in quartz, honeycomb tile, and designer lighting. A versatile dining or flex space invites effortless entertaining or the perfect work-from-home setting. The Florida room, bathed in natural light, creates a seamless connection between indoor comfort and the picturesque landscape beyond — a space to linger over morning coffee or unwind at sunset. The primary suite feels like a private sanctuary with peaceful views of the water and rolling fairways. Its en-suite bath, fully reimagined in 2023, offers dual vanities, shiplap accents, and a glass walk-in shower with rainfall and handheld features — a retreat designed for pure exhale. Three additional bedrooms, well-appointed with ceramic flooring and ceiling fans, provide both comfort and flexibility. A second fully renovated bath shines with brushed gold fixtures, quartz vanity, and carefully curated tile work. Step outside to the brick paver patio with motorized retractable awning, where mornings glow and evenings linger against a backdrop of water and golf course greens. A city-permitted fenced side yard adds storage for a boat, camper, or weekend toys. This home’s updates bring peace of mind: new roof (2024), dual hybrid water heater (2024), garbage disposal (2025), plumbing upgrades (2020–2025), all-new ductwork and insulation (2022), new garage door motor and springs (2025), plus a serviced HVAC system every 6 months. Ideally located near Winter Park Pines Golf Club, Cady Way Trail, pool, playground, tennis and pickleball courts, Ward Park, and A-rated schools (Brookshire Elementary, Glenridge Middle, Winter Park High), this home is equally close to Rollins, UCF, and Full Sail. With Park Avenue, AdventHealth Winter Park, Crosby Wellness, and everyday shopping minutes away, where convenience meets connection. Practical and picturesque. Light-filled and lifestyle-rich. A Winter Park home where every detail — and every view — feels like home.

1729 Golfside Drive, Winter Park
$415,000
4 Beds ⋅ 2 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code
Charming 4-Bedroom, 2-Bathroom Home in Winter Park's Casa Aloma Discover the perfect family retreat in the heart of Winter Park’s coveted Casa Aloma neighborhood. This beautifully updated 4-bedroom, 2-bathroom home offers the ideal blend of comfort, style, and functionality. Nestled on a lush lot with mature landscaping, the property is highlighted by a double-car garage and plenty of room for family living. Recent upgrades mean you can move in with peace of mind: a complete re-pipe in 2023, a new roof in 2021, and a modern HVAC system also installed in 2021. Step inside to find a spacious formal living room, where sliding glass doors lead out to a serene screened-in patio—perfect for entertaining or relaxing. The adjacent dining room sets the scene for family meals, while the fully updated eat-in kitchen features sleek stainless-steel appliances and another set of sliding doors opening to the patio, flooding the space with natural light. The kitchen flows seamlessly into a cozy family room, offering an inviting space to unwind. From here, three well-sized bedrooms share a full bathroom complete with double vanities. The large primary bedroom provides a private sanctuary with its own en-suite bathroom featuring a walk-in shower and ample closet space, including his-and-her closets for added convenience. Outside, the fenced backyard offers a safe haven for kids, pets, or your gardening passions. Conveniently located near Winter Park’s renowned shopping, dining, and the vibrant Park Avenue, this home truly has it all. Don’t miss the opportunity to make it yours! All information taken from the tax record, and while deemed reliable, cannot be guaranteed.

2681 Tierra Circle, Winter Park
$465,000
4 Beds ⋅ 2 Baths ⋅ Wrenwood Heights Unit 2 SubDv. ⋅ 32792 Zip Code
ENTERTAINING ALL OFFERS! This beautifully updated 4 bedroom, 2 bathroom, 2 car garage home offers modern style, thoughtful upgrades, and a prime location just steps from the neighborhood elementary school. From the moment you arrive, you’ll notice the curb appeal of the corner lot framed by mature trees and a newer white vinyl fence. Inside, the home features a spacious split floor plan with wood-grain laminate flooring, recessed lighting, and UPDATED fixtures throughout. The custom kitchen is a chef’s dream with granite countertops, white cabinetry, a large island, stainless steel appliances, and a perfect sized pantry—seamlessly opening to the dining room AND great room for effortless entertaining. Retreat to the oversized owner’s suite with a SPA-LIKE private bath showcasing custom tile work, dual vanities, and a his-and-hers closet. Secondary bedrooms feature large closets and share a beautifully updated bathroom, as well. The home also offers formal living and dining spaces for flexible living. Step outside to enjoy a fully screened patio with stunning tile flooring—perfect for relaxing or hosting guests year-round. Peace of mind comes with a NEWER roof, NEWER A/C, and NEWER water heater, as well as updated double-paned WINDOWS, with beautiful wood blinds and elegant touches like 5 inch baseboards and serene colors throughout. The home comes complete with a functioning Rainbird irrigation system, as well. Don’t miss the chance to own this move-in ready home combining style, function, and comfort in one perfect package!

7104 Wrenwood Way, Winter Park
$660,000
4 Beds ⋅ 3 Baths ⋅ Howell Estates Rep SubDv. ⋅ 32792 Zip Code
**VA Assumable**A HIDDEN GEM nestled on Lake Deeks in Howell Estates! You have lake access from your back yard! As you enter your new home you will be captivated by the abundant natural light and the spacious open floor plan. The beautiful vintage front door signals this home is full of wonderful and unique touches. Pictures include a floor plan to show you the amazing layout with so much privacy with separate bedroom areas and how great the home is for entertaining. The primary bedroom has access to a private lanai with a sink and wood burning fireplace and leads to the pool and back yard. The guest suite on the opposite side of the house also has outdoor access to another larger lanai and the pool. The primary bathroom has a jet tub, large shower with double shower heads. The shower area is solid concrete reinforced for extra safety during weather events. The bathroom also has two walk in closets. The other two bedrooms are secluded with a full bath with a jet tub and a skylight. The kitchen is a culinary delight, featuring granite countertops, ample prep and cooking space, walk-in pantry, built in desk and a long breakfast bar. The oversized family room has a wood burning fireplace, vaulted ceiling with beams and four large window overlooking the pool with remote controlled shades. As you make your way to the back yard oasis you will find many surprises! Several paths will walk you through to see 20 banana trees, Meyer Lemon tree, Fig tree and much more. Enjoy the deck on the water for sunrises/sunsets and watching shuttle launches. There is a path that leads to the lake for launching your kayak, canoe and paddle board. More features include oversized paver driveway, pavers on the pool deck, garage with lots of built-in storage, floored attic area, large separate laundry room, solar panels (fully paid), water softener system, custom plantation shutters, transferable home warranty and termite bond. Your home is in a lovely quiet area but close to all shopping, transportation and renowned Seminole County schools. This great home is a must see and the perfect forever home for the sought after Florida lifestyle. Buyer to confirm room measurements.

1023 Princess Gate Boulevard, Winter Park
$350,000
4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 07 SubDv. ⋅ 32792 Zip Code
No HOA. Seller offering $10,000 towards closing costs or repairs . Desirable Winter Park Neighborhood! Welcome to this beautiful 4-bedroom, 2-bathroom and 2 car garage. Home situated on a spacious corner lot. This property features an open layout, gorgeous flooring throughout, and a 2-car garage. The home has been re-plumbed, features a 2 year old roof, and the electrical system has been update to code. Conveniently located near the Airport, Downtown Orlando, Shopping and Restaurants, public transportation.

3521 Balsam Drive, Winter Park