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1453 Via Sangro Place, Winter Park
$985,000
4 Beds ⋅ 3 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code
Welcome to refined Florida living in the highly sought-after gated community of Lakeside Estates, one of Winter Park’s most exclusive neighborhoods, where homes rarely come to market. With only 39 residences, this intimate lakefront community offers a level of privacy, prestige, and curb appeal that is increasingly difficult to find. From the moment you pass through the impressive gated entrance framed by a beautifully designed pond, elegant stone wall, and striking fountain, you immediately sense that Lakeside Estates is something special. This Mediterranean-inspired residence showcases timeless architectural design with a stunning stone-accented tower entry, graceful arched architecture, and a classic barrel tile roof, all complemented by a beautifully maintained paver driveway and a welcoming 8-foot front door. Inside, thoughtful craftsmanship is evident throughout, with colonial-style crown molding, designer finishes, and wood-look porcelain plank tile flooring that delivers the warmth of hardwood with exceptional durability. At the heart of the home, the chef’s kitchen is designed for both everyday living and entertaining, featuring white shaker cabinetry with crown molding, quartz countertops with elegant marble-inspired veining, stainless steel appliances, and a double oven. A beautifully appointed butler’s pantry with a built-in wine rack enhances both convenience and sophistication. The versatile floor plan includes a dedicated office, four bedrooms, spacious living areas, and generously sized rooms, creating flexibility for modern lifestyles. The primary suite provides a private retreat with spa-inspired features and ample storage. Step outside to your own backyard oasis featuring an enclosed saltwater pool, peaceful water views, and pre-plumbing for a future outdoor kitchen, making this outdoor space ideal for year-round entertaining. A convenient full pool bath provides easy access for guests while enjoying the outdoor living areas. Additional highlights include wall-mounted garage storage, kayak storage, and thoughtful design details throughout. Residents of Lakeside Estates enjoy access to a community dock where fishing and kayaking are possible, along with a playground and beautifully maintained common areas, all supported by an HOA that maintains the entrance and shared spaces. Ideally located in Winter Park and zoned for highly regarded schools, this home offers a rare opportunity to own within a private gated community where availability is limited, and demand remains strong.

1453 Via Sangro Place, Winter Park

1725 Carollee Lane, Winter Park
$980,000
3 Beds ⋅ 2 Baths ⋅ Green Terrace SubDv. ⋅ 32789 Zip Code
Nestled in one of Winter Park’s most sought-after neighborhoods, this charming and meticulously maintained home offers three bedrooms, two baths, an open floor plan, hardwood floors, and thoughtful updates throughout. Recent improvements include a new AC, new hot water heater, new driveway and walkway pavers, and refreshed front and backyard landscaping featuring a magnolia tree, camellias, gardenias, and more. Just minutes from Park Avenue’s beloved restaurants, cafés, and boutiques, as well as the scenic Winter Park Chain of Lakes, this home offers both character and convenience. With easy access to I-4, SR-417, Orlando International Airport, and top-rated schools, it is a wonderful opportunity to enjoy classic Winter Park charm in a beautifully cared-for home.

1725 Carollee Lane, Winter Park

241 W Lake Sue Avenue, Winter Park
$960,375
3 Beds ⋅ 3 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code
A/C system and ductwork (2023), roof (2021), replumb (2026). For the right buyer, this is a rare chance to secure a premier location at a value that’s increasingly hard to find. Welcome to 241 W. Lake Sue Avenue, an exceptional offering in Virginia Heights, one of Winter Park’s most cherished and established neighborhoods. Nestled along a picturesque oak-canopied brick street and surrounded by multimillion-dollar estates, this beautifully updated pool home sits on an oversized 12,000-square-foot lot and delivers the lifestyle that defines Olde Winter Park living. Designed for effortless indoor-outdoor enjoyment, the home features sunlit interiors, soaring ceilings, architectural wood-beam accents, travertine flooring, and inviting gathering spaces that overlook a private backyard retreat. The chef’s kitchen anchors the residence, connecting seamlessly to the living and dining areas while offering serene views of the pool, spa, and lush outdoor living spaces. The spacious primary suite provides a calming escape with vaulted ceilings, a spa-inspired bath, and a generous walk-in closet. What truly sets this property apart is its location within Virginia Heights, where residents enjoy deeded access to a private Lake Virginia waterfront park. Just a short stroll away, homeowners have exclusive use of a private dock, canoe and kayak storage, open green space, and sweeping lakefront views across from Rollins College, an amenity rarely found in Winter Park. Moments from Park Avenue’s boutiques and dining, nearby parks, cultural venues, and top-rated schools, this home blends timeless charm with modern comfort in one of the city’s most coveted enclaves. Opportunities to purchase in Virginia Heights are limited; opportunities with private lake access, an oversized lot, and a resort-style backyard are even rarer. Priced below market value due to cosmetic updates needed, this property invites you to enhance the existing residence or build a new home from the ground up. Either path securing a legacy-worthy homesite in one of Winter Park’s most desirable locations!

241 W Lake Sue Avenue, Winter Park

1120 Wisconsin Avenue, Winter Park
$920,000
3 Beds ⋅ 4 Baths ⋅ Henkel Add SubDv. ⋅ 32789 Zip Code
Curated with intention and finished without compromise, 1120 Wisconsin Avenue is a rare opportunity to own a bespoke Winter Park residence where elevated design meets effortless everyday living. Every detail of this 2,213-square-foot, three-bedroom, three-and-a-half-bath home has been thoughtfully considered — from the custom Pella® multi-point entry door that welcomes you into a light-filled, open-concept gathering room, to the chef's kitchen anchored by a dramatic waterfall island and ZLINE commercial-style gas range with soft-close cabinetry and curated high-end appliances throughout. A private courtyard entry sets a serene tone before you've even stepped inside. The seamless indoor-outdoor connection continues through Pella® wood-clad sliding glass doors to a covered BBQ kitchen lanai — your own tranquil outdoor retreat. The primary suite is a true sanctuary: a generous walk-in closet, a sitting area, linen storage, and a spa-caliber bathroom with a double-sink vanity and oversized walk-in shower. Upstairs, two spacious en-suite bedrooms and a versatile loft with built-in storage offer flexibility for guests, family, or a refined home office. Finished with stunning hardwood floors, soaring ceilings, custom window treatments, spray foam insulation, and dual-zone climate control, this home is as quietly practical as it is undeniably beautiful. Whether you're entertaining or simply unwinding, 1120 Wisconsin Avenue offers the ease and elegance of a true lock-and-leave lifestyle in one of Winter Park's most sought-after neighborhoods.

1120 Wisconsin Avenue, Winter Park

250 Cortland Avenue, Winter Park
$920,000
3 Beds ⋅ 2 Baths ⋅ Cortland Park SubDv. ⋅ 32789 Zip Code
Virtually Staged. Introducing 250 Cortland Ave — a refined expression of Winter Park living, ideally positioned on one of the area’s most picturesque brick-lined streets, surrounded by established luxury homes and mature canopy trees. From the moment you arrive, the home exudes a quiet sophistication, with manicured, low-maintenance landscaping and a sense of privacy that carries throughout the property. An oversized two-car garage and thoughtfully designed exterior set the tone for what awaits inside. Step through the entry and into a light-filled interior where volume ceilings and an open-concept layout create an immediate sense of space and flow. The home is designed to draw your eye outward — through expansive living areas, beyond the enclosed lanai, and into the serene pool and spa, creating a seamless connection between indoor and outdoor living. Every detail has been carefully curated to balance warmth and modern refinement. Rich Brazilian rosewood flooring anchors the main living spaces, while durable quarry tile provides both style and functionality in the kitchen and transitional areas. The kitchen itself has been reimagined with updated cabinetry and modern appliances, offering a clean, sophisticated space that remains highly functional for everyday living and entertaining. The split floor plan provides both comfort and privacy, with a spacious primary suite and well-appointed secondary bedrooms. Both bathrooms have been tastefully updated with contemporary finishes, while additional enhancements throughout the home — including updated lighting, hardware, flooring, and fresh interior touches — contribute to its move-in-ready appeal. Designed for the Florida lifestyle, the home truly comes to life when the expansive sliding glass doors are opened, blending the interior with the screened outdoor living space. The pool and spa become a natural extension of the home — perfect for quiet mornings, entertaining guests, or simply enjoying the year-round sunshine in complete privacy. Located just moments from Lake Mizell, part of the highly sought-after Winter Park Chain of Lakes, the property offers not only a beautiful home, but a lifestyle defined by scenic surroundings, walkability, and timeless charm. 250 Cortland Ave is more than a home — it is a rare opportunity to own a thoughtfully designed residence in one of Winter Park’s most desirable and established neighborhoods.

250 Cortland Avenue, Winter Park

1800 Magnolia Avenue, Winter Park
$918,000
4 Beds ⋅ 3 Baths ⋅ Temple Terrace SubDv. ⋅ 32789 Zip Code
Virtually Staged. JULY 2026 NEW CONCRETE CIRCULAR DRIVE AND NEW CONCRETE SIDEWALKS! PRICE IMPROVEMENT! NO HOA! SEPTIC INSPECTED AND CERTIFIED. Experience refined living in this renovated custom designed home on a corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. With soaring 10-foot ceilings throughout and a stately wood-burning fireplace which sets a welcoming feeling in the family room. The fully reimagined chef’s kitchen is a true showpiece, featuring solid maple cabinetry, quartz countertops, programmable Bosch stainless steel range and refrigerator and a striking brick backsplash—an elevated space designed for both culinary creativity and effortless entertaining. All three bathrooms have been luxuriously renovated, and new carpeting adds a soft, refined touch throughout all four bedrooms. French doors from the master suite, formal living room, and family room open to a breathtaking screened-in pool retreat. Surrounded by lush tropical landscaping, this private oasis has been thoughtfully upgraded with a new pool pump, a conversion to a sparkling saltwater system, and a beautifully refinished pool deck. An outdoor shower with both hot and cold water adds a resort-level convenience, perfect after a swim or a day in the sun. Every major system has been meticulously updated for peace of mind, including a new programmable HVAC system, a complete replumb of the entire home, all new ductwork, and an upgraded water heater. Additional enhancements—such as fresh interior and exterior paint, a new garage door opener in the over-sized garage, irrigation system and refreshed landscaping — ensure a truly turnkey experience. With its luxurious finishes and meticulous improvements, this residence is ready for the next family to make it their own. This property is located just 2 miles to AdventHealth Winter Park Hospital, less than 10 minutes to Park Ave, and zoned for top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High School. Just minutes from Winter Park’s boutiques, acclaimed restaurants, and the cultural charm of Park Avenue, this home offers a rare opportunity to enjoy elevated living in a setting that’s both secluded and connected. A truly private sanctuary designed for comfort, style, and the best of Florida living.

1800 Magnolia Avenue, Winter Park

1492 Via Sangro Pl, Winter Park
$905,000
4 Beds ⋅ 3 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code
Experience refined Florida living in this exceptional single-story residence, ideally situated on a quiet cul-de-sac within an intimate gated community in one of Winter Park's most desirable locations. Impeccably maintained, this elegant home offers over 3,000 square feet of thoughtfully designed living space with 4 bedrooms, 3 full baths, a private office, and a desirable three-way split floor plan that provides both privacy and flexibility. Designed for comfortable everyday living and effortless entertaining, the home features formal living and dining rooms, a spacious family room, and a bright breakfast area. The stunning gourmet kitchen is the heart of the home, showcasing timeless white cabinetry, quartz countertops, abundant prep space, a convenient butler's pantry, and an open flow to the main living areas. The generous primary suite offers a spacious walk-in closet and a luxurious retreat, while quality finishes and meticulous attention to detail are evident throughout. Enjoy year-round outdoor living on the private screened lanai, perfect for relaxing or entertaining. Additional highlights include a three-car garage, a durable tile roof, and a fully paid solar energy system, keeping the average monthly electric bill under $100. Combining elegance, energy efficiency, and an outstanding location, this move-in-ready home offers the perfect balance of luxury, comfort, and convenience.

1492 Via Sangro Pl, Winter Park

1960 Winter Park Road, Winter Park
$892,500
3 Beds ⋅ 3 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Discover the perfect canvas for your dream home at 1960 Winter Park Road! With utilities and sewer connected, plus a complete roof replacement in 2019, newer gutters with gutter guards added in 2020, and various new appliances and thoughtful upgrades since, this ¼-acre lot presents the ideal opportunity to either build new, or remodel. Zoned for the highly esteemed Audubon K-8 School, this property offers an ideal location nestled in one of the most coveted pockets of Winter Park. Stroll down the brick-lined street and land at East End market, Kelly’s Homemade Ice Cream, and all the shops and restaurants along the vibrant Corrine Drive corridor; walk around the corner to Blue Jacket Park; or venture North just 2.5 miles to discover the cultural delights of Park Avenue in downtown Winter Park. The existing 1940's home is still bursting with charm and potential. From the moment you arrive, the circular paver driveway and inviting front porch set the tone for a home that balances warmth and functionality. The main residence offers 2 bedrooms and 2 bathrooms across 1,500+ square feet, complemented by a detached 1-bedroom, 1-bath guest cottage. Ideal for extended stays, a private office, hobby space, or flexible living arrangements, the detached cottage presents endless possibilities, with enough space available for creative modifications to suit your needs. A paver 2-car parking pad off the circular drive allows room for temporary or long-term guests, with the added convenience of private entry to the detached dwelling via a paved walkway through the side gate. The main home is well-laid-out, with multiple living & dining spaces to make everyday living and entertaining a breeze, all anchored by hardwood flooring throughout. A spacious, paver side patio and large rear deck offer separate, gated outdoor living areas for versatility and enjoyment, while the rear deck overlooks a private, fenced-in backyard just waiting to be transformed into the perfect Florida oasis. If you are looking to land just a few minutes from downtown Orlando and downtown Winter Park, with easy Access to I-4…this is the location for you!

1960 Winter Park Road, Winter Park

1960 Winter Park Road, Winter Park
$892,500
Charmont SubDv. ⋅ 32789 Zip Code
Build your dream home in one of Winter Park’s most desirable pockets. This 83’ x 123’ lot (10,258 SF | .24 acres) offers the perfect canvas to create a custom residence tailored to your vision. With utilities and sewer already connected, the groundwork is in place to streamline your building process. Positioned on a charming brick-lined street and zoned for highly regarded Audubon K-8, the location is exceptional…just moments from East End Market, Kelly’s Homemade Ice Cream, and the vibrant Corrine Drive corridor. Enjoy nearby outdoor spaces like Blue Jacket Park, or head just 2.5 miles north to experience the boutiques, dining, and cultural attractions of Park Avenue. The property is currently improved with a well-maintained 2-bedroom, 2-bath main home (approx. 1,500+ SF) and a detached 1-bedroom, 1-bath guest cottage…ideal as a rental opportunity or comfortable residence while finalizing plans and preparing to build. Live in or lease the existing structures now, and build at your pace later. Whether you envision new construction or a thoughtful redevelopment, this is a rare opportunity to secure a prime homesite in an established, walkable Winter Park location.

1960 Winter Park Road, Winter Park

627 Dunblane Drive, Winter Park
$887,500
4 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 04 SubDv. ⋅ 32792 Zip Code
Set on a beautiful tree lined Winter Park neighborhood street with sidewalks and manicured lawns is this fully updated, move-in ready, 4 bed, 3 full bath abode with pool and cabana. Paver drive and walkway lead to the front porch and into the spacious great room, where beautifully refinished original hardwood floors run throughout. A freshly updated bar and serving area opens into the light and bright kitchen with newer stainless-steel refrigerator, microwave and dishwasher (all 2022). A gas cooktop and double wall oven make this kitchen a home cook’s dream, along with the freshly painted solid wood cabinets with soft close drawers and center island. The large dining room overlooks the pool through a double set of French doors with built-in blinds. Beautiful hardwood herringbone flooring in the primary suite makes this space special, along with the luxury ensuite featuring a double sink quartz vanity, fabulous large format porcelain floor and wall tile including in the glass shower enclosure, and custom cabinetry in the large walk-in closet. On the opposite side of the home are 3 more bedrooms (one with its own ensuite with shower) and a full hall bathroom with double sink granite-topped vanity and shower/tub combo. The laundry room with utility sink and storage cabinets leads to the oversized 2-car garage with epoxy floor coating, insulated garage door, and NEW mini-split AC/heat unit, making this a stunning space for your treasured auto or a great workout or hobby room. Enjoy tropical paradise living in the backyard with the solar heated pool, paver patio deck, and large covered cabana (12'x20'). There’s still plenty of green grass in the fully fenced backyard for little ones or pets to run around. Home features and improvements include: newly refinished wood floors 2026, newly painted kitchen cabinets and bar 2026, double pane windows, new tankless water heater (propane gas) 2021, whole home roof foam insulation 2021, new HVAC 2021, refinished pool, paver deck, cabana 2018, Roof 2016, and replumb CPVC 2014. Located in sought after school zones of Brookshire Elem, Glenridge Middle, and Winter Park High and close to Park Ave shops and restaurants or Baldwin Park Village Center, you’ll have access to everything you could want or need.

627 Dunblane Drive, Winter Park

1407 Miller Avenue, Winter Park
$875,000
3 Beds ⋅ 3 Baths ⋅ H Vanwies Sub SubDv. ⋅ 32789 Zip Code
Experience refined luxury and effortless living at 1407 Miller Avenue, ideally situated in one of Winter Park’s most desirable and walkable enclaves near the NEW Minnesota Row. Built by SGC Homes, this exceptional Modern Mediterranean detached townhome combines timeless architecture with sophisticated contemporary finishes along a charming, tree-lined brick street. Offering 3 bedrooms, 2.5 bathrooms, and 1,884 square feet of thoughtfully designed living space, the residence features a highly sought-after first-floor primary suite and the privacy of only one shared wall at the garage—no shared interior living walls!! Interior highlights include Level 4 drywall finishes, wide-plank engineered oak flooring, Bosch appliances, LED mirrors, and an impressive Hunter Douglas automated shade system. The open-concept floor plan is both functional and inviting, filled with natural light and seamlessly extending to a private paved patio and fenced backyard—ideal for entertaining, quiet outdoor living, or the future addition of a pool or spa. Set within an exclusive four-residence enclave, this low-maintenance property offers a true lock-and-leave lifestyle just minutes from Park Avenue’s premier dining, boutique shopping, Publix, AdventHealth, and everyday conveniences. Additional features include a private two-car garage with EV charging capability and dedicated guest parking. A rare opportunity to own a design-forward residence in the heart of Winter Park.

1407 Miller Avenue, Winter Park

2823 Wright Avenue, Winter Park
$865,000
Lake Forest Park SubDv. ⋅ 32789 Zip Code
**BUILD YOUR DREAM HOME** A rare opportunity to secure over half an acre of lakefront land in one of Winter Park’s most coveted residential corridors. NO HOA. Situated directly on Lake Forest, this 0.54-acre parcel offers the kind of lot that simply doesn’t come available in this market - expansive, private, and adorned with mature tree canopy that frames sweeping water views. The homesite carries an R-1A zoning designation and is tucked on a quiet street, yet sits just minutes from the dining, shopping, and culture of downtown Winter Park and Baldwin Park. The generous lot dimensions provide ample room for a custom estate build, a pool, and meaningful setbacks. Served by top-rated Audubon Park K-8 and Winter Park High School, and positioned within one of Central Florida’s most desirable zip codes.

2823 Wright Avenue, Winter Park

2823 Wright Avenue, Winter Park
$865,000
3 Beds ⋅ 2 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code
Rare opportunity to own a beautifully upgraded lakefront property on half acre in one of Winter Park's most desirable locations. This homesite offers the perfect setting to enjoy the current residence or build your future dream home! When you step inside you'll find a thoughtfully updated kitchen featuring high-end appliances, custom cabinetry, and designer finishes. The home boasts new windows that fill the space with natural light and frame serene lake views, as well as a brand new roof and AC offering peace of mind for years to come. Split floor plan with 3 large bedrooms and each has a walk-in closet. Step outside and take in the beautifully landscaped yard, complete with mature trees and plenty of space and privacy. Whether you’re sipping coffee by the water or hosting friends for a sunset BBQ, this home is made for living the good life! Zoned for A rated schools. Situated on a quiet street yet just minutes from Winter Park and Baldwin Park dining, shopping, parks and culture. Call today before it's gone!

2823 Wright Avenue, Winter Park

1018 Turner Road, Winter Park
$850,000
3 Beds ⋅ 2 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code
Seller may consider buyer concessions if made in an offer | Lakefront charm meets quiet luxury in the heart of Winter Park! This beautifully updated single story POOL HOME sits on nearly HALF AN ACRE of LAKEFRONT PROPERTY on the coveted LAKE BELL - a private SKI LAKE - offering a private dock/boat lift, character and contemporary upgrades that make everyday feel like a lakeside retreat. Major updates include a NEW ROOF (2022), A/C (2022), TILE FLOORING THROUGHOUT (2023), a COMPLETE KITCHEN RENOVATION (2023), and a FULLY REMODELED PRIMARY BATH (2023). Enjoy peace of mind with double pane windows, fresh interior and exterior paint (2022), and a septic system service also (2022). The home also features NEWER WINDOW TREATMENTS (2022), a new pool pump (2023), and NEW DOCK DECKING (2024)! Inside you will be pleased to find vaulted ceilings, an abundance of NATURAL LIGHT, and a light, bright OPEN FLOOR PLAN that flows seamlessly between formal and family spaces. From the moment you enter you are greeted with UNINTERRUPTED LAKE VIEWS, setting the tone for a home designed around its beautiful surroundings. The layout includes a spacious FLORIDA ROOM overlooking the pool and lake beyond – perfect for year round enjoyment! Step outside to your private outdoor oasis featuring an open-air pool with waterfall feature, patio, lush landscaping and a fun in the sun SAND BEACH leading to your private dock. Sunset views over the water are a daily luxury! Located in one of Winter Park’s most desired neighborhoods, you are only minutes away from top-tier dining, boutique shopping, parks, and major roadways like US 17/92, Orlando Ave and I-4. With its blend of charm, modern updates, and an unbeatable lakefront setting, this home truly is a rare GEM. Call today to schedule your tour and start living the LAKE LIFE – where every day feels like a vacation!

1018 Turner Road, Winter Park

269 E Canton Avenue Unit 269, Winter Park
$845,000
1 Beds ⋅ 2 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code
Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings beneath stately oaks, and the privilege of living in a community where privacy and exclusivity are paramount. This fully remodeled Penthouse Suite's location is unmatched—one block to Park Avenue, offering effortless access to fine dining, boutique shopping, the Morse Museum, Rollins College, and the scenic Chain of Lakes. Whether you’re downsizing, escaping winter months or seeking a refined second home, this residence delivers the perfect blend of luxury, simplicity, and prestige. Designed for comfort and ease, the home welcomes you with a bright, open living space enhanced by crown molding, warm natural light, and a seamless flow ideal for both quiet escapes and intimate entertaining. The primary suite features a generous walk-in closet, while the kitchen offers modern functionality with quality appliances and thoughtful storage. This unit offers its own washer/dryer combo unit, large exterior storage closet, assigned parking space under canopy and extra open parking spaces. Please note rentals are not allowed and no pets except for Service Animals.

269 E Canton Avenue Unit 269, Winter Park

2119 Howard Drive, Winter Park
$841,500
4 Beds ⋅ 2 Baths ⋅ Timberlane SubDv. ⋅ 32789 Zip Code
Welcome to this charming residence in the heart of sought-after Winter Park. Pride of ownership is evident throughout this home and significant updates include a new roof being installed before closing, HVAC replaced in 2020, updated electrical in 2023 and a plumbing repipe in 2012. The spacious layout provides comfortable living and entertaining with a formal living room, formal dining room and sun-filled Florida room. Storage is plentiful in this house with several spacious closets and a generously sized walk-in closet in the primary bedroom. The primary bath includes a separate make up and vanity space. The property sits at just over a quarter acre and includes a long, brick paver driveway with plenty of parking and a private rear-entry garage. Ideally situated near the best of Winter Park and Audubon Park, residents enjoy convenient access to local dining, shopping, parks, and top-rated schools, including Audubon Park K8 and Winter Park High School. This coveted neighborhood is full of charm and tons of beautiful oak trees. Walk to Fleet Peoples dog park, hop on the 3 mile trail around Lake Baldwin or ride your bike to Park Avenue and the Farmer's Market on the weekends. This is a wonderful opportunity to own a well-cared-for home in one of Central Florida’s most desirable communities. Schedule your private showing today and see how you can make this home yours!

2119 Howard Drive, Winter Park

1405 Miller Avenue, Winter Park
$840,000
3 Beds ⋅ 3 Baths ⋅ H Vanwies Sub SubDv. ⋅ 32789 Zip Code
Experience high-end luxury and effortless convenience in one of the most central locations in Winter Park. Built by Makeur Homes and thoughtfully updated by SMRS Design, this stunning Modern Mediterranean detached townhome showcases light-filled interiors and carefully curated custom finishes. Offering 3 bedrooms and 2.5 bathrooms across 1,884 square feet, the home features a desirable first-floor primary suite and elevated design details, including Level 4 drywall, engineered oak floors, Bosch appliances, LED mirrors, and a Lutron Caséta lighting and Triathlon shade system. A Calacatta Gold porcelain slab electric fireplace serves as a striking focal point in the living room. The open-concept floor plan is both functional and inviting, filled with natural light and offering views of a private paved patio and fenced backyard—ideal for relaxing or entertaining. Enjoy a low-maintenance, lock-and-leave lifestyle within an intimate four-unit community tucked along a picturesque, tree-lined brick street. Additional highlights include a private two-car garage with EV charging port, guest parking, and close proximity to premier dining, shopping, and daily conveniences, including Publix and AdventHealth. A rare opportunity to own a design-forward residence in an exceptional location.

1405 Miller Avenue, Winter Park

100 S Interlachen Avenue Unit 503, Winter Park
$840,000
2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code
Welcome to The Cloisters, one of Winter Park’s established lakefront communities, ideally between Park Avenue and Lake Osceola. This top-floor residence, rarely available in the building, offers a turnkey lifestyle with exceptional updates and peaceful water views. The home’s oversized screened balcony, complete with a custom awning, creates an uncommon open-air retreat that overlooks the community’s heated pool, putting green, manicured gardens and Lake Osceola. Unlike many residences in the community, this property retains its original open balcony design, offering outdoor living rarely found in this floor plan. Inside, every surface has been thoughtfully remodeled. The kitchen features solid wood cabinetry, granite countertops and refined finishes. Both baths are fully updated, including a new tub with glass enclosure in the guest bath and a walk-in shower with frameless glass in the primary suite. Tile flooring, custom vanities and designer fixtures complete each space. Engineered hardwood flooring runs throughout the main living areas, with plush carpet in the bedrooms for added comfort. The primary suite includes custom built-ins, dual closets and a built-in desk with additional cabinetry, delivering elegance and function. The second bedroom offers flexibility as a guest room or study and features optional shared access from the primary suite for additional privacy. Additional highlights include a covered and assigned parking space equipped with one of the building’s few electric vehicle charging stations, ample guest parking and access to a community dock with boat slips available through a resident lottery system. The Cloisters has successfully completed all required Milestone Inspections and the Structural Integrity Reserve Study, ensuring peace of mind for future residents and affirming the association’s commitment to long-term stewardship. Amenities include two fitness centers with dry saunas and a newly renovated clubhouse with kitchen and a partial bath for use as a powder room, ideal for hosting private events. Ideally positioned just steps from the dining, shopping and cultural energy of Park Avenue and in proximity to Rollins College, this original-owner residence offers a compelling blend of lifestyle, location and enduring design.

100 S Interlachen Avenue Unit 503, Winter Park

938 Golfside Drive, Winter Park
$830,000
4 Beds ⋅ 3 Baths ⋅ Golfside Sec 2 SubDv. ⋅ 32792 Zip Code
*Multiple offers!* 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.

938 Golfside Drive, Winter Park

2175 Marsh Sedge Lane, Winter Park
$830,000
5 Beds ⋅ 4 Baths ⋅ Hawks Crest SubDv. ⋅ 32792 Zip Code
Beautifully designed and impeccably maintained, this light-filled home offers the perfect blend of modern comfort and timeless style. Featuring an open and airy layout, the home is highlighted by abundant natural light, neutral designer finishes, and thoughtfully curated living spaces throughout. The bright and inviting living area flows seamlessly, creating the ideal space for both everyday living and effortless entertaining, while a spacious loft provides additional flexibility for a media room, lounge, or family retreat. The serene primary suite offers a true retreat-like atmosphere with soft neutral tones and abundant natural light, complemented by a well-appointed primary bath featuring dual vanities, expansive counter space, and a clean, modern design. The master bedroom is on the first floor. Additional bedrooms are upstairs, comfortable, and versatile, each filled with natural light and designed to accommodate guests, family, or personalized use. A charming flex space is also upstairs and offers endless possibilities as a playroom, creative studio, or additional living area. Secondary bathrooms are well-maintained with modern finishes and timeless appeal, enhancing both style and convenience throughout the home. Step outside to an expansive screened lanai that creates a private outdoor oasis, ideal for dining, lounging, or entertaining while enjoying tranquil views. An additional outdoor seating area further enhances the home’s indoor-outdoor lifestyle, offering the perfect setting for relaxing or gathering with guests. Move-in ready and thoughtfully styled, this home combines comfort, versatility, and elevated design in every detail, making it an exceptional opportunity for a wide range of buyers. The neighborhood also offers a plethora of amenities including a dog park, pool, clubhouse, gym, and walking trails. You are also in close proximity to dining, schools, and entertainment. Come see this home today!

2175 Marsh Sedge Lane, Winter Park

439 N Capen Avenue, Winter Park
$824,500
3 Beds ⋅ 3 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code
Life is simply better when everything is just around the corner. Perfectly positioned in the heart of Winter Park, this beautifully maintained David Weekley home offers the rare opportunity to enjoy one of Central Florida's most desirable lifestyles. Located just four blocks from Park Avenue and one block from Winter Park Village, you'll also enjoy close proximity to Hannibal Square, Central Park, Publix, the Winter Park Farmers' Market, acclaimed restaurants, boutique shopping, museums, cafés, and everyday conveniences. Built in 2017, this thoughtfully designed home blends timeless architecture with modern luxury across a spacious and functional floor plan. The first floor features three generously sized bedrooms and two full bathrooms, including a private primary suite complete with a spa-inspired bath and an expansive walk-in closet. Upstairs, the home's open-concept living spaces are designed for both everyday comfort and effortless entertaining. Natural light fills the expansive living and dining areas, while the chef's kitchen serves as the centerpiece of the home. Featuring premium Jenn-Air stainless steel appliances, a natural gas cooktop, generous cabinetry, beautiful countertops, and a large center island, it's a space equally suited for hosting friends or preparing a quiet dinner at home. Sliding glass doors extend the living area to an oversized balcony with Trex decking, creating an inviting outdoor retreat for morning coffee, evening cocktails, or dining under the stars. Built with quality and efficiency in mind, the home includes double-pane windows, great insulation, and a gas tankless water heater. The homeowners association further enhances the low-maintenance lifestyle by providing lawn and shrub care, irrigation water, and maintenance of the community perimeter wall, allowing you to spend more time enjoying your home and less time maintaining it. More than just a beautiful residence, this home offers an exceptional opportunity to experience the very best of Winter Park. Enjoy dinner on Park Avenue, spend Saturday mornings at the Farmers' Market, explore the boutiques of Hannibal Square, relax in nearby parks, or meet friends for coffee, all just moments from your front door. This is a home where luxury, convenience, and one of Winter Park's most sought-after locations come together beautifully.

439 N Capen Avenue, Winter Park

1822 Greenwich Avenue, Winter Park
$800,000
3 Beds ⋅ 2 Baths ⋅ Golfview Heights SubDv. ⋅ 32789 Zip Code
Rare opportunity in the heart of Winter Park! This property sits on a double lot (0.29 acres) — a true rarity in this highly desirable location. The existing 1953 concrete-block home (3 bed / 2 bath) with an attached garage apartment (studio + bath) and shared 2-car carport offers little to no current value and would require a complete renovation. Property will be sold as-is with no repairs. Furniture removal prior to closing is negotiable. The real value is in the land. With privacy at the end of a quiet street, and a doctor’s office next door, the property is ideally located steps from AdventHealth Winter Park Hospital, Lakemont Center, and just 5 minutes from Rollins College and Park Avenue’s shopping and dining. The property features a large tree-lined backyard, city water and sewer, cable, and electricity already available. Whether you choose to restore a solid 1950s block home or tear down and build your dream estate while saving on impact fees, this is a prime investment opportunity in one of Central Florida’s most sought-after areas.

1822 Greenwich Avenue, Winter Park

729 Monmouth Way, Winter Park
$793,500
4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
Completely reimagined with an extensive top-to-bottom renovation, this stunning four-bedroom, three-bathroom pool home offers over 2,300 square feet of beautifully curated living space in one of Winter Park's most desirable locations. Every detail was thoughtfully selected to blend timeless design with modern functionality, creating a truly move-in-ready home. Inside, large wood-look plank tile flooring installed throughout in 2024 creates a seamless flow, complemented by recessed lighting, plantation shutters, all-new designer lighting and ceiling fans, and energy-efficient windows replaced in 2024. A cozy wood-burning fireplace provides character to the beautiful living space while French doors installed in 2024 provide effortless access to the outdoor living space. Additional upgrades completed in 2024 include blown-in insulation and a gas tankless water heater. The showstopping kitchen was completely remodeled in 2024 and is designed to impress. Custom hardwood cabinetry accented with elegant gold hardware is paired with luxurious quartz countertops and a dramatic full-height quartz backsplash. A large center island with seating for four, a black farmhouse sink, pot filler, and abundant prep space make this kitchen equally suited for everyday living and entertaining. Split from the secondary bedrooms for added privacy, the spacious primary suite is a peaceful retreat featuring French doors leading directly to the pool, a dedicated makeup vanity, walk-in closet, and a beautifully renovated ensuite bathroom with a double vanity and an oversized tiled shower enclosed by frameless glass. All three bathrooms were tastefully remodeled in 2024 with timeless, high-end finishes. The oversized laundry room is as functional as it is attractive, offering built-in cabinetry for exceptional storage along with an included washer and dryer. Step outside to your own private backyard oasis situated on a beautifully landscaped .26-acre lot. The screened in-ground pool was resurfaced with mini pebble finishes in 2025, while a custom flagstone outdoor shower with a decorative rock bed creates a true resort-inspired atmosphere. Additional exterior improvements completed in 2024 include new exterior doors, gutters, French drains, and an updated two-car garage featuring epoxy flooring along with new torsion springs and rollers. Ideally located just minutes from UCF, Rollins College, Full Sail University, AdventHealth Winter Park, the Crosby Wellness Center, Winter Park Pines Golf Club, and the Cady Way Trail, residents also enjoy access to Cady Way Park with its community pool, playground, beach volleyball courts, tennis courts, and pickleball courts. Zoned for highly rated Aloma Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines a remarkable renovation with an unbeatable Winter Park lifestyle. ROOF - 2024 HVAC - 2024 ELECTRICAL - 2024 PLUMBING - 2024 TANKLESS WATER HEATER - 2024

729 Monmouth Way, Winter Park

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