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Osprey

One of the most popular communities provided by Michael Graf

Osprey

About Osprey

<p>Osprey is a tranquil coastal community tucked between Sarasota and Venice, offering a perfect blend of natural beauty and upscale living. Known for its peaceful vibe, top-rated schools, and access to the Intracoastal Waterway, Osprey is ideal for nature lovers and boaters. Residents enjoy quick access to parks like Oscar Scherer State Park, waterfront dining, and nearby beaches. With elegant neighborhoods, quiet streets, and a strong sense of community, Osprey is a hidden gem on Florida’s Gulf Coast.</p>

One of the most popular communities provided by Michael Graf

153

# of Listings

3

Avg # of Bedrooms

$404

Avg. $ / Sq.Ft.

$950,980

Med. List Price

Browse Osprey Real Estate Listings

All listings

$250,000 - $500,000

153 Properties Found. Page 1 of 11.

Nestled on a quiet street in the highly sought-after Rivendell community, this former Arthur Rutenberg model home features 4 bedrooms, 3 full baths, a den, and 2 versatile flex rooms, offering tranquil views of the pond and surrounding preserve. Framed by lush landscaping, the property features an oversized pool with a generously sized spa and ambient lighting, perfect for evening relaxation.
Inside, the wide, open floor plan boasts soaring ceilings and abundant natural light, creating an airy and uplifting atmosphere. Multiple living areas flow seamlessly into a spacious kitchen and family room, all opening to a covered lanai ideal for everyday living and entertaining. Just across the street, residents can enjoy the nearby Crescent Park and Playground.
The home includes a 2-car garage with an adjacent flex room that can easily be converted into a third garage bay or used as an exercise room, offering added functionality and storage. A rear room, currently used as an office with a built-in desk, offers added flexibility, ideal as a home office, study area, guest room, or multigenerational living space. It also features sliding glass doors that lead to a covered outdoor nook overlooking the lake, complete with a bar area, under-counter refrigerator, and sink.
This well-maintained residence has seen thoughtful updates over the years, including a NEWER ROOF (2017), HURRICANE SHUTTERS, SCREEN & PANELS FOR ALL OPENINGS, GARAGE DOOR (2019), PAVER DRIVEWAY (2022), a 5-ton A/C unit (2019), and a 2.5-ton A/C unit (2018) and newer appliances. Move-in ready with solid fundamentals, it also offers opportunities for personalization over time.
Rivendell is one of Sarasota County’s most cherished communities, spanning over 400 acres of protected nature preserves with scenic walking and biking trails, a heated community pool, and a peaceful, park-like atmosphere. Residents enjoy easy access to Oscar Scherer State Park (2 miles), the Legacy Trail (2.5 miles), Nokomis Beach (5 miles), and Siesta Key Beach (under 7 miles).
The home is also 1.4 miles (walkable and bikable) of Pine View School, ranked among the top public schools in the nation making this an exceptional location for families seeking elite educational opportunities.
With no CDD fees and a low HOA, this home offers an unmatched combination of comfort, location, and long-term value in one of Osprey’s most desirable neighborhoods. DON’T MISS THE FULL VIDEO WALK-THROUGH & THE 3D TOUR. CLICK EACH VIRTUAL TOUR LINK - TWO TOTAL.

OSPREY

766 SHADOW BAY WAY

4 Beds

3 Baths

3,438 Sq.Ft.

$998,000

MLS#: A4652814

Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the inside out to the lanai and boat dock. The kitchen features raised wood cabinets and a large 10ft long breakfast bar. The kitchen has views of the canal and opens up to the dining room and living room. As you walk into the nicely appointed open floor plan, you immediately feel relaxed while enjoying the water views and fish jumping. There is nothing to do but move in and enjoy your new home. Taking the boat out is a breeze. Just lower it into the water and you are a short ride out to the intracoastal, the Venice Jetties and Midnight Pass. There are many great waterfront restaurants you can access by boat. If you happen to catch some fish while you are out enjoying the boat, there is a fish cleaning station on the dock. Located between Sarasota and Venice with easy access to I-75. Close to shopping, beaches, restaurants, Oscar Scherer Park and so much more.

OSPREY

120 VILLA DRIVE 120

2 Beds

2 Baths

1,404 Sq.Ft.

$597,000

MLS#: N6138441

Welcome to Your Waterfront Villa in Osprey, Florida!
Discover the ultimate seasonal retreat in this beautifully updated 2-bedroom, 2-bathroom single-story villa, designed for stress-free living. Nestled in a private 25-unit secluded community, this waterfront gem offers not only stunning views but also a lifestyle of unparalleled ease and simplicity.
Key Features:
Move in ready: Move in with ease and start enjoying your new home immediately, partially turn key furnished.
Maintenance-Free Living: The all-inclusive HOA covers insurance, roof, exterior maintenance, landscaping, roads, pool, tennis, docks, cable TV, water and sewer.
Updated features include: Porcelain plank style tile; New walk-in rain shower; Florida native master garden; Impact glass windows and doors installed in 2017 & 2021; Electric window shades; New A/C in 2022; New duct work in 2020; Newer electric panel box; New roof in 2008; Home re-plumbed in 2022 (no more cast iron).
Resort-Style Amenities: Swim in the waterside pool overlooking the Intracoastal Waterway, play a match on the tennis courts, or dock your boat with ease for quick access to the Gulf.
Spacious and Modern: Open concept living area with abundant natural light and water views from the living, kitchen and primary bedroom. New Plumbing, New plank style porcelain tile flooring
Waterfront Living: Relax with serene water views from your villa with windows across the villa allowing an indoor-outdoor sense of living. Florida style.
Quiet lifestyle with close proximity to great seafood restaurants, casual tiki bars, Nokomis and Siesta Beaches, daily living shops, private golf club, and top-rated health care facilities.
Active Lifestyle: Enjoy a vibrant community with plenty of opportunities for socializing and staying active.
Leave the worries behind and embrace a lifestyle where all the essentials are managed for you. Schedule your private tour today and step into your new, carefree waterfront paradise!
SELLER WILL CREDIT BUYER $20,000 AT CLOSING TO GO TOWARD THE CONDO/HOA FEES!

OSPREY

784 SARABAY ROAD 18

2 Beds

2 Baths

1,574 Sq.Ft.

$569,000

MLS#: N6135402

Priced well below market. Great condition - move in ready. Being offered furnished. The roof is only 5 years old. This one is in the pet section. In addition to the 1152 sq ft of living area is an enclosed porch with windows and a mini-split A/C unit adding about 180 sq ft. There is a nice screened in porch just off the carport. There is plenty of storage in the workshop behind the carport and also by the airconditioned porch. The Arbors offers a clubhouse, community pool, shuffleboard and a workout area. There is also an area to park your RV, boat or trailer for an additional fee. The county boat ramp is just down the road at Blackburn Point Park. The location is great - about halfway between Sarasota and Venice with all the connivences of shopping, restaurants, beaches etc.

OSPREY

310 TROPIC DRIVE

2 Beds

2 Baths

1,152 Sq.Ft.

$129,900

MLS#: N6139154

This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family and guests, this is a residence that inspire togetherness and embodies the art of waterfront living. Crafted with luxury finishes and modern conveniences, the property is built to exacting coastal standards with dramatic focus on stunning water views. Formal and casual spaces unite elegantly, including the living room with cypress beamed ceilings, overlooking the bay. A deluxe kitchen, wine, butler’s pantry and wet bar provide a canvas for culinary exploration and entertaining elegance. A grand media room for screening films provides the ideal place to unite music and culture. The expansive primary bedroom features a sitting room, lavish bath, dual closets, a breakfast nook and expansive views over the water. Three additional bedroom suites provide privacy, views and spacious accommodations. The fifth bedroom suite is equipped for a home gym, steam room and sauna. The office and library, next to the grand marble staircase, features leaded glass doors, hand crafted, built-in shelving, a coffered ceiling and beautiful views of the Gulf. Additional space for recreation and relaxation has been accomplished to make use of every inch of the estate. Arched hallways and French doors line the living room, open to the dazzling outdoor spaces and stone terraces lead to the infinity pool. Elevator access and garages for six vehicles add ultimate convenience. Enjoy boating from the deep-water dock which features a rare and grandfathered-in covered boat lift. North Casey Key is a haven of exclusivity and serenity, minutes from shopping, world-class golf, tennis and dining.

OSPREY

1216 N CASEY KEY ROAD

5 Beds

6 Baths

8,050 Sq.Ft.

$11,750,000

MLS#: A4643654

American Property Group of Sarasota, Inc. presents 505 Luminary Blvd, Osprey, Sarasota
Property Type: Commercial Land with Existing Office Building
Property Size: 10 Acres
Discover this exceptional opportunity with over 900 feet of frontage on Tamiami Trail/US41 in Osprey, FL! This is one of the last substantial parcels available in Sarasota County with a Tamiami address. Positioned directly in the path of progress, this 10-acre parcel is ready for development with all entitlements in place.
Property Features:
Existing Office Building: 4,000 SF Freestanding Office Building with water, sewer, and electricity
Development Potential: Density for Assisted Living Facility/Memory Care at 9 units per acre
Office Space Allowable: Up to 46,000 SF of office space
Prime Location: Directly across from the new Publix and adjacent to massive new developments, including shopping plazas, restaurants, apartments/condos, and single-family homes
Infrastructure: Electric, water, and sewer in place, making the property shovel-ready
Accessibility: Easy access to Tamiami Trail from both ends of the property with simple median cuts at Southbay Drive/Luminary Blvd
Strategic Positioning: Located at the northeast side of the intersection of Luminary Blvd and Tamiami Trail in Osprey, FL

OSPREY

505 LUMINARY BOULEVARD

None Beds

None Baths

4,000 Sq.Ft.

$7,499,000

MLS#: A4616676

Welcome to 622 Bayshore Drive - where coastal luxury meets modern sophistication on one of the most sought-after stretches of Little Sarasota Bay. Tucked away on a rare and expansive .78-acre gated estate, this custom-built, contemporary masterpiece offers 90 feet of pristine waterfront, unmatched privacy, and a lifestyle defined by serenity, style and seamless connection to the water. Designed for those who crave the extraordinary, this six-bedroom, five-bath residence is a showpiece of elevated design and quality craftsmanship, built just three years ago with the finest materials and storm-resilient features. Boaters will delight in the direct bay access just minutes from Midnight Pass and the open Gulf - a true water lover's paradise. Step through the grand entrance and into a world of light, space and unobstructed bay views. The soaring 14-foot bifold glass wall in the great room opens fully to a spectacular lanai, inviting indoor-outdoor living year-round. Imagine entertaining here – sunset cocktails by the saltwater pool and spa, laughter echoing across the water and every moment framed by nature's beauty. At the heart of the home lies a chef's dream kitchen, anchored by an oversized 7'X8' waterfall edge island and outfitted with top-tier Wolf, Cove, and Sub-Zero appliances. A walk-in pantry with second refrigerator/freezer ensures effortless hosting and everyday convenience. This home is as strong as it is stunning: constructed entirely of block and stucco, equipped with Category 5 impact-rated windows and doors, and elevated above flood level - a rare combination that provides peace of mind and impressively low insurance premiums. A whole-house generator ensures uninterrupted comfort. With its expansive yard, and panoramic water views, 622 Bayshore Drive is not just a home- it's a legacy property. Perfectly positioned between Sarasota and Venice, it offers the best of both worlds: quiet natural beauty with easy access to world-class dining, shopping and culture. DON'T JUST VISIT PARADISE - OWN IT. Schedule your private tour of this extraordinary waterfront estate today.

OSPREY

622 BAYSHORE DRIVE

6 Beds

5 Baths

4,893 Sq.Ft.

$6,750,000

MLS#: A4657777

Seize the opportunity to own a piece of paradise on the exclusive North Casey Key. This sprawling one-plus-acre estate, with 107 feet of pristine gulf frontage, a walkable sandy beach, on a private road with security offering unparalleled privacy, is your personal slice of heaven. Surrounded by majestic live oaks, this property is a rare gem that embodies the timeless beauty of Old Florida living, offering a tranquil retreat with direct gulf-to-bay access. The three-bedroom, three-bath home exudes Mediterranean coastal charm and invites you to embrace the serenity of coastal life. With an expansive living room, formal dining room, country kitchen and an office, the home effortlessly combines comfort and style. Imagine cozying up with a cup of coffee in front of the fireplace in the primary bedroom as the first rays of dawn light up the sky over the Intracoastal Waterway, casting a soft glow on the water. As evening falls, step out and witness breathtaking sunsets over the gulf, painting the sky in hues of gold and pink, an enchanting end to every day. This completely fenced estate also offers a two-car attached garage and an additional three-car detached, air-conditioned garage, a dream for car enthusiasts who appreciate form and function. For boating lovers, a rare boathouse with a deck overlooking Little Sarasota Bay, two docks, one with a 7,500-pound lift, and a seawall, make it the ideal home for a waterfront lifestyle. Boat access to the gulf is a short five-minute ride through Midnight Pass. With direct access to the gulf, this property lets you indulge in the best of both worlds, an exclusive, private oasis and the beauty of the sparkling blue waters just near your door. On the exclusive north end of Casey Key, this estate offers seclusion and serenity, yet just five minutes from restaurants, Publix, CVS, 10 minutes to the City of Venice and 15 minutes to Sarasota. Commercial and private air travel is readily available. Don't miss your chance to live in one of Florida’s most desirable locations. With stunning sunsets, playful dolphins and soothing sound of waves as part of your everyday life, this is more than a home, it's a sanctuary. Experience the ultimate coastal lifestyle and make this paradise yours.

OSPREY

1049 N CASEY KEY ROAD

3 Beds

3 Baths

2,582 Sq.Ft.

$4,750,000

MLS#: N6137711

One or more photo(s) has been virtually staged. **NEWLY RENOVATED, SPACIOUS, GOLF COURSE ESTATE** Boasts OVER 9,000sf and is situated on a prominent, private cul de sac lot of Over 3/4 Acres. Expansive room abounds in this LIGHT and BRIGHT Open Floorplan consisting of 4 Beds + 4/2 Baths + Office/Library + Home Theater + Game Room w/ Wet Bar, Loft, Balcony, etc. and even includes highly coveted, oversized and split 4-CAR GARAGE(s). This MOVE-IN READY home has been tastefully updated and is ideal for indoor and outdoor entertaining! The elegant first level primary bedroom suite features high ceilings, multiple walk-in closets, garden tub, large custom walk-in shower and an adjacent nursery/fitness/den area. The sprawling, gourmet kitchen entails a generous island and counter seating area, premium stainless steel appliances, granite counters, solid wood cabinets, walk-in pantry and more. The upstairs loft leads to two vast bedroom suites, theater room and screened terrace/balcony. Enjoy the utmost in Florida outdoor living with a Heated Pool & Spa with Fire features and a large screened lanai with Outdoor Kitchen and seating areas while overlooking the serene interior, Heron Golf Course. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR**

OSPREY

854 MACEWEN DRIVE

4 Beds

4 Baths

9,081 Sq.Ft.

$4,195,000

MLS#: A4627698

EXCEPTIONAL WATERFRONT RESIDENCE on the exclusive island of North Casey Key is a rare opportunity to own a piece of coastal Florida. Nestled in the sought-after Palmer neighborhood, this home has been lovingly maintained by the same discerning owners since 1999—a testament to the pride, care, and attention poured into every detail over the years. Set on an expansive 0.68-acre lot with 131 feet of Sarasota Bay frontage with two deeded private beach access points, the property is enveloped in lush tropical landscaping and exudes timeless Old Florida charm. The interior showcases a traditional layout with formal living and dining rooms, a spacious family room, private office, bonus room, a serene first-floor master suite, and three additional guest bedrooms. Designed for both everyday comfort and gracious entertaining, the home also features a screened-in pool and a covered boathouse accommodating vessels over 25 feet. Enjoy captivating views of the bay with breathtaking sunrises and sunsets from your own backyard oasis. Meticulously updated over time, the home includes a metal roof, 2 News AC's, PGT impact windows, a steam room, re-piping, and more—all reflecting the owners’ commitment to quality and preservation. Located just 15 miles south of downtown Sarasota and moments to Pineview (#1 Ranked School in Florida), nature parks, the Legacy Trail, this property blends unmatched privacy with access to world-class amenities. A truly special home....ready to begin its next chapter.

OSPREY

1042 N CASEY KEY ROAD

4 Beds

4 Baths

4,781 Sq.Ft.

$3,750,000

MLS#: A4650216

Premier Waterfront Opportunity in The Oaks Bayside
This grand estate home, perfectly positioned on a rarely available direct waterfront lot in the exclusive, gated Oaks Bayside community, offers sweeping views of Little Sarasota Bay and exceptional potential. With its expansive floor plan across three levels, soaring ceilings, and dramatic architectural features, this residence was built to impress—and now invites a new owner to make it their own.
The ground floor has been thoughtfully prepared for renovation, providing a blank canvas to bring your vision to life. Whether you imagine a guest or in-law suite, a luxury garage with a gaming lounge, a showcase for your fishing gear, or a green room for potting plants—the possibilities are endless.

A private dock awaits your custom design, offering direct access to the open bay and Gulf of Mexico. Just steps from the home, the community dock—exclusively for Oaks Bayside residents—adds even more coastal charm. Fish, launch a kayak, relax and watch the sunset, or gather with neighbors in this serene waterfront setting.

Ownership includes mandatory membership in The Oaks Club, unlocking an array of world-class amenities. Set across more than 1,000 acres, the club features two private 18-hole championship golf courses, 14 Har-Tru tennis courts, a croquet lawn, a junior Olympic swimming pool, state-of-the-art fitness center, and a stunning 34,000-square-foot Georgian-style clubhouse. A guest lodge and vibrant year-round social calendar complete this private country club experience.
You're not just creating a home—you're curating a luxury lifestyle in one of Florida’s most prestigious coastal communities.
This exceptional property is ready for your private tour at your convenience.

OSPREY

112 OSPREY POINT DRIVE

4 Beds

5 Baths

8,635 Sq.Ft.

$3,705,000

MLS#: O6305818

Sited at the end of a quiet cul-de-sac behind the gates of the prestigious Oaks Clubside in Osprey, Florida, this stately traditional custom estate offers refined living in one of Sarasota County’s most exclusive communities. Perfectly positioned on over three-quarters of an acre, the residence boasts serene preserve and fairway views, capturing the essence of Florida luxury living. Inside, discover graciously sized rooms, soaring ceilings, and abundant natural light that fills every space. The formal living room with gas fireplace and the formal dining room provide elegant spaces for entertaining. The open-concept kitchen and family room are the heart of the home, ideal for casual gatherings and everyday comfort. A large kitchen offers a generous walk-in pantry, plentiful storage, and a seamless flow into the family room and outdoor spaces. The primary suite is located on the main floor, offering a tranquil retreat with a spa-like bathroom, separate dressing room, and expansive walk-in closet. An office with fireplace is also on the main level, perfect for work-from-home privacy. Upstairs, two additional bedrooms and a bonus room provide a private haven for guests or multi-generational living. Step outside to the screened and covered outdoor living area, where a summer kitchen, cabana with full bath, and lush landscaping invite indoor-outdoor living year-round. It’s an entertainer’s dream, ideal for both intimate gatherings and grand events. Key features include wind-rated impact windows, new tile roof to be installed with a transferable 20-year workmanship warranty, $800,000+ in updates under current ownership, and situated on an oversized lot with ultimate privacy. As part of The Oaks Club, enjoy world-class amenities including two championship golf courses, 12 Har-Tru tennis courts, pickleball, croquet, a state-of-the-art WellFit Center, and exceptional dining at The Oaks Room, The Overlook, and The Tavern. This is more than a home—it's a lifestyle. Experience the timeless elegance, thoughtful design, and unmatched amenities of The Oaks Club in this remarkable estate.

OSPREY

550 DOVE POINTE

4 Beds

5 Baths

7,842 Sq.Ft.

$3,300,000

MLS#: A4656464

**FANTASTIC, FULLY RENOVATED ESTATE with LAKE / GARDEN VIEW is situated on a SERENE, INTERIOR, CUL-DE-SAC lot with NO FLOOD concern (Zone “X”) behind the Secure Gates of the highly sought after Bayside neighborhood within The Oaks Country Club community, just steps from Little Sarasota Bay. An Expansive Floorplan entails 4-BEDs plus 4-FULL BATHS while a full list of EXCEPTIONAL FEATURES is available upon request and includes Soaring 16ft and Vaulted Ceilings, Impressive White Oak and Marble Floors, Custom Crown trim, Plantation Shutters, many Built-Ins…to name a few. The Gorgeous, Chef’s Kitchen showcases marble counters, custom hardwood cabinetry and Galley Workstation Sink while premium appliances include LA CORNUE Gas Range, SUBZERO, BOSCH, etc. Enjoy your tranquil and private outdoor sanctuary from an expansive screened lanai with Heated Pool & Spa, Outdoor Kitchen and multiple covered seating areas while enjoying the surrounding butterfly, bee and hummingbird gardens and lake scenery. MANY RECENT UPDATES include Hurricane IMPACT Windows (2022), GENERAC Generator w/ Buried Propane Tank (2020), 3-HVAC Systems (2021), ROOF (2015), POOL HEATER (2025) and Much MORE! THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

OSPREY

662 FERNWALK LANE

4 Beds

4 Baths

4,359 Sq.Ft.

$2,995,000

MLS#: A4635707

Tucked away in a quiet cul-de-sac on a double lot beneath majestic oaks, this almost 5,000 sq ft, timeless 2-story home blends sophistication with modern comfort. Situated on the first hole of Heron Golf Course, the home features soaring 11-ft ceilings, marble floors, and crystal chandeliers. A Louis XVI fireplace anchors the sunken living room, while French doors and expansive windows invite sunlight into the sunroom with breathtaking golf course views leading to three patios perfect for entertaining or relaxation. A brick path winds through lush gardens to the adjacent guest house. This nearly 2,000 sq ft guest house features 2 bedrooms, 2 en-suite bathrooms, a spacious living room, dining room, an outdoor kitchen, and a private laundry room. Overlooking the pool and spa, this guest retreat offers privacy and convenience, ideal for extended stays, visiting family, or in-law suite. The Oaks club amenities include 2 18-hole championship courses, and world-class tennis and pickleball facility. Located near Casey Key and the powdery white sands of Siesta Key. Enjoy the arts in Downtown Sarasota and shopping at St. Armands Circle; approximately a 20 minute drive. Membership at The Oaks is required.

OSPREY

236 SAINT JAMES PARK

6 Beds

6 Baths

6,246 Sq.Ft.

$2,900,000

MLS#: A4644125

#A4642364

OSPREY

49 OSPREY POINT DRIVE

4 Beds

3 Baths

3,953 Sq.Ft.

$2,745,000

MLS#: A4642364

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