275 Lookout Point Drive, Osprey, FL 34229
Sources: Stellar MLS (listings + 12-mo closed sales), FEMA, modeled insurance. Interpretation: Momentum Research. Data notes
As of October 1, 2026, 275 Lookout Point Drive in Southbay Yacht & Racquet Club, Osprey is listed at $4,590,000 (5,279 sq ft, about $869 per sq ft). That is 1331% above Southbay Yacht & Racquet Club's median closed sale of $320,750 over the last 12 months (308 recorded sales). Per square foot it is above the community's recent $226/sq ft by about 285%. It came to market within the past week. Listing facts: built in 2007, a private pool, waterfront, HOA dues of $219/mo. Figures are from the MLS record and county data; deemed reliable but not guaranteed.
- No CDD assessment on record
- Built 2007 · 19 yrs
- 5,279 sq ft of living area
- 3-car garage
- Listed at $4,590,000 — recent neighborhood median sale price ~$320,750 (nearby sales; deemed reliable, not an appraisal)
- Active listing
- HOA $219/mo (per listing)
About this home
Experience exceptional waterfront living in Southbay Yacht & Racquet Club at this expansive custom John Cannon residence offering more than 5,200 square feet, 5 bedrooms, 5 baths and sweeping panoramic water views from both levels. Set along more than 135 feet of waterfront, the home was thoughtfully designed to embrace its remarkable setting, with soaring ceilings, generous expanses of glass and beautifully proportioned indoor and outdoor living spaces overlooking the bay and Intracoastal Waterway. A completely reimagined front drive and all-new landscaping create a striking first impression and a fresh, refined coastal presence.
Beyond the grand double-door entry, the home immediately opens to dramatic water views, drawing the eye through the interior and out toward the horizon. Ceilings rising to approximately 21 feet enhance the sense of scale, while a series of inviting living and entertaining spaces allow the home to feel equally suited for intimate evenings or larger gatherings. The kitchen serves as the heart of the residence, anchored by a substantial granite island and complemented by a gas cooktop with pot filler, while views stretch beyond the pool to the water.
A full bar and dedicated wine room enhance the main level, with an additional wet bar upstairs for effortless entertaining throughout the home. Privately positioned on the main level, the primary suite is a serene waterfront retreat with a sitting area, two generous closets and an expansive bath. Additional downstairs bedrooms are thoughtfully located on the opposite side of the residence, creating privacy and separation for family and guests.
Upstairs, either an office or a fifth bedroom offers an elevated and inspiring setting for work or quiet retreat, with access to the upper terrace and its sweeping water views. From both floors, the landscape of water and sky becomes part of the experience of the home. Outdoor living is equally memorable.
A heated pool and spa, covered and screened entertaining areas, outdoor kitchen, fireplace, expansive terraces and private dock create a seamless connection between the residence and the waterfront. Mornings begin with peaceful views across the water, afternoons unfold poolside, and evenings are defined by the colors of sunset. Southbay Yacht & Racquet Club offers one of the area's most distinctive boating lifestyles.
Its community-owned deep-water marina accommodates vessels up to 55 feet, allowing residents to walk or take a golf cart from home to their boat. Community amenities include a renovated clubhouse, geothermal pool, fitness center overlooking the marina, tennis and pickleball courts, bocce, shuffleboard, basketball, kayak storage, a waterfront park, approximately 20 acres of common grounds and miles of walking trails. Perfectly positioned between Sarasota and Venice and convenient to Siesta Key, Nokomis Beach, the Legacy Trail, Pine View School, waterfront dining, shopping and Oscar Scherer State Park, 275 Lookout Point is a compelling blend of scale, setting and lifestyle—a substantial waterfront residence with panoramic views, private outdoor living and direct access to the heart of Southbay’s boating community.
All 6 photos
Description provided by MICHAEL SAUNDERS & COMPANY and reproduced from the MLS; not independently verified.
Provided via the Stellar MLS Internet Data Exchange, as distributed by MLS GRID · Listings courtesy of Stellar MLS as distributed by MLS GRID · Listings courtesy of Stellar MLS as distributed by MLS GRID. · deemed reliable but not guaranteedIDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed by the MLS to be accurate.Every fact, sourced
Listing data, public records, our calculations, and what to verify — each fact shown once. Estimates and calculations shown are for general information only, are not appraisals or advice, and should be independently verified.
Listing facts MLS
Public records & third-party data
Calculated estimates
Buyer should verify Buyer verify
Estimated monthly payment
- Principal & interest $24,504/mo 77%
- Taxes $5,100/mo 16%
- Insurance $1,815/mo 6%
- HOA $219/mo 1%
$31,638/mo at 20% down, 30-yr @ 7.03% · edit any field to update.
Editable estimate — not a loan offer. Estimates only; see data & estimate notes.
Property taxes
✓ Certified tax roll · county-average rateProperty taxes in Florida are reassessed after a sale, so a buyer’s first full-year bill can be higher than the seller’s. Budget from this estimate, not the current bill, before you make an offer.
Most of this comes from Florida’s Save Our Homes assessment cap resetting when the home sells — the current owner’s protected assessment does not transfer to a new buyer.
Certified 2025 tax roll values for this parcel (Florida DOR). The roll gives values, not the bill; the current owner’s bill above is estimated from the taxable value.
Estimate my property taxes →Adjust for your exemptions, portability, and down payment
Sources: Florida DOR certified tax roll (2025), Stellar MLS; millage: Florida TaxWatch 2025 How Florida Counties Compare (county-average millage); school portion estimated at ~42% of total, capped at 6.50 mills. County public record, not MLS data — matched to this home by parcel ID. Estimates are not a tax bill; the county property appraiser and tax collector set the actual amount.
Flood zone & elevation
Sourced environmental data for the parcel. Confirm with FEMA and your insurer.
Not yet verified for this address. Look up the parcel at msc.fema.gov before relying on any flood assumption.
Approximate parcel elevation from USGS; confirm exact elevation with a survey.
Sarasota County is on the Florida coast; wind coverage is a major part of the premium. Premiums and coverage vary by home (roof age, wind mitigation, claims history); obtain a quote from a licensed insurer.
Natural hazard risk
FEMA National Risk Index for Sarasota County, FL: overall Relatively High. Ratings compare this county with every county in the United States for expected annual loss from each hazard.
Source: FEMA National Risk Index (county level, hazard risk ratings only). Ratings describe the county, not this parcel; the flood zone shown above is parcel-specific. Verify insurance requirements with your lender and agent.
Internet & broadband
Address-level fiber service is not confirmed for this home. Check the FCC National Broadband Map (broadbandmap.fcc.gov) or the provider for this address.
Cable broadband is common in Florida and Georgia towns but not confirmed for this address; verify with the provider.
5G home internet and satellite service depend on the exact location; check coverage for this address.
Pricing & the SOUTH VENICE market
How this home is priced against recent nearby sales, and where SOUTH VENICE has been over 25 years. Momentum Research analysis of Stellar MLS records; closed sales, deemed reliable but not guaranteed. Estimates only; see data notes.
This home’s $/sq ft vs. nearby sales
List $/sq ft against recent nearby closed sales; the community median is marked.
Price vs. size in SOUTH VENICE
Each dot is a closed sale since 2004 (4812 total). This home is the gold marker.
Sale price (y) by living area in sq ft (x). Stellar MLS closed sales.
Median $/sq ft by year
Community sold $/sq ft, 2012–2026. This home lists at $869/sq ft.
Median sale price by year
12-month median closed price, 2012–2026.
Market Heat by year (0–100)
Momentum Market Heat, 2013–2026. Now 34 (cold).
This home’s history
- 2007BuiltPer public record
- Oct 1, 2026First seen on movewithmomentum.comObserved at $4,590,000
- NowActiveCurrently for sale
Build year is from public record. The MLS list date is approximate (today minus the cumulative days on market the MLS reports, which can span relistings). Other milestones reflect movewithmomentum.com’s own observations since we began tracking this listing and are not the MLS listing history; dates and prices are deemed reliable but not guaranteed.
Price & listing history
Building permits
Comparable recent sales
6 closed sales within about 10 miles in Sarasota County in the last 18 months — same property type, living area within 30% of this home. Sold prices are MLS closed-sale records, deemed reliable but not guaranteed.
Median of these 6 sales: $320,750 ($226/sq ft). Directional only — a small or wide-radius sample. Shown for general reference only — not an appraisal or a statement of this home’s value.
The Messtimate
This is a deliberately dumb estimate — living area times a range of recent neighborhood $/sq ft, and nothing else. It is not an appraisal, not market value, and not a valuation of this home. Even a tight range from comparable sales can’t price a specific home — here’s why.
Directional estimate — 6 comparable closed sales within about 10 miles in Sarasota County, closed within the last 18 months, same property type, living area within 30% of this home.
Actual list price: $4,590,000 — compare it against the range above. The Messtimate is a blind sqft estimate; the list price reflects this specific home.
A 21% spread on the same house — and that gap is exactly what an automated guess can't see:
- Condition & updates — a renovated kitchen or new roof vs. dated finishes can swing value six figures; sq ft can't see it.
- The lot — this listing is waterfront; water frontage is priced far off a per-sq-ft average of the neighborhood.
- Outliers skew it — the band above comes from 6 nearby sales; one flip or distressed sale moves the whole $/sq ft.
- Carrying costs & concessions — this home carries HOA dues of $219/mo; with insurance and any seller-paid buydown, that changes what a buyer actually pays, and a sq ft estimate ignores all of it.
- The pool — a private pool carries cost and value that living area doesn't capture.
And here's what the live market is doing — which the number above ignores entirely:
- 2956 active listings competing, 971 under contract
- 10 closed here in the last 12 months
For reference, this home is listed at $4,590,000 ($869/sq ft). The list price is the seller's asking price and is not derived from this range.
Selling your own home? Try the Messtimate on your address →
Methodology: 5,279 sq ft × $312–$377/sq ft (interquartile band of 6 comparable closed sales within about 10 miles in Sarasota County, last 18 months; MLS closed-sale records). Estimate for general information only; not an appraisal, valuation, or offer. Updated October 1, 2026.
Momentum Property Score
42/100 is below average across the objective indicators below. It reflects only those measures — not the home’s quality, condition, or desirability.
A 0-100 score built from objective property and market data: flood risk, insurance, pricing, supply, affordability, and recent sales. Higher means more measures line up in a buyer’s favor. It reflects only the factors below.
Coverage: 5 of 8 indicators had valid data for this home; indicators without data are left out, not scored as zero. Momentum Scores are objective, rules-based indicators computed from listing facts, public records, and recent comparable sales. They do not measure property condition, quality, or investment suitability, and they are not appraisals, valuations, investment advice, or judgments about a neighborhood or who should live there. Verify independently.
The Momentum read
🟡 Asking $869 per square foot, about 285% above the community’s $226 median. SOUTH VENICE’s 12-month median sold price per square foot is $226. Median sold price per square foot is down 2.8% year over year. Confidence: Very High · 308 closed sales in 12 monthsMLS facts: Stellar MLS closed sales. A per-square-foot gap is context, not an appraisal; condition, lot, and view set the final number here.
Recent SOUTH VENICE sales closed near 93.5% of original asking.Why it matters: the community’s own record shows how far opening prices typically move, and how often buyers compete without financing.Momentum Research analysis of Stellar MLS records, community-level, 12 months ending September 20, 2026. Aggregates only; deemed reliable but not guaranteed.
What’s unique here: one of only 2912 active listings in SOUTH VENICE, no CDD assessment.
Jump to: About this home · Every number, sourced · Monthly cost · Flood & risk · History · FAQ
Updated October 1, 2026 · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
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Listed by MICHAEL SAUNDERS & COMPANY · MLS # A4707430
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Assigned schools
Schools currently assigned to this address in Sarasota County, provided as neutral factual data. Assignments can change — confirm current zoning with the school district. This is not a statement about the home's suitability for any person or family.
Assigned schools per the MLS listing — assignments can change; confirm current zoning with the district. Browse school-zone pages →
City, county & community guides
Where this home sits, with links to the matching guides. General reference only.
Buyer research checklist
Items worth confirming for 275 Lookout Point Drive, chosen from what the record shows. This is general guidance, not advice about this specific property.
- Built in 2007 (19 years): ask for the roof and HVAC replacement dates — insurers commonly ask for roof age on homes this old, and it changes the premium.
- HOA dues are listed at $219/mo: request the current budget, reserves, and rules before relying on that figure or on any restriction.
- Look up the parcel on FEMA's Flood Map Service Center and confirm with your insurer whether flood insurance is required.
- Get a homeowners insurance quote for this specific address in Sarasota County; a wind-mitigation inspection and, on older homes, a four-point inspection can change the premium.
- Private pool: confirm the barrier or alarm meets the state residential pool safety code and ask for pump, heater, and resurfacing records.
- Waterfront: confirm seawall or dock condition and permits, and ask who owns and maintains the shoreline.
- Listed living area is 5,279 sq ft: verify it against the property appraiser's record and measure before relying on it.
- Order a survey to confirm lot boundaries and easements.
- Review permit history with the county.
- Property taxes: the estimate on this page (about $61,200/yr) assumes reassessment at the list price less the homestead exemption. Estimated buyer taxes are about $41,950 more per year than the current owner’s estimated bill (+218%). Exemptions and portability change the actual bill — confirm with the county property appraiser.
- School zoning shown here comes from district data and changes; confirm the assigned schools directly with the district before relying on them.
Data sources & freshness
| Listing record | Stellar MLS, refreshed hourly (last: October 1, 2026) |
| Comparable sales | Stellar MLS closed sales within about 10 miles in Sarasota County, last 18 months, as of September 20, 2026 |
| Flood zone & elevation | Not verified for this address — look it up at msc.fema.gov |
| Taxes & monthly cost | Certified county tax roll (parcel-matched) × county millage; an estimate, not a bill |
| Insurance figure | Modeled estimate; obtain a real quote before offering |
| Schools | 2025-26 district assignments; verify with the district |
Momentum Research lines are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Estimates are informational, not appraisals or advice. Methodology: how Momentum scores are computed.
Frequently asked questions
How big is 275 Lookout Point Drive and when was it built?
Per the listing record, 275 Lookout Point Drive was built in 2007 and has 5,279 sq ft of living area, 5 bedrooms and 5.0 bathrooms. Living area and lot size come from the MLS record and should be verified against the county property appraiser.
What community is 275 Lookout Point Drive in?
275 Lookout Point Drive is in Southbay Yacht & Racquet Club in Osprey, Sarasota County. The comparable-sales section on this page shows recent closed sales nearby from the same MLS data.
Does 275 Lookout Point Drive have an HOA, and how much are the dues?
The listing reports HOA dues of $219 per month. Dues, what they cover, and the community's rules should be confirmed from the association's current documents before relying on them.
Why might property taxes on 275 Lookout Point Drive differ from the current owner's?
The estimate on this page (about $61,200 per year) assumes reassessment at the list price less the homestead exemption. Estimated buyer taxes are about $41,950 more per year than the current owner’s estimated bill (+218%). Florida reassesses a home after it sells; for a homesteaded seller the Save Our Homes cap on their assessment does not transfer, and a buyer's own exemptions and portability are applied separately, so the two bills usually differ. Any tax figure shown here is an estimate, not the actual bill — confirm with the county property appraiser and tax collector.
Is 275 Lookout Point Drive in a flood zone?
A flood designation has not been verified for this address. Look up the parcel on FEMA's Flood Map Service Center (msc.fema.gov) and confirm with your insurer.
Can I rely on the figures on this page?
No. Estimated taxes, insurance, payments, and any market or comparable-sales summary are opinions and estimates for general information only and should not be relied upon. Verify all information independently before making any decision.
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Opinion & estimate — do not rely on this page. Any figure on this page that is not a verbatim fact from the listing or a public record — including estimated property taxes, insurance, CDD/HOA amounts, mortgage payments, comparable-sales summaries, and market statistics — is an opinion and estimate provided for general informational purposes only. These figures may be inaccurate or out of date, are not appraisals, valuations, or financial, legal, tax, or investment advice, and should not be relied upon. Do not make any purchase, offer, financing, or other decision based on this page. Independently verify everything — price, square footage, lot size, year built, taxes, CDD/HOA, flood status, school assignments, permits, and community rules — with the listing broker, the county, your lender, a licensed inspector, an insurer, and your own advisors before acting.
Estimate methodology. Tax estimates apply county millage to the list price (less the homestead exemption where the parcel is matched to the certified roll) and will differ from the actual assessed bill. Cost and market figures are derived from available data and simple calculations, not a professional appraisal. We make no representation that any estimate reflects fair market value.
Equal Housing Opportunity. Content on this page is compiled from public records, MLS data, and automated sources and may contain errors or be out of date. It is general information only, not a representation about any specific property, community, builder, or association. Verify information independently before relying on it. Momentum Realty supports the Fair Housing Act and does not discriminate on the basis of race, color, religion, sex, handicap, familial status, national origin, sexual orientation, or gender identity. Information about schools, distances, and amenities is provided as neutral factual data to help you research the property and is not a statement about who should or should not live here or the suitability of the home or neighborhood for any person or group. School data may change — confirm current assignments with the school district.
Found an error? If you are the owner, listing agent, or a party to this property and believe any information is inaccurate, email and we will review and correct or remove it promptly.
Automated content. Some summaries, distances, and estimates on this page are generated automatically from public and proprietary data sources and may contain errors or omissions. We strive for accuracy but cannot guarantee the completeness or accuracy of any information. Verify anything important independently.
No warranty; measurements & photos. No guarantee, warranty, or representation of any kind is made regarding the completeness or accuracy of any information, descriptions, or measurements on this page — including square-footage measurements and property condition — all of which should be independently verified through appropriate means, including in-person inspection and public records. Photographs may be virtually staged or digitally enhanced and may not reflect actual property conditions. Momentum Realty and its agents expressly disclaim any liability in connection with the information provided.
MLS / IDX. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of the Stellar MLS Internet Data Exchange, as distributed by MLS GRID. Real estate listings held by brokerage firms other than Momentum Realty are marked with the listing broker's name and include the name of the listing agent. Data provided is deemed reliable but is not guaranteed by the MLS to be accurate. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Source: Stellar MLS, as distributed by MLS GRID. Listings courtesy of Stellar MLS as distributed by MLS GRID. All rights reserved.
Listing data is deemed reliable but is not guaranteed and is subject to change or withdrawal without notice. Square footage and lot size are approximate. Real estate brokerage services provided by Momentum Realty, licensed in Florida and Georgia. © 2026 Move With Momentum LLC.