440 CAMBRIDGE BOULEVARD, WINTER PARK, FL, 32789
Active78 days on marketListed May 7, 2026MLS #O6403694
About this home
440 CAMBRIDGE BOULEVARD
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully maintained and updated over time, this property combines functional living with key improvements that add long-term value and peace of mind. Inside, the open floorplan creates a bright, connected flow across the main living areas—ideal for both everyday living and entertaining. The separate family room adds valuable versatility, perfect as a media room, home office, playroom, or relaxed second living area. The bedroom layout is practical and comfortable, providing a solid foundation for personal touches and customization. Recent updates enhance both the appeal and functionality of the home, including a roof installed in 2020, HVAC system replaced in 2019, a new garage door with opener (2019), and fresh exterior paint completed in 2024. The bathroom has been refreshed with a new sink, toilet, and tub surround in 2025, offering a clean, updated feel. The outdoor spaces further elevate the property. An enclosed front porch provides a welcoming spot to enjoy a quiet morning or unwind in the evening, while the open rear patio is perfect for grilling, dining, or relaxing outdoors. The private backyard offers plenty of space to expand your vision, with strong potential to create a personalized outdoor retreat. With its solid layout, meaningful updates, and room to grow, this home presents an excellent opportunity for buyers looking to settle into a well-located property while continuing to enhance it over time. Situated in desirable Winter Park, the home benefits from a location known for its established charm, tree-lined streets, and convenient access to shopping, dining, parks, and everyday essentials, making it one of Central Florida’s most sought-after communities.
Facts & features
The home at a glance
2
Bedrooms
1
Bathrooms
988
Sqft
0.17 ac
Lot size
1
Garage
1950
Year built
One
Levels
$385
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$2,931 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$2,931/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
−6%
$/sqft vs Winter Park actives
$385 vs $345
Days on market
78 vs 34 typical
Where $385/sqft sits among the 313 Winter Park actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Lake Killarney
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Lake Killarney — neighborhood snapshot
Population
2,209
Median age
61
Median income
$68,693
Median home value
$396,822
Avg household
2
Households w/ children
107
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Park market
$473K → $500K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
144 of 313
Winter Park actives have cut their price
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 55% below the WINTER PARK 32789 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 440 CAMBRIDGE BOULEVARD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Dec ’25$490,000
240 CAMBRIDGE BOULEVARD · same community
3 bd · 2 ba · 1,630 sqft · $301/sqft · 178 DOM
Sold · Dec ’25$470,000
2381 ROXBURY ROAD · same community
3 bd · 2 ba · 1,785 sqft · $263/sqft · 24 DOM
Sold · Jun ’26$640,000
352 CAMBRIDGE BOULEVARD · same community
5 bd · 3 ba · 1,917 sqft · $334/sqft · 46 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Steeve Cadeau
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 440 CAMBRIDGE BOULEVARD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 440 CAMBRIDGE BOULEVARD — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Steeve's phone and CRM.
Straight answers
440 CAMBRIDGE BOULEVARD FAQs
What would the monthly payment be for 440 CAMBRIDGE BOULEVARD?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $2,931/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 440 CAMBRIDGE BOULEVARD?+
The most recent tax bill on record (2025) was $4,386. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Winter Park?+
At $380,000, this home is listed about 39% below the Winter Park median of $627,000. The market section on this page shows how the area is trending.
Which schools are assigned to 440 CAMBRIDGE BOULEVARD?+
Killarney Elementary (elementary), Edgewater High (high), College Park Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Under the WINTER PARK 32789 market on paper
$380,000 is 55% below the WINTER PARK 32789 median of $849,900, and at $385/sqft it sits under the Winter Park average of $425.
02Garden & Trees/Woods views
The garden and trees/woods view is part of what you're buying — views hold value independently of the structure.
03Time on market is leverage
78 days on market against a Winter Park median of 34 — sellers in this position are usually ready to negotiate.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS REALTY AT THE PARKS · Thomas Nickley, Jr. MLS #O6403694.
IDX 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 accurate by Stellar MLS.
Never miss a listing
New Winter Park homes, in your inbox
Like 440 CAMBRIDGE BOULEVARD but not quite? A daily digest of every new listing in Winter Park — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask Steeve to ping you on any price or status change →